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Making the Match



With more than 16 years of experience as an executive and personal assistant, Catherine Brown knows the job entails more than people think it does.

“There is still a bit of this stigma, a lackey mentality, of being second best,” she says. “When in actuality, if you ask any powerful person in any capacity, you’d find that their admin is the person they cannot live without.”

But finding that trusted support person isn’t always easy. That’s why Naples-based Brown started Entourage Managers (EM), a matchmaking service that uses personality profiling to connect executives with compatible assistants. “I have that personality of being a caretaker or nurturer,” says Brown, “so I love nurturing other people’s success.”

The Idea

Brown started her career at age 15, working as an assistant to her grandmother, a presidential advisor on drug policy. She served as an assistant on Capitol Hill during college and went on to work for a slew of high-profile people, including a vice president at SpaceX.

It was while finding him a new assistant after he relocated that she started thinking about a matchmaking solution. “I’m not a PhD in organizational behavior or human resources,” she says. “But I am someone who is very skilled at her job and has insights into what it takes to have this relationship be powerful and synergetic.”

Getting accepted into the Women’s Startup Lab Accelerator in Silicon Valley helped her further develop her idea. While there she learned about Growth Resources Indicators and its workplace assessment tools. It took Brown time to convince GRI that its personality profiling could be used for successfully matching assistants with executives, but she’s proven her idea enough to wind up with a contract with the firm.

The Launch

Brown admits that working in the tech space came with a steep learning curve. She sought out help where needed. “I think that’s the most critical part of building a business: Know what you don’t know, and then get people who know what you don’t know,” she says.

Her online survey takes “11 minutes, tops,” and is designed with executives’ busy schedules in mind. Brown then applies what she calls her “Spidey sense” or “special sauce” to the survey results to recommend compatible pairings.

Blogging and networking have helped Brown get referrals, grow her client list, and land a meeting with Silicon Valley consultant Ryan Keating. Brown thought she was finding him an assistant, but he wanted to talk about her process. He has since joined EM’s management team. “He said this industry is something that’s ready to be disrupted and revolutionized, and he thought I had what it took to do it,” she says.

What's Next

Keating is helping Brown seek investors for EM. “We have a product, we’re using it, we have traction and a full team built out, so we’re definitely in a good position for funding,” says Brown, who’s made about 80 matches so far. “Funding would help us grow bigger, hire more people, analyze more data, and achieve scale quicker.”

To this point, Brown has “bootstrapped” everything. “I’ve eBay-ed the hell out of my closet; I was ghost writing a book. You name it, I’ve done it,” she says.

She’s also looking into a licensing model for her platform. And while she splits her time between Silicon Valley and Naples, she has no intention of saying goodbye to Southwest Florida.

“The Valley pushes you into unrealistic and impossible games,” she says. “Being in Naples keeps me grounded and keeps my vision focused.”

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