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The power couple taking turns making millions

The Callahans' latest venture is headed to top $1 million in annual revenue this year.

Kevin and Maggie Callahan are wedded to each other — and success.

In the world of start-up entrepreneurs, the Callahans qualify as a power couple. Kevin co-founded a business that sold for $150 million, and Maggie's latest venture has attracted the attention of a key platform of Oprah Winfrey's media empire.

As partners in life and business, the Callahans are generating millions. Here are seven key lessons they have learned while pursuing their dreams.

Kevin and Maggie Callahan in Paris
Source: One And Only Paris Photography
Kevin and Maggie Callahan in Paris

1. Sometimes you have to do what they tell you never to do.

Kevin founded MapMyRun (which was later folded into MapMyFitness, where he served as co-founder) to help people get healthy and train effectively by mapping, tracking and pacing runs. Maggie, Kevin's girlfriend at the time, was the breadwinner in the relationship through her corporate law job and, later, a start-up based in San Francisco.

There were times of doubt for the Austin-based Callahans — strict grocery budgets, countless 20-hour days, feeling like they didn't know the end game — but the riskiest financial move of all in supporting Kevin's business, the one most experts would advise against, paid off in the end: Maggie liquidated her 401(k) to help fund the fitness app.

"Everything they tell you not to do, we did," said Maggie.


2. It's a lot easier to plan for your passion if you have a steady income stream.

Once MapMyFitness started to show strong growth and revenue, Maggie was able to start pursuing her dreams.

She dabbled in start-ups but eventually went to culinary school in Austin. It was the combination of her start-up experience and passion for creating fine edibles that led Maggie to create Maggie Louise Confections, a company that brings haute couture design to the world of chocolate.

In December 2013, Under Armour bought MapMyFitness for $150 million to build its wearable fitness lab. After the sale, the tables turned: Maggie went from supporting Kevin financially and emotionally to being the one to follow her dream of building a business. Kevin invested his share of the proceeds from the Under Armour acquisition in Maggie's business. The MapMyFitness payday helped scale and self-fund Maggie's new venture and provided the Callahans with the experience of one successful start-up under their belt.


Maggie Callahan in the Austin, Texas, Maggie Louise Confections’ showroom
Source: Wynn Myers
Maggie Callahan in the Austin, Texas, Maggie Louise Confections’ showroom
"Everything they tell you not to do, we did." -Maggie Callahan, CEO and founder of Maggie Louise Confections


3. Even if you're local, think big and be willing to pay for it.

Maggie set out to change the way people gave gifts and experienced chocolate with her custom designs, and a turning point came in 2014 when Maggie Louise Confections made the "Oprah's Favorite Things" holiday edition magazine.

"It gave us an incredible amount of credibility and helped us sell nationally to people who had never met us before," said Maggie, CEO and founder of the company.

But it wasn't luck that got the attention of Oprah's publication. Maggie Louise Confections hired a nationally focused public relations firm to help market the product beyond the local marketplace. A great product is essential, though. "You can hire the best PR team in the world, but if you don't have a great product, then it doesn't matter," she said.

Now, with corporate clients like Jimmy Choo, Sephora, John Frieda, QVC, Neiman Marcus and Saks Fifth Avenue, Maggie Louise Confections has grown its client base 500 percent year-over-year, with 30 percent of its business coming from custom orders.

4. A long-term goal is not enough.

Maggie and Kevin, now COO of Maggie Louise Confections, said one important lesson from the success of MapMyFitness was multiple goal-setting.

"Set goals for the day, year and five years ahead, and constantly think about how to get there. We dream big," said Kevin.

Kevin and Maggie's goal is to grow Maggie Louise Confections far bigger than MapMyFitness.

5. Know what each other is good at, and stick to it.

"We don't govern by consensus," said Kevin. In his role as COO, Kevin applies his technology background to modernize the otherwise antiquated manufacturing world of chocolate and to optimize the customer experience. He analyzes data every day to make the most informed business decisions possible. But he claims that Maggie "makes the final call," drawing on her years as a corporate lawyer and experience building other start-ups.

Bringing haute couture designs to sweets: Maggie Louise Confections’ Spring Beauty Chocolates collection.
Source: Skorpil Photography
Bringing haute couture designs to sweets: Maggie Louise Confections’ Spring Beauty Chocolates collection.


6. If you ever forget this, your business is finished: The customer truly is king.

Maggie and Kevin stress the importance of the customer experience. MapMyFitness engaged consumers to care about their health and enjoy the experience of getting fit, while Maggie Louise Confections aims to delight each customer when they open the creative gift box and taste the handmade chocolate.

"One hundred percent of our company and brand is about the client experience," Maggie said. "Every touch point needs to be special. ... Before they open the box, we want them to be awed and excited."

7. Life doesn't get in the way of success; it enhances it.

Both entrepreneurs love the feeling of centering their lives around the companies they are passionate about, whether it's buying a house nearby so they can walk to work or simply having the feeling of being "all in, every day," as they put it.

And soon the Callahans' life is going to get a little sweeter: Maggie and Kevin are expecting their second child.

Maggie said being pregnant while running a start-up was the best thing that could've happened to her. Pregnancy planning taught her that she needed to have in place a trustworthy team who could run the business when she wasn't 100 percent available. "It helped me build a better company," Maggie said.

With 350 percent revenue growth year-over-year, the Callahans now have the team in place for Maggie Louise Confections to surpass the $1 million annual revenue mark this year.