As someone that’s been a founder, an investor, and a student of startups and SaaS for a while now, when I look back at my top mistakes, leaving any relationship broken is high on the list.

Nick Mehta, CEO of Gainsight, put this high on his list of Top 10 Mistakes as well in his look back the other day:

Mistake #6/10: Not parting ways well always

In startups, relationships end. Teammates and clients will leave. It’s tough, but it’s part of the circle of life.

Over the years, I adopted the philosophy that I want to treat people well in all phases of our relationship, aligned to our Purpose “to be living proof that you can win in business, while being Human-First.”

But I can remember two situations (early on) with teammates and two with clients where I didn’t practice what I preach. In the teammate case, I made the folks leaving feel guilty—“How can you do this?” In the clients’ case, I didn’t take it well and burned two relationships in the process.

Lesson: End every relationship in a Human-First way. When a teammate leaves, my only reaction is (1) thank you for what you’ve done here, (2) congratulations on what’s next and (3) what can we learn to continue to get better. When a client leaves, we want to help them on the way out, because they often come back.

One thing I’ve learned in business though over personal life (and in startups, they often have similar dynamics), is it’s often never too late to fix things.  Well, it’s often too late to totally fix things.  But relationships can be repaired in business, up to a certain extent.

Now is a good time to do that.  We’re all now well into the “post-Covid world,” and even now, many of us are seeing folks in person for the first time in 3+ years.  The craziness of 2021, and the rollercoasters of 2022 and 2023 are behind us.

Now is a good time to reach out to folks that you left things on less-than-great terms.  I’ve done a little of this myself.  Sometimes, it’s worked.  Sometimes, it hasn’t.  But I’ve found it’s at least a good time to talk.

This may sound almost silly to say, but some of the best advice I can give to new founders is this: Apologies Are Free.  And in fact, they can be a super power if you are in a position of authority.  And “CEO” is a position of authority, even in a tiny startup.

Most folks can’t bring themselves to apologize, for whatever reason.  Most VPs that get into trouble can’t do it.  Most VCs that screw something up don’t do it.  Most people just don’t apologize.  I honestly don’t know why.

But when someone in a position of authority apologizes earnestly for something, it’s often an almost magical moment.  It just works.

Be a gracious CEO.  The best CEOs are almost always gracious.  Almost every SaaS CEO that has done something amazing is gracious.  Eric Yuan, Stewart Butterfield, Dustin Moskovitz, Therese Tucker, they are all just so .. gracious when you meet them IRL.  Not weak; they are all strong leaders.  But gracious.

And when you screw up as a founder, and we all do, all the time — apologize quickly and earnestly.  It works.

And now, in this post-Covid era, go see if you can fix something.  Pick up the phone, send the email, say you screwed up a bit, or just reference the better times and ask to catch up.  And then sort of apologize.

It’s worth a shot.


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