A Product Market Fit Show | Startup Podcast for Founders

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8 snips
Feb 26, 2026 • 38min

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

Didi Gurfinkel, founder and CEO of Datarails who pivoted from five years of failed products to scale a finance-focused company. He talks about discovering FP&A for Excel users, proving demand with low-price contracts, closing four customers in a pivotal week, and building a 100% outbound sales engine that drove rapid growth to tens of millions in ARR.
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15 snips
Feb 23, 2026 • 55min

His startup powers OpenAI's Voice Mode. Last month, they became a unicorn. | Russ d’Sa, Co-Founder of LiveKit

Russ d’Sa, Founder and CEO of LiveKit, built the infrastructure behind real-time audio/video and powered ChatGPT’s voice mode. He tells how a pivot from a consumer app to open source infrastructure changed everything. Stories include a scary sell-or-die threat, a secret OpenAI outreach, and how LiveKit scaled stateful voice agents to become a unicorn.
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Feb 19, 2026 • 36min

He pivoted at $1M ARR—then raised $120M. | Kevin Tian, Co-Founder of Doppel

Kevin Tian, co-founder of Doppel and former NFT founder turned cybersecurity CEO, explains a daring pivot from NFT products to AI-driven defenses against impersonation. He recounts selling a $5k/month pilot with no product. He discusses shifting to enterprise cyber, network-led sales, and raising a Series A from a16z during the transition.
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10 snips
Feb 16, 2026 • 56min

He sold his first startup for $100M. Then raised $250M in 18 months. | Dileep Thazhmon, Founder of Jeeves

Dileep Thazhmon, founder and CEO of Jeeves and prior founder who sold a startup for $100M, shares bold growth moves. He recounts mailing cards by hand to prove demand. He explains raising from many small investors, pivoting to Jeeves Pay, and the “Beat Down” idea-validation framework. He also describes reaching rapid ARR and surviving rate shocks with tough product choices.
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17 snips
Feb 12, 2026 • 50min

He sold his first 2 startups. His 3rd grew to $1M ARR in 3 months. | Chaz Englander, Founder of Model ML

Chaz Englander, serial entrepreneur who sold two startups and now runs Model ML, shares his rapid-scaling playbook. He talks about pitching strangers on LinkedIn for checks. He explains minimal MVPs, AI-driven speed, design-partner tactics, and how he went from $5k to $100k MRR in months.
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7 snips
Feb 9, 2026 • 52min

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

Jay Madheswaran, founder and CEO who pivoted from VC and engineering roles to build Eve, a legal-AI unicorn. He describes firing all customers to focus on plaintiff-side legal workflows. Rapid demo wins, 40% cold-to-demo conversion, and 4-hour user sessions that signaled true demand. The conversation covers pivot pressures, go-to-market tactics, and the product discovery that sparked hypergrowth.
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15 snips
Feb 5, 2026 • 39min

He wrote the book on Account Based Marketing. Here are his GTM secrets for enterprise. | Bassem Hamdy, Founder of Briq

Bassem Hamdy, founder and CEO of Briq and former product and marketing exec, shares his GTM playbook for enterprise. He explains pivoting to RPA bots, why selling risk reduction wins, and his ABM tactics like the 1-person webinar. He also reveals why trade shows fail, how to spot the internal challenger that will kill a deal, and why AI orchestration matters more than you think.
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25 snips
Feb 2, 2026 • 52min

He got rejected from YC—then grew to $1.8B in under 2 years. | Max Junestrand, Founder of Legora

Max Junestrand, founder of Legora and builder of a $1.8B AI legal-tech unicorn, tells the rapid scale story. He explains pausing sales to rebuild product infrastructure. He shares the conference live demo that sparked 150 leads and the demo tactics that convert 55% of prospects. He also covers how they beat incumbents with fast shipping and enterprise bake-offs.
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Jan 29, 2026 • 52min

He sold dog food from his condo. Now he does $100M+ a year. | Russell Breuer, Founder of Spot & Tango

Russell Breuer, founder of Spot & Tango who scaled a studio‑apartment dog‑food side hustle into a nine‑figure DTC brand. He recounts hand‑delivering first orders, inventing UnKibble fresh‑dry food, and vertically integrating manufacturing. Short stories cover branding with pink butcher paper, cheap winning ad creative, and the four‑day sellout that signaled product‑market fit.
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Jan 26, 2026 • 52min

He made 100 cold calls a day. Now his startup is worth $600M. | Harman Narula, Founder of Canary Technologies

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.

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