How To Find Success as an Entrepreneur

Five tips from Stephen Gerard ’89M.

Stephen Gerard ’89M had 20 years of corporate experience in sales, accounting, and finance under his belt when he decided to change course and become an entrepreneur at age 40. He founded his first company in 2004 and has started, invested in, and bought and sold businesses around the world ever since. His new book, Stuck in the Middle Seat: The Five Phases to Becoming a Midcareer Entrepreneur, offers advice for anyone seeking to escape the 9-to-5 grind. He shared a few of his tips with us.

It’s Never Too Late.

Midcareer can actually be the best time to become an entrepreneur, whether you’ve set your sights on starting a side hustle or launching a major corporation. Why? You’ve likely developed the necessary business and leadership skills by that time and bring significant know-how to the table.

Do What You Love.

How do you know when you’ve found something you love? For Gerard, it must meet these three criteria: He can’t wait to do it, he loses track of time when he’s doing it, and he gets upset when someone interrupts him doing it. Though entrepreneurs can find a career they love at any age, midcareer professionals benefit from knowing what they like and don’t like as well as their strengths and weaknesses.

Refine Your Idea.

For a business idea to thrive, it must meet a market need—and make money. Beware of trying to elevate a hobby into a business, Gerard says, recalling a time when he considered becoming a professional winemaker. “I wasn’t that good at it, and I wasn’t willing to put the time in to be good at it.” Instead, talk to as many people as possible about your idea, refine it until it’s a viable business, and get referrals to speak with business owners who have done something similar.

Fail Forward.

That means learn by making mistakes. Don’t spend so much time thinking and planning that you never take a chance. Get out there and try to sell your idea. Understand that mistakes will be made, but it’s all part of the process of adapting and advancing the idea. Alternatively, too many roadblocks may reveal that you need to come up with a different plan entirely.

Sleep on It.

Entrepreneurship is emotional. Each day brings a new challenge, and it’s hard to determine whether the right reaction is to stay the course or completely panic. Gerard’s tip? Sleep on it. “Everything looks different the next day,” he says. “You’ll have more clarity and a better idea of what to do.”