Lawyer with a Life - Jordan Ostroff

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

Business EN ↓ 89 episodes

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.

Author

Lawyer with a Life - Jordan Ostroff

Category

Business

Podcast website

www.jordanostroff.com

Latest episode

Jul 9, 2026

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Episodes

From Survival Mode to Ownership 09.07.2026

The LEI’D Back Life is becoming From Esq. to Owner . 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. Jordan shares why law firm owners often get stuck in survival mode, making short-term decisions around cash flow, cases, payroll, and clie...

The AMA Episode: Fatherhood, Risk & Running a Business feat. Jordan Ostroff 30.06.2026

💥 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...

Billing Tips For a Great Firm and An Even Better Life feat. Jyl Warwick and Karyn Campbell 23.06.2026

💥 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...

Designing Your Firm Around Your Life feat. Cristina Hughes 16.06.2026

💥 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...

The Most Important Piece of Advice You’ll Hear This Mid Year 09.06.2026

💥 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...

Getting Your Story Out There feat. Jonathan White 03.06.2026

💥 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...

AI That Works for Your Firm So You Can Have a Life feat. Dan Schnurbusch and Jordan Ostroff 27.05.2026

Is your law firm's tech stack actually working for you... or are you working for it? In this special webinar-turned-podcast masterclass, discover how modern attorneys are moving past basic AI prompts to build custom firm infrastructure that runs your practice while you design your life. Jordan is joined with Dan Schnurbusch. Dan is a Missouri-based probate attorney and legal tech innovator who...

Networking Your Way to a Great Life 20.05.2026

Are you tired of handing out business cards like confetti and getting zero client referrals in return? In this episode of The Leid Back Life Podcast im joined with Delisi Friday. Delisi is the founder of First Call Friday and host of the From Coffee to Cases podcast. Having learned referral marketing at just 14 years old, she famously helped scale a personal injury law firm from 7 to 8 figures pur...

Using AI to Live the Life We Want: The Blueprint for a Truly Great Life feat. Colin Levy 13.05.2026

"Life is short... and you don't know exactly how much time you have". Welcome to another episode of The Lei’d Back Life podcast with host Jordan Ostroff. Joining us today is phenomenal guest Colin Levy, General Counsel at Malbeck, adjunct professor at Albany Law School, and author of The Legal Tech Ecosystem , Contract Life Cycle Management for Dummies , and the Handbook of Legal Tech . Colin spec...

Birthday Special Episode: How to Find Fun and Happiness in Life feat. Jordan Ostroff 06.05.2026

In this special birthday episode of The Lei’d Back Life , Jordan Ostroff dives into the science and strategy of joy. Most people aren't miserable because life is impossible—they're miserable because they're lonely and living on autopilot. Jordan explains how to incorporate connection into your existing schedule, showing that true professional success is built on a foundation of personal fulfillmen...

We is Stronger Than Me: Collaboration for a Great Life feat. Robert Hana 29.04.2026

Can collaboration lead to market domination? Robert Hanna thinks so. In this episode, "We is Stronger Than Me: Collaboration for a Great Life," the CEO of KC Partners and host of the Legally Speaking podcast breaks down how he built a top 1% global podcast and a world-class legal recruiting firm through the power of partnership. We discuss the mindset shift required to see competitors as collabora...

Achieving a Mind Like Water: Mastering David Allen’s GTD feat. Adam Kavulic 22.04.2026

"It is better to make full progress on five things than it is to make sort of progress on 50." In this episode of The Lei’d Back Life , Jordan Ostroff is joined by Adam Kavulic, a teacher-turned-REALTOR who has mastered the art of digital organization. They dive into the Getting Things Done (GTD) system and how to stop storing tasks in your brain. Learn why 100% faith in your calendar is the key t...

Focus 90 and the Future of Your Firm feat. Corine Rogers 15.04.2026

Are you tired of waking up at 1:00 AM worrying about dropped balls and silent bottlenecks in your law firm? In this episode of The Lei’d Back Life Podcast, Jordan sits down with Corine Rogers, founder of Simple Smart Solo, to discuss the ultimate operational cure: The Focus 90 meeting. Corine breaks down exactly how to move your firm from chaos to control in just 90 minutes a week. Learn who needs...

The Ideal Month Blueprint: How to Gain 4 Extra Weeks of Vacation a Year 08.04.2026

In this special episode of The Lei’d Back Life Podcast, Jordan reveals the "Ideal Month Blueprint." If your calendar looks like a game of Tetris gone wrong, it’s time to move away from the to-do list and into a structured 28-day cycle. Jordan shares how to protect your "Anchor Events"—the things that matter most, like family, health, and sleep—while still running a high-performing firm. Learn why...

Finding Your Ideal Client: How to Build a Law Firm You Love 01.04.2026

Are you tired of the grind? In this episode of The Lei’d Back Life , Jordan Ostroff discusses the critical shift from being a generalist to finding your ideal client. This webinar special is designed for lawyers who want to regain control of their time and build a more profitable, less stressful practice. (00:00) - Introduction to the Finding Your Ideal Client Webinar (02:45) - The link between cl...

The Deathbed Regret: Stop Faking Your Life feat. Gordon Firemark 25.03.2026

Stop acting like a robot in a suit. Most lawyers are so busy projecting what they think a lawyer should look like that they forget to be the person clients actually want to hire: themselves. Joining me today is Gordon Firemark , also known as "The Podcast Lawyer." Gordon has spent three decades at the intersection of entertainment and law. We’re diving deep into how to build a personal brand that...

Challenging the "Rules" of Law with Jen Lee 18.03.2026

"Lawyers think creativity is for actors and theater majors—they're wrong." In this episode of The Lei’d Back Life , host Jordan Ostroff sits down with Jen Lee, the bankruptcy nerd turned "Rebel Esquire," to discuss the power of professional disruption. If you’re tired of the 1980s-style firm management and want a better way to run your practice, Jen is here to show you how to turn off your "lawyer...

The Hidden Ego That’s Destroying Your Business (Allison Williams) 11.03.2026

Still trying to do everything yourself because no one can do it “right”?That mindset might be the exact thing keeping your business and your life stuck. In this episode, Jordan and Allison break down why delegating tasks is not enough, how mental load keeps law firm owners trapped, what real ownership looks like inside a team, and how to build systems that create more money, more free time, and le...

The Secret to Loving Work Again feat. John Strohmeyer 04.03.2026

Tired of building a successful business that quietly drains your life? What if the real win isn’t more revenue but designing work that actually supports how you want to live? This conversation is for entrepreneurs, law firm owners, and growth minded professionals who are chasing business growth but feel the tension of work life balance slipping away. We dive into what it really means to work smart...

The Real Reason Lawyers Burn Out 25.02.2026

You built the firm. You hit the revenue. So why does it still feel empty? Law firm burnout isn’t about working too hard. It’s about missing the three drivers of real motivation: autonomy, mastery, and purpose. In this conversation, Daniel Pink breaks down the science behind motivation and why so many successful law firm owners feel stuck, unfulfilled, or quietly exhausted. If you’re a lawyer tryin...

Build a Profitable Brand That Prints Clients (Without More Work) feat. Victoria Emmot 18.02.2026

Does your “brand” feel like a second full time job you never asked for? Here’s how to build a profitable name people trust without sacrificing your life to do it. If you’re a law firm owner or service professional trying to grow without living online, this conversation breaks down how to build a personal brand that actually converts. Victoria Emmot shares what makes law firm marketing feel effortl...

Motivation Is Overrated. This Is How You Actually Execute. feat. Charley Mann 11.02.2026

Why do smart law firm owners keep “knowing” what to do but never doing it? Charley Mann breaks down how to become the kind of person who implements, so your systems actually get used and your goals stop living in a notebook. Most law firm owners are not lacking information, they are stuck in the gap between planning and executing. In this episode, Charley Mann walks through how to become a person...

Define Your Great Life Before You Grow Your Firm feat. Kevin Daisey 04.02.2026

Still chasing “success” but somehow feeling more trapped every year? What if the problem is you never defined what freedom actually looks like. This conversation is for law firm owners who want real freedom, not just a bigger calendar. Jordan Ostroff and Kevin unpack how defining a great life first changes everything, from core values and culture to hiring A players and building a remote team that...

How Great Partners Make Everything Lighter 28.01.2026

Trying to build a firm and keep your relationship strong at the same time? If your success is creating tension at home, this conversation is for you. This episode is for law firm owners and ambitious lawyers who want real work life balance without sacrificing their marriage or partnership. Jordan and Heather Trick Ostroff talk about what support looks like behind the scenes, how to communicate whe...

How to Turn Learning Into Real Change 21.01.2026

Ever feel like you are learning nonstop but nothing is changing? Jonathan Paul breaks down how to turn information into a great life you actually live. This conversation is for high performing lawyers and business owners who are drowning in podcasts, books, and advice but still feel stuck in the same patterns. We talk about personal growth that turns into action, learning habits that actually resh...

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