E29: Coinbase goes public, direct listings vs. IPOs, unions & more with Bestie Guestie Brad Gerstner
Jason Calacanis (host), Brad Gerstner (guest), David Sacks (host), Chamath Palihapitiya (host), Narrator, Jason Calacanis (host), Chamath Palihapitiya (host), Brad Gerstner (guest), David Friedberg (host), Narrator
In this episode of All-In Podcast, featuring Jason Calacanis and Brad Gerstner, E29: Coinbase goes public, direct listings vs. IPOs, unions & more with Bestie Guestie Brad Gerstner explores coinbase listing, IPO disruption, unions, and failing institutions dissected bluntly The episode centers on Coinbase’s direct listing as a case study in how capital markets are changing, contrasting direct listings, SPACs, and traditional IPOs and their impact on founders, employees, and investors. Brad Gerstner explains how alternative IPO structures like Grab’s SPAC can reduce underpricing, remove unfair lock-ups, and curate better long‑term shareholders. The discussion widens to cover growth vs. value rotations, bubble dynamics in private vs. public tech valuations, and long‑horizon investing behavior. In the back half, the besties debate unions (Amazon and teachers), COVID policy failures, institutional distrust, state‑level “A/B tests,” and populist antitrust proposals, ending with a concrete idea to seed universal investment accounts for every American child.
Coinbase listing, IPO disruption, unions, and failing institutions dissected bluntly
The episode centers on Coinbase’s direct listing as a case study in how capital markets are changing, contrasting direct listings, SPACs, and traditional IPOs and their impact on founders, employees, and investors. Brad Gerstner explains how alternative IPO structures like Grab’s SPAC can reduce underpricing, remove unfair lock-ups, and curate better long‑term shareholders. The discussion widens to cover growth vs. value rotations, bubble dynamics in private vs. public tech valuations, and long‑horizon investing behavior. In the back half, the besties debate unions (Amazon and teachers), COVID policy failures, institutional distrust, state‑level “A/B tests,” and populist antitrust proposals, ending with a concrete idea to seed universal investment accounts for every American child.
Key Takeaways
Direct listings shift power toward existing shareholders but can hurt post-listing morale.
Chamath and Brad argue that in direct listings, the optimal financial move for distributed shareholders is often to sell immediately at the open, which captures peak pricing but tends to lead to a one-way drift down in the stock, potentially demoralizing employees who watch their equity fall.
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Traditional IPO lock-ups are a “regressive tax” on employees and long-term insiders.
Lock-ups prevent employees who built the company from selling while late-arriving crossover funds flip allocations for massive one-day gains; structures like Roblox’s no-lock-up listing and Grab’s broad day‑one employee liquidity show this constraint is unnecessary.
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Re-engineered SPAC/IPO structures can materially improve pricing and long-term cap tables.
Brad claims Grab’s SPAC structure secured roughly 20–30% better pricing than a bank-led IPO by eliminating fees, aligning the sponsor with a long lock-up, and hand‑selecting long‑only public shareholders instead of accepting a random, flip‑heavy book.
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Don’t confuse short-term “smart calls” with long-term investment wisdom.
Brad’s decision to skip 21. ...
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Owning a broad basket of top-tier tech over 5–10 years remains highly asymmetric.
Despite near-term multiple compression and a growth‑to‑value rotation, Brad argues that concentrated exposure to the top quartile of global tech companies (public and late-stage private) remains “unfairly” favorable if you avoid overtrading and let earnings compound.
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Workers increasingly reject legacy unions, but a “Union 2.0” could still be powerful.
The Amazon Alabama vote (roughly 70–30 against unionizing) suggests employees dislike incumbent, dues‑driven, politicized unions, yet Chamath and Friedberg believe a data‑driven, transparent, modern form of collective bargaining around margins and contribution could regain relevance.
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Institutional failures on COVID are accelerating decentralization and skepticism.
The panel criticizes CDC/FDA decisions like the J&J pause and post‑vaccine mask messaging as poor risk assessment and PR, arguing such missteps erode trust, push citizens and businesses to ignore guidelines, and expose how static institutions struggle in a frictionless information environment.
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Notable Quotes
“Lock-ups are one of the most insidious things about the traditional IPO process.”
— Brad Gerstner
“Lockups are kind of a regressive tax on the people that do the work.”
— Chamath Palihapitiya
“The most asymmetric bet maybe in the history of all of investing is having a golden ticket to have access to the best technology companies in the world today.”
— Brad Gerstner
“Once you get vaccinated, there’s no reason to wear a mask… To insist that people wear a mask after they’ve been vaccinated is performatively anti-vax.”
— David Sacks
“We live in a moment where capitalism is absolutely under attack, and I truly believe it’s the greatest potential force for good in the world.”
— Brad Gerstner
Questions Answered in This Episode
How should founders decide between a traditional IPO, a direct listing, and a SPAC given the trade-offs for pricing, employee liquidity, and long-term shareholder base?
The episode centers on Coinbase’s direct listing as a case study in how capital markets are changing, contrasting direct listings, SPACs, and traditional IPOs and their impact on founders, employees, and investors. ...
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What would a modern, data-driven “Union 2.0” look like in tech and logistics, and who is best positioned to build it?
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In an environment of eroding trust in institutions like the CDC and FDA, what mechanisms can rebuild credible authority without reverting to centralized information control?
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How can venture firms and crossover funds structure themselves to hold winners longer without being forced into suboptimal exits by fund cycles and LP pressures?
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What would it take to make an Invest America-style universal ownership account politically and operationally viable at national scale, beyond a philanthropic pilot?
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Transcript Preview
Any word from the dictator or should we just do a-
Yeah.
I don't know, man. I gotta-
I haven't heard from him.
I- I- I cannot spend my whole day sitting on Zoom waiting for Chamath.
Or I could have Brad Gershner come on and sit in for-
Isn't he richer than Chamath?
He is now.
He's got the largest SPAC in the world. Should we do that? Should I just have Brad come on the pod and then-
Oh, my God. Yes.
... and then talk to the court on how Chamath-
We have a new SPAC king. We have a new SPAC king.
Start it now. Get him on. Start it.
Yeah, that's a great idea.
And then Chamath comes in later. Chamath comes in later and he's like, "What the fuck?" We're like, "We replace you with the new SPAC king."
(laughs)
Oh, my God.
Oh, my God. Get him on.
Is this like a- a kidnapping and you guys are gonna take me out and drop me off behind, uh-
(laughs)
(laughs)
... behind the railroad cars? What's going on here?
Uh-
Okay. Here we go.
Good. I'm good.
In three.
How's the gain?
Gain is great.
Good.
<< In three. >>
Two.
<< Game two. >>
Two. One.
I'm going all in. Let your winners ride. Rain man, David Sacks. I'm going all in. And I said, we open sourced it to the fans and they've just gone crazy with it. What's his... Love you guys. Queen of Quinoa. I'm going all in.
Hey, everybody. Hey, everybody. It's another episode of the All In podcast. We took last week off because it was spring break and we all needed a break. Hope you had a great one too. With us today, of course, the Queen of Quinoa, from an undisclosed sunny location, David Friedberg, the Rain Man-
It looks like Redwood City. Is it Redwood City?
(laughs)
... the Rain Man himself, David Sacks, ready for GovernorSacks.com, and of course, the king of all SPACs, Brad Gershner is with us again, the new dictator, uh, filling in for Chamath Palihapitiya, the dictator.
(laughs)
Oh, wait. Chamath Palihapitiya the dictator is here as well, and special bestie guessie-
Jason, Jason, Jason.
(laughs)
(beep) (beep) It's not when you (beep) (beep) .
(laughs)
(laughs)
I don't know what that means, but we're editing that out of the show.
(laughs)
That's a bunch of beeps. Uh, but welcome Brad, sitting in just for a moment here, 'cause Chamath was gonna blow us off. He was pulled away.
Yeah, Chamath was a- he was a no-show. We needed a SPAC king. We needed a new SPAC king.
Sorry, you guys.
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