Skin in the Game VC Podcast

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.

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 AIHow KnowBe4 is evolving into a platform companyWhy AI and quantum computing will trigger “company extinction events”His belief that LLMs are already a commodity, and the future lies in vertical AI agentsFor 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.

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.

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

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.

The latest episode of Skin in the Game VC Podcast featured an inspiring conversation with Tom Wallace, Saxon Baum, and the dynamic sister duo, Amy and Shannon Wu. As founders backed by Florida Funders, Amy and Shannon shared their unique entrepreneurial journeys, highlighting the resilience and innovation shaping their paths in the tech world. Their story is a testament to the power of collaboration, as they support and inspire one another while carving out success in competitive markets.Amy Wu, founder of Manifest, and Shannon Wu, founder of Open Home, have both built groundbreaking companies leveraging the transformative potential of AI. Manifest addresses Gen Z’s mental health challenges through personalized, AI-driven tools, creating bite-sized wellness interactions to combat loneliness and anxiety. Meanwhile, Open Home is revolutionizing smart speakers, enabling more intuitive and seamless voice interactions across a wide range of devices. Both sisters emphasized how AI allows lean teams to achieve significant impact, unlocking personalized solutions that enhance human connection and creativity.Their journey reflects a shared commitment to innovation and a deep bond that has guided them through challenges and triumphs. They credit their early experiences at Stanford and the personalized support from Florida Funders as key drivers of their success. Florida Funders’ hands-on approach contrasts with the broader yet less personal resources of larger VC firms, offering a uniquely curated experience that has helped Amy and Shannon thrive.As these visionary founders continue to push boundaries, their work underscores the exciting potential of AI and the importance of fostering meaningful human connections in an increasingly digital world. Startups like Manifest and Open Home showcase how technology can be a tool for empowerment, solving real-world challenges with creativity and purpose. Tune in to this latest episode of Skin in the Game.

In our latest episode of the Skin in the Game VC Podcast, we explored the multifaceted journey of Ann Berry, Founder and Managing Partner of Threadneedle. From Wall Street to private equity, venture capital, and operating, Ann’s career path is a testament to adaptability and innovation.Ann’s professional journey began at Goldman Sachs, where she specialized in leveraged buyouts. Her transition to private equity allowed her to lead as a CEO, navigating a hospitality portfolio company through the COVID-19 crisis. This experience solidified her love for operational leadership and reshaped her investment philosophy. Ann now focuses on leveraging technology to modernize traditional industries.Notable investments include Yuv, a company revolutionizing the hair salon industry with personalized hair color technology; Airship, providing software solutions for HVAC and plumbing contractors; and Reality Defender, tackling deepfake risks in cybersecurity. Ann’s approach emphasizes bridging innovative startups with legacy industries that stand to gain from technological advancements.Beyond investing, Ann has embraced content creation, partnering with Morning Brew to develop Brew Markets. Through her media work, she highlights the interconnectedness of public and private markets, emphasizing the value of storytelling in leadership and entrepreneurship. “Storytelling is endemic in everything we touch,” Ann shared, reinforcing its importance for founders and investors alike.Looking ahead, Ann predicts a resurgence in the IPO market by 2025 and highlights the untapped potential of AI applications, particularly in industries reliant on proprietary data. However, she cautions that overhyped AI startups must prove their scalability and real-world value.This episode offers invaluable insights for founders and investors, from navigating leadership challenges to understanding the role of storytelling in building and scaling businesses. Tune in to hear Ann’s visionary take on the future of venture capital and entrepreneurship.

Joe Hogue started his career as a traditional equity analyst and venture capitalist but left the corporate world in 2013 to gain more autonomy. By 2017, he had transitioned into content creation, launching his YouTube channel, Let’s Talk Money, which now has over 650,000 followers.Joe’s mission is to make investing accessible, blending entertainment with education to empower retail investors. Beyond content creation, he’s innovated by tokenizing his YouTube ad revenue, raising over $250,000 and engaging 700 investors—pioneering blockchain use in the creator economy.In this episode of Skin in the Game VC, Joe shares insights on his journey, the future of markets, and the role of creators in finance. His story is a testament to leveraging innovation to educate, inspire, and redefine industries.

Dave Sachse is the founder of Family VC and a leader in the world of family office investing, where he helps family offices navigate venture capital by building networks, sharing resources, and creating opportunities for collaboration. With a background in managing his own family's single-family office in Wisconsin, Dave has a deep understanding of the unique challenges family offices face when investing in early-stage tech companies. He founded Family VC to connect like-minded family offices, fostering a community of over 200 members who share deal flow, best practices, and strategic insights in venture capital.Dave is passionate about tech innovation and values-aligned investing, favoring pre-seed to Series A stages where family offices can add real value beyond funding. His approach is hands-on and collaborative, leveraging partnerships with experienced VCs and investing in diverse tech sectors across the U.S. Family VC aims to make family offices a lasting force in the venture world, helping these investors move beyond traditional asset classes to become impactful players in early-stage tech.Tune into this episode of Skin in the Game VC to hear more of Dave’s insights on the shifting landscape of venture capital and the role family offices are playing in supporting the next generation of innovation.