Your Family May Never Understand - The Entrepreneurial Way with A.I.


Sunday, December 4, 2022

Your Family May Never Understand


So as the years have gone by, we’ve all begun to understand SaaS a lot better.

So many of the leaders in SaaS have now crossed $1B in ARR, from Box to Cloudflare to Okta, and so many more are coming up on it fast, from Smartsheet to Monday to Asana and more.

So we know.  And what we know now for sure, that we always still knew anyway, is that it both (x) takes 7-10 years to Go Big in SaaS, (y) and it probably takes 12-20 years to build something iconic.

To go long.

And … asking your family to be 100% on that journey is asking too much.

I remember an old mentor of mine told me when I started by first startup that “you can only expect true understanding from your family and significant other for about 6 months.”  After that, it was just asking too much to ask them to understand everything you’ll go through.  From the near-death startup experiences, to hiring the wrong VP of Sales that spends all the money, to losing your top customer to a top competitor.

It’s too much, and too hard, for non-founders to understand.

A few thoughts:

  • You’ll never have true work-life balance if you go big.  It just is what it is.  You need to find a way to be present, to be there.  But running a startup tends to consume at least 80% of your mental bandwidth.
  • Expecting your significant other / spouse / etc. to truly understand is asking too much.  In the beginning again, this can work.  But few will understand why it … never ends.  Why you are thinking about work on Saturday, on Sunday morning, and on Wednesday night.
  • You family and friends may not understand the difference between Good and Great.  Why you can’t just work 10% less hard.  Why it’s such a big deal if you lose that huge partnership.  Aren’t you doing just fine as is, they will think.
  • Truly to find a peer CEO group, a good one.  This really helps a lot.  It has to be a group not too far from where you are in ARR and growth, or you don’t have quite enough in common.  Try to find a good one.
  • Get 1 or 2 great mentors.  They are worth more than 100 mediocre advisors and consultants.  1 or 2 folks that can call bulls**t on you.  That have really done it.  And that will push you … to go harder.  To get up that hill.
  • Your VCs and investors will sort of understand, but it’s not the same.  They will get it, and are actually good to talk to about the journey.  They know how hard it is.  But they aren’t working remotely as hard as you are.

It’s tough.  Being a founder is so different.  Everything is so competitive.  Capital is so scarce in the early days, and sometimes, forever.  It takes longer than you think.  People leave.  Folks stop believing.  You can’t stop.  You can’t take a sabbatical.

Your family won’t get it, not really, not usually.  And certainly, they can’t live all of it with your forever.

Get a great peer group, a great mentor, and … adjust.  And understand, in some cases, your relationships will never be quite the same.  It’s a tough but real part of the journey.

If it were easy, it would have been done already.

(Why Are You Doing This image from here)

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Jason Lemkin, Khareem Sudlow