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The best operators have a relentless focus on leverage, finding ways to multiply their impact rather than just working harder. But here's what I see happening in finance teams everywhere. Brilliant people getting buried in expense management busy work. If you think about it, you become a finance leader because you love strategic work. Modeling scenarios, optimizing capital allocation, finding the insights that actually move the business forward. But instead, you're chasing receipts and categorizing transactions. It's the opposite of leverage. This is exactly why I'm so bullish on what the team
Patrick O'Shaughnessy is the CEO of Positive Some. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of PositiveSum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of PositiveSum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.
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First of all, it was an eye opener to me when it happened and we had a small strategy that I always envisioned could be a big strategy, but maybe to go backwards and say, what are the best private equity venture deals of all time? This is a cheat answer. It's not the real answer, but in my own view, probably the most cleanest best example of return is probably VMware. Technically, EMC was the private equity buyer. It's about $650,000,000 and sold it for 60,000,000,000. So that's a $60,000,000,000 gain plus or minus. You could argue Instagram billion to probably a trillion. YouTube is probably
the largest funds in our industry, 10 plus billion, 20,000,000,000. What size would you set a fund, a 100,000,000,000 or some other number, if you wanted to do today in 2025, the thing you just described? How big would it have to get so that you were actually competitive? Today's tougher.
This was probably 2016 when the Vision Fund came around. The concept of liquidity, billion dollar exits as a massive victory for the venture. To get Benchmark or Sequoia to sell something for a billion dollars probably doesn't get their heart rate up today. So the likelihood that they would do those deals again today, what the world looks like and what the upside could be for these types of assets is pretty small. It's just a little bit harder because the scale has changed, but we look for these sub a billion is really the sweet spot that we could consider, but to find hyper growth shareholder
So if you were to size a fund today for the best possible risk adjusted return, where like fund size dictates the strategy, where do you think you would size it?
I think we're pretty close. What's your marginal one? We're about 12,000,000,000. We're deploying 3 plus billion a year in invested capital across a range of strategies, but we definitely don't feel capital constrained to the opportunity set. I think if we were to and I don't think this is part of our strategy, lean in on some of th
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