Lessons from a Startup Life
Lessons from a Startup Life Podcast
Rob May: AI startup CEO, AI investor & AI industry analyst
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Rob May: AI startup CEO, AI investor & AI industry analyst

Key learnings from AI investments, the ChatGPT stampede, AI PMs, art and more.

Voices in this podcast are from DougL and his guest. Edits provided by (human) friends. AI was not used to create, write or edit this podcast or the accompanying notes. Browser-based technology with generative AI and ChatGPT was used to fact check.

Rob May is the CEO and Founder of Nova Cloud. That makes him a four-time entrepreneur. He’s also made angel and VC investments in over 100 startups. He’s worked in the past as an electrical engineer designing various hardware devices. As an industry analyst, Rob writes the newsletter “Investing In AI” and hosts the “AI Innovator's Podcast”. 

Rob May is the co-founder of the AI Operators Fund along with Rana el Kaliouby. Rob tries to be the first check in. He likes to take "syndicate risk" — there is a risk waiting for the deal to close and a VC invests and takes out good deals. Valuations have come down and they are getting into really good deals.

His reading of this moment: ChatGPT will unlock new businesses and vertically targeted startups. LLMs get better as they get bigger. Scaling is different and it has emergent properties. SaaS early stage investments take $4-5m; AI deals need $6-8m. There are other differences. But this space will have heavy over-investment.

AI companies: There's a lot of defendability. Data is the moat. Beyond product market fit, today there's "model market fit". We discussed "The ChatGPT Stampede" and many other interesting topics.

Recommended reading: Investing in AI (Rob's blog)


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Lessons from a Startup Life
Lessons from a Startup Life Podcast
Doug Levin is the creator, writer and moderator of “Lessons from a Startup Life” – the podcast. Today he is a lecturer at Harvard Business School, board member, startup adviser, technology investor, and former CEO who has made it his life mission to share practical advice with anyone working in the tech or startup world. Relevant for executives, investors and employees alike, this expansion on his “Lessons” blog on SubStack, draws on decades of experience and provides a unique analysis of the market — from business plan creation, to forming a founders team and subsequently ELT, financing, culture and more. The end result is a playbook and insider’s approach to the startup game, with first-hand experience from guest experts who've gone through it themselves.