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Re:Ask HN: I'm a solo founder and a billion dollar company w... by m_ke on Friday September 17, 2021 @11:38PM (#28573446)
We are also bootstrapped and wasted years chasing after a few large contracts like that. Sales process usually ended up taking 6-18 months, integration another 12, customer support some more, new custom feature development 80% of our dev time. By the time things were deployed half of the people we were dealing with were on to new jobs, companies were acquired, offices closed, funding rounds fell through causing them to shut down before paying us.

If it will help you get by I'd advise you to charge 4-10x more than you think is right and make them pay yearly up front, and don't count on future revenue.

Re:Ask HN: I'm a solo founder and a billion dollar company w... by singleauroa on Friday September 17, 2021 @11:46PM (#28573493)
Thx for the advice! Yes the next question is how do I actually price them?! I have no experience in enterprise pricing/sales. Since they are a m-b$ company and even actively mentioned they have a large budget for this because they really want it... what can I expect? This all feels like starting over in elementary school for me, haha.
Re:Ask HN: I'm a solo founder and a billion dollar company w... by m_ke on Saturday September 18, 2021 @12:03AM (#28573591)
At least 2x what it would cost you to have people work on it full time for a year.
Re:Ask HN: I'm a solo founder and a billion dollar company w... by bb88 on Saturday September 18, 2021 @02:24AM (#28574160)
If it's a contract, 3X is the terms I'd go with.