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 an...

Garth Martin didn't grow up around investment bankers. He grew up around a flooring installer, in his parents' small business outside Philadelphia, and he still describes his job as being a real estate agent for companies. In this episode, Garth Martin of Envoy Capital Advisors joins Ryan Heckman to talk about building a career from a non-target school and a CPA background, the "aggressive humility" that defines great advisors, and the accelerating race between AI labs and the services firms ...

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 m...

Kevin Palamara has spent his entire 24-year career at one firm, a rarity in investment banking, and it shows. As a Managing Director at Provident Healthcare Partners, Kevin has been on the front lines of the private equitization of American healthcare, from fax-machine deal rooms in 2002 to today's fiercely competitive physician practice markets. In this conversation, Ryan and Kevin unpack the sectors moving fastest right now (oncology, urology, retina), the difference between referral-driven...

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 "pre...

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 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 underne...

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 t...

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 m...

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 ...

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 pu...