A Product Market Fit Show | Startup Podcast for Founders

Rob Woollen, Co-founder of Sigma Computing, shares his journey from years of struggle to achieving $100M ARR. He reveals the tough lessons learned during seven years without revenue and the crucial pivots that transformed failure into success. Rob emphasizes the importance of patience over speed in reaching product-market fit and discusses the psychological toll of startup uncertainty. He also highlights the unexpected power of building features that customers didn't request, showcasing how innovation thrives on resilience and user-centric design.

Benedetta Lucini, founder of Oval Money and former Uber manager in Europe, shares her candid startup journey. Despite raising $10M and gaining 500K users, she reveals how chasing big partnerships can derail success. Benedetta discusses the pitfalls of corporate VC reliance, the complexities of adapting US models to Europe, and costly fundraising mistakes. She encourages founders to validate ideas before building tech and highlights the emotional toll of making tough decisions when facing failure. This is a must-listen for aspiring entrepreneurs.

Hernan Kazah, co-founder of Mercado Libre and Managing Partner at Kaszek Ventures, shares insights from building Latin America's leading e-commerce platform. He discusses how Mercado Libre survived financial turmoil by prioritizing profitability over rapid growth. Hernan explains the significance of focusing on fewer key areas to build a strong foundation, the innovative strategies for attracting initial users, and the lessons learned from navigating competitive pressures. His journey illustrates the power of resilience and strategic patience in the startup world.

Four founders share their unconventional paths to building massive startups outside of traditional tech hubs. Discover how a travel app skyrocketed to $10M ARR by focusing on a single metric. Learn about the ten-year journey to compounding growth for a service platform, and the strategic choices behind Public.com's success. Emphasizing the importance of mastering your craft and knowing when to break the rules, these insights challenge conventional wisdom, proving that determination and focus on product quality lead to remarkable achievements.

Jordan Dearsley, founder of Vapi and former calendar app developer, shares his transformative journey from stuck at $500K to hitting $10M ARR in just one year. He discusses the bold decision to abandon a profitable venture, revealing how identifying a '10/10 burning pain' led to explosive growth. Jordan emphasizes customer anger as a growth signal and explains why true conviction is essential in a founder's journey. Listeners gain insights on navigating rapid growth, competition, and the critical nature of product-market fit.

Arvind Jain, founder of Glean, built an AI-powered enterprise search tool after leaving a unicorn, raising $15M without early revenue. Kyle Hanslovan, founder of Huntress, transformed from an NSA hacker to leading a cybersecurity firm, overcoming relentless rejections and financial struggles. They discuss how chasing perfection can hinder progress and share insights on fundraising. The conversation highlights the importance of rapid market entry and adapting to feedback to achieve product-market fit, offering invaluable lessons for aspiring founders.

Avery Pennarun, founder of Tailscale, turned a small project into a $2B success, raising $160M without chasing investors. He shares how Tailscale achieved over $10M in ARR purely through word-of-mouth, emphasizing the power of solving small, everyday developer issues. Avery discusses the counterintuitive advantages of failure with early users and how the pandemic unexpectedly fueled their growth. Expect practical insights on navigating startup decisions and the pivotal role of understanding customer needs for product-market fit.

Jack Kuveke, a seasoned voice on startup news, dives deep into the rollercoaster world of tech this month. He unpacks the dramatic rise and fall of figures like Elizabeth Holmes, revealing unsettling trends in the startup scene. The conversation shifts to OpenAI’s secretive project with Jony Ive and the escalating number of billion-dollar frauds. Jack also paints a bleak picture of the vanishing entry-level tech jobs and the bizarre antics in the crypto world, questioning the integrity of modern investments while sprinkling in some levity.

Merrill Lutsky, the founder of Graphite—a cutting-edge code review platform—shares his incredible journey from near failure to hitting $1M ARR in just 10 months. He discusses the key lessons learned from product pivots and landing a massive enterprise client. Merrill reveals how daily user feedback became a game-changer for growth and the surprising pricing tweaks that doubled revenue overnight. He also emphasizes the importance of trust within a founding team, particularly amidst the chaos of startup life.

Early-stage founders often face overwhelming chaos. They discuss why true passion is essential for longevity in the startup game. It’s revealed that while fundraising might be deceptive, genuine product-market fit cannot be faked. The importance of prioritizing tasks ruthlessly is highlighted, as focus means knowing when to say no. Slow initial growth can be advantageous, and positioning yourself for luck is just as crucial as having a robust plan. Ultimately, it's about aligning with the market to ensure lasting success.