Dear SaaStr: Does a Big Exit Make You Happy?

Well here in the SF Bay Area … we live in a strange place.

Folks I know with “infinite” money sort of fall into 3 buckets:

Category 1:  Still Building Stuff.  For Whatever Reason.  In their DNA.

This is who they are.  Oftentimes, they aren’t really happy.  But they thrive here.  Elon Musk could hand off the reins now, couldn’t he?  Zuck could give the keys to Sheryl Sandberg and things would be A-OK at Facebook, I’m pretty sure of that.

Jyoti Bansal sells AppDynamics for $3 Billion+ to Cisco.  And then?  Right back at it with Harness and more.  His learnings here:

Category 2:  Retired and Content.

I don’t understand these folks, but they seem happy racing their Porsches, going to Necker Island for the umpteenth time, upgrading the house at the Yellowstone Club, etc.  Sort of doing a non-profit, but not full-time.  Living the dream.  More power to them!!

In all seriousness, they often find more enjoyment in their family and other pursuits than work in this case.  That makes more sense to me.  Start-ups are 24x7x365, at least in terms of mind share.  You do miss out on a huge number of life experiences when you do them.  Steve Jobs lamented how much it took out of him.  If you can just step out at the right time and enjoy the rest of your life, I’m in awe.

Category 3:  Retired and Quietly … Sad.

The thing is, I know this sounds awful and crazy … but there are only so many things to buy.  Once you’ve bought them all … what’s the point?  How many cars do you need?  Is a 20,000 sq ft home really so great once it’s built?  Flying private is special if you have to fly … but once you’ve flown everywhere, where do you go?  A bigger yacht?  Seriously?  I think these folks face their mortality.  If money is it for you, and you have an “infinite amount” … what’s the point?

For me, the learning is the most impactful money is Enough to Not Have to Work for the Man again.

That’s worth striving for.


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