Stephen Weisberg is a Detroit-based tax attorney who helps individuals and business owners resolve IRS controversies and tax-debt issues. In this episode, he shares how the 2008 recession launched him from corporate bankruptcy work into tax law, why most people wait too long to seek help, and what every lawyer (and taxpayer) should know before they get that letter from the IRS.
Tax attorney Stephen Weisberg explains how he built a career helping clients navigate IRS debt, avoid costly mistakes, and understand when it’s time to call in an expert.
Stephen Weisberg’s legal career began in Detroit during one of the toughest economic periods in recent history. Graduating in 2008, he entered a world of foreclosures, bankruptcies, and failing suppliers across the auto industry. His first roles were in corporate bankruptcy, representing large suppliers that owed millions to the “Big Three” automakers. Working within these massive cases taught him the mechanics of finance, debt, and negotiation, but something was missing.
“I didn’t feel like I was making a difference. I wanted to see it in the faces of business owners," shares Stephen Weisberg on You Are A Lawyer.
That desire to help real people eventually led him into tax controversy work. Through a colleague who specialised in the field, Stephen discovered a way to use his legal skills to directly change lives, helping small-business owners and individuals untangle tax debts, deal with the IRS, and find financial relief. Today he’s built a respected practice, The W Tax Group, where he manages cases nationwide and leads a small team of attorneys and support staff focused on one mission: solving tax problems with empathy and precision.
For Stephen, the path to law school was almost inevitable. His father had practised law for more than forty-five years, and his uncle was a family-law attorney, so the profession felt familiar. Even so, he didn’t enter law school with a clear idea of what kind of lawyer he wanted to be. He only knew he enjoyed research, critical thinking, and healthy debate; skills that came naturally.
“I saw my father do well, and I felt like I had some characteristics that would make me a good lawyer," explains Stephen Weisberg on Episode 217 of You Are a Lawyer.
While he hadn’t foreseen a future in tax law, law school gave him the analytical framework that would later help him navigate complicated IRS cases. Like many students, he assumed the degree would prepare him for practice. Looking back, he laughs at how little law school teaches about the realities of building a business, managing clients, or marketing a service. Those lessons, he says, come only from experience.
Stephen’s journey proves that a law degree is both a credential and a toolkit. His early work in bankruptcy law introduced him to financial systems and creditor negotiations, while his tax practice taught him how to translate that technical knowledge into advocacy for everyday people. Tax controversy work isn’t glamorous, but it’s vital—and it’s year-round.
“People think I’m busiest during tax season, but that’s when the IRS is focused on filing. My work happens the rest of the year," shares Stephen Weisberg on Episode 217 of You Are a Lawyer.
He’s built a steady stream of clients through LinkedIn networking, attorney referrals, and partnerships with CPAs, CFOs, and financial planners. The relationships he’s developed prove that collaboration, not competition, sustains a modern law practice. Most of his cases are handled remotely by phone or Zoom, reflecting how legal work has evolved since the pandemic.
Unlike many guests, Stephen doesn’t juggle creative side projects. His “side hustle” is the business itself. Running a boutique law firm has required him to master entrepreneurship: hiring, leadership, marketing, and client education. He readily admits that when he first launched his own practice, he had no idea what he was doing.
“I hadn’t run a business and I didn’t have clients. You just get thrown into the fire and figure it out,” Stephen Weisberg expresses in Episode 217 of You Are a Lawyer.
That honesty underpins his advice to young lawyers: success doesn’t come from chasing the perfect niche or waiting for passion to strike. It comes from showing up, learning fast, and becoming good at what you do. Over time, the confidence and competence build their own passion. For Stephen, helping clients find relief from crushing tax debt is more than legal work, it’s deeply human work.
Stephen is licensed to practice in Michigan.
This episode is produced by Skip The Boring Stuff, a podcast strategy company for business owners and creatives.
