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Larry Aschebrook

Founder & Managing Partner, G Squared · 1 appearance on the record.

computed by AI from the episodes · how this works → · full disclaimer →

investorfounder@LarryVCg2 ↗LinkedIn ↗gsquared.com ↗

Larry Aschebrook is the founder and Managing Partner of G Squared, a growth-stage venture capital firm founded in 2011. The firm specializes in direct secondary market investments and has backed companies including SpaceX, Palantir, and Uber.

54statements → 7claims → 5claims resolved → 60%fully supported → 4.15/5average certainty → 2.09/5average debate potential → 4.1/5argument clarity · the sources → 1said about them ↓

3 supported 2 partly supported 0 contradicted 2 not checkable as stated how the 7 claims stand · each chip opens the sources

7 assertions · 6 opinions · 10 insights · 30 disclosures · 1 what if · every statement was checked. The predictions and assertions are the 7 claims: statements the public record can support or contradict. 5 are resolved, and 2 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Larry argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
G Squared owned 16% of Coursera at its IPO
“We owned 16% of Coursera when it went public.”
Larry Aschebrook Jun 16, 2025 ▶ 41:50 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
none yet certainty 3
75% certainty 4
83% certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

Argument clarity: do they answer the question? how? →

4.1 / 5 directness 4.3 · coherence 4.1 · precision 4 · compression 3.6

redirected or did not address 1 of 39 assessed questions (3%). Watch them ▸

This is a score against a rubric. It is not a rank. Every host question → answer exchange is scored with names hidden on directness, coherence, precision and compression, 1–5 each, on meaning alone: disfluencies are ignored, and only raw unedited episodes count. This is the score that measures thought. Every scored exchange, scores shown → · The rubric and its checks →

How they sound: speaking style how? →

272 words/min while actually speaking · 13.5 um and uh per 1k words · 21.2 false starts per 1k · 27.7% of pauses land inside a clause

Measured by listening to the audio itself: 16,053 words across 1 episode of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

How the interview went all their pushback → series average →

Across 1 rated episode:

host pushback ▾ 4/10
pushed back at the host ▾ 3/10
setup questions received 35%

Everything Larry Aschebrook said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Opinion
Kleiner Perkins sold G Squared terrible early cleantech deals
“And there were some dogs in there, some cleantech shit that Kleiner Perkins sold me that was just a flaming bag of turds on your front porch.”
Larry Aschebrook Jun 16, 2025 ▶ 14:05 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
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
Opinion
Silicon Valley exhibits sheep-like herd mentality in secondary trading
“One of the issues with Silicon Valley, one of the benefits of being in Chicago is we isolate ourselves a bit from the herd mentality. And it's like, sometimes it's like sheep. They just jump one on after another and they buy more stock and things that you see …”
Larry Aschebrook Jun 16, 2025 ▶ 31:49 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Opinion
Anne Wojcicki was a visionary founder but not a great public CEO
“You got Ann Wojciechowski, who's a fantastic founder, in my opinion to not maybe a great public CEO, but awesome founder and visionary of what she wanted to build and the ability to go do it.”
Larry Aschebrook Jun 16, 2025 ▶ 1:00:51 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Opinion
TVPI and MOIC are fake venture performance numbers
“I mean, my belief is that TVPI and MOIC are not the stats that people should be focused on, and they are. I don't, I think they're fake numbers.”
Larry Aschebrook Jun 16, 2025 ▶ 1:44:47 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
Insight
Growth VCs miss 2.5x net targets if entry valuation is off
“Because at our stage, unlike yours, which it doesn't, you know, from your seat, in a lot of ways I envy your seat, because if you pay 50 pre or a hundred pre, if it's a good business, you're still gonna make a five X. A 10 pre, 50 pre, does it really matter fo…”
Larry Aschebrook Jun 16, 2025 ▶ 34:10 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Insight
VCs should dollar-cost average out of positions post-IPO
“Dollar cost average out just like your dollar cost average in and just start getting liquidity when you can privately and continuing it through when they list.”
Larry Aschebrook Jun 16, 2025 ▶ 1:01:39 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Opinion
Getir's main mistake was expanding beyond low-labor-cost Turkey
“I think the mistake the company made there was it left Turkey and didn't focus maybe on other markets that were similar to Turkey from a employment cost perspective.”
Larry Aschebrook Jun 16, 2025 ▶ 1:13:10 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
Insight
VC funds should only offer co-investments on core fund deals
“The way we run it today is the way I think people should run their, only in conviction, when your funds are investing alongside of it, that's when you do the co-investment. You don't do it the way we did it in twenty-twenty.”
Larry Aschebrook Jun 16, 2025 ▶ 1:17:53 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Insight
Growth investors should focus on absolute dollar prices and DPI, not dilution
“I don't give a shit about the dilution. I care about the price I pay. In dollars. And the price I'm going to sell it at, in dollars. I am focused on DPI, not MOIC. I don't care about the dilution.”
Larry Aschebrook Jun 16, 2025 ▶ 1:24:54 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Insight
Hundreds of legacy private tech companies are 'zombies' doomed by AI
“You have incumbents that are large. We call them, there's two types of companies that were, that are big and private that aren't in AI. They're kind of, we talk internally, we call them vampires and zombies. Because they're massive. Many of them are profitable…”
Larry Aschebrook Jun 16, 2025 ▶ 1:28:34 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Opinion
Offloading $1B of Anthropic stock in private markets is extremely difficult
“Today I think there's a handful of liquid private companies basically. They're quasi-liquid. But at scale. Small positions, yes. But try to go move a billion dollars of Anthropic.”
Larry Aschebrook Jun 16, 2025 ▶ 1:30:43 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Insight
VC funds must sell winning companies to build a sustainable business model
“Sell, you know, sell your dogs and keep your winners, and I think it's actually the, it's somewhat of the inverse, is you have to be able to, willing to sell your winners. To have a sustainable business model. And to generate the return that will actually driv…”
Larry Aschebrook Jun 16, 2025 ▶ 1:31:17 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
Assertion Not checkable as stated
G Squared acquired early secondary shares at 35 cents on the dollar
“In early vintages, we got like 35 cents on the dollar by being a secondary direct buyer over primary buyers because there was no other secondary buyers.”
Larry Aschebrook Jun 16, 2025 ▶ 15:54 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

Show 24statements(30 left)

The other half of the tape: Larry Aschebrook's own voice is left out of every number here. Other people bring the name up 1 time in 1 episode on 20VC. every mention, with the transcript →

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Appearances (1)

EpisodeDateSpeaking time
Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on L Jun 16, 2025 1h 17m
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