Why the Best Entrepreneurs Aren’t Nearly as Visionary as People Think
Steve Jobs, Elon Musk, and other storied entrepreneurs might not be as creative as we’ve been led to believe.
I was walking through the mall with my family this past week and a clothing store had a big sign out front that read:
Leap Day Sale: Everything in the Store 29% Off!
As you’ve surely guessed from context clues, it was the week of February 29th — Leap Day — and the owners of this particular store were trying to capitalize on it. But the cynical entrepreneur in me rolled my eyes and thought, “What a stupid reason for a sale. Could a company be any less creative?”
Then I overheard a woman from the group walking behind me say, “Oooh… 29% off sale. Let’s go check it out.”
It was a humbling reminder that entrepreneurs don’t have to be creative visionaries. Sure, all entrepreneurs seem to exist in the shadows of uber-successful people like Steve Jobs, Elon Musk, and Jeff Bezos — entrepreneurs who’ve been branded as world-changing visionaries doing things nobody else in history ever imagined. But the brand of “visionary” isn’t entirely true. At least it isn’t from a tactical perspective.
From a tactical perspective, successful entrepreneurs aren’t creative geniuses constantly inventing new ways of doing business. In fact, the best entrepreneurs are perfectly happy sticking with what’s already been proven to work.
It’s a lesson I — like most entrepreneurs — have been struggling with my entire entrepreneurial career.
Reinventing magazines
Twenty years earlier in my first startup experience out of college I briefly took a job helping launch a new magazine.
This was the mid-2000s and physical magazines were still relatively popular. I’d just graduated with a degree in English Literature, making me virtually unemployable. However, for some reason, I’d caught the eye of a successful Web entrepreneur hoping to launch a hybrid digital/physical publication, and he added me to his team as the magazine’s editorial director.
I hadn’t been in the position for more than a week when the draft of our July issue came across my desk and it was filled with content related to Summer barbecues and independence day celebrations. “Could anything be less creative?” I thought. “We look like every other magazine out there. We’re a startup. We need to be creative and different!”
I made the sweeping decision to eliminate all holiday-themed content. Our October issue wasn’t going to reference pumpkins. Our November issue wouldn’t include a single mention of turkey. And the color red was strictly forbidden for the cover of our December issue.
“We’re going to be a different type of magazine,” I told the team. “We’re going to be a magazine that focuses on what’s interesting and valuable, not the month of the year.”
Fast forward six months, the magazine was in a death spiral, and I’d completely reversed my “no cliched themes” policy just in time for our February “love” issue, hoping some added emphasis on romance would save us.
Spoiler alert: It didn’t.
Anchors not weights
I probably shouldn’t blame the failure of that startup magazine on my foolish decision to stop referencing turkey on Thanksgiving. It was the mid-2000s, Facebook was taking the world by storm, Digg was one of the most popular websites on the planet, and Twitter was that strange new “micro-blogging” service only letting users post 140 characters. In other words, physical magazines were already doomed, and publishing a few extra holiday dessert recipes wasn’t likely to have saved anything.
But I often find myself blaming my stupid decision to remove holiday themes. It wasn’t the only reason we failed, but it certainly didn’t help. After all, a magazine’s theme isn’t a useless cliche weighing down creativity. The theming of a magazine is a valuable anchor that gives it familiar directionality. The theming gives magazines a cohesiveness that’s good for creators and consumers alike.
The same fundamental principle turns out to be true in most other industries, too. Strategies that seem cliche and uncreative are cliche and uncreative for good reason: It’s because they work!
Consider, for example, the Super Bowl. There’s a reason companies paid $7 million for a Super Bowl commercial in 2024. It wasn’t that marketing execs were being lazy and uninventive by purchasing the same advertising space everyone else wants to buy. It was because those marketing execs knew 120 million people would be watching the Super Bowl.
In fact, if your target buying demographic is the type of demographic that’s likely watching the Super Bowl, the only reason not to pay $7 million for a Super Bowl commercial is if you can’t afford it. But if you can afford the $7 million, it’s the best marketing money you can spend even though everyone else is spending it, too.
Great entrepreneurs understand this. They don’t run away from proven strategies just because others are already using them and they seem uncreative. Instead, the best entrepreneurs avoid being creative when possible and lean into what works. Sure, it’s not quite as “sexy” as being called a visionary, but it’s a strategy that’s simple and effective — two attributes that are the true foundation of entrepreneurial success.
