The three greatest loves of Nicole Gregory’s career are marketing, real estate and building businesses — and she pursues them all with gusto.

Gregory is owner and CEO of Urban You, a Grand Rapids beauty bar and medical spa business with two locations; managing partner and CEO of Urban Lab Ventures, a Grand Rapids private equity firm; founder and lead investor of Pinchgig, a tech platform in development that will let beauty industry professionals rent chairs by the hour instead of monthly; owner and CEO of Customs House, a real estate development company in Marquette that is converting a former customs house for Canadian travelers into six luxury condos; and founder and minority owner of Organik Consulting, a digital marketing and communications business.

A native of Marquette and graduate of Northern Michigan University, where she earned a bachelor’s degree in marketing, Gregory moved to Los Angeles in 1994 to pursue an MBA in entrepreneurship from UCLA Anderson School of Management.

After earning her master’s, getting married and having five children, she stayed on the West Coast for 15 years, riding the “digital rodeo” as it left the gate.

With the experience she gained from starting her first business, an event coordination firm she developed during undergrad and sold just after, Gregory founded Big Time Media in Orange County in 1996. It was a web development startup before most people knew what that was.

“We built it from nothing to a substantial business in a handful of years,” Gregory said. “At that point, no one was doing that.”

Gregory said one of her strengths is finding gaps in the market. In the late ’90s, there was a huge need for back-end coders and systems thinkers.

Her mother — also an entrepreneur, along with her father and grandparents on both sides — made Gregory take a programming and coding class in the sixth grade. She “fell in love with it,” and it gave her the skills she needed more than a decade later to hire programmers at Big Time Media and work with them to plot not only a website’s structure but also the strategy behind what it should do for the client.

In 2001, Gregory sold the firm to a large Southern California advertising agency.

Next, she established Real Homes Realty, which brought the Orange County Association of Realtors’ multiple listing service online for the first time, giving clients the ability to browse real estate listings from anywhere. Despite the effort it took Gregory to convince the association it was the right direction to go in, the business saw almost instant success.

“We did $57 million in our first year because I was able to give people services they’d never had before, and that was integration from having to go to a realtor all the time just to look for things to being able to have it web-based. Now, it’s so commonplace. Then, no one even saw this gap,” she said.

“Having that technology background and growing up in real estate with my family, I’ve always had this love and passion for just building things or making things. I think it’s why I’ve made so many businesses over the years.”

Despite her growing success on the “bleeding edge” of the West Coast digital boom, Gregory felt the Mitten State calling her home about a decade ago.

“I realized, ‘You know, I have five kids. I want to find an opportunity to get closer to family as well as go back to a small-town environment.’ I love Marquette but did not want to go back there, and Grand Rapids seemed like the next big nice fit,” Gregory said. “It’s such an entrepreneurial town.”

The first business Gregory started in West Michigan was Organik Consulting in 2008, which assisted clients such as MC Sports, Steelcase and Baudville Brands with setting up budgets for digital marketing and doing strategy, campaign development and digital advertising.

She sold the majority stake to a Detroit company recently when she felt it was time for the next thing.

Beyond her desire to live in her home state, Gregory also wanted to use her success to invest in other businesses.

“There’s a lot of venture capital money that’s on the east side of the state, and that has started to come here, as well,” she said. “They’re looking at this side of the state as (having) different opportunities. Over there, they’re really focused on auto. Over here, the money is definitely coming over (for other things).

“That was my attraction. It felt like the right fit.”

Using the proceeds from the sale of her various businesses, Gregory began investing in startups. By 2016, she made it official and formed Urban Lab Ventures to give her an avenue to continuously meet and invest in young entrepreneurs. Pinchgig is one of the investments she’s made through Urban Lab Ventures.

Gregory got the idea for the Urban You beauty bar several years ago while traveling when she noticed how hard it was to find salons that offered hair, brows, makeup, nails and medical spa services such as peels and dermaplaning facials, all in one location.

She and Urban You CFO Barbra Homier opened the first location at 3152 Peregrine Drive NE in Grand Rapids, near Knapp’s Corner, in May 2017 and the second location at 756 Wealthy St. SE in March 2018.

The pair are planning to open two more locations on the east side of the state in the next year.

In each of her businesses and through her volunteerism with Forest Hills Public Schools, Gregory said she believes her main job right now is to help others grow and develop.

“I had a lot of people in my past who have supported me. Moving here and knowing absolutely no one, there were so many people that were gracious enough to take time and introduce me to their people and show me opportunities I never would have had,” she said.

“Now, my job is to develop people in their relationships, whether it’s their own business or where they want to go in their career or their talent.”

She said much of that takes place via her role at Urban You, which has about 25 employees and still is growing.

But she also has people in her network ask her to mentor young people.

“I have a young girl I’m mentoring now, she’s in college and she’s so put together; I love her,” Gregory said. “But she has got to shake loose of that (fear of other people’s opinions). You’ve got to find your groove. Don’t worry about anyone else. … Stay in your lane.”

Gregory said she tells aspiring entrepreneurs not to take things too seriously — and to find a business idea they’re passionate about so that when times get tough, they won’t be tempted to walk away.

She also said it’s important for entrepreneurs to accept the inevitability of occasional failure.

“The reality is you’re going to fail if you’re going to be a serial entrepreneur,” Gregory said. “I’ve had a lot of failures within different things. Just be OK with failure and learn from it every time.

“Be flexible, because not everything is going to turn out. Be able to shift/change. Be able to say, ‘This is not working, here’s what we should be doing; let’s go over here.’”

Gregory said even after 20-plus years of hard work, her passion for entrepreneurship remains strong.

“I love it,” she said. “I wake up every day excited about the next. I say everyone should try it.”