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Season 2

October 7, 2025

S2 E12: Keith Sousa, MA, CAS, Owner & Therapist of Child and Adolescent Behavioral Supports and Adult Psychological Supports

In this episode of The Founders’ JourneyRyan 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. 

September 9, 2025

S2 E11: Ed Batista, Founder & Executive Coach of Ed Batista Executive Coaching

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.

August 5, 2025

S2 E10: Dan Cremons, Founder of Accelera Partners

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.

June 24, 2025

S2 E9: Frank Longobardi, Executive Chairman of the Board & Nancy Catarisano, Founder & CEO of Insero Advisors

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.

June 3, 2025

S2 E8: Vance Brown, Executive Elder at Thrivers Leadership Institute

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.

May 1, 2025

S2 E7: Tariff Talks: A Special 3-Part Series — Part 3: Your Street with Brian Kight, Author of DailyDiscipline.com

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.

May 1, 2025

S2 E6: Tariff Talks: A Special 3-Part Series — Part 2: Main Street with Tim Van Mieghem, Co-Founder & Partner, The ProAction Group

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.

May 1, 2025

S2 E5: Tariff Talks: A Special 3-Part Series — Part 1: Wall Street with Jake Manoukian, Head of U.S. Investment Strategy, J.P. Morgan Private Bank

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.

April 1, 2025

S2 E4: Tameem Hourani, Founder & Principal of RapDev

In this episode of The Founders’ JourneyRyan Heckman sits down with Tameem Hourani, Founder & Principal of RapDev, to explore his bold journey from Bahrain to Boston and from Wayfair engineer to tech entrepreneur. 

Tameem shares how he launched RapDev while still at Wayfair, scaling it into one of the fastest-growing IT consultancies - without any outside funding. They dive into the realities of bootstrapping, embracing mistakes, and maintaining the mindset of “always being a startup.” Tune in for a backstage pass to true entrepreneurship.

March 4, 2025

S2 E3: Dan Caruso, Managing Director of Caruso Ventures; Founding CEO & Chairman of Zayo Group

In this episode of The Founders’ Journey, we sit down with telecommunications titan Dan Caruso, founder of Zayo Group and author of the newly released book Bandwidth.

Known as "The Bear" for his intense leadership style, Dan shares how he built Zayo from zero revenue in 2007 to a telecommunications powerhouse with $1 billion in EBITDA, culminating in a $14 billion valuation when he stepped away in 2020 to lead Caruso Ventures.

Beyond the impressive business metrics, Dan opens up about the personal side of entrepreneurship - his vulnerabilities, struggles, and mistakes. As fierce as he is in the boardroom, Dan reveals his softer side as a devoted father, husband, and champion of Colorado's entrepreneurial community.

Join us for an intimate conversation with one of our most successful guests as he shares his entrepreneurial wisdom and the personal journey behind building a telecommunications empire.