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

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

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by Lawyer with a Life - Jordan Ostroff

90 episodes
Updated Daily
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35

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Podcast Overview

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.

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🇺🇲

Publishing Since

10/29/2024

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35

Podcast Authority

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Recent Episodes

Episode thumbnail for Want a Better Law Firm? Make Yourself Irrelevant feat. Victor Medina

July 16, 2026

Want a Better Law Firm? Make Yourself Irrelevant feat. Victor Medina

<p>Whether you're one year into your law firm or five, one question matters: Could your firm</p><p>survive without you?</p><p>Jordan Ostroff sits down with attorney and entrepreneur Victor Medina to explore how</p><p>building systems, empowering your team, and reducing founder dependence creates a</p><p>stronger law firm and a better life. Through personal stories and practical lessons, they</p><p>share how small changes today can protect your firm from tomorrow's unexpected</p><p>challenges while helping you become a true law firm owner.</p><p>What to Know More?</p><p>If you realize that your firm cannot survive without you, you need a new plan.</p><p>Many attorneys come to Atticus feeling burned out, overwhelmed, and trapped doing every</p><p>job inside their firm. We can walk through the Exile Exercise together and see how we can</p><p>build systems for your practice that can grow without you being there.</p><p>Schedule a complementary Discovery Call to explore what's possible for your firm and</p><p>learn how coaching can help you build a practice and a life you love.</p><p><a href="https://atticusadvantage.com/schedule/" rel="noopener noreferrer" target="_blank">https://atticusadvantage.com/schedule/</a></p><p>Inside This Episode:</p><p>• Why every law firm owner should prepare for the day they unexpectedly can't come</p><p>to work.</p><p>• How to identify the hidden ways your firm still depends on you.</p><p>• Simple systems that reduce bottlenecks and give your team more ownership.</p><p>• Why taking a real vacation is one of the best tests of your firm's health.</p><p>• The mindset shift that helps attorneys become true business owners instead of</p><p>indispensable employees.</p><p>----------------</p><p>Supporting Resources</p><p>Victor Medina <a href="https://atticusadvantage.com/team/victor-medina" rel="noopener noreferrer" target="_blank">https://atticusadvantage.com/team/victor-medina</a></p><p>Medina Law Group, LLC <a href="https://medinalawgroup.com/about" rel="noopener noreferrer" target="_blank">https://medinalawgroup.com/about</a></p><p>Connect with Victor on LinkedIn <a href="https://www.linkedin.com/in/victorjmedina" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/victorjmedina</a></p><p>Come Up For Air by Nick Sonnenberg: <a href="https://www.amazon.com/Come-Up-Air-Leverage-Drowning/dp/140023672X" rel="noopener noreferrer" target="_blank">https://www.amazon.com/Come-Up-Air-Leverage-</a></p><p><a href="https://www.amazon.com/Come-Up-Air-Leverage-Drowning/dp/140023672X" rel="noopener noreferrer" target="_blank">Drowning/dp/140023672X</a></p><p>DISC Assessment: <a href="https://atticusadvantage.com/disc-assessment/" rel="noopener noreferrer" target="_blank">https://atticusadvantage.com/disc-assessment/</a></p><p><a href="The Summit https://atticussummit.com" rel="noopener noreferrer" target="_blank">The Summit https://atticussummit.com</a> (Use code PODCAST100 to get $100 off)</p><p>----------------</p><p>Curious about what it takes to move from practicing law to truly owning your law firm?</p><p>Contact Atticus to learn how our law firm coaching can help solo and small firm attorneys</p><p>build stronger systems, lead better teams, delegate with confidence, and make smarter</p><p>decisions about growth. From Esq. to Owner is a podcast for law firm owners who want</p><p>practical guidance on law firm leadership, hiring, delegation, operations, marketing,</p><p>profitability, client service, and sustainable growth, so the business supports your life</p><p>instead of running it.</p><p>You can also sign up for the Atticus newsletter to get practical insights on how to grow a</p><p>law firm, strengthen your role as an owner, improve your systems, and build a more</p><p>focused, profitable, and sustainable practice.</p><p>Timestamps:</p><p>00:00 - Introduction </p><p>01:35 - Meet Victor Medina </p><p>04:55 - Why Estate Planning Matters </p><p>07:00 - The Summit </p><p>08:05 - Common Estate Planning Mistakes </p><p>11:20 - Wills vs. Trusts Explained </p><p>14:40 - Protecting Your Family and Assets </p><p>18:10 - Planning Beyond Documents </p><p>21:00 - The Great Practice Breakthrough </p><p>22:05 - Strategies for Business Owners </p><p>26:00 - Probate and How to Avoid It </p><p>30:15 - Tax Planning Considerations </p><p>34:05 - Real Client Stories and Lessons </p><p>38:40 - Practical Steps to Get Started </p><p>42:30 - Biggest Takeaways </p><p>46:20 - Where to Learn More </p><p>49:10 - Closing Thoughts</p>

Episode thumbnail for From Survival Mode to Ownership

July 9, 2026

From Survival Mode to Ownership

<p>The LEI’D Back Life is becoming <strong>From Esq. to Owner</strong>.</p><p>In this episode, Jordan Ostroff explains why the podcast is being renamed and refocused for solo and small firm attorneys who want to stop being buried in the day-to-day and start truly owning their law firm.</p><p>Jordan shares why law firm owners often get stuck in survival mode, making short-term decisions around cash flow, cases, payroll, and client demands instead of building the firm they actually want. He also talks about the foundation owners need before they can think long-term, including referral relationships, early support, better systems, and a clearer vision for their future.</p><p>This episode introduces the bigger mission behind <strong>From Esq. to Owner</strong>: helping lawyers move from practicing law all day to leading a business that supports their clients, their team, and their life.</p><p>If you’re a law firm owner who feels overworked, under-supported, or unsure how to step out of the daily grind, this episode will help you start thinking about what ownership could look like over the next decade.</p><p>---------------</p><p>If Jordan’s conversation about <strong>My Great Life Legacy</strong> got you thinking about your own future, we’d love to help. Reach out to us if you’d like an Atticus expert to walk you through the exercise and help you get clearer about the practice and life you want to build. <a href="https://atticusadvantage.com/contact-us" rel="noopener noreferrer" target="_blank">https://atticusadvantage.com/contact-us</a></p><p>---------------</p><p><strong>Inside This Episode:</strong></p><ul><li>Why <strong>The LEI’D Back Life</strong> is becoming <strong>From Esq. to Owner</strong> and what that shift means for law firm owners</li><li>Why solo and small firm attorneys get stuck in survival mode and struggle to make long-term decisions</li><li>How referrals, support, and systems create a stronger foundation for better choices</li><li>What it means to move from practicing law to truly owning and leading the business</li><li>How to start thinking about your <strong>Great Decade</strong> and the firm, life, and legacy you want to build</li></ul><br/><p>----------------</p><p><strong>Supporting Resources</strong></p><p>Jordan Ostroff: <u><a href="https://atticusadvantage.com/team/jordan-ostroff/" rel="noopener noreferrer" target="_blank">https://atticusadvantage.com/team/jordan-ostroff</a></u></p><p>My Great Life Focus <a href="https://mygreatlifefocus.com" rel="noopener noreferrer" target="_blank">https://mygreatlifefocus.com</a></p><p>The Summit <a href="https://atticussummit.com" rel="noopener noreferrer" target="_blank">https://atticussummit.com</a></p><p>The Great Practice Breakthrough <u><a href="https://atticusadvantage.com/workshops/the-great-practice-breakthrough/" rel="noopener noreferrer" target="_blank">https://atticusadvantage.com/workshops/the-great-practice-breakthrough/</a></u> (Use code PODCAST100 for $100 off registration)</p><p>----------------</p><p>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. <strong>From Esq. to Owner</strong> 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.</p><p>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.</p><p></p><p>Timestamps:</p><p>00:00:00 — Intro: From Esquire to Owner</p><p>00:00:40 — Why the podcast was refocused</p><p>00:01:04 — Why struggling firms can’t make long-term decisions</p><p>00:01:45 — Building a quick referral marketing strategy</p><p>00:02:39 — Hiring support early so you stop doing everything</p><p>00:03:05 — Creating the foundation for long-term thinking</p><p>00:03:32 — My Great Life, My Great Decade, and Legacy</p><p>00:04:07 — Jordan’s obituary exercise and what it revealed</p><p>00:05:26 — Great Practice Breakthrough event details</p><p>00:06:46 — Realizing “lawyer” wasn’t the legacy goal</p><p>00:07:33 — Lifetime roles, goals, and decade planning</p><p>00:08:27 — Lawyer burnout, suicide, and industry impact</p><p>00:10:08 — Why joining Atticus made sense</p><p>00:13:17 — The 2036 great decade challenge</p><p>00:13:48 — Upcoming Atticus Summit event and member reflections</p>

Episode thumbnail for The AMA Episode: Fatherhood, Risk & Running a Business feat. Jordan Ostroff

June 30, 2026

The AMA Episode: Fatherhood, Risk & Running a Business feat. Jordan Ostroff

<p>💥 SPECIAL ANNOUNCEMENT: Host Jordan Ostroff has recently joined Atticus as one of their premier practice advisors! What does that mean for you? You're still getting the same Hawaiian-shirt-wearing, laid-back-life vibes, but now with the powerhouse backing, support, and resources of the incredible Atticus team. All of this is focused on a single mission: helping you run the law firm you've always wanted while living an even better life.</p><p></p><p>🦅 Learn more about Atticus:</p><p>https://atticusadvantage.com</p><p></p><p>Welcome to a highly anticipated, completely unfiltered Ask Me Anything (AMA) masterclass edition of The Laid-Back Life Podcast! In this special solo episode, host Jordan Ostroff takes questions submitted directly by listeners and Atticus members to dive straight into the heart of what modern law firm owners care about most.Jordan strips away the traditional, rigid corporate playbook to share personal stories, tactical frameworks, and pop-culture analogies that will challenge how you look at your calendar, your business connections, and your lifestyle design. From the exact moment he realized he had to step out of constant casework to his unbroken 10,000-daily-step streak, this episode serves as a comprehensive manual for building a profitable firm that wraps entirely around a joyful life.</p><p>🧠 Featured Insights</p><p>✅ The Hot Sauce Awakening: How a surprise pregnancy in 2017 forced Jordan to escape the 100-hour grind and shift into a CEO mindset.</p><p>✅ The Definition of Enough: Why chasing an arbitrary "million-dollar firm" is a trap... and how to scale for true time freedom.</p><p>✅ Top Golf Networking: Why traditional bar events fail, and how casual settings naturally build high-value referral partnerships.</p><p>✅ Leading vs. Lagging Indicators: Lessons from an unbroken daily step streak applied directly to tracking firm growth metrics.</p><p>✅ Business Justice League: Building a corporate dream team by blending radical kindness with historical strategy. </p><p>⏱️ Episode Timestamps</p><p>00:00 - Announcement: Jordan Joins Atticus</p><p>01:48 - Fatherhood Lessons Applied to Business</p><p>04:45 - Balancing Risk Tolerance Scale</p><p>07:52 - Cannon Funerals &amp; Facing Mortality</p><p>12:10 - "Lawyer with a Life" Defined</p><p>16:04 - The Spider-Man Marketing Framework</p><p>19:01 - Grounded Horror &amp; Reality-Based Storytelling</p><p>22:25 - Building a Corporate Justice League</p><p>26:16 - Back to the Future vs. Star Wars</p><p>27:52 - Shifting From Lawyer to CEO</p><p>34:00 - Defining Success &amp; "Enough"</p><p>38:18 - Filtering Out Bad Business Connections</p><p>41:54 - Surprising Referral Partners</p><p>44:39 - 4 Red Flags in Lawyer Networking</p><p>51:32 - Macros, Screen Time &amp; Morning Habits</p><p>53:26 - 75 Hard &amp; Expanding Personal Capacity</p><p>55:42 - Identity &amp; Keeping a 10k-Step Habit</p><p>58:52 - 1 Simple Change to Escape Burnout</p><p></p><p>🦅 Learn more about Atticus:</p><p>https://atticusadvantage.com</p><p></p><p>📅 Book a growth consultation with Jordan Ostroff:</p><p>https://jordanostroff.com/book-an-appointment/</p><p></p><p>📰 Subscribe to our weekly newsletter:</p><p>https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08</p>

90 total episodes available

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Jeremy Danilson

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Tracey Goodwin

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Valerie Fenchel

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Kendra Niiro

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Morris Lilienthal

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Jenn Gore

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Matt Burke

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What is 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.

How often does this podcast release new episodes?

This podcast updates daily.

Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

Information about guest appearances is not available.

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