What I Learned About Entrepreneurship from Larry David

A couple of weeks ago, I had the privilege of experiencing what I can honestly call the best week of my life entertainment-wise. I saw John Oliver and Seth Meyers at the Beacon in New York, then Larry David at the Fox in Atlanta. To say that my spirits were high is an understatement—I spent days afterward laughing at random moments, reliving each punchline and witty comeback. But amidst all the laughter, I found myself pondering some surprisingly insightful takeaways about entrepreneurship, sparked by a few memorable moments from each set.

One of the standouts from John Oliver’s set was his reference to a mind-boggling study: apparently, one out of eight men believe they could beat Serena Williams at tennis. I’ll let you imagine the collective reaction from the audience. But it hit me that this level of confidence, or maybe overconfidence, is almost quintessential to starting any venture, whether it’s sports, comedy, or business.

Then came Larry David’s bit about his entry into comedy. As he told it, he was simply sitting at a stand-up show one day when he thought, “I could do better than that!” And there it was—Larry’s whole comedic journey began with a simple, perhaps audacious thought that he could outperform what he saw on stage.

And that’s when it hit me: comedy and entrepreneurship share this undercurrent of audacious belief. Misogynist overtones aside, there’s something bold about thinking, “I could do better.” That’s how many entrepreneurs start, isn’t it? We spot a gap, or perhaps just something that doesn’t resonate with us, and we think, “I could improve this.”

Of course, both comedy and entrepreneurship reveal one humbling reality soon after that first leap of faith: it’s a lot harder than it looks. You can’t simply show up with an idea or a critique and expect things to unfold flawlessly. Once you’ve taken that step to get on stage or launch your business, you’re suddenly accountable for delivering on that confidence. And that’s when the real work begins—figuring out how to not just meet expectations but exceed them, a journey filled with as many challenges as triumphs.

Ultimately, both comedy and entrepreneurship hinge on a combination of daring, hard work, and relentless refinement. Comedy might make it look easy, just as successful businesses can seem effortless from the outside. But both are anything but simple behind the scenes.