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Lawyer with a Life - Jordan Ostroff
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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.

  1. 3D AGO

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

    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 effortless instead of exhausting, how to create a clear message clients remember, and how to design content that supports work life balance while still driving revenue. It’s a practical look at building a profitable law firm brand with consistency, positioning, and trust that compounds over time. 📰 Subscribe in our weekly newsletter:https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 📚 Read the roadmap to a better firm:Love Your Law Firm: A Roadmap to the Law Firm You Always Wanted (2nd Edition)https://amzn.to/4a3ziB4 🌺 Join The Luau Group:https://app.lawmatics.com/forms/share/782ca378-c8ab-42d9-8b05-19c62f932f15 🧭 Grab The CARPE Hiring Playbook:https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27 🌐 Visit my website:https://www.jordanostroff.com. 🔗 Find the next smart move for your firm:https://linktr.ee/LawyerWithALife 📂 Grab my free resources to run your firm better:https://jordanostroff.com/resources/ 📅 Ready for direct help? Book a consult:https://jordanostroff.com/book-an-appointment/ 👥 Facebook group:https://www.facebook.com/groups/forlawyersbylawyers

    45 min

  2. FEB 10

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

    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 who implements, by building simple execution rules, tightening accountability, and creating follow through systems that hold up when you are busy. If you want better productivity, stronger law firm systems, and real accountability without burning yourself out, this conversation is for you. 🧭 Link in bio for everything:https://linktr.ee/LawyerWithALife 🧰 Free resources and weekly newsletter:https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 📚 Read the roadmap to a better firm:Love Your Law Firm: A Roadmap to the Law Firm You Always Wanted (2nd Edition)https://amzn.to/4a3ziB4 🌺 Join The Luau Group:https://www.facebook.com/groups/forlawyersbylawyers 🎧 Listen to the podcast on Spotify:https://open.spotify.com/show/7L8yJ0rRL66Nrjfe5uX418 🍎 Listen to the podcast on Apple Podcasts:https://podcasts.apple.com/us/podcast/the-leid-back-life-loving-entrepreneurship-and/id1782958064 ▶️ Watch the podcast on YouTube:https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe 🌐 Visit the website:https://www.jordanostroff.com📅 Ready for direct help? Book a consult:https://jordanostroff.com/book-an-appointment/

    56 min

  3. FEB 3

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

    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 actually performs. They break down how values become practical decision tools under pressure, how transparency and anonymous feedback keep teams bought in as you scale, and why strong culture turns into law firm marketing without the cringe because clients leave reviews and referrals when the experience is consistently great.📅 Ready to book a consult? Click here:https://jordanostroff.com/book-an-appointment/🔗 Linktree:https://linktr.ee/LawyerWithALife📰 Subscribe in our weekly newsletter:https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08📚 Read the roadmap to a better firm:Love Your Law Firm: A Roadmap to the Law Firm You Always Wanted (2nd Edition)https://amzn.to/4a3ziB4🌺 Join our Facebook group:https://www.facebook.com/groups/forlawyersbylawyers🌐 Visit my website:https://www.jordanostroff.com

    54 min

  4. JAN 27

    How Great Partners Make Everything Lighter

    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 when stress is high, and why a strong relationship is a competitive advantage for entrepreneurs. If you have been wondering how to grow a business while staying connected at home, you will walk away with practical ideas you can use this week. 🔗 Link in bio for everything:https://linktr.ee/LawyerWithALife 🧭 Free resources to build a life first law firm:https://linktr.ee/LawyerWithALife 📅 Book coaching with Jordan:https://www.jordanostroff.com 📰 Subscribe in our weekly newsletter:https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 📚 Read the roadmap to a better firm:Love Your Law Firm: A Roadmap to the Law Firm You Always Wanted (2nd Edition)https://amzn.to/4a3ziB4 🌺 Join The Luau Group:https://www.facebook.com/groups/forlawyersbylawyers 🧭 Grab The CARPE Hiring Playbook:https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27 🎧 Listen to our podcast on Spotify:https://open.spotify.com/show/7L8yJ0rRL66Nrjfe5uX418 🍎 Listen on Apple Podcasts:https://podcasts.apple.com/us/podcast/the-leid-back-life-loving-entrepreneurship-and/id1782958064 ▶️ Watch the podcast on YouTube:https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe 🌐 Visit my website:https://www.jordanostroff.com

    51 min

  5. JAN 20

    How to Turn Learning Into Real Change

    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 reshape your week, and behavior change you can sustain without burning out. You will learn✅ Why learning can feel productive while keeping you stuck✅ How to turn one insight into a weekly habit✅ A simple filter for what to ignore and what to implement✅ How to build a great life without waiting for the perfect plan If you want your next book or podcast to actually move the needle, start here. 🔗 Find the next smart move for your firm:https://linktr.ee/LawyerWithALife 📂 Grab my free resources to run your firm better:https://jordanostroff.com/resources/ 📅 Ready for direct help? Book a consult:https://jordanostroff.com/book-an-appointment/ 📰 Subscribe in our weekly newsletter:https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 📚 Read the roadmap to a better firm:Love Your Law Firm: A Roadmap to the Law Firm You Always Wanted (2nd Edition)https://amzn.to/4a3ziB4 🧭 Grab The CARPE Hiring Playbook:https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27 🎧 Listen to our podcast on Spotify:https://open.spotify.com/show/7L8yJ0rRL66Nrjfe5uX418 🍎 Listen on Apple Podcasts:https://podcasts.apple.com/us/podcast/the-leid-back-life-loving-entrepreneurship-and/id1782958064🌐 Visit my website:https://www.jordanostroff.com.

    52 min

  6. JAN 15

    How I Work 3 Days a Week Without Losing Revenue

    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 actually moved the needle, the systems and processes that stopped the firm from depending on his constant availability, and the time management for lawyers mindset shift that makes the whole thing sustainable. If you are tired of feeling like you have to earn rest, this is your playbook for building a life first firm that still performs. 📅 Ready for direct help? Book a consult:https://jordanostroff.com/book-an-appointment/ 🔗 Find the next smart move for your firm:https://linktr.ee/LawyerWithALife 📂 Grab my free resources to run your firm better:https://jordanostroff.com/resources/ 📰 Subscribe in our weekly newsletter: ⁠https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08⁠ 📚 Read the roadmap to a better firm:Love Your Law Firm: A Roadmap to the Law Firm You Always Wanted (2nd Edition) ⁠https://amzn.to/4a3ziB4⁠ 🧭 Grab The CARPE Hiring Playbook: ⁠https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27⁠

    50 min

  7. JAN 6

    How to Finally Keep Your New Year’s Resolutions feat. Jordan Ostroff

    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 tracking and simple calendar scheduling triggers so your plan survives real life. If you have ever started strong and fallen off, this process gives you a repeatable way to build consistency and keep momentum all year. 🔗 Find the next smart move for your firm:https://linktr.ee/LawyerWithALife 📂 Grab my free resources to run your firm better:https://jordanostroff.com/resources/ 📅 Ready for direct help? Book a consult:https://jordanostroff.com/book-an-appointment/ 📰 Subscribe in our weekly newsletter:https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 📚 Read the roadmap to a better firm:Love Your Law Firm: A Roadmap to the Law Firm You Always Wanted (2nd Edition)https://amzn.to/4a3ziB4 🧭 Grab The CARPE Hiring Playbook:https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27 🌐 Visit my website:https://www.jordanostroff.com

    29 min

  8. 12/30/2025

    Best of 2025: The Most Rewatched Law Firm Advice (The Lei’d Back Life)

    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 owners who want practical advice without the fluff. We pulled the strongest guest takeaways on law firm growth, delegation, marketing, and work life balance so you can stop carrying everything yourself and start building a life first business that still performs. Save this compilation for the days you need a fast reset, a better system, or one simple next step. 📰 Subscribe in our weekly newsletter:https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08📚 Read the roadmap to a better firm:Love Your Law Firm: A Roadmap to the Law Firm You Always Wanted (2nd Edition)https://amzn.to/4a3ziB4🌺 Join The Luau Group:https://app.lawmatics.com/forms/share/782ca378-c8ab-42d9-8b05-19c62f932f15🧭 Grab The CARPE Hiring Playbook:https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27🎧 Listen to our podcast on Spotify:https://open.spotify.com/show/7L8yJ0rRL66Nrjfe5uX418▶️ Watch the podcast on YouTube:https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe🍎 Listen on Apple Podcasts:https://podcasts.apple.com/us/podcast/the-leid-back-life-loving-entrepreneurship-and/id1782958064🔗 Linktree for everything:https://linktr.ee/LawyerWithALife🌐 Visit my website:https://www.jordanostroff.com

    36 min
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About

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.

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