I have started a bunch of companies and non-profits over my career.
I love all stages of building a company, but my favorite, by far, is the "0 to 1" stage. This is when you have a problem that irritates you, and an idea of how to solve it. At first there is both excitement (what if my solution works) and fear (what if everyone hates it). I love this stage.
After I left Kayak, I opened an incubator named Blade, where we invested in other people's ideas. One day, my friend and mentor Youngme Moon said "these companies are interesting, but it seems what gets you most excited is ideating and building something yourself. Why don't you do that again?"
This was a major epiphany for me. Very quickly, the Blade team came up with our own idea around business travel, and Blade then quickly morphed to become Lola.com. Six years later, we sold Lola to Capital One. As soon as my Lola engineers were well situated at Capital One, I knew it was time for me to make my next move.
I decided to do what Youngme said I was best at - ideating and building.
This time, instead of building an incubator to help other founders with their ideas, at Boston Venture Studio (BVS), we are going to focus on our own ideas. You can read about our process here.