The scariest decision is to leave a salary and join our startup full-time

The founders of a startup asked me a simple question. They’ve been working on their startup on nights and weekends while holding a regular job during the day. They wanted to know when they should quit their jobs and join the startup full-time.

I hemmed and hawed and finally gave a non-answer. But since this is the most difficult question every founder struggles with, I’ve been thinking about it since then to try to come up with a better answer.

Leaving a job with a salary and health insurance to join an untested startup is like stepping off a ledge. Even if you have a parachute, you’ve never tested it.

For me, the decision to go all-in with my own startup was easy, though no less scary.

The company where I’d been head of marketing for many years was acquired by a bigger partner. The deal was structured so that most of the benefit to the employees was in retention bonuses, which isn’t unusual. My bonus was nearly a million dollars if I stayed on for 3 years and we hit our numbers.

Within weeks, it became clear I didn’t fit into the new company. I came home every night fuming at the decisions being made by clueless people at headquarters who didn’t understand the business they’d acquired. Still, a million dollars is a lot of money. I’d have to find a way to suck it up and stick it out.

After a few months, my wife sat me down for a lecture. She said, “DC, you can’t go on like this. You’re miserable all the time. And you’re making me miserable, too.”

She was right. My frustration in the office had turned to surliness and depression at home. I promised to change my attitude. I’d try not to take work so seriously. I’d put in my time and not let it get to me. It was only 3 years. I’d find a way to survive.

“That’s not you,” she said. “You need to get out of there before you make yourself sick.”

“It’s a million dollars,” I reminded her.

“Do you care?” she asked.

A million dollars would mean financial freedom for the rest of our lives. If we had kids, it would mean they’d be taken care of even if I got hit by the proverbial bus.

“A million dollars is worthless if it makes you sick. Three years is too long to be miserable. You need to get out now.”

Wow. If I didn’t know it before, I’d married the right woman.

The next day I put in my notice. But that left the question of what to do next.

So I looked for a job. Unfortunately, my non-compete agreement left me unable to work for any company interested in me.

After a few months at home writing a novel while sending out resumes, my wife sat me down again for another lecture. “You’re driving me crazy yelling at the computer all day. I don’t care what you do, but get out of the house.”

She worked at home and in pre-Covid days, was used to having the place to herself during the day. As many of us learned over the past year, marital bliss is best savored less than 24 hours a day.

Fortunately, one of my colleagues had left the same company, and we had an idea for a product we were certain our previous customers needed. So we started the company and moved into a sub-leased office the next day. We turned out to be right and within a few years, were raking in serious profits.

We were lucky — we had enough savings to build the product without investors or taking on consulting work to pay the mortgage. But my situation was unique. So I’m not sure I’m qualified to give anyone else advice on when they should quit their job and join a startup.

But the more I thought about it, the more I realized that neither can anyone else answer that question for another person. Everyone’s situation is intensely unique. When to make that leap off the ledge to join a startup full-time is a decision every founder has to make for themselves based on their own circumstances and comfort.

The best analogy I can give is joining a startup full-time is like deciding to get married. If you have to ask if you’re doing the right thing, the answer is you probably aren’t. If it doesn’t feel right, if it doesn’t feel inevitable, if it doesn’t feel like the one, it probably isn’t. If you have to do a pro-con or trade-off analysis, you may not be ready.

The factors to consider are the same for all of us, but our specific circumstances differ.

  • Can we afford to quit our job?
  • Do we have a family to support or a mortgage to pay, or are we at a point in our lives when we can take a big risk?
  • Do we have a working spouse who can support us until the business takes off?
  • Are we leaving behind a career that will be difficult to come back to, or are we in a flexible situation like consulting we can return to if the startup don’t work out?
  • Is there time pressure on the startup that requires us to jump in now? If it takes twice as long to complete the product because we’re working part time, will we lose potential customers or get passed by the competition?
  • What is the risk profile of the business — is it like most venture startups with at best a 10% chance of survival, or has it been de-risked with a known customer base clamoring for the solution?
  • Does the startup have customers already validating the business? Is it generating revenues that pay at least some of the bills?
  • Is the startup able to pay basic salaries yet? Are grants available to help?
  • What is our personal comfort with risk?

The last item, our personal comfort, is without a doubt the most important. Does the possibility of not being able to pay the rent paralyze us with fear or get us out of bed every morning zipping with excitement?

In the end, like getting married, when the time is right to quit the job and join the startup full-time, it should feel inevitable, like the only possible path forward. That’s a decision only you can make. Whatever you do decide, know I’m here to support you.