The Hardest Fund I to Underwrite | Zach Ruchman

“The question at Fund IV is, ‘Okay, you’ve proved that you’re a great firm builder. Congratulations, you’re raising Fund IV. Are you still a great investor?’”Zach Ruchman joined HB Wealth in 2025 as a Shareholder after working with WMS Partners since 2023. In his role as Managing Director, Private Markets, Zach leads the team responsible for research and due diligence of private market investment opportunities across a variety of asset classes, including private equity, growth equity, venture capital, private credit, infrastructure, and real assets.Before joining HB Wealth, Zach was a Senior Vice President at RockCreek and a Vice President at BlackRock, where he led direct co-investment transactions as well as manager research for both primary and secondary commitments in the Americas, Europe, and Asia on behalf of both institutional and family office clients. He began his career as a consultant with Alvarez & Marsal. In this episode, we also talk about how he worked out of the National Democratic Institute's DC office writing grants and tracking political regimes in the Middle East, including the Arab Spring.In the community, Zach serves as a member of the finance committee for the Howard and Geraldine Polinger Family Foundation.You can find Zach on his socials here:LinkedIn: https://www.linkedin.com/in/zruchman/X / Twitter: https://x.com/zmrphotoOUTLINE:(00:00) Intro(03:04) When 9/11 entered Zach's life(12:20) Interest in the Middle East(15:00) Returning to the US(17:49) What's in the foreign service exam?(22:29) From pursuing the state department to consulting(25:39) Consulting to allocating(32:20) Business school and mentors(36:34) The ask(37:07) How Zach makes re-up decisions?(40:15) The difference between a Fund I and Fund IV(43:26) Alignment between senior and mid-level investors(45:33) Deal attribution at big VCs(46:40) Questions to ask to references to find deal attribution(49:12) Avoiding a reference's scripted answer(52:14) Top 1% performers leaving organizations(53:45) The hardest Fund I to underwrite(1:00:57) Does radical transparency work?(1:06:15) "Private assets work best when they're inefficient."(1:09:20) Does AI change VC investing?(1:11:33) Sourcing that AI cannot do(1:14:26) Can AI write good memos?(1:19:11) Pattern vs exception recognition(1:25:03) An example of how a GP proved he worked hard(1:28:00) Best advice for action photographyFollow David Zhou for more Superclusters content:For podcast show notes: https://cupofzhou.com/superclustersFor Superclusters After Hours: https://superclusterslp.substack.com/Follow David Zhou's blog: https://cupofzhou.comFollow Superclusters on X: https://x.com/SuperclustersLP