So startups are just soooo hard, at least until you hit scale.  At least until somewhere between $10m and $30m ARR, depending on the category, competition, and timing.  Sooo hard until you can’t be stopped.  You’re always almost out of money, or at the edge of slowing growth, or just can’t find that critical VP you need, or build that feature in time.  It’s constant latent stress, and in many ways, you’re sort of alone outside of your cofounders and some of the folks on the management team.

We had a great convo with Todd McKinnion, CEO of Okta, where he said until $30m ARR or so, he always felt things were just … fragile:

But as tough as some times were, and even dark as thing seemed in some cases I was never … down.   But never down.  Maybe because there was never time to be down.

No, the only time I’ve been lost is twice — after selling my startups.

The WSJ the other day had a piece on retirement, and the entrepeneur above’s journey really resonated with me.  “Now 78, he found there is only so much golf to play and so many lunches to go to.”

Both times when I sold my startups, I was happy at first.  Finally, a chance to just do nothing.  The first time I went to Laguna Beach and just decompressed.  The second time was different, as I had to stay for 3 years, at least on paper.  I never got that break, but snuck one into Napa.  And we bought a nicer house.

And then both times, after selling, I eventually had time to just do … nothing.  Glorious, no?

Well, no.  Within just a few months, both times, I felt as if I’d slipped into irrelevance.  I remember about 6 months after we sold EchoSign to Adobe, one of my VCs invited me to their CEO event that year.  I felt irrelevant being around them, and in some cases, like they now looked past me.  I wasn’t on the journey with the “real’ CEOs anymore.

Yes, I got into great shape.  Wow, I could bench 245, hooray.  But I was just lost, without a sense of purpose.  I decided at least I could start a little blog, and share some learnings, and do some investing.  In the end, that worked out, and SaaStr and SaaStr Fund have given my real purpose again.  Maybe more than ever.

The point here is just, if times are tough — and I know they are for many — push on.  Because it is probably worth it.  At least, if you really want to do great things.  We only get so many chances. Don’t sacrifice your health, or your family.  But other than that, leave it all on the field.  Don’t hold back. Give it truly 120%.  Don’t let the excuses, often valid ones, hold you back from doing everything you can, and more.

A great startup gives your meaning, a journey, a rasion de’etre.  At least, it has for me, and I think many of us.  It’s why we do it, at least in part.

Maybe it’s more fun to have a yacht, or to ski all year, or to just surf.  Maybe.  For some, it seems like it is.  The MySpace guy.

But if you are a builder, you gotta build.  At least, I know I do.  And yes, it’s hard.  Dustin Moskovitz is still building.  And he co-founded Facebook.  Jyoti Bansal is still building.  Dharmesh Shah is still building.  You probably should keep building, too.

A related post here.


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