After selling my first company to Groupon, I wanted to work on something that would inspire me and allow me to create new skills and knowledge. I never want to be 80 years old looking backwards and wondering what if I tried.

After my previous company faced challenges, I took time off for soul-searching and was inspired by the power of nature during a trip to the Amazon rainforest.

After Looped was acquired, I took a mid-career sabbatical to travel and invest, but I realized I didn't enjoy being a seed investor.

Taking a year off between jobs can be incredibly beneficial; it allows for exploration, learning, and reconnecting with life.

After quitting my job at Amazon, I moved to San Francisco where I found a co-founder and began working on various startup ideas without being picky about the market.

While running 'The Point', we launched Groupon as a side project, which allowed me to shift my focus without admitting that 'The Point' was failing.

I initially pursued a career in tech, working at Amazon and Groupon, but I found that chasing what I thought I knew gave me a sense of competence without purpose, leading me to realize the importance of following my passions.

I initially thought there was no way I could be the one to discover the formula for supersonic passenger flight, but it turned out to be liberating to realize that I could find the flaws in the existing assumptions.

I wanted to work on flight because it would make me the happiest if it worked, and I believe that if every founder pursued the most ambitious ideas they could conceive, it would lead to greater happiness and innovation.