#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.