This is such a great post for so many reasons, but I'm glad Lenny made that chart in particular. The overnight success fantasy is toxic and I've seen it infect (and sometimes ruin) many startups.
- The equity split is about incentivizing/rewarding you both for the work ahead, which is going to be much harder than anything thus far
- I would treat the 2 years as a sunk cost
- If you are true cofounders, 50/50 or 51/49 is the fair way to go
- Vesting diffuses the edge cases (either of you leave early, either of you turn out to be flakes), and is a necessity if you want to ever raise VC money
- It sounds like there is a question of him working only part time. In this case he should not get founder equity. Read the clerky docs as there can be severe drawbacks of granting significant amounts of equity post-founding
Pretty good overview from the investor side. I find it's a helpful forcing function to be disciplined about retrospecting regularly – it's as much for the benefit of the investors, as you the CEO.
I hope startup founders read this and internalize it. Those who raised at 100x multiples and think "this will not happen to me" might be for a rude awakening a year from now.
Thank you for sharing! Fun to read a story of someone sticking around for so long and not jumping ship frequently. Curious, as an early engineer, what were some things that Sumo Logic did really well that made you want to stay there beyond four years?