Sunset at DoubleM Systems (, Del Mar, California

Saturday, November 21, 2020

First Time Founder Lessons

Lesson #1: Listen to users to resuscitate revenue that's flat-lined.
"A lot of people that design products are in the mindset of, 'I will magically imagine some perfect product and I will pass it down as a gift to my users.' But that’s very rare. It’s usually the other way around — existing users talk about what they wish brands would do, but that feedback isn’t incorporated into the product design."

Lesson #2: You're going to screw up key hires — it's all about how you course correct. “One of my biggest mistakes as a first-time founder was executive hiring. It took us awhile to realize that the most important thing was that we needed to hire people who had already done exactly what we needed them to do — not a similar thing on a different scale."

Lesson #3: When it comes to advisors, bring more on and dedicate more time with them. “A lot of people don’t structure their advisors correctly. Most of the time you have coffee with them once, you tell them what you’re up to, they tell you what they did, and then you maybe talk to them once or twice again – that’s it. I would meet with my advisors for maybe 20 hours a week on average for a year — maybe even more in some cases. Our target was three advisors per major function."

Lesson #4: Proactively manage burnout for yourself and your team. "One of the biggest risks to company performance is founder burnout. It’s the CEO’s job to present and communicate in a certain way our commitment and focus and excitement. If that’s not lined up, there’s going to be a lot of ripples, and it can be dangerous."

Lesson #5: Spot long-term problems, make unpopular calls, and stick to your guns. "If we’re going to go under, it wasn’t going to be because I didn’t do what I thought we needed to. Or I didn’t do what I thought was right because it was too hard or other people might not have liked it."