The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
Podcast Description
My name is Jordan Ostroff, the lawyer with a life (one that features Hawaiian shirts and flip flops). Are you looking for insights on thriving in business without burning out? Welcome to the LEI'D Back Life podcast! Join me weekly as I dive into candid conversations with entrepreneurs about developing a business, and a life, you'll love, LEI'D Back style.
Podcast Insights
Content Themes
This podcast covers themes surrounding work-life balance, entrepreneurship, and personal development, including episodes like 'Using Your Business to Build the Freedom You Want' and insights into financial strategies, creativity in business, and the importance of personal hobbies.

You started your law firm for more freedom, control, income, and flexibility. But somewhere along the way, the business started running you.
From Esq. to Owner is a practical podcast for solo and small firm attorneys who are great at practicing law but are still figuring out how to lead, manage, hire, delegate, market, and grow.
Hosted by Jordan Ostroff, the Hawaiian-shirt-wearing Lawyer with a Life, this show brings practical solutions with a side of candor, humor, and the occasional pop culture reference. Jordan helps attorneys move from carrying everything themselves to owning and leading the firm they’ve always wanted.
Each episode tackles the real challenges attorneys face after opening their own firm: pricing, staffing, intake, marketing, systems, time management, profitability, leadership, and getting out of the day-to-day chaos.
And because Jordan believes the whole point of building a better firm is having a better life, every episode ends with a little off-the-wall fun…a question, a hot take, a dad joke, a pop culture reference, or something completely unrelated to law.
If you feel buried by the business side of your firm and want solutions for building something better, this show is for you.
Powered by Atticus.
Build Your Firm. Get Your Life Back.
Have you ever had a client complain about a case you thought you handled exceptionally well? Or received a negative review that bothered you far more than you’d like to admit?
When you’ve invested so much of yourself into your work, it’s hard not to take criticism personally. You can have dozens of satisfied clients, yet somehow the one who’s unhappy is the one you can’t stop thinking about.
In this episode of From Esq. to Owner, Jordan Ostroff gets into one of the more frustrating parts of running a law firm: dealing with unhappy clients, managing expectations, and handling criticism when it feels personal.
Drawing from his own experiences, Jordan challenges attorneys to think differently about client complaints, what they mean for your business, and how much power you give them over your time and attention.
If you’ve ever let one difficult client ruin an otherwise good day, you’ll want to hear Jordan’s perspective.
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Inside This Episode:
- How to recognize client red flags and unrealistic expectations during intake
- Why listening before reacting can help resolve client complaints
- When to address a complaint, make an accommodation, or stand firm
- How to handle negative online reviews without compromising client confidentiality
- How to use client feedback to improve your firm’s systems and client experience
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Supporting Resources
Attorney and Practice Advisor Jordan Ostroff: https://atticusadvantage.com/team/jordan-ostroff/
Book: Mindset by Carol Dweck https://a.co/d/09PvO5W6
Book: One Small Step Can Change Your Life: The Kaizen Way to Success by Dr. Robert Maurer: https://a.co/d/0h3dbO8D
Atticus Coaching: https://atticusadvantage.com/coaching/
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Curious about what it takes to move from practicing law to truly owning your law firm? Contact Atticus to learn how our law firm coaching can help solo and small firm attorneys build stronger systems, lead better teams, delegate with confidence, and make smarter decisions about growth. From Esq. to Owner is a podcast for law firm owners who want practical guidance on law firm leadership, hiring, delegation, operations, marketing, profitability, client service, and sustainable growth, so the business supports your life instead of running it.
You can also sign up for the Atticus newsletter to get practical insights on how to grow a law firm, strengthen your role as an owner, improve your systems, and build a more focused, profitable, and sustainable practice.
https://atticusadvantage.com/newsletter-signup/
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Timestamps:
00:00 A Negative Review Does Not Make You a Failure
01:06 How to Handle Difficult Clients Without Taking It Personally
01:42 What Domino’s Can Teach Law Firms About Complaints
03:29 The Best Way to Prevent Client Complaints
04:08 Red Flags Before You Ever Take the Case
05:47 20% of Clients Can Create 80% of Your Problems
06:46 The Best Kind of Client Complaint
07:35 Respond to Complaints, Don’t React to Them
10:18 Is the Client’s Complaint Actually Valid?
11:04 Turn Valid Complaints Into Better Systems
13:51 What to Do When the Complaint Is Unreasonable
16:03 What Happens When the Complaint Becomes a Bad Review
17:40 Your Review Response Is Really for Everyone Else
19:19 Why a Few Bad Reviews Aren’t Necessarily a Bad Thing
24:27 A Bad Review Is a Learning Opportunity, Not a Failure

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