Grow A Small Business Podcast · Troy Trewin

Founder of Leave Law Behind — shares how he transformed his own career shift from law into a thriving online business helping unhappy attorneys pivot, scaling to $500K a year through coaching, courses, and smart automation. (Episode 746 - Casey Berman)

·43 min·2 clips

A first paying client paid Casey about $750 to get out of law.

Casey Berman starts by tracing the path from law school to a hard career turn. He graduated in 1999. Five years later, he realized the work was not for him. He then spent time in management consulting. In 2010, he started blogging. That writing brought in his first coaching clients, often people in law who wanted to change careers as he had. The business grew out of that familiar problem. In 2015, a business partner joined. Soon after, the offer shifted toward online courses. Troy keeps asking for the usual founder markers: growth, funding, stress, and lessons. Casey answers with a practical, plainspoken view of how the company operates. He says the business is doing around half a million US dollars a year. He also notes that the team began with 1 FTE. It is now around five people, including contractors. The conversation stays focused on discipline. Casey is clear that motivation only goes so far. The work still has to get done on the days when it feels hard to start. He also talks about knowing when to stop pushing, because sleep and a clean first draft matter too. On funding, he describes a bootstrapped business that leaned on credit cards and a line of credit while staying fully owner-controlled. He closes by saying that, if he had to start again, he is not sure he would target lawyers in the same way, even though he still likes helping them.

As heard by us

A lawyer's pivot becomes a steady lesson in bootstrapping, discipline, and building a business around a career-change audience.

Casey Berman's arc is plain and effective: a law degree in 1999, five years in practice, then a move into management consulting before blogging started bringing in coaching clients who wanted the same career shift.

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Why you'd press play

A lawyer's exit route turned into a bootstrapped online business.

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