Sometimes, you have to try new things and take a few risks to discover where you truly fit. Sticking with what you know is easy, but exploring the unknown helped me learn the true range of skills I had and where I could best use them to help others.

 

For a long time, I chose a traditional career path. I went to college, then business school, and ended up working in IT, first at Oracle, then Microsoft. As a people person, I found my niche in customer success, helping clients better understand and adopt software after purchase. I genuinely enjoyed solving problems, connecting with people, and making their lives easier. 

 

But I had another passion on the side: real estate.

 

My first project was renting out my own apartment in Harvard Square as an Airbnb. I painted it, sourced beautiful secondhand furniture, and styled it to feel like a high-end hotel on a shoestring budget. When it was booked, I’d pack a bag and stay at my parents’ house nearby. That’s when I realized I had a real eye for design and an instinct for spotting potential in a space. 

 

From there, I turned it into a part-time job, helping other people stage and prep their homes, and eventually moved into flipping projects, learning how smart updates and repairs could unlock significant value in a home. In IT, I had done product design, marketing, and even had my own startup that I sold. And, in college, I studied art history. So, I had a unique blend of practical operations skills and an eye for design. 

 

Then COVID hit, and like many people, I started rethinking what I truly wanted. That traditional path I had been following suddenly didn’t feel like the only option. Then, Redfin reached out. They were a tech company that does real estate, so it was a natural fit and gave me the final push to go full time. That decision changed everything.

 

From day one, my approach to real estate was different. I had already developed a strong creative eye, a solid understanding of repairs and design, and a knack for problem-solving when unexpected things popped up. I never just list a home and hope for the best. I sit down with my sellers and walk them through a clear, strategic plan. Do we clean and stage? Do lighting updates? Price it as-is and go to market fast? I break it all down, show them potential outcomes, and help them choose what’s best for their timeline and goals. 

 

One of the unique things I do is offer to cover the upfront costs for these projects and get reimbursed on the backend when the deal closes. Why? Because it removes the financial burden from my clients and pays off every single time. It’s as easy as handing me the keys and letting me take care of the rest!

 

And for buyers, those same skills and resources are just as valuable. If the home needs a little love, whether it’s adding a bathroom, updating the kitchen, or reimagining the layout, I already have a trusted team ready to help. I’ll coordinate the entire project so they don’t have to lift a finger.

 

The details and thoughtful touches really do make a difference. I’ve set up Wi-Fi routers and changed air filters for families with newborns before they move in. I think about all the little things that go into moving into a home and try to remove as much stress as I can by staying 10 steps ahead. 

 

That level of service creates real trust and leads to lasting relationships. I’ve been invited to birthdays and weddings, and those moments remind me that this work isn’t just about buying and selling houses. It’s about helping people start new chapters of their lives and align their home with their lifestyle and priorities.

 

Real estate has completely changed my life, and I’m truly grateful to do what I love every day. I get to bring all parts of myself to the table: business, creativity, and service to others.

 

When I’m not working with clients, you’ll probably find me at CrossFit, running charity 5Ks, or squeezing in a Little League game to cheer on my nephews before an open house. I also love going to local indie coffee shops, finding the best spots I can recommend to people, and working on my own home projects.

 

I’m a big believer that life is about service. And I’ve carried that belief into everything I do. Whether it’s teaching newer agents the ropes, checking in with past clients, or going the extra mile on a listing, I’m always thinking: how can I make this easier, better, or more thoughtful? This business has never just been about transactions for me, it’s about people, life transitions, and finding and creating spaces that people are excited to call home. There is a lot of strategy and hard work behind every deal. I’ve studied negotiation formally, sold over $125 million in real estate, and built this business by being thorough, honest, and creative. You won’t just get a sign in the yard, you’ll get a full-service experience that’s thoughtful, strategic, and actually enjoyable!

 

Sincerely,

 

 

Robert Leahey, Jr., MBA

Real Estate Agent

Call/Text 617.640.0409

robleaheyjr@greaterbostonunlocked.com

GreaterBostonUnlocked.com