The LEI'D Back Life: Loving Entrepreneurship and Improving Daily

About The LEI'D Back Life: Loving Entrepreneurship and Improving Daily

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.

Publisher

Lawyer with a Life - Jordan Ostroff

Category

business · business · education

Language

en

Explicit

No

First episode

29 Oct 2024

Latest episode

8 Oct 2026

Latest episodes

102 episodes in the feed.

1. 

   8 Oct 2026

   Are You Using AI to Build a Business or Just Do More Work? feat. Carolyn Elefant

   AI can help you get more done. But what are you doing with all that extra capacity? When AI helps you research, create marketing, communicate, and move through your to-do list faster, it's tempting to fill that newly available time with...more work. In this episode of From Esq. to Owner, Jordan Ostroff sits down with Attorney Carolyn Elefant to talk about a bigger opportunity: using AI to help build a law firm that operates more like a business and depends less on the owner doing everything. They discuss where AI can support better systems and delegation, how technology is changing what it takes to start and grow a firm, and why the processes you build can become valuable assets in the business. They also get into an important question every law firm owner using AI eventually has to answer: when should technology handle the work, and when do you still need a human? And because using AI responsibly matters just as much as using it efficiently, Jordan and Carolyn tackle confidentiality, ethics, and some of the risks that come with bringing these tools into your practice. Because the goal isn’t to use AI to cram more work into your day. It’s to use that capacity to build a better law firm. ---------------- Inside This Episode: Why getting more done with AI doesn’t necessarily mean building a better firm How AI can support stronger systems and better delegation Why your processes can become valuable business assets When AI makes sense and when you still need human expertise What law firm owners need to consider about confidentiality, ethics, and responsible AI use ---------------- Supporting Resources Carolyn Elefant LinkedIn: https://www.linkedin.com/in/carolynelefant/ (https://www.linkedin.com/in/carolynelefant/) MyShingle: https://www.myshingle.com/ (https://www.myshingle.com/) Book: Four Thousand Weeks by Oliver Burkeman: https://www.oliverburkeman.com/books (https://www.oliverburkeman.com/books) The Summit: https://atticussummit.com/ (https://atticussummit.com/) ---------------- 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/ (https://atticusadvantage.com/newsletter-signup/) ---------------- Timestamps: 00:00 - You Can’t Put the AI Genie Back in the Bottle 01:07 - Building an AI-Native Law Firm From Day One 01:45 - How Much of Starting a Firm Can AI Actually Do? 05:14 - The Advantage of Starting Fresh With AI 07:00 - How AI Changes the Way You Think and Work 09:08 - Do We Actually Need to Be Less Productive? 14:38 - Using AI to Lower Startup Costs 17:07 - From Self-Employed Lawyer to Business Owner 19:02 - How Your Goals Change When You Own a Business 22:09 - Can AI Make You a Better Delegator? 26:49 - AI Can Become an Asset of Your Business 28:22 - Using AI Responsibly: Ethics and Privacy 33:49 - Should Lawyers Tell Clients They Use AI? 36:00 - Could NOT Using AI Eventually Be Unethical? 39:50 - Carolyn’s Biggest Advice for Lawyers

2. 

   1 Oct 2026

   Getting Faster Should Make You More Money. So Why Doesn’t It? feat. Regina Edwards

   If you bill by the hour, getting faster at your job can actually mean making less money. That’s a weird incentive when you think about it. Regina Edwards has been thinking about it for a long time. For the past 15 years, she’s built her family law practice around flat fees, creating a model where becoming more efficient is actually good for the firm and the client. In this episode of From Esq. to Owner, Regina joins Jordan Ostroff to talk about what she’s learned along the way, including the pricing mistakes that cost her money, the clients who aren’t a good fit for flat fees, and the systems she had to build to make the model work. Now AI is changing the equation again. Work that once took hours or even days can happen much faster, raising some pretty big questions about what attorneys are really selling and how we should be charging for it. If your firm is getting faster at delivering legal work, it may be time to ask whether your business model is keeping up. ---------------- Inside This Episode: How to structure flat fees for complex legal matters Why strong systems should come before automation How Regina uses AI without removing human review Why client expectations matter when you stop billing by the hour How flat fees can make efficiency more valuable to your firm ---------------- Supporting Resources Regina Irene Edwards https://www.edwardsfamilylaw.com/lawyers/regina-irene-edwards (https://www.edwardsfamilylaw.com/lawyers/regina-irene-edwards/) Edwards Family Law https://www.edwardsfamilylaw.com (https://www.edwardsfamilylaw.com/) Regina on LinkedIn https://www.linkedin.com/in/georgiafamilymatterslaw (https://www.linkedin.com/in/georgiafamilymatterslaw/) Dye Hard Legal Tech https://www.dyehardlegaltech.com (https://www.dyehardlegaltech.com/) Lawyer on the Beach Facebook Group https://www.facebook.com/groups/lawyeronthebeach (https://www.facebook.com/groups/lawyeronthebeach/) ---------------- 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/ (https://atticusadvantage.com/newsletter-signup/) ---------------- Timestamps: 00:00 Why You Should Trust Your Gut When Taking Cases 01:08 Meet Reginia Edwards: Flat Fees, Family Law and AI 02:00 Why She Walked Away From Hourly Billing 03:00 Building a Flat-Fee Law Firm 06:45 Screening Clients and Setting Expectations 08:00 Explaining Flat Fees to Clients 09:50 Better Client Communication and Proactive Updates 12:50 How to Price Flat-Fee Cases Profitably 17:20 Why You Should Turn Down Bad Clients 19:50 Starting With Flat Fees Without Losing Money 21:45 Building Systems Before Introducing AI 25:00 Using Claude Skills to Automate Legal Work 30:00 Why You Must Verify AI-Generated Work 33:00 Building Better AI Workflows With Checklists 42:00 The Future of AI and Building a Better Law Firm

3. 

   24 Sept 2026

   Stop Sending Forgettable Holiday Gifts feat. Jordan Ostroff with special guest Daniel Struna

   It might feel early to start thinking about holiday gifts. That’s exactly why now is the right time. Because if you wait until everyone else is ordering the same bottles of wine and branded swag, you’ve already missed the chance to do something memorable. In this episode of From Esq. to Owner, guest host Daniel Struna sits down with Jordan Ostroff to talk about why the usual approach to referral gifts often misses the point and what law firm owners can do differently. Jordan shares how to make gift-giving feel more personal, strengthen referral relationships without making them feel transactional, and stay connected with the people who matter to your practice throughout the year. You don’t need a massive gift budget or complicated technology. But you do need to be more intentional than sending the same thing to everyone because the calendar says it’s time. Because the goal isn’t to send more stuff. It’s to build relationships people actually remember. ---------------- PODCAST SPECIAL OFFER: Save $100 on a Practice Growth Diagnostic For a limited time, you can get a Practice Growth Diagnostic for $225, normally $325. You will receive: A comprehensive assessment of your law firm A DISC personality assessment A one-hour strategy session to review your results and identify your 3 Most Impactful Actions Get a clearer picture of what is working, what needs your attention, and where to focus next. Use code PODCASTPGD100 at checkout to save $100. GET YOUR PRACTICE GROWTH DIAGNOSTIC: https://gn477.infusionsoft.com/app/orderForms/PGD (https://gn477.infusionsoft.com/app/orderForms/PGD) ---------------- Inside This Episode: Why generic gifts and branded swag are so easy to forget How to make gifts more personal without spending more A simple way to keep track of the details that matter How to make relationship-building part of your existing systems How to stay top of mind without making relationships feel transactional ---------------- Supporting Resources Daniel Struna: https://atticusadvantage.com/team/daniel-struna/ (https://atticusadvantage.com/team/daniel-struna/) How Good Attorneys Become Great Rainmakers, Updated Edition by Mark Powers & Shawn McNalis: https://atticusadvantage.com/books/how-good-attorneys-become-great-rainmakers-updated-edition/ (https://atticusadvantage.com/books/how-good-attorneys-become-great-rainmakers-updated-edition/) How to Win Friends and Influence People by Dale Carnegie: https://a.co/d/0fk52V96 (https://a.co/d/0fk52V96) The Goal: A Process of Ongoing Improvement by Eliyahu M. Goldratt & Jeff Cox: https://a.co/d/0duYwDxL (https://a.co/d/0duYwDxL) Get a Practice Growth Diagnostic with Jordan. Spots are limited! Grab it fast if you want one. https://gn477.infusionsoft.app/app/orderForms/2026-PGD-Podcast (https://gn477.infusionsoft.app/app/orderForms/2026-PGD-Podcast) ---------------- 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/ (https://atticusadvantage.com/newsletter-signup/) ---------------- Timestamps: 00:00 The $250K Referral Source You Forgot to Thank 00:33 From Esq. to Owner Intro 01:07 Why Holiday Gift Giving Matters for Law Firms 02:18 When a “Gift” Actually Hurts Your Brand 03:03 Why Branded Swag Isn’t Really a Gift 04:45 How to Choose Better Gifts for Referral Sources 05:15 Experiences vs. Physical Gifts 06:05 Give Better Gifts to Fewer People 06:21 The Gift People Actually Remember 09:10 A Simple Way to Track Personal Details 11:38 Building a System for Thank-Yous and Gifts 14:00 Making Gift Giving Part of Your Workflow 16:51 Gift-Giving Mistakes Law Firms Should Avoid 18:54 How Much Should You Budget for Gifts? 22:32 Starting a Referral Gift Strategy From Zero

Who has been a guest on The LEI'D Back Life: Loving Entrepreneurship and Improving Daily

Names identified in recent episode analyses. Showing up to five guests.

• Aaron Rothert
• Mark Powers
• Shawn McNalis
• Seth Kuntz
• Denise Cullen

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

7 ratings

Spotify

5.0 / 5

3 ratings

Podcast Authority Score: 35 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

71

Social presence

0

YouTube

0

Engagement

0

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