The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 9 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Wilkinson: Bootstrapping Flow against Asana cost me $10 million
“And I ended up losing ten million dollars trying to compete with venture-backed businesses and bootstrapping. It was all my own money, poured ten million dollars, lit it on fire, trying to compete with Asana because I didn't understand how the business world w…”
Wilkinson lost billionaire status following decline in Tiny’s stock price
“At one point being worth over a billion dollars, by the way, should redo the title of the book from barista to billionaire. Now it's former billionaire because our stock went down”
Wilkinson: Taking an SSRI improved my mental state more than wealth
“No amount of money or success or attention or anything else had done what this little tiny yellow pill could do for my mental state. And so now I've been on an SSRI for four and a half years or something like that.”
Wilkinson: Pivoting to SF startups yielded 5x higher rates for web design
“Like when I started my web design firm, I started mostly with local and small projects, but very quickly I found a job board in San Francisco where startups would share projects they needed help with. I could charge five times the amount for five times less wo…”
Tiny leaves acquired companies alone unless the founder chooses to depart
“When tiny buys a company, we generally just leave them alone. If they already have management in place, we say nothing changes. You know, no one should know that any, that we've even bought them. Obviously people know that, but really like there should be no c…”
Wilkinson: Tiny owns Letterboxd, the largest social network for film lovers
“We own Letterboxd, which is the largest social network for film lovers.”
Wilkinson: Automated AI Agent Researches Meeting Attendees via Perplexity
“It looks on my calendar, 30 minutes before I meet anyone. It goes on to perplexity and it does a deep dive on the person and it sends me, it goes into my email and it gets the context of the meeting.”
Wilkinson: Over 90% of my money goes to a philanthropic foundation
“He said, you know, I've reframed it so that all my money, 90% of my money plus goes into my philanthropic foundation and then it gets given away to great causes. So when I think about working really hard or losing a deal or a investment going well. The win isn…”