Investor Strategy

Use this checklist from Shopify’s president to determine when it’s time to make your side hustle your full-time business venture

  • Many successful companies started out as side hustles, but it’s not always clear when it’s the right time to leave your day job to focus on growing your business full-time.
  • Shopify’s president, Harley Finkelstein appears in the Discovery series “I Quit” as a mentor to six contestants who quit their jobs to focus on their businesses full-time.
  • Finkelstein told Business Insider what questions you should ask yourself if you’re thinking of taking your side hustle business full time.
  • Visit Business Insider’s homepage for more stories.

Many successful companies started out as side hustles — Steve Jobs worked at Atari and Steve Wozniak worked for HP while they built their first Apple computer.

But it’s not always clear when it’s the right time to leave your “day job” to focus on growing your business. It’s both an exciting opportunity and a major risk.

Harley Finkelstein is the president of Shopify, one of the largest ecommerce platforms in the world, and appears in the Discovery series “I Quit” as a mentor to six entrepreneurs who quit their jobs to focus on their side hustles full-time.

In an interview with Business Insider, Finkelstein said it’s important for entrepreneurs to establish when they will go “all in” with their business. “Your side hustle may actually be your life’s work and your nine-to-five may just be something that you are doing in anticipation for doing your life’s work full time,” he said. “Having a side hustle in perpetuity actually is not in an entrepreneur’s best interest.”

Based on his advice, here are the questions you should ask yourself if you’re thinking of taking your side hustle business full-time.

What’s your personal risk tolerance?

Finkelstein said everyone has a different risk tolerance based on their responsibilities, life circumstances, and financial situations. For example, a father of four children in his 50s might not feel comfortable taking the same risks as a single man in his 20s with no children.

Quitting your full-time job to pursue your business often depends on the number of people in your household, when you plan to retire, healthcare, how your family’s quality of life will change, and how much you have in savings, as well as many other factors.

What’s your ‘I quit’ milestone?

One mistake entrepreneurs often make, Finkelstein said, is not defining their timeline at the start. Too many end up pursuing their side hustles indefinitely and stunt their own growth. Determine the timeline that works best for you by creating a milestone or metric to hit in order to quit your job, such as hitting your hundredth sale or first $50,000 in sales.

“You should establish that really early on,” he said. “If you’re very clear about that at the outset, then it becomes very easy to map your journey as you go.”

Are you a founder people can bet on?

As an investor and mentor, Finkelstein said a founder’s personality carries more weight than the business itself. That’s because the business could transform into several iterations from the time of conception — Shopify began as an online snowboard shop, before it became a software company.

“If you bet on a great entrepreneur who is resourceful and who has grit, that’s a really good investment to make,” he said. Resourcefulness and grit are two common traits he notices in successful entrepreneurs and will set founders apart when they’re taking their side hustles full time.

“Some entrepreneurs and founders that quit their jobs and you see it in their eyes. They’re going to be able to do anything in the world to make sure the business is successful,” he said.

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