A Product Market Fit Show | Startup Podcast for Founders

Harman Narula, founder of Canary Technologies and hospitality-tech builder, turned a paper credit-card form into a $600M guest management platform. He recounts making 100 cold calls a day, the activated "hair on fire" wedge that unlocked thousands of hotels, the outbound-first sales machine, and the moment signing 200+ hotels proved product-market fit.

Rich White, Founder and CEO of Fathom, shares his journey from securing a spot on the Zoom Marketplace to generating 100k signups in just 30 days—only to find that nearly all of them were non-usable. He details the critical pivot to monetization during a market downturn, the importance of a long private beta, and how the 'Visible Feature' mechanic spurred organic growth. Rich also discusses selling a non-existent roadmap to reach $100k ARR swiftly and the pivotal role of AI tools in transforming user experience and retention.

Bob Tinker, a serial entrepreneur and founder of MobileIron, scaled the company to $150M in revenue and led it to an IPO. Now, he’s back with BlueRock, focusing on agentic AI security. He emphasizes the importance of distinguishing between Product-Market Fit and Go-To-Market Fit, revealing how the former can lead to increased burn rates. Bob shares insights on conducting customer interviews, overcoming founder-led sales challenges, and using 'Deal Grind' sessions to refine sales strategies. He believes agentic AI is the next big wave, similar to the mobile revolution.

Shahar Peled, the Founder and CEO of Terra Security, dives into his rapid ascent in the cybersecurity landscape. With a background in management and data science, he shares how his AI-first service disrupted the manual pen-testing market. Learn about the 'Service-as-Software' model that propelled him to $1M ARR in just three months, and why traditional customer validation methods fall short. Shahar also reveals his tactics for converting design partners into paying clients and achieving impressive sales metrics. This is a masterclass in scaling and product-market fit!

Ashwin Sreenivas, Co-founder of Decagon, built a $1.5B AI startup in just two years with a lean team. He emphasizes the importance of engaging with over 100 potential buyers to identify significant pain points and validate high-value contracts early on. Ashwin shares his strategy of delaying hiring until hitting $1M ARR and how avoiding over-complicated strategies fueled his rapid growth. He also discusses the importance of delivering tailored solutions and using real customer feedback to pivot successfully in the competitive AI landscape.

Jake Stauch, Founder and CEO of Serval, shares his remarkable journey from a failed startup to a $1B valuation in just 18 months. He discusses the bold decision to rebuild a full platform to replace ServiceNow, achieving an astonishing 50% close rate on sales demos. Jake reveals insights from over 100 customer discovery calls that pinpointed the real pain points in IT workflows. He highlights the importance of asking specific questions to unlock genuine customer feedback and how calculated risks in AI development played a crucial role in Serval's rapid growth.

Siqi Chen, Founder and CEO of Runway, shares his journey from leading Sandbox VR through a devastating COVID crash to creating innovative finance tools. He discusses the importance of product taste over A/B testing and reveals the surprising tactics behind a viral launch that brought in $1M ARR in just 30 days. Siqi also highlights the resilience required in startups, the challenge of customer willingness to pay, and how creating a product can take years of dedication before achieving success.

The startup landscape has shifted dramatically due to GenAI. Incremental value propositions are becoming obsolete, as founders shift to creating undeniable value. Three new competitive threats are emerging: incumbents, foundation models, and rapid entrants. The focus has moved from time-to-market to cycle speed as the only available moat. Furthermore, pricing strategies are evolving, moving beyond traditional per-seat models. A rising opportunity is the Service-as-Software model, where AI-driven services capture demand swiftly.

Kyle Hanslovan, Founder and CEO of Huntress, shares his remarkable journey from NSA hacker to leading a $2B cybersecurity firm. He reveals the harsh realities of bootstrapping, including sleeping in his car and facing 60 VC rejections before finally hitting $100M ARR. Kyle discusses the critical importance of understanding the SMB market, leveraging partners, and achieving impressive net revenue retention. He also speaks candidly about personal sacrifices and the grit required to transform setbacks into success.

Viraj Parekh, Co-founder of Astronomer and a pivotal figure in commercializing Apache Airflow, shares his startup journey from creating a clickstream product to pivoting into a managed Airflow service. He reveals the crucial lessons learned, like how constant customer conversations and asking the right questions validated their pivot. Viraj discusses the importance of resilience, especially during their slow climb to $1M ARR, and how being outside Silicon Valley led to unique challenges and innovative solutions in fundraising and customer engagement.