Episode summary
What Billionaires are Investing into Today (April 2026)
How I Invest With David Weisburd
· · 33 min · Hosts: David Weisburd · Guests: Douglas Evans
Summary
Douglas Evans argues that ultra-high-net-worth families should invest more like institutions: with long horizons, tolerance for illiquidity, and a framework built around portfolio construction rather than chasing hot labels. He says taxable families can especially benefit from venture and other early-stage strategies because tax treatment can amplify compounding, but only if they think in decades and choose the right sectors, business models, and partners.
A major theme is private capital pacing. Evans says venture returns are highly sensitive to vintage-year diversification, capital calls, and the timing of deployments, so families starting from scratch need an explicit pacing plan and often begin with secondaries or broad funds before building direct relationships. He also says the classic Swensen-style allocation model is under strain because DPI has fallen sharply, with 2024 and 2025 both around 9% versus a roughly 24% assumption embedded in older models.
Evans expects more liquidity tools to emerge, including broader private-market exchanges, stronger secondary markets, and continuation vehicles. He sees those structures as a way to create price discovery, recycle capital, and better align GPs and LPs in a market where many great companies are staying private much longer. His favorite underloved area is enterprise infrastructure and security, especially as AI, automation, and robotics increase risk.
Key takeaways
- Evans says ultra-wealthy families should invest like institutions, using long horizons, illiquidity tolerance, and taxable-portfolio awareness.
- He says venture investors need private capital pacing and diversification across about six to seven vintage years to avoid timing risk.
- Evans argues the old Swensen framework is breaking because DPI has fallen to about 9% in 2024 and 2025, far below the model’s historical assumption.
- He expects secondary markets and continuation vehicles to expand as private-market liquidity tools that create price discovery and recycle capital.
- Evans sees enterprise infrastructure and security as an underloved opportunity set because AI and automation raise the stakes for safety and resilience.
Notable quotes
“ultra high net worth really can and should invest more like an institution”
“you need to have an overall game plan. And that game plan is going to lay out uh what we call private capital pacing”
“the best vent vintages do actually follow the worst vintages”
“there's really only two asset classes. There's really only debt and equity. There really isn't a third”
“The worst thing you could do is to to take equity-like risk with debt-like returns”
How the episode opens
So Doug, you're the CIO of a $10 billion multif family office. How should large family offices go about investing their wealth?
It's a good question and tends to be part of the differencem on how we approach investing for the ultra fluent, but it comes down to pretty simple thesis that the ultra high net worth really can and should invest more like an institution. And what I mean by that is is that ultra net worth families have the scale, the time horizon, ordinarily a a tolerance for ill liquidity that's more akin to sophisticated institutional investors and less like mass affluent investors. So we at Kellen Family Office, we've built a framework around that idea and we've gathered what we think are the important elements that support the access and portfolio construction to bring those kinds of opportunities to them and then bring it to bear inside of a taxable environment.
It it's interesting because I I just spoke to Jason Pritzkar and his grandfather started the the Pritskar family and was a the gen one in the family and at that point there was 70% 70 capital gains. He was working under that constraint. So he figured out I want to invest into companies that I'm not going to flip in three years like traditional private equity today but what are the companies that could compound for many decades that I wouldn't have to sell that could basically compound taxfree and then he went upstream of that what are the kind of decisions I would make if I was investing to companies I want to compound for for two three decades and essentially came down to the right sector the right business model but also the right team what kind of partner would you want for 20 30 years it seems very simple to think about taxable versus non-t taxable portfol portfolio, but the downstream consequences of this one diff difference in the portfolios changes the portfolio dramatically.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- family office investing
- private market pacing
- venture capital vintage years
- continuation vehicles and secondaries
- tax-aware investing
Companies and tickers mentioned
- Callan Family Office
- AlphaSense
Watch the episode
Watch “What Billionaires are Investing into Today (April 2026)” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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How I Invest With David Weisburd, this episode and its artwork belong to David Weisburd. Octagon is not affiliated with the show; this page is an independent summary.
