18. While starting a business, when should you quit your day job?

I love working with founders. Helping them grow their businesses brings me joy. However, there is one question I hear from very early-stage founders that is always awkward. “When do I need to quit my day job?”

Typically the company is pre-revenue and either self-funded or only has friends and family as investors. The dream is to eventually be working full time in their thriving company, but in the very early stages, there is no income and high risk. To get to that promised land, the company needs to raise capital, and therein lies the problem. Angels are unlikely to invest until the founder is 100% in the startup.

In some cases, you can bootstrap a company without outside investment while still working at a conventional job, but it is a much slower process. Investors know that time is the enemy. They worry that competitors will emerge or market conditions change to capsize the business. Having the founder working beyond full time on the company ensures the fastest path to growth.

Besides, investors want to cut off easy paths of retreat for the founder. There are always rough patches in the life of any startup. The obstacles will seem insurmountable. Angel investors need reassurance that the founder will not cut and run but instead find some way over, around, or through the problem.

Unfortunately, this puts the founder at significant risk. Most startups fail, which can leave the entrepreneur in a tough place. I feel an ethical dilemma when talking to founders about this. As a human, I understand the risk and potential downside. If they have children, a mortgage, and other commitments, it is probably not a sound financial decision. On the other hand, as an investor, I know that if they want to be successful entrepreneurs with outside investment, there is little other choice.

This is one reason that a significant fraction of founders are young and childless. They have little to lose. I remember going through this analysis myself back in 1995 when I was thinking about starting what became Anonymizer. I had a long discussion with my wife about the possible outcomes. At the time, we were both impoverished graduate students renting a small house from my parents. We had no assets to lose, landlords that were unlikely to push us out on the streets, and no real commitments. We also knew that I could easily go back to the Ph.D. program if things did not work out. So, the downside risk to me was minimal. At worst, I would declare bankruptcy and be back where I started.

For someone mid-career with family, property, assets, retirement savings, and all the rest, it is a much different calculus. Frustratingly, those people also make the best entrepreneurs. They have experience in the industry, know the pain points intimately, and have connections to help them enter the market.

My best advice is to wait as long as possible before leaving the safe shores of a stable job. Do everything you can to risk reduce the business. Prototypes, market research, interviews, and all kinds of experiments can either show the company is doomed (at least in its current form) or confirm many of your critical assumptions. In addition to reducing your risk, it also reduces the risk for the investors, making it easier to raise capital. Only then should you take the plunge and quit your job to go full time on the startup, and only if you are confident that failure would not be disastrous.