I’m curious what kind of secondary sale happened? What is normal these days? Is it $5m $10m? Is that excluded from the $50m raised or comes out of that amount. Thanks!
I’d take the money, spend time with family (he mentioned toddler) and then figure out what to do next. Retiring isn’t everyone’s dream but at least having generational wealth is a big relief.
The secondary provided that relief. Continuing to work on the company makes perfect sense if you enjoy it, which he clearly does (with the inescapable ups and downs of every start up of course).
I dunno man. A useful psychological trick in this scenario is to imagine you were on the other side of the transaction.
Say you have nine figures in your account. Would you push it all into this company to be able to have a fun job? Seems completely insane to me.
F You Money means you can spin up whatever projects you want for the rest of your life. Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much?
Speaking as a co-founder CTO, I believe there is a very insidious kind of attachment that forms when you’re dancing with burnout, and working on a successful company that you’ve built from the ground up.
“I want to leave a dent in the universe” I told myself. After 3 months in a hammock decompressing, I very quickly realized that there is more to life than work, and it’s really easy to find fulfillment building things if you get bored. But this viewpoint is really hard to hold onto when you’re buried in the day to day excitement of the job.
I think of an amount like $10m as “retire well, leave some for the next generation” kind of money. $100m is more like, “retire well, leave passive income for N future generations.” That extra 10x is super compelling.
Thanks for your message and point of view. You’re probably the only person here who has been presented with a similar scenario, and this is exactly how I felt.
you can take the money... and then continue to work. Nothing says you have to retire- I would have taken the money and figured out what's next! Not to mention that hopefully you've given shared ownership with your other early employees, who can also then at least have the opportunity for their own liquidity event.
Honestly, I respect the commitment. It's almost certainly a bad decision, but a founder that can turn down a 9 figure exit at the tail end of a tech bubble he's right in the middle of, has a good chance at having the right mindset to build a great company and survive the collapse. There's a good chance he regrets this for the rest of his life, but you can't argue that he wasn't a true believer or is a sellout.
Essentially yes, but with a few additions CSV lacks:
1. Multiple tables in one document (table.users, table.orders)
2. References between tables (:user:42 links to id 42)
3. Object blocks for config/metadata
4. Streaming format (ISONL) for large datasets
The type annotations are optional - they help LLMs understand the schema without inference.
You could think of it as "CSV that knows about relationships" - which is exactly what multi-agent systems need when passing state around.
Tested across Claude, GPT-4, DeepSeek, and Llama 3.
The key finding: LLMs handle tabular formats natively because they've seen billions of markdown tables and CSVs in training.
No special prompting needed.
For associations, I tested with multi-table ISON docs like:
table.users
id name
1 Alice
2 Bob
table.orders
id user_id product
101 :1 Widget
102 :2 Gadget
Prompt: "What did Alice order?"
All models correctly resolved :1 → Alice → Widget without explicit instructions about the reference syntax.
The 30-70% token savings come from removing JSON's structural overhead (braces, quotes, colons, commas) while keeping the same semantic density.
Haven't published formal benchmarks on this yet - that's good feedback. I should.
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