A Product Market Fit Show | Startup Podcast for Founders

Dheeraj Pandey, founder of Nutanix, transformed it into a $20B company before launching DevRev and raising a $100M Series A. He discusses the pitfalls of the 'sell and run' mentality, emphasizing the importance of delivering value post-sale. Dheeraj shares insights on platform thinking vs. feature-based approaches, how to navigate product-market fit at various milestones, and his vision for AI-native products. He recounts near-death experiences at Nutanix and advocates for focusing on customer retention to achieve sustainable growth.

Simon Eskildsen, the founder of TurboPuffer and a former Shopify infrastructure engineer, discusses his journey of creating a cost-effective vector database. He reveals how he helped Cursor cut their costs by 95% within a week by migrating their entire workload. Simon emphasizes the importance of being willing to fly to customers and shares the exhausting 24-hour coding sprints that won over Notion. He also outlines his six reasons for considering fundraising and why he prefers staying profitable with a small team instead of raising unnecessary capital.

Guy Podjarny, founder and former CEO of Snyk and current founder of Tessl, shares his journey of turning a $4M investment into a successful security company. He reveals that while thousands of developers loved Snyk, the crucial gap was in aligning with security teams, the actual buyers. By developing governance and enterprise features, he transformed Snyk’s monetization strategy, leading to skyrocketing growth. Guy also discusses his pivots to AI-native developer tools and emphasizes the importance of avoiding stagnation in entrepreneurship.

In this installment, Amar Varma, a five-time founder who has driven projects like Tinder and sold Autonomic to Ford, shares his inspiring journey. He reveals how he negotiated an enormous deal by asking for a contract so large only the CEO could approve it, flipping the power dynamic. Amar also discusses why a higher price can open doors in enterprise sales, his new venture Mantle’s innovative approach to competing with giants like Carta, and crucial lessons for founders in navigating startup challenges.

Ben Alarie, the Founder and CEO of Blue J, is a tax law professor who revolutionized AI in tax research. He reflects on his journey from having 'partial product-market fit' to achieving remarkable growth, scaling from $2M to $25M in ARR after a bold rebuild. The episode dives into the importance of recognizing true PMF versus self-deception, the game-changing role of retrieval-augmented generation, and how improving 'time to value' has driven rapid customer adoption and word-of-mouth referrals.

Dean Sysman, co-founder and CEO of Axonius, shares his journey from a Unit 8200 alum to leading a $100M ARR cybersecurity platform. He reveals how a pivotal moment with a Fortune 500 client transformed their outlook on market potential. Dean emphasizes the critical role of rapid responses to client needs and discusses the three types of enterprise software journeys. With humor, he recounts overcoming initial failures and the branding strategy that propelled Axonius into a newly defined market. A must-listen for aspiring founders!

Casey Ellis, founder of Bugcrowd, created a pioneering cybersecurity marketplace that raised over $180M. He shares how he turned hackers into allies and validated a two-sided marketplace with minimal resources. Casey tested his pitch on Uber drivers to refine his messaging and emphasizes the importance of product-market fit. He reveals how early marketing tactics, like giving away t-shirts, sparked growth and how landing Google early boosted credibility. His journey highlights the emotional rollercoaster of category creation and the value of community support for founders.

Zach Lloyd, a former Google principal engineer who led Google Docs, shares his rollercoaster journey from a failed photo-sharing app to the groundbreaking Warp.dev. He discusses the disillusionment of transitioning from Google’s user base to the stark reality of startup struggles. Zach emphasizes the importance of documented operating principles and building a product-focused team. He reveals how their pivot to AI-driven agentic development led to accelerated growth, achieving $1M ARR every 10 days and successfully navigating the competitive developer tools landscape.

In this engaging discussion, Alex Sherman, Founder and CEO of Bluefish AI and former founder of PromoteIQ, shares his rollercoaster journey through the startup world. He reveals how he nearly returned $200K to investors just months in and how surviving on minimal runway taught him resilience. Alex emphasizes the power of meeting customers face-to-face, successfully pivoting to retail media, and the strategic moves that led to his company's acquisition by Microsoft. His insights on AI marketing and the unique challenges faced by second-time founders are particularly enlightening.

Brett Carlson, Founder and CEO of ServiceUp, shares his wild journey from a failed auto shop to creating a $50 million ARR marketplace for fleet maintenance. He recounts a harrowing story of receiving death threats while managing a drug dealer's car. Discover how pivoting from B2C to B2B skyrocketed their average order value and why work-life balance is a myth for ambitious founders. Brett also discusses raising $12 million during a market downturn and lessons learned from a challenging partnership with DoorDash.