Some entrepreneurs sail blissfully into the sunset after their first big payday. Others — like us — can’t imagine anything more boring. Instead, we thrive on constantly risking it all to build something out of nothing.

This condition of serial entrepreneurship is what I call “one and not done” syndrome. Maybe we’re crazy to be willing to start a business again and again. We know it will be hard, if not seemingly impossible, and there will be times when we will be overwhelmed with frustration. In spite of that, we know the journey is worth it.

If you’re this special breed of entrepreneur, I feel both sorry and happy for you. More than anything, I welcome you to the club.

There is a magic to what we do as entrepreneurs. We can create a thrivi...