Back in the saddle
1. Key Themes
CEO "Side Projects" Are Now a Structural Feature of Big Tech Governance
The trend of sitting CEOs founding fully resourced parallel companies has moved from exception to expectation among Silicon Valley's elite.
"Vlad Tenev, Brian Chesky, Brian Armstrong, Daniel Ek, etc. others are all now doing fully capitalized, fully staffed companies as side projects. The extreme of course is Elon and Sama."
"These aren't merely hobbies - these guys are founding and funding companies that presumably take up significant amounts of finite and highly valuable time, attention, and energy."
Dual-Class Share Structures Make CEO Accountability Effectively Impossible
Governance reform is structurally blocked at the most successful companies, making board oversight of CEO behavior largely ceremonial.
"The first, most obvious answer is dual class shares. You literally can't stop them. Boards and shareholders are largely passive advisors."
The "Hidden Cost" Economy: Young Adults Are Buying Back What Prior Generations Got for Free
Standard economic metrics obscure a generational wealth gap driven by the liquidation of social capital — a framework with implications for housing, consumer sentiment, and political risk.
"Instead, the young must now buy back, item by item and at retail prices, what their grandparents received as a bounty of prior civilizational investments... Price indexes measure the individual cost of discrete goods, but they are not intended to convey the total cost of personally repurchasing a destroyed commons."
Rechtman adds his personal synthesis: "Housing Theory of Everything: if housing were more abundant, we would all feel a lot richer."
Passive Capital Flows Are Beginning to Distort Private Markets the Same Way They Did Public Small-Caps
The structural dynamics crushing SMID-cap public equities are migrating into private markets, threatening the capital availability for all but the largest names.
"Zip makes the case that the same recursive capital flows/forces buffeting smid cap stocks are coming (here) for private markets too. Good case for companies to be reorienting their long term ambitions toward buybacks and manufactured liquidity vs binary of illiquid or public. If money just naturally flows to the biggest names (passive investing), there is no capital to support anything but."
2. Contrarian Perspectives
CEO side projects can be bullish for shareholders — depending on whether the CEO is truly essential
The consensus view is that a distracted CEO is bad for shareholders. Rechtman flips this: it depends entirely on whether the CEO is mission-critical or not.
"The all star CEO who is 100% essential to the success of the firm is being retained to work at a higher level of abstraction. Bullish! The mid or inessential CEO is preventing someone more locked in from taking the seat. Bearish!"
His underlying logic: the best CEOs will inevitably outgrow a single company's scope, and trying to contain them risks losing them entirely.
"After all, if the job of a CEO becomes largely vision, the best people will eventually operate at a level of abstraction such that one company (or one business in the case of 2010s web/app companies) can't contain and absorb all their vision."
The standard economic case that young adults are "doing fine" is a measurement failure, not a factual finding
Against the consensus that real incomes and purchasing power have risen, Rechtman argues the data misses the destruction of non-market goods — trust, public infrastructure, courtship culture — that previous generations inherited for free.
"On the surface it does seem as if the young are fine. Real median incomes are higher than they were for their parents at the same age... And yet this generation is also not marrying, not buying homes, not having children, and seem pretty miserable. I think we're clearly in the midst of a tremendous measurement failure."
Mass surveillance can be a substitute for police presence — and may reduce harm, not just enable it
Rechtman, self-identified as "left libertarian" and an ACLU member, nonetheless argues surveillance tools may reduce dangerous police-civilian encounters.
"Surveillance can take the place of cops on the street, which spares more chance encounters that can go wrong."
3. Companies Identified
| Company | Description | Why Mentioned | Quote |
|---|---|---|---|
| Airbnb | Public travel/hospitality platform | CEO Brian Chesky allegedly posted about an RWA (real-world asset) side project; later claimed he was hacked | "No one batted an eye that Chesky might have been announcing an RWA project with a slop post because every enterprising CEO needs to be founding more/new/multiple companies." |
| Robinhood | Retail brokerage platform | CEO Vlad Tenev cited as example of CEO running parallel side projects | "Vlad Tenev, Brian Chesky, Brian Armstrong, Daniel Ek, etc. others are all now doing fully capitalized, fully staffed companies as side projects." |
| Coinbase | Crypto exchange | CEO Brian Armstrong cited in same pattern | Same as above |
| Spotify | Music/audio streaming | CEO Daniel Ek cited in same pattern | Same as above |
| Google / Meta / Amazon | Big Tech platforms | Cited as early architects of the "internal side project" culture that normalized the behavior | "Some companies are just better suited to capture side projects internally (Google, FB, Amazon, etc). And now that those businesses have created the culture, everyone wants the status marker of a longevity or AI project." |
| Zip | Procurement software company | Referenced for its analysis of passive capital flow risk migrating from public to private markets | "Zip makes the case that the same recursive capital flows/forces buffeting smid cap stocks are coming (here) for private markets too." |
| Slow Ventures | Early-stage VC fund (~$325M) | Rechtman's firm; mentioned in context of new associate hires and career advice | "We have 2 new associates joining Slow this week." |
4. People Identified
| Person | Description | Why Mentioned | Quote |
|---|---|---|---|
| Brian Chesky | CEO, Airbnb | Allegedly posted about an RWA crypto side project (later claimed hacked); used as leading example of CEO side project trend | "No one batted an eye that Chesky might have been announcing an RWA project with a slop post because every enterprising CEO needs to be founding more/new/multiple companies." |
| Vlad Tenev | CEO, Robinhood | Named as part of the CEO side project cohort | "Vlad Tenev, Brian Chesky, Brian Armstrong, Daniel Ek, etc. others are all now doing fully capitalized, fully staffed companies as side projects." |
| Brian Armstrong | CEO, Coinbase | Named as part of the CEO side project cohort | Same as above |
| Daniel Ek | CEO, Spotify | Named as part of the CEO side project cohort | Same as above |
| Elon Musk | CEO, Tesla/SpaceX/xAI/etc. | Cited as the extreme end of the CEO multi-company model | "The extreme of course is Elon and Sama." |
| Sam Altman ("Sama") | CEO, OpenAI | Cited alongside Musk as the most extreme example of multi-company CEO leadership | Same as above |
| Kathy Hochul | Governor of New York | Appeared on Odd Lots; Rechtman expresses cautious bullishness on her economic agenda | "The ambition around economic development, nuclear power generation, and housing are genuinely exciting. Bullish Albany?" |
| Yoni Rechtman | Partner, Slow Ventures; author | Generalist pre/seed investor; newsletter author | "I'm a partner at Slow Ventures, where I lead pre/seed rounds from a ≈$325M fund." |
5. Operating Insights
Early-career positioning: be the person who does what no one else can or wants to do
Rechtman's most durable career advice, validated over five years, is a simple two-option heuristic for how to become indispensable quickly.
"You should always strive to do the work either 1) no one else can do or 2) no one else wants to do."
This is particularly actionable for early employees at startups, where role definition is fluid and differentiation is often earned through willingness rather than seniority.
Private company capital strategy needs to evolve: buybacks and manufactured liquidity may replace the IPO binary
For operators of private companies, the passive capital concentration trend is a direct threat to future fundraising optionality. Rechtman flags an emerging alternative playbook.
"Good case for companies to be reorienting their long term ambitions toward buybacks and manufactured liquidity vs binary of illiquid or public. If money just naturally flows to the biggest names (passive investing), there is no capital to support anything but."
6. Overlooked Insights
Ukraine's wartime resource allocation via market mechanisms is a live experiment in institutional design under extreme pressure
Mentioned only as a one-line link, but the concept — using price signals and market structures to allocate military resources — is a genuinely novel governance case study with implications for crisis management, government contracting, and institutional reform.
"How Ukraine Built a War Fighting State. Crazy anecdotes about using market mechanisms to allocate wartime resources within the military."
Silicon Valley's CEO side projects serve a social signaling function that directly substitutes for elite philanthropy on the East Coast
This is framed almost as a throwaway observation, but it reveals something structurally important about how status and identity work in tech — and why boards are unlikely to push back regardless of fiduciary arguments.
"SV doesn't really do philanthropy and the arts in the way Wall Street does so this takes the place of say joining the board of the Met."