I sold my company five years ago and have built a net worth of ~$10 million, but compared to my friends I feel like a loser and still keep trying hard at startups that stress me out and make me miserable. What should I do?

echojason@gmail.com'

JASON LEMKIN

It’s crazy, but … you’re not alone.  And sometimes it almost never ends.

  • Dave Duffield made $10 billion when Oracle took over Peoplesoft … but he still had to go and co-found Workday.
  • David Sacks made tens of millions at PayPal but had to do more.  And made 10x more on Yammer.  And now is doing Zenefits.
  • Elon Musk made nine figures and still plowed it all into Tesla, SpaceX, and SolarCity.

And those are among the Top 100 Entrepreneurs of All Time.

Now they aren’t you, and we all do it for different reasons.  For some, it really is about continuing on the journey and “building things”.

But often under that … there’s still a chip.  Even if it’s not on the shoulder.  To do something even bigger.  Even better.  Even more enduring.  To be at the dinner table when Obama comes to town to meet with “tech CEOs”.  Whatever it is.

I’ve still got it myself, although time has diluted it a bit.

And not everyone has this drive.  There are plenty of “one and done” founders.  More than you’d think.  Just happy to have had a real win or even two.  That should be enough.  But for a lot of us … it somehow isn’t.

Ok so what do you do?  I think you have 3 options:

1.  Add value back.  Some of the most highly regarded entrepreneurs are not necessarily the wealthiest.  They’ve added value back as angels, as connectors, as thought leaders.

2.  Move.  Seriously, move outside of Silicon Valley.  It sounds like you have kids, so that will be tough for you, but it works wonders.  Get out of here and it will feel so, so, so different.

3.  Do it Again.  You know a lot.  You know how to build a successful start-up and get richer, more successful, more everything.  But … how badly do you want it this time?

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Published on November 18, 2015
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