In this interview for the Billionaire Brain Trust series, family‑office advisor Steve Woodruff talks with Andrew Eberhardt, CIO of a single‑family office and managing director of Wingspan Capital, at the Family Office Club Single Family Office Summit in New York. Eberhardt explains why his family office has allocated 100% of its capital to alternative investments, a move he sees as part of a broader industry shift (average family‑office alternative exposure is about 45%). He contrasts the risk‑adjusted returns of alternatives—typically 10%+ with low volatility and decent liquidity—to the S&P 500, which offers similar nominal returns but with far higher volatility. He highlights the performance resilience of his office’s portfolio through market downturns in 2021‑2023. The conversation then moves to private credit, where Eberhardt notes that recent higher rates boosted yields, but the space is now over‑capitalized, leading to compressed returns in larger funds while niche, smaller‑cap private‑credit opportunities still deliver low double‑digit, after‑tax returns. He stresses that private‑credit returns are effectively reduced by about 40% after taxes, a factor often overlooked. Looking ahead, Eberhardt discusses two emerging focus areas: (1) real‑asset and infrastructure investments—such as shipping containers, farmland, rail cars, and barges—that provide stable cash flow, low‑double‑digit returns, and tax efficiency; and (2) the intersection of Silicon Valley technology startups with the U.S. Department of Defense (DoD). He argues that this niche is under‑capitalized, offers national‑security relevance, and requires specialized expertise to navigate government procurement, making it an attractive thematic play for his office. Throughout, he acknowledges macro uncertainty—geopolitical risk, election cycles, and unpredictable interest‑rate trajectories—as a constant backdrop influencing allocation decisions.
Chapters
You can get a 10%+ return without a lot of risk, and it's fairly liquid. The family office I work with is 100% in alternatives, so no public market exposure at all. And I think that is a real trend in family offices. Family offices, I read on average, 45% in alternatives, and this family has taken that 100%. If you marry that up against the S&P 500, you get a 10% return as well with a lot of volatility. Wow, volatility. So given that choice, logical that you go here. I don't think we've assimilated that as an industry. It's much more comfortable. And you look at 2022, that was a— what, market was down 20% and they were 10%, exactly what they were in 2023 and exactly what they were in 2021. Yes, that steady—
I'm sure they were.
Welcome to Billionaire Brain Trust, our newest YouTube series that will take you behind the scenes into candid conversations with billionaires and those who work with them, hosted by Steve Woodruff, who brings a unique perspective as a family office advisor. Billionaire Brain Trust will feature exclusive interviews with billionaires and the key players in their organizations, offering viewers a rare glimpse into their stories, decision-making frameworks, and what they are excited about right now. Whether you're an aspiring entrepreneur, a seasoned investor, or simply curious about the world of the ultra-wealthy, Billionaire Brain Trust will help you think bigger and achieve more.
We are in New York, uh, we are with the Family Office Club Single Family Office Summit. I'm joined by Andrew Eberhardt. Very excited to talk with you. And Andrew is a CIO for a single family office, also the managing director of Wingspan Capital. Uh, pretty interesting background. I got to hear him speak a little bit earlier today, but very focused on alternative investments, which we love. So appreciate the opportunity to talk with you.
Thank you, nice to be here.
Yeah, excellent. So one question in particular: why is it that you focus on alternatives so heavily? What— why is that important to you?
Well, the family office I work with is 100% in alternatives, so no public market exposure at all, and I think that is a real trend in family offices.
Yeah, it is, right?
Family offices, I read on average 45% in alternatives, and this family has taken that 100%. 100%. And I think you're going to see that more often. Why is that? Well, if you look at alternatives sort of writ large, yeah, you can get a 10% plus return without a lot of risk, and it's fairly liquid.
Sure.
If you marry that up against the S&P 500, you get a 10% return as well with a lot of volatility. Wild volatility. So given that choice, you know, to me it's logical that you go here. I don't think we've assimilated that as an industry.
Yeah, that makes sense.
It's much more comfortable. And the family's been really happy with this. And you look at 2022, they were invested and that was a— what, market was down 20% and they were 10%, exactly what they were in 2023 and exactly what they were in 2021. Yes, that steady—
I'm sure they were. Yeah, I'm sure they were very happy to see that.
Yeah.
And you're the guy for the job. You, uh, you've been focused on, on alternatives for a long time, and I know you've worked with a number of other family offices as well, so you have a lot of experience in working with families and pairing that with alternatives.
That's because I'm older.
Yeah. That's great. But we appreciate that you're bringing that experience and able to bring that expertise.
Yeah, thank you.
There's a lot going on. Interest rates starting to come down a little bit.
Right.
Major election. Right. A lot of uncertainty.
Yeah.
Does that change what you're focused on at all?
Well, yes, I think the uncertainty is always going to be there, geopolitical, and we don't know how to handicap that. We can't really predict that. So, yeah, yeah, we control what we know or can control. And I think, you know, private credit really benefited from the higher rates of the last few years.
That's right.
It's become, you know, the investment du jour. It's overcapitalized. There's too much product out there. You're seeing returns compress, particularly in the larger funds.
Yeah.
And direct lending, bank loans. It's, it's not— you're going to get high single digits. Private credit still down in the smaller niche investment. There is a lot less capital available. It's less competitive. You can get the low double-digit returns. So, you know, I think if you're in private credit, you want to be looking in that space.
Yes.
Keeping in mind that any return you get in private credit is discounted by about 40% for the taxes. And I think that gets lost in the shuffle sometimes.
Yeah.
You look at the headline number and that's attractive.
Sure.
The after-tax number, not so much. Now, rates, if they are in fact coming down, who knows? Now, private credit's not going to look as good as it did. Who knows where rates are going to go? I think nobody can call that. Even Jay Powell doesn't get that right. So So who are we to think we can get it right? So we're looking at other asset classes. We already have full exposure to private credit, and we're glad to have that. But, you know, where, where else can we go to get ahead of that curve?
Yeah.
And we're looking at real—
what else are you excited about right now?
Oh, infrastructure, real assets. And, and these are asset classes where, where you can get a low double-digit return but often tax efficient. So you can— buying and leasing hard assets, maybe shipping containers, farmland, you could do rail cars, barges. All those things give you that low double-digit return, stable, steady cash flow that you can lever, and they're depreciable, so very tax efficient versus private credit. So that's an area. And then thematically, we're looking at investing in the, the the intersection of Silicon Valley and DOD.
Interesting.
So Silicon Valley typically historically has created applications for the commercial market.
Yes.
But DOD is a huge spender. It's the biggest spender in our budget. They need that technology. And those two worlds have not historically intersected. It's, you know, the big prime A&D, Lockheed, Boeing.
Yeah.
And then you got all this entrepreneurial startup. They have different cultures and this is bureaucratic, this is more disruptive. But technology here is now realizing that not just is that a commercial application, it is a DOD and national security more broadly. So that theme, whether it's private credit, whether it's venture, we are very much focused on that. It is underserved, undercapitalized, and not well known, and it's hard. To deal with the government. Yeah, is hard. So you need a team that's particularly well qualified, but that's, that's an area where we come in.
Excellent. Thank you, Andrew. Appreciate it so much. Thanks for taking the time.
