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“I Want To Bet On Me” – The Story of Kelly’s Decision to Get Into Real Estate

This is the story I’ve told dozens of times over the years about my wife Kelly’s decision to get into real-estate. It’s a love letter, a tribute, and simply a life-affirming story about a good person who achieves success through hard work and courage.

Kelly Gaitten Real Estate Agent Leesburg

Kelly helped me buy my first home in Leesburg before we got married. This is how I knew she belonged in real-estate.

To know and understand Kelly, it would be helpful for you to have seen her favorite movie, The Devil Wears Prada. The 2006 film stars Anne Hathaway as the “plucky” executive assistant Andrea Sachs who caters to the every whim of fashion executive Miranda Priestly, epically portrayed by Meryl Streep. Even I confess to enjoying Streep’s incomparable performance as the absurdly demanding, high-powered fashion executive from

Hell. But I think for Kelly, the movie is much more relatable and aspirational. You need to know that when Kelly watches this movie and we get to the part where Anne Hathaway’s character improbably obtains an as yet unpublished manuscript of the next Harry Potter book at the whim of her boss, there is a part of her that yearns for such an impossible challenge. And there’s a fierce confidence in her heart that say, “I could have done that too.”

See for much of Kelly’s early professional life, she worked in administrative roles like the one Anne Hathaway’s character stumbles into in The Devil Wears Prada. By the time I met Kelly in 1998, she was the Executive Assistant to a real-life, high-powered female executive at then high-flying America Online, the fastest growing technology company in the world.

One of Kelly's first professional head shots.

One of Kelly’s first professional head shots.

Kelly was an ace as an executive assistant. She was smart, personable, resourceful, cheerful and one of those people who clearly takes joy from anticipating and fulfilling the needs of others. Oh by the way, she was also gorgeous, a happenstance that opened doors and made half the population more than happy to help her get just about anything done.

At AOL, Kelly thrived in that Executive Administrative role. She was in high demand amongst the big wig technology executives. She had the right look and a strong reputation as somebody who could get things done at any level across one of the most powerful companies on the planet.

Around 2001, the executive that Kelly was supporting at AOL left the company suddenly. She received a flurry of inquiries about her status. There was a long line of EVPs, SVPs and even C-level executives who were eager to acquire one of the most-liked and most-accomplished assistants in the company. Having Kelly as your assistant was not just a good hire, but a status symbol and a virtual guarantee of smooth daily operations. Kelly was at a crossroads. She also needed to make a good decision about partnering with an executive who would advance her career.

For months and years before this decision point, it had occurred to me that Kelly might be very successful pursuing one of the career paths she had explored earlier in life. Back in the 1990s she had studied for and gotten her license as a real-estate agent. She never did anything with it, and the license had long since expired. But I could see that people loved Kelly and trusted her with the most important details of their lives. She was somebody who could get things done. And it seemed somewhat obvious to me that she could be successful as a real estate agent if she wanted to be.

I confess that my interest in having Kelly reconsider a career in real-estate was at least 50% selfish. I thought that if she were relieved of the burden of worrying about the 24×7 needs of globe-travelling technology executives, she might have more time to spend on spoiling me. I thought she might make a modest living, but have the flexibility to get my dry-cleaning every time and put dinner on the table at a regular hour most days. To be fair, there was just some prescient instinct in me that knew she would be successful and fulfilled. But I admit to mixed motives.

So, in recent months I had regularly advocated that Kelly get back into real-estate. It was a hard sell. Her number one objection was the notion of losing her weekends. I thought that was silly and argued that giving up time on Saturday & Sunday would be fully offset by less demands throughout the week. I of course had no idea what I was talking about or where this was headed.

she-can-have-a-pony-riderIn the Spring of 2003, Kelly and I were home a hanging around out on the back deck. She needed to make a decision about choosing a new executive to support or making the jump back into real estate. I had an opinion, but I genuinely wanted her to have the freedom to make either choice. We were living within our means, had some savings and could get by for awhile without her salary. We both assumed that my career and my income would pay most of the bills. It was time to make a choice.

I remember the moment with enormous clarity. It was a pleasant Spring evening. We were sitting at a little bistro table on our back patio. Kelly was having a glass of wine. The dogs were running around the backyard. We took a quiet moment to chart our future. I put it to her as directly as I could and asked the question that would change our lives forever. I said, “Do you want to be somebody’s secretary for the rest of your life, or do you want to bet on yourself and try to run your own business?”

Kelly paused and really thought about it. She furrowed her brow, I could see her brain process about a million different scenarios over the next 20 seconds. She looked up and I will never ever forget the instant she looked me in the eye and said, “I want to bet on me”.

I believe this is a picture from the actual evening of the famous "I Want To Bet On Me" conversation.

I believe this is a picture from the actual evening of the famous “I Want To Bet On Me” conversation.

It was a nice moment between husband and wife. I think we hugged. The sun set, we rounded up the dogs and went in the house, we probably watched television for a couple of hours and went to bed. A decision had been made. I was proud of her and I like to think she appreciated my faith in her.

If this were a movie, it would be the perfect time for a montage. Starting before sunrise the next day, Kelly the secretary set about the business of becoming a real estate agent. She began weeks of intense studying for what seemed like an endless number of licensures and certifications. I went to work every day and came  home to find her just plugging away. The little room off the kitchen slowly transformed into a real office where Kelly was building mountains of books and paperwork.

Another thing started during this time period. Kelly was on the phone a lot. I rarely paid attention, and tried to tune out the noise of her real-estate conversations. But after a few months, Kelly was on the phone constantly. Wherever I was in the house, she was on the phone, advising, inquiring, following-up, reaching out and getting things done. So began many, many years of hearing half of the conversation about every intricacy of a real estate transaction.

I mostly ignored her. Frankly, I was not ready to take Kelly seriously as a real estate agent just yet. I expected to cringe hearing her give friends and family members advice on half-million dollar transactions.

kellys-awards-for-2015I don’t know which transaction it was, but it must have been one of the hard ones. Kelly was on the phone all night putting a deal together. She was probably on the phone with the buyers, the seller’s agent, the title company, the lender, the contractor, the town, the broker, etc. etc. I started to listen to her put this deal together, selling, advising, negotiating, etc. The girl was good on the phone. She was confident, articulate, smart, thoughtful and caring. I was seriously impressed and I told her so.

Kelly did $10 million dollars in volume by herself that first year, with little experience, no network and damn little help from me. There would be ups and downs and failed deals over the years, but even during the market crash from 2007-2012, Kelly kept producing and kept investing in her business.


In 2008, I left AOL and was making good money at a technology start-up in Reston, Virginia. I think that was the first year that Kelly’s income matched mine. I brushed off that potential bruise to my ego, noted that she had a lot of expenses that I didn’t, and continued to consider myself the breadwinner in the family.kelly-gaitten-on-the-cover-of-top-agent-magazine

The next year Kelly doubled my income. The following year she tripled my income. She’s gone on to be the top listing agent, top seller and top producer in her office 9 years in a row. She’s been among the top 3 agents nationally at Berkshire Hatahway PenFed for the past several years. Kelly’s been featured on the cover of magazines like Top Agent and twice has been honored as one of the Top 100 Agents in the DC Metro Area by Washingtonian Magazine. There are too many awards and accolades to list.

So, the moral of the story? Well, for one thing, when you choose Kelly as your real estate agent, you’re not just signing up to do business with one of the most competent and successful agents in the world. You’re also validating the American Dream. You’re part of the story of the humble secretary and house wife who built a business with her bare hands, and still kept cranking out the laundry.

It’s been a privilege and a wonder to witness. Kelly’s transformation from Trophy Bride to Sugar Momma has been humbling and gratifying. Her ads are playing on the radio. Her face was on the cover of a magazine in the waiting room at my doctor’s office the other day. On a job interview a couple of years ago, the interviewer stopped our conversation to say, “We figured out who you are. You’re Kelly Gaitten’s husband, right?”

On behalf of Kelly, I’d like to offer our sincere thanks to every one of Kelly’s clients, as well as the dozens of individuals who have helped her build this business. It’s the army of friends, family, colleagues and supporters who continue to help her write an amazing life story. I know that Kelly hopes that she has provided valuable service to every one of her clients and genuinely wants everyone she knows to “Love Where You Live”.

Steve Gaitten About Steve Gaitten
Steve Gaitten is an accomplished marketing and technology executive with more than 20 years of experience. His diverse background includes success in a broad range of verticals, including financial services, education, enterprise software, Federal IT and consumer Internet services.

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