Singer-songwriter Mike Maimone recently released a new single entitled “On My Way”, which serves as the first single from his upcoming album Guess What? I Love You. The song is a deeply personal tribute to his late husband, renowned PR guru Howard Bragman. The origin of the song was a voicemail Mike left for Howard during their long-distance romance. After his husband’s passing, Mike transformed the heartfelt message into a full song, adding a verse, a bridge, and layers of stomps, claps, and snaps.
“We were always hopping planes to see each other,” Maimone recalls. “Just before one trip, I called him with guitar in hand and sang this little ditty that was running through my head about how excited I was to see him. He didn’t pick up, so I left it as a voicemail. He told me it was fun and catchy and encouraged me to turn it into a full song.”
The Ohio-born artist, who once played basketball against LeBron James, transitioned from a business school graduate and accountant to a full-time musician. His raw, emotive songwriting and electrifying performances have drawn comparisons to Randy Newman, Leon Russell, Tom Waits, and Warren Zevon. He has toured with Blues Traveler and the Plain White T’s and played festivals, including Lollapalooza, Riot Fest, and Summer Camp.
Mike’s upcoming LP, Guess What? I Love You is a deeply personal tribute to Howard, chronicling their love story and his own journey through grief, love, and healing. The day after their wedding, he held his husband as he passed away. Over the next two years, he poured his emotions into Guess What? I Love You. Reflecting on the album’s structure, he explains, “Side A is about finding love, and Side B explores loss. I knew this album would be difficult for anyone who has experienced the trauma of losing a loved one before their time. But I didn’t want to leave the listener in darkness—I wanted to find a way out.”
We had a chance to catch up with Mike to discuss the new single, his musical influences, and much more in our exclusive interview. We got to know him even better as he answered the Socialite Seven.
How did you get your start in music?
My mom forced me to take piano lessons when I was five. I resisted until I started to get pretty good in middle school, and my teacher let me start playing pop songs. He was a 6’7” Hungarian man who made a grand piano look like a harmonica and sound like a rocket taking off. I wanted to be like that.
Who are your influences?
Fiona Apple, St. Vincent, Dr. Teeth & the Electric Mayhem, Nina Simone, Dethklok, Sarah Vaughan, Yeah Yeah Yeahs and Beyoncé
How would you describe your sound?
Like a rocket taking off.
What can listeners expect to hear from your album, Guess What? I Love You.?
It’s an emotional roller coaster. We’ll laugh, we’ll cry, we’ll hug our loved ones a little bit tighter.
Do you have a favorite song that you’ve recorded (besides “On My Way”)?
I’ve rarely laughed out loud while writing or producing a song, but “Paranoid in Paradise” gave me the giggles on several occasions.
You’ve performed with a lot of artists and on many festival stages. What do you enjoy about performing live?
The sharing of energy between performer and audience is a high unlike anything else.
What are you hoping people will take away from your music?
From this record in particular, I hope people will be interested in learning more about my late husband, Howard Bragman. He was truly remarkable, and although his work was behind the scenes as a publicist, he belongs in the mix when we talk about standing on the shoulders of giants as our community continues to fight for our very right to exist. And in a broader sense, by sharing our tragic but beautiful love story, I hope listeners will be moved to love boldly and cherish every moment we have together.
What’s next for you?
While writing and producing this album, I wrote a companion memoir. It was such a brutal but necessary catharsis for me. I’ve always enjoyed writing but was surprised by the positive reaction from author and editor friends of mine. I’m very proud of it and hope that it will come out in 2026.
Mike Maimone Answers the Socialite Seven
What is your biggest pet peeve?
When people chew with their mouths open
What is your most cherished possession?
My medically oversized heart
Who would you want to play you in the movie of your life?
Tom Hanks
What superpower or talent would you like to wake up with tomorrow?
Teleportation. With a +1.
What are three things you can’t live without?
Lovemaking, Music, Coffee
What is your idea of perfect happiness?
Making love while listening to good music.
What’s the best piece of advice you’ve been given?
The things that make me different are the things that make me me!
Listen to “On My Way” here and keep up with Mike and his music here!
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