The Ledger

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Disclosure
G Squared lost 20% on Uber and made 3x on Lyft
“We lost I think we made, we lost like 20 cents on the dollar, and Lyft we made like a three X.”
Larry Aschebrook Jun 16, 2025 ▶ 31:32 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared outsourced early investment committee memos to analysts in India
“My early investment committee memos and the early vintages were outsourced to, you know, a group of really smart analysts in India, that you could pay a fraction of what you could pay talent in the US.”
Larry Aschebrook Jun 16, 2025 ▶ 10:42 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared concentrates 80% to 90% of its risk in 10 companies
“And still to this day, which some people are not comfortable with, 80, hopefully 90% of our risk are in 10 companies.”
Larry Aschebrook Jun 16, 2025 ▶ 13:15 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared agreed to a $150M Spotify deal with a $125M fund
“Before we left the meeting, they were like, do you think you could buy a hundred and fifty million dollars worth of stock? And I said, sure. And I didn't have the money, because we were in the process of raising the fund, and I think we had like closed on a hu…”
Larry Aschebrook Jun 16, 2025 ▶ 22:39 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
Getir investment cost G Squared $500M in capital and LP churn
“In that case, from that fund, my guess is those decisions we made cost our partnership probably a half a billion dollars of capital. Between capital actually lost, and investors that you can't bring back.”
Larry Aschebrook Jun 16, 2025 ▶ 1:14:30 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared allocated 40% of its third fund to Spotify
“40% of my third fund went into Spotify.”
Larry Aschebrook Jun 16, 2025 ▶ 27:20 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared generated $1 billion in LP returns from Spotify
“We then went on to become a top 10 global shareholder of Spotify. We went as far as to putting up signs in their break room. We'll buy your shares, buying all these odd lot transactions along the way and built a huge position. And it ended up being like a bill…”
Larry Aschebrook Jun 16, 2025 ▶ 27:00 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared bought Spotify secondary stock at a 50% discount
“We bought it like a 50% discount to the current financing round. And we just kept buying it there for the next two years.”
Larry Aschebrook Jun 16, 2025 ▶ 28:33 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared sold massive holdings during the 2020-2021 peak
“Oh, just massive amounts. I mean, we made ridiculous sums of money for LPs. In that period, which set our business up to be able to survive a bad vintage, and we're working our tails off, our asses off on our twenty-twenty vintage, but it's hard.”
Larry Aschebrook Jun 16, 2025 ▶ 35:15 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared lost $400 million of LP capital on investments
“Yeah, it's a big win, but hey, we also lost. Four hundred million dollars of their money over here.”
Larry Aschebrook Jun 16, 2025 ▶ 35:47 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared made a 3x return selling Palantir stock at $9
“I sold it at like, I think we made a three X on it and sold it at like nine dollars a share.”
Larry Aschebrook Jun 16, 2025 ▶ 38:32 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared's 2020 fund comprised 70% primaries and 40% structured equity
“And so that vintage of all of our vintages has 70% primary. With, and 40% of that has structure.”
Larry Aschebrook Jun 16, 2025 ▶ 46:28 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
Aschebrook personally paid millions to settle a Theranos secondary deal dispute
“And then actually I don't think it was formally sued. It was threatened to be sued. And I agreed to settle it out of court and gave him a couple million dollars to go away.”
Larry Aschebrook Jun 16, 2025 ▶ 56:38 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared agreed to buy $50M in Theranos secondary stock
“The agreement was to buy about fifty million dollars of stock over, like, four months, because, you know Because I, because I'm still raising the fund.”
Larry Aschebrook Jun 16, 2025 ▶ 58:10 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared sold its final 23andMe shares at 70 cents
“We can start selling at seven, which would have meant I'm about a two X. I think I sold the last share at 70 cents.”
Larry Aschebrook Jun 16, 2025 ▶ 1:01:14 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared stopped share distributions to LPs to avoid blame
“We stopped distributing shares because LPs blame you if they hold it.”
Larry Aschebrook Jun 16, 2025 ▶ 1:05:54 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared is actively buying secondary shares in Anthropic, OpenAI, and Databricks
“A lot. A lot. And I've got appetite for more. Same with OpenAI. Same with Databricks. Wiz.”
Larry Aschebrook Jun 16, 2025 ▶ 1:25:18 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared acquired a large stake in Anthropic via FTX bankruptcy auction
“You know, we were fortunate enough during, you mentioned FTX earlier, to be awarded during the bankruptcy a bunch of stock. We bid on it. We went through the whole process, bid on the stock, bought a big chunk, and now the company, look, the company is, in my …”
Larry Aschebrook Jun 16, 2025 ▶ 1:26:39 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
Aschebrook began investing by buying stock from Jack Ma's family office
“I just started buying Twitter shares and Alibaba stock from Jack Ma's family office, and then holy shit, it worked.”
Larry Aschebrook Jun 16, 2025 ▶ 4:35 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared raised $1.4B and rejected $700M in 2021
“We raised a 1,000,000,004 and then turned down another seven hundred million. In very short period of time.”
Larry Aschebrook Jun 16, 2025 ▶ 9:13 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared made a 3x return on Wiz in 18 months
“It starts to provide you that Trojan horse moment to know when to triple down on a whiz, which we did in our 20, 22 vintage fund, and have the outcome that we're gonna have. Those founders are amazing, but to make three X in 18 months, Is because of what they …”
Larry Aschebrook Jun 16, 2025 ▶ 18:52 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared raised $700 million in Spotify co-investment vehicles
“And in that you take a lot of concentration in Spotify, but on top of the concentration we had, we did another seven hundred million in co-invest.”
Larry Aschebrook Jun 16, 2025 ▶ 29:12 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared rarely holds post-IPO stock, preferring pre-IPO sales
“Rarely do we hold posts public. Oftentimes we sell before they're public, and as it went public at the price it did, on a converted basis we were underwater.”
Larry Aschebrook Jun 16, 2025 ▶ 31:22 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared eliminated gut feel from its investment process after 2021
“I think we had to really adjust ours after 20, 21, because I think it had holes in it that were Exacerbated. Too much qualitative. Too much my gut, my feel. Too much who else is in the room. Too much, yeah, just the soft stuff that venture capitalists and grow…”
Larry Aschebrook Jun 16, 2025 ▶ 33:31 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared generated a 3x net return on Toast
“Toast, awesome business. It's like, three X net, and started in 2018.”
Larry Aschebrook Jun 16, 2025 ▶ 1:02:09 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared put $200M total risk into Gorillas and Getir
“The total first was, it was like, fifty million bucks in total between secondary and primary, kind of, we got that plus sum and value of Gatir, and then the next check was a hundred million bucks. To restructure that equity, to pull it forward. So you get two …”
Larry Aschebrook Jun 16, 2025 ▶ 1:10:23 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared bought Bolt at $20 per share before Sequoia paid $260
“I think it was like, 20 bucks a share or something, and Sequoia did it at two 60.”
Larry Aschebrook Jun 16, 2025 ▶ 1:32:21 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared made 8-10x on Spotify and 6-7x on Bolt
“Spotify, early investment that he trusted our business model in, let's say eight to 10 X. Bolt, you have to be determined, but let's just assume it's somewhere between, you know, 50% and face value of what Sequoia paid. It's, you know, six, seven X.”
Larry Aschebrook Jun 16, 2025 ▶ 1:33:14 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared invested in Monzo at a sub-$4B valuation
“Oh, sub four billion.”
Larry Aschebrook Jun 16, 2025 ▶ 1:21:36 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Disclosure
G Squared holds investments in GPU cloud providers Lambda and CoreWeave
“That's why we have Lambda. We also had CoreWeave.”
Larry Aschebrook Jun 16, 2025 ▶ 1:27:36 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
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