After years of side hustles and self-doubt, Steve Young made one decision that changed everything. He began his entrepreneurial journey selling cassette tapes in grade school, but it wasn’t until he launched a niche podcast about apps that things finally clicked. In this episode, Steve shares how fear nearly held him back, how he landed his first client, and how he built a profitable agency without outside funding. It's a story about persistence, clarity, and the freedom that comes from betting on yourself.

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Episode Resources

“Extreme Ownership” by Jocko Willink and Leif Babin (https://a.co/d/e1Wvgug)

“Do Things That Don’t Scale” by Paul Graham (https://www.paulgraham.com/ds.html) 

EO Fire by John Lee Dumas - A daily podcast featuring interviews with successful entrepreneurs, focused on their journeys, lessons learned, and tactical advice for aspiring founders. (https://www.eofire.com/podcast/) 

Smart Passive Income by Pat Flynn - A podcast that explores how to build online businesses and create multiple streams of passive income, featuring strategies, case studies, and personal experiments from Pat Flynn and his guests. (https://www.smartpassiveincome.com/spi/)

When Chris Girbés left a steady job to start his own wealth practice, he wasn’t chasing scale. He was chasing meaning. In this episode, he shares what he’s learned from working with startup founders: the myth of the perfect exit, the danger of unclear goals, and the burnout that comes from tying your identity too closely to your business. Whether you're scaling or still scrappy, this conversation is packed with grounded insight on building a business while you build the life you actually want to live.

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Episode Resources

Registered Life Planner (RLP) -  A certification focused on life-first financial planning. (https://www.kinderinstitute.com/rlp-designation/) 

When Erik Stanley left the comfort of a steady paycheck and the familiarity of a running store, he didn’t just launch a business, he built a movement. In this episode, Erik shares how Trail Roots was born from a desire to coach differently, build genuine community, and carve out space on Austin’s untamed trails. He opens up about the emotional hurdles of breaking ties, the real cost of hiring wrong, the power of purpose, and why having a clear mission is the cornerstone of long-term success. Whether you’re a founder, a runner, or somewhere in between, this is one you don’t want to miss.

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Episode Resources

“Start with Why: How Great Leaders Inspire Everyone to Take Action” by Simon Sinek (https://a.co/d/548A9oO) 

“Slicing Pie” by Mike Moyer (https://slicingpie.com/) (https://a.co/d/ceQJmgs)  

The Dave Ramsey Show by Dave Ramsey / Ramsey Solutions Financial advice podcast covering entrepreneurship, debt, budgeting, and leadership. (https://open.spotify.com/show/5exfRPDNCBHmntEkJrlLmX?si=0e9911336ac64f3f) 

At just 25, Tom Williams launched his first lending business with $5,000, a dream, and a San Francisco office he secretly lived in. In this episode, Tom walks us through his unorthodox journey from boat-washing teenager to fintech founder, revealing the pivotal moments, early sacrifices, and bets that shaped his entrepreneurial path. He opens up about navigating failure, weathering the dot-com bust from inside Silicon Valley, and rebuilding from scratch to ultimately create a sustainable, values-driven business that’s thrived for over two decades. This is a story about resilience, conviction, and what it really takes to build a business from the ground up.

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Episode Resources

“The Man in the Glass” by Anonymous (https://allpoetry.com/The-Man-in-the-Glass)

“The Man in the Arena” by Theodore Roosevelt (https://www.theodorerooseveltcenter.org/Learn-About-TR/TR-Encyclopedia/Culture-and-Society/Man-in-the-Arena.aspx)

Neil Cameron’s entrepreneurial journey didn’t start in a boardroom—it started on a beach in Australia after a career in athletics came to an unexpected end. In this episode, Neil reflects on the leap from solo founder to seasoned leader, revealing the struggles of bootstrapping, the power of listening to your customers, and the hard-earned wisdom behind building the right team. With honesty and humility, he shares what it really takes to grow a business—and yourself—along the way.

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Episode Resources

The E-Myth by Michael E. Gerber (https://a.co/d/2ARcl6J)

When Tiffany Bailey stepped into her family’s sod farming business, she didn’t see herself as an entrepreneur, just someone grinding to get the work done. But nearly two decades later, she’s redefined the company, the culture, and herself as a leader. In this episode, Tiffany shares the raw truth about running and growing a business with family: the trust, the tension, and the tough calls. Hear how she navigated succession, scaled the business, embraced B2C, and built a culture rooted in clarity and care. This is a masterclass in leadership, learning, and legacy.

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Episode Resources

Check out what Tiffany is building at Bayside Sod (https://baysidesod.com)

Read more about the Full Focus Planner (https://fullfocusstore.com)

Learn more about the Culture Index (https://www.cultureindex.com)

Can a robot become your child’s best friend? Peter Fitzpatrick thinks so. In this episode, Peter, co-founder of Fawn Friends, shares the personal story that led him to build emotionally intelligent AI companions for kids. From pool party hustles in grade school to raising millions in venture capital, Peter opens up about the emotional challenges of leadership, the power of character-driven products, and why putting truth first might be the most underrated startup strategy. If you’ve ever questioned whether you’re crazy to dream this big, this one’s for you.

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Episode Resources

Stay up to date with what Peter and his team are building (https://www.fawnfriends.com)

Learn more about Vernon Howard (https://www.anewlife.org)

What happens when someone who loves being the #2 decides to take the lead? Bryan Barletta, founder of Sounds Profitable, joins the show to talk about his unlikely journey to building one of the most influential organizations in podcasting. From calling out broken systems to creating real solutions, Bryan shares how he’s challenging industry norms, creating momentum without investors, and building a business that lifts the entire space. This is a masterclass in clarity, conviction, and community-driven growth.

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Episode Resources

Iñaki joins the show to share how he turned a no-code prototype and one powerful ally into his fast-growing climate-tech startup, Climatta. He dives into the power of starting lean, why building with customer feedback is everything, and how trust—not just traction—wins investors. From co-founder dynamics to bootstrapping with nothing but a Figma file and a favor, this is a raw, insightful look at what it really takes to build something that matters.

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Episode Resources

“Only the Paranoid Survive” by Andrew Grove (https://a.co/d/acCH658)

“Predictable Revenue” by Aaron Ross (https://a.co/d/iFC7efW)

“The Mom Test” by Rob Fitzpatrick (https://a.co/d/drMFDyi)

“Crossing the Chasm” by Geoffrey Moore (https://a.co/d/9tq5mlq)

What if your biggest competition isn’t the market—but yourself? In this candid conversation, Lucia Van Den Brink recounts her journey from coding a webshop at age 11 to leading a thriving CRO agency. She shares what it was like to pause everything during maternity leave, why her first hire failed, and how embracing rejection shaped her entrepreneurial resilience. It’s a powerful exploration of self-doubt, personal values, and redefining success on your own timeline.

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Episode Resources

Get more info on Lucia’s company (https://increase-conversion-rate.com)