The IO Podcast: Investor + Operator

Larsen Jensen is an Olympian swimmer-turned-Navy SEAL and the founder of Harpoon Ventures, focused on tech for defense. He shares his journey from the Olympics to elite military training, emphasizing the mindset needed to succeed in both. The discussion pivots to the critical moment of knowing when to quit or persevere in a startup, highlighting market timing and product fit. Larsen also details his venture into military tech investing, discussing the evolution of Harpoon Ventures and the increasing interest in defense technology.

Joshua Silver, the founder and CEO of Rainforest, shares his incredible journey of reaching over $1 billion in payment transactions within just one year. He discusses the unique market opportunities he identified and how his previous founding experience equipped him for success. Joshua highlights the importance of deep customer insights, strategic targeting of niche software platforms, and the critical metric of processing volume. He also explains how effective fundraising strategies and strong team dynamics have been key to his company's rapid growth.

Daniel Simon, Founder and CEO of Coast, shares invaluable insights from his journey in fintech, notably after co-founding Bread, which sold for $500M. He discusses the key to competing with large incumbents by emphasizing product differentiation and maintaining a mobile-first approach. Daniel also delves into effective fundraising strategies, cultivating relationships with investors, and innovative customer acquisition methods. His passion for revolutionizing financial services shines through as he outlines exciting plans for Coast's future.

Rene Saul, CEO and co-founder of Kapital, a groundbreaking $1.3 billion startup from Mexico City, shares his extensive entrepreneurial insights. He discusses how past ventures shaped Kapital’s success and the need for resilience in overcoming failures. Rene highlights Mexico's transformative tech landscape and the innovative banking solutions Kapital offers to small and medium-sized businesses. He also draws parallels between running marathons and building self-belief in entrepreneurship, showcasing the importance of determination and adaptability in navigating startup challenges.

In this engaging conversation, Adam Edmunds, CEO of Entrata, shares insights from his journey in building a property management software company poised to be Utah's next big success. He discusses the art of fundraising, highlighting the significance of cultivating investor relationships, especially with Blackstone. Adam dives into the challenges of navigating rapid company growth, emphasizing the importance of recruiting top talent while preserving company culture. He also reflects on his personal motivations, seeking fulfillment through meaningful connections and leadership experiences.

Arjun Sethi, managing partner at Tribe Capital and co-CEO of Kraken, dives into the world of venture capital and cryptocurrency. He shares his unique approach to achieving product-market fit and the frameworks that guide his investment strategies. Arjun emphasizes the importance of data analysis and user behavior in driving product success. He also discusses the dynamic nature of remote work and its implications for innovation. With insights into navigating market cycles and fostering relationships in VC, he presents a compelling vision for the future of investment.

Brett Berson, a Partner at First Round Capital, shares his journey from intern to key player in seed-stage investments. He discusses what founders should ask when raising a Series A, emphasizing the importance of building strong narratives and investor relationships. The impact of AI on startups is also explored, highlighting both opportunities and challenges. Berson delves into common missteps for seed-stage startups and the significance of balancing technical expertise with commercial know-how to attract the right venture capital.

Garrett Langley, founder and CEO of Flock Safety, leads a company revolutionizing crime prevention through innovative technology. He shares how a team-focused approach helped land lucrative contracts with police stations, transforming a whiteboard idea into a $7 billion success. Key topics include the importance of personal engagement in sales, navigating the challenges of hardware development, and the vital role of understanding customer needs. Garrett's insights on building community safety solutions will inspire aspiring entrepreneurs and tech enthusiasts alike.

In a captivating discussion, Eric Vishria, General Partner at Benchmark Capital, shares his unique insights into funding AI startups. He reveals how diverse revenue strategies and a strong team dynamic are key to identifying investment opportunities. Eric emphasizes the balance between human expertise and AI automation, highlighting the importance of adaptable founders with unique market insights. The conversation also explores the evolving landscape of venture capital and the growing significance of personal chemistry in startup partnerships.

John Andrew Entwistle, Founder and CEO of Wander, shares insights on pioneering the vacation rental industry. He reveals inventive waitlist strategies that attract customers before a product launch. The conversation covers solving supply challenges, transitioning to third-party inventory, and choosing revenue models. Entwistle emphasizes building a visionary workplace culture at Wander, where exceptional service fosters customer loyalty. He also delves into blending technology with personal touch to enhance guest experiences, positioning Wander as an industry disruptor.