John Martin — From Debt Collection to Million-Dollar Wins

It was a longshot case. After all, the jury knew that John Martin’s client, suing for employment discrimination, already had retirement benefits. But this fight was about whether she was entitled to a different category of benefits. Confident they’d win, the defense rejected an offer to mediate. A jury awarded $1.75 million. “I just got the email this morning that they just mailed the checks,” John tells host Dan Ambrose in this wide-ranging discussion about his career. With 35-40 civil jury trials under his belt since graduating from Suffolk University Law School in 2009, John reflects on his journey from debt collection rookie to winning trial lawyer at Keches Law Group. Tune in for his insights about how modern AI is revolutionizing case preparation, how the settlement trap derails many lawyers' careers, and how personal adversity can forge fearless courtroom warriors.

Episode Snapshot
John uses AI tools like GPT Pro to synthesize deposition transcripts, create contradiction tables, and streamline case preparation for his upcoming trial.
After failing to complete high school initially, John participated in Up With People, a traveling performance organization that taught him service and built performance confidence.
His path to law school was sparked by his fiancé's mother's misdiagnosis of kidney cancer and the unresponsiveness of top Boston medical malpractice attorneys.
After graduating from law school during the 2008-09 recession, John’s commitment letters were rescinded, so he turned to a debt collection law firm. His career there lasted through one court appearance, when he told a judge that many debtors were “judgment proof.” “No one's ever judgment proof, so they no longer needed my services.”
In his first civil jury trial against the Boy Scouts of America, John secured $152,500 in economic damages plus $300,000 in punitive damages.
John's son Jack was born with Smith-Lemli-Opitz syndrome and pulmonary vein stenosis, requiring three years of chemotherapy and multiple heart surgeries.
Through Jack's medical journey, John learned to let go of outcome obsession and developed fearlessness in the courtroom that dramatically improved his trial results.
John represents an iron worker who injured his shoulder while replacing braces on a high-end construction project in Cambridge, Massachusetts. He’s preparing for trial, scheduled to start this month.

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☑️ John Martin
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