Podcasts

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.

In this episode of The Founders’ Journey, we sit down with David Gilberg, Founder, CEO, and President of Elder Care Homecare, who made the bold leap from investment banking at Morgan Stanley to building a purpose-driven home care company alongside his mother. What began as a small family practice rooted in compassion has grown into a leading concierge home care provider serving more than 600 patients daily across four states.

David shares how his mother’s lifelong commitment to seniors shaped Elder Care Homecare’s unique model, one that blends social work and nursing to deliver truly human-centered care. We talk about what it took to scale from a handful of clients to thousands of caregivers, the culture that keeps quality at the center, and the purpose statement that guides every decision the company makes.

Listeners will hear powerful lessons on trading success for significance, staying grounded while growing fast, and what it means to “meet the moment” as a leader, parent, or founder. David’s journey is a reminder that real care is built one relationship, one heart at a time.

After building a thriving law firm, Denise Logan left it all behind for life on the road and found her purpose helping founders navigate one of the most emotional chapters of their lives: selling their business.

In this episode, Denise joins Ryan Heckman to explore why every exit is more than a financial transaction. It’s a reckoning with identity, legacy, and personal transformation. Drawing on her experience as both a therapist and lawyer, Denise shares the hidden emotional dynamics of selling a company—the relief, confusion, and rediscovery that follow—and reminds us that fulfillment after an exit comes from connection, purpose, and presence.

At its heart, this conversation is about new beginnings and the courage to let go. Adventure only waits for the adventurer.

In this episode of The Founders’ Journey, Ryan Heckman sits down with youth psychologist Keith Sousa to explore the tension between building companies and raising kids. Keith shares why the skills that make us effective in business don’t always translate at home, how presence matters more than perfection, and why it’s never too late to reconnect with family. At its core, this is a conversation about grace, for ourselves as parents, and for the children who are our greatest legacy.

What does it take to grow as a leader while scaling a company? In this episode of The Founders’ Journey, Ryan Heckman sits down with executive coach Ed Batista—who’s logged nearly 10,000 hours working with CEOs and founders. They explore the shift from force to power in leadership, why structure can actually create freedom, the lonely work of being a CEO, and how self-coaching can help founders sustain both performance and fulfillment.

In this episode of The Founders’ Journey, Ryan Heckman sits down with Dan Cremons, the newly appointed and sole Strategy Architect at Rallyday Partners, to explore his evolution from middle-class Cincinnati roots to becoming a transformative force in private equity – challenging industry norms with a refreshingly human-centered approach.

Dan shares his journey from Alpine Investors to founding Accelera Partners, authoring two books, and teaching at Chicago Booth. They dive into his “people working with people to do stuff for people” philosophy, why spreadsheets can’t replace leadership development, and frameworks that align organizational efforts with velocity. Tune in as Dan reveals how companies ignite when employees work at the intersection of talent, energy, and meaning – lessons learned not in boardrooms but in Louisiana warehouses and company turnarounds.

In this episode of The Founders’ Journey, Ryan Heckman sits down with Nancy Catarisano and Frank Longobardi of Insero Advisors to explore their remarkable journey from startup founders to industry leaders in the rapidly evolving accounting sector.

Nancy and Frank share insights on navigating what might be the fastest-changing professional services landscape today – balancing technological innovation with human-centered culture. They discuss the industry’s pressing challenges: workforce demographics, capital requirements for growth, and the surprising influx of private equity investment. Tune in as they reveal how their Rochester-based firm maintains small-company agility while executing with national-scale vision – proving that “unsexy” industries often drive the most exciting transformations.

In this episode of The Founders’ Journey, Ryan Heckman sits down with Vance Brown, renowned entrepreneur and civic leader, to explore his evolution from ambitious North Carolina student to Colorado software pioneer. Vance shares his remarkable journey through three successful software ventures – from family-run Buildsoft to billion-dollar FrontRange Solutions to bootstrapped Cherwell Software.

Vance reveals the emotional undercurrents of entrepreneurship – from early competitive drive to debilitating burnout – and his pivotal shift from success to significance. They discuss how personal crises became catalysts for growth, the spiritual dimensions of leadership, and how Vance transformed Colorado Springs’ tech ecosystem through Exponential Impact and the National Cybersecurity Center. Tune in for profound insights on building companies with purpose and finding meaning beyond achievement.

The Founders’ Journey: Special 3-Part Series, Tariff Talks
In April 2025, sweeping new tariffs triggered market turmoil, shook CEO confidence, and sparked urgent questions across the business landscape. At Rallyday, we responded the way we did during COVID – by calling trusted voices on the front lines. And this time, we hit record.

In just 48 hours, we captured three candid conversations exploring this moment from every angle:

• Wall Street (macro + markets)
• Main Street (operations + strategy)
• Your Street (mindset + leadership)

All three episodes are available now — no politics, no punditry. Just clarity, curiosity, and practical insight to help you lead through what’s next.

Part 3: Your Street with Brian Kight, Author of DailyDiscipline.com

The final chapter in our series hits closest to home — your street, your team, and your mindset. Longtime Rallyday partner and performance coach Brian Kight joins us for a riveting discussion on what it really means to lead during uncertainty. Brian doesn’t just offer platitudes — he delivers frameworks. He reframes adversity as opportunity, reminds us that belief follows action (not the other way around), and makes a compelling case for why the real competition right now is between disciplined responders and emotional reactors. This episode is for the leader in the mirror — the one whose response will define your team’s future.

The Founders’ Journey: Special 3-Part Series, Tariff Talks
In April 2025, sweeping new tariffs triggered market turmoil, shook CEO confidence, and sparked urgent questions across the business landscape. At Rallyday, we responded the way we did during COVID – by calling trusted voices on the front lines. And this time, we hit record.

In just 48 hours, we captured three candid conversations exploring this moment from every angle:

•  Wall Street (macro + markets)
•  Main Street (operations + strategy)
•  Your Street (mindset + leadership)

All three episodes are available now — no politics, no punditry. Just clarity, curiosity, and practical insight to help you lead through what’s next.

Part 2: Main Street with Tim Van Mieghem, Co-Founder & Partner of The ProAction Group

In Part 2, we shift from Wall Street to Main Street, where the ripple effects of tariffs are being felt in real time by business owners, operators, and the teams that keep America running. Ryan is joined by Tim Van Mieghem, Co-founder & Partner of The ProAction Group and a nationally recognized supply chain expert for private equity-backed companies, to discuss how leaders are adapting to sudden cost increases, sourcing disruptions, and shifting customer demand. Tim shares a deeply grounded framework for seeing clarity, acting decisively, and even using this crisis to create lasting culture change. He reminds us why operational excellence is still the ultimate lever — and how relationships, not spreadsheets, will determine who wins in this new era. Whether you’re a CEO, an operator, or an investor, you’ll walk away with actionable insights for steering your organization through uncertainty.

The Founders’ Journey: Special 3-Part Series, Tariff Talks
In April 2025, sweeping new tariffs triggered market turmoil, shook CEO confidence, and sparked urgent questions across the business landscape. At Rallyday, we responded the way we did during COVID – by calling trusted voices on the front lines. And this time, we hit record.

In just 48 hours, we captured three candid conversations exploring this moment from every angle:

•  Wall Street (macro + markets)
•  Main Street (operations + strategy)
•  Your Street (mindset + leadership)

All three episodes are available now — no politics, no punditry. Just clarity, curiosity, and practical insight to help you lead through what’s next.

Part 1: Wall Street with Jacob Manoukian, Head of U.S. Investment Strategy of J.P. Morgan Private Bank

In this first episode of our special three-part series, we sit down with Jake Manoukian, Head of Investment Strategy at JP Morgan, for a candid look at how the financial markets have responded to the April tariff shock. Jake offers more than just a Wall Street analyst’s perspective — he brings rare clarity and historical context to this moment, drawing fascinating parallels to the early days of COVID and offering a steady-handed interpretation of what market volatility is really telling us. This is a masterclass in decoding noise versus signal, understanding what’s driving CEO confidence downward, and identifying the scenarios — good, bad, and middling — that may lie ahead. If you’ve been struggling to connect Bloomberg headlines to boardroom decisions, this conversation is the perfect place to start.

Jake brings a rare perspective-combining global insight, deep client experience, and a gift for translating macro events into practical takeaways. This conversation isn’t about politics or blame; it’s about understanding what’s really happening and how leaders can best position themselves and their organizations for what comes next.