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Ken Goldman spent five years as President of Hillspire, Eric Schmidt's family office, an organization of over five hundred people spanning investments, legal, IT, aviation, personal property, foundations, and an oceanographic research vessel. He was CFO of Siebel Systems and CFO of Yahoo, was employee number seven at VLSI Technology, and has served on dozens of public and private boards. He now invests actively across venture and private equity funds and sits on the PCAOB advisory group.
⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com
Topics covered:
- Why the analysis that said sell Alphabet was the best call Hillspire never made
- How you hire and retain people when you have no equity to offer, and who you stop competing for
- The split between the institutional book and the "VIP investments" Eric Schmidt made himself
- What separates a family office conference worth attending from one where you are the product
- Why Ken says we are in a bubble even though every insider he asks says AI is under-hyped
Connect with Ken Goldman:
LinkedIn: https://www.linkedin.com/in/ken-goldman-552a47
Connect with Prashant Choubey:
LinkedIn: https://www.linkedin.com/in/ken-goldman-552a472
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Timestamps:
(00:00) - Preview
(01:19) - Guest intro
(03:07) - The operational scale of a 500+ person family office
(07:12) - Tips for retaining high-quality talent in the age of AI startups
(08:45) - The importance of being in the office to build team culture
(12:04) - The trend of institutionalization in family offices
(12:45) - A breakdown of Hillspire's diverse in-house operations
(15:15) - Why private equity and VC firms are now targeting family offices
(17:47) - Identifying the highest quality family office conferences
(18:17) - What makes a family office conference valuable (non-solicitation, quality speakers)
(23:31) - Common blind spots of emerging family offices
(26:41) - Approach to venture capital: direct investing vs. backing funds
(30:56) - Framework for executing philanthropy in a family office
(34:51) - Building a personal portfolio of alternative investments
(39:35) - Essential financial controls for startups before hiring a CFO
(43:45) - Is the current AI cycle overhyped or underhyped?
(48:00) - Governance warning signs that a startup is drifting off course
(49:05) - Key metrics to watch: customer churn and net ARR
(52:18) - Dangerous assumptions investors carry from bull to bear markets
(55:20) - Why we are likely in an investment bubble, especially in data centers
