Sold My Company, Now What?

Entrepreneurs

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I recently sold my business. Terms were good. Roughly 3x annual revenue. Not enough to make me rich, but enough to give me a cushion for a while and figure out what I want to do next. I’ve given myself some time to relax and decompress, but I don’t want to coast and burn through too much of that sweet cash.

Now everyone I know keeps asking: what’s next?

This question has honestly been really tough. It’s caused me a fair bit of anxiety.

For a while I was thinking that I had to come up with some big new idea. But as I’ve listened to a number of other serial entrepreneurs, creatives, and investors, I’ve decided that the better idea is to set myself up with a series of experiments. The idea being that it’s better to make lots of little bets rather than take a single big swing.

Here’s what I’m thinking for right now:

I took a full-time job as a Director of Marketing for about 4 months. That didn’t work out, but I’d be open to doing that again. The work was great, but the culture was not a good fit. At the right company I think I could be a great contributor, but it probably wouldn’t last more than a couple of years. A number of friends have expressed interest in doing some investing together. We could probably pool a pretty decent angel fund of about $2M

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