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

On this episode of The Leid Back Life , we’re talking about how to actually plan your content so you’re not winging every recording. Whether it’s for your podcast, your firm’s social media, or your next big launch—this is how to prep with purpose. If your content plan is “hit record and hope,” this one’s for you. I’ll walk you through how I plan my podcasts, reels, and everything else before I eve...

This special episode of The Lei’d Back Life features Jordan Ostroff diving into the concept of Mind Like Water —and how it can completely transform the way you run your law firm and your life. Jordan breaks down how to shift out of reaction mode, build systems that actually reduce stress, and create space for focus, flow, and freedom. Whether you’re feeling overwhelmed or just want more clarity in...

Imagine a business that runs and grows while you're on vacation. Sounds like a dream, right? In this episode, Jordan sits down with Jayden Doye CPA, entrepreneur, and the master of taking real, unplugged vacations without sacrificing revenue. Whether you’re a lawyer chained to your calendar or a business owner who hasn’t taken a real break in years, this episode is your permission (and game plan)...

On this episode of The Lei’d Back Life , Jordan Ostroff sits down with entrepreneur and travel-lover Rory Safir to talk about building a business that doesn’t just pay the bills—it funds your freedom. Rory dives into how to create systems that support your lifestyle, why true success means stepping out of the office, and what mindset shifts are needed to build a business that runs without you cons...

What does it look like to build a business with your family—not just for them? In this episode of The Lei’d Back Life Podcast , I sit down with Adam Williams to talk about how he’s involving his kids in entrepreneurship, what it takes to build a business legacy at home, and why turning your firm into a “family business” is about way more than just a name on the door. We dive into: How to raise fut...

Want to make work optional? 👀 Darren Wurz breaks it all down on this episode of The Lei’d Back Life!" We’re talking financial freedom, intentional living, and what it really takes to design a life where work isn’t the boss of you. Ready to work optionally? Visit us at ⁠jordanostroff.com⁠

On this episode of The Lei’d Back Life , I’m joined by Rachel McGary to break down how systems aren’t just for business, they’re the foundation for a better life. If you're tired of the chaos and ready to run things smoother at work and at home, this one’s for you. 👉 Ready to upgrade your systems and your life? Visit us at jordanostroff.com for more.

This week on The LEI'D Back Life , I’m hanging out with Billie Tarascio — founder of Modern Law and a true pioneer when it comes to innovating law firms. Billie’s background is packed with accolades: she’s not just an experienced family law attorney but also a tech-savvy entrepreneur who’s reshaping how law firms operate. You can find more about her at https://mymodernlaw.com . In this episode, Bi...

In this episode, I’m joined by Seth Price, CEO of BluShark Digital and founding partner of Price Benowitz LLP. Seth has helped hundreds of law firms grow their online presence and become lead-generating machines, and we dig deep into how he balances running multiple companies without burning out. We talked about the mindset shifts that helped him go from lawyer to CEO, why delegation is essential...

Today, I’m joined by Brett Trembly, attorney, entrepreneur, and co-founder of Get Staffed Up, to talk about building your business with assistants. Brett’s mission is to help business owners delegate more, do more, and grow faster by offloading the stuff that’s not the best use of their time. With years of experience running both his own law firm and a staffing company, Brett knows firsthand how t...

In this episode of The LEI'D Back Life, I sat down with Ana Juneja, an award-winning intellectual property attorney and the founder of Ana Law, the first and only law firm that offers flat-fee, 100% guaranteed patent, trademark, and copyright services. Her social media following is huge, but what really sets her apart is how she shows up authentically online… typos, flubs, and all. We talked a...

Today, I’m chatting with Christopher Nicolaysen, founding partner and CEO at Springs Law Group and a total pro when it comes to helping business owners build a better life through smarter systems and better boundaries. We dive into the ups and downs of entrepreneurship, the emotional rollercoaster of running your own firm, and why creating real work-life balance isn’t just about taking vacations....

In this episode of The LEI'D Back Life, I am joined by the CEO of GOLDLAW: Craig Goldenfarb. He’s made a serious shift toward prioritizing what really matters: life. We dive into his journey of going from ‘business first’ to intentionally redesigning his life around what fills his cup—family, travel, and meaning.  One of the coolest things? His wife is now co-speaking with him on work-life bal...

This week on The LEI'D Back Life, I sat down with Jennifer Gillman, the founder of Gillman Strategic Group, LLC, who’s helping lawyers live better lives on their terms. Jennifer’s built her entire business around helping lawyers move from burnout to balance, matching them with law firms that actually get work-life harmony (yes, they exist!) We talked about what makes lawyers stay too long at t...

In this episode, I sat down with Gyi Tsakalakis—lawyer-turned-digital marketer and the founder of AttorneySync—to talk all things marketing, mindset, and making real connections. We discussed the marketing traps lawyers fall into, the importance of authenticity in building your brand, and why “shiny object syndrome” can wreck your long-term success.  Gyi also dropped gems on how to pick the right...

This week, we're pausing from guest interviews and diving into something I believe is essential for building a business and life you love: the organization of a great life. Inspired by the concept of “mind like water” from David Allen’s Getting Things Done , I break down how to actually live with a calm, focused, and productive mindset. I share the real structure I use to manage multiple busin...

In this episode, I chat with Beau Atkins, founder of Evolve Law and a family law attorney who’s flipping the traditional firm model on its head. We dig into Beau’s personal and professional transformation, starting with the realization that he was investing more in his business than in himself. From there, Beau walks us through how he began building his life first, from flat fee billing to emotion...

In this episode, I sit down with the brilliant Andie Herrick—an executive and systems strategist who helps people create sustainable success by designing lives and businesses that actually work for them. She is the founder and co-owner of Untied Business Solutions firm Her superpower is helping people bridge the gap between where they say they want to go and what they’re actually doing day to day....

In this episode of the LEI'D Back Life, I sit down with Russell Knight, an experienced family law attorney with a unique approach to running his practice. We dive into the realities of growing a law firm, the challenges of balancing work and personal life, and how marketing plays a crucial role in building a successful legal business. Russell shares his insights on standing out in a crowded ma...

In this episode, I sit down with Ron Payne, an attorney who recently transitioned from running his own firm for 13 years to joining a new law firm. We dive into what that transition has been like—shifting from being fully self-employed to an "eat-what-you-kill" model where he has support but still manages his own business. Ron shares the challenges of adapting to a new work environment,...

In today’s episode, I sit down with Kristen David, the powerhouse behind Up Leveling Your Business, a coaching group designed to help business owners create scalable, sustainable success. Kristen splits her time between the Pacific Northwest and France, proving that you don’t have to be tied to one location to run a thriving business. We explore what it takes to build a company that operates smoot...

In today’s episode of The LEI’D Back Life, I sat down with Rho Thomas, attorney, financial coach, and host of the Personal Finance for Lawyers podcast, to talk about something every business owner needs to master—money and mindset. We dive into financial freedom, smart money management, and how entrepreneurs can take control of their finances instead of letting their finances control them. Rho sha...

In this episode of the LEI’D Back Life, I sit down with Elise Buie, founder of Elise Buie Family Law, to talk about the balancing act of entrepreneurship, leadership, and life outside of work. We dive into scaling a business while maintaining personal freedom, how to build a strong team, and the mindset shifts that make all the difference. Elise shares her experiences in growing her law firm, the...

In this episode of The LEI’D Back Life, I sit down with Josh Pies, the Hippie Capitalist at C47 Films Digital Studios and host of the Bootstrapped Unicorns Podcast, to talk about one of the biggest challenges in business—how to scale without losing your sanity. We dive into delegation, automation, and the key systems that allow entrepreneurs to free themselves from the daily grind. Josh shares his...

In this episode of the LEI'D Back Life, I sit down with Josh Wilson, a licensed real estate broker, investment banker, and host of The Deal Scout podcast, to talk about the unexpected lessons we can learn from media and storytelling. Josh shares insights on finding inspiration in everyday moments and how embracing humor and perspective can transform your approach to life and business. We explo...