Asked some very successful founders of the past few years what they wished someone had told them. Answer: don't dilute so much in early rounds.
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There's obvious survivorship bias here, but on the other hand there's something worth listening to--early stage valuations have gotten so high that it's easy to raise a lot of money without thinking about how much you need it.
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If you let your seed round creep up to 25-30% dilution, and your A round get to 20-25%, and your B round get to 20%, and throw in an accelerator or a pre-seed round, at some point you will look at it all and say "huh, I wish I had been more disciplined".
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Hold on to ownership as much as you can, except when it comes to being generous with employees. Those percentage points will hopefully be worth a lot some day!
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Subjectively, it feels like companies today dilute about 2x as much to get to the relative level of progress as companies from 10 years ago.
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Replying to @sama
Planning to pretty much avoid dilution like the plague. Stock is for the people who are actually doing it
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If it’s successful the company is a decade+ project. Take time early to get cap table/incentive structure aligned. bootstrap yourself into the future when you are nice and tiny One of my fav of essays: http://www.paulgraham.com/startupideas.html … “Live in the future and build what’s missing”
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