Skin in the Game VC Podcast

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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A-lign founder and CEO Scott Price joins Tom Wallace and Saxon Baum to unpack the “all gas, no brakes” journey behind building a category leader in cybersecurity compliance. Scott traces his roots from Arthur Andersen and the Enron fallout to bootstrapping through 2009, landing the first clients, and evolving from SOC 2 mainstay to a broader, tech-enabled platform. He shares candid lessons from a re-traded 2017 deal, why outside capital served as market validation, and how partnering with FTV and later HG set the stage for scale enterprise expansion, European growth, and smart M&A. We dig into frameworks over tools for AI risk, the rise of CMMC and federal standards, and how Tampa’s defense ecosystem fuels elite cybersecurity talent. Plus, leadership chemistry with a CFO, why second acts aren’t automatically easier, and a lightning round on Bitcoin, AI’s job impact, and the China tech challenge. A masterclass in grit, governance, and growth forward.

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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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On the latest episode of Skin in the Game VC, Saxon and Tom sit down with Rohan Shah, co-founder of Extend, for a conversation that blends grit, humor, and sharp insight into building in tech. Rohan shares his journey from growing up in the Bay Area with entrepreneurial parents to launching his first startup out of Stanford, and eventually co-founding Extend—a platform modernizing the extended warranty and protection plan space.

He dives into the early challenges of startup life, why his time at BCG taught him how to build for the enterprise, and how a Sunday football lineup and a conversation with a DraftKings exec sparked the idea behind Extend. What started as a playful concept around insuring fantasy sports lineups evolved into a fast-scaling company that now partners with major brands like Peloton and Brilliant Earth.

Rohan gets candid about raising $260M from SoftBank during the ZIRP era, making hard calls early, and steering Extend toward profitability.

Whether you’re a founder, investor, or just love a great startup story—this one’s worth a listen.

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In this episode of the Skin in the Game podcast, we sit down with Stu Sjouwerman, founder and CEO of KnowBe4, to discuss how he built one of the world’s most successful cybersecurity startups from the ground up.

KnowBe4, headquartered in Clearwater, Florida, is a cybersecurity training company focused on mitigating human risk through simulated phishing, user training, and real-time alerts. Today, it generates over $500 million in annual recurring revenue (ARR)—but it started in a 10x10 office, with no external funding.

Stu breaks down how he identified a massive market gap: most cyberattacks aren’t due to software vulnerabilities—they’re the result of social engineering and human error.

He shares how ransomware attacks in 2013 created a turning point for KnowBe4, propelling the startup into hypergrowth. His strategy? Move fast, market smart, and keep the product simple and sticky.

Stu also dives into:

• The future of SaaS in the age of AI
• How KnowBe4 is evolving into a platform company
• Why AI and quantum computing will trigger “company extinction events”
• His belief that LLMs are already a commodity, and the future lies in vertical AI agents

For founders and VCs alike, the episode offers a wealth of insights on startup scaling, product-market fit, and what investors should look for in repeat entrepreneurs.

Whether you're a founder, cybersecurity professional, or angel investor, this conversation with Stu Sjouwerman is a must-listen.

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In the latest episode of Skin in the Game VC, hosts Tom Wallace and Saxon Baum sit down with Jenny Friedman, the solo General Partner of Four Acres Capital, to discuss her path into venture capital, investment strategy, and what’s happening in today’s fast-moving startup world.

From Goldman Sachs to Running Her Own VC Fund, Jenny’s journey into venture capital wasn’t linear. After growing up in New York City, attending Horace Mann, and studying at Penn, she began her career in investment management at Goldman Sachs. But she quickly realized that traditional finance wasn’t for her and pivoted to the startup world, joining MiniBar Delivery, a liquor marketplace. This hands-on tech experience gave her the edge she needed to transition into venture capital.

While pursuing her MBA at Columbia Business School, Jenny networked relentlessly, eventually landing a role at ENIAC Ventures, a leading seed-stage VC firm. She later joined Supernode Ventures, where she helped raise their first institutional fund. During the pandemic, she took a leap of faith and launched Four Acres Capital as a solo GP, giving her full control over investments and fund strategy. Tune in to hear the full episode.

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What if we could map the Earth—and even the moon—with pinpoint accuracy from space? In the latest episode of Skin in the Game VC, Saxon Baum sits down with Clint Graumann, CEO of NUVIEW, to talk about how his company is making it possible.

Clint’s journey into space tech started with a winding road through optical satellites and Earth observation, ultimately leading to NUVIEW and a game-changing focus on space-based LiDAR. LiDAR technology uses lasers to measure distances with astonishing precision, but until now, it’s mostly been limited to airplanes and drones, covering small areas. NUVIEW is taking it global—literally—by putting this technology into satellites to collect data on a planetary scale.

Clint doesn’t just see LiDAR as a tool for Earth. With NUVIEW’s recent selection for a European Space Agency mission to map the moon, the company is helping humanity take its next big step toward understanding and utilizing space.

This episode isn't just about LiDAR. Clint offers his insights on the state of the space industry, comparing it to “the first inning, bases loaded, no outs.” He highlights Florida’s growing role as a hub for aerospace innovation and discusses how companies like SpaceX have completely reshaped the game.

From revolutionizing Earth data collection to mapping the moon, NUVIEW’s story is a testament to how the space frontier is becoming more accessible and practical than ever before. Tune in to this fascinating conversation and catch a glimpse of the future

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In the latest episode of Skin in the Game VC, Tom Wallace and Saxon Baum welcomed Brent Saunders, Chairman and CEO of Bausch & Lomb, to share his journey and insights into leadership, healthcare innovation, and the power of investing in groundbreaking ideas. From his early days as student body president at the University of Pittsburgh to overseeing multi-billion-dollar deals in the healthcare industry, Brent’s career is a masterclass in strategic thinking and execution.

Brent reflected on his experience leading companies like Allergan and Bausch & Lomb, where he navigated complex mergers and acquisitions totaling nearly $300 billion. His approach centers on aligning deals with a strong strategic rationale and financial discipline, ensuring long-term value creation rather than short-term gains.

A recurring theme throughout the conversation was Brent’s passion for leveraging technology to tackle inefficiencies in healthcare. He highlighted the potential of AI to transform drug discovery and streamline clinical trials, sharing how his company uses AI to identify solutions for challenging diseases. Brent also emphasized the need for universal, portable medical records to improve patient outcomes and reduce systemic inefficiencies—a vision that remains elusive but vital for the future.

As an active investor, Brent shared his enthusiasm for backing startups that prioritize innovation and have strong, experienced teams. He cited Roam, a Miami-based tech startup led by Howard Lerman, as an example of a company combining cutting-edge ideas with proven leadership. Brent underscored the value of working with founders who have “climbed the hill before,” noting that their experience and resilience often set them apart.

Looking to the future, Brent offered predictions on market trends, including the growing influence of AI and the expected resurgence in mergers and acquisitions as regulatory conditions evolve. His optimism about technological advancements was balanced by a thoughtful caution regarding overuse in areas like pharmaceuticals, emphasizing the importance of weighing benefits against risks.

The episode was not just a window into Brent’s accomplishments but also a reminder of the power of innovation, the importance of adaptability, and the need to continually refine one’s craft. For anyone navigating the intersection of technology, business, and leadership, Brent’s insights provide both inspiration and actionable guidance.

Be sure to tune in to Skin in the Game VC for more conversations with trailblazing leaders and investors shaping the future.

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