The Intentional Investor #41: Pablos Holman

Dave Nadig joins us for a wide-ranging conversation on intentional investing, creativity, career detours, near-death experiences, and building a meaningful life. From growing up as a “no-lock kid,” to working on live TV in Los Angeles, to the early days of ETFs, to a traumatic climbing accident that changed his worldview, Dave shares a remarkable story filled with lessons about ambition, humility, family, and purpose.

Pablos Holman is a legendary hacker, inventor, and investor whose career spans from rural Alaska to Blue Origin and beyond. In this episode of The Intentional Investor, Matt Zeigler explores how curiosity, creativity, and relentless experimentation shaped Pablos’s journey — from hacking onstage and pioneering early web development to building inventions that shoot mosquitoes with lasers and investing in deep-tech founders today. It’s a masterclass in innovation, persistence, and the mindset of people who make the impossible real.

Adam Butler joins The Intentional Investor with Matt Zeigler for an honest, funny, and deeply reflective conversation that traces the origins of one of investing’s most thoughtful minds. From a Dungeons & Dragons-playing kid in Newfoundland to the CIO of Resolve Asset Management, Adam’s story is about curiosity, overconfidence, failure, reinvention, and finding purpose through markets. Along the way, he shares the lessons that shaped his worldview — and the mistakes that built his philosophy on risk, humility, and growth.

Tyrone Ross joins The Intentional Investor with Matt Zeigler for a conversation that goes far beyond markets — a story of grit, purpose, pain, and love. From growing up in the projects of New Jersey to becoming an elite athlete and mission-driven financial leader, Tyrone shares how the people who filled the gaps in his life helped shape his identity and purpose. This episode explores how embracing pain, service, and faith can transform setbacks into gifts, and how personal history informs a life of intentional investing and impact.

In this episode of Intentional Investor, Matt Ziegler sits down with Danielle Strachman, co-founder and general partner of 1517 Fund, former director at the Thiel Fellowship, and lifelong supporter of unconventional paths. Danielle shares her journey from a New England upbringing and music-filled childhood to starting a charter school during the financial crisis, building 1517 to back “dropouts, renegades, and sci-fi kids,” and embracing her role as a “professional fairy godmother.” Her story is one of resilience, creativity, and building communities that make a difference.

Matt Zeigler sits down with Eric Pachman to explore how purpose, curiosity, and friendship powered an unlikely path from chemical engineering and ExxonMobil to Wall Street, data storytelling, and exposing hidden costs in healthcare. Eric shares the decisions and inflection points that shaped his life—becoming a parent during Harvard Business School, burning out and rebuilding energy as an introvert, and learning to make complex ideas useful—while offering practical frameworks for better decisions, communication, and impact.

In this episode of The Intentional Investor, Matt Zeigler sits down with Jenny Rozelle—attorney, business owner, and host of the Legal Tea podcast—to explore her journey from small-town Indiana to running a thriving law firm with her husband. Jenny shares stories of persistence, mentorship, and building a business that doubles as a community asset. From stubbornness as a superpower to balancing cattle chores with client calls, this conversation blends humor, resilience, and hard-earned lessons about investing in both life and work.

In this episode of *The Intentional Investor, Matt Zeigler sits down with Devin Anderson — CEO and co-founder of Convexitas — for a wide-ranging conversation on startups, trading desks, and the lessons learned from navigating crises. From working at an internet company in high school to winding down risk at Deutsche Bank’s “bad bank,” Devin shares an unfiltered look at technology, entrepreneurship, derivatives, and risk management.

In this episode of *The Intentional Investor*, Matt Zeigler sits down with Rupert Mitchell—global capital markets veteran, writer, and founder of Blind Squirrel Macro—for a conversation that’s equal parts myth, markets, and meaning. From working on privatization deals in Cairo and Hong Kong’s ETF debut to reflections on career reinvention, cynicism in finance, and Norse mythology, Rupert brings a rare blend of depth, wit, and global experience. If you’ve ever wondered how a Spanish literature major ends up structuring billion-dollar deals—or how a squirrel from Norse myth can explain market dynamics—this one’s for you.

In this episode of The Intentional Investor, Matt Zeigler sits down with John Stoj for a wide-ranging conversation that explores career reinvention, risk-taking, and the deeper purpose behind financial decisions. From an unexpected Wall Street entry via a summer internship, to launching a sushi business, to ultimately rethinking how investment advice should be delivered, John shares a journey filled with humility, humor, and hard-earned lessons.