By Steve Fretzin, Jordan Ostroff, and Jeremy Baker

Going Solo: The Real Math Behind a Thriving Law Practice

Two lawyers who left prosecution and Big Law share the mindset, financial reality, and first 90-day moves that determine whether a solo practice sinks or scales

Going solo is one of the most searched and least honestly discussed topics in the legal profession. Everyone has an opinion. Few people share the actual numbers, the real mistakes, or what the first ninety days look like when the safety net is gone.

That is exactly what this episode delivers. Jordan Ostroff and Jeremy Baker have both done it from completely different starting points and they came on the show to talk about what they got right, what they got wrong, and what they would do differently. Jordan is the CEO of Driven Law and Carpe Diem Consulting, a former prosecutor who clawed his way out of $200,000 in early business debt to build a thriving low-volume personal injury practice and write a bestselling book about it. Jeremy is a veteran construction attorney now in his sixth year of solo practice, specializing in cost-efficient dispute resolution for owners, developers, and design professionals.

Between the two of them, this conversation covers the full arc of what it actually takes to launch and grow a solo law practice.

The Moment You Know It Is Time to Leave

Both Jordan and Jeremy describe a version of the same experience: a clear moment of misalignment. Not a gradual drift, but a specific realization that the next promotion, the next milestone, or staying the course was not going to produce the life or career they actually wanted.

That clarity matters more than most lawyers realize. Because without it, the anxiety of going solo tends to win. You keep planning, keep preparing, keep waiting for the perfect moment and the perfect moment never comes. The decision to launch a solo practice is not purely financial. It is a values question first.

Leaving the Right Way

One of the most practical parts of this conversation is about what happens in the transition itself. How you leave a firm has long-term consequences most lawyers underestimate.

Jordan and Jeremy are both direct about it: maintain integrity, communicate openly, and do not burn anything down on your way out. Former colleagues become referral sources. Former supervisors become allies. The legal community is smaller than it looks, and your reputation follows you everywhere.

Leaving the right way is not just the ethical move, it is a business development strategy.

The Real First 90 Days: Cash Flow, Contacts, and Clarity

If there is one place where new solos most often go wrong, it is in the first ninety days. Too much time spent on the logo, the website, the tech stack, and the perfect office setup. Not enough time spent on the only thing that actually keeps a practice alive: generating revenue.

Jordan and Jeremy both emphasize the same priorities for early-stage solo practice:

Know your numbers. What will you spend each month? What do you need to earn to break even? What does a realistic pipeline of new files look like? A clear financial and marketing plan, even a rough one is more valuable than any branding decision you will make in year one.

Work your existing contacts first. The lawyers who grow fastest out of the gate are not the ones waiting on SEO or digital ads to kick in. They are the ones picking up the phone and having real conversations with people who already know and trust them. Your network is your fastest path to your first clients.

Protect your cash flow above everything. Early-stage solos who survive long enough to figure things out are the ones who do not let overhead outpace income. Keep costs lean until revenue is consistent, not the other way around.

AI and Lean Tech: A Tool, Not a Strategy

One of the more useful conversations in this episode is about technology. Both Jordan and Jeremy use AI tools to reduce startup costs, speed up drafting, and handle tasks that would otherwise require additional staff or overhead.

But they are clear about where the line is. AI accelerates execution. It does not replace the relationship-building and consistent outreach that actually grow a solo law practice. Lawyers who lean too hard on tools and systems in the early stages often find themselves with a beautifully optimized firm that has no clients.

Use the technology. Do not hide behind it.

Hiring: The Mistake That Bites Twice

Jeremy’s quote on hiring is one of the most honest things said on the show in a while.

“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

That pattern is more common than lawyers want to admit. The first mistake is waiting too long, staying buried in work that could be delegated, because letting go feels risky. The second is hiring reactively out of desperation rather than strategy, which leads to the wrong people in the wrong roles.

The fix is neither complicated nor immediate. It starts with being honest about what you actually need, what your budget actually allows, and what alignment with your values and working style looks like before you post a job listing.

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. He is the bestselling author of Love Your Law Firm and now works 20–25 hours a week while coaching other attorneys to achieve a similar quality of life and career on their own terms.

About Jeremy Baker

Jeremy Baker is a veteran construction attorney and litigator now in his sixth year of solo practice, representing owners, developers, and design professionals. He specializes in cost-efficient solutions for contract negotiation, dispute avoidance, and alternative dispute resolution, and has litigated in more than 30 venues and dozens of arbitrations. An early proponent of the Guided Choice Dispute Resolution System, Jeremy focuses on resolving high-stakes claims strategically and without the cost of traditional litigation wherever possible.

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
Email: Steve@Fretzin.com
Book: Legal Business Development Isn’t Rocket Science and more
YouTube: Steve Fretzin Call Steve directly at 847-602-6911

Ready to grow? Schedule Your Free Consultation

If you’re looking to grow your practice, there’s no better time to schedule your free consultation. Simply fill out the form below or call (847) 602-6911.

The post From Big Law and Prosecution to Thriving Solo Practices appeared first on FRETZIN, INC..