Season 3

In the middle of a chaotic 10x growth stretch, Ryan Heckman found himself alone in his basement at two in the morning, convinced he had a people problem. A late-night PBS interview introduced him to Brian Kight and his father Tim, and to a different diagnosis: a culture deficiency. Twenty-two years later, Brian is the founder and author of Daily Discipline, and he now builds high-performing cultures inside the NFL, the NCAA, and C-suites across industries. He and Ryan walk through why strategy rarely gets executed as designed without the culture to support it, why a written standard means nothing until it is enforced, and why one five-second decision mattered more than a twelve-month transformation. Listeners will leave with a practical way to turn stated values into standards a team actually lives by.

Mark Hopkins left a stable engineering career at HP to chase a ski trip he took as a teenager in Aspen, eventually building a medical device manufacturer from nothing to 300 employees before selling it and co-founding Rallyday. As a Managing Partner at Rallyday Partners, Mark once ran a solo investing fund built entirely on founders he met while writing a book of life lessons for his daughters, wisdom that now shapes how the firm evaluates every founder it backs. In this conversation, Ryan and Mark unpack the real difference between knowledge and wisdom, the “prosperity cycle” that turns hardship or vision into compounding momentum, and the practice of care-frontation, caring about someone enough to tell them the hard truth. Listeners leave with a six-part framework for earning the belief that you can do anything, proof that wisdom, like a good golf swing, looks effortless only after years of unseen work.

In 2016, Chris Barbin sold Appirio, the company he built from four founders to 1,500 employees, to Wipro for more than $500 million. This spring, he spent 38 days completely alone on the Pacific, rowing 1,750 miles from Monterey to Puerto Vallarta with no support boat, no sail, and no motor. Chris joins Ryan Heckman to talk about the leap from operator to private equity investor at Tercera, and the concept of drift, the miles you lose when the oars stop moving, which became his metaphor for marriage, fatherhood, and his son’s recovery from addiction. Listeners will walk away with a sharper sense of what to control and what to simply adapt to.

Karl Mecklenburg was the Swiss Army knife of the Denver Broncos defense, a six-time Pro Bowler who played all seven front positions and never told the offense where he was going. But what Ryan Heckman remembers most is how Karl walked off the field after a loss. In this conversation, they explore the leadership lessons hiding inside professional football: what it means to mentor rather than protect your own job, why decisiveness is a skill (not a personality trait), and how the framework “prepare thoroughly, perform decisively, evaluate honestly, adjust accordingly” applies as cleanly to a sales meeting as to a goal-line stand. Listeners will walk away with a reframe on failure, grit, and what thankfulness has to do with greatness.

David Gardner co-founded The Motley Fool on AOL in 1994 at age 28, with $50,000 of his own money and a belief that most people still don’t share: that ordinary investors can beat the market. In this conversation, Ryan Heckman and David trace the origins of Rule Breaker Investing, the third school of thought that sits between Bogle’s indexing and Buffett’s value discipline, and how it led Gardner to Amazon, Nvidia, and Tesla decades before the crowd arrived. They also go deep on the principles underneath the strategy: winning requires lots of losing, the most important things in business can’t be captured as numbers, and the quiet power of serving others before chasing success. Listeners will walk away with a sharper lens for how to think about risk, conviction, and what it actually means to invest like a founder.

What if the future of entrepreneurship is not Silicon Valley, but everywhere else?

In this episode of The Founders’ Journey, Ryan Heckman sits down with Linda Rottenberg, Co-founder and CEO of Endeavor. What began in Buenos Aires in 1997 has grown into a global network spanning 45+ countries, helping build companies that generate over $100 billion in revenue.

Linda shares how Endeavor transformed entire ecosystems by backing founders early and creating a powerful network effect across the world.

They also explore a core idea we believe deeply in at Rallyday: Belief Capital. Why founders need more than money, and how trust, purpose, and community drive the most enduring companies.

This is a conversation about scaling globally, leading through uncertainty, and building something that truly matters.

If you are a founder, investor, or builder, this one is worth your time.

What happens after you build the company? After the exit? After the identity you wrapped yourself in no longer fits?

In this no-BS conversation, Ryan Heckman sits down with Chip Conley, founder of Joie de Vivre Hospitality, former Head of Global Hospitality & Strategy at Airbnb, bestselling author, and founder of the Modern Elder Academy.

Chip shares how he raised $1.1M at 26 to buy a broken-down motel in San Francisco, turning it into 52 boutique hotels before selling to Hyatt. But the most pivotal chapter was not the growth. It was the unraveling. Burnout, personal loss, and a near-death experience forced him to confront a deeper question: Who am I if I am not this company?

That reckoning led him to Airbnb, where he joined as a 52-year-old mentor to Brian Chesky during the company’s meteoric rise. Together, they navigated scale versus soul, ego versus service, and what it means to lead from behind.

This episode explores the difference between knowledge and wisdom, how to reframe accountability with your team, why midlife is a chrysalis not a crisis, and how founders can move from return on investment to ripple of impact.

For founders focused on building value, this is a reminder that you are also building a life, including your own.

In this episode of The Founders’ Journey, Ryan Heckman sits down with Tony Aug, Co-founder and CEO of Nimble Gravity, one of the most sought-after data science and AI consultancies in the U.S. Known for his intensity and intellectual firepower, Tony surprises with a deeply human origin story rooted in curiosity, discipline, and heart. Tony shares how growing up in an educator household shaped his obsession with understanding how things work — and rebuilding them better. That instinct carried him from engineering and leadership roles inside massive organizations to founding Nimble Gravity, where he now helps companies turn data and AI into real, executable value. This is a conversation about leadership beyond the highlight reel: cutting through AI hype, connecting strategy to execution, and teaching organizations how to harness powerful tools without burning the house down. A must-listen for founders and operators navigating what’s changing — and what actually matters next.

In this episode of The Founders’ Journey, we sit down with Michelle Collie, Founder and CEO of Highbar Physical Therapy, to explore a story where the journey is just as personal as the objective. From a life-changing ACL injury on a basketball court in rural New Zealand to building and scaling a leading physical therapy platform alongside Rallyday, Michelle shares hard-earned lessons on leadership, purpose, and value creation. Together, we unpack how to “pull” a private equity partner, why putting teammates first leads to better outcomes, and how aggressively humble leadership can elevate an entire organization and an industry. This is a candid, inspiring conversation about growth, resilience, and building something that truly matters.