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

Still running your firm like your calendar is the business plan? I cut down to a three day workweek and the firm got better, not worse. This episode is for lawyers who want real law firm work life balance without torching revenue, ghosting clients, or dumping stress on the team. Jordan walks through what changed when he committed to a three day workweek, including the delegation decisions that act...

Why do your New Year’s resolutions die by February even when you “really mean it”? It is not motivation. It is the missing system that makes follow through automatic. This episode is for busy lawyers and law firm owners who want New Year’s resolutions that actually stick without relying on willpower. Jordan walks through goal setting using SMART goals, then shows how to turn those goals into habit...

Feel like you consumed a ton of content in 2025 but you’re still stuck in the same problems? Best of 2025 highlights for law firm growth, delegation, marketing, and work life balance. Ready to turn the best ideas from this episode into a real plan for your firm? Book a consult here: https://jordanostroff.com/book-an-appointment/This Best of 2025 highlights episode is for lawyers and law firm owner...

Feel exhausted but still telling yourself you should be able to push through? Burnout isn’t weakness, and pretending it is keeps lawyers stuck longer than they need to be. Burnout shows up differently for lawyers, but the root cause is often the same: constant pressure, blurred boundaries, and the belief that rest has to be earned. In this episode of The Lei’d Back Life, Jordan sits down with Jess...

What if AI could actually make healthy decisions easier instead of adding more noise to your life? In this episode of The Lei’d Back Life , I sit down with Jeremy Danilson to explore what it looks like to create an AI-powered nutritionist that supports real people with real schedules. We talk about reducing decision fatigue, building healthier habits without perfectionism, and using technology as...

In this episode of The Leid Back Life Podcast I sit down with Tracey Goodwin to talk about something every lawyer and business owner struggles with spending more time in your genius instead of drowning in everything else. Tracey breaks down how your voice your message and your connection to your own work shape the results you get not just on stage but in every conversation you have. If you have ev...

In this episode of The Lei’d Back Life, I sit down with Valerie Fenchel to talk about what it actually takes to become a better leader so you can build a better business. We dig into the mindset shifts, the systems, and the real world examples that help you lead your team without burning yourself out in the process. If you want a business that supports your life instead of consuming it, this conve...

In this episode of The Lei’d Back Life Podcast I sit down with Kendra Niiro to explore why a great life becomes the foundation of a great brand. Kendra breaks down how your daily choices, energy, and alignment shape the way your business shows up in the world. This conversation is all about building a life first business that naturally strengthens your brand without forcing anything. If you want y...

This week on The Leid Back Life Podcast I sat down with Morris Lilienthal to talk about how being an intentional parent directly shapes the way you lead, hire, and grow your business. Morris shares what he learned from balancing a thriving legal career with raising a family, and how those lessons translate into better decision making, healthier leadership, and a more grounded approach to entrepren...

In this episode of The Lei’d Back Life Podcast , Jordan Ostroff sits down with leadership and mindset coach Jenn Gore to talk about what it really means to live to your highest potential. They dive into purpose, fulfillment, and how to align your work with what energizes you instead of what drains you. Jenn shares her insight on how to know when you’re on the right track, how to find flow in your...

In this episode of The Lei’d Back Life , I’m joined by Matt Burke to talk about using KPIs as a tool for better problem solving in both business and real life. Most people think KPIs are just numbers for spreadsheets. Matt shows how they can actually become clarity tools. When you track the right data, you stop guessing and start making decisions that move the needle in a meaningful way. We get in...

In this episode of The Lei’d Back Life Podcast , I sit down with Stacey Brown Randall , author of Generating Business Referrals Without Asking and one of the best minds out there on building a business that grows through relationships—not cold leads. We talk about how to create a referable client experience that turns happy clients into active advocates for your firm. Stacey shares simple, repeata...

In this episode of The Lei’d Back Life Podcast , I sat down with Hunter Garnett to talk about what it really means to share your authentic self as a lawyer and leader. We dove into how honesty, vulnerability, and self-awareness can completely shift your firm’s culture and your happiness. Hunter’s story is one every attorney should hear if they’re tired of pretending to fit someone else’s mold. If...

In this episode, we dive deep into what it really takes to build momentum in both your business and your personal life. Neal shares how the smallest actions, when done consistently, can lead to massive long-term growth. We break down how lawyers and entrepreneurs can build systems, not just willpower, to create real change. If you’ve ever felt stuck doing “busy work” instead of impact work , this...

Are you constantly feeling like there aren’t enough hours in the day? ⏰ In this episode of The Lei’d Back Life , Jordan Ostroff breaks down The Time Audit — a simple but powerful process that helps you uncover where your time actually goes, identify energy drains, and rebuild your schedule around what truly matters. You’ll learn how to: ✅ Track every minute without losing your mind ✅ Eliminate...

What makes a business thrive isn’t just strategy — it’s culture and the people you bring on board . In this episode of The Lei’d Back Life , host Jordan Ostroff sits down with Erin Andersen to dive deep into what it really takes to build a team that fuels both success and happiness. From hiring the right people to cultivating a workplace where everyone thrives, Erin shares practical insights every...

What if building a thriving business didn’t mean sacrificing your lifestyle? In this episode of The Lei’d Back Life , I sit down with Laura Cowan to talk about what I call The Lifestyle Revolution . Laura shares how she redefined success on her own terms—prioritizing health, freedom, and purpose while still growing her business. We dive into practical strategies for lawyers and entrepreneurs who a...

Welcome to a special AMA episode of the Lei’d Back Life Podcast 👨‍👦💼🎙️ — where I dive into your questions on fatherhood, risk, and running a business. I’ll share what it’s really like to balance being a dad, leading a law firm, and building multiple businesses while still making time for the life I want to live. If you’ve ever wondered how to juggle family, business, and risk-taking without bur...

What if marketing wasn’t just about growth, but also about creating joy—for you, your clients, and your business? In this episode of The Lei’d Back Life , Jordan Ostroff sits down with Joshua Baron to explore how law firm owners and entrepreneurs can build marketing strategies that fuel both happiness and success. Joshua shares insights on aligning your business goals with personal fulfillment, bu...

I’m joined by Bryan Haskins on The Lei’d Back Life to dig into The Benefits of Being You. 🌴 Bryan’s story is proof that authenticity isn’t just about feeling good—it’s about building stronger connections, attracting the right clients, and creating a life that actually fits. We’ll talk about why leaning into who you are is one of the best decisions you can make, both personally and professionally....

AI isn’t just the future anymore—it’s here, shaping how we work, lead, and live right now. In this episode, Jordan sits down with Carolyn Elefant—lawyer, author, and founder of MyShingle.com —to unpack the real, practical impact of AI in today’s business world. From running a law firm to building a life-first business, Carolyn brings her sharp insights on how AI tools can transform efficiency, cre...

In this episode of The Lei’d Back Life , I’m joined by David Lawson to talk about what it really takes to become a resilient business owner. We dig into the challenges, setbacks, and pivots that every entrepreneur faces, and how resilience is the skill that keeps you moving forward when things get tough. If you’ve ever wondered how to build a business that doesn’t just survive but thrives, this co...

Running a business isn’t just about titles, revenue, or strategy — it’s about balance, leadership, and building a life you actually want to live. In this episode, I break down what it really means to be a CEO, the shifts you need to make to lead effectively, and how to run your firm without running yourself into the ground. Whether you’re a lawyer, business owner, or just someone dreaming of stepp...

In a world where AI is everywhere, how do we keep our human connections strong? Mike Whelan joins me to talk about the balance between tech and relationships, and why human connection still matters more than ever. We’ll cover: ✅ How AI is changing communication ✅ Why human touchpoints are irreplaceable ✅ Practical tips to stay connected in a digital-first world Listen in, share your thoughts, a...

In this special Q&A episode of The Lei’d Back Life , Jordan Ostroff sits down with estate planning attorney and financial expert Victor Medina to talk all things firm ownership, lifestyle design, and what it really takes to build a business that supports your life—not one that runs it. We’re answering real questions from real lawyers—on hiring, marketing, money, and mindset. If you’re tired of...