A Cape Cod native eyeing a real estate career ever since he built his first treehouse, Jack Cotton spent more than three decades building a successful brokerage in Osterville with a focus on second homes. Now, he’s aiming to share his secrets of success in the high-end, luxury home market with a wider audience. He’s written three books on the sector in less than two years, two for consumers and one for agents.
Jack Cotton
Title: Agent, Sotheby’s International Realty; Osterville
Age: 57
Experience: 36 years
How did you get started in real estate?
I started in my dorm room. It started off as John Cotton Jr. Real Estate, and then it became Jack Cotton Real Estate and then Cotton Real Estate. Then, in 2005, I sold to Sotheby’s. My father was in the plumbing supply business, and he had a warehouse. I had a little gray metal desk in the corner, where I had free rent. It was pretty pathetic. I used to make my own signs.
Out of what?
Masonite. Understand, there was no Internet. There was no such thing as a copy machine – the first high-tech thing was liftoff tape, for the old IBM typewriter. I was doing a lot of direct mail – 100 letters a night was my goal – and lift-off tape, as opposed to strike-over, to me it was unbelievable.
What made you decide to write a book?
People here tend to be more high-end. But even if you’re buying a $200,000 house on the Cape to be your second home, you’re still up there in the top 5 percent of income earners, because it’s your second house. These people are used to dealing with experts. So to me, writing matters.
The idea of a book has always been kicking around in my head. I wrote a book five years ago that got published by accident. When my dog died, I wrote a book for my kids; a publisher got hold of it, one thing led to another and they sent me an advance and a contract – I wasn’t even trying to publish it and it got published, so then I got sort of the bug…. It connected with so many people. People were like, “aw, I like this guy, I want to have him sell my house.” And I thought, if a dog book could do this, what could a real estate book do? So I did three in the last 18 months.
The past couple years have been tough ones for the real estate market. Why write about the luxury market? What lessons does it have to offer?
It really bothered me [during the boom]…. Watching these ads on TV, advising people to turn their homes into ATM machines, it would get me so angry. “Oh, it’s so easy, get money for a boat, get money for a car.” Real estate is the best investment in the world, it really is – if you follow the rules. It’s not a short-term investment. Your house is not an ATM. You’re supposed to make a down payment, and you’re supposed to pay it off. People had just [gotten] away from that. So the 12 secrets from a luxury homebuyer book, I felt was timely. Really, you buy a house with a long-term horizon, you buy with a fixed-rate loan, and you pay it off sooner. Even if it’s $100 a month or $100 a year extra towards the principal, you get the mortgage gone… the book is designed to teach the average person, bring them back to the basics of real estate.
One of your other books is aimed at the agent audience. What was your goal when speaking to them?
There’s 1.3 million Realtors, and most of them sit on the sidelines of the luxury home market, thinking that you have to be born rich and well-connected to succeed. And it certainly helps if you are. There’s people way more successful than me, but when I look back at where I started, I feel like it’s a miracle. And so I feel like, if I can do it, you can do it. So I’m happy to help them do it. It’s part of the obligation.
Cotton’s Top 5 Tips For Dealing With High-Net-Worth Clients
- Cultivate an expertise.
- Market that expertise.
- Become a trusted advisor.
- When negotiating, detach from the outcome.
- Don’t assume you know what the other person wants.





