#131 Yue Zhao: The Best Leaders Don’t Give You Answers

What if the secret to building a great career wasn't about having all the answers — but knowing how to ask the right questions?

Today's guest, Yue Zhao, has lived that philosophy across one of the most varied and impressive career paths you'll hear on this show. Yue is a Chief Product & Technology Officer turned executive coach. She helps aspiring executives accelerate their careers and reach the C-suite. Yue worked at Thumbtack, Meta, Instagram, and growth-stage startups. She co-founded a wine startup out of Harvard Business School, helped shape the future of Instagram Feed at Meta, and led product at McKinsey-backed Thumbtack from a 20-person garage startup to a scaled technology company.

But beyond the resume, Yue is someone who has thought deeply about what makes great leaders great, what it really takes to grow in your career, and why the best decision you can make isn't always the obvious one. She's also a career coach herself — so she brings both the frontline experience of building products people love and the perspective of someone who has helped countless others navigate pivotal career moments.

Whether you're just starting out, stuck at a ceiling, or wondering if it's time to make a leap — this conversation is packed with hard-won insight you won't want to miss.

Here's what you'll learn in today's episode with Yue Zhao:

• Why the best leaders never give you answers — and why that's actually the greatest gift they can give you

• How to choose your next job — and why your future manager matters more than the company name or the salary

• The one communication habit most product managers skip — and how mastering it will set you apart at any level

• What a wine startup, a bioengineering degree, and Instagram Feed have in common — and what Yue's winding path teaches us about building a career that compounds

• The mindset shift that changed how Yue coaches people — understanding what's within your control versus what isn't, and why confusing the two keeps so many talented people stuck

• Why two years is not that long — and how reframing the length of your career can take the pressure off your next decision

• The simple calendar trick Yue uses to get back on track — when life, work, or routines go sideways

#130 David Herrera: Leave No Doubt

What if the values that made you who you are — resilience, service, empathy — could become the operating system for an entire organization?

Today's guest grew up in Hialeah, Florida, the son of Cuban immigrants who arrived in America with almost nothing and built everything through grit, integrity, and an unwavering belief that hard work is the price of admission. He lost his father at 12 years old, found his footing in the U.S. Army — where he'd eventually jump out of planes at night as part of an Airborne unit — and then quietly built one of the most storied careers in the travel industry.

David Herrera served as President of Norwegian Cruise Line, where over more than a decade he helped transform the company's commercial operations, led its expansion into China, and championed a genuine, veteran-driven military appreciation program that earned him letters, mugs, and thank-you notes from guests whose gratitude had nothing to do with the bottom line.

But what strikes you most about David isn't the titles or the milestones — it's that he leads the same way his mother lived, the same way his Army sergeant Mahoney taught him: from the front, with his word as his bond, leaving no doubt whose side he's on.

In this conversation, we talk about growing up in a Cuban immigrant household that embodied the American dream, what the military teaches you about trust and team that no MBA program can replicate, how he thinks about culture not as a poster on the wall but as the answer to the question — who's winning here, and why? — and what it really means to be a servant leader when the stakes are high.

In this episode we discuss:

• Hire your manager, not just your job. The person above you shapes everything about your early career experience. Choose them wisely.

• If you're not early, you're late. Punctuality is ultimately about respect — for other people's time and for the commitments you make.

• Share the victory, own the setback. When things go right, celebrate the team. When things go sideways, step forward and take responsibility.

• Culture is what gets rewarded. Not what's written on the wall — but who's winning in your organization and what it is about them that you actually respect and want to replicate.

• Treat everything as a learning opportunity. Doesn't matter if you're painting parking lots in Miami heat or running a division — be in the moment, observe what works, and study what doesn't so you can avoid it.

• Lead from the front. Never ask someone to do something you haven't done or aren't willing to do alongside them. That credibility is the foundation of real trust.

• Know your foxhole friends. Who in your life both genuinely cares about you and is capable of showing up when it counts? That combination is rarer than most people realize.

• Sometimes the right business decision comes at a personal cost. Separating emotion from judgment is one of the hardest and most important skills a leader can develop — and it never fully stops stinging.

SHOW NOTES

(0:00 – 4:30) Growing Up in Hialeah: The Cuban Immigrant Foundation David opens up about his parents leaving Cuba after Castro's regime and arriving in America with almost nothing. His father went from washing dishes to owning the first Cuban lunch truck in Miami — and then helped four or five of his friends do the same. His mother graduated top of her class at the University of Havana and started on a factory floor before working her way up. Together they eventually opened a small accounting practice in Hialeah, Florida. David reflects on what it meant to grow up watching that level of quiet, relentless work ethic up close.

(4:30 – 8:00) Losing His Father at 12 and the People Who Showed Up David's father passed away suddenly when David was just 12 years old. He shares how his mother and grandmother worked to keep life as normal as possible, and how the small gestures of people around him — a friend's father driving him places, a stranger stopping to take off his hat at the cemetery — left impressions that have lasted over 40 years. This section is one of the most emotional and human moments of the entire conversation.

(8:00 – 11:00) His Mother's Greatest Lesson: We Don't Take Charity After his father passed, the school offered to cover the cost of a class performance for David. When his mother found out, she marched down to the school and refused. "We don't take charity. We make our own way." David credits this moment as one of the defining lessons of his life — and the origin of the integrity and self-reliance that would shape his entire career.

(11:00 – 14:00) Faith, Community, and Two Years in Shanghai David talks about the role faith has played throughout his life — not as something he broadcasts, but as a source of grounding and community. He shares the story of moving his entire family to Shanghai in 2016 to launch Norwegian's China business, and how his wife Patty, his childhood sweetheart, turned what could have been a disruption into an adventure. One of the warmest sections of the conversation.

(14:00 – 17:30) First Jobs: Painting Parking Lots in Miami Heat David's first job was painting parking lot lines at his baseball coach's summer camp — in Miami, in the summer, bending over with a brush in the heat. By eighth grade he and a buddy had a side hustle painting offices. He reflects on what those early jobs taught him about being present, learning from every environment, and finding value in every experience regardless of the title.

(17:30 – 21:00) The Army, Airborne School, and What the Military Really Teaches You David enlisted right out of high school and eventually became part of a six-man Airborne long-range surveillance unit. He talks about what jumping out of planes at night actually feels like, why rugby is the closest civilian sport to the military experience, and what the armed forces give you that no MBA program can — an accelerated, unbreakable bond with the people beside you.

(21:00 – 25:00) Sergeant Mahoney: The Mentor Who Showed Up at Thanksgiving Two months into his posting in New York, David's team sergeant John Mahoney asked him what he was doing for Thanksgiving — and then simply told him he was coming home with him. That relationship became one of the most defining of David's life. The lesson Mahoney embodied: lead from the front, never ask someone to do something you haven't done or aren't willing to do alongside them, and let your word be your bond.

(25:00 – 29:00) Dartmouth, Finance, and an English Minor David chose Dartmouth for its culture of support over competition, and double dipped in finance and English — one for his career, one for his soul. He reflects on why feeling comfortable in your environment unlocks your best work, and how that realization shaped the kind of workplace culture he would eventually build at Norwegian.

(29:00 – 34:00) Defining Culture: What Gets Rewarded Is What Gets Repeated This is one of the richest sections of the conversation. David shares how he defines culture not by what's posted on the wall, but by looking at who's winning in your organization and asking why. He walks through several of Norwegian's cultural pillars including family first always, take your job seriously but not yourself, think like a guest but decide like an owner, and the one he's most proud of — leave no doubt whose side you're on.

(34:00 – 38:00) The Foxhole Friends Framework David reframes the concept of foxhole friends with a question that stops you cold: if you were sick and needed two people standing outside your door to make you feel completely safe — not just people who love you, but people who are also capable of showing up — who would they be? One of the most memorable and shareable moments of the entire episode.

(38:00 – 42:00) The Hardest Business Decision: Closing the China Office After building Norwegian's China operation from two employees to 65, achieving the highest-yielding product in the market within 18 months, and living two years in Shanghai with his family — David had to support the decision to shut it down. He talks honestly about the emotional cost of separating personal investment from business judgment, and why being united behind a team decision is itself a form of leadership.

(42:00 – 46:00) The Military Appreciation Program and the Mug That Meant Everything David shares one of his proudest accomplishments at Norwegian — creating a genuine, veteran-designed military appreciation program complete with challenge coins, pins, and a program built by veterans for veterans. The letters and emails that came back from guests, including a handmade mug from a veteran who just wanted to say thank you, represent exactly the kind of impact he set out to have.

(46:00 – 50:00) Great Stirrup Cay and the Next Chapter for Norwegian David gives a behind-the-scenes look at Norwegian's massive reinvestment in their private island, Great Stirrup Cay — a 28,000 square foot pool, a 170-foot tower, and a vision to give guests more freedom and flexibility than ever before. He describes what it feels like to work on a project of that scale across teams who didn't know each other but shared a vision.

(50:00 – 54:00) Rapid Fire + Parting Advice David closes with his best career advice — treat everything as a learning opportunity, hire your manager, be a sponge, and get to know everyone around you from the security guard to the maintenance staff. He also opens up about fishing as his mental health reset, patience as the thing he wishes he'd learned sooner, and what it means to go to sleep at night with only one voice in your head.

Key Quotes from This Episode

"If you're not early, you're late — and that's about respect."

"Culture is what's valued in your organization. Look at who's winning and ask yourself why."

"Who are your two people? The ones who not only love you, but are capable of showing up when it counts."

"Share the victory, own the setback."

"Leave no doubt whose side you're on."

"We don't take charity. We make our own way."

#129 Howard Chasser: Do What You Love or Start Over

What does a childhood obsession with comic books, a family health food store, and a Roberto Clemente rookie card have in common? For Howard Chasser, they're all threads in a life built around passion, people, and the relentless pursuit of doing work that actually means something. Howard spent over 30 years running a natural food store on Long Island that his parents opened in 1976 — navigating the loss of his father at 17, a monster expansion, a brutal economy, Superstorm Sandy, and a divorce — before walking away and ultimately finding his way back to what he'd loved since childhood: sports cards and collectibles. Today he runs a thriving sports cards business built not on transactions, but on trust, genuine enthusiasm, and an ability to make people feel like family. This is a conversation about reinvention, resilience, and what happens when you finally stop fighting what you were always meant to do.

In this episode, Howard shares:

• Why the things we're meant to pursue often find us before we're ready for them — and how a $68 baseball card his mom almost didn't buy changed the entire trajectory of his life

• How soft skills will outwork hard skills in the room — Howard was a B+ student surrounded by straight-A accounting majors, but his years behind a store counter made him the one people actually wanted to hire

• Why you can hold an apology and a boundary at the same time — the moment he snapped at an employee taught him that accountability and delivering a message aren't mutually exclusive

• What a difficult customer's secret revealed about human nature — the woman who cursed at his staff turned out to be a mother whose teenage daughter had terminal cancer, and it changed how he sees every hard interaction

• How the right door often only opens after the wrong one finally closes — after a year of uncertainty post-store, Howard reluctantly returned to card shows and stumbled into his true calling right before COVID sent the hobby through the roof

• Why your kids reflect your energy, not their own chaos — a therapist-backed insight that transformed how he showed up as a father, and a lesson that applies far beyond parenting

[0:00 – 4:00] Childhood Heroes & The Comic Book Obsession Howard opens up about his unlikely childhood hero — The Thing from the Fantastic Four — and what drew him to a character who stood out, felt socially out of place, but always tried to help people. He talks about the comic book store that changed his life and the man behind the counter who made him fall in love with collecting.

[4:00 – 10:00] The $68 Card That Started Everything Howard recalls his first baseball card show at around age 12, the moment a 1955 Topps Roberto Clemente rookie card stopped him in his tracks, and the half-hour meltdown it took to convince his mom to spend money the family didn't really have. He didn't even know who Clemente was — but the card picked him anyway.

[10:00 – 16:00] Learning Who Clemente Really Was Howard describes how collecting Clemente's cards eventually led him to learn about the man himself — his legacy as a Puerto Rican hero, his humanitarian work, and the plane crash that killed him while delivering aid to earthquake victims in Nicaragua. He also shares what people who knew Clemente personally told him about the kind of man he was.

[16:00 – 22:00] Growing Up in the Family Business Howard's parents opened a natural food store in 1976 after his father was laid off during a recession. Howard reflects on what it was like to grow up in that store, the financial hardship the family faced, and how scarcity taught him to take extraordinary care of everything he owned — a habit that would serve him well as a collector.

[22:00 – 28:00] Losing His Dad at 17 One of the most powerful moments in the episode. Howard's father passed away from a heart attack at 65, and Howard reflects on the complicated grief of being a teenager who was frustrated with his dad's health choices right up until the moment he was gone. He talks about how that loss became one of the greatest motivators for how he takes care of himself today.

[28:00 – 35:00] The Dream Job He Walked Away From Fresh out of SUNY Albany with an accounting degree, Howard landed a job at one of the Big Six accounting firms — and walked away after six months. He talks about how the corporate politics caught him off guard, what that year of "finding himself" looked like, and how guilt over his mother struggling alone in the store eventually pulled him back in.

[35:00 – 43:00] Running the Store & The Monster Expansion Howard describes what it took to nearly quadruple the size of the natural food store — moving from a shopping center into a standalone space, navigating a four-week gap where no store was open, and dealing with Murphy's Law at every turn. Including a lighting fixture disaster that had him lying flat on a flatbed truck outside the store doing deep breathing.

[43:00 – 51:00] The Year From Hell & Knowing When to Walk Away 2008 brought a perfect storm: his mother passed in April, a massive competitor opened up the street in June, and the economy collapsed in August. Howard walks through the slow unraveling of the business over the following years — Superstorm Sandy, a divorce, losing his best people — and what finally made him decide to close.

[51:00 – 58:00] The Worst Six Months & Walking Out the Door Howard shares the painful story of entering a last-ditch partnership to keep the store alive, being completely marginalized by his new partners, and the moment he unplugged his computer, tucked it under his arm, and never looked back. He reflects on why, in hindsight, he's grateful it ended the way it did.

[58:00 – 1:05:00] Rediscovering the Hobby & Finding His Calling With no clear path forward, Howard reluctantly set up at a card show just to pay some bills — and immediately remembered why he loved it. He talks about the moment he realized this could actually be a business, the timing of COVID exploding the collectibles market, and what it felt like to finally be doing work that made him feel alive.

[1:05:00 – 1:13:00] What the Store Taught Him About People Howard shares the story of a father and son who walked an entire card show and were acknowledged by almost nobody — and what it meant to them when Howard treated them like family. He talks about the competitive advantage of genuine human connection and why so many dealers miss it entirely.

[1:13:00 – 1:20:00] Advice for Getting Back Into the Hobby Howard's single biggest piece of advice: spend a lot of time before you spend a lot of money. He breaks down the nuances of grading, raw cards, and how to figure out what kind of collector you actually want to be before going all in.

[1:20:00 – 1:28:00] The Mount Rushmore of Baseball Cards A fun and surprisingly deep conversation about which players sit at the top of the collectibles world, where Jackie Robinson and Roberto Clemente fall in the hierarchy, and why a player's cultural legacy can be just as powerful as their stats when it comes to long-term collectability.

[1:28:00 – 1:38:00] Parenting, Presence & Two Lessons That Changed Everything Howard shares two therapist-backed insights that transformed how he showed up as a father — the power of natural consequences over punishment, and the practice of giving yourself a timeout to check your own energy before engaging with your kids. Raw, practical, and surprisingly universal.

[1:38:00 – 1:45:00] Career Advice & Closing Thoughts Howard wraps with his biggest pieces of advice for anyone early in their career: find work you love, get financially literate young, and trust that when one door closes, something better is usually on the other side. He also shares his two book recommendations — The Seven Habits of Highly Effective People by Stephen Covey and Passionate Marriage by David Schnarch.

#128 Eri Iozdjan: Having a Bias For Action

What if the secret to building a thriving business wasn't an MBA, a venture capital check, or even a business plan — but simply the courage to say yes before you're ready?

Today's guest is Eri Iozdjan, founder of Maven Lane, a premium direct-to-consumer furniture brand that's redefining what it means to bring quality, story, and soul to the spaces where we live our lives. Eri's journey is anything but conventional. He arrived in the United States from Bulgaria at age five, speaking no English, with his young mother and nothing but a relentless drive to figure it out. From working HVAC jobs as a teenager, to producing a New York Fashion Week runway show, to building a furniture brand that sells out its first inventory run in weeks — Eri is proof that the most unlikely paths can lead to the most extraordinary destinations.

In this episode, Eri pulls back the curtain on what it really takes to build something meaningful from the ground up — and why staying true to your vision, even when the money is tempting you otherwise, is the ultimate competitive advantage.

Here's a taste of what you'll walk away with:

• Why saying yes before you're ready is the single greatest career accelerator — and how Eri used it to go from knowing nothing about furniture to building a brand people call life-changing

• The complacency trap that derails even the most successful entrepreneurs — and the simple mindset shift Eri uses to stay sharp no matter how well things are going

• How a late-night dream gave Eri the name, the logo, and the soul of Maven Lane — and what it teaches us about trusting our instincts

• The phone call from a stranger that gave Eri the confidence to go all in — and why that one conversation changed everything about how he saw his business

• Why "nobody cares" is actually the most liberating career advice you'll ever receive — and how embracing it can unlock a level of ownership and accountability most people never find

This is a conversation about grit, creativity, identity, and the quiet power of just getting to tomorrow. You're not going to want to miss it.

Show Notes with Time Stamps

[00:00 – 03:30] The Origin Story: From Bulgaria to Fort Wayne, Indiana Eri shares what it was like immigrating to the US from Bulgaria at age five with his young mother, who was just 22 at the time. He talks about growing up without his biological father, the tight-knit community life in Bulgaria, and how his grandfather became one of the most influential figures in his life.

[03:30 – 06:00] The American Dream and What Drove the Move Eri reflects on what prompted his family's decision to leave Bulgaria — limited economic opportunity, the pull of the American dream, and family members already planted in the US who painted a picture of what was possible.

[06:00 – 09:00] Lessons from Mom: Do and Ask Questions Later Eri unpacks the single most important lesson his mother modeled for him — not through words, but through the way she lived. She cleaned houses, raised a child in a country whose language she didn't speak, and just figured it out. Eri traces how that ethos has shaped every major decision he's made.

[09:00 – 12:30] Muhammad Ali, Boxing, and Finding an Identity Eri talks about discovering boxing in middle school as a way to navigate a rough school environment — and how it quickly became so much more than self-defense. He shares why Muhammad Ali was his hero, not just for his boxing, but for his willingness to stand for something in the face of adversity.

[12:30 – 16:00] First Jobs: HVAC, Crawl Spaces, and the Weight of Responsibility Eri recalls working alongside his stepfather in his HVAC company as a teenager, including a vivid memory of walking across ceiling joists above a dinner party and being told he simply could not slip. He reflects on what that experience taught him about preparation, professionalism, and what it means to do a job for someone else.

[16:00 – 20:00] Skipping College and Starting a Career in Sales Eri explains why he didn't follow the traditional university path, instead entering a technical honors program during high school that allowed him to work as an auto mechanic apprentice while earning his degree. He shares how he eventually landed a sales role at an industrial factory automation company and was handed a quarter of the country to manage as sales director.

[20:00 – 25:00] The College Conversation: Is It Worth It? A candid and wide-ranging conversation about the value of higher education, homeschooling, and how both Eri and the host are thinking about their kids' futures. Eri reflects on the feeling of being "left behind by his own design" when his friends went off to university — and what he would do differently with the benefit of hindsight.

[25:00 – 29:30] Moving to Denver: Love, Risk, and a Leap of Faith Eri shares the story of meeting his now-wife, learning about her apparel company, and making the decision to leave a growing sales career, abandon his Los Angeles acting dreams, and move to Colorado sight unseen with a woman he had just started dating. He reflects on why, at 22 or 23, the room for error is far greater than it feels.

[29:30 – 35:00] Director of Marketing at an Apparel Brand: Learning to Tell a Story Eri walks through his role at his wife's inclusive athletic apparel company — building the Shopify store from scratch, running advertising campaigns, overseeing creative direction, and developing the formula for a successful product launch. He reflects on the most important thing he learned: how to tell a compelling story that moves people.

[35:00 – 40:30] Producing a New York Fashion Week Show One of the most gripping segments of the episode. Eri describes what it took to produce a runway show at Sony Hall in New York City — casting models, choreographing outfit changes to specific BPMs, rehearsing in a warehouse, and managing the controlled chaos of New York. He reflects on what the experience unlocked in him: the belief that you can say yes to something you have no idea how to do and actually pull it off.

[40:30 – 46:00] The Birth of Maven Lane: Spotting a Gap in the Market Eri explains how a conversation with his neighbor and co-founder planted the seed for Maven Lane. He walks through his analysis of the furniture market — the inaccessible luxury players at the top, the particle board garbage at the bottom, and the wide open space in between for a brand that offered quality, story, and accessibility all at once.

[46:00 – 51:00] Launching Maven Lane: The First Sale and the Phone Call That Changed Everything Eri recalls the surreal experience of selling out his first inventory run in three to four weeks instead of three months — and the unforgettable phone call from a stranger who tracked down his personal cell number through her credit card company. She told him he was doing something special and ended the call by praying over him. Eri credits that moment with giving him the confidence to go all in.

[51:00 – 56:30] The Name, The Logo, and the Dream That Started It All Eri reveals the origin of the Maven Lane name — a vivid dream involving dark New York City alleyways, a Victorian lantern, and an ornate wooden door that blinded him with light when he finally pushed it open. He explains how that door became the centerpiece of the Maven Lane logo and what the dream taught him about trusting his instincts.

[56:30 – 01:02:00] Product Development: The Atlas of Furniture Design and the Vietnam Factories Eri pulls back the curtain on how Maven Lane develops its products — from analyzing catalog gaps and price point tiers, to drawing inspiration from a furniture design encyclopedia dating back to the 1700s, to making eight or nine trips to Vietnam to work directly with factory partners he now considers close friends. He also shares the story behind the fan-favorite arch cabinet and how his wife convinced him to use the oversized handle everyone now loves.

[01:02:00 – 01:06:30] The Hardest Part: Staying True to Your Vision Eri reflects on the most difficult ongoing challenge of building Maven Lane — the constant temptation to chase revenue by compromising on quality and vision. He shares that despite data showing he could add significant top-line revenue by selling cheaper products, he refuses, because that's simply not who Maven Lane is or ever will be.

[01:06:30 – 01:10:00] The Complacency Trap and Keeping the Details Sharp Eri shares his biggest lesson learned: that success can breed complacency, and complacency is where businesses quietly begin to unravel. He references the cyclical principle of weak times and strong times and explains why staying dialed in on the details — no matter how well things are going — is the most important discipline an entrepreneur can develop.

[01:10:00 – 01:14:30] Who Has Impacted Eri's Career the Most Eri pays tribute to his grandfather, who passed away last year and who he describes as his best friend and greatest mentor. He shares his grandfather's signature approach to problems — casually asking "what's next?" no matter how dire the situation — and reflects on how that perspective taught him that everything always passes, and all you have to do is get to tomorrow.

[01:14:30 – 01:20:00] Books, Documentaries, and Daily Habits Eri shares the books that have impacted him most including The Alchemist, The War of Art, Atomic Habits, and Traction. He recommends the documentary Jiro Dreams of Sushi as a meditation on passion and purpose, and talks about his evening meditation and prayer practice and the stretching routine he credits with helping him wind down and sleep better.

[01:20:00 – 01:28:00] The Sleep Conversation: Rings, Dilators, Mouth Tape, and More A candid and entertaining deep dive into sleep optimization — covering Oura Ring data, nasal dilators, mouth tape, CBD/CBN, Tension Tamer Tea, and the importance of sleep consistency over sleep quantity. Both Eri and the host swap notes on what has and hasn't worked for them.

[01:28:00 – 01:32:00] Rapid Fire: Career Advice, Life Lessons, and Words for the Next Generation Eri closes with his best career and life advice: nobody cares — it's up to you. He wishes he had understood the value of time earlier, and leaves listeners with three pieces of advice for anyone early in their career: build a specific skill around your interests, surround yourself with people you respect, and be brave.

#127 Travis Rea: Embracing the White Belt Mentality

What happens when a classically trained chef who cooked at Michelin-starred restaurants decides the future of cooking isn't fire—it's light?

Today's guest is Travis Rea, Head of Culinary at Brava, the company that's reimagining home cooking with an oven that uses infrared light instead of traditional heat. But Travis's path to revolutionizing kitchen technology wasn't straightforward.

Born and raised in Houston, he grew up watching his mom cook from scratch and fell in love with the transformation of ingredients at just eight years old. That passion led him to ditch a conventional business career for culinary school in San Francisco, where he spent four grueling years cooking at Restaurant Gary Danko—eventually helping the restaurant earn its Michelin star.

But after years of vampire hours and relentless pressure, Travis made a bold pivot back to the business world, spending eight years at Williams-Sonoma developing over 800 food products and collaborating with legendary chefs like Thomas Keller. When he first heard about Brava—a startup claiming they could sear a steak in seven minutes using light bulbs—he thought it was "total nonsense."

Now, eight years later, Travis has helped build a product that's been used over 13 million times, with a digital library of 9,000+ recipes. This is a story about knowing when to pivot, surrounding yourself with people smarter than you, and why the best career moves often require you to embrace being a beginner all over again.

What You'll Learn in This Episode:

• How failing a class became the wake-up call that changed everything – Why Travis's freshman year failure was "one of the best things that happened" to him and taught him the importance of living up to his own potential

• The real cost of following your passion – Why Travis walked away from Michelin-starred kitchens after realizing he loved cooking but couldn't sustain the restaurant lifestyle for 30 years

• How to know when you're ready for a pivot – The signals Travis noticed (and ignored) that revealed he was reading cookbooks while his peers read marketing journals, and what that meant for his career

• Why working for the best matters more than the biggest paycheck – Travis's philosophy on taking lower-paying jobs at elite organizations early in your career and how it compounds over time

• The white belt mentality in action – What it's like to be the only "cook" in a house full of physicists and engineers, and why being the least qualified person in the room might be exactly where you need to be

Time-Stamped Show Notes

[00:00 - 05:30] Growing Up in Houston & The Love of Cooking

• Born and raised in Houston, Texas

• Father was a cardiovascular thoracic surgeon, mother was a home cook and baker

• First cooking memory: making eggs with his mom at age 8

• Watching the transformation of liquid egg to solid "blew my mind"

• Mom's signature dish: dinner rolls dipped in melted butter

• Early exposure to fresh ingredients and farmers markets shaped his palate

[05:30 - 12:00] Education as a Non-Negotiable Value

• Parents met in college; education was always the top priority

• Attended elite college prep school in Houston

• The lesson: "They can't take education away from you"

• Being a solid B student who learned how to write

• Choosing Trinity University over University of Colorado Boulder

• "I knew myself - I would fail out in a year at a party school"

[12:00 - 18:30] The Failure That Changed Everything

• Failed freshman writing workshop despite it being his strongest subject

• Didn't turn in three papers after finishing fraternity pledging

• Parents' disappointment was hard, but his own disappointment was worse

• Confronted professor: "I'm not the guy you think I am"

• Retook the class and earned an A

• "That sting hurt" - became the wake-up call that transformed his approach to education

• Switched from English major to marketing and business

[18:30 - 24:00] The Pull Toward Culinary School

• Spent college years reading cookbooks while peers read marketing journals

• Watching Julia Child and Jacques Pépin instead of typical TV shows

• Did restaurant work and thought "no way, these guys work too hard"

• Internship in public relations/advertising - "I hated it"

• Realized: "I'm reading cookbooks for fun, not AdAge"

• Dinner with parents: "I have to go to culinary school"

• Parents' response: "This will be your grad school"

[24:00 - 30:00] Culinary School & Arriving in San Francisco

• Looked at Culinary Institute of America in New York vs. California Culinary Academy

• "I don't like snow, I'm not a cold guy"

• Visited San Francisco as an adult: "Within 24 hours I was like, yeah, that's where I'm going"

• Started culinary school summer of 2001

• Bay Area had just experienced the dot-com bust

• Friends working in tech while he pursued cooking

[30:00 - 38:00] Breaking Into Restaurant Gary Danko

• Did a stage (internship) at Gary Danko after eating there with parents

• Loved the style: revolutionary menu format, formal but not stuffy

• Told sous chef: "I'll do anything" and "I'm gonna keep doing this until you give me a job"

• Started in pastry under Belinda Leon (now James Beard Award winner)

• Spent one year in pastry before moving to the hot line

• Pastry made him "more meticulous" and changed how he approached cooking

[38:00 - 45:00] Lessons from Belinda Leon & the Pastry Station

• Greatest lessons: perseverance, repetition, focus, and speed

• "I was meticulous but not fast" - had to work hard on speed

• Making dozens of different items daily: crème brûlée, ice creams, soufflés

• The camaraderie and internal competition

• Contest to see who could make the most beautiful egg whites

• Team of three to four people on pastry

[45:00 - 52:00] The Crucible of the Hot Line

• First night on fish/veg station: "I felt like I was drowning"

• The sound of the ticket machine: "My seventh level of hell"

• Major mistake: strained butter-water mixture directly onto the flat top

• Caused smoke and fire on first night

• Sous chef: "Sink or swim time, what are you gonna do?"

• "I knew I wasn't gonna quit"

• Slowly got better through repetition and persistence

[52:00 - 58:00] Working with Gary Danko & Earning the Michelin Star

• Gary gave cooks creative freedom to put dishes on the menu

• "Find a way to say yes" - the hospitality mentality

• Gary's lesson: "I will never experiment on my guests"

• This was around when sous vide was becoming popular (2004)

• Gary wasn't a tyrant but held the line when needed

• "Chef means chief - they are the one in charge"

• Was there when restaurant earned its Michelin star

• Michelin inspectors are completely undercover - "you don't know who they are"

[58:00 - 63:00] The 1 AM Wake-Up Call

• After four years at Gary Danko, cleaning cutting board at 1 AM

• "What am I doing? I have a business degree"

• Realized he wasn't willing to put in 30 years to get to Gary's level

• Loved the idea of having his name on the door, but not the path to get there

• The lifestyle was taking its toll: vampire hours, no social life, hard to maintain relationships

• "I felt like a cooking robot and it was taking away the joy"

• The pressure and lifestyle worked for some, but not for him

[63:00 - 70:00] Pivoting to Williams-Sonoma

• Best friend's aunt's best friend's daughter worked at Williams-Sonoma

• Initially interviewed for assistant buyer position for cookbooks

• Redirected to Food Development department during interview

• Started as merchandise coordinator (entry-level retail buyer role)

• Food Development was different: created Williams-Sonoma branded products

• Filled holes in the market with new concepts

• Example: Created slow cooker sauces to complement All-Clad slow cooker launch

[70:00 - 76:00] Rising at Williams-Sonoma

• Manager left after one year - Travis asked for the job

• Boss: "I don't know if you're ready"

• Travis: "Just give me a chance"

• Did the job for three months before officially getting the role

• Ran the team for seven years

• Launched over 800 unique SKUs in eight years

• Got to work with Thomas Keller, Tom Colicchio, and other celebrity chefs

• His Gary Danko background gave credibility: "I spoke the same language"

[76:00 - 82:00] The Flour & Water Cookbook

• Cooked with Thomas McNaughton at Gary Danko

• McNaughton opened Flour & Water, started getting acclaim

• Dinner conversation: Tom mentioned thinking about a cookbook

• Travis: "Do you need any help? I don't know anything about pasta"

• Became lead recipe tester and writer

• Would watch Tom or other chefs make dishes and document everything

• "Proving you could take restaurant concepts and translate them to home cooking"

• Flour & Water: 15 years old, specializes in handmade pasta and Neapolitan pizza

[82:00 - 88:00] Revolution Foods & NatureBox

• Left Williams-Sonoma after eight years - wanted to advance and do something different

• Revolution Foods: served healthy school lunches to underprivileged kids

• Great company but "the work wasn't the best fit for me"

• Moved to NatureBox: "Netflix of snacks"

• First D2C (direct-to-consumer) company experience

• Exposed to e-commerce, venture capital, startup culture

• First time working closely with software engineers and product teams

• Wife was pregnant with first child when he started (2015)

[88:00 - 95:00] Discovering Brava: "Total Nonsense"

• Heard about company building smart oven that cooks with light

• Could sear a steak in seven minutes

• Travis's reaction: "That sounds like total nonsense"

• "You can't cook something with a light bulb - Easy Bake Oven, haha"

• Didn't even know what IoT (Internet of Things) was - had to look it up

• Was referred by former Williams-Sonoma test kitchen director

• Very skeptical going into the interview

[95:00 - 102:00] The House in Newark & First Week

• Company operating out of a house in East Bay (Newark, California)

• Interviewed in a bedroom

• Building prototype in garage with welding masks

• "20 dudes at standup desks - felt like the show Silicon Valley"

• Surrounded by people "deep in physics and mathematics"

• When they did the demo: "It blew my mind - it actually did what they said"

• Joined as first culinary hire, Head of Culinary

• First week at Brava was the company's first week having an office

[102:00 - 107:00] The $20 Million Demo

• Had exactly four days to prepare for investor demo

• Didn't realize the stakes - it would land nearly $20 million

• Cooked filet mignon with potatoes and broccoli

• Showed multi-zone cooking capability

• Engineers controlling it through computer, but simple "push start" for demo

• Investors were "blown away" - same reaction Travis had when he first saw it

• "I couldn't believe what I was seeing"

[107:00 - 114:00] Building Brava: Milestones & Memories

• First units arriving from manufacturer - team cracked champagne

• Fire engine alarm/siren for every sale that came in

• Launched with meal kits to ensure perfect first experience

• "The best meal kits the market has ever seen - also the most expensive"

• Multiple meal kit partners folded - had to pivot repeatedly

• Eventually got out of meal kit business entirely

• Started with ~100 recipes in 2018, now over 9,000 recipes

[114:00 - 120:00] How All Experience Compounds

• Question: Does everything feel like it led to this moment?

• "Without those previous experiences, I don't know if I would've succeeded"

• Restaurant experience: necessary to run a team of chefs

• Standards of excellence from restaurant industry

• "We can accomplish the impossible if we work together"

• People initially worried he was overqualified at Williams-Sonoma

• "They had to kick me out at night - I wasn't used to working only eight hours"

[120:00 - 126:00] The White Belt Mentality

• Surrounded by experts in mechanical engineering, electrical engineering, physics, software

• "The beginner, the white belt mentality"

• "I don't want to say least qualified, but feeling like I had something to prove"

• Expectation of excellence felt familiar from restaurant world

• "I didn't want to fail"

• Started jujitsu a year ago - actually a white belt now

• Assistant coaches for his kids' jujitsu

[126:00 - 132:00] Major Milestones at Brava

• Launching the product in 2018

• Brava Glass launch in 2023 (five years after initial launch)

• Original had metal door due to flickering lamps

• Software change made glass door possible but too late for first version

• December 2024: V3 software update for accessibility

• Partnered with San Francisco Lighthouse

• Screen readers allow blind and low-vision users to navigate app

• Can cook steaks and grilled cheese independently

[132:00 - 138:00] Explaining the Technology

• Cooks with infrared light using lamps designed for solar industry

• Lamps can melt metal in seconds

• Go from ambient to full power in less than one second

• Over 4,000 degrees Fahrenheit at core of bulb

• "Same power delivery as 900-degree wood-fired pizza oven"

• Software controls pulsing: brings surface temp up, cools off, pulses again

• Like a chef moving food in and out of a wood-fired oven

• "Same energy as what comes off the sun - just focused and precision-controlled"

[138:00 - 142:00] Health & Safety Questions

• Not using microwaves or magnetrons

• Uses visible and invisible spectrum of infrared light

• "Same energy that comes off the sun"

• "Same things humans have been cooking with since we started - fire"

• Just more focused and intense

• No strange waves being generated

• Common question: "It sounds too good to be true"

[142:00 - 147:00] Who Is Brava For?

• Hardest question to answer: "Who's your target market?"

• Answer: "People who like to cook at home"

• No specific age demographic

• Initially thought it would be for people who don't want to cook

• Realized: "You're not gonna get somebody to cook that doesn't like cooking"

• Core customer already enjoys cooking

• Tend to be tech-savvy early adopters

• Quality keeps them coming back

• Over 13 million times the start button has been pushed

[147:00 - 152:00] Lessons on Iteration & Growth

• "Don't try and eat the whole cake all at once"

• Launched with 100 recipes in 2018

• If told they'd need 9,000 recipes by 2025: "I might've said that's not possible"

• IoT product can be updated continuously

• "We didn't get everything right out of the gate"

• Finding what you're good at that others find difficult

• Being willing to pivot through challenges

[152:00 - 157:00] The Underbelly of Every Passion

• Honeymoon in Thailand - envied scuba diving instructors

• "These guys have made it - best life"

• Then heard them bickering about internal politics

• "Oh my God, it's here too. It's in everything"

• Find which challenges you can tolerate

• "Turn the challenge into something you can make good on"

• Passionate about cooking but didn't want to cook 14 hours a day

[157:00 - 162:00] Mental Health & Physical Fitness

• Weight training for 17 years

• Jujitsu for past year

• "The weights don't lie, just like the mats don't lie"

• Weaknesses come out quickly - it's humbling

• At 47, dealing with tweaks and injuries - "willing to start over again"

• Walking: didn't start until the pandemic

• Morning walks before work replaced commute podcast time

• "Low dose cardio but it adds up"

[162:00 - 165:00] The Power of Walking

• Biggest mental health lever you can pull

• "Go for a walk even if it's 10 minutes"

• "Exercise snacks" - walk after every meal

• "It adds up through the day and you end up feeling a lot better"

• Clears your head when stuck on a problem

• Come back with fresh perspective and fresh attitude

[165:00 - 170:00] Book Recommendations

• Meditations by Marcus Aurelius - "a go-to"

• Leo Tolstoy's Calendar of Wisdom - on bedside table

• All of Ryan Holiday's books

• Lives of the Stoics by Ryan Holiday - "great primer"

• Got back into reading during pandemic

• Loves history now (didn't like it in high school)

• Currently reading: A Night to Remember about the Titanic (1955)

• Written by Walter Lord who interviewed 60 survivors

• Extreme Ownership by Jocko Willink

• Atomic Habits by James Clear

[170:00 - 175:00] Why Atomic Habits Resonates

• "The teacher arrives when the student is ready"

• "So much valuable advice in there"

• James Clear's Thursday newsletter is excellent

• James sold 20 million books recently

• Took Stephen Covey 20 years to sell same amount with 7 Habits

• Ryan Holiday makes stoicism accessible

• "Tells stories and it just clicks"

[175:00 - END] Final Career Advice for Young Professionals

Find the intersection of interest and skill

• Not just what you're good at - what are you interested in?

• If there's intersection, it's a signal

• Consider: Is there a career here? Can I make money? Can I make enough?

• Don't let money be the only defining factor

• "I never would've gone to culinary school if I let money decide"

Work for the best and work hard

• Willing to sacrifice early on pays off later

• Go all in once you get the signal

• "Work harder than the people around you"

• "Work harder than you think you can"

Don't give up, but be willing to pivot

• Don't be so stubborn you end up doing something you hate

• Reach out to your network

• "Everybody needs a coach sometimes"

• Coach could be mentor, boss, or even books you read

Never be the wisest person in the room

• "I don't ever want to be the wisest person in the room"

• Prefer to be the beginner even though it's uncomfortable

• Especially important with new tools and AI coming out

• Can make really good things without being an expert

Take risks, especially early

• "You can overanalyze and never do anything"

• Take chances and risks early when you can afford lower pay

• "Don't be afraid to take risks later in life either"

• Without risk, the meaning won't be as rich

• Need "skin in the game" for work to be meaningful

#126 Sahand Dilmaghani: Everything is Solvable - Building Terra Kaffe Against All Odds

Sahand Dilmaghani is the founder and CEO of Terra Kaffe, a design-led coffee company reimagining the home espresso experience. Frustrated by the limitations of pod-based machines and the outdated technology dominating the super-automatic espresso category, Sahand set out to build something better—a beautifully designed, app-connected espresso machine that delivers café-quality coffee at the push of a button. What started with him walking the streets of SoHo with two prototypes and eating one meal a day to conserve cash has grown into a company serving tens of thousands of customers who demanded more from their daily coffee ritual. With a background spanning finance, hardware, and design, and fluency in Chinese that took him from Saturday school as a kid to manufacturing facilities in Shenzhen, Sahand brought a unique perspective to an industry that hadn't innovated in decades. Today, Terra Kaffe's machines—from the flagship TK-02 to the compact Demi—represent what happens when you refuse to accept the status quo and build with relentless attention to detail.

In this episode, you'll learn:

• How Sahand's parents' immigrant journey shaped his "everything is solvable" mentality and entrepreneurial grit

• The moment he realized the espresso machine industry was ripe for disruption—and why DeLonghi's executives completely missed it

• Why the best ideas get a 50/50 reaction—half your friends think you're crazy, half think it's brilliant—and why that's exactly where you want to be

• How to navigate the hundreds of daily decisions that can make or break your business without letting perfect become the enemy of done

• The critical difference between asking "should I do this?" versus "can I do this?"—and why it defines your entire career trajectory

Check out Terra Kaffe here: https://www.terrakaffe.com

SHOW NOTES:

[00:00 - 08:30] Parents' Influence & Early Lessons

• Both parents are architects who immigrated from Iran in the 1970s

• Mom's elevator pitch story: How persistence landed her first architecture job

• Learning "everything is solvable" from watching parents navigate challenges as immigrants

• Growing up surrounded by design books and fine arts

• The influence of attention to detail and design thinking from a young age

• No "participation trophy energy"—high expectations with full support

[08:30 - 15:45] Education & Athletic Background

• Studying finance, IT, and Chinese in college

• Starting Chinese school at age 10—being the only non-Chinese kid in class

• Working at PwC in China during summer internship

• Wrestling all four years of high school—lessons in grit and leadership

• Mom convincing him to try rowing for one season—became state champs

• The difference between good coaches and bad coaches

• How sports taught resilience and teamwork

[15:45 - 22:00] First Entrepreneurial Ventures

• Starting an Ultimate Frisbee summer camp at age 16

• Key lesson: The power of authentic community connections

• Attempting to start a wind farm at 18 (couldn't get $10M funding)

• Early understanding that relationships are competitive advantages

• Getting local Greek grill to sponsor jerseys through genuine connections

[22:00 - 30:15] The Terra Kaffe Origin Story

• Working in electric vehicles, using pod machines, getting frustrated

• Realizing the super-automatic espresso category was stuck in the past

• Shopping at Bed Bath & Beyond and Williams-Sonoma—seeing only 3-4 outdated brands

• All machines using "Game Boy Color level technology" in 2017

• Buying used $5,000 machines on Facebook Marketplace to do teardowns

• Understanding he had the perfect background: hardware experience, finance knowledge, love of design

[30:15 - 38:00] Early Days & Validation

• The 50/50 rule: Half his friends thought it was brilliant, half thought he was crazy

• Recording people's complaints about their Nespresso machines

• Going from $100K in savings down to last $2,000

• Eating one meal a day for 18 months to save money for the company

• Walking the streets of SoHo knocking on retail stores with two prototypes

• Getting partnership with Equinox for early events

[38:00 - 45:30] Manufacturing Challenges

• Manufacturer calling: "I thought Americans have money"

• Negotiating minimum order quantity from 300 to 150 units

• Couldn't afford 30% deposit on 150 units

• Building first website on WooCommerce with a friend

• Getting into an accelerator for first $100K check

• Monthly investor updates since inception—building relationships before having investors

[45:30 - 52:00] The DeLonghi Meeting

• Meeting with DeLonghi executive team early on

• Their response: "So you're building a nicer Instagram?"

• Engineers begging Sahand for jobs at €800/month

• Five middle managers for every engineer—no innovation happening

• Realizing he was dealing with a "sleepy incumbent"

• Classic disruption story playing out in real-time

[52:00 - 58:45] Building the Team

• First hire was a designer in Germany—design-led organization from day one

• The importance of the first seven hires—"people you could summit Everest with"

• Everyone being "all in" during scrappy early days

• Deep authentic relationships that last beyond working together

• No autopilot rule: Encouraging disagreement and healthy debate

• Why yes-men and yes-women don't help companies grow

[58:45 - 1:06:00] Product Development & Customer Feedback

• Learning from TK-01 to create the TK-02

• Opening first freight container in Greenpoint—"the story really starts here"

• The goosebump moments throughout the creative process

• 48% of customers coming from pod-based machines

• Creating TK Vote page for customers to upvote features

• Alexa integration being #1 requested feature—87% adoption rate

[1:06:00 - 1:12:30] Creating the Demi

• Realizing size really matters—many people couldn't dedicate counter space

• Some customers didn't need milk frothing capabilities

• Making a compact version with all the same design principles

• Listening to community feedback to create better product options

• Phone calls and surveys to understand real pain points

[1:12:30 - 1:19:15] Biggest Challenges

• Not letting perfect be the enemy of good or done

• Making hundreds of decisions daily that could make or break the business

• Balancing financial constraints with product excellence

• Examples: Should you spend $60K on bus shelters or $500K on full campaign?

• Understanding the 80/20 rule in product and marketing decisions

• Playing the long game vs. short-term wins

[1:19:15 - 1:24:00] Personal Well-being & Balance

• Athletics as the last thing to drop—a warning sign if not exercising

• Basketball, gym, tennis for physical health

• Music as a huge part of life—favorite album is Sirens by Nicolas Jaar

• Going to vinyl shops and art galleries

• Forming deepest connections over music

• Importance of developing your own taste in art

[1:24:00 - 1:30:45] Sacrifice & Career Success

• Life is a game of trade-offs and priorities

• Sacrifice is unavoidable when building something meaningful

• Can't do half measures—side hustle must become main hustle

• Banking days: "Weddings, funerals—these are the things you miss"

• Working German lessons 6:30-9:30 AM, then full workday, then homework

• Luck + hard work = success

[1:30:45 - 1:35:30] Proudest Moments

• First freight container of TK-02s arriving in Greenpoint

• Seeing first sketches—goosebump moments

• Visiting factory for first production run

• Best compliment: "If I had to describe it in one word: thoughtful"

• Knowing the discretion and decision-making that went into every detail

[1:35:30 - 1:40:00] Career Advice for Young Professionals

• No autopilot—be curious, get your hands dirty

• You'll discover what you don't like before what you do

• The difference between "should I do this?" vs. "can I do this?"

• Leaning forward shows eagerness and builds trust

• Being unapologetic about wanting to take on responsibility

• Book recommendation: The Rise of Theodore Roosevelt—intellectual curiosity matters

[1:40:00 - End] Closing

• How Sahand takes his coffee: double shot espresso or drip to nurse longer

• Final reflections on the journey

KEY QUOTES:

• "Everything is solvable—you just have to approach it with that mindset"

• "If everyone thinks you're crazy, you might be. If everyone loves it, it's already been done. 50/50 is perfect."

• "Weddings, funerals—these are the things you miss when you're a banker"

• "There's a powerful difference between 'should I do this?' and 'can I do this?'"

• "No autopilot. If you're not willing to disagree, why are you even here?"

#125 Dan Stein: Career Truths Nobody Tells You

Dan Stein is a former recruiter at Google, SnapChat, and the VC firm A16Z. His wellness journey was featured in Men's Health and he launched an athletic apparel brand focused on mental health called Pax. Dan has also visited over 30 countries.

In this episode we discuss:

-The best career advice from a recruiter's perspective

-Why money is a renewable resource, advice from his dad that has helped him take more calculated risks

-How a cross-country move and a chance encounter with a waitress helped him land a job at Google

-Why "being seen" matters more than the perfect resume

-Why your manager can make or break your career

-The most important life lesson from visiting 31 countries

-What he means by 'finding what works for you' around health & fitness and more

Follow Dan on LinkedIn

Check out Pax’s website

Time-Stamped Show Notes

[00:00 - 08:30] Growing Up with Service-Minded Parents

• Dan's mother: special needs teacher with 100% graduation rate

• Dan's father: minister running home fellowships in Wisconsin

• The "lead with love" philosophy that shaped Dan's worldview

• Unconventional church experience and freedom of choice growing up

[08:30 - 15:45] Life Lessons from Dad

• "Pay for good parking" - why convenience matters

• "Money is a renewable resource" - eliminating financial anxiety

• How faith informed the family's approach to money and provision

• Growing up without extravagance but always having needs met

[15:45 - 20:30] Family Dynamics

• Being second of four siblings

• The only non-parent in the family

• How being single allowed for more risk-taking and spontaneity

• Career-driven vs. family-focused life paths

[20:30 - 35:15] The College Years: Battling Anorexia

• First year at University of Minnesota: everything seemed fine

• Sophomore year: when the eating disorder took over

• 0.9 GPA and academic probation

• The obsession: 6-7 hours daily in the gym, waking at 2 AM for cardio

• Skipping classes to work out, severe food restriction

• Moving home and swallowing pride to attend community college

[35:15 - 47:20] The Darkest Period & Path to Recovery

• Working odd jobs: window washing, waiting tables, painting

• Hiding the disorder, eating alone in his room

• The pasta ritual: sucking off marinara sauce, spitting out pasta

• Rock bottom in Georgia: freezing in summer heat, lips and nails blue

• Doctor's intervention: "I think you have an eating disorder"

• Weighing 132 pounds at 5'10"

• The 21 signs of starvation (he had 20 of 21)

• One failed therapy session in 2005

• Choosing self-education: fitness magazines, medical journals, nutrition books

• 4-5 years to full recovery in his mid-to-late twenties

[47:20 - 52:45] Men's Health Feature & Going Public

• 2016: Submitting to Ultimate Men's Health Contest

• The "How I Got Healthy" video series

• Video crew at Gold's Gym Venice at 6 AM

• Over 1 million views - 3x more than any other video

• Almost making the cover (Michael B. Jordan got it instead)

• "Me and Michael B. Jordan are in the same issue"

• The lesson: people are more compassionate than we expect

• 90% supportive comments vs. 10% negativity

[52:45 - 01:02:30] Breaking Into Sports: The Milwaukee to Oakland Journey

• Dream of becoming a baseball GM

• Reading John Schuerholz's book about the Atlanta Braves dynasty

• Realizing the grind wasn't for him

• Cold calling every MLB team's director of sales

• Billy Fries responds: 9 months at $9/hour in a utility closet

• Leading the sales board at Milwaukee Brewers

• Job interviews: Charlotte Bobcats, Cleveland Cavaliers

• Taking Oakland A's job over the phone, sight unseen

• $24,000 salary (harsh Bay Area reality)

• Cross-country drive with his dad

[01:02:30 - 01:08:45] The Raiders & Meeting Al Davis

• Getting laid go by the A's the day after Opening Day (seasonality lesson)

• Dad's advice: "Give it three weeks"

• Landing Raiders job within two weeks

• Meeting Al Davis coming out of the bathroom

• The famous Lane Kiffin press conference

• Al Davis passing away - phones ringing with fan stories

• The outpouring of love for a maverick owner

• Seeing John Madden at practice and around the facility

[01:08:45 - 01:15:30] The Google Break: A Serendipitous Connection

• Meeting Allie, the waitress at a Minnesota Gophers bar in San Francisco

• Getting her number, getting ghosted

• 3.5-4 years later: Facebook message about a Google sales job

• "What do you know about Google?" "You guys got the search engine"

• Seeing the campus paradise: people on lawns, free food, cafes

• Job offer on the drive home from the interview

• Starting on Google Offers (Google's Groupon competitor)

• Team gets laid off after 6-7 months

• Moving to AdWords new business sales

[01:15:30 - 01:22:15] Making the Pivot: Sales to Recruiting

• 4-5 years in sales, feeling the quota climb fatigue

• Not growing professionally, losing motivation

• Browsing internal job board: Project Aura (Google Glass evolution)

• Lunch with Jose: treating it as conversation, not interview

• Not trying to impress, just learning about recruiting

• Job offer while at the Arnold Fitness Expo

• 12 years in recruiting since that pivot

[01:22:15 - 01:30:45] Job Market Reality Check

• Agreeing the job market is incredibly challenging

• The problem: too many bad recruiters as gatekeepers

• AI bots reviewing resumes for keywords

• From 200-300 applications per week to 1,200-1,500 in 2-3 days

• The key: YOU HAVE TO BE SEEN

• Tactical advice: Find people on LinkedIn in the department

• Send connection requests, ask about their experience

• End with: "Can you pass my resume to the hiring manager?"

• The importance of preparation (referencing the Blackberry story)

• Knowing your opponent: research the company, market, history

[01:30:45 - 01:35:20] The Preparation That Wins Jobs

• Story of two final candidates at a multi-billion dollar company

• Winner: came in with more market information than the CEO knew

• Showed the future, not just past accomplishments

• Preparation differentiates you from other qualified candidates

[01:35:20 - 01:40:30] Salary Negotiation in the Age of Transparency

• Negotiation has changed: you're not negotiating with a person, but with the internet

• Pay transparency laws have leveled the playing field

• Advice #1: Be realistic with your ask

• Don't ask for $300K when offered $200K

• Advice #2: Only negotiate when ready to accept

• Say: "I want this job. If you meet me at X, I'll sign today"

• Makes it easier for them to get approval internally

[01:40:30 - 01:45:15] Greatest Google Memories

• Professionally: the brilliance of people

• Onboarding circle: Stanford, Stanford, Cal, Harvard, MIT... "University of Wisconsin Milwaukee"

• Learning from the smartest people on the planet

• Personally: first company holiday party at SF MoMA

• Black tie event with penguins wandering around

• Caviar, fine wines, champagne

• Eating sushi in front of the fish tank

• Coming from Raiders parties at the facility

[01:45:15 - 01:52:30] Working with Founders at Andreessen Horowitz

• Job: partnering with seed-stage founders

• Often just founder and co-founder, no other employees

• Two key competencies of great founders:

  1. Coachability - open to feedback and coaching

  2. Hire experts and let them be experts - don't micromanage their expertise

• The design example: if you're not a designer, don't critique design

• Lean on your network for assessments

• Critical insight: first hires determine success more than founders

• Don't half-ass early hires or rush them

[01:52:30 - 02:00:45] Building PACS Activewear

• 15-16 years passionate about health and wellness post-recovery

• Started researching 3 years ago with friend Aaron (met at gym)

• Both used gym to manage mental health

• Noticed gap: no activewear brand connecting mental and physical health

• February 2023: got logo back (first milestone)

• May 2024: official launch (almost 2 years)

• Self-funded, no investors, no marketing team

• Does all shipping from storage locker himself

• "A success because of the people I've met, not financially"

• Current focus: selling existing inventory and brand message

[02:00:45 - 02:05:30] The Hardest Part of Entrepreneurship

• Biggest struggle: social media and branding

• Doesn't enjoy being active on Instagram/TikTok

• Yet that's where small niche brands must live

• Lack of motivation for 30-45 minutes creating perfect reels

• This year's commitment: more posting, more focus on brand message

• Regret: not leaning into being the living embodiment of the brand

• Uncomfortable talking into phone and posting videos

• Working to overcome that discomfort

[02:05:30 - 02:15:45] Dan's Wellness Philosophy

• Core principle: Find what works for YOU

• No universal approach to health and wellness

• It took years to figure out what works for his body

• Patience is key - not overnight, not even 30 days

• 30-day challenges often do more harm than good

• People quit when they don't see expected results

• Progress is lots of little steps, not large leaps

• Celebrate small wins

• Don't let fitness restrict your ability to live and be social

[02:15:45 - 02:22:00] A Day in Dan's Life

• Wakes at 5:45 AM (used to be 4:45-5:00 AM)

• Lives 25 seconds from his gym

• Morning routine: devotional, Bible, pre-workout

• 75-90 minutes lifting (focused, not chatting)

• Plus cardio: 90 minutes to 2 hours total

• Aims for 8 hours sleep (never sleeps through the night)

• Wakes 2-4 times per night but falls back asleep quickly

• Screens off 15 minutes before bed

• Prays every night before sleep

• Never had a TV in bedroom

[02:22:00 - 02:28:15] Nutrition & Eating Philosophy

• Doesn't eat until midday (around noon or 1 PM)

• First meal: egg whites, chicken breast, brown rice, sweet potatoes, oatmeal, berries

• Dinner: rotating protein (steak, shrimp, fish), vegetables, healthy carbs

• 80/20 rule: 80% clean/healthy, 20% whatever

• Loves cooking as a way to unwind after work

• 3,500-4,000 calories per day

• Goes out with friends without restriction

• Always orders dressing on the side

• Dinner by 5:30-6:00 PM (won't do 9:30 PM dinners)

• Evening snack before bed

[02:28:15 - 02:32:30] Supplements & Sleep Support

• Started GABA 2-3 years ago for sleep

• Able to fall back asleep quickly

• Standard supplements: creatine, BCAAs, CLA (conjugated linoleic acid), glutamine

• Recently: NAD+ peptide and TB-500 for muscle injuries

• TB-500 helped forearm injury

• NAD+ eliminated afternoon mental fog/wall

• Unsure if creatine/pre-workout is placebo, but feels better when taking it

• Coffee connoisseur, multiple cups daily (none after 1 PM)

[02:32:30 - 02:36:45] Typical Meals & Snacks

• Baby carrots: could eat 3 bags a day

• Cottage cheese (slow-digesting casein protein)

• Lesser Evil popcorn (favorite before-bed snack)

• Recently: protein waffles (nostalgic for childhood Eggos)

• Tried Kodiak (tasted like cardboard)

• Settled on Eggo protein waffles

• Swore off protein powders years ago (wreaked havoc on stomach)

• Tried all types: whey, casein, pea, soy, beef

• Chose whole food proteins instead: chicken, fish, eggs, yogurt

[02:36:45 - 02:40:30] Intermittent Fasting Experience

• Tried eating only 3 PM - 8 PM for 6 months

• Eats 3,500-4,000 calories daily

• Dinner could be 2,000 calories

• No indigestion issues or fat storage noticed

• But also no massive energy boost

• Didn't work for him, but great if it works for others

• Key: unlock what works and stick with it

[02:40:30 - 02:45:15] Workout Philosophy & Routine

• Started following magazine routines (Men's Health)

• Now creates own routines, switches every 2-3 months

• Doesn't require massive changes - minor tweaks work

• Change rep ranges, grips, barbell to dumbbell

• Keep body in confusion to force adaptation

• Body is incredibly efficient - must trick it to change

• If doing same thing repeatedly, body builds just enough muscle to sustain

• Confusion forces body to build more muscle to survive

[02:45:15 - 02:48:30] Rapid Fire: What He Knows Now at 43

• Wish he knew at 35: It's okay to still be single

• Midwest pressure: married by 25 or something's wrong

• At 35: no marriage, no house, no kids - "what went wrong?"

• Now 43: still no kids, never married, has house (doesn't live in it)

• Everyone's timing is different

• No universal timeline despite what society tells us

[02:48:30 - 02:55:45] The Hardest Loss: His Dog

• Put dog down Christmas morning last year

• Only dog that was truly "his dog"

• His life companion as someone never married

• Cried in car for 45 minutes

• Lost dad earlier same year

• Cried more for dog than dad (felt guilty about this)

• Research: love with dogs accesses different part of brain

• Dogs provide truly unconditional love

• Over a year later, still gets emotional

• Corgi in coffee shop triggered him recently

• First time experiencing real grief at 42

[02:55:45 - 02:59:00] Processing Grief

• Lost two very important beings in same year

• Time helps, but grief isn't linear

• Focus on positive memories

• It's okay to cry in public

• Broke down on StairMaster when Eric Clapton's "My Father's Eyes" played

• Dad's favorite musician

• Didn't get embarrassed, just let it happen

• Found it cleansing

[02:59:00 - 03:01:30] Book Recommendation

• The Giving Tree by Shel Silverstein

• Parents introduced it at age 7-8

• Story of tree's relationship with kid as he grows

• Tree gives everything: branches, fruit, trunk

• Ends as just a stump

• Kid returns as old man needing place to sit

• Tree offers the stump

• Lesson: no matter how much you give, there's always something more you can give

• Green cover with bright red apple

[03:01:30 - 03:04:45] Current Favorite Show

• Landman (Paramount+) starring Billy Bob Thornton

• From Taylor Sheridan (creator of Yellowstone)

• Reminds him of Friday Night Lights (favorite formative show)

• Focuses on average everyday American life

• Not sensationalized with violence/drugs/sex

• Well-written character relationships

• Moments remind him of his family and siblings

• Less about overarching story, more about characters

[03:04:45 - 03:12:00] Career Advice: Three Key Principles

1. Trust Your Direct Manager

• Most important factor when choosing a job

• Manager holds many cards for your success

• Will they have your best interest at heart?

• Will they fight for you with upper management?

• Or are they using you as means to their advancement?

• Bad managers climb ladder on backs of others

• More important than compensation (all else equal)

• You're working to make some billionaire richer anyway

2. It's Okay Not to Love Your Job

• Don't need to wake up excited every morning

• Society says quit if you don't love it

• Not everyone needs to be passionate about their work

• Some people just "get to 5 PM"

• But still give it your all, even if you don't love it

• Not loving your job doesn't mean quit tomorrow

• Commit to giving your best every single day

3. Don't Get Caught Up in Office Politics

• Mind-numbing and exhausting

• Will exist in most places (fact of life in American capitalism)

• Don't let your career define who you are

• US obsession: "What do you do?" is first question to strangers

• Travel abroad: people rarely ask about your job

• For Dan: doesn't want to be known as "a recruiter"

• But if career defines you, that's also fine - personal choice

[03:12:00 - 03:15:30] Travel Wisdom: Happiness with Less

• Most life lessons from travel: seeing happiness with so little

• Story from Zimbabwe safari

• Guide Claude: never left his village beyond 20 miles

• Been to 3 countries only because borders merge in Victoria Falls

• Never on plane or train

• Couldn't be happier

• "Best office in the world"

• Lesson: happiest people often have very few material belongings

• What matters: being around people they care about, simplicity of life

• US materialism vs. global perspective

[03:15:30 - 03:17:00] Closing Thoughts

• Importance of preparation in tough job market

• Stand out by being 10x more prepared

• Do reflection on what's important to you

• Over-prepare for every situation

• Deep gratitude for the conversation

#124 Josh Pankow: Becoming Indispensable

My guest today is Josh Panko, President of Leaf Trading Cards. Josh's journey in the sports card industry started at age seven when he opened a card shop in his basement. That childhood passion turned into a remarkable career that's taken him from working at card shops as a teenager, to Upper Deck's product development team, to now leading one of the most creative trading card companies in the industry.

What I love about Josh's story is how he built his career by working every angle of the business—retail, distribution, manufacturing, customer service. He learned the entire supply chain, which gave him a perspective that few in the industry have. And today, at Leaf, he's creating some of the most innovative products in the space, from on-card autographs of Hollywood legends like Al Pacino and Clint Eastwood, to unique sports card concepts that major licensed manufacturers can't touch.

This conversation is packed with wisdom on hard work, taking initiative, building relationships, and staying humble even as you climb the ladder. Whether you're in the trading card world or not, Josh's lessons on career development and leadership are gold.

In this episode we discuss:

• Why working every level of your industry early in your career creates an unfair advantage - and how Josh's experience in retail, distribution, and manufacturing shaped his leadership at Leaf

• The handwritten letter strategy that landed Josh his dream job at Upper Deck - and why his father's unconventional advice to FedEx overnight it to the CEO actually worked

• How being kind to everyone (especially people outside your department) can fast-track your career - Josh's finance department friendships got his projects prioritized over senior colleagues

• Why Josh would rather employees take initiative and make mistakes than wait for permission - and the Shawshank Redemption lesson about not asking to go to the bathroom

• The "harder you work, the luckier you get" philosophy - and how Josh turned clocking out at 5pm then returning to work unpaid into career-defining opportunities

SHOW NOTES

[00:00] Introduction

• Josh's journey from 7-year-old card shop owner to President of Leaf Trading Cards

[02:15] The Origin Story

• Opening a card shop in his basement at age seven

• Weekly trips to the card shop with his mom during grocery runs at Winn-Dixie

• The 1989 Upper Deck Ken Griffey Jr. card that changed everything

• Getting a $5 allowance and learning to wheel and deal

[08:30] Early Business Lessons

• Setting his own prices without Beckett guides

• Understanding supply and demand as a kid

• How his sales-oriented dad influenced his entrepreneurial spirit

• Working neighborhood card shows and building inventory

[15:45] The Philosophy of Pricing and Value

• Why modern pricing comps are still arbitrary

• Comparing card pricing to buying a house

• Advice for buying cards: focus on what you want, not speculation

• The safety of eBay's authentication process

[22:10] The Grading Game

• When Josh first encountered card grading in the early 2000s

• The shift from Beckett to PSA dominance

• Why a PSA 10 isn't necessarily "harder" than other 10s

• The conflict of interest in Fanatics owning grading companies

• When vintage cards justify premium grading costs vs. modern cards

[35:20] Family and Work Ethic

• How his parents shaped his approach to work

• His dad selling baby diapers and being a natural salesman

• Mom as a stay-at-home Cubs fan

• Teaching his own kids (ages 6 and 10) to appreciate hard work

• Fighting against instant gratification culture

[42:00] The LeBron James Standard

• Why LeBron arriving 10 hours before games matters

• The compounding effect of consistent effort over 20 years

• How God-given talent still requires incredible work ethic

• Durability and longevity in any profession

[48:30] Getting the Upper Deck Job

• His dad's unconventional advice: handwrite a letter and FedEx it overnight

• Why the letter strategy worked when online applications wouldn't

• The 8-month hiring process from January to August

• Starting in product development and learning the business

[54:15] Working at Upper Deck

• Clocking out at 5pm then going back to work unpaid

• Choosing learning and experience over overtime pay

• Helping every department to understand the full business

• Making himself invaluable across the company

• Building relationships with finance, acquisitions, and customer service

[01:02:00] The Move Back to Atlanta

• Leaving Upper Deck after a year to open his own card shop

• The smooth departure and maintaining relationships

• Running an eBay business from his college apartment

• Having UPS pickup from his apartment building

• Working every angle: retail, distribution, wholesale, manufacturing

[01:08:45] Understanding the Full Supply Chain

• Why working at all levels gave him an unfair advantage

• The distributor role most people don't know exists

• How distributors buy bulk and take financial risk

• Why they're the wealthiest (and most invisible) people in the industry

• Learning from the customer service side and the manufacturing side

[01:15:30] The Path to Leaf Trading Cards

• Knowing the previous owner and doing consulting work

• Starting at Razor Entertainment in 2006

• Becoming President about two years ago

• Why he loves the creative manufacturing side

• Watching the French Open as part of his job

[01:20:00] Lessons from Upper Deck Applied at Leaf

• Getting his hands in everything, not staying in his lane

• The two mentalities: "I'm not paid enough so I won't do extra" vs. "I'm not paid enough so I need to show what I can do"

• Understanding finance, acquisitions, customer service, and design

• Making yourself invaluable while staying humble

• His dad's reminder: "No one is irreplaceable" - even Steve Jobs

[01:28:15] The Secret Sauce at Leaf

• Creativity and innovation without league licenses

• Creating cards that Fanatics and Panini can't make

• The Patrick Mahomes + Lionel Messi + Aaron Judge triple autograph

• Keeping products affordable ($125-$200 boxes vs. $1,000+)

• Hand-collating every single box for consistent value

[01:33:45] Greg Cohen: The Product Mastermind

• How his former Upper Deck colleague became Leaf's head of product development

• Greg's incredible creativity and humble nature

• The "Pieces of the Past" shadow box cards

• Moment cards: The George Brett Pine Tar incident with Goose Gossage

• Creating unique inscriptions and concepts that stand out

[01:40:20] Pop Culture Cards

• The product Josh is most proud of

• Autographs from Margot Robbie, Clint Eastwood, Al Pacino, Robert De Niro

• Dwayne "The Rock" Johnson wardrobe swatches

• Back to the Future cast autographs

• Working Dallas Fan Expo to get Michael J. Fox, Huey Lewis, and Star Wars cast

• Creating something truly unique with no competition

[01:48:00] The Power of Being Nice

• Why treating people with respect goes so far

• Building relationships with agents, players, and vendors

• The company motto: everyone represents Leaf at shows

• Firing people with dignity and respect

• Sending employees home early on Fridays as a small gesture

• Supporting employees through family emergencies

[01:55:30] Career Advice for Young People

• Show up on time (no Starbucks excuse)

• Be nice and respectful to everyone

• Take initiative without waiting for permission

• The Shawshank Redemption bathroom analogy

• Don't be afraid to make mistakes - just take responsibility

• Don't take credit for wins if you won't take responsibility for losses

• Athletes who play "not to get injured" get injured - same with work

[02:02:00] Final Thoughts

• Put in the work early so you have freedom later

• The harder you work, the luckier you get

• Why instant gratification is killing work ethic

• Teaching the next generation to appreciate effort

#123 Kendall Berg: Secrets of the Career Game

Kendall Berg is a career strategist and author of Secrets of the Career Game who helps ambitious professionals navigate corporate politics with integrity and transform strong performance into visible, undeniable value. After being told early in her career that "everybody loves having you on their team, but nobody likes working with you," she dedicated herself to learning the unspoken rules of advancement—and was promoted five times in six years. Now, through her coaching practice and her tactical, no-nonsense approach, Kendall teaches thousands of clients across 27 countries how to earn more, advance faster, and feel in control of their career trajectory without burning out or losing themselves in the process.

In this episode, you'll discover:

• Why your boss has NO idea what you're actually doing—and the weekly habit that fixes this blind spot

• The one person you must talk to during interviews that reveals the REAL company culture (hint: it's not the hiring manager)

• How asking for help makes people think MORE highly of you—the counterintuitive psychology that changes everything

• The "influencer list" strategy: Why you're networking with the wrong people and how to identify the 5 who actually control your career

• Why 82% of jobs are filled before they ever hit the job board—and what to do about it

Time-Stamped Show Notes

[00:00] Introduction & Book Feedback

• Initial response to Secrets of the Career Game

• Why the book is written as a tactical textbook, not theory

• The importance of actionable advice readers can implement immediately

[03:15] Interviews That Stand Out

• Discussing the unspoken rules and corporate politics

• Navigating interpersonal conflict and toxic coworkers

• The mental load of difficult workplace relationships

• When survival mode is the only option

[07:30] Kendall's Origin Story

• Growing up with a tech sales father who made her do business cases for everything

• Learning to communicate ROI from childhood

• Studying mathematics and economics

• Starting career as a data scientist and analyst

• The skill that mattered most: communication

[12:45] Lessons from Parents

• Mom's philosophy: "You might as well try it"

• Getting out of your own way

• Failure as the start of something new, not the end

• Starting businesses early and learning from failure

• The importance of persistence over perfection

[17:20] Moving 20+ Times Before High School

• Attending four elementary schools, two middle schools, two high schools

• All within a 5-8 mile radius

• How constant change built adaptability

• Learning to build relationships quickly

• The one move Kendall requested herself

[22:40] The Inflection Point to Career Coaching

• The VP who told her: "Everybody loves having you on their team, but nobody likes working with you"

• Choosing growth over defensiveness

• Meeting with female mentor Allison

• The transformative advice: spend 2-3 minutes on small talk

• Getting promoted 5 times in 6 years

[28:15] The CFO Job She Turned Down

• Being offered a CFO position at 29, six weeks after having her daughter

• Why her "dream job" was actually misaligned

• Understanding the difference between title and fulfillment

• The importance of self-assessment before accepting roles

• When they referenced her age in the offer

[34:00] How to Do Due Diligence on a New Job

• The power of talking to a peer, not just the hiring manager

• What to ask: promotion timelines, mistake handling, mentorship

• Why peers have no incentive to lie to you

• Red flag: when companies refuse peer conversations

• Asking to speak with 8 peers before accepting her current role

[40:30] The Samsung Interview Story

• Four hours of back-to-back interviews

• "I sleep 4-5 hours a night"

• The "crazy range" salary negotiation tactic

• Learning about "dispatchers" who report back to Korea

• Choosing culture fit over compensation

[45:20] Ghost Culture vs. Real Culture

• What executives think culture is (cereal bars, nap pods)

• What employees actually experience day-to-day

• The Google commercial that changed corporate perks

• Why subcultures matter more than company culture

• Your direct manager creates your real experience

[50:45] Building Your Influencer List

• Identifying 20 people who have influence over your career

• Evaluating them on seniority, power, and "fear factor"

• Narrowing down to your top 5

• Meeting with 20 executives quarterly on rotation

• Why most career conversations happen without you in the room

[57:10] The Client Who Got 6 Job Offers

• Three months, 60 coffee chats across 5 target companies

• Meeting everyone from janitors to CEOs

• Nothing happened during the holidays

• February: 6 simultaneous job offers

• The power of relationship-first, application-second

[01:01:30] People Who Help You Think More Fondly of You

• The umbrella analogy

• Why asking for coaching makes others feel invested in you

• Overcoming the fear of "bothering" people

• Most people feel flattered when asked for help

• Breaking the misconception that asking for help is manipulative

[01:06:45] Playing the Career Game with Integrity

• Why "playing the game" gets a bad reputation

• Learning the rules vs. playing by them

• When Kendall chose NOT to falsify financial reports

• Understanding the game lets you opt out intentionally

• Building authentic relationships that benefit both parties

[01:10:20] The Hard Truth: Your Boss Doesn't Know What You're Doing

• The hardest career secret to navigate

• Weekly updates are essential, not optional

• The balance between educating your boss and seeming haughty

• Why visibility matters more than performance alone

[01:12:40] Career Advice for Her 30-Year-Old Self

• "The other person is also right"

• Getting out of victim mentality

• Taking accountability creates emotional distance

• Asking: "What are your expectations for me?"

• Solving problems by understanding others' perspectives

[01:15:25] The Toxic Boss Who Falsified Reports

• Working in finance with ethical dilemmas

• Losing confidence in her own capabilities

• Almost becoming a high school math teacher

• Why she had to live through it to learn from it

• The setback that taught her the career game

[01:19:50] Balancing Career Success and Family

• There's no such thing as work-life balance

• Work and life exist in seasons

• The terrible advice: "You can't have everything as a mother"

• Establishing boundaries vs. maintaining them

• When exceptions become the new boundary

[01:24:30] Trade-Offs and Saying No Constructively

• Presenting alternatives instead of just declining

• "I can't stay late tonight, but I can be on early tomorrow"

• Why most leaders will support your boundaries

• The importance of communicating trade-offs

[01:27:15] Self-Care: Paint by Numbers

• Finding zone-out activities that work for you

• Mother-daughter creative time

• Numbers-based creativity for analytical minds

[01:29:00] Book Recommendations

• Seven Habits of Highly Effective People (reads annually)

• Unspoken Truths for Career Success by Tessa White

• How to Win Friends and Influence People (reread this year)

• The Sword of Truth series (the reason she got married)

• Favorite habit: Listen first and seek to be understood

[01:32:45] Rapid Fire Career Advice

• For someone 5 years into their career

• Relationships first: build them, keep in touch

• Get comfortable with the second-best solution

• If someone else's idea solves the problem, roll with it

• Collaboration over being "right"

[01:35:20] The Nine Box & Final Thoughts

• Every company plots you on a performance chart

• Individual contributors never see it

• Why transparency would help everyone

• The importance of knowing how you're evaluated

• Staying connected beyond the interview

Check out Kendall’s website: www.thatcareercoach.net

#122 Jamie Siminoff: Lessons From Building Ring

Jamie Siminoff is the CEO and founder of Ring, the camera company that transformed home security. While his viral Shark Tank episode didn't yield a deal from the sharks, it launched the video doorbell company. In 2018, Ring sold to Amazon for $1 billion. Jame published a book titled Ding Dong: How Ring Went from Shark Tank Reject to Everyone's Front Door. 

In this episode we discuss: 

-the greatest lessons from his failures
-the 1 question he'd ask James Dyson in an elevator
-why often the most important decisions are the ones we say "no" to
-how the best thing that never happened was not getting acquired by ADT
-what he learned about the relationship between money and happiness
-the best career advice he ever received
-the nicest thing anyone has ever done for him and more

PODCAST SHOW NOTES:

Key Timestamps

[00:00] Opening & Growing Up in New Jersey

• Jamie's childhood in Chester, New Jersey

• The nature vs. nurture debate on entrepreneurship

• Growing up with freedom and access to tools in the basement

• The "back by dark" generation vs. today's parenting

[03:30] Parenting Philosophy & Life Lessons

• Greatest lesson from Jamie's parents: treating him like an adult

• Letting kids be who they want to be (Oliver's sports photography journey)

• Rejecting college stress and performance pressure

• Supporting children without forcing them into predetermined paths

[07:00] Failure as Learning & The DoorBot Story

• Reframing failures as "learnings"

• How DoorBot (Ring's predecessor) taught valuable lessons despite commercial struggles

• The importance of being public with failures to accelerate learning

• Why perfect products don't exist on day one for true innovations

[10:15] Elevator Questions: Advice for a 25-Year-Old

• Finding what you're passionate about when you're young and responsibility-free

• The difference between a "job" and meaningful work

• Why purpose matters more than paychecks

[11:30] The James Dyson Question

• Jamie's admiration for Dyson as his "mentor I haven't met yet"

• Understanding how Dyson thinks about entering new markets

• The power of authenticity in brand building

• Why Dyson still vacuums his own house

[14:00] Building Authentic Brands

• Why authenticity is the foundation of great brands (Nike, Dyson, Ring)

• The Jersey grit mentality

• You can't buy authenticity—it comes from genuine purpose

[16:45] The Art of Saying No

• Most important decisions are the ones you decline

• Turning down private label deals to maintain customer relationships

• Building long-term value vs. short-term revenue

• The difficulty of saying no when you're desperate

[19:30] Decision-Making Framework

• Being willing to make wrong decisions and course-correct

• Having a clear North Star (Ring's: own the customer relationship + make neighborhoods safer)

• The ADT meeting that never materialized—why it was the best thing that didn't happen

• Why small companies often die when acquired too early

[23:00] Money & Happiness

• Going from zero to significant wealth in 60 days

• Being "all in"—Ring was 100% of Jamie's net worth

• Borrowing money for the closing party after signing with Amazon

• Why money's impact is temporary but purpose endures

• What truly motivates people to stay at companies for 15 years

[27:30] Looking Ahead: Fatherhood in 10 Years

• Hopes for relationship with Oliver at age 27

• Supporting children to fully achieve what they want for themselves

• Staying best friends and traveling together

[28:30] Best Career Advice Ever Received

• Be very careful with advice—everyone is unique like a fingerprint

• Listen and learn from everyone, but filter through your own lens

• Advice from one person's perspective doesn't automatically apply to yours

[30:00] Wisdom from Age 40 to Now

• Wish he understood investing and compounding earlier

• The power of the S&P 500 and long-term wealth building

• Brad Gerstner's Invest America initiative (teaching kids to invest)

• It's harder to keep money than make money

[33:00] Acts of Kindness

• Story of a stranger providing an AC unit during a Bay Area heat wave

• Mark Schuster's unwavering support during Ring's darkest moment

• The importance of showing up for people

• Real legacy: how many people say you changed their life

[37:00] Luck vs. Skill: The Lottery Ticket Theory

• Shark Tank as the ultimate lottery ticket (30,000+ applicants)

• Hard work buys you more lottery tickets, but doesn't guarantee winning

• Seeing smart, hardworking people with great ideas not make it

• The phenomena of Ring becoming the largest company ever on Shark Tank

[40:00] Closing Thoughts

• The power of brand awareness and timing

• Resourcefulness as a core trait

• Learning and adjusting on the fly

#121 Patrick Mouratoglou: Building Unshakeable Confidence

Patrick Mouratoglou is one of tennis's most successful and unconventional coaches, known for his work with Serena Williams during her dominant return to form—helping her win 10 Grand Slams and reclaim the world number one ranking. But his journey to the top began in the darkest of places: a childhood marked by crippling shyness, zero self-esteem, and such severe social anxiety that he couldn't make eye contact without fear of vomiting. When his dream of becoming a professional tennis player was crushed at 15, that rock bottom moment became the catalyst for an extraordinary transformation. Today, Patrick coaches the next generation of champions, founded the innovative Ultimate Tennis Showdown (UTS), and has written a book about the "progress zone"—the space where confidence is built through small, daily victories. His approach to coaching is refreshingly transparent in a sport known for secrecy, and his insights on building champions apply far beyond the tennis court.

What You'll Learn in This Episode:

• Why the worst thing that happens to you might be the best thing—how Patrick's devastating rejection at 15 became the turning point that saved his life and launched his coaching career

• The hidden truth about motivation—why players (and people) who seem "unmotivated" are actually protecting their confidence, and what really drives elite performance

• How to rebuild someone's confidence from zero—Patrick's unconventional methods, including secretly rigging matches to create winning streaks and psychological breakthroughs

• What separates champions from great players—the mindset traits of Serena Williams, Roger Federer, and Novak Djokovic that have nothing to do with talent

• The art of hearing what people think, not just what they say—Patrick's most powerful coaching skill and why "the weather is nice" means completely different things in London versus Miami

Show notes:

[00:00] Introduction

• Patrick's background and current work with rising star Holger Rune

• The importance of coaches in sports

[05:30] The Darkest Chapter: Childhood Struggles

• Growing up with severe social anxiety and zero self-esteem

• Being physically sick from stress, unable to make eye contact

• School as a daily nightmare of failure and humiliation

• Tennis court as the only safe space

[12:15] The Turning Point: When Dreams Collapse

• Being denied the chance to pursue professional tennis at age 15

• How devastation became the "kick in the ass" needed to change

• Starting 10 years of therapy while building confidence through action

• The concept of "little victories" and daily progress

[20:45] The Power of Rock Bottom

• Why the worst moments can provide the best opportunities

• Developing empathy and communication skills through isolation

• How early struggles shaped his coaching philosophy

• Learning to put yourself in others' shoes

[28:00] Building Confidence from Zero: The Anna Story

• Coaching a player with no self-esteem

• The unconventional method of secretly rigging matches to build winning streaks

• Why you can't build confidence without victories

• The importance of creativity when you lack traditional coaching tools

[35:20] Coaching Serena Williams: The Reconnection

• Joining Serena after two years without a Grand Slam

• "I haven't met Serena yet" - calling out the real champion

• The "top 3" moment that changed everything

• Why champions think differently: the trophy in the trash story

• Richard Williams' philosophy on confidence winning big points

[48:00] The Champion's Mindset

• Passion and obsession as the #1 trait of exceptional performers

• Confidence vs. arrogance: where's the line?

• Why champions "don't respect anyone" on the court

• Novak Djokovic's early confidence and being labeled "cocky"

• The danger of thinking opponents are better than you

[58:15] The Progress Zone Philosophy

• Why comfort zones keep you static

• How to identify opportunities to live in the progress zone daily

• Arthur Ashe's quote: "Start where you are, use what you have, do what you can"

• The difference between judgment and learning from failure

[1:05:30] Dealing with Failure and Self-Judgment

• Three ways people react to failure (blaming others, blaming yourself, or learning)

• Why Americans are better at supporting vs. judging than Europeans

• The baby learning to walk: acceptance without judgment

• Roger Federer's commencement speech: winning only 54% of points

[1:15:45] Coaching at the Highest Level

• Game planning against Roger Federer: the Mike Tyson approach

• Communication as adaptation: knowing what to say, when, and how

• The story of changing strategy mid-match based on reading a player's panic

• Bob Brett's lesson: staying close while maintaining respect

[1:25:00] Difficult Relationships and Lessons Learned

• The rocky start with Richard Williams and earning respect

• Why complicated relationships can build the strongest bonds

• The end of the Serena partnership: mistakes and reflections

• Motivation vs. confidence: the real reason players seem unmotivated

[1:38:20] The Art of Coaching

• Transparency in life vs. strategic coaching

• "I don't listen to what people say, I hear what they think"

• Why knowing nothing was his greatest strength

• The danger of thinking you have all the answers

[1:45:00] Rapid Fire Wisdom

• Favorite quotes and philosophies

• "Be yourself, everyone else is already taken"

• "I know that I know nothing" - Socrates

• Why COVID became an opportunity to launch UTS

Key Quotes

"When you don't have tools, you'd better have creativity. That was my biggest strength as a coach—I knew nothing, so I had to think freely."

"Confidence is not a gift. Nobody's going to come and give it to you. You have to build it with little victories."

"Champions don't respect anyone on the court. It's not arrogance—it's confidence. If you think someone is better than you, you have no chance of beating them."

"There is no motivation without self-confidence. Zero. When you don't deeply believe you'll achieve your goals, you won't give 100%—it's a subconscious way to protect your confidence."

"The progress zone starts where your comfort zone stops. You have a hundred opportunities per day to live there. People just don't take them."

"Roger Federer won 54% of the points throughout his entire career and became one of the greatest players in history. Tennis teaches you to deal with frustration—because you'll lose almost as many points as you win."

"I hear what people think, not just what they say. If someone in London and someone in Miami both say 'the weather is nice,' they're thinking completely different things."

#120 Steve Lucas: Embracing Your Superpowers

Steve Lucas is the CEO of Boomi, a leading intelligent integration and automation platform. Before joining Boomi, Steve served as CEO of Marketo, where he led the company's transformation from a $1.6 billion valuation to its acquisition by Adobe for $4.75 billion in just 24 months—one of the largest software acquisitions in history. Prior to that, he held executive leadership roles at SAP and Salesforce, and cut his teeth in technology at Microsoft in the early 1990s. Steve is the author of "Digital Impact," exploring how AI and intelligent automation are reshaping business and society. A passionate advocate for diabetes research after being diagnosed with type 1 diabetes at 26, he serves on the board of the Children's Diabetes Foundation and recently established an endowed chair for diabetes research at the University of Colorado. Known for his curiosity, authenticity, and unwavering commitment to customers—he makes it a rule to speak with at least one customer every single day—Steve brings a unique blend of technical expertise and people-first leadership to one of technology's most transformative eras.

In this episode, we discuss:

• How Bill McDermott's simple advice—"just be you"—freed Steve from a decade of self-doubt and changed his career trajectory

• The power of saying "no": How Steve took Marketo from $1.6B to $4.9B by doing less, not more

• Why talking to a customer every single day is non-negotiable and how it transforms your entire organization

• Turning adversity into strength: Steve's journey with type 1 diabetes and the moment that changed his perspective forever

• The future of AI in the workplace and why we're the last generation of managers to manage only humans

  Watch the episode on YouTube here.

  Podcast Show Notes

  Timestamps & Key Topics

  [00:00:00] Introduction & Early Influences

  • Steve's father, a nuclear engineer, taught him to program in Fortran as a kid

  • Building IBM-compatible computers in the 1980s

  • The fascination with punch cards that sparked a lifelong passion for technology

  • Nature vs. nurture: passing curiosity forward to the next generation

  [00:06:30] What Makes Great Leaders

  • Three key traits: curiosity, being a "learn-it-all" not a "know-it-all," and deep empathy

  • Bill McDermott's profound impact as a mentor

  • The advice that changed everything: "Just be you"

  • Overcoming the "bull in a china shop" feedback that haunted Steve for a decade

  [00:15:45] Bill McDermott's Leadership Philosophy

  • What "always in your corner" really means

  • Bill leading while dealing with his life-changing accident

  • The authenticity and genuine care that sets great leaders apart

  • Why your network truly is your net worth

  [00:22:00] Turning Adversity Into Strength

  • Being diagnosed with type 1 diabetes at age 26

  • The "why not you?" moment with his wife

  • The woman at the restaurant who changed his perspective forever

  • Establishing an endowed chair for diabetes research with Dr. Michael McDermott

  [00:32:15] Early Career Lessons

  • Working full-time at Microsoft while going to school full-time at age 20

  • The bold declaration at 22: "I want to be CEO of a billion-dollar software company"

  • How early exposure to Microsoft shaped his entire career trajectory

  • The manager who laughed at his CEO ambitions (and got it wrong)

  [00:38:00] Generalist vs. Specialist: The Power of Variety

  • Why organizations programmatize people into single roles

  • The importance of context switching and orchestrating diverse skills

  • Thriving on variety and curiosity over predictability

  • Why the best CEOs have a variety of skills, not a single-track background

  [00:43:30] The Marketo Transformation

  • Taking Marketo from $1.6 billion to $4.75 billion in 24 months

  • The power of saying "no" and doing less, not more

  • Why B2B and B2C marketing are "apples and giraffes"

  • Pivoting from marketing automation to an engagement platform

  • The serendipitous alignment with Adobe's experience platform vision

  [00:52:00] Building Your Network

  • The importance of breaking bread, not just virtual connections

  • Post-COVID challenges with remote work culture

  • "We sat around campfires for millions of years"—human connection is in our genes

  • Why Starbucks is the modern campfire

  [00:56:45] The Daily Customer Rule

  • Steve's non-negotiable practice: talk to a customer every single day

  • How it transforms your worldview and makes you more customer-oriented

  • The incredible Marketo domain name story that proves relationships matter

  • Making customer connection as routine as brushing your teeth

  [01:04:00] Focus on Unlocking Progress, Not Chasing Titles

  • Why momentum isn't about job titles

  • Becoming the person who unlocks progress for others

  • How visibility is earned through delivering value

  • Steve's response when team members say "I want your job"

  [01:07:30] The Future of AI in Business

  • Why we're 2-3 years away from artificial general intelligence (AGI)

  • The last generation of managers to manage only humans

  • How AI agents are already automating expense reports at Boomi

  • Chat B: Boomi's AI sales assistant that prepares reps and creates custom presentations

  [01:18:00] AI's Impact on Society

  • What consumers need to know about AI

  • The opportunities: living longer, healthier, happier lives

  • The risks: job displacement and the need for better AI governance

  • Why governments aren't doing enough to protect humanity while managing AI

  • AI in diabetes care: the potential for personalized insulin management

  [01:26:00] Public Speaking & Communication

  • The two critical questions for every point: Is it interesting? Is it relevant?

  • Visualizing yourself on stage before presenting

  • Knowing you're ready when you dream about giving the keynote

  • Being authentically yourself: "Beware the perfect presentation—it was built with ChatGPT"

  [01:31:00] Balancing Family & Career Success

  • "I would quit a thousand times over if it meant sacrificing my family"

  • Being present and intentional when you're home

  • The realization about talking about himself too much

  • Expressing genuine interest in others as the key to success

  [01:37:15] Daily Habits & Self-Care

  • The simple rule: sweat every day

  • Winding down by learning something new

  • Falling asleep to World War II documentaries or space explorations

  • Binge-watching with his wife and having heated debates about characters

  [01:40:30] Book Recommendations

  • "The Infinite Game" by Simon Sinek

  • "How to Build a Car" by Adrian Newey

  • "Crossing the Chasm" by Geoffrey Moore

  • Ray Dalio's works

  • "Iconic": A photographic tribute to Apple innovation

  [01:44:00] The Car Restoration Hobby

  • Rebuilding cars with his son as a bonding experience

  • Deconstructing and reconstructing—just like his career approach

  • Starting with a 2008 Honda S2000 and adding a turbo

  • How the process mirrors his leadership philosophy

  [01:47:45] Final Career Advice

  • "Everything you want is on the other side of fear"

  • Overcoming fear as the most important skillset to develop

  • Why Steve waited until 41 to become a CEO (and wishes he hadn't)

  • "You're not gonna leave this earth without money in your checking account—so go do the thing"

  [01:52:00] Closing Thoughts

  Key Quotes

  "Be the first-rate version of you, not the second-rate version of somebody else." — Bill McDermott's advice to Steve

  "Great leaders are learn-it-alls, not know-it-alls." — Satya Nadella (quoted by Steve)

  "I will never complain about the food that I can pick up and put in my own mouth." — Steve's turning point moment

  "If you go a day without talking to a customer, it's a wasted day."

  "Focus on finding problems and delivering value. Become the person that unlocks progress for others."

  "Everything you want is on the other side of fear."

  "You are the last generation of managers to manage only humans."

Preview of the interview with Steve Lucas

#119 Jeff Pearlman: The Art of Storytelling

Jeff Pearlman is a New York Times bestselling author and one of America's most compelling sports writers, known for his meticulous reporting and ability to bring readers inside the locker rooms and lives of sports' most fascinating figures. He spent years as a writer for Sports Illustrated, where he famously broke the John Rocker story and honed his craft of finding extraordinary stories in unexpected places. Pearlman has authored numerous bestsellers including "The Bad Guys Won" about the 1986 Mets, "Showtime" about the Lakers dynasty which became an HBO series, "Boys Will Be Boys" about the Dallas Cowboys, and books on Bo Jackson, Walter Payton, Brett Favre, and Tupac Shakur—the latter requiring interviews with 650 sources. His YouTube show "Press Box Chronicles" has become a viral sensation, with millions tuning in to hear him share nostalgic deep dives into sports history's most memorable moments, characters, and forgotten stories. Today, Jeff continues to prove that great storytelling is built on one simple principle: getting the details right and treating people with kindness along the way.

What We Discuss:

• The power of details in storytelling - Why "taking the little and making it big" transformed Jeff's career, and how getting the facts matters more than fancy writing in today's 22-second video clip world

• Building a career on kindness and relationships - How treating people with grace opened doors throughout Jeff's journey, from his father's lesson about never talking trash to why your network remembers how you made them feel

• The mistakes that shaped his success - From asking a chef about cannibalism to getting his "ass kicked" on Delaware's track team, Jeff shares the failures and humbling moments that became his most important teachers

• Balancing career ambition with being present as a parent - Why Jeff never missed a single moment with his kids for a TV game, his thoughts on the "hashtag girl dad" phenomenon, and parenting wisdom from his wife Catherine (who donated a kidney to a stranger)

• The unlikely rise of Press Box Chronicles - How a writer who thought "nobody's gonna watch this" built a viral YouTube show powered by nostalgia, and why choosing projects that hold your interest for two years matters more than chasing money

Show Notes: Jeff Pearlman Interview

[0:00-5:00] Introduction & Childhood Heroes

• Jeff's childhood hero: Ken Griffey Sr. and the picture still hanging on his wall

• Gary Templeton and the moment he "had me at hello"

• Meeting Ken Griffey Sr. as an adult journalist and getting starstruck

• Rethinking Darryl Strawberry's legacy with compassion and perspective

[5:00-15:00] The Father's Blueprint

• Stanley Pearlman's 1986 self-published book "Conquering the Corporate Career"

• The Waldenbooks guerrilla marketing strategy: moving books to the bestseller section

• Creating fake publicists David Kohlberg and Arthur Haviland (the Trump/John Barron parallel)

• The most important lesson: his father's superpower of never talking trash about anyone

• The 1985 moment that shaped Jeff's approach to treating people with grace

[15:00-25:00] The Unlikely Path to Journalism

• Why Jeff didn't get into Penn State's main campus

• Walking onto Delaware's track team and "getting my ass kicked over and over"

• Why failure and humiliation became "one of the most important experiences of my life"

• First real job: Food and fashion writer at Nashville Tennessean making $26,000/year

• The cannibalism question that should have gotten him fired

[25:00-35:00] Breaking Into Sports Illustrated

• The childhood dream: "I'm gonna write for Sports Illustrated" (said with certainty, not hope)

• The NBA draft application prank that became his first SI article

• Getting hired at age 24: "I always thought I would get to SI at like 35 or 40"

• The competitive environment and his unique hustle strategy

• Calling every college in America alphabetically looking for the "three foot seven gymnast"

[35:00-45:00] The Turning Point: Learning to Report

• The best career advice ever: Catherine Mayeux's "Just get the facts"

• "I was always writing around my lack of information... I didn't have the details, I just had the flare"

• Why this became "the most important moment in my career as far as turning it around"

• The philosophy that changed everything: "Take the little and make it big"

• The Mike Trout example: finding the Make-A-Wish kid photo behind the locker

[45:00-55:00] Stories That Matter: The Tyler Ugolin Story

• Calling Victor Ugolin just days after 9/11

• Why Victor called back: "What if I just tell you about my son?"

• The 40-minute conversation and what changed his mind

• Remaining close friends for over 20 years

• The supernatural moment: meeting Tyler's high school girlfriend in a random Penn State coffee shop

[55:00-65:00] Books, Regrets, and Rich Gannon

• Writing his first book about the 1986 Mets

• The Roger Clemens book: "I kind of did it for the money"

• Why you need subjects with depth or surrounded by depth

• The three-pronged criteria: Will it hold my interest for two years?

• The hilarious Rich Gannon "Sexiest Man Alive" mixup with Elvis Grbac

• His evolved stance on Hall of Fame voting for steroid users

[65:00-75:00] The Art of Door Knocking

• The scariest door knock: JR Rider's house in Arizona

• "Bro, you cannot just show up in my house... So what are you working on?"

• How showing up with his USFL book turned the situation around

• The Nashville apartment with blood and bullet holes

• Why good judgment sometimes means ignoring your editor's advice

[75:00-85:00] Writing Advice: The Power of Details

• "It's not just a soda... It was a Fanta orange soda with the peel ripped off and some lipstick stain on the rim"

• Russell Baker's wisdom: having the villain bend over to smell a rose

• "Show the complexity of humanity"

• Why details matter more than ever in the age of 22-second video clips

• The Bronx Zoo by Sparky Lyle: the book that became his model

[85:00-95:00] The Tupac Book & Hip Hop

• Interviewing 650 people for the Tupac biography

• The beautiful butterfly kid at Baltimore School for the Arts

• "The type of person who would gently remove a ladybug and place it aside"

• The contrast: going home every night to a hellscape in East Baltimore

• Who shot Tupac? "Orlando Anderson, a hundred percent"

[95:00-105:00] Press Box Chronicles: The Unlikely Hit

• Starting TikTok out of spite after a columnist called him an "old relic"

• His son's advice: "Don't do TikTok... don't talk politics, don't use filters"

• When 3.0 Labs approached him: "Nobody's gonna care. Why would anyone care?"

• The 1984 San Diego Padres episode that mysteriously went viral

• "My whole career bookwise is nostalgia powered. Sports is all about nostalgia to me"

• Planning a tour (even though "nobody's gonna wanna come and see me")

[105:00-115:00] Parenting Philosophy

• "The greatest gift of this career: I was available for everything"

• Being the "class mom" and never missing a moment for a TV game

• Why he hates "hashtag girl dad": "I wasn't a girl dad, I was a dad of a kid who I freaking loved"

• His wife Catherine's parenting book "Ignore It" and why attention-seeking behavior should be ignored

• The Halloween/World Series example: "That's a horrible mistake"

[115:00-125:00] Catherine's Kidney Donation

• The Starbucks flyer that changed everything

• "Would it be weird if I donated a kidney to a stranger?"

• Meeting Eli and Monica for the first time on the day of donation

• How they became their closest friends in California

• Why it's one of Jeff's proudest moments (even though it was her accomplishment)

[125:00-135:00] Life & Career Lessons

• "Another person's success does not detract from yours"

• Letting go of the goal to be "the greatest sports writer who's ever lived"

• "My whole career has been just a total lark... I get to write about sports and hip hop for a living"

• If you treat people kindly, people remember (and vice versa)

• The Tupac book example: getting help from sports media friends he'd known for years

[135:00-145:00] Advice to Young Journalists & Writers

• "Don't be a jackass... none of it's that important"

• Choose projects that will hold your interest for two years

• In the age of fast content, you'll stand out if you actually report

• View each chapter as a long feature (credit: John Wertheim)

• Why you don't need an editor hanging over you to be productive

[145:00-End] Rapid Fire & Final Thoughts

• Playing basketball Saturday and Sunday mornings (the mediocre game continues)

• Pearl Washington: his favorite basketball player of all time

• The two pieces of memorabilia he keeps: the '86 Mets ball and JR Richard's autograph

• What he'd tell his 40-year-old self (or better yet, his 25-year-old self)

• Final wisdom: "Just be decent to people... and don't forget about details"

Resources Mentioned:

• Books: "The Bad Guys Won," "Showtime," "Boys Will Be Boys," "Football for a Buck," "The Last Folk Hero" (Bo Jackson), "Gunslinger" (Brett Favre), "Three-Ring Circus" (Shaq & Kobe), "Tupac Shakur: The Authorized Biography"

• Press Box Chronicles on YouTube

• "Ignore It" by Catherine Pearlman

• "The Bronx Zoo" by Sparky Lyle and Peter Golenbock

• "Conquering the Corporate Career" by Stanley Herz

#118 Max Richter: Move Fast and Break Things - Building Insta360

Max Richter grew up in Stuttgart, Germany, surrounded by cameras—his father was a photographer with a Leica who ran an advertising business. After studying engineering and business, Max found himself restless in corporate life, eventually making his way to Shenzhen, China, where he met a campus legend named JK who had borrowed $2,000 from his father to start a camera company. What happened next was a decade-long journey of near-bankruptcy, pivotal pivots, and ultimately building Insta360 into a company that challenged GoPro and partnered with the very camera brand that filled Max's childhood home. Today, Max serves as a co-founder of Insta360, a company that's redefined how millions of people capture and share their lives.

In this episode, you'll discover:

• The "dark year" of 2017 when Insta360 had over 100 employees, was running out of cash, and Samsung had just entered their market—and the unexpected user behavior that saved the company

• Why the moment you're closest to giving up is often the exact moment you need to push through, and how this principle turned a struggling startup into a company that makes $30+ million annually

• The career advice Max wishes he'd known at 25 about the dangers of overthinking and why "just starting" beats perfect planning every single time

• How immersing yourself in uncomfortable, foreign environments shapes you into a more open-minded person—and why Max believes traveling early is one of the most underrated career accelerators

• The sacrifices nobody talks about when building a global company, and why finding the intersection of passion, profit, and societal impact matters more than any single factor alone

#117 Jay Shetty: On Finding Your Purpose

Jay Shetty has inspired millions of people through his inspirational YouTube videos, best-selling books and his podcast, On Purpose. He shares much of his wisdom as a former monk through his teachings. In this interview we discuss:

-The #1 trait of high performers

-The hardest part of finding your purpose

-Why we should study people instead of envying them

-The best career advice he ever received 

-What we get wrong about trauma

-How to cultivate meaningful relationships and more..

Key Topics Covered

[0:00-3:00] Introduction & Studio Setup

• Jay's background and accomplishments

• Discussion about podcast studio design and creating an inviting atmosphere

• Jay's use of "Easter eggs" in his studio (pictures of eyes for eye contact, heart shapes)

• Philosophy behind creating energetic spaces

[3:00-8:00] Interview Style & Presence

• Jay's approach to being present during interviews

• Not planning next questions while guests are talking

• Importance of preparation vs. presence in interviews

• Leaving in thinking pauses and awkward silences

• Balance of 10% planned questions, 90% organic flow

[8:00-12:00] Childhood Heroes & Influences

• David Beckham as a major influence growing up

• Dwayne "The Rock" Johnson and wrestling fandom

• Reading Martin Luther King and Malcolm X biographies as a teenager

• Combining entertainment/storytelling with impact/service

[12:00-18:00] Childhood & Family Influence

• Being bullied for being overweight and skin color

• Mother as an "emotional shield"

• Key concept: High standards, high grace - holding yourself to high standards while showing compassion when you don't meet them

• Roger Federer's philosophy: "When I'm playing a point, it's the most important point. When it's over, it's the least important."

[18:00-22:00] Finding Purpose - Core Philosophy

• Purpose as a daily commitment, not a one-time discovery

• Purpose = passion in action

• MLK quote: "Those who love peace must learn to organize as effectively as those who love war"

• Strategy and sincerity must go together

• Systems and execution are just tools that can be used for good

[22:00-28:00] The Work Behind Purpose

• Purpose requires daily work and commitment

• Like maintaining physical fitness - it's not a one-time achievement

• Purpose is active, dynamic, and evolving

• Key insight: Purpose is about transformation, not titles

• Vehicles (podcasting, speaking) vs. actual purpose (helping people find peace and purpose)

[28:00-32:00] Princeton Commencement Speech

• Honor of speaking at Princeton's class day

• Nerves and preparation for the speech

• Steve Jobs's Stanford speech as inspiration (listened to it daily for 9 months)

• Student response and impact of the speech

[32:00-36:00] Four Major Life Decisions

• Based on 5,000-year-old Vedic literature

• Four pillars: Dharma (purpose), Artha (money), Kama (love), Moksha (liberation/service)

• Why service to humanity was included as the fourth decision

• Service as what the human heart is wired for

• Research showing people are happier when spending money on others

[36:00-42:00] Success & Service Philosophy

• High performers need both success and service

• Strategy and sincerity go hand in hand

• Key principle: "We are wired for generosity but educated for greed"

• The middle path vs. living in extremes

• Why privilege creates more responsibility to give back

[42:00-45:00] Career Advice

• Best career advice: "Open every door first, keep walking through the ones that remain open"

• Don't wait for one door - knock on multiple doors

• Jay's TV show rejections leading to starting On Purpose podcast

• The "Third Door" concept - sometimes it's not the front door

[45:00-50:00] Podcast Launch Struggles

• Production company backing out 2 weeks before launch

• Being told "people won't listen to you for an hour"

• Self-funding and launching anyway on Valentine's Day 2019

• Building everything in-house vs. relying on external companies

[50:00-54:00] Dealing with Rejection & Criticism

• Learning that most people won't get your vision

• Experience from becoming a monk - looked like failure entering and leaving

• People project their limitations onto you

• This pattern continues with every new venture (like Juni beverage company)

[54:00-62:00] Juni Sparkling Tea Business

• Jay's personal sugar addiction story

• Wife's influence as nutritionist in changing his diet

• Creating healthy alternatives that taste good

• Juni's ingredients: ashwagandha, lion's mane, green tea/hibiscus, reishi mushroom, acai cherry

• Business success metrics and growth on Amazon

• Philosophy: "Something shouldn't taste bad to be good for you"

[62:00-65:00] Rapid Fire Questions

Trauma insights from Dr. Gabor Maté:

• Trauma often happened before the traumatic event

• If you couldn't tell your parents about something bad, the real trauma was not trusting them in the first place

• Importance of maintaining communication lines with loved ones

Relationship advice:

• A relationship is only worth saving if BOTH people want to save it

• Don't waste energy convincing someone to stay in your life

• People change for themselves, not because others want them to change

Cultivating meaningful relationships:

• Biggest blind spot: thinking "we should just get each other"

• Meaningful relationships require meaningful disagreement and discussion

• Both partners must work on themselves individually AND the relationship together

• Growth happens at different paces

[65:00-67:00] Final Wisdom

What Jay wishes he knew at 27: "No matter what your intention is, no matter how much you care, no matter how much you try, you will always be misunderstood by people who want to misunderstand you."

Key Takeaways

1. High Standards, High Grace - Hold yourself to high standards while showing compassion when you fall short

2. Purpose is Daily Work - Not a one-time discovery but a daily commitment and practice

3. Study vs. Envy - Learn from successful people rather than being bitter about their success

4. Strategy + Sincerity - Good intentions need good systems to create real impact

5. Open Every Door - Don't wait for one opportunity; pursue multiple paths simultaneously

6. Both People Must Want It - Relationships only work when both parties are committed to making them work

#116 Keith Hawk: Relentless Focus on the Process

Keith "Pistol" Hawk was VP of Sales at LexisNexis where he led a salesforce of over 1,000 people. He co-authored "Get-Real Selling: Your Personal Coach for REAL Sales Excellence" and he's given many keynote speeches at corporate events about leadership. 

In this episode we discuss:

-How his upbringing helped him become self-reliant at an early age

-The power of presence when raising children

-The keys to a long, happy marriage 

-Pitfalls of leadership

-Having hard conversations at work, and more

Key Timestamps & Topics

[00:00 - 05:30] The Pistol Pete Origin Story

• How his kids nicknamed him "Pistol" after Pete Maravich

• Early athletic influences: Pete Rose's "Charlie Hustle" mentality

• The value of effort over pure talent

• Growing up in small-town Ohio

[05:30 - 12:00] Early Lessons in Self-Reliance

• Selling seeds door-to-door at age 11

• Paper routes and ice cream sales at ballparks

• "You lose the fear of the word no"

• Parents who didn't helicopter - letting kids deal with adversity

[12:00 - 18:30] His Father's Inspiring Journey

• Dad went from factory welder to engineering degree

• Driving 45 miles each way to night school for 8 years

• Graduating college the same week Pistol graduated high school

• "He really worked hard for a guy that didn't like school when he was young"

[18:30 - 25:00] Parenting Philosophy: Presence Over Interference

• Not being helicopter or "lawnmower" parents

• The one-match fire challenge and building self-reliance

• Being available for counsel without leading by the nose

• "Very good for counsel, especially my dad"

[25:00 - 32:00] The Ultimate Dad Move

• Missing only 2 games in AJ's 11-year NFL career

• Splitting games with his wife during college overlap years

• "You go to your kids' games, right? I just get to do it for a longer time"

• AJ flying back for kids' games during NFL Draft weekend

[32:00 - 40:00] Youth Sports Coaching Wisdom

• Focus practice time on playing the game, not calisthenics

• "These are kids. They're already in shape"

• Multi-sport over specialization: "It's about competing"

• The "running a Trotwood" team-building exercise

[40:00 - 48:00] Marriage: Keeping It Fresh After 45 Years

• The daily ritual: brushing teeth before going home

• "I want to treat her like I'm going on a date with her"

• Avoiding the trap of taking each other for granted

• Being intentional about being a servant leader

[48:00 - 55:00] Sales Philosophy: Success Follows Customer Success

• Writing "Get Real Selling" only on airplanes

• "My success can only follow the success of the customer"

• Why great salespeople are listeners, not talkers

• The stereotype problem with sales

[55:00 - 65:00] Leadership Lessons: Front Lines vs. Ivory Tower

• Leading a 1,500-person sales organization

• The importance of being on customer calls

• "There's no substitute for direct communication"

• Focus on process metrics, not just end results

• "What are the plays we're running that are successful?"

[65:00 - 75:00] Hiring: Simulations Beat Interviews

• AT&T's all-day simulation process

• "Interviews are useful, but are not enough"

• Looking for organization and listening skills

• Putting candidates in the "natural habitat" of the job

[75:00 - 85:00] The Career Pivot That Changed Everything

• Getting replaced as head of sales

• Proactively approaching the new CEO with a solution

• "I am a collection of experiences, skills, and knowledge"

• Five years as the "battle-tested" customer problem solver

• Coming back as "a sharpened weapon"

[85:00 - 92:00] Golf and Making Yourself Available

• The "Join Us" philosophy on the golf course

• Meeting 70-80 new people in four months

• "If you make yourself available, people really appreciate that"

[92:00 - 98:00] Rapid Fire: Books, Advice, and Legacy

• Recommended episodes: Kat Cole, George Raveling, latest Hawk Boys episode

• Book recommendations: "The Score That Matters," "In Search of Excellence"

• What he hopes his sons say about him: "He was always there for me when I needed him"

[98:00 - 102:00] Three Career Success Principles

• Organize your life: Be proud of how you go about your business

• Become a tremendous communicator: Public speaking can help you "outrun your other skillset"

• Always be a great teammate: Not just an individual contributor

Key Quotes

"My success can only follow the success of the customer."

"Great players are easy to scout. It's the good ones that lure you into thinking they're great."

"You've gotta fight through the nos to get to the yeses."

"It's our duty as a leader to be in a good mood."

"Little eyes are watching all the time."

Resources Mentioned

• Book: "Get Real Selling" by Keith Hawk and Michael Boland

• Book: "The Score That Matters" by Ryan Hawk

• Book: "In Search of Excellence" by Tom Peters

• Podcast: The Learning Leader Show with Ryan Hawk

#115 Ariel Kaye: The Art of Progress Over Perfection

Ariel Kaye is the founder and CEO of Parachute, the Los Angeles-based home essentials brand she launched in 2014. With no prior retail experience, Ariel transformed a simple observation about the lack of quality, non-toxic bedding into a multi-million dollar company that has redefined the direct-to-consumer home goods space. Before founding Parachute, she worked in marketing and media, experiences that proved invaluable in building a brand known for its storytelling and customer-centric approach. Today, Parachute operates retail stores across the country and has partnered with major retailers like Target, all while maintaining its mission of bringing comfort and quality into people's homes.

In this episode we discuss:

• Why "I'll figure it out" is a legitimate business strategy – How embracing uncertainty and learning as you go can be more powerful than having all the answers upfront

• The transformative power of belief – How one friend's confidence in her abilities changed everything, and why believing in others (and telling them so) can literally change lives

• Why asking for help is your secret weapon – How to overcome the fear that not knowing everything makes you weak, and why the best leaders are the ones who know what they don't know

• How to handle rejection without losing momentum – Practical strategies for dealing with hundreds of "nos" from investors while staying focused on your vision

• The art of progress over perfection – Why small, consistent actions often matter more than grand gestures, especially for high achievers who get stuck in perfectionist cycles

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Check out the t-shirts for the podcast: https://www.bonfire.com/to-the-top-4/

Check out Parachute here

Follow Ariel on LinkedIn here

—

SHOW NOTES:

Key Timestamps & Topics

Opening & Background (0:00 - 12:00)

• [0:00] Introduction and episode overview

• [1:30] Ariel's background and current role at Parachute

• [3:00] Growing up with entrepreneurial parents

• [5:15] Her mother's pioneering work in service learning education

• [7:20] Her father's chiropractic practice and how her parents met doing tai chi

• [9:45] How her unconventional upbringing shaped her worldview

• [11:30] Early career struggles and feeling "lost" after college

The Pivotal Moment (12:00 - 22:00)

• [12:00] The dinner at The Mermaid restaurant that changed everything

• [14:30] Eddie Kim's six words: "You're a CEO, you are a founder"

• [16:45] The immediate impact of having someone believe in her potential

• [18:20] The phone call to her parents announcing her decision

• [20:15] Her parents' reaction: surprise, concern, and ultimate support

• [21:30] Why she wasn't asking for permission, but announcing a decision

Taking the Leap (22:00 - 32:00)

• [22:00] Leaving New York for Los Angeles

• [24:15] Strategic reasons for choosing LA's startup ecosystem

• [26:30] The "I'll figure it out" mentality and embracing uncertainty

• [28:45] Joining an accelerator program in fall 2013

• [30:20] First realizations about not knowing everything

• [31:15] The transition from fear to acceptance of inexperience

Learning to Ask for Help (32:00 - 42:00)

• [32:00] Why asking for help initially felt like weakness

• [34:30] The accelerator experience and access to mentors

• [36:15] Discovering that all startups solve similar core problems

• [38:00] "People are generous with their time" - the revelation

• [39:45] How asking for help became her "superpower"

• [41:20] Building a network of fellow entrepreneurs and advisors

The Funding Gauntlet (42:00 - 52:00)

• [42:00] "Hundreds of meetings" with investors who said no

• [44:15] Common objections: "Where's your technical co-founder?"

• [46:30] Learning that investors look for reasons NOT to invest

• [48:45] How rejection taught her to refine her pitch and preparation

• [50:20] Finding her unique value proposition as a consumer advocate

• [51:30] Not internalizing doubt from investors who "didn't get it"

Launch and Early Success (52:00 - 60:00)

• [52:00] January 16, 2014 - official Parachute launch

• [53:30] Going from 6 to 20 to 40 orders per day in the first week

• [55:15] The emotional impact of seeing orders from unknown towns

• [57:00] Obsessively checking Shopify and watching live site activity

• [58:30] The first large order: "This has gotta be fraud, right?"

• [59:45] Media coverage and validation from strangers

Building a Mission-Driven Company (60:00 - 68:00)

• [60:00] Customer stories that shaped Parachute's deeper mission

• [62:15] Products appearing organically in Sex and the City

• [63:30] The power of comfort in people's most intimate spaces

• [65:00] Letters from customers during life's biggest moments

• [66:45] Partnership with Target and retail expansion

• [67:30] Why internal team collaboration matters most to her

Leadership and Paying It Forward (68:00 - 72:00)

• [68:00] Her leadership philosophy: empathy and believing in people

• [69:30] Mentoring other entrepreneurs and the power of encouragement

• [70:45] "Texting someone 'I believe in you' can change their life"

• [71:30] Building culture where people feel "happy, seen, supported"

Life Lessons and Advice (72:00 - 75:00)

• [72:00] Balancing motherhood and running a company

• [73:15] Three key pieces of advice for early career professionals

• [74:00] "Progress, not perfection" - why good enough is often enough

• [74:30] "Be kind" - it costs nothing but impacts everything

• [75:00] The importance of building community with fellow entrepreneurs

Key Quotes from the Episode

"I had never felt so consumed with an idea. Never felt so impassioned, had never felt so sure about something... mind you, I had no idea what I was doing."

"He looked at me and said, 'you're a CEO, you are a founder'... that single phrase fully changed the trajectory of my life."

"I realized that people were really generous with their time and if you have a question and you can ask it with clarity and you can ask it to the right person, people want to help."

"Investors are genuinely looking for reasons not to invest, not why they should invest. That was a real shift in my perspective."

"It's the power of progress, not perfection, that actually moves the needle."

"Texting someone like 'I believe in you' can literally change the course of someone's life."

Resources Mentioned

• Parachute - parachutehome.com

• Book: Atomic Habits by James Clear

• Book: The Five Types of Wealth (mentioned as recent read)

• Target Partnership - Parachute products available at Target stores

• Eddie Kim - Early investor and board member who delivered the pivotal encouragement

#114 Jeanelle Teves: Unshakeable Self-Confidence

We're joined by Jeanelle Teves, Chief Commercial Officer of North America at Bugaboo, the premium Dutch stroller company known for its innovative design and engineering excellence.

Jeanelle's career journey is a masterclass in turning uncertainty into opportunity—from answering phones at her parents' dental practice at age nine to scaling global brands at Nike across Europe and New York, and now leading growth for one of the world's most recognizable parenting brands. As a first-generation Filipino American who lived in the Netherlands for nearly a decade before becoming a new mother herself, she brings a unique perspective on building careers, leading teams, and creating products that truly solve problems for parents worldwide. 

In this conversation, you'll learn:

-The "Why Not You?" mindset that her immigrant parents instilled and how it shaped every major career decision

-Her 5 AM routine and "3-3-3 exercise" for starting each day with intention and gratitude -Why being "consistently good beats being occasionally great" and how small, compound actions build extraordinary careers

-The art of "praising in public and criticizing in private" to build psychological safety and high-performing teams

-How she identified the perfect career opportunity at the intersection of personal experience and professional growth

-Bugaboo's obsessive approach to solving real parental problems and why their durability standards are seven times higher than industry minimums

-The power of treating your network like a bank account and making relationship deposits before you need to make withdrawals

Whether you're early in your career or leading teams of your own, Jeanelle's insights on communication, consistency, and finding green shoots of optimism even in challenging times will change how you think about building both professional success and personal resilience.

Time-Stamped Show Notes

[00:00 - 02:30] Introduction & Early Life

• Host introduction and guest background

• Growing up in an entrepreneurial Filipino American family in Sacramento

• Parents building a dental practice from scratch as immigrants

• First job at age 9: answering phones in the family business

[02:30 - 07:15] The Foundation: "Why Not You?" Philosophy

• How immigrant parents instilled an unshakeable belief in possibility

• Learning that "the world will tell you so many reasons you can't do it"

• Watching parents design a completely new life in America

• The power of family as your "first team"

[07:15 - 12:45] Early Career Lessons: Communication & Confidence

• Overcoming anxiety about answering phones as a child

• "If you are confident, the other person won't doubt you"

• Learning to ask: "What is the problem you're looking to solve?"

• How childhood experiences shaped boardroom confidence today

[12:45 - 19:30] The International Journey: Education as Adventure

• Childhood dream of traveling and getting on airplanes

• Buying a one-way ticket to Barcelona for graduate school

• Meeting future husband and moving to Amsterdam

• Landing at Nike European headquarters

[19:30 - 26:00] Nike Years: Building Global Brand Experience

• Nearly a decade at Nike across Europe and New York

• Traveling all around Europe for work, "living childhood dreams"

• Becoming General Manager of Nike Women's in New York

• Learning to focus on "the athlete" and customer-centric thinking

[26:00 - 33:15] The Bugaboo Opportunity: Perfect Timing

• Why she was happy at Nike but open to change

• "Perfect intersection" of new motherhood and professional opportunity

• Being the target customer: "I had a newborn son at home"

• Leveraging 10 years of Netherlands experience where "Bugaboo is a household name"

[33:15 - 39:45] Understanding Bugaboo: More Than Celebrity Appeal

• The misconception about being just a "celebrity brand"

• "It drives like butter" - focus on quality and precision engineering

• Design standards "as if sending a rocket into space"

• Durability tests 7x higher than industry standards

• 25-year history as category creator founded by Max as college project

[39:45 - 46:30] Product Innovation: The Bugaboo Kangaroo Story

• First stroller designed specifically for American parents

• Solving the "second child" dilemma with modular design

• "Push it like a minivan down the streets of New York"

• Filling missing piece in product puzzle for North American market

[46:30 - 52:00] Leadership Philosophy: Psychological Safety & Team Building

• Best leadership advice: "Praise in public and criticize in private"

• "Your whispers become shouts" as a leader

• Managers impact mental health more than spouses or friends

• Creating psychological safety for innovative thinking

• "I am only one brain, but there are several other brains around the room"

[52:00 - 58:15] Daily Excellence: The 5 AM Routine

• Morning routine starting at 5 AM

• The "3-3-3 exercise": 3 wins, 3 gratitudes, 3 daily priorities

• Sleeping with notebook next to bed

• "Filling your cup" as executive responsibility

• Focus on "green shoots" - finding positive signals in challenges

[58:15 - 64:30] Learning from Failures: The Communication Thread

• Common denominator of career setbacks: miscommunication

• "Foundation of all my wins" - clear, concise communication

• "Feedback is a gift - give it and move on"

• Learning from both great and terrible managers

[64:30 - 69:45] The Gratitude Practice That Changes Everything

• Running "gratitude note" on phone since 2020

• Using it during tough times: "I have the wind at my back"

• "Impossible to have a bad mood if you feel grateful"

• Building abundance mindset through systematic gratitude

[69:45 - 75:00] Customer Impact: More Than Just a Stroller

• Stories from dinner parties: "I was a Bugaboo mom"

• Products lasting through multiple children and generations

• Emotional attachment: "It's where they take their naps, their grocery wagon"

• Personal experience giving away own son's stroller recently

[75:00 - 80:15] Policy Changes: Empowering Parents Beyond Products

• Extending maternity leave to 16 weeks

• Flexible return-to-work plans (part-time pay, full-time benefits)

• CEO Adrian Theory's commitment to "doing the right thing"

• Sustainability efforts that may hurt profitability but serve long-term mission

[80:15 - 85:30] Career Advice: Consistency Over Brilliance

• "Don't underestimate the power of relationships and mentors"

• Network as bank account: "constantly putting in deposits"

• "Be consistently good" vs. "occasionally great"

• "Your boss asks for it Friday? Deliver it Thursday afternoon"

• Compound 1% gains from "Atomic Habits" philosophy

[85:30 - 89:00] Recommended Reading & Final Thoughts

• "Atomic Habits" by James Clear

• "Career Forward" by Grace Puma and Christiana Shi

• "Simple Act of Gratitude" (host recommendation)

• Why small things matter and compound over time

[89:00 - 90:00] Closing & Contact Information

• How to connect with Jeanelle and Bugaboo

• Final thoughts on "Why Not You?" mindset

• Host wrap-up and episode conclusion

Key Quotes

• "Why not you? The world will tell you so many reasons you can't do it, but why not you?"

• "Your whispers become shouts when you're a leader"

• "Be consistently good - that will take you much farther than being occasionally great"

• "Feedback is a gift - give it and move on"

• "I am only one brain, but there are several other brains around the room"

Resources Mentioned

• Books: "Atomic Habits" by James Clear, "Career Forward" by Grace Puma and Christiana Shi

• Company: Bugaboo strollers and baby products

• Concepts: 3-3-3 morning exercise, psychological safety, compound 1% gains

Connect with Jeanelle Teves

• LINKEDIN

#113 Tim Bantle: Authenticity Is Your Competitive Advantage

In this episode, I sit down with Tim Bantle, President of heritage brand Filson and the former Patagonia executive who helped transform a $200 million company into a billion-dollar global powerhouse. From his philosophy degree to building some of the outdoor industry's most iconic products like the Nano Puff, Tim shares the unconventional path that led him to the top of two legendary American brands. You'll discover why he doesn't have a resume, how a family crisis became his greatest career opportunity, and the simple advice from his optician father that shaped his entire approach to business. Tim reveals the leadership strategies that actually work—from asking questions for six months before making changes to why authenticity is your ultimate competitive advantage. Whether you're climbing the corporate ladder or building your own business, this conversation is packed with practical wisdom from someone who's actually done it.

What We Discussed:

• From Philosophy Student to Outdoor Industry Leader - How Tim's unconventional academic background in philosophy and literature led to a career building billion-dollar outdoor brands, and why his father jokingly told other parents to have their kids "just study philosophy"

• The Product Innovations That Changed Everything - The inside story of creating Patagonia's breakthrough products like the Down Sweater and Nano Puff, including how a failed fleece project accidentally revolutionized down insulation and became a billion-dollar product line

• How Family Crisis Became Career Catalyst - Why having a special needs child and his wife leaving her career actually freed Tim to pursue global opportunities, leading to roles across California, Utah, Europe, and Canada

• Leadership Without a Playbook - Tim's approach to taking over heritage brand Filson, why he spends six months asking questions before making changes, and how he avoids the trap of bringing solutions from previous companies

• The Network Effect and Authentic Success - Why Tim doesn't have a resume, how every job opportunity came through relationships, and his philosophy that being the best version of yourself is the key to finding the right opportunities

SHOW NOTES:

[0:00 - 2:30] Opening & Background

• Introduction and connection from Seattle

• Growing up in St. Louis as second of six kids ("the Bantle bunch")

• Father's optician business and mother staying home

[2:30 - 5:15] Father's Life-Changing Advice

• Key Quote: "Focus on selling people things they want, not things they need"

• How this wisdom shaped Tim's entire career approach

• Why people pay premium for wants vs. minimal for needs

[5:15 - 8:45] Educational Path & Philosophy

• Studying philosophy and literature in college

• Everyone assuming he'd become a lawyer

• Originally planning to be a professor

• Working in a gear shop during college - the pivotal moment

[8:45 - 12:30] Leadership Qualities Discussion

• Intelligence as a foundational leadership trait

• Integrity and moral compass as non-negotiables

• Critical thinking skills from philosophical background

• Father's joke: Telling parents their kids should "just study philosophy"

[12:30 - 18:00] Influential Leaders

• Yvon Chouinard (Patagonia founder) - "Management by absence" philosophy

• Setting high-level direction without micromanaging

• Ambivalent relationship with formal hierarchy

• Comparison to Steve Jobs - different paths, similar results

[18:00 - 22:15] Best Career Advice

• High school teacher's course: "Follow Your Bliss"

• Bill Moyers/Hero's Journey framework

• Passion leading to success - living proof of the concept

• Teaching skiing, rock climbing, and kayaking after college

[22:15 - 26:45] Early Career Lessons

• Working at National Outdoor Leadership School (NOLS)

• Ranch work in Wyoming teaching outdoor skills

• Character building through suffering - first 10 years grinding

• Long days, low pay, but essential development period

[26:45 - 30:30] The Network Effect

• "I don't have a CV" - all jobs came through relationships

• Never knowing what he'd be doing 18 months ahead

• Phone calls leading to opportunities

• Reputation preceding you in the industry

[30:30 - 36:15] Geographic Mobility & Adaptation

• Living in multiple countries and states

• The family crisis that became opportunity

• Son with special needs, wife leaving her career

• Freedom to move wherever opportunities arose

[36:15 - 41:00] Mountain Climbing Philosophy

• Focus and flow states in extreme sports

• Being fully immersed in the moment

• Connection to intense work and creative pursuits

• "People are happiest when fully focused"

[41:00 - 47:30] Why Filson?

• Founded in 1897 - one of oldest apparel companies in US

• Gold Rush origins, outfitting people for Alaska

• Manufacturing products from 1914 patents

• Supplier relationships over 100 years old

• "Never really been exposed to a much larger audience"

[47:30 - 52:45] New CEO Advice

• "You gotta ask a lot of questions" - six months of continuous inquiry

• Avoiding the "Nike playbook" trap

• Understanding business on its own terms

• Each brand needs custom approach based on lifecycle stage

[52:45 - 56:00] Ground-Up Experience vs. Consulting

• "Go back and work, start out in retail when you're 18"

• Five years living in a tent 150 days a year

• Knowing the nuances of customer problems

• Apparel business as anthropology

[56:00 - 62:30] Proudest Accomplishments

• #1: Family relationships - loving relationship with wife and kids

• Kids adapting to global moves (ages 14 and 11)

• Patagonia's hypergrowth - $200M to potential $2B business

• Yvon initially skeptical: "It's just really hard to take market share"

[62:30 - 68:45] Product Innovation Stories

• Down Sweater breakthrough - reinventing fleece led to down innovation

• Cutting channel thickness in half = half the down needed

• Nano Puff creation - synthetic version of down concept

• Trademark story - beating Apple's iPod Nano to registration

[68:45 - 72:15] Product Success Indicators

• Knowing when you have a hit product

• Internal sales team excitement

• Retailer orders exceeding forecasts

• "Feels like a well-struck ball"

• Chase mode to meet demand

[72:15 - 76:30] Learning from Failures

• Filson's challenge: products "twice as heavy as anything in market"

• Forum story: Guy rebuilding closet twice under weight

• Adapting heritage for warmer weather environments

• Maintaining overbuilt quality while creating lighter options

[76:30 - 80:15] Hardest Parts of the Job

• "Not rocket science, but not easy"

• Operational complexity of global apparel business

• 180-day material lead times

• Forecasting demand post-COVID era

• Managing inventory risk

[80:15 - 84:00] Building Trust & Avoiding Yes-Men

• Flat perspective on hierarchy

• Issues with authority from childhood

• Trusting subject matter experts

• "I've always felt like I had better sense than my boss"

[84:00 - 87:30] Hiring Philosophy

• Authenticity as #1 quality

• "You gotta just be yourself"

• Being best version of yourself vs. corporate contortion

• Compatibility over conformity

[87:30 - 91:45] Self-Care & Performance

• Foundation: Exercise, food, sleep, primary relationship

• In bed by 8:30-9:15 PM, up at 4:30 AM

• Sleep struggles during heavy travel years

• Hot bath routine and sauna plans

[91:45 - 95:30] Biggest Career Influences

• Lisa and Holly - Alpine shop owners who made 18-year-old Tim a manager

• First break leading to Patagonia recommendation

• Importance of people who give you chances early

[95:30 - 98:15] Book Recommendations

• "The Obstacle Is the Way" by Ryan Holiday

• Stoicism as practical philosophy (not taught in universities)

• Philosophy of living a good life

• Staying emotionally centered and focused

[98:15 - 101:30] Documentary Recommendation

• Free Solo - Alex Honnold as authentic person

• Coldplay documentary - following your bliss from teenage years

• Watching passion lead to global success

[101:30 - 103:45] Parenting Philosophy

• Hope for kids: "He loved me"

• Unconditional love creating confidence

• Camping together since infancy

• Creating lasting family memories

[103:45 - 106:00] Career Advice for Young People

• "Go to the office" - relationships require face time

• Be authentic - best version of yourself

• Choose primary relationship carefully - foundation for everything else

• Stay-at-home parents as hardest workers

🔑 Key Takeaways

1. Sell what people want, not what they need - Tim's father's transformative business advice

2. Crisis can become opportunity - Family challenges opened global career possibilities

3. Network over resume - Every job came through relationships, not applications

4. Ask questions first - Spend six months understanding before changing anything

5. Authenticity wins - Being yourself is your competitive advantage

🎯 Quotable Moments

• "People will pay a lot of money for things they want, and they want to pay the least amount possible for the things they need."

• "I don't have a CV because if you would've told me what I'd be doing 18 months in the future, I wouldn't have believed you."

• "This thing that was a big crisis for our family was also the origin of the opportunity."

• "You gotta just be yourself. You just need to be the best version of yourself."

• "Go to the office. You'll never develop relationships if you don't spend time with people."

#112 Sara Sugarman: Empathy Is Your Competitive Advantage

Sara Sugarman is the founder and CEO of Lulu and Georgia, a leading online home décor brand that democratizes access to beautiful, designer-quality furnishings at accessible prices. Coming from a third-generation design family—her grandfather founded a pioneering rug company in Los Angeles in the 1950s—Sara initially worked in magazines at O Magazine under Gayle King before joining her family's decorative carpet business. She launched Lulu and Georgia as a side project in the early 2010s, naming it after her grandfather Lou and father George, with the mission to make high-end design accessible to everyday consumers rather than just interior designers. The company experienced explosive growth, particularly during COVID-19, and has become known for its successful influencer collaborations and empathy-driven customer service. As a working mother of three, Sara leads with an entrepreneurial philosophy focused on trusting employees, avoiding micromanagement, and creating a company culture where people can make meaningful impact. Her journey represents a modern evolution of family legacy, transforming traditional design industry practices for the digital age.

In this episode we discuss:

1. Trust People and Let Them Fail

Sara's father taught her that "any decision is better than no decision" and the importance of not micromanaging. She learned that failure isn't actually failure—it leads to success and opportunity. As a leader, giving people autonomy to make decisions (even wrong ones) builds stronger, more capable teams than controlling every outcome.

2. Follow Your Passion, Not a Predetermined Path

Sara studied English and Psychology without a clear career plan, worked in magazines, and eventually found her way to entrepreneurship organically. She didn't follow traditional business school routes or entrepreneurial playbooks, proving that authentic success often comes from pursuing what genuinely interests you rather than forcing a prescribed formula.

3. Experience Trumps Formal Education

When Sara wanted to attend business school, her father refused to pay for it, telling her "if you want to learn business, you're going to work for me." She acknowledges that while she missed out on some formal skills like accounting, the hands-on experience taught her invaluable lessons that couldn't be learned in a classroom. Real-world application often provides deeper learning than theoretical study.

4. Empathy is Your Competitive Advantage

Sara's approach to customer service centers on understanding that home décor purchases are tied to important life moments—parties, new babies, family gatherings. By genuinely empathizing with customers' disappointments and taking authentic action to fix problems, you build lasting relationships that differentiate your business from competitors who treat interactions as transactions.

5. Constraints Can Force Better Decision-Making

Having three children while running a company taught Sara the power of intentional time management. Working mothers, she notes, "know how to prioritize" and "spend their time really wisely" because time is limited. Rather than seeing constraints as limitations, they can force you to focus on what truly matters and make more decisive, efficient choices in both life and business.

SHOW NOTES:

Time Stamps

[00:00 - 02:30] Family Design Legacy

• Sara's grandfather started a rug company in LA in the 1950s (Decorative Carpets)

• How her father expanded the family business into high-end design and hospitality

• Early exposure to the design world and her father's desire for her to join the business

[02:30 - 05:45] Early Career and O Magazine

• Moving to New York after college to work in magazines

• Working in circulation at First Corporation and learning direct mail marketing

• Landing at O Magazine under Gayle King and working with Oprah

• The joy of calling contest winners and announcing life-changing prizes

[05:45 - 08:15] Education and Career Philosophy

• Why she studied English and Psychology without a clear career plan

• Her father's advice against business school: "If you want to learn business, work for me"

• Learning business through hands-on experience vs. formal education

[08:15 - 12:00] Transition to Family Business

• Moving back to LA and learning the rug business through a sales rep in New York

• Understanding the high-end design world and showroom system

• Building relationships in the industry before joining the family company

[12:00 - 15:30] Key Lessons from Influential People

• Gale King's leadership style: making everyone feel heard and valued

• Oprah's influence on manifestation and "The Secret"

• Her father's leadership philosophy: "Any decision is better than no decision"

• Learning to trust people and let them fail

[15:30 - 19:45] The Birth of Lulu and Georgia

• Identifying the market gap: beautiful design at accessible prices

• The website crash on launch day from overwhelming traffic

• Balancing the side project with family business responsibilities

• The difficult decision to choose between the two businesses

[19:45 - 23:00] Early Growth and Scrappy Beginnings

• Manual processes: handwritten orders, printed shipping labels

• Building waitlists and managing inventory challenges

• The first million-dollar month celebration at The Abbey in West Hollywood

[23:00 - 27:30] Influencer Marketing Success

• Early gifting strategy with bloggers and influencers

• The first collaborative rug with Taylor Sterling that "couldn't stay in stock"

• Sarah Sherman Samuel as the "Michael Jordan for Nike" partnership

• Evolution from gifting to strategic design collaborations

[27:30 - 32:15] COVID-19 Challenges and Growth

• The pivot from planning cuts to emergency hiring in one week

• Operational challenges: being unprepared for massive growth

• Supply chain issues, white glove delivery problems, and remote work challenges

• Learning the importance of investing in infrastructure and technology

[32:15 - 36:00] Leadership and Company Culture

• Looking for "entrepreneurial spirit" as the top hiring criteria

• Building a team where 80% of leadership are working mothers

• The value of working parents: prioritization and time management skills

• Creating an environment where people can make meaningful impact

[36:00 - 40:30] What Makes Lulu and Georgia Unique

• Product-first, design-focused approach

• Not subscribing to one style but seeing beauty in all design

• Handmade products and sustainability focus

• The shift from retailer to manufacturing their own exclusive products

[40:30 - 44:15] Customer Service Philosophy

• Leading with empathy and compassion

• Understanding that home décor connects to important life moments

• The launch of free design services to help overwhelmed customers

• Positive feedback and sales impact from personalized service

[44:15 - 48:00] Work-Life Integration

• Learning to delegate after her first daughter was born

• Operating on 5 hours of sleep while managing three kids and the business

• Taking time during the day for kids, working at night

• The trade-offs of entrepreneurship and motherhood

[48:00 - 51:30] Career Advice and Entrepreneurship

• The importance of "leaning into leadership" and understanding your role

• Building trust with employees so they can grow and develop

• Not following traditional entrepreneurial playbooks or reading business books

• Finding your own organic path rather than disrupting for disruption's sake

[51:30 - 54:00] Learning from Peer Groups

• The value of entrepreneur groups for sharing experiences

• Why there's no formula for success in business or parenting

• The importance of supportive communities when making difficult decisions

• Learning from others' similar experiences

[54:00 - 56:30] Misconceptions and Future Focus

• Many people don't realize Lulu and Georgia designs and manufactures their own products

• The trade business (interior designers and architects) as a significant revenue stream

• Addressing competitors who claim to offer "Lulu and Georgia at half the price"

• Focus on quality, handmade products, and sustainability

[56:30 - 58:00] Rapid Fire Personal Questions

• Her husband's work as a comedy writer for American Dad

• No formal self-care routines or wind-down practices

• The reality of being an "in the weeds" CEO who wants to understand everything

• Why she'd love to learn coding but doesn't have the time

Key Takeaways

1. Trust and Autonomy: "Any decision is better than no decision" - let people fail and learn

2. Empathy in Business: Understanding customer emotions drives better service and loyalty

3. Experience Over Education: Hands-on learning often trumps formal business education

4. Organic Growth: Following passion and solving real problems beats following formulas

5. Working Parent Superpowers: Constraints force better prioritization and decision-making

Connect with Sara Sugarman

• Company: Lulu and Georgia

• Website: www.luluandgeorgia.com