Out East End: Tom and Mickey on Merging Real Estate and Music

It’s hard to imagine Tom and Mickey — Tom Postilio and Mickey Conlon — ever being anything but Tom and Mickey.

Partners in life and in business, the married, dynamic duo is a top-producing real estate team at Douglas Elliman in Manhattan and on Long Island, consistently ranking nationally for sales volume.

“I always get top billing,” chides Tom, who once starred in Our Sinatra Off Broadway and sang with big bands and at venues such as Westbury Music Fair and the Rainbow Room in Manhattan.

“It was my design — Tom and Mickey, you know, it was sing-song,” Tom adds with a laugh.

“Oh yes, that was it,” confirms Mickey, who can more than hold his own with a tune and who was producing commercial theater in New York before he decided to resurrect his real estate career when the world was financially rocky in the fall of 2008.

Music has always played an important part in their lives.

As their “how we met” story goes, Mickey had Tom at Frank Sinatra. Or was it at Marilyn Maye, the cabaret star who both Tom and Mickey adored and who they were both going to see perform at the Town Hall in Manhattan in January of 2008 on a classic New York night. Their mutual friend Mark Sendroff introduced them outside, under the marquee, just before Maye was about to hit the stage. And the rest is …. Tom and Mickey history.

“Music matters to us because it was music that brought us together,” says Mickey. Once Mickey revealed his mutual appreciation of Peter Allen, that pretty much cemented the deal with Tom.

“Peter Allen: That was when I truly fell in love,” says Tom. “I’m nuts for Sinatra. He was my original hero (Mickey’s hero is Noel Coward), but when I was 14 Peter Allen made a difference in my life.”

Mickey adds: “Peter Allen is the reason you came out.”

Tom replies: “Yes, Peter Allen is the reason I came out. I went to see him in concert in 1990 when I was 20 years old and I had not come out yet. I knew I was gay. I went with some friends to see Peter Allen at Westbury Music Fair, in the backyard practically where I grew up on Long Island — a packed house, standing ovations — it was unbelievable.

“Peter Allen was outrageous,” he continues. “I fell in love. I sat there in my little chair and I thought, ‘Wow, this guy is really gay?’ And he’s getting standing ovations from everybody in Long Island? So this is not a bad thing.”

The clincher for Tom was at the end of a Peter Allen song,

“Two years before he died, he sang the last song that he (co)wrote, ‘Love Don’t Need a Reason,’” he said. “Grammatically incorrect but … it just knocked the wind out of my sails. I was so taken. ‘Love Is Never A Crime’ and I sat there and I cried and I came out to my family the next day.”

Not an easy road at first for either Tom or Mickey when they respectively came out to their parents.

“My mother will say to this day that she was just afraid,” says Tom, “You know, the stigma of gay and AIDS and all of that in the late ’80s early ’90s, I don’t have to tell you, it was always like, ‘What will the family think, what will the neighbors think?’”

He is quick to add that today he is “so proud of my parents for changing their mind about this. And that’s what any of these issues is about — just making sure that you know it’s the same people you know, the same people you love and now you have a little more information about them.”

Mickey says, “That’s also why we need to say ‘gay.’”

Tom adds, “Harvey Milk: Come out, come out, come out.”

Challenging family dynamics aside, the Tom and Mickey moniker fit and dovetailed with their decision to combine forces.

“When we both kind of closed the previous chapter out, the business really started to do well,” says Tom, who had been working at a boutique firm in Manhattan, while Mickey was selling real estate at a different boutique firm on Long Island when the two decided to merge as a team.

But try as they did to focus primarily on real estate, show biz, clearly in both of their DNA makeup, circled back and played its part.

“I had started with Selling New York and was having great success with HGTV,” says Tom. “Selling New York was like the first reality real estate show, people stopped me on the street, people loved it.”

When Tom and Mickey became a thing in real estate, it worked for them as a team on the show as well.

“The success of that show was about the same time Mickey and I decided to work together and then there was just the two of us on the show,” says Tom. “From there, fast forward it was just a shot out of a cannon (2010). We did that for a couple of seasons.”

The appearances on Selling New York led to more TV appearances, and Tom and Mickey were sitting on a couch as guests of Andy Cohen.

“The show gave us a sense of familiarity with people, so when we sat down they had a sense of the way we worked,” says Mickey. “I don’t think we played characters on the show. We were pretty much who we are. I think it was an authentic representation.”

That same familiarity and ease with themselves and with people has certainly helped their business and their relationships. It’s no wonder they are often the go-to agents for celebrities and industry leaders. Their clientele includes Liza Minnelli, Barry Manilow, and David Sanborn.

“It’s all about people you know — referrals are the life blood of business,” says Tom. “If somebody had a good experience, then they tell somebody in their family or their sphere of influence, that truly makes us proud.”

In 2015, their real estate career took a big turn when Tom and Mickey “had the good fortune to meet Howard Lorber,” Douglas Elliman Real Estate chairman.

“Howard personally negotiated the deal with us to bring us to Douglas Elliman and we made the move. It’s been seven years now,” says Tom. “We felt like we had hit a ceiling in our career and carefully watched other colleagues who had made a move. Whether or not it’s true, somebody once said to us, ‘I think you guys are great, but I’d never hire you because you’re not with one of the big firms.’”

Tom and Mickey felt “there was a sense of accountability to that.” Adds Tom, “So we made that move and we flourished in the environment and we love the company so much … and Howard really plays an active role in the business and is always happy to be there.”

This summer, Tom and Mickey are partnering with Douglas Elliman to sponsor and bring back a music series they started last summer at The Jazz Loft in Stony Brook — a marriage of sorts with their real estate and their love of music, particularly jazz standards and music from the Great American Song Book.

On Saturday, August 13, acclaimed jazz guitarist and singer John Pizzarelli will perform a tribute to his late father Bucky Pizzarelli, the legendary jazz guitarist who inspired his career. On Saturday, September 24, celebrated singer-songwriter Peter Cincotti will enliven the Jazz Loft’s Great Lawn for a free concert that also coincides with the Seventh Annual Harbor Jazz Festival.

“We adore Stony Brook Village,” says Mickey. “It’s just picture perfect, quaint, sitting on the harbor, just the loveliest town and when we have guests coming to stay with us and we show them around — we always bring them to Stony Brook to walk around.”

The town is a stone’s throw from Nissequogue, where after spending many summers in the Hamptons and looking upstate and in Connecticut, Tom and Mickey bought their “dream (country) house” on the water in 2012.

“We really didn’t know much about it (The Jazz Loft),” says Mickey. A stroll through town with Tom and Mickey’s dear friends Michael Feinstein and Terrence Flannery prompted Feinstein to inquire about the venue.

“It’s a museum, it’s a cultural institution and when we finally got up to the performance space we just fell in love — we said, we need to do something here,” says Tom and Mickey, who love that the venue is about “jazz, about education, and it’s a not-for-profit.”

“Last year we had Marilyn Maye — she came out and did a weekend and we got her booked there for three nights … they went bananas! Completely sold out!” gushes Tom.

Tom and Mickey say they still love to take jaunts to see friends in the Hamptons.

“Our favorite thing in the Hamptons is the Tartufo at Nick & Toni’s. OMG do you like ice cream and nuts? It’s homemade, it’s insane, I once had an entire one (it’s meant for four people),” says Tom, with Mickey confirming.

“We also love Westhampton Beach Performing Arts Center,” says Tom, adding “We go there often. And Guild Hall is fabulous. “Oh, and Atlantic Beach (in Amagansett) is our beach,” adds Mickey.

Naturally, when Tom and Mickey entertain at their home in Nissequogue on the North Shore, guests have a choice of three guest rooms that Tom & Mickey describe as “personality suites for Frank Sinatra, Noel Coward and Peter Allen. You get to pick whichever one you want,” says Tom, laughing.

When they are not showing a property, Tom and Mickey still enjoy a good sing-along, whether it is in tandem with their antique Steinway player piano, or when they are out and about.

“We get up at cocktail parties — anytime there are friends, clients, family, a piano — we are usually singing a song,” says Tom.

“We like our audiences good and drunk, because they’re not judgmental,” quips Mickey.

As for the Jazz Loft series, Tom and Mickey couldn’t be more excited.

“Music brings people together and music and the arts bring communities together,” says Tom, who then shares a text from composer Jimmy Webb’s wife Laura Savini.

“Mickey and I had invited Jimmy Webb and his wonderful wife Laura Savini to see Vince Giordano and the Nighthawks (the first show in their Jazz Loft series in early July),” he adds. Laura wrote, ‘Thank you and Mickey for the love and excitement you put into this life.’ And I thought that’s sweet, that’s really the gist of it.”

The Summer Music Series at the Jazz Loft in Stony Brook presented in partnership with Tom Postilio and Mickey Conlon and Douglas Elliman Real Estate will feature John Pizzarelli (Aug. 13) and Peter Cincotti (September 24) For more info and tickets, visit the jazzloft.org and/or tomandmickey.com.