10 Reasons Not to Be an Entrepreneur

And one reason to do it.

There is no TV series that captures the feeling of being an entrepreneur better than The Bear. Here’s a two-minute appetizer:

More than WeCrashed, Super Pumped, or The Dropout, this series captures the frenetic pace, the heroic efforts, stupid mistakes, camaraderie and disappointments of being a founder. It can be anxiety-inducing, even if you’ve never worked in a kitchen. It’s also positive and inspiring. But not in the treacly way most people describe entrepreneurship, like this Zions Bank ad:

It’s hard for people, myself included, not to be relentlessly positive about entrepreneurs:

But maybe it’s not such a good idea to suggest everyone should start a company or that a positive mindset is all that’s needed (I know Harley didn’t say that). That seems to be missing part of the story.

You know what I think would be helpful? A dose of reality about what entrepreneurs should really expect.

Here’s my list of ten things people should think about before starting a company.

1. Money

The reality is that there is no such thing as startup funding. Before you attract even the earliest of investors you need your own money. For lean startups you’re paying for food and rent because you aren’t earning a salary. You need cash to pay for expenses until you start making money. Who can afford to be an entrepreneur? It turns out your parents’ incomes most strongly correlate to you being a startup founder¹. It’s not fair and it’s a problem. But before you start you have to have the means to live with financial uncertainty, possibly for years. That money has to come from somewhere.

2. Freedom

The number one reason people say they want to be an entrepreneur is to “be their own boss” or to be in control of their time. Nothing could be further from reality. In a regular job you may have one manager or maybe a cross-functional team you report to. In your own company everyone is your boss: your customers, vendors, the government, every one of your investors or lenders, and definitely the staff you rely on. Until the day they exit their companies, I’ve never heard an entrepreneur say they felt free. See The Bear.

3. Commitment

In Founders at Work by Jessica Livingston, Joe Kraus, one of the founders of Excite, says:

“We decided to start a company together before we had any idea what we were going to work on. But we were so committed to the idea of starting something together that we knew we were going to figure it out.”

Committing to start is easy. But most people do not spend much time thinking about the length of that commitment which, even for SaaS companies, is 10 years. It’s much higher in some industries: 30 years if you are in aircraft parts. But it’s much shorter if, like 50% of all new businesses, you don’t make it past 5 years.

4. Uncertainty

Most people want to be the kind of person who is “okay with uncertainty.” Most are not. Life and work are full of uncertainties. But two things make startup uncertainty particularly stressful.

First, it’s the sheer volume of things you don’t know or can’t control. Will your co-founder, who you split 50% of the equity with, be just as valuable in five years? Uncertain. Will you be able to raise the money you need when you need it or even make next week’s payroll? Uncertain.

Second, you have to pair your gnawing uncertainty with being outwardly certain. No one wants to hear too much self-doubt (see Doubt below). Transparency is wonderful but every founder, at some point, decides it’s in their best interest to hide some of their uncertainties.

The best way to know if you’re okay with uncertainty is to ask yourself if you’ve ever done something where a) you weren’t in control and b) you didn’t fully understand the rules of the game.

5. Pitching

Matt Turck on Threads

Most founders love talking about what they do. Many enjoy sales. I don’t think anyone enjoys fundraising. But when you picture your future life as an entrepreneur picture yourself pitching. Because it is the thing you will do more than anything. Convincing co-founders to join you. Getting your relatives to invest. Getting people to buy. Attracting that investor, advisor, mentor. Recording that TikTok. You get the picture. It’s exhausting. And you have to do it over and over again with a smile.

6. Repetition

Pitching isn’t the only thing you’ll do repeatedly. I wrote an article called Repetition is Sexy, unironically. This is an overlooked topic because it’s sexier to talk about one-time things like bursts of inspiration, closing a big deal, or going public. The tens of thousands of hours between those moments is called running a business. In the right hands, repetition is a superpower. But make no mistake, it’s also a grind.

7. Passion

One way to kill your passion for something is to start a business around it. The little details and decisions are like little paper cuts that eventually make you bleed out. No matter what your true passion is, to run a business you need to be a generalist. In The Bear 99% of what the chef does is not cook. That is realistic. Starting a business means being okay with diluting your passion with other things.

On the other hand, and this is a bit of good news, you don’t need a deep passion to start a business. It can definitely help but then Stuart Butterfield’s passion was gaming and that company (Glitch) became a corporate communications platform (Slack). Which he’s passionate about too.

8. Doubt

There are two kinds of doubt: self-doubt and everyone telling you that you suck.

Self-doubt is something that entrepreneurs and artists share and that, I believe, is essential to creativity.

I am assailed by my own ignorance and inability. … Sometimes, I seem to do a little good piece of work, but when it is done it slides into mediocrity.

—John Steinbeck

If doubt is essential it’s definitely not enjoyable. It’s hard not to have imposter syndrome when you’re trying to do something no one’s ever done before.

The doubts of others seems like something you should be able to tune out. Like, we’ve all been to Thanksgiving dinner. Unfortunately, when you have your own company your name/ego/soul is intertwined with your business. Your failures are more public and some people just like saying “I told you so.”

9. Learning fatigue

The best entrepreneurs are the ones who are constantly learning. Because the rest are out of business. There are no standard playbooks when you start something new. Even if you knew every secret of a successful billionaire you would only know what worked for a different person, a different business, in different situations at a different time.

You still need to do it yourself. That’s why they say “there are good days, and days you learn.” I hope you have many good days but I can guarantee you’ll be learning.

Over hundreds and thousands of days this is exhausting. Sometimes you won’t feel like learning about capital dividend accounts and using ChatGPT and how to be successful on Threads.

10. Opting Out

No matter how respected entrepreneurs are, only a tiny fraction of people ever become one. It’s definitely an alternative lifestyle.

Starting a company is opting out of the usual rhythm of life. Everything from when you go on vacation, who you spend time with, when you get married or have children can be impacted because you have a big, hairy, audacious competing priority.

I’ve never known anything but this irregular rhythm so I have no basis of comparison. I guess I like being a rebel.

If you’re still reading…

In case reading this was a downer, let me leave you with this:

There’s no other path in life that pays as much compound interest as being an entrepreneur.

Every experience, good or bad, and every outcome, successful or not, pays you something. An insight, a perspective, a new skill or piece of knowledge that you never would have gained before.

Use those hard-won lessons any way you like. But you won’t find any other endeavor that will force you to be better, faster.

It’s just not easy and don’t believe anyone who says it is. I’m not a fan of hustle porn but I’m also not a fan of the Disneyfication of entrepreneurship.

As Chef Richie from The Bear says, “You’re not a chef until you’ve cried in the walk-in.”

1. https://www.jpost.com/israel-news/parents-income-not-smarts-key-to-entrepreneurship-study-657058