I got a pretty crazy call from a founder friend... “I got an offer for $100M to buy my company and I’m taking it.” Let’s grab a drink. I need to hear the story. I’ll give you the details so you’re on the inside but keeping the company name anonymous. So, he raised ~$25M of venture, 2 co-founders, business is 9 years old. Owns 6% of the business after all the VC dilution. Had an M&A offer at 20x ARR in 2021. Didn’t take it. Had an M&A offer at 15X ARR in early 2022. Didn’t take it. Got an acquisition offer at 5x ARR for $100M. Ended up taking it. “I turned 30 and was just really burnt out. And truth is, I’ve been building this for 9 years and I didn’t think I could raise my next round at the valuation I wanted ” I mean the guy did start with the best head of hair of out my friend group and now looks as bald as Mr. Clean. After I gave him a quick cheers congratulating on the wire hitting, he got real with me: “I’ll make $6M pre-taxes which is obviously incredible to make that much. But I wonder would of happened if I never raised that funding in 2020”. See, my buddy ran it as a profitable business until 2020 and then swung for the fences. He was making $1.5M/year in profit at the time of the first round. But it gets you thinking…. If you’re making $1.5M/year of free cash-flow, and you grow a conservative 30% year over year… Your outcome is probably better than if your raised venture capital. And it’s definitely less stressful. Less stakeholders, less pressure, more dividends. And my favorite part is without that pressure and with those dividends, you get to live a pretty dope lifestyle. From 2017-2019, I was the CEO of a venture-backed startup. I was earning $75k USD/year living in SF. Could barely afford brunch on that ;). I almost had an opportunity to do a secondary in our Series A, but it all fell through. Being reliant on VC to sign terms sheets isn’t that fun. I like relying more on myself. And my friend who sold his company for $100M… I asked him if he’s going to work at the acquirer: “No, I’m going to go buy some distressed VC-backed assets like someone did to me and not raise a penny of VC and dividend and compound like there is no tomorrow”. Probably a pretty smart idea… -- Follow me @gregisenberg for more startup stories. I don't use ChatGPT to write my X posts, just lots of coffee And follow a few of my other companies if you're into... @boringmarketer - all "boring marketing" ways to grow ur biz @DispatchDesign - design @youneedarobot - AI and productivity @MultipreneurGuy - multipreneurship (making multiple cash flowing companies) @latecheckoutplz - my holding company Have a beautiful day!