I think when we sold each of my startups, the offers were hard to resist — but for different reasons.

The first time, it was just 12 months from founding, and we’d closed $6m in contracts our first year, and had an amazing team. But while that all sounds incredible … structurally, we had huge challenges. We’d need pseudo-FDA approval (not direct, but indirect). We’d need to build a $50m+ plant that we had zero domain expertise in building. We’d need to plan for an 8–10 year development cycle. We were doing something that actually might in fact be impossible from a technology standpoint (it still wasn’t 100% clear). The future was exciting, but incredibly challenging and way beyond the skillset of the team. Way beyond.

12 months after founding, our competitor came to us and offered $50m in total. The number wasn’t a coincidence. They’d gotten our Certificate of Incorporation, figured out the valuation of our investment round, and offered an all-in price of 5x what the investors paid 12 months before.

And they told both the founders we didn’t have to stay if we didn’t want to. (I only had to stay 20 days).

And they said — go shop it. Take 60 days. Find a better price. And if we found a better offer, they said they would beat it.

At the time (2004), that place … it was an offer that was hard to resist. As they’d addressed all the objections.

We sold for $50m after 12.5 months, no regrets, never looked back, and both of us went on to co-found other successful startups next.

The second time, it was different. The price was higher, the dilution lower. But this time, it was 5 years in, not 12.5 months. So much more time in, and further along.

The offer wasn’t hard to resist operationally, in that we were crossing $10m in ARR, growing 100% and cash-flow positive.

Zero need to sell.

But the team was tired, it was 5 years in, and the price was an order of magnitude more capital than we’d raised.

It was an offer you could refuse. We had 2 offers, in fact. If you’re cash-flow positive and growing nicely, there is zero need to sell. But it was an offer that was hard to refuse intellectually. If we said No, I had to sign up without a real co-founder for 10 more years. I had a great management team, and unlike last time, I had a team that could truly execute. But I didn’t have a true co-founder this time. That was hard.

Emotionally, it was easy to refuse. We’d be twice as big, twice as strong, in 12 more months.

But intellectually, it made sense.

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