Chris Cleveland, Head of School at Wesleyan, looks back on the worst advice he ever got: “Do what makes you happy.” On the surface, it sounds harmless—even good. But in this episode of The Worst Advice I Ever Got, Chris explains how chasing happiness alone can lead to shallow choices, and why purpose, responsibility, and faith create something deeper and more sustaining. It’s an honest conversation about leadership, values, and the difference between living for happiness and living for meaning.

Kyle followed that rule for years, becoming a decorated airline pilot by shutting his feelings down. But eventually he realized the truth: every decision we make, whether in the air or on the ground, is fueled by emotions. Suppressing them doesn’t make us stronger, it makes us weaker. In this episode, Kyle shares how unlearning that advice changed his career, his relationships, and his entire approach to leadership. We talk about emotional intelligence, stress as a superpower, why control is a myth, and why real leaders act more like lighthouses than tugboats. It’s a conversation for anyone who’s been told to “tough it out” or “leave feelings at the door.” Turns out, emotions aren’t the problem. They’re the key.

“The worst advice I ever got was, exercise more and eat less.” Sammy Williams shares how that advice, repeated over and over, became a damaging mantra that pushed him toward unhealthy extremes and left him battling shame around his body. What sounds simple on the surface was actually harmful, and it took years for him to unlearn it. In this episode, Sammy opens up about his journey to rebuild a healthier relationship with food, exercise, and himself, and why quick-fix advice can do more harm than good. It is a candid and powerful conversation about healing, self-acceptance, and finding balance beyond the scale. Hosted by Sean Taylor, produced by JB, and made possible by Smith + Howard.

What happens when the world tells you, “You don’t have to be smart if you’re pretty”? In this episode, Teresa Caro opens up about the dangerous advice she got early in her career—and how it fueled her drive to prove her worth beyond appearances. From shifting life stages to reinventing herself through every chapter, Teresa shares hard-earned wisdom on: Breaking free from superficial expectations Redefining success as you grow and evolve Building value that lasts longer than looks It’s an honest, funny, and deeply human conversation about turning bad advice into good stories—and finding your own path forward. ️ Hosted by Sean Taylor, produced by JB, and made possible by Smith + Howard.

What happens when the person you admire most tells you you’re not good enough? For John Follis, it was a college professor who pulled him aside and said: “You suck at advertising. You should quit.” At 20 years old, chasing a new dream, those words almost knocked him off course. In this episode, John shares how he pushed past that moment, built resilience through setbacks—including getting fired four times—and eventually co-founded one of the hottest creative agencies on Madison Avenue. His work won awards, landed press in The New York Times and Wall Street Journal, and made him a “secret weapon” for big brands.

In The Karate Kid, the bad advice was “show them who’s boss.” For Matthew Eyers, it wasn’t a movie—it was the real message he was given early on. In this episode of The Worst Advice I Ever Got, Matthew unpacks how that mindset shaped his choices, why it led to more harm than good, and what he’s learned about leading with something stronger than ego.

What if “time heals all wounds” was the worst advice you could take? Clarity consultant Kyle Smith breaks down why healing is an active process, not a waiting game, and shares practical steps to turn pain into personal power.

In this episode, Chris shares how avoiding conversations about salary, business finances, and expenses keeps us stuck — and how transparency, experience sharing, and breaking the link between money and self-worth can lead to clarity, better decisions, and deeper relationships.

This week, Michael Brody-Waite shares how that well-meaning message failed him—leading to homelessness, addiction, and hopelessness by age 23. But what happened next is extraordinary. Through a 12-step program, Michael not only recovered—he built a new life from the ground up. He went from sleeping on floors to building a company that grew 20,000%, making the Inc. 500 list, and delivering one of the most-watched TEDx talks of all time. In this episode, he opens up about: Why telling addicts to “just stop” isn’t enough The 3 principles that saved his life—and made him a better leader How addiction and executive burnout have more in common than you think What families should do when someone they love is struggling It’s one of the most powerful stories we’ve shared—raw, honest, and packed with insight for anyone facing discomfort, fear, or change.

When Tom Rebers was told to "charge the going rate," it sounded safe and reasonable. But playing it safe nearly cost him his business. In this episode of The Worst Advice I Ever Got, Tom shares how he learned to set his own value, stop following industry norms, and build a business that actually works for him. If you’ve ever underpriced yourself or felt stuck following “what everyone else does,” this one’s for you.

Zahra is a licensed therapist who now works with psychedelic-assisted therapy, particularly ibogaine, a plant medicine with powerful anti-addiction effects. In this episode, she shares her journey from traditional treatment centers to becoming an advocate for spiritual, mental, and emotional healing through plant medicine. We talk about outdated recovery models, the stigma surrounding psychedelics, the role of spirituality in therapy, and why systems built on fear often fail the people who need help most. This one isn’t about promoting psychedelics—it’s about listening to a story that challenges assumptions and opens up a bigger conversation. If you’ve ever questioned the rules you were taught to follow, this episode is for you.

That’s the worst advice Jeremy Schneider ever got — and it’s everywhere. From the headlines to social media, we’re taught investing means timing markets, chasing trends, and hoping for quick wins. Jeremy says that’s exactly why most people stay broke. Jeremy is the founder of Personal Finance Club, a former tech entrepreneur who retired at 36, and now teaches simple, proven ways to build wealth. In this episode, he breaks down:✅ Why ‘boring’ index funds beat the hype✅ The two rules that actually make you rich✅ Why most millionaires just… set it and forget it✅ How to avoid the “speculation trap” that derails so many people If you’ve ever felt investing is too complicated or too risky — this episode is for you. Listen now and see why the most effective path to wealth is the least flashy.

In this episode, Joe Van Hoose talks about the messy reality of modern journalism: we need it more than ever, but the world we’ve built makes it harder than ever to do it well. Good reporting takes time, curiosity, and integrity — but today’s incentives scream: click fast, publish faster, aim later. It’s fire, ready, aim — and real journalists get burned in the process. If you care about how stories shape our world (and who gets to tell them), this conversation might frustrate you… and wake you up.

Sean and JB breakdown the episodes we've heard so far in this mini episode of the show during our week off celebrating our home nations independence!

Alison Bladh was told, like many of us growing up, that what you eat has nothing to do with your hormones. Turns out, that advice wasn't just wrong. It was harmful. In this episode, the nutritional therapist and hormone health expert breaks down how endocrine disruptors in ultra-processed foods affect everything from your energy and mood to your skin and metabolism. She shares her personal story of struggling with acne, misinformation, and eventually finding healing through food.

Kevin Palmieri was told, “Why don’t you think less?”—a dismissive response to his deep self-reflection during a personal crisis. In this episode, he shares how that moment collided with suicidal thoughts, external success, and a drive for meaning. Instead of shutting off his mind, Kevin leaned into self-awareness, using it to build a purpose-driven business and a healthier life.

In this episode, Allan shares how embracing, and eventually outgrowing,that advice led him to become one of the most influential voices in the accounting world. It’s a story about finding your lane, then building a whole new highway.

In this episode of The Worst Advice I Ever Got, Kelly opens up about the damaging pursuit of perfection. From early praise that reinforced unrealistic standards to the hidden toll it took on her mental health, she shares how striving to be flawless actually helped her succeed... and why that made it even harder to let go. This one’s for anyone who’s ever felt like their worth depends on never messing up. 

Jeff Hilimire was told to “dream big.” Sounds like great advice—until it nearly burned him out. In this episode, Jeff shares how chasing massive goals led to overextension, failed ventures, and a lesson he now lives by: dream small. Focus on what matters. Build with purpose. And grow from there. From launching startups to founding 48in48, Jeff’s story is a masterclass in scaling back to move forward.

In this episode of The Worst Advice I Ever Got, Jamie shares why traditional business plans can be a trap for creative entrepreneurs. From freelance life to launching multiple ventures, he talks about embracing uncertainty, staying agile, and why “figuring it out as you go” isn’t failure—it’s freedom. Whether you’re a planner, a dreamer, or somewhere in between, this episode will make you rethink the way you start something new. New episodes every Friday. Subscribe and follow to never miss a bad idea turned good.