The Scrupulous Entrepreneur: When do I leave my job to pursue my startup?

Written by Jason Shrensky, Dingman Center Angel in Residence

Often the question is posed: When do I leave my job to pursue my startup?  If you read the technology press, the answer seems to be “right away!” “Follow your dream!” is the advice of some successful entrepreneurs. To paraphrase others: “I couldn’t sleep at night just thinking about the opportunity. I quit my job the next day. You should do the same.” Of course, this flippant advice is offered in hindsight, often in the afterglow of a financial windfall. The scrupulous entrepreneur will answer this question for him or herself only after taking into account two big considerations.

The first consideration in deciding whether to leave your job to pursue your startup is family impact. How would you characterize the entrepreneurs quoted above if you knew that when they quit their day jobs to pursue their startups they had no plan to make sure that their kids had health insurance? Stupid? Reckless? Irresponsible? Would you want to invest in an entrepreneur that made such a choice?

One of the great unheralded traits of good entrepreneurs is the ability to get a business up and running without bankrupting themselves and hurting their families. To state the obvious, creating a self-sustaining business is hard. An absolute given is that the cost in terms of the entrepreneur’s time commitment is high and taxing not only to the entrepreneur but to the entrepreneur’s family.

Assuming that the entrepreneur and his or her family agree to assume the ramifications of the great time commitment involved, a second conversation that has to occur concerns the financial commitment. Leaving one’s job to pursue a startup will require financial belt-tightening by the entrepreneur and his or her family. Nonetheless, if there is buy-in from the entrepreneur’s family, a drop in discretionary spending and luxuries is easy to endure with the long-term goal of a successful venture in focus.

Thus, the lesson of the scrupulous entrepreneur who is considering family impact before pursuing a startup full time is that a) discomfort is okay, b) recklessness is not okay, and c) buy-in is required. (If you are 22 years old, single, and living with your parents, you’re good to go.)

But even after overcoming the first consideration, scrupulous entrepreneurs won’t rush to resign. The great first act of scrupulous entrepreneurs is staying employed as long as they can in order to “fund their hobby.” If they can manage getting their startups off the ground while fulfilling the duties of their day jobs, they will do it. (If working on their startups while employed would somehow be considered more unethical than conducting a search for a new job while employed, they will resign.)

It may seem like your day job is weighing you down and preventing you from moving as fast as you want on your startup. But, often the alternative is to quit your job and raise angel money. You are likely to find that raising angel money is just as time consuming yet less rewarding than your day job. If you have the right perspective, you should see your current employer as your first angel investor with the bonus that you don’t give up equity in your startup. Your paycheck is a sure thing; angel money is not.

Obviously, a separate email address and mobile phone are key tools for maintaining your double life. But don’t discount your vacation days. Use them judiciously. No trips to the beach. Vacation days are important for attending meetings and industry conferences relevant to your startup or cashing out when you eventually leave your employer.

In conclusion, leading a double life is hard, but many times it’s either necessary or simply the prudent choice. Scrupulous entrepreneurs value their families and fight on all fronts for advantages for their startups. They also don’t get any sleep. If you are a scrupulous entrepreneur, you won’t either.

Jason Shrensky is a local entrepreneur and angel investor who joined the Dingman Center team as an Angel in Residence in 2011. In addition to actively investing in early-stage companies, he splits his time between two startups that he recently co-founded: ÜberOffices and ComplexInterests. ÜberOffices provides co-working office space in the DC Metro area predominantly for early-stage technology and media companies. At ComplexInterests, Jason is working on developing a unique enterprise software package targeted at accounting, law, and financial services firms.

Connect with Jason on LinkedIn, Twitter, and Google+

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One thought on “The Scrupulous Entrepreneur: When do I leave my job to pursue my startup?

  1. Even though so much is on the line for me this week, I have learned a lot about patience and compassion for myself during this time…such a short period of time. I took some rash leaps in the recent past. They didn’t turn out quite how I would have liked for them to, but I have been earning a living and I am grateful for that. In terms of your point as a whole, I really do hear and see much validity in your case.

    Can you clarify this statement?

    “If working on their startups while employed would somehow be considered more unethical than conducting a search for a new job while employed, they will resign.”

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