From Burnout Lawyer to 3-Day Workweek CEO (Making Millions) — with Jordan Ostroff

Failure — true failure — is staying stuck doing what you don’t love. That’s the trap Jordan Ostroff found himself in: running a 6-lawyer firm, $200K in debt, and every problem landing on his desk. In this episode, Sasha Berson and Jordan discuss how he rebuilt everything, scaling to 25 employees, raking in millions, while allowing him to work three days a week.

📰 About Jordan Ostroff:
Jordan Ostroff is the brilliant founder of Driven Law and author of Love Your Law Firm. A former prosecutor turned business owner, Jordan knows firsthand what it feels like to be crushed by a law firm that’s successful on the outside but chaotic on the inside. After a breaking point when his wife became pregnant, he rebuilt everything. Today, he works three days a week and successfully runs a multi-million-dollar practice.

👉 Sasha and Jordan explore:
— Why staying miserable is the true definition of failure.
— The “bullseye org chart” mistake that made Jordan the bottleneck for everything.
— How cutting $130K in marketing spend made his firm more profitable.
— Key systems and delegation shifts that create freedom and profit.

👉 Main Takeaways from the Episode:
If every problem lands on your desk, start by listing recurring tasks and delegating them.
Look at your marketing budget with a critical eye; if dollars don’t tie directly to signed cases, cut the spend.
Decide how many hours you actually want to work, then build the systems and staff to make that schedule possible.
If you enjoyed today’s show, please leave a review and subscribe so you never miss an episode. For more information and links to all of the resources mentioned in today’s episode, visit https://growlaw.co/

📞 Connect with Jordan Ostroff:
• Website: https://www.jordanostroff.com/
• LinkedIn:   / jordan-ostroff  
• Jordan’s Book: https://www.amazon.com/Love-Your-Law-...

📞 Connect with Sasha Berson:
• LinkedIn:   / grow-law  
• Instagram:   / grow_law  
• YouTube:    / @growlaw  
• Facebook:  / growlaw  
• Email: [email protected]
• Phone: (312) 854-7724
#LegalMarketing #LawFirmGrowth #BusinessGrowth #LegalIndustryInsights

00:00 – Introduction
02:06 – Meet the Guest: Jordan Ostroff
03:08 – The Core Philosophy: "You Fall to the Level of Your Systems"
04:22 – The First Moment of Clarity: Quitting the Prosecutor's Office
12:17 – The "Bullseye Org Chart": A Recipe for Misery and Burnout
15:13 – The Second Moment of Clarity: How Becoming a Father Changed Everything
21:08 – The Transformation from Lawyer to CEO
26:46 – How a Daily Live Show Saved the Firm During COVID
37:35 – Why We Intentionally Don't Use SEO: The Power of a Referral-Based System
46:02 – The Story Behind the Book "Love Your Law Firm"
58:16 – Connect with Jordan