Entrepreneur

So, you made your ‘f*** you’ money. What’s next?

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As exits have been flowing nicely again the past few years, many of the entrepreneurs I work with have experienced their first big exit.

I refer to this moment as when you find that you have life changing money in your bank account, which I like to call “fuck you money.” You now can do whatever you want with the rest of your life.

I was on a walk with an entrepreneur recently who was wrestling with this when we ran into another entrepreneur I had backed who had an exit a while ago and had wrestled with the question of “what’s next.” We chatted briefly and then he hopped on his bike and continued his ride.

Later in the day, I got the following magnificent note in my inbox from my bike-riding, successful friend.

I was thinking about the ‘what’s next’ conversation. I’m sure you’ve seen everything and are all over it, but in my more limited experience, for some people it’s harder than the what’s first conversation (i.e., should I start a company or not?).

I find, unfortunately, that a reasonable percentage of people chase their tail endlessly looking for the next big win, but they can never catch it because they have no idea what they are chasing. Their life spirals inward as they get more unsure of themselves, more frustrated, more unhappy.

I think this state of uncertainty and self doubt causes more depression, divorce and addiction for some people than starting and running a company. Especially if they’ve never felt failure before. Now they fail all the time and they can’t figure it out.

I think it’s mostly because they never find passion again, or they look for it in the wrong places. There are a million things they can do in the world, but the spend most of their time looking for the next great technology company that sells a better widget but doesn’t necessarily change their life in any meaningful way.

They have grand opportunity because they are unbound to do something they truly love. If you love mentoring, mentor, if you love the environment, help it. If you love children, teach them. If you love your family, share with them. Give back to everyone who gave to you on the path to success, and then give more broadly to everyone who seems deserving.

To me, that’s the real grand victory.

Totally brilliant. And so simple.

I had my first exit when I sold my first company (Feld Technologies) at age 28. After the dust settled and I had sold all the stock I’d received, I’d made somewhere between $1 million and $2 million after tax.

When my wife, Amy, and I talked about “what’s next” when I was 29.5 (about the time I finished working for the company that bought mine), one of the options for consideration was to retire and move to Homer, Alaska.

I was making plenty of money consulting, and, while I was investing much of the money I made from the sale into new companies as an angel investor, the idea of living in Homer was attractive. We figured we could easily live for the rest of our life on consulting income and what we’d managed to save, even if none of the angel investments I was making turned into anything.

When one of them was acquired a few months later and we had another $1 million after tax, we realized that we could easily live on $40,000 per year of cash in Homer, which would last us about 25 years if we made no other income.

We were deeply in the “should we just call it quits and go live a different life conversation.” But at almost 30, I just didn’t feel done, and in many ways I felt that I was just at the beginning of a new journey (which turned out to be true.)

So we packed up, moved from Boston to Boulder, and decided to build a life in Colorado while I continued to invest. This was 1995, and the path from there has been powerful and dramatic.

By 1999, I had to ponder “what’s next” again after a number of my angel investments returned more money to me than I ever thought I’d have, and then again in 2002 after getting massively crushed by the collapse of the Internet bubble and losing even more money on paper than I expected I’d make cumulatively in my lifetime.

I’ve been through the “what’s next” discussion with Amy several times, including in 2004 when I doubled down on Mobius Venture Capital (instead of packing it up and calling it quits), in 2006 when we decided to start Techstars and Foundry Group, and again in 2013 after spending six months being extremely depressed.

Each time, I’m adjusted how I spend my life in the way my friend talks about in his final paragraph:

They have grand opportunity because they are unbound to do something they truly love. If you love mentoring, mentor, if you love the environment, help it. If you love children, teach them. If you love your family, share with them. Give back to everyone who gave to you on the path to success, and then give more broadly to everyone who seems deserving.

If you’ve recently had some success, as you go into the weekend, take some time out to ponder how you are you thinking about this. And share if you have any insights!

The post After Your First Big Success, What’s Next? appeared first on Feld Thoughts.

This story originally appeared on Brad Feld.


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