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Meet Cushman & Wakefield’s Michael O’Leary

Michael o'Leary Boston, Michael o'Leary Cushman,

Michael O’Leary is a Managing Director for Cushman & Wakefield’s Brokerage team in Boston. He focuses his efforts in the Route 128 Central market representing both tenants and landlords.

How did you get started in the industry?

After graduating college and a brief two-year stint of professional hockey in Germany, I came home and started my “journey” of trying to find a job. I met with as many people as possible, and it was after my first meeting with someone in the real estate business (Tom O’Regan – when he was previously at Cushman & Wakefield 15 years ago) – that I set my sights and focus on getting into the business.

As anyone in this business knows – it took a while. After meeting with 84 professionals at 14 different real estate companies – I began my career on March 17, 2003 (St. Patrick’s Day).

Did living in another country widen your perspective on things?

Most definitely. Being able to live in another country completely on your own forces you to have to figure things out. It was definitely a “life experience” that taught me how to overcome simple language and cultural barriers, but also (to put it candidly), forced me to grow up quickly.

I know fishing is one of your biggest hobbies. What’s the biggest fish you’ve caught (and do you have photographic evidence)? How has fishing become a big part of your family life?

Fishing is something that has been part of my life since I was born. Most summer weekends were spent on the boat with my father catching whatever we could in Cape Cod Bay (typically striped bass, bluefish, flounder, etc.). It was a ton of fun, and something that I’ve already instilled in all my children – the love for the water and fishing.

However, now I chase slightly larger fish. For the past 15 years, most of my fishing trips are spent chasing Atlantic Bluefin Tuna. The largest fish I have landed (and sold) was a 797 pound Bluefin, which I caught two summers ago. Plenty of photographic evidence of that!!!!

While that may be the largest fish I’ve recently caught – the single best day of fishing that I have ever had was this past summer. I took my two sons out for a quick striped bass trip. Cam (my six year old) landed his first bass – taped out at 38” and 24 pounds – then Tanner (my four year old) “landed” (with a little help from dad) a behemoth 46” bass that weighed in at 38 pounds. They’ll both be making their inaugural tuna trip in no time, and Brooke (my two year old daughter) will be right behind them.

How would you describe your approach as a real estate broker? What makes you successful?

First, any success I’ve had in this business has less to do with me and more to do with the members of my team and with whom I’ve had the opportunity to work with. I’m very lucky to sit in the seat I’m in and any success I’ve had is a direct result of the above. I’ve been lucky enough to have surrounded myself with some very talented and experienced colleagues who have helped pave the way for the “younger generation” to rise up the ranks and flourish.

If I had to pinpoint one trait that makes me successful, I would say it’s my work ethic. Working hard is not just about being the first one in and the last to leave (although I do think that’s important), but rather it’s about being consistently present and striving to get better. If you are able to do this, then you can create your own luck (rather than just getting lucky) and work through complexities one of your clients might be facing.

Another trait that has led to success (I think) is that I am a good listener. So many times in our business this gets overlooked. To have the ability to listen to a prospects needs or a client’s challenge, think about it, then speak and offer a solution, I feel is a trait of success.

However, as I mentioned before, it’s all about the team and the collective strength – that brings success to anyone in a position like mine.

How has that approach been reflected in the team’s recent wins?

Our biggest recent win by far was at The District Burlington, where we were named the exclusive leasing agent this past January. When you’re up against some significant players in the industry with a tremendous amount of experience and you win, that’s powerful.

We felt like the underdog going in, but had the opportunity to have several “side-bar” discussions with ownership leading up to the presentation and listened to what their challenges and issues were. We took an aggressive approach in our marketing message, which ended up really resonating with the developer and its partners.

It’s the largest exclusive listing that’s changed hands in the last five years in the suburban market, and since taking over early this year, we’ve leased roughly 150,000 square feet of space there.

How have your experiences evolved into how you help mentor younger team members?

I had very strong mentors when I joined Trammell Crow Company 11 years ago – all of whom I work directly with still today – and candidly still provide me mentorship, and in some respects now, I think I provide them some too.

More often than not in our business, you see some talented younger professionals get an opportunity, and fail. It’s tough to see. On our team, when we hire a younger associate, we strive to provide them an organized framework over the course of 12-24 months – to listen and learn. We immerse them in the market (they need to know the “field they will farm”), get them involved in all projects and transactions, and slowly let them spread their wings. We feel that a bird flying in the right direction will have more success versus a bird flying in circles with a wing clipped.

Other than family and your career, what are you most proud of?

That’s a really difficult question – because at this point in my life, with three active children under the age of six and a career that I want to continue to grow successfully – there isn’t a tremendous of time or bandwidth for much else.

So if I have to single out any one thing, I think it would be the relationships I’ve been able to develop – with my family, friends, colleagues, and clients. That’s what really makes this special.


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