In this episode, Cyrus Hessabi from Shore Capital Partners breaks down what it really looks like to build AI-enabled services, transition from VC to micro-cap private equity, and back searchers buying “boring” but powerful businesses.
Cyrus has lived every chapter of the operator-investor journey: aerospace engineering, Salesforce sales, venture capital, architecting AI rollups at OpenOcean, and now backing searchers at Shore Capital Partners.
We dive into how AI is transforming traditional service industries, where real opportunities (and risks) lie, how to evaluate founders, and why the best investing often happens in industries that don’t change.
TIMESTAMPS:
0:00 Cyrus’s operator & investor journey
2:02 Spotting the tech gap in the traditional economy
3:43 Data infrastructure, MySQL roots & AI rollups at OpenOcean
5:15 Bridging VC, AI and micro-cap PE
7:35 Sponsor: Capitalpad - invest alongside vetted searchers
8:37 What AI-enabled services really are (with simple examples)
12:21 Inside OpenOcean’s AI-enabled services thesis & deal work
16:00 Joining Shore Capital & backing searchers and roll-ups
17:08 Sponsor: Spacebar Studios - done-for-you newsletters
18:14 How Cyrus evaluates AI risk and upside in real deals
31:01 Moving from VC to ETA/PE and key mindset shifts
45:46 Investing in what doesn’t change, AI as a tailwind & favorite book
Sponsors:
https://capitalpad.com/
https://www.spacebarstudios.co/inquire
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This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
