The Founders' Journey

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.Chip Conley is not an investor in one or more of Rallyday Partners private funds and did not receive any cash or non-cash compensation for participating in this podcast.To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com

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.Tony Aug is not an investor in one or more of Rallyday Partners private funds and did not receive any cash or non-cash compensation for participating in this podcast.To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com

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.Michelle Collie is not an investor in one or more of Rallyday Partners private funds and did not receive any cash or non-cash compensation for participating in this podcast.To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com

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.David Gilberg is not an investor in one or more of Rallyday Partners private funds and did not receive any cash or non-cash compensation for participating in this podcast.To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com

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.Denise Logan is not an investor in one or more of Rallyday Partners private funds and did not receive any cash or non-cash compensation for participating in this podcast.To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com

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. Keith Sousa is not an investor in one or more of Rallyday Partners private funds and did not receive any cash or non-cash compensation for participating in this podcast.To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com

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. Ed Batista is not an investor in one or more of Rallyday Partners private funds and did not receive any cash or non-cash compensation for participating in this podcast.To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com

Dan Cremons, founder of Accelera Partners and a seasoned strategy architect, shares his inspiring journey from Cincinnati to the forefront of private equity. He emphasizes a human-centered approach, arguing that spreadsheets can't replace effective leadership. Discussing his books, he highlights the synergy between talent, energy, and meaning within organizations. Cremons also explores the importance of a value creation mindset in business education, advocating for a curriculum that fosters genuine engagement and personal fulfillment in the workplace.

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.Frank Longobardi & Nancy Catarisano are not investors in one or more of Rallyday private funds and did not receive any cash or non-cash compensation for participating in this podcast.To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com

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.Vance Brown is not an investor in one or more of Rallyday private funds and did not receive any cash or non-cash compensation for participating in this podcast.To nominate a founder or to nominate yourself as a future guest speaker on our podcast, please submit your nominations here. www.RallydayPartners.com