What Startups Can Teach Enterprises About Making Bold Bets

Startups can't afford fear bold moves—they have to take them. When the status quo isn’t an option, risk becomes a calculated necessity.

But, as my dad loves to say, "here’s the deal": this isn’t just a startup lesson.

Enterprises need bold bets, too. Yet too often, I see large companies cling to safety, doubling down on what’s “worked” instead of leaning into what could work.

The result? Best case scenario is they end up in stagnation land. Worst case, they slowly, but steadily, end up playing the game on extra-hard mode. Playing a game in hard mode causes burnout and employee churn.

The simple truth is that playing it safe won’t drive the necessary growth that enterprises want.

Startups move fast because they embrace risk backed by data. They iterate, they learn, and yes—they fail sometimes. But when they win, it’s because they had the guts to make the big plays.

Enterprises, on the other hand, have the resources and the data to make bold, calculated bets. So why hesitate? Why settle for incremental change when the opportunity for exponential growth is right there?

Big bets won’t always pay off. But staying in your comfort zone? That guarantees mediocrity.

This is a topic that I've been having with friends in large enterprises that are trying to embrace the "we are a start-up inside a big company" mentality. It is really tough to get the powers that be to embrace these risks.

So, here’s my challenge:
🥊 What’s one bold move your team can make this quarter to break through the status quo?

If you want to share it, do so below...