E141: State of Series A's, VC dry powder, IPO window opens + more with Bill Gurley & Brad Gerstner
David Friedberg (host), Chamath Palihapitiya (host), Jason Calacanis (host), Narrator, David Sacks (host), Bill Gurley (guest), Brad Gerstner (guest), David Friedberg (host), Brad Gerstner (guest)
In this episode of All-In Podcast, featuring David Friedberg and Chamath Palihapitiya, E141: State of Series A's, VC dry powder, IPO window opens + more with Bill Gurley & Brad Gerstner explores venture Reset: Series A Reality, Dry Powder Myths, IPO Reckoning Arrives The episode brings Bill Gurley and Brad Gerstner together with the All-In crew to dissect today’s venture landscape, from Series A dynamics to late-stage distress and the reopening IPO window. They argue that while new early-stage deals have stabilized near pre-pandemic norms, hundreds of overvalued 2020–2021 ‘unicorns’ now face painful down rounds, structural cap-table problems, or forced IPOs. The group unpacks the misconception of VC “dry powder,” explaining LP constraints, distorted marks, and why many funds are deliberately deploying slowly. They also touch on the macro backdrop—disinflation, rising effective rates, record debt—and sprinkle in discussions on biographies, craft, and career advice as context for how great investors and operators think.
Venture Reset: Series A Reality, Dry Powder Myths, IPO Reckoning Arrives
The episode brings Bill Gurley and Brad Gerstner together with the All-In crew to dissect today’s venture landscape, from Series A dynamics to late-stage distress and the reopening IPO window. They argue that while new early-stage deals have stabilized near pre-pandemic norms, hundreds of overvalued 2020–2021 ‘unicorns’ now face painful down rounds, structural cap-table problems, or forced IPOs. The group unpacks the misconception of VC “dry powder,” explaining LP constraints, distorted marks, and why many funds are deliberately deploying slowly. They also touch on the macro backdrop—disinflation, rising effective rates, record debt—and sprinkle in discussions on biographies, craft, and career advice as context for how great investors and operators think.
Key Takeaways
Series A has cooled but remains competitive, especially outside AI.
Median Series A rounds and valuations are down versus 2022, yet Bill Gurley notes the market has not reverted to 2010-era austerity—top-tier A rounds, particularly in AI and infrastructure, still see strong competition and elevated pricing.
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Many ‘unicorns’ are structurally trapped and will need painful resets.
Companies that raised huge late-stage rounds at extreme valuations now have complex cap tables and large liquidation preference stacks; new private money often avoids these situations, pushing them toward recaps or down-round IPOs to ‘clean up’ and reset reality.
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VC ‘dry powder’ is committed, not sitting in GP bank accounts.
Capital is called from LPs over years, not front-loaded, and LPs face their own liquidity, denominator, and bonus-linked marking incentives—so the idea of a guaranteed wall of money rushing back into startups is overstated.
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Fund deployment pace is slowing as GPs protect franchise survival.
Younger funds and expanded platforms are stretching out deployment (e. ...
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The IPO window is cracking open—expect both premium and down-round IPOs.
With software multiples normalized and M&A constrained by regulators, high-quality names like ARM and Instacart are preparing to go public, often at major discounts to their last private valuations, which will reset cap tables and reprice late-stage paper.
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For LPs, venture must beat liquid tech indices, not just the S&P.
The group highlights data showing that simply owning and rebalancing into top tech names or QQQ produced massive multi-decade returns; illiquid VC needs to clear a high bar (e. ...
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Macro signals show disinflation alongside very tight financial conditions.
Core CPI is rolling over, yet the San Francisco Fed’s ‘effective funds proxy rate’ suggests the true tightness (rates plus QT) is at its highest since 2000, while household, government, and revolving debt are at records—raising recession and consumer stress risks.
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Notable Quotes
“The number of private unicorns briefly exceeded the number of public tech companies over a billion dollars.”
— Bill Gurley
“Underperforming companies that were valued over a billion dollars are dead on arrival until you get to a market-clearing price.”
— Brad Gerstner
“Any tech venture investor who compares their fund’s return to the S&P is being naive or disingenuous. The correct index to compare to is the QQQ.”
— Brad Gerstner (quoting and discussing Gokul Rajaram’s tweet)
“The venture capital markets have stabilized for funding new companies, but we’re going to have a one- to two-year period of distress for all those bubble companies.”
— David Sacks
“If you strip the peak years out of a 40-year assessment, venture is actually not that interesting an asset class.”
— Bill Gurley
Questions Answered in This Episode
How should founders of 2020–2021 ‘unicorns’ think strategically about choosing between a recap, a down-round IPO, or a sale in this environment?
The episode brings Bill Gurley and Brad Gerstner together with the All-In crew to dissect today’s venture landscape, from Series A dynamics to late-stage distress and the reopening IPO window. ...
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Given LP denominator problems and over-allocation to illiquid assets, how will the LP mix (endowments vs. pensions vs. sovereign wealth funds) reshape which VC firms survive and thrive?
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For a new fund manager today, what is the optimal deployment pace and fund size to balance performance potential against franchise risk?
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How can startup CEOs practically transition from ‘growth at all costs’ cultures to disciplined, efficient execution without losing ambition or morale?
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If liquid tech indices like QQQ keep outperforming, what structural changes—if any—should be made to the venture model to remain a justified asset class?
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Transcript Preview
I'm recording, yeah. How's my hair, Nick? Do I look ridiculous? I shoulda wore a hat.
(laughs)
Oh, my God. I went to the (beep) teaching salon in (beep) for a haircut a few days ago.
The teaching salon?
Ten dollars.
You got ten dollars worth of value.
(laughs)
Dude, my neck was literally bleeding. The guy cut my neck, like six places.
(laughs)
(laughs)
It's diagonal on the back. 2021.
(laughs)
(laughs) Oh, get off me.
A- a- and he was stoned the whole time. I walk in, he's like, "What do you want?" I'm like, "I booked this thing." He's like, "Shit. Okay, sit down."
He spit out my coffee. (laughs)
(laughs)
I thought, I thought I was, like, in a barber shop candid camera thing.
Why would you possibly do that?
(laughs)
There was nothing available. I told my wife, I'm like, "Get me any hair appointment, anything. I just gotta get my hair cut. It was so long." And then she's like, "Oh, I got you an appointment at the (beep) teaching school." Oh, I'm like, "That's high-end. All the hair salon stylists go there. Must be awesome."
(laughs)
This guy fucking butchered me.
Guy's worth over 100 million, he got a ten-dollar haircut.
Fucking ten dollars. And then he's like, "What would you like to tip?"
(laughs)
(laughs)
I'm like, "Here's a tip, here's a tip."
"Here's a tip, get a new career." (laughs)
You shouldn't be a fucking barber. Yeah, yeah.
(laughs)
I'm going all in.
Don't let your winner slide.
Rain Man David Satterfield.
I'm going all in.
And I said-
We open sourced it to the fans and they've just gone crazy with it. Love you, West Side Queen of Quinoa.
I'm going all in.
All right, everybody. Welcome back to the All In podcast, episode 141. Chamath Palihapitiya has gone missing somewhere in the Mediterranean. We've sent some search crews out. We got some beacons. We're trying to find him, but he is not here today. There will be no conspicuous consumption or discussion of truffle season or wine. But instead we went to the BG squared, if you got to come to All In Summit 2022. One of the highlights of the event was having two BGs, Brad Gerstner and Bill Gurley on the pod. So we thought for All Star Summer, we would bring in some all stars here. Welcome back to the pod, fifth bestie, Brad Gerstner and Bill Gurley. How are you, sir?
I'm doing great. Thanks for having me on.
Bill, you, you don't do a lot of press. You don't do a lot of pods. And, uh, I know you're on a lot of boards, but you're not part of Benchmark's next fund. So people are wondering, are you retiring? What are you up to? I know you're still got all these boards you're on, but w- what's Bill Gurley up to these days?
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