Don't Quit Your Day Job (Yet)

I think a lot of founders make the same mistake I made with my first startup: they quit their jobs way too early.

I left a stable job to go all-in before I really had a business. It was a great experience, but to be honest, it took a lot out of me. And it didn't work out.

So when I approached James in the winter of 2014 to start tinkering on something new, I wasn't ready to do "a startup" again. I had a mortgage. I had car payments. My kids were young - between three and seven years old. I couldn't put my family through that stress again.

My wife was very, very hesitant about me doing this a second time. The first one didn't go well personally for us - we nearly got divorced. So I had to sell her on a different approach. I told her, "It's not going to be a startup where we work 24 hours a day. We're actually going to be working less. We'll do our nine-to-fives, work on this in the evenings, and that’s it."

We kept our day jobs for 18 months.

From June 2015 when we launched until February 2017, James, Sean, Julian and I worked nights and weekends. We’d work our full-time jobs, come home, put the kids to bed, and then work from 8 PM to midnight.

Most people think this shows a lack of commitment. They think if you're serious, you have to burn the boats and quit your job - go all in!

But I think the opposite is true. Building software isn't like building widgets. You're using your brain to build something, and it's a creative process. Your brain needs to work properly to do that. If you've got stress - if you're worried about how you're going to pay for groceries or support your kids - your brain is not going to be free to do its best work.

Because we had paychecks coming in, we didn't have the pressure to make bad short-term decisions. We could treat Rewind like an experiment. If it failed, we still had our jobs. That freedom allowed us to think clearly.

When we finally did quit, it wasn't a leap of faith. It was just basic math.

We had a rule: we wouldn't quit until the monthly revenue could cover a salary plus expenses. We figured that was around $15,000 to $20,000 a month.

We didn't even all quit at the same time. We said, "Let's try one person." Once the revenue hit that $15K mark, Sean (our first employee) quit his job. Then we kept growing. When the revenue doubled, Julian and I quit in February 2017. James joined us a few months later.

None of us had to take a salary cut. We maintained our old salaries on the new company's dime.

So if you're thinking about starting something, don't feel pressured to hand in your resignation tomorrow. Keep your day job. Let the revenue dictate the timing.

You'll make better decisions when you aren't terrified of your bank balance.