Investing
Where I'd put money, and where I wouldn't.
I invest my own money in founders, so I live with these views. Every article is dated. If you're asking what enough looks like for you rather than for a buyer, start with the five money stages.
Investments I've made
The bets I put my own money behind, written up when I made them.
- Reddit IPOWhy I'm Buying Reddit's IPO
- Vurvey Labs boardListen Labs Sold for 67x Revenue. Airtable Sold for 2.7x.
- EnergyWhy I Own Tankers and Oil Companies Right Now
- Slack, early investorPreparing for Slack's IPO as an Early Investor
- Multisites.aiAI Agents Are Shopping for Apartments
Working out your own numbers? Try what your company is worth or what you'd take home if you sold.
LatestEssay · Oct 23, 2026
Why California's Poor Will Pay the Billionaire Tax
California's billionaire tax sounds like a bill for a few hundred people. Meta built Mark Zuckerberg a way to pay it without giving up any control, and the cost flows back to everyday Californians through higher prices.
Read it →Latest
Newest first, not yet filed under a topic.
Valuation
What the multiple is paying for, and when the revenue is hollow.
Buying and selling
How the buyers think, and what they do the week after they own you.
- Dec 2, 2025What Private Equity Spreadsheets Leave OutPrivate equity is not inherently evil, it is inherently numerical, and once numbers dominate the worldview…
- Apr 16, 2025What You Actually Take Home When You Sell Your CompanyThe sale price is not what you take home.
- Jul 28, 2020Why I Sold My Slack Stock After It Attacked MicrosoftI sold my Slack stock after its full-page ad aimed at Microsoft.
Where I'd put money
The bets I'd take, and the ones I'd stay out of.
- Oct 23, 2026Own Assets or Be Left BehindElon Musk's $1 billion Skydance investment is the latest example of owners putting their ownership to work.
- Oct 20, 2026How to Spot a Bubble, According to Ray DalioBubbles take years to form and years to burst.
- Oct 19, 2026Why Elon Musk and Anthropic Are Giving Away SharesAI is making the people who own it richer, fast, while people with only a paycheck fall behind.
- Oct 19, 2026What Berkshire's Bending Spoons Bet Says About SoftwareBending Spoons buys software brands cheaply and runs them for profit, and the market values it at about four…
- Oct 18, 2026What Andrew Ross Sorkin's 1929 Teaches AI InvestorsGood leaders in 1929 propped up a market they had doubts about, and they weren't villains.
- Oct 17, 2026What Elon Musk’s Net Worth Teaches About OwnershipYou can start owning businesses without founding one or buying a whole share.
- Oct 17, 2026Is AI Propping Up the US Economy?Business owners using AI well are running with far fewer people.
- Oct 11, 2026Why Even Dividend Stocks Aren't Safe AnymoreA steady payout doesn't protect a business from fast change.
- Oct 8, 2026Where I'd Put Money Instead of the Anthropic IPOWhere I'd put money instead as AI models get cheaper, and why I think the IPO lands after the November…
- Oct 6, 2026Tesla Is Having Its iPhone MomentI think Tesla has passed its tipping point.
- Sep 13, 2026The Industries I Would Avoid Starting in Right NowContent mills and SEO agencies, then generic outsourced back-office work.
- Apr 8, 2026AI Only Picks One WinnerAI does not hand you ten results to compare.
Follow what I'm building and backing
I post on LinkedIn and X about the companies I back and the products I build.
Join 2,219 people following along.