December 12, 2025

From Number Crunching to Piano Keys: Mike Maimone’s Journey of Love, Loss & Reinvention

32 minutes

In this soulful and unfiltered conversation, singer-songwriter Mike Maimone—a former accountant turned queer creative force—shares how love, loss, and midlife reinvention shaped his music and life.

From finding love across an age gap with late partner Howard Bragman, to channeling grief into his upcoming album and book, Guess What, I Love You (out February), Mike opens up about rediscovering purpose after heartbreak. Together, Rick and Mike dive into healing, queer resilience, and what it means to live unapologetically authentic—no fears, no excuses, no apologies.

Three Key Takeaways

Reinvention knows no age limit: Mike’s switch from accounting to full-time musician proves it’s never too late to follow your authentic rhythm.

Love isn’t defined by age—it’s anchored in shared values and authenticity; Mike and Howard’s story shows how connection outlasts external assumptions.

Grief can become creative fuel: Mike transformed loss into art, launching an album and book that honor memory by turning pain into performance.

About Mike

Originally a business school graduate and accountant, Mike Maimone made his way into full-time music through Chicago’s blues scene, drawing comparisons to legends like Randy Newman and Leon Russell. He has since performed more than 100 shows annually, appearing at festivals such as Lollapalooza, Riot Fest, and Summer Camp, while sharing stages with Blues Traveler, Plain White T’s, and Company of Thieves.

His music has been placed on TV soundtracks and even featured at Wrigley Field. In 2023, Maimone released Borrowed Tunes, Vol. 2, followed by sold-out shows in Los Angeles, New York, and Chicago, with proceeds benefiting The Trevor Project. A live album, Songs for You, Alive in Chicago, followed in early 2024. His forthcoming album Guess What? I Love You, available for pre-order in limited-edition vinyl and CD formats, will include handwritten lyrics, liner notes, and photos, further underscoring the deeply personal nature of the project.

Connect With Mike

Website

Instagram

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By Rick Clemons

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