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 Check out my new show, Be That Lawyer Coaches Corner, and get the strategies I use with my clients to win more business and love your career again. Join the Be That Lawyer Community and connect with ambitious lawyers who are serious about growing their book of business, strengthening their brand, and becoming confident, consistent rainmakers. Ready to go from good to GOAT in your legal marketing game? Don’t miss PIMCON—where the brightest minds in professional services gather to share what really works. Lock in your spot now: https://www.pimcon.org/ Thank you to our Sponsor! LEX Reception: https://www.lexreception.com/partners/bethatlawyer Rankings.io: https://rankings.io/ Lawyer.com: https://www.lawyer.com/ Ready to grow your law practice without selling or chasing? Book your free 30-minute strategy session now—let's make this your breakout year: https://fretzin.com/ 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 Email: Steve@Fretzin.com Book: Legal Business Development Isn't Rocket Science and more! YouTube: Steve Fretzin Call Steve directly at 847-602-6911 Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.
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:
Key Takeaways:
"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
Check out my new show, Be That Lawyer Coaches Corner, and get the strategies I use with my clients to win more business and love your career again.
Join the Be That Lawyer Community and connect with ambitious lawyers who are serious about growing their book of business, strengthening their brand, and becoming confident, consistent rainmakers.
Ready to go from good to GOAT in your legal marketing game? Don’t miss PIMCON—where the brightest minds in professional services gather to share what really works. Lock in your spot now: https://www.pimcon.org/
Thank you to our Sponsor!
LEX Reception: https://www.lexreception.com/partners/bethatlawyer
Rankings.io: https://rankings.io/
Lawyer.com: https://www.lawyer.com/
Ready to grow your law practice without selling or chasing? Book your free 30-minute strategy session now—let's make this your breakout year: https://fretzin.com/
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
Email: Steve@Fretzin.com
Book: Legal Business Development Isn't Rocket Science and more!
YouTube: Steve Fretzin
Call Steve directly at 847-602-6911
Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.