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Re:My Sixth Year as a Bootstrapped Founder by sirspacey on Friday February 16, 2024 @06:47PM (#39404585)
Great advice here!

The math on multiple needs a revision for 2024. SalesForce and Atlassian are valued at 6x and growing faster than ever with over $1B in revenue. No one else is getting a better multiple than that in SaaS right now without a very eager buyer.

Enterprise Value is great in theory. In practice once you get to enough free cash flow you are really just making the decision on whether to take X years of profits in advance for selling all future profits.

Even at 2x-3x, it comes out to “I’ve made enough money/I’m tired, I’m gonna cash out and pay a big tax bill.”

I’d rather make a business that is run by the team and stay with it.

Re:My Sixth Year as a Bootstrapped Founder by matchagaucho on Friday February 16, 2024 @08:34PM (#39405423)
QSBS equity ownership is common amongst US bootstrapped businesses; which can change the tax concerns upon sale.