Podcast Summary

How I Invest with David Weisburd — E214: Inside Look into a $14B Multi-Family Office

Date: September 17, 2025
Host: David Weisburd
Guest: Greg Brown, Co-Founder & Co-CEO of Caprock

Episode Overview

In this episode, David Weisburd speaks with Greg Brown, co-founder and co-CEO of Caprock, a multifamily office overseeing $14B in assets under advisement. The discussion focuses on how Caprock serves ultra-high-net-worth families with world-class access to private markets and tax-efficient, bespoke investment strategies. Greg shares insights into the practical realities of managing wealth across generations, building institutional-grade endowment-style portfolios for clients, navigating private markets, handling tax and liquidity challenges, and the operational complexities behind large family offices.

Key Discussion Points & Insights

1. The Role and Approach of Caprock ([01:25])

• Caprock’s Mission: Serve ultra-high-net-worth families with personalized, tax-efficient investment access, especially to private markets.

  “We think of ourselves really playing two roles. We're the family chief Financial Officer and Chief Investment Officer... Our clients as the CEO and in most cases that's multi-generational in scope and scale and duration...” (Greg Brown, 01:25)

• Client Scope: Over 400 families, 11 offices across the US.

• Bespoke & Values-Aligned: Solutions are tailored per client, focusing on both financial and personal priorities.

2. Family Office: CFO vs. CIO Functions ([02:36])

• CFO Hat First: Deeply understand and forecast the entire family balance sheet, including “things we don’t control” (operating businesses, real estate, spending, future liquidity needs).

• CIO Afterward: Only then allocate assets, ensuring long-term sustainability and margin for error.

  “It’s really about forecasting future liquidity management ... so that those future obligations, particularly to the things that are not liquid, are done with a margin for error...” (Greg Brown, 02:47)

• Upfront Discovery Process: Extensive engagement with families to map out all cash consumption points, burn rate, gifting intent, and more.

3. Why Invest in Private Markets? ([31:39])

• Growth Opportunity: Private markets drive a major portion of US business growth; 87% of US companies with >$100M revenue are private.

  "The average new public company now is over 12 years old… companies like SpaceX, Anduril, OpenAI, and Stripe are worth tens of billions while still private. If you're waiting for those companies to become public, you're missing out on years of growth." (Greg Brown, 31:51)

• Diversification Reality: Today's truly diversified portfolio requires private market access, as public listings have shrunk and changed in nature ([34:40]).

4. Who Can Access Private Markets? Minimums & Complexity ([06:25])

• Practical Threshold: Portfolios with $10M+ investable assets can start to benefit from private market and “endowment-style” investing, though more scale improves efficiency and access.

• Complexity Challenges:

  • High minimums, fund access barriers, administrative load
  • Need for infrastructure to track capital calls, tax documents, liquidity, and blended cash flows
  • Caprock’s value is reducing “the administrative complexity tail wagging the dog”

  "Doing private investing ... is easy to deploy capital in private markets. It’s hard to do it well with top quartile managers for many reasons." (Greg Brown, 08:14)

5. Operational Scope: Where Caprock Engages ([10:03])

• Services Include:
  • Full cash flow tracking across entities
  • Tax and return characterization of every inflow/outflow
  • Macro and client-specific portfolio construction (CIO role)
  • No concierge services: don't "walk dogs," but will help buy homes/planes, structure financing, etc.
  • Target: Do a lot for a small elite group, not thinly for many

  "We're not trying to do what we do for everyone. We're trying to do a lot for a small number of families versus the inverse..." (Greg Brown, 10:19)

6. Scale: Pooling Capital and Access ([13:12])

• Benefits of Scale:

  • Pooling capital ($14B AUA) allows negotiating better fees/terms, gaining coveted fund slots, and participating in co-investments.
  • Caprock uses “fee free and carry free” pooled vehicles—“exceedingly rare in our industry”—letting clients access top-tier deals (e.g., SpaceX, Anduril, Palantir, Anthropic) directly ([13:35])

  "We've done seven vintages of pooled vehicles ... all fee free and carry free to our clients. That alone is exceedingly rare..." (Greg Brown, 13:35)

• Downside of Pooling: Not directly discussed as a disadvantage; implies that increasing scale past a point can lead to losing the "personal touch" ([40:23]).

7. Liquidity & Cash Flow Management Best Practices ([17:53])

• Forecasting:

  • Short-term (next 6 mo): liquid assets (T-bills, money market)
  • Mid-term (6-18 mo): semi-liquid credit, redeemable funds
  • Long-term (2+ years): permitted to be illiquid
  • Avoid over-dependence on equity to avoid forced selling during market drawdowns.

  "What we don't want to be doing is redeeming or selling assets at the wrong time ... We want to be opportunistic buyers ..." (Greg Brown, 20:38)

• Risks: Selling equities in a downturn or overcommitting to illiquids in a low distribution (DPI) environment can trigger liquidity crunches and force asset sales at a discount.

• Secondaries:

  • A useful liquidity tool, but should ideally be a "buyer" for discounts rather than a "forced seller" ([24:22])

8. Tax-Aware Strategies for Ultra-High Net Worth ([25:34])

• Allocation is always on a post-tax basis: Analyze each investment’s tax impact, place income/yield in the right entity at the right time.

• Tax Optimization Tools:

  • Qualified Small Business Stock (QSBS)
  • Opportunity Zone funds
  • Tax alpha via long/short overlays (130/30, etc.)
  • Estate planning (SLATs, GRATs, CLATs, CRTs)
  • Private placement life insurance (PPLI)
  • Donor advised funds

• Tax Loss Harvesting & Overlays: Leveraged overlays like 130/30 can amplify tax alpha; these strategies harvest losses in all market regimes to offset high basis gains, but come with margin call risk ([28:37]).

  "In a normal tax loss harvesting separate account, you would see somewhere between 50 and 100 basis points of tax alpha ... in this 130/30 strategy, it's about three times that." (Greg Brown, 28:37)

9. Interval Funds & Democratization of Access ([15:28])

• Interval Funds:

  • Useful for small investors or firms lacking direct access, but their structure can create liquidity mismatches, "gating" risks, and drag returns.
  • Caprock uses them sparingly; prefers true illiquids with well-understood liquidity needs ([16:02])

• Democratization:

  • More access is socially positive, and the overall private market “pie” is growing enough that returns aren’t threatened by increased participation ([35:53]).

  "I think that the pie is growing fast enough that that's less of an issue ... More important than returns of the top 0.01% is just giving more people access..." (Greg Brown, 35:53)

10. Private Credit’s Hype & Use Cases ([36:16])

• Growth Engine: Shift from banks to private lenders creates opportunity.
• Risks: Needs careful tax planning due to ordinary income.
• Structures: Adoption of tax-advantaged wrappers (e.g., PPLI) to house income-yielding assets for tax efficiency ([38:15]-[38:50]).

11. Scaling the Family Office & Lessons Learned ([40:09])

• Early Days: Spent years educating the market on family office value and private markets; now, these concepts are “well understood.”
• Advice:
  • “Do it faster, be more bold” with internal investments.
  • Scale brings benefits up to a point, then risks losing the personal touch.
  • Caprock’s edge is still “do a lot for a small number of families.”

  "If I were to go back and replay... I think I would do it faster and be more bold in terms of internal investments to scale more quickly." (Greg Brown, 40:23)

12. Venture Co-Investments Model ([43:53])

• Approach: Offers both pooled and direct co-investments in high-conviction deals, without additional fees/carried interest for clients.
• Client Experience: Participation in the rise of “category winners” like SpaceX, Anthropic, etc., while being as close to direct as possible.

  “To be able to deliver things like SpaceX or Anthropic or ... direct to clients and in many cases direct to the cap table... That’s a pretty special opportunity.” (Greg Brown, 44:15)

Notable Quotes & Memorable Moments

• On Administrative Overhead:
  “There's a lot of complexity there and I think all of our clients appreciate what we do as a family office to make that look less difficult than it is.”
  (Greg Brown, 08:14)

• On the Value of Illiquidity:
  "We have great comfort taking on long term illiquidity elsewhere on the balance sheet when we already understand the things that are going to need liquidity near and long term."
  (Greg Brown, 05:28)

• On Co-Investment Opportunities:
  "We’ve done seven vintages of pooled vehicles ... all fee free and carry free to our clients. That alone is exceedingly rare..."
  (Greg Brown, 13:35)

• On Private Market Opportunity:
  “Private markets is just a really important place to be invested for those who can...”
  (Greg Brown, 31:51)

• On Learning & Growth:
  “For 16 years ... every investment in infrastructure and team and office ... was a personal capital call. I think that made us reticent to make too many investments at the same time…”
  (Greg Brown, 40:23)

Timestamps for Key Sections

• Introduction & rational for private investing: [00:36]–[01:25]
• Caprock’s structure, CFO/CIO roles: [01:25]–[05:04]
• Client engagement process & financial discovery: [03:45]–[06:25]
• Barriers and access to private markets: [06:25]–[08:14]
• Operational complexity & Caprock’s scope: [10:03]–[13:12]
• Pooling capital for access/terms: [13:12]–[15:28]
• Interval funds and liquidity: [15:28]–[17:53]
• Cash flow & liquidity strategies: [17:53]–[22:24]
• Secondaries and market timing risk: [23:56]–[25:34]
• Tax-aware portfolio management: [25:34]–[28:37]
• Tax overlays and harvesting strategies: [28:37]–[31:39]
• Macro case for private markets: [31:39]–[34:40]
• Democratization discussion: [35:40]–[36:45]
• Private credit discussion & PPLI: [36:45]–[40:09]
• Lessons from growth & scaling: [40:09]–[43:53]
• Venture co-investments philosophy: [43:53]–[45:56]

Tone Note

Greg Brown is detailed, candid, and practical, emphasizing stewardship and long-view alignment. Weisburd, as host, pushes for granular, operational answers, keeping the conversation focused on utility for sophisticated listeners.

Conclusion

This episode offers a comprehensive inside look at how a leading multi-family office manages complexity, private markets access, and tax-optimized strategies for ultra-high-net-worth families. Caprock’s approach, grounded in rigorous upfront analysis, large-scale pooled access, and client alignment, sets a high bar for bespoke wealth management. If you’re interested in how institutions and family offices approach private investing and wealth preservation, this is an essential listen.