Tax Alpha, Overlays, and Why Privates Matter

How can ultra-high-net-worth families invest like endowments—without becoming forced sellers when markets turn? In this episode, I go deep with Greg Brown, Co-CEO of Caprock, on how a modern multi-family office serves UHNW families. Greg explains why Caprock acts as CFO first and CIO second, forecasting liquidity across complex balance sheets before allocating to private markets. We cover the thresholds for when privates make sense, how to structure portfolios for resilience, the role (and limits) of interval funds, and how Caprock uses pooled scale to negotiate economics and secure access to top deals. We also explore tax-alpha strategies like QSBS, Opportunity Zones, and long/short overlays.

Highlights:

• Why Caprock takes a CFO-first, CIO-second approach to wealth management
• Liquidity forecasting: mapping every entity, flow, and obligation
• Threshold for UHNW privates: around $10M investable assets
• How full balance-sheet visibility lets families hold more illiquids
• Scale advantages: pooled vehicles with no fees, no carry
• Direct access to elite deals: SpaceX, Anduril, Palantir, Addepar, Anthropic, and more
• Interval funds: where they fit, where they don’t, for taxable investors
• Liquidity buckets: 0–6 months, 6–18 months, and 2+ years
• How to avoid becoming a forced seller in downturns
• Why Caprock buys secondaries 19 out of 20 times
• Tax tools: QSBS, Opportunity Zones, PPLI, 130/30 overlays
• Why privates matter: many top companies now stay private longer

Guest Bio:

Gregory Brown is Co-CEO of Caprock, an SEC-registered multi-family office. Previously, he was an active investor and entrepreneur with experience in product & business development strategy, capital formation, and mergers & acquisitions. He holds a B.S. from the University of Idaho and dual MBAs (Columbia Business School and Haas School of Business, UC Berkeley). Greg is based in Seattle. Outside work he enjoys golf, skiing, cooking, and playing drums in a band. He also serves on the board of La Plaza International.

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(0:00) Preview (0:24) Negotiating better economics through pooled capital (1:03) Introduction to Greg Brown and Caprock's overview (2:27) Scale, scope, and roles differentiation at Caprock (3:46) Client liquidity needs, cash management, and spending (6:25) Private market investment trends and challenges for high net worth families (9:53) Managing administrative complexity and client cash flows (12:13) Caprock's comprehensive service offerings (13:12) Pooled capital: Advantages, disadvantages, and interval funds (17:53) Cash flow and liquidity management best practices in family offices (20:24) Liquidity issues and solutions in private equity markets (25:33) Secondary market and tax considerations for investors (28:15) Tax loss harvesting, leveraged equity strategies, and private market investment rationale (34:35) Diversification and democratization of private markets (36:45) Opportunities and concerns in private credit and tax planning with PPLI (40:08) Lessons from founding Caprock and scaling venture co-investments (45:56) Closing remarks