The Peel with Turner Novak

Chris Frantz, Co-founder and CEO of Loops—an email platform designed for software companies—shares his insights on the persistent challenges of email communication. He discusses the unique product-led growth strategy and the decision to skip a Series A funding round. Chris dives into the hilarious marketing stunts that built their early user base, including a memorable Times Square billboard. He also explains why all customer support is handled by engineers, reflecting his hands-on approach to user experience.

Dan Gray, Head of Insights at Equidam, dives into the world of startups and venture capital, armed with insights from academic research. He discusses the pitfalls of premature scaling, emphasizing that 70% of failures stem from raising too much cash too soon. The importance of origination stage investing is highlighted, revealing how first-check investors significantly affect startup viability. Gray also critiques the phenomenon of ‘startup catering’, where founders conform too much to investor expectations, leading to a sea of sameness in new ventures.

Dan Feder, Senior Managing Director of Investments at the University of Michigan’s $18 billion endowment, shares insights on venture capital and asset allocation. He emphasizes the need for institutional investors to rethink their strategies and distinguishes between risk and uncertainty. Dan recalls his unique experience racing Lance Armstrong, drawing parallels to investment preparation. He explains the evolution of venture since 2000, the trend of roll-ups in services, and offers key advice for fund managers to attract LPs, highlighting the importance of relevance and independent thinking.

Eoghan McCabe, Co-founder and CEO of Intercom, shares insights on transforming companies into AI-native entities. He discusses the imperative for businesses to develop their own AI models to stay competitive. Eoghan also addresses the challenges of late-stage software companies, the shift to outcome-based pricing in AI, and lessons learned from his return to Intercom. The conversation dives into the complexities of fundraising and the evolving dynamics of venture capital, providing a candid look at the AI landscape and the necessity of innovation.

Albert Azout, Co-founder and Managing Partner of Level Ventures, dives into the challenges of venture investing. He shares insights on how to generate alpha, emphasizing the significance of networking and criticality investing. The discussion also highlights the role of capital flows and the importance of early consensus in maximizing returns. Azout showcases custom software built for analyzing networking dynamics, shedding light on how technology influences investment decisions. This engaging conversation is a treasure trove for aspiring venture capitalists!

Will O’Brien, Co-founder and CEO of Ulysses, is passionate about ocean exploration and the economic potential of the sea, valued at $2.5 trillion. He discusses how Ulysses is developing modular, autonomous robots to help restore marine ecosystems. The conversation also dives into innovative ocean business models, including floating cities and treasure hunts, while highlighting the connection between conspiracy theories and entrepreneurship. O’Brien shares insights on navigating government contracts and the unique challenges of promoting ocean technology.

Isaac Medeiros, Founder of Mini Katana and Kanpai Foods, shares his expertise in building content-driven brands that rack up over 1 billion views monthly. He discusses the stark differences between TikTok and YouTube algorithms and emphasizes the importance of emotional engagement over mere follower counts. Isaac also reveals challenges he faced, like moving his supply chain to Mexico due to tariffs, and offers insights on launching freeze-dried candy products in retail. His strategies for viral content creation and audience loyalty are practical jewels for aspiring entrepreneurs.

Michael Dempsey, Managing Partner at Compound, shares his insights on the evolving landscape of technology and investment. He discusses the intersection of AI and robotics, the importance of value capture for deep tech startups, and the challenges in navigating venture capital. Dempsey reflects on the investment journey with Runway and contrasts traditional investment strategies with those needed for AI startups. He emphasizes the need for adaptability in venture firms and critiques the authenticity crisis emerging in venture content.

Ryan Hoover, the visionary founder of Product Hunt and Weekend Fund, shares his invaluable insights from helping countless entrepreneurs navigate product launches. He reveals how Product Hunt evolved from a simple email list into a tech powerhouse through a unique growth flywheel. The conversation dives into the changing nature of online communities and the impact of AI on human behavior in tech. Hoover also discusses his venture investing journey, highlighting a remarkable 400x investment in consumer health and the significance of authenticity in Silicon Valley startups.

Sahill Poddar, Co-founder and CEO of Parafin, transitioned from a career in particle physics at CERN to revolutionizing SMB lending with AI. He shares insights on overcoming the challenges of traditional banking for small businesses, particularly in the gig economy. Poddar discusses how data-driven solutions helped secure big names like DoorDash as clients. He also draws parallels between machine learning in physics and Fintech, emphasizing the importance of innovation and customer understanding in modern lending.