Episode summary

Why Billionaires Invest Differently w/Robert Blabey

How I Invest With David Weisburd · · 29 min · Hosts: David Weisburd · Guests: Robert Blabey

Why Billionaires Invest Differently w/Robert Blabey – How I Invest With David Weisburd

Summary

Robert Blabey argues that family offices are a distinct investing ecosystem because many have institutional-scale capital without institutional-scale resources. Align was created to sit in that gap, first as a specialist serving families and later, from 2019, as a small opportunistic investment platform built around absolute returns.

He says the firm’s best terrain remains private credit, especially bespoke transactions where Align can underwrite directly rather than join large syndicates. More broadly, Robert Blabey describes a disciplined inbound process: families often bring ideas as collaborators, not pitchers, and that cooperation produces narrower, more curated deal flow than the institutional world.

Across asset classes, the core rule is downside-first thinking. Robert Blabey says every investment is stress-tested for how quickly capital can be hurt, with shorter duration used as a practical way to reduce risk and keep capital available for dislocations. He also argues that family offices are more willing than institutions to co-invest, trade size for flexibility, and build portfolios around alternatives rather than isolated bets.

Key takeaways

  • Robert Blabey says Align was built to address the mismatch between family office goals and the resources they actually control.
  • Robert Blabey still prefers private credit because bespoke, directly underwritten deals can offer risk-adjusted returns.
  • Robert Blabey says family-office deal flow is more curated and collaborative than institutional pitching.
  • Robert Blabey’s north star is downside protection: every investment is stress-tested for how quickly capital can be hurt.
  • Robert Blabey favors 1-to-5-year opportunities because shorter duration can reduce exposure and keep capital ready for shocks.
  • Robert Blabey says he is better at replicating an alternatives portfolio than building exposure to venture or municipal bonds.

Notable quotes

“family offices are the only um sort of large industry I'll call it participant that I'm aware of that you can't sort of evaluate the business from the outside”

— Robert Blabey

“we've been able to to execute on a number of transactions over the last gez longer longer than the fund uh has been in existence”

— Robert Blabey at 2:30

“we look at every investment that we do and we approach each investment with how quickly can we get hurt”

— Robert Blabey at 6:14

How the episode opens

So you were the CIO of several family offices before starting a line. What gap did you see in the market that led you to start a line in 2014?

I feel like family offices are the only um sort of large industry I'll call it participant that I'm aware of that you can't sort of evaluate the business from the outside. What we saw when we started a line was that, you know, often times there was a mismatch between what the family hoped to get from their family office and what their goals were and what their internal resources allowed for. And so I come from a institutional background originally and you know a lot of these groups quite frankly have institutional level capital and they don't always have institutional level resources and so were it to be a commercial business I think they would probably run themselves very differently and these are these are intentional decisions that are made by the families and there's no it's it's not to say that there's a negative to it but there is a business opportunity we felt uh in that um in that space and so that's uh what what we started a line to to address and that was you 2014, so a while ago.

And how would you describe Alliance's value proposition in a sentence or two? What what is it that Allian does exactly?

Align started out originally, I'll call it, as a as an adjunct or sort of a specialist in that category between where family offices uh head desires and and lack the resources to accomplish their goals. And so that's really where we started. And the way align now has evolved and starting in 2019 evolved very like in a very deliberate fashion was um through now an investment platform uh fund business uh that um that currently has just uh just three limited partners, myself, my partner and a line and another family.

From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →

Topics

  • family office investing
  • private credit
  • downside protection
  • opportunistic investing
  • private market alternatives

Companies and tickers mentioned

  • Align

Watch the episode

Watch “Why Billionaires Invest Differently w/Robert Blabey” on YouTube

Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.

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