In this episode of Skin in the Game, Saxon Baum sits down with Brian Hollins, co-founder of Collide Capital, for a wide ranging conversation on venture capital, institutional fundraising, and the mindset required to build a differentiated early-stage firm.

Brian’s story begins just outside Washington, D.C., where he grew up as the oldest of three brothers in a disciplined and competitive household. His middle brother, Mack Hollins, famously received no college football offers, walked on at UNC, and went on to build a nine-year NFL career that includes a Super Bowl championship. His youngest brother served in the Marines. That foundation of resilience, accountability, and high standards continues to shape Brian’s approach to leadership and investing.

The conversation traces his path from Stanford, where a culture of ambition and innovation pushes students to think boldly, to Goldman Sachs, where he helped build the Emerging Entrepreneurs Coverage Group. During that time, he learned how to create real value for founders before ever writing a check, including early work supporting companies like Plaid. Those experiences laid the groundwork for how he thinks about venture capital today.

Brian also explains why he approached business school intentionally, using it as a strategic platform to build relationships and lay the foundation for launching Collide Capital. The discussion highlights the difference between raising a fund and building a firm, and what it takes to earn long-term institutional LP support.

The episode concludes with a look at Collide Capital’s investment focus on fintech infrastructure, supply chain and logistics, and the future of Gen Z in the workforce and why the best founders are relentlessly focused on solving one core problem.

A thoughtful and candid discussion on building with intention and playing the long game. Tune in to this episode. You don’t want to miss this one!

The founder behind Orlando's first unicorn, Stax, and now, Worth AI, join sus on a new episode of Skin in the Game. Suneera Madhani shares her scrappy story of turning a dream into a billion-dollar fintech business with her brother, exiting their first company together, and how they landed on the idea for their latest venture, an AI-based onboarding & underwriting workflow automation platform, where she currently serves as Chief Evangelist Officer.

Suneera also shares about founding CEO School, a podcast and platform giving women the "Have-It-All" formula to scale like real CEOs, and offers some secrets as to why second-time founders move faster. They discuss how AI can enable leaner teams with outsize output and zero in on why Suneera remains deeply passionate about building in Florida.

This episode of Skin in the Game features a deep, candid conversation with Felix Hartmann, founder of Hartmann Capital on what it really means to build and invest at the frontier of technology.

Felix’s story starts long before hedge funds and venture capital. He moved to the U.S. from Germany during the 2008 financial crisis, initially planning to stay for just a year. That plan changed quickly. Early exposure to markets, coding, and emerging technology led him down a path of trading, crypto infrastructure, and eventually founding his own firm and launching Hartmann Capital the same day he signed his first apartment lease.

A major theme throughout the episode is conviction through firsthand experience. Felix doesn’t invest from a distance. He tests products, uses them extensively, and looks for signals that can’t be captured in a pitch deck. Whether it’s VR games, smart glasses, or brain computer interface technology, he believes the clearest insight comes from being a real user and understanding how a product fits into daily life.

The conversation explores why Felix shifted away from liquid crypto trading and toward long-term venture investing in frontier categories like VR, spatial computing, wearables, and neural interfaces. He explains how hardware limitations slowed VR adoption, why smart glasses may be closer to a breakout moment, and how enterprise use cases often precede consumer adoption. The discussion also touches on sub-vocal communication technology that allows people to interact with devices without speaking out loud and why it could fundamentally change how humans interface with machines.

Saxon and Felix also discuss the realities of investing on the “bleeding edge,” where traditional metrics don’t exist and patience is required. Felix breaks down how power-law outcomes often come from non-consensus bets and why underfunded categories tend to attract the most mission-driven founders.

The episode closes with reflections on geography, talent, and ecosystem building from Florida’s role in capital formation to the continued importance of Silicon Valley and Los Angeles for early-stage innovation.

In this episode, we sit down with Mike Collins, Founder and CEO of Alumni Ventures, to explore how venture capital is evolving and why network-driven investing is becoming increasingly powerful. Mike shares the origin story of Alumni Ventures and how it grew from a small alumni-based experiment into one of the most active venture platforms in the world, backing hundreds of companies across stages, sectors, and geographies.

The conversation dives into how Alumni Ventures approaches investing without leading rounds, instead partnering alongside top-tier venture firms while leveraging a global network of investors, operators, and founders. Mike explains how this “connected capital” model creates value beyond the check and why collaboration, rather than competition, is core to the firm’s strategy.

We also touch on broader trends shaping the future of venture capital, including artificial intelligence, energy innovation, healthcare, and the globalization of entrepreneurship. Drawing on decades of experience as both an operator and investor, Mike offers a thoughtful perspective on long-term thinking, governance, and what truly drives successful outcomes in venture backed companies.

This episode offers a behind-the-scenes look at a modern VC model, with insights that are relevant for founders, investors, and anyone curious about where innovation and capital are headed next.

We sat down with Andrew Wright, founder of Franklin Street, for a fascinating conversation about market dynamics, building resilient businesses, and the future of the Tampa Bay region.

Andrew shared how he launched Franklin Street at 26 and grew it into a full ecosystem of real estate services from capital markets and leasing to insurance and property management. He talks about why diversified revenue streams matter, especially in industries that ebb and flow with economic cycles.

We also unpacked today’s commercial real estate environment. Andrew describes the moment as a “rain delay” transactions are slow, liquidity is tight, and valuations are still adjusting after rapid interest-rate hikes. Even so, Florida remains uniquely strong thanks to continued population and capital migration. As lenders start pushing stalled assets toward resolution, he believes new opportunities will emerge.

Beyond market trends, Andrew shared insights on scaling teams, building culture, and developing young talent. His emphasis on authenticity, mentorship, and long-term potential over static skill sets is a refreshing and realistic take on leadership today.

We also explored the future of Westshore, including transportation needs, density, and how thoughtful planning could unlock the next phase of growth for the district. Add in his perspective on AI’s impact on real estate operations, and this episode covers a ton of ground.

If you're interested in real estate, leadership, or Tampa’s economic evolution, this is a must-listen.

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What started as one grandson helping his Papa has grown into one of the most innovative companies in healthcare today. In our latest podcast episode, we sit down with Andrew Parker, the founder and CEO of Papa, to explore how a deeply personal family moment sparked a nationwide mission to combat loneliness, support caregivers, and redefine what it means to care for aging adults.

Andrew’s story begins with a need familiar to many families: his grandfather simply needed a little help and a little company. Instead of relying on the traditional caregiving model, Andrew wondered, What if we could make companionship more accessible, more human, and more joyful? That question became the foundation for Papa, a platform connecting older adults with “Papa Pals,” a modern, community-driven approach he perfectly describes as “grandkids on demand.”

In the episode, Andrew walks us through the early days of the idea, how he tested the concept, what he got wrong, and the surprising ways people responded. He opens up about the challenges of building a company in a space where emotional connection matters as much as logistics, as well as the pressure and responsibility that come with serving some of the most vulnerable members of our communities.

You’ll hear how Papa navigated fast growth, shifting market conditions, and the complexities of working with major health plans. Andrew also shares what he’s learned about leadership, resilience, and why the “kindness economy” may be the next frontier for healthcare innovation. His insights offer value not only to founders and operators, but to anyone curious about how a mission-driven business can scale without losing its heart.

This episode is a reminder that groundbreaking companies don’t always come from flashy tech or radical disruption, they’re often built from empathy, lived experience, and a desire to solve real problems for real people. Andrew’s journey proves that when you focus on creating meaningful human connections, the impact can reach far beyond what you imagined.

If you’re interested in aging, healthcare innovation, founder stories, or simply love hearing how a small spark can turn into something transformative, this is an episode you won’t want to miss.

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In this episode of the Skin in the Game podcast, Saxon Baum sits down with Eric Bahn, co-founder of Hustle Fund, to explore the art and science of investing in pre-seed startups. Eric shares his personal journey from growing up as the son of Korean immigrants in Detroit, Michigan, to becoming a media founder and early-stage investor in Silicon Valley. His story highlights the value of persistence, humility, and learning from failure, a mindset he believes is critical for both founders and investors.

Eric emphasizes that great founders “look like anyone and come from anywhere.” While Silicon Valley has historically dominated the venture ecosystem, he notes that secondary and tertiary markets are now producing founders just as capable, thanks to the democratization of knowledge via the internet. Eric also points out a subtle but important distinction: founders from Silicon Valley often carry a relentless “grow fast, break things” mentality that accelerates execution, yet this mindset is increasingly being adopted across the country.

Hustle Fund takes a unique approach to investing, prioritizing hustle and execution over pedigree. Eric shares stories of candidates and founders who defied traditional expectations, one high school dropout who became a 100x operator, and a Princeton-educated engineer who couldn’t deliver. For Eric and his team, pre-seed investing is akin to hiring: it’s about identifying grit, determination, and the ability to learn quickly. Hustle Fund typically writes initial checks of $150,000 and pairs founders with growth projects and mentors to test their capabilities. About 20% of these teams receive a follow-up investment of $200,000. This model allows Hustle Fund to support hundreds of founders while remaining valuation-conscious.

Eric also highlights the influence of founders’ backgrounds, particularly in the service industry. Experiences as bartenders, waitstaff, or customer service agents cultivate resilience, emotional intelligence, and sales skills qualities that translate into startup success. For Eric, this aligns perfectly with the fund’s philosophy of backing “hustlers,” regardless of formal credentials or pedigree.

The conversation also dives into the role of media in venture capital. Eric explains how Hustle Fund leverages newsletters, events, and founder communities to provide value beyond capital, helping founders generate awareness, mentorship, and early revenue. This approach reflects the evolution of venture investing from a purely financial transaction to a hands-on, service-oriented partnership.

Finally, Eric shares insights into managing an expansive portfolio of 620 companies across four funds. Hustle Fund uses sophisticated data systems and a network of mentors to track growth, assess progress, and double down on top performers efficiently.

Reflecting on the culture of failure in Silicon Valley, Eric notes that “When someone starts a company here and it doesn’t work out, the first question isn’t, ‘Why did you fail?’ but, ‘What did you learn, and when will you try again?’” This mindset, he believes, is essential for innovation and entrepreneurship.

This episode offers an invaluable look at what it takes to succeed as a founder and investor in today’s pre-seed ecosystem, highlighting hustle, resilience, and the evolving dynamics of venture capital.

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On this episode of Skin in the Game, Saxon Baum sits down with longtime friends and powerhouse entrepreneurs Nick Friedman and Omar Soliman, the co-founders of College Hunks Hauling Junk & Moving and Trash Butler. From detention in high school to becoming nationally recognized leaders, Nick and Omar share the raw story behind building two iconic brands from scratch.

They talk about what it really means to bootstrap a company, the sleepless nights and skepticism they faced early on, and how they turned a beat-up cargo van into a viral, multi-million-dollar business. Along the way, they share how franchising became both their greatest challenge and smartest growth strategy, why brand and PR were everything, and the lessons they learned about scaling people, culture, and systems.

The conversation dives deep into Tampa’s rise as an entrepreneurial hub and why they believe the city’s collaborative spirit gives it a unique edge. They also open up about the evolution of Trash Butler, how raising outside capital differed from their bootstrapped journey, and what it’s really like answering to a board after running their own show for so long.

This episode is full of entrepreneurial wisdom, gritty stories, and quotable one-liners—from “teams win championships, families watch them” to “bootstrapping is the MBA, raising capital is the rocket fuel.”

If you’re an entrepreneur, investor, or simply curious about what it takes to build enduring businesses from the ground up, this conversation with Nick and Omar is a masterclass you won’t want to miss.

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Hosted on Acast. See acast.com/privacy for more information.

What separates the top 1% of venture capitalists from the rest? For Roger Ehrenberg, Managing Partner at Eberg Capital, it’s the ability — and the appetite — to invest before the crowd, before the product is built, and before there’s even proof of concept. In a recent episode of the Skin in the Game VC podcast, Roger joined Tom Wallace and Saxon Baum to share how he turned a late-career pivot into one of the most impressive track records in early-stage venture capital.

Roger didn’t come from the startup world. He spent nearly two decades on Wall Street, running billion-dollar trading desks at Citi and Deutsche Bank. From the outside, it looked like a career anyone would want — but for Roger, it had run its course. Tired of internal politics and craving something more entrepreneurial, he walked away. Around the same time, he’d been dabbling in angel investing on the side. That small experiment — backing builders before product-market fit — quickly turned into a full-time obsession.

He began writing a blog, Information Arbitrage, to share his thinking publicly. The blog gained traction. Founders started reaching out. Other investors began to follow his thesis. At a time when the idea of a “New York tech ecosystem” was almost laughable, Roger had the clarity to see where it could go — and the conviction to act. By early 2010, he scraped together a $17 million first close. That first fund would eventually land at $50 million, and IA Ventures was born.

But the money was only part of the story. What set Roger apart then — and still does — is how early he’s willing to go. He prefers backing companies before the market even knows they exist. In fact, he often writes the first check before there’s a line of code written. This isn’t blind optimism. It’s founder-first investing grounded in deep research and sharp intuition.

Roger’s track record speaks for itself. He was an early backer of The Trade Desk when it was just a deck. He seeded Datadog, TubeMogul, and multiple other companies before they became category leaders. The common thread? Founders who could not only see the future but build their way into it. To Roger, great founders share something intangible: what he calls “aesthetic and empathy.”

“Great founders understand where their product stops and where the customer starts,” he said. That could mean designing APIs that developers love or building consumer apps that feel inevitable. Either way, the best founders have an intuitive sense of product, user behavior, and market timing. Roger knows how to find them — or maybe, they know how to find him. That’s the power of publishing, he says. His blog didn’t just clarify his thesis — it attracted the right people. It helped him raise a fund when few believed in early-stage investing outside Silicon Valley.

Since then, IA Ventures has grown to four funds and backed dozens of successful startups. Roger has since passed the torch to his partners and launched his next chapter: Eberg Capital. Now, he invests alongside his sons in a new wave of innovation — spanning sports, media, entertainment, and the evolving world of fandom.

But whether he’s backing a Marlins ownership stake, investing in Formula 1, or writing angel checks to creator economy startups, one thing hasn’t changed: Roger Ehrenberg still goes early. He still backs founders before the world sees their potential. And more often than not, he’s right.

Listen to the full episode with Roger Ehrenberg now.

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