• In the early days of a venture, an entrepreneur is often a one-man show.
  • However, in the end, it is necessary to move from the opening stage to the recruitment and guidance stage.
  • Here, expert and Grubhub founder Mike Evans shares how founders can tackle challenges.
  • This article is part of Talent Insider, a series with expert advice to help small business owners tackle a variety of hiring challenges.

In the early days of a venture, entrepreneurs and small business owners are one show. They are the company’s chief sales representative, marketer, financial director, and product officer.

But once the business takes off, founders have to move from starting the business, to hiring employees, to leading the team. According to Caroline Daniels, professor of entrepreneurship at Babson College, the change doesn’t come naturally and she’s one of the hardest things for entrepreneurs and small business owners to do.

“You have to move from single point of view to multiple points of view and from actor to teacher,” she said. “And we need to recognize that our future direction, and the ultimate success of the company, will depend on how well we manage that change.”

Insider spoke with three experts, including Grubhub founder Mike Evans, about how founders and small business owners can make the transition smoother.

First Hire Strategically

Evans founded Grubhub, an online food delivery platform, out of his Chicago apartment in 2002 at the age of 26. In his first few years he did everything by himself, but as his business grew he realized he needed help.

Grubhub founder Mike Evans

Grubhub founder Mike Evans.

grub hub


His first few hires fell into two categories. “First, he wanted to hire someone who was obviously good at what he wasn’t good at,” Evans said. Evans’ memoir, “Hungry: A Startup Journey,” will be published later this year. “For me, it was sales. I needed expertise and someone who could do it better.”

The second category was people who could take on household chores or tasks that he disliked. and less time spent on business.”

Before Grubhub launched online ordering, it was a takeout menu platform. Evans had to physically collect the menu, scan it, crop it, and upload it to the Internet. It was a tedious process.

So he hired a young graphic designer, Jack Kent, who was scooping ice cream at the time. Kent was untested, but Evans saw potential. “Startups don’t have the money to hire people who are very experienced,” he said. “They have to learn on the job. Some people are really surprised.”

A few years later, Kent was promoted to head creative for the company’s first Super Bowl ad. “It’s a joy to see people learn and grow,” said Evans. “It’s good for them and good for the business.”

learn to let go

In nearly eight years running Grubhub, Evans has learned a hard lesson about the importance of trusting your employees. One day, Evans, who has a software background, made a management decision at 2am to change a key line of code in his Grubhub that relates to a suggested tip.

The next day, the company’s lead developer promptly removed Evans’ access to write code. Looking back, Evans realized that his actions undermined the team’s ability to get the job done. “The company was growing, and having founders create software for their business was no longer the best thing for their business,” he said. He “realized that I needed to take a step back from tinkering with everything and let people do their jobs without my interference.”

Letting go of control can be a challenge for founders, who are often deeply invested in their business, according to experts. Laura Lemon, an assistant professor who studies employee engagement at the University of Alabama, said, “You have to surrender control of the part of your business, perhaps the part you think of as your child, to an outsider. No, but it’s difficult,” he said.

Laura L. Lemon, Assistant Professor, University of Alabama

Laura Lemmon, assistant professor at the University of Alabama.

University of Alabama


But you have to understand that while it may not be easy, it is important to your employees and to your health. And you don’t want to burn yourself out claiming you’re involved in everything.

Mandate the results you want, but don’t prescribe them, Lemon added. she said.

Tell stories to inspire new hires

Research shows that entrepreneurs and founders are enthusiastic and hardworking people. Their single-mindedness is beneficial in building a business, but it comes at a price, Babson’s Daniels said. “She’s been told 50 times that most entrepreneurs don’t work or succeed at what they do,” she added. “If they can make it work, it gives them confidence, but it also comes with a lot of dangerous arrogance.”

Humility is key. Don’t assume that other people are just as focused and passionate as you are. Instead, tell a story that communicates your values ​​and beliefs, Daniels said. Talk about why you started the company and what you want to achieve. With their help, of course. “You are I know why I’m building a company, but other people don’t,” she said.

Describe the problem you want to solve, experts say. Build buy-in by using “we” pronouns and demonstrating the power of teamwork. Draw a compelling vision of the future.

Daniels said:

“The message should be: We are working on this together.”



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