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As a company founder, were there any early hires that almost ruined the company?

I’ve had one or two each time. Try to avoid it!

In my first start-up, I found the Dream COO. He had 20 years of industry experience (vs. me, I had none). The customers loved, loved, loved him. And he had enough of a chip on his shoulder to still do a start-up and change the industry.

We shook hands and I closed him. And then I signed a term sheet to raise $8m in venture capital. All seemed good. Until he changed his mind and stayed where he was. The term sheet was pulled. The key initial customer that loved him got cold feet. I was out of options. And now, with only 2 weeks of cash left in the bank.

Lesson? Even with founder urgency, you can’t always rush key hires. He wasn’t really ready. We needed to spend more time together. And we knew that. We could sense the risk. But it was a start-up, so we took the risk. But we should have just slowed this key hire down.

In my second start-up, I found the Dream Co-Founder. But he also wanted to run another business on the side. And was only willing to commit for a year. But he was the best I knew. 12 months later, he quit and I had almost no money left in the bank and had to figure it out, somehow.

Lesson? Make sure you are 100% aligned with long-term goals with your co-founders. This stuff is just too hard, and takes too long. I was committed for the long haul. The others were amazing, but they weren’t as committed, to varying degrees. That was a mistake.

I then made the same mistake a third time

The meta-lesson? When you find your dream senior hire, that’s great. But also, slow it down. Make sure it’s what they really want. That you are aligned on where they also want to be in 6, 12, and 60 months.

And this is your job — not theirs.

Really, slow down all your 2-3 most critical decisions of the year.  And speed up the rest.

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