Thinking about going solo but stuck in anxiety and overplanning? In this episode, two lawyers who successfully left prosecution and big law share the real math, mindset, and first 90‑day moves that make or break a new solo practice.

In this episode, Steve Fretzin, Jordan Ostroff, & Jeremy Baker discuss:

Deciding when and why to go solo
Leaving a firm the right way and preserving relationships
Planning for cash flow, costs, and the first 90 days
Using AI and lean tech instead of heavy overhead
Common mistakes with hiring, planning, and business development

Key Takeaways:

The decision to launch a solo practice often comes from a clear moment of misalignment, realizing the “next promotion” or status quo is not the life or career you actually want.
A realistic financial and marketing plan, what you’ll spend, how you’ll earn, and where new files will come from, is more important than a perfect logo, office, or tech stack.
Maintaining integrity and open communication when you leave a firm protects your reputation, preserves referrals, and can turn former colleagues into long-term allies.
Early-stage solos should prioritize cash flow and relationships over tinkering with systems; networking your existing contacts usually beats waiting on websites and ads to work.
AI tools can dramatically reduce startup costs and speed up execution, but they are a supplement to, not a substitute for, consistent outreach and business development.

"What I did wrong in year one was I didn't hire people, and what I did wrong in year two is I hired people the wrong way." — Jeremy Baker

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About Jordan Ostroff: Jordan Ostroff is the CEO of Driven Law and Carpe Diem Consulting. A former prosecutor and the first lawyer in his family, Jordan overcame $200,000 in early business debt to build a thriving, low-volume personal injury practice. Now the best-selling author of Love Your Law Firm, he works 20–25 hours a week, allowing him time for family and coaching other attorneys to achieve a similar high quality of life.

About Jeremy Baker: Jeremy Baker is a veteran construction attorney and litigator representing owners, developers, and design professionals. In his sixth year of solo practice, he specializes in cost-efficient solutions for issues like contract negotiation and sustainable design. While an experienced litigator in 30+ venues and dozens of arbitrations, Jeremy prioritizes dispute avoidance and alternative dispute resolution. An early proponent of the Guided Choice Dispute Resolution System, he provides strategic advocacy to resolve high-stakes claims without the need for traditional litigation.

Connect with Jordan Ostroff:

Website: https://www.legaleasemarketing.com/

LinkedIn: https://www.linkedin.com/in/jordan-ostroff/

Connect with Jeremy Baker:

Website: https://designbuildlaw.com/

LinkedIn: https://www.linkedin.com/in/jeremysbaker/

Connect with Steve Fretzin:

LinkedIn: Steve Fretzin

Twitter: @stevefretzin

Instagram: @fretzinsteve

Facebook: Fretzin, Inc.

Website: Fretzin.com