My father was heartbroken when music moved away from vinyl to CDs and then to digital. At the time, it made no sense to me. “It just doesn’t feel the same,” he’d explain as he cued up another LP. Only now, 40 years later, with the rise of AI, do I truly understand what he…

When someone uses 'low eight figures,' that means barely eight figures.

I tell young entrepreneurs all the time; The future doesn’t care about the past. If you want your company to succeed, you have to have the confidence in your business to take a bet on its future — to risk destroying a mediocre business model for the chance to have a strong one.

Optimism is a double-edged sword. Being a relentless optimist has sustained me through all sorts of challenges and frustrations as an entrepreneur. But as an angel investor, it’s meant that I like nearly every idea I see—which isn’t necessarily great for picking which ones to…

I’ve been a part of starting six companies. I’ve mentored several dozen founding teams.  I’ve invested in more than 100 early-stage companies, and I’ve heard countless pitches.   All of that has given me a finely tuned sense of the factors that really matter for the success of…