Connect
To Top

Meet Thomas Edwards of The Professional Wingman

Today we’d like to introduce you to Thomas Edwards.

Thanks for sharing your story with us Thomas. So, let’s start at the beginning and we can move on from there.
I was a sophomore in college and was dating my girlfriend for over two years. I thought I found The One and she was an amazing person. I went as far as asking her parents for their blessing, which they gave to me.

A week later, I got a phone call from my girlfriend, thinking we were going to talk about her staying at my place for the weekend. Eventually, she came out and told me she cheated on me with some random dude she met in her class. Everything that I had planned for my life was up in smoke.

So I did a little more soul searching. One day, I came across a book called Seven Habits of Highly Effective People by Stephen Covey and it changed my life. I began to understand the standards I needed to uphold for myself and others. It helped me change how I should be interacting and communicating with people and the goals I wanted to accomplish.

So I did a ton of reading and read books on communication, fitness, nutrition, fashion, style, sex, relationships, networking, test taking, interviewing, public speaking — anything that I could get my hands on that I thought was going to be effective and beneficial for my life. My brain was a sponge for the next two and a half years.

I went through a rollercoaster of progress for the duration of college and then when I graduated, I started a blog to really chronicle my development and hold myself accountable. My blog was geared towards that and my first experiment was what I called “30 in 30.” This experiment pushed me to go to 30 bars for 30 consecutive nights. Needless to say, I had many lonely nights but anytime I went to the bar, I had just one objective. I’d go, chat up the bartender, order a drink, and whoever I sat or stood next to, I’d chat up. It didn’t matter if it was a guy or girl, I just wanted to get comfortable talking to random people. It was certainly a struggle as many interactions didn’t pan out well but I eventually became more comfortable putting myself out there and I ended up having great interactions with people who soon later became my friends.

My tipping point (cue Malcolm Gladwell) was when I got into a relationship with someone who was 19 years older than me. I was 23 at the time, she was 42 and when I blogged about my experience, my readers resonated with that. It was surprising to see how many people were really drawn to that particular experience and that was the beginning of my credibility that would allow people to ask me for advice based on my experiences.

Inspired by a friend, I decided to go to South by Southwest, an interactive conference in Austin, Texas, to try to discover a way to monetize my passion for personal development. I was meeting so many people, looking for that idea, not knowing that the idea would hit me at a place where my own journey began — the bar.

While I was with good buddy of mine, he saw a really gorgeous woman at the bar and wanted me go over there, chat her up, and then introduce them so they could go out on a date. I thought he was joking until he offered to pay for my drinks for the rest of the weekend. So I walked over, chatted her up, introduced them and “went to the bathroom.” When I came back, I saw him getting her number and the following day, he texted me saying he had a great lunch date with her and to let him know where I was that night because drinks were on him, ending the text with, “thanks for being my wingman.”

And that was when it hit me. It’s one thing to facilitate introductions but I knew there was value in teaching others how to do it on their own. I loved that he called me a wingman so, like an athlete, I figured it’d be cool to “go pro” and become a professional wingman. That was the moment The Professional Wingman® was born.

And to this day, my mission is the same. I want people to know they can trust someone who’s been where they’ve been, in making sure they don’t have to be alone on this journey, and what took me several years to figure out can take them much less time with my fresh, authentic perspective and guidance.

Today, we’ve given advice to thousands of clients from all around the world and are responsible for over 100 people getting engaged and married, with over a dozen of them having kids.

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
It’s never smooth for a then-22-year old to proclaim themselves capable of helping others find love. Earn credibility was probably the hardest thing to generate. After that, it was getting a steady flow of clients. Once those two eventually came together, it was structuring my pricing model that proved to be the most challenging, and in fact, it’s still something we tinker with when we’re able to find ways to give more value to our clients. Getting press was fortunately not as difficult as it may be for others but I was always a fun story. It took a very long time before I was seen as the go-to expert in dating, sex, and relationships.

Alright – so let’s talk business. Tell us about The Professional Wingman – what should we know?
We focus on helping professional singles improve their relationships by developing their social skills through experiential coaching. How we do this is by going out with our clients, acting as their wingman, and giving them real-time feedback on what prevents them from making romantic connections happen. I’m a recognized authority on dating, social skills development, and lifestyle strategy, so peers, colleagues, and media have deemed me, the “real-life Hitch.” It’s cool to say we have over 100 people married and over a dozen kids as a result of the work we’ve done, but we’re most proud of the life-changing effects we’re able to give people, who at one point or another, felt helpless before working with us.

Any shoutouts? Who else deserves credit in this story – who has played a meaningful role?
There were (and still are) a lot of people who I can thank for the success of my business, but the first person was entrepreneur, Gary Vaynerchuk, who let me stay in his hotel room while I was at SXSW. When I told him about The Professional Wingman, he basically said, “if there’s anyone who can pull it off, it’s you.” That was all the validation I needed. He helped a ton by teaching me about branding and content strategy. I have a lot to thank him for.

When I was living in Boston, I met a guy named David Gerzof Richard, who runs a tech PR firm out of Brookline, and he taught me a ton about image and the importance of building relationships within the industry. To this day, he’s been great with helping me brainstorm new ideas, introducing me to other influencers, and letting me know if I’m making good decisions with the direction of the company.

Contact Info:

Getting in touch: BostonVoyager is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

Leave a Reply

Your email address will not be published. Required fields are marked *

More in