All-In PodcastE29: Coinbase goes public, direct listings vs. IPOs, unions & more with Bestie Guestie Brad Gerstner
At a glance
WHAT IT’S REALLY ABOUT
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.
IDEAS WORTH REMEMBERING
5 ideasDirect 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.
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.
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.
Don’t confuse short-term “smart calls” with long-term investment wisdom.
Brad’s decision to skip 21.co and Bitcoin at $1,200 felt brilliant when crypto crashed, but that short-term validation locked him out of a massive secular trend; he frames this as a lesson in mental flexibility and continuing to fund asymmetric opportunities even after early setbacks.
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.
WORDS WORTH SAVING
5 quotesLock-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
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