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Building a Business That Lasts with Jay Owen

May 12, 2019

Jay Owen has worked hard for his success. He’s seen his business grow consistently for the last 20 years.

But what did it take to get there? Find out on this episode of The Thoughtful Entrepreneur.

Jay Owen started his first business at the age of eight. He noticed a lack of concessions at local baseball games and decided to do something about it. With the help of his mom, he made a trip to Sam’s Club and stocked up. Then, he started selling snacks and refreshments out of a little red wagon at the games.

By 12, he’d started a second business mowing lawns.

“Which I think every 12-year-old boy does at some point,” Jay said.

Around the same age, Jay designed his first website. At 16, a neighbor helped Jay secure an internship building websites at a company. That turned into a job and he stayed for about a year.

“I thought, ‘Gosh, I think I could do this for myself,’” Jay said.

He started his digital agency Design Extensions when he was 17. Since then, they’ve grown consistently.

“This is our 20th year of business,” Jay said. “We’ve grown every single year, year-over-year, for 20 years in a row.”

So has the internet, which has forced Jay to learn how to adapt.

“I think that’s one of the things as an entrepreneur or business owner: You have to be able to change as things change,” Jay said. “I think one of the biggest mistakes people make is they get stuck in these ruts.”

Having a Mentor

Along with being adaptable, Jay says he’s been successful, in part, because of the people around him.

Although she's not directly involved with the business, his wife is a huge supporter. He also had an uncle who was a mentor for him.

“I always say that everybody needs somebody to look up to, somebody mentoring them,” He said.

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Regardless of what level someone is at, Jay believes they need three things: Someone to mentor them, people in their peer group and someone to mentor.

“If you have those things, which I have fortunately had for a long time, it just makes you keep growing,” Jay said. “It also allows you to pour back into other people and help them grow. It just keeps the cycle of life moving forward.”

Growing a team

Jay’s career hasn’t been without challenges. One of the biggest was growing a team.

“I operated by myself for a long time,” Jay said.

For a while, he split up work among contractors, but as the economy started to collapse during the recession, he decided it was time to create a job for someone.

“Now we have a team of 15 people and a bunch of contractors,” Jay said.

He said it was scary – he can be a control freak and learning to delegate was difficult. However, he said, it’s the only way to grow and improve.

“It’s the big difference between owning a job and owning a business,” Jay said. “I always say a lot of people don’t really own a business – they own a job.”

A lot of times, he said, that job doesn’t pay well because the individual is probably working or thinking about their business 24 hours a day.

Skipping Vacations

In Jay’s case, growing a team meant vacations with his wife where he wasn’t checking his email or worrying about the company.

“I didn’t need to, because they’re perfectly capable of handling it without me,” Jay said. “But 10 years ago, that wasn’t true.”

He avoided vacations lasting more than a day or two because he was worried about what was happening at work. He had the mindset that he was the best person to get things done. Eventually, he realized it just wasn’t working anymore.

“It’s that mentality of like, if you want to get it done right, you’ve got to do it yourself,” Jay said. “And that’s just not true.”

Jay could do the job of anyone on his team – he’s done them all before. However, he admits he may not be able to do them as well as the people he’s hired. While he may be better than 80 percent of the population at photoshop, he can’t top his designers, for example.

It was a struggle, he said, learning how to let go and empower other people to take on responsibilities within the company – and to have the chance to fail.

“I always say one of my responsibilities as a leader is to put people in a place where they have the opportunity to fail – just not catastrophically,” Jay said.

While he protects his employees from major failures, he allows for “micro failures,” that encourage employees to learn from their mistakes.

“If I’m constantly swooping in and trying to save the day, which is a big mistake that I made for a long time, nobody gets a chance to grow,” Jay said. “That’s not fair.”

To learn more about Jay’s entrepreneurial journey, how he scaled his business and what he’s focusing on now, listen to the episode of The Thoughtful Entrepreneur above and don’t forget to subscribe on  Apple Podcasts Stitcher SpotifyGoogle Play Castbox TuneIn RSS.

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