Are You Cut Out to Leave Corporate Life For an Adventure?

When I joined my first startup 25 years ago, startups were considered a place for weirdos who couldn’t hack corporate life.

After working at GM, Honeywell, and a couple of other big companies, joining a startup felt risky. My parents told me I was crazy when I joined a company as employee number 7. But after a month, I knew I’d found my home. And I knew I’d never go back to another big company again.

I enjoy wearing many hats and need the adrenalin rush of a successful experiment far more than I need a guaranteed paycheck. But that’s just me. After all, I’m a weirdo who quit my job at well-paying Honeywell because I was bored to go teach English in Japan for $20 per hour.

Nowadays the tables are turned and everybody wants to join a startup. It’s a delicious irony to receive investment pitches from senior managers at GM and Honeywell. They see the riches of successful startup founders and think they can do it better than the corporate dropouts.

But just as some people are not suited for climbing the corporate ladder, not everyone is cut out to be a founder.

Most of the pitches from corporate types look like corporate business plans. They’ve identified a product that their team at GM needs that nobody is building yet. It’s a great idea. But they’re looking for funding to build the MVP with a staff of 25 people, all of them getting paid at market rates including the founders. Sorry, nope, it doesn’t work that way.

After explaining how startups work, they ask, “Then how do we get funding to build the product?”

To a real founder, the answer is obvious: you build it yourself working nights and weekends. Then you beg people to try the MVP and give you feedback to validate product-market fit. Then you get a smidgeon of money to hire a small team to commercialize the product and begin selling.

“But I’ve got a great sales guy lined up right now and need funding to pay him.”

If I’m in a generous mood, I’ll explain why the founders need to do the sales themselves for the next 3 years as part of customer discovery. If not, he’ll have to figure that out himself.

“But I’m not a sales guy,” is the usual protest.

You are now. If you’re a startup founder, you’re doing sales full time for the next 3 years. Not only do you have to sell the product to customers, but you also have to sell stock to investors, too.

“How will I have time for that and build the product, too?”

You’ll be working 15 hour days for the next 3 years. For no salary.

“But what about health insurance?”

Um…yeah. Maybe you should think of staying at GM.

Corporate managers bring a wealth of experience, connections, and industry expertise that can help a startup succeed. Corporate managers may have led successful new product introductions, had P&L responsibility for billion-dollar products and managed a team of thousands. But building a startup on your own without the backing and budget of a big corporation is not for everyone.

Here are the character traits I think are needed to be a successful startup founder:

  1. Love to wear many hats. You’ll be doing product design (even if you’re the business guy), marketing, sales, fundraising, and even basic accounting, HR, and legal. All the various departments of a big company get rolled up into the co-founders. If you’re bored at a big company where you get pigeonholed into a narrow set of responsibilities, you’ll love startup life where you have to handle every detail yourself.
  2. Love to get your hands dirty. Corporate managers are good at…managing. It’s an important skill, but not one that’s useful when the startup has nobody to manage. If you don’t mind doing whatever it takes, including answering calls to the support line in the middle of the night, you’ll be comfortable at a startup. (Conversely, a lot of startups devolve into chaos around Series B when the staff grows to 100+ people and none of the founding team has any experience managing.)
  3. Workaholic. If you like a 9–5 job with vacations where you can turn off the phone and relax, a startup is not for you. You’ll be working 3 full-time jobs simultaneously: building the product, selling the product, and fundraising. If you get a buzz from dealing with customers in Germany at 5 AM and contractors in India at 11 PM, you’re in the right place. Especially if you don’t mind doing all that work without getting paid.
  4. Survive without a salary. As a founder, you’re working for equity rather than a salary. At the start, there’s no income at all. Once the startup has investors and customers, it can pay the founders a modest salary, but it won’t be market rate. If you need the salary you’re making now to support your family, it’s best to hold off on founding a startup until you’re financially secure.
  5. Handle adversity. Corporate life has its challenges, but startups are 10x worse. Every day is a battle for survival. There are brutal fights with cofounders about everything from the company direction to the color of a button on the UI. There’s frustration when customers don’t get it. There’s an ulcer when the bank account is running low and investors aren’t biting on funding the next round. Even when things are going well at a startup, it’s 3 steps forward and 2.9 steps back. When they’re not, it’s 1 step forward and 10 steps back. Can you handle banging your head against a brick wall every day for years? Good. I’ve got some extra bricks leftover from my startups you can borrow.
  6. Flexible: Startups are about iteration. You can spend years perfecting the business plan, but it won’t survive the first customer encounter. A startup does exactly what a big corporation can’t — trial and error. Put something out, see what works, and revise. Daily. No staff meetings, PowerPoint presentations, or endless discussion. Make the changes, try it today, then try something else tomorrow. Not only is the product an iterative experimental process, but so is the marketing, the sales messaging, the investor pitch, and the team itself.
  7. Ability to cope with failure. Every founder claims failure is not an option. But with odds of between 1-in-10 and 1-in-1000, founders need to be able to cope with things not working out and bounce back instead of falling apart. The best founders learn from failure and use it to grow stronger.
  8. Enjoy adventure. The greatest thing about startup life is every day is an adventure. Sometimes you’re stuck so far in the mud that you have no idea how to claw out. If that sounds like your idea of a dream job, welcome aboard — you’ll enjoy building a startup much more than a boring corporate job.

Disagree with any of these? Or did I miss some key trait?

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