Ready For An Entrepreneurial Bet?

When you are your own boss, going “all in” is often necessary.

Ready For An Entrepreneurial Bet?
Photo by Chris Liverani / Unsplash

I played a lot of poker in college.

The World Series of Poker was wildly popular on ESPN and encouraged our amateur adoption of the sport. One evening, in the dorm study room, a few friends and I were engaged in a serious battle of poker. We used pretzels and mustard as poker chips, which presented a problem where the currency was both editable and delicious.

Anyway, as the night went on, the game grew more uninteresting by the minute. Looking to end the night, I decided it was time to say the three magic words: “I’m all in.”

No Rules Rules

I recently read No Rules Rules, the philosophy behind Netflix’s business culture. Netflix’s founder Reed Hastings, at one point, equates entrepreneurship to taking bets. He wants all employees to feel empowered to take entrepreneurial bets on things they believe will benefit the company.

Hastings provides a good analogy. Not all entrepreneurial bets are big, all in moments. Many are small choices that either helps your business grow or provides a learning opportunity.

I make small entrepreneurial bets all the time in my freelance business. Investing money into a certain marketing channel or spending time to develop reproducible content. These are both bets I hope to pay off in the long run but require a certain leap in the short term.

Hit Delete

A few years ago, I decided it was time to shutter The Writing Cooperative’s Slack community. At the time, we had over 7,000 members. Granted, many were inactive, but that’s still an accomplishment. While our Slack community served a specific purpose in concept, it developed into a den of spam and generally was not fun to be part of.

Deciding to cut 7,000 people from a communication tool is not an easy decision and a huge bet. Ultimately, it paid off as the current communication channels for The Writing Cooperative are spam-free and more active than ever.

Place Your Entrepreneurial Bet

Managing a business requires taking bets. No matter how big or small, the entrepreneurial bet helps move your business forward with financial gains or educational moments.

Did my college pretzel bet pay off? Well, no. But I did get out of the game, which was my goal in going all in. So, in a way, you can say I won.

What is your next entrepreneurial bet?