What Successful Second-Time Founders Do Differently

Here’s what serial entrepreneurs change about their next business

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The sun was setting and starting to melt into a creamy orange color over the beautiful fields of Mallorca’s nature. Our group of 15 entrepreneurs had gathered on the island to learn from each other. One of my core beliefs is that if you surround yourself with extraordinary people, good things happen, and you’ll learn a lot. That’s why I host Digital Founders Camps to share my own entrepreneurial experiences with the next generation as well as to learn from them.

Illustration: Ariane Frida Sofie

Our special guest for the evening was Jordi Ber, a local entrepreneur from Mallorca. It turned out that Ber and I had a pretty similar history. We both founded startup companies around 10 years ago. Both companies shared the mission to help small and medium businesses online. Ber ran Habitissimo, a marketplace for tradespeople, and I founded RegioHelden, a marketing agency for local businesses. We both had employed hundreds of employees and sold our companies in deals that made us financially independent.

While we raised our bottles of San Miguel beer to cheer to Ber, who had personally exited his company just a couple of weeks before, a question arose from the group: “What would you do differently the next time?”

I believe the entrepreneurial journey of lifelong learning never ends. Despite all the things that went well, both Ber and I had thought about what we would do differently in the future. While we ate the delicious food and the Spanish beer kept flowing, we put together a list of the things we think second-time founders do differently than first-time founders.

Drop trial and error for other people’s experience

First-time founders think every new situation is unique to them and solve issues through trial and error a lot. Second-time founders know a lot of people have experienced their “unique” problems before. They would rather spend time finding the person who has solved it already instead of slowly and painfully solving everything…