10 Things I’d Do Differently as a Founder Next Time

Dear SaaStr: What would you do differently to succeed, if you were to start again?

My top list:

Don’t start a startup if the founders aren’t 100% aligned, especially on how committed you all are. I’ve done this, and it worked out OK, but not even close to as well as when we were all on the same page.

Have a long vesting schedule for the co-founders. This ensures the quitters don’t walk away with too much.

Avoid the Desperation VP Hire. Period. The “Desperation VP” is a key position you have to fill, but have struggled for months and months and don’t have any more strong candidates. You are always better off not making this hire. You hire someone not good enough, they hire a ton of mediocre people, they spend all the money, and in the end, you lose a year.

Be more patient. It’s years 5–10 in a startup when power laws really kick in, and years 10 and beyond when you have a shot at a unicorn. You have to be impatient to get something off the ground, for sure. But you also have to settle in and always think long-term.

Take some secondary liquidity once you are able in the scaling phase. Selling some shares, if you can, helps you go long, be more patient, and more. I should have done this in the past.

Don’t go into business with folks that don’t really want to be in business with you. I made this mistake, and it was a painful one. If one or more of the founders or partners doesn’t really want to work with you, don’t do it.

Don’t let yourself get burnt out. Tired, yes. And sometimes you really do have to work 100 hours a week. But again and again, I’ve let myself get burnt out. You have to get more help.

Find mentors that can help you think (and go) bigger. Sometimes, you just get lost in the day-to-day challenges and how hard it is just to succeed in the market and with the products you already have. A great mentor though can really help you see how you can go bigger.

Remember that Just Staying in the Game doesn’t always make you #1, but it can still lead to an amazing outcome. Everyone wants to be #1, but there are so many great spaces where even #3 has a big exit. If you have happy customers, a good team, and decent growth — just keep going. You will likely be worth even more later. But if you exit the game too early, you give up so much potential upside.

Realize how special a great team truly is. This one took me a while to truly understand. It’s great teams that win. With one great VP, you can do so much better. With two, things start to really hum. If you have 3 great leaders on your team, truly great — then you can do amazing things. If you have 3 or more truly great VPs, and they are a good team together — just backfill them. Help them. And let them run.