Dear SaaStr: What’s Your Recommendation for Vacations for a Founder CEO of a Tech Startup?

Always take them.

When I look back at the many mistakes I made as a 2x founder, both times with some degree of success in the end … and there were so many … one thing I am 100% glad I did was take vacations.

And I mean — normal, full vacations.  

By that, I mean, a full week. In a normal place. And I only checked email once a day, once I had real VPs in place (before that, when I was the VPs, I still had to be on email all the time).

But — it can be tough to take any time off until you have a strong management team, at least a partial one. In the early days at Adobe Sign / EchoSign, I did the customer support shift from 11am-6am. That’s an anti-vacation, let me tell you.

Once you have a team you can trust, take the time off. You need it. And they will do fine.  In fact, I’ve fallen a bit off track here lately myself, and suffered a bit for me.  If you truly have a strong team, you often in fact find them perform even better when you’re out for a vacation.  A weak team?  Nothing gets done when you are gone.

A deeper dive and related post here:


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