Nnamdi Okike's Playbook for Investing in Non-Obvious Winners

Episode SummaryNnamdi Okike is the Co-founder and Managing Partner at 645 Ventures, known for his early, contrarian bets on overlooked verticals and non-obvious industries. In this episode, Nnamdi shares how he leveraged a data-driven sourcing model to identify breakout companies like Squire and Goldbelly, and why seemingly small or niche markets often produce the biggest wins. Maxine and Cheryl dive deep into Nnamdi’s journey from Insight Partners analyst sourcing deals via cold calls, to launching his own fund and achieving a remarkable hit rate, landing him on the Midas Brink List. They explore how he evaluates founder insights, measures market inflection points, and strategically navigates the power law dynamics in venture capital. Packed with strategic insights and candid reflections, this episode is essential listening for emerging investors, fund managers, and founders curious about building defensible businesses in non-obvious spaces.Time Stamps04:34 – Nnamdi’s first investment during the dotcom boom06:52 – Defining “non-obvious industries” and spotting hidden TAM10:40 – Squire: From barbershop bookings to vertical SaaS OS13:20 – Goldbelly, marketplaces, and the power of founder insight17:58 – Algorithmic sourcing meets founder conviction21:30 – What 645 Ventures learned from missing Facebook26:46 – Building a fund around risk profiles, not just stages30:34 – Why the power law should shape every VC decision35:16 – Does 2024 echo 2002? A macro take on the downturn42:41 – The rise of zombie funds and quiet closures45:20 – Bootstrapped AI startups and the future of defensibility52:54 – When vertical AI gets sticky—and when it doesn’t57:20 – Nnamdi’s Big Cojones moment: from Insight to starting freshResources🙋‍♂️ Nnamdi Okike on LinkedIn – Follow Nnamdi’s updates and insights. https://www.linkedin.com/in/nnamdiokike💰645 Ventures – A VC firm investing in early-stage, non-obvious software winners. https://645ventures.com/First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpSpotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/

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