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The Multi-Startup Founder Conundrum

Last week, I spoke with an entrepreneur who shared his vision, his journey to date, and a compelling story. Toward the end of the meeting, he threw me a curveball. That was just one of two startups he

David Cummings
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May 2, 2026

Last week, I spoke with an entrepreneur who shared his vision, his journey to date, and a compelling story. Toward the end of the meeting, he threw me a curveball. That was just one of two startups he was working on. He then walked through his vision and ideas for the second startup.

I was challenged by this. It is hard enough to create one successful business, let alone two at the same time. In the age of AI, vibe coding, and AI agents, productivity gains for those with the right skills are significant. Naturally, some entrepreneurs are not going to limit themselves to a single idea. If you can make the technology work, why not build multiple companies at once?

The most famous entrepreneur in the world is often cited as an example, with several companies doing extraordinary things, from self-driving electric cars to rockets, satellite internet, implantable chips, and underground tunnels. That is the extreme case. Most founders are not operating at that level.

I come back to the new founder and the challenge of being a multi-startup entrepreneur. In sports, there has always been a mystique around the multi-sport athlete. Years ago, Deion Sanders famously played for both the Atlanta Braves and the Atlanta Falcons in the same day. It created buzz, but being one of the best in the world at a single sport is already extremely difficult. Trying to do it in two sports at the same time is even harder.

A modern example, within a single sport, is Shohei Ohtani of the Los Angeles Dodgers, who is both an elite hitter and pitcher. That level of dual excellence has not been seen since Babe Ruth a century ago.

As an entrepreneur, I have also pursued multiple ideas and started several companies. My approach has been sequential. Start one company, get it off the ground, bootstrap it to meaningful recurring revenue, then move to the next idea. Each time, I recruited a new team and built the next company from there.

While this can lead to multiple companies existing at the same time, they are not all being started from scratch simultaneously. Each has some level of momentum, scale, and an operating team in place.

My recommendation for a multi-startup founder is straightforward. Focus on one startup exclusively. Capture ideas for future ventures, but do not spend time building them until your current company has achieved a level of success, predictability, and scale.

At that point, if another idea is stronger or you are motivated by starting from zero, pursue it with a new team. Trying to build two startups from scratch at the same time is a recipe for failure. Pick one idea, go deep, make it work, ensure you have a team that can sustain and grow it, and only then begin building your next company.

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