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The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
Lawyer with a Life - Jordan Ostroff
61 episodes
1 week ago
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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Entrepreneurship
Business
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All content for The LEI'D Back Life: Loving Entrepreneurship and Improving Daily is the property of Lawyer with a Life - Jordan Ostroff and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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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Entrepreneurship
Business
Episodes (20/61)
The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
Burnout Isn’t a Personal Failure for Lawyers (Jess Birken)

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 Birken to unpack what lawyer burnout actually is, why traditional work life balance advice fails, and how chronic stress quietly erodes both performance and personal life.


This conversation is for attorneys who feel overwhelmed, tired of white knuckling their practice, and ready for practical ways to set boundaries and rebuild energy without burning everything down.


▶️ Watch the podcast on YouTube:https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe

🎧 Listen 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

📘 Read the book:Love Your Law Firm: A Roadmap to the Law Firm You Always Wanted (2nd Edition)https://amzn.to/4a3ziB4📰 Subscribe to the weekly newsletter:https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08

🌺 Join The Luau Group (life-first lawyers only):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 Jordan’s site:https://www.jordanostroff.com

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1 week ago
52 minutes 32 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP59: Creating an AI Nutritionist feat. Jeremy Danilson

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 a tool rather than another source of overwhelm.

This is not a hype-driven AI conversation. It’s a practical look at how smart systems can improve daily life, especially for busy professionals who want better outcomes without sacrificing their time or sanity. If you’re curious about blending health, technology, and lifestyle design in a realistic way, this episode is for you.

🎧 Listen and watch the episode:

🎧 Listen on Spotify
https://open.spotify.com/show/7L8yJ0rRL66Nrjfe5uX418

▶️ Watch 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

📰 Subscribe to the weekly newsletter
https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08

📚 Read 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

🌐 Explore more resources
https://linktr.ee/LawyerWithALife

Show more...
2 weeks ago
59 minutes 25 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP59: Spending More Time In Your Genius feat. Tracey Goodwin

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 ever felt like you are capable of more but constantly pulled away from the work that really lights you up this conversation will give you the clarity and tools to start shifting back toward your zone of genius.

Tracey is the CEO of Captivate The Room and an internationally known expert on voice and communication. She has helped hundreds of thousands of people around the world unlock the real power of their message and this episode will show you why her approach changes the way you think about speaking leading and showing up.

Watch the full episode to learn how to reconnect with the work that fuels you build a business that supports your life and communicate with more confidence and impact.


Links and Resources

🎧 Listen to our podcast on Spotify:
https://open.spotify.com/show/7L8yJ0rRL66Nrjfe5uX418


▶️ Watch the full podcast playlist on YouTube:
https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe


📰 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


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3 weeks ago
57 minutes 44 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP58: Becoming a Better Leader to Lead a Better Business feat. Valerie Fenchel

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 conversation is a must listen.

📰 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)

🌺 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

🌐 Visit my website:
https://www.jordanostroff.com



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4 weeks ago
55 minutes 37 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP57: A Great Life is a Great Brand featuring Kendra Niiro

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 your marketing to feel more like you this episode will show you how to get there. Settle in for a powerful reminder that your best branding strategy starts with your best life.


📰 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://www.amazon.com/dp/B0FTSM619L


🌺 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


🌐 Visit my website:https://www.jordanostroff.com

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1 month ago
54 minutes 50 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP56: How Being a Great Parent Makes You a Better Business Owner feat. Morris Lilienthal

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 entrepreneurship.


What we cover in this episode

✅ Building a business that reflects your family values

✅ The habits great parents and great leaders share

✅ Why patience and presence matter more than tactics

✅ How parenting teaches long term thinking in business

✅ Practical ways to apply these lessons inside your firm


📰 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://www.amazon.com/dp/B0FTSM619L


🌺 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

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1 month ago
56 minutes 59 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP55: Living to Your Highest Potential feat. Jenn Gore

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 purpose, and how to stop chasing validation so you can focus on what really matters.

If you’ve ever felt stuck or unsure how to bridge the gap between ambition and alignment, this conversation is your sign to start living life fully and not just working through it.

📰 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://www.amazon.com/dp/B0FTSM619L

🌺 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

🌐 Visit my website:
https://www.jordanostroff.com

Show more...
1 month ago
53 minutes 27 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP54: KPI's for Focused Problem Solving in Business and Life feat. Matt Burke

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 into:
✅ How to identify which metrics actually matter
✅ Why tracking less data can create more clarity
✅ How KPIs help reduce stress and emotional decision making
✅ Using simple measurement to invest your time, money, and energy more intentionally
✅ Applying the same approach to relationships, health, and personal life design

If you’ve ever felt overwhelmed by too many priorities or stuck solving the same problems again and again, this conversation will help you focus on what actually matters.


📰 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://www.amazon.com/dp/B0FTSM619L

🌺 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

🌐 Visit my website:
https://www.jordanostroff.com

Show more...
1 month ago
49 minutes 31 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP53: The Referable Client Experience Q & A featuring Stacey Brown Randall

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, repeatable strategies you can use to earn referrals naturally, without the awkward asks or scripts. Whether you’re building your first referral system or improving an existing one, this conversation gives you real tools to strengthen relationships and scale sustainably.

Tune in, take notes, and let’s build a law firm that grows because your clients want to tell everyone about you.

📰 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://www.amazon.com/dp/B0FTSM619L

🌺 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

🌐 Visit my website:
https://www.jordanostroff.com

Show more...
2 months ago
51 minutes 41 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP52: Sharing Your Authentic Self featuring Hunter Garnett

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 you’ve ever wondered what it looks like to lead with purpose and live with balance, this conversation will hit home. Tune in, take notes, and then take action.

🔗 Links & Resources:
👉 https://linktr.ee/LawyerWithALife
📚 Love Your Law Firm Book: https://www.amazon.com/Love-Your-Law-Firm-Roadmap-ebook/dp/B0CWQSLCF7
🌺 The Luau: https://app.lawmatics.com/forms/share/782ca378-c8ab-42d9-8b05-19c62f932f15
📰 Newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08
🧭 CARPE Hiring Playbook: https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27
🎧 Podcast on Spotify: https://open.spotify.com/show/7L8yJ0rRL66Nrjfe5uX418?si=ueFfkQRyQYanAUmrBnHEqw
▶️ Podcast on YouTube: https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe&si=aHk7wPFIeyasU4HU

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2 months ago
51 minutes 5 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP51: Daily Habits That Actually Move the Needle feat. Neal Goldstein

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 episode is your wake-up call. Tune in, take notes, and start building habits that create real results — not just checkboxes.

🔥 Watch & Listen here:
🎧 Spotify: https://open.spotify.com/show/7L8yJ0rRL66Nrjfe5uX418?si=ueFfkQRyQYanAUmrBnHEqw
📺 YouTube Playlist: https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe&si=aHk7wPFIeyasU4HU

🚀 Build your own life-first business with Jordan:
🌺 Join The Luau: https://app.lawmatics.com/forms/share/782ca378-c8ab-42d9-8b05-19c62f932f15
🧠 Grab the Hiring SOP: https://linktr.ee/LawyerWithALife
📩 Subscribe to the Lawyer With A Life Newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08
📘 Get Jordan’s book Love Your Law Firm: https://www.amazon.com/dp/B0CWQSLCF7

✨ Because the goal isn’t just to have a successful firm — it’s to have a life you love too.

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2 months ago
54 minutes 44 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP50: Time Audit feat. Jordan Ostroff

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 the hidden time sucks killing your productivity
✅ Reclaim control of your calendar so you can work less and live more

Whether you’re a lawyer, business owner, or entrepreneur, this episode will help you stop reacting and start intentionally designing your day. Jordan shares the same framework he uses with his coaching clients to build systems that support freedom, not burnout. 🌴

If you’ve ever said, “I just need more time,” this episode is your wake-up call.

🎧 Listen on Spotify:
https://open.spotify.com/show/7L8yJ0rRL66Nrjfe5uX418?si=ueFfkQRyQYanAUmrBnHEqw

▶️ Watch the full episode on YouTube:
https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe&si=aHk7wPFIeyasU4HU

📘 Get the CARPE Hiring SOP – Build your dream team faster:
https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27

🌺 Join The Luau – Our life-first lawyer community:
https://app.lawmatics.com/forms/share/782ca378-c8ab-42d9-8b05-19c62f932f15

📬 Subscribe to the Newsletter – Weekly mindset, systems, and strategy tips:
https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08

🌐 Visit My Website:
https://www.jordanostroff.com

🌴 Explore More Resources:
https://linktr.ee/LawyerWithALife

Show more...
2 months ago
20 minutes 30 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP49: Culture and Hiring for a Great Business and a Better Life feat. Erin Andersen

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 business owner needs to hear. Whether you’re leading a law firm, scaling a small business, or just trying to create more balance between work and life, this conversation will show you how the right culture and hiring practices can transform not only your business but also your everyday life.

If you’ve ever wondered how to:
✅ Attract the right talent for long-term success
✅ Build a business culture that keeps your team motivated
✅ Create systems that give you more time for the life you want

…then this episode is for you.

📌 Subscribe to my newsletter and get weekly strategies to build a business that gives you your life back:
https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08

🌺 Join The Luau, our community for lawyers who want accountability, real connections, and a life-first business:
https://app.lawmatics.com/forms/share/782ca378-c8ab-42d9-8b05-19c62f932f15

🛠️ Get the Carpe Hiring SOP, your playbook for hiring smarter:
https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27


▶️ Watch episodes on YouTube:
https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe&si=aHk7wPFIeyasU4HU


🌐 Explore all my resources:
https://linktr.ee/LawyerWithALife


Show more...
3 months ago
51 minutes 55 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP48: The Lifestyle Revolution feat. Lauran Cowan

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 are tired of burnout and ready to build businesses that serve their lives, not the other way around. From daily routines to long-term vision, Laura lays out how to escape the overwork cycle and finally step into alignment with the life you want to live.

If you’ve ever wondered how to balance ambition with actually enjoying the journey, this conversation is for you.

📌 Subscribe to my newsletter for weekly insights: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08

🌺 Join The Luau community and start building a life-first business: https://app.lawmatics.com/forms/share/782ca378-c8ab-42d9-8b05-19c62f932f15

🛠️ Get my Hiring SOP to scale smarter: https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27

🎙️ Listen on Spotify: https://open.spotify.com/show/7L8yJ0rRL66Nrjfe5uX418?si=ueFfkQRyQYanAUmrBnHEqw

▶️ Watch the full playlist on YouTube: https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe&si=aHk7wPFIeyasU4HU

📖 Grab my book Love Your Law Firm: https://www.amazon.com/Love-Your-Law-Firm-Roadmap-ebook/dp/B0CWQSLCF7

🌐 Explore everything in one place: https://linktr.ee/LawyerWithALife

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3 months ago
47 minutes 25 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP47: The AMA Episode: Fatherhood, Risk & Running a Business feat. Jordan Ostroff

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 burning out, this one’s for you. Grab a seat, kick back, and let’s get real about what it means to be a Lawyer With A Life.

👥 Join The Luau community: https://app.lawmatics.com/forms/share/782ca378-c8ab-42d9-8b05-19c62f932f15
📄 Get the Hiring SOP here: https://app.lawmatics.com/forms/share/34602ac9-af52-4529-a848-fef07760b074
📬 Subscribe to my newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08
🌴 Explore everything in one place: https://linktr.ee/LawyerWithALife
📖 Grab my book Love Your Law Firm: https://www.amazon.com/Love-Your-Law-Firm-Roadmap-ebook/dp/B0CWQSLCF7
🌐 Visit my website: https://www.jordanostroff.com


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3 months ago
1 hour 2 minutes 19 seconds

The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
EP46 The Leid Back Life: Marketing for Happiness feat. Joshua Baron

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, building authentic connections, and why marketing rooted in happiness creates better outcomes for your team and your clients.


  • 🌴 All My Links & Resources: https://linktr.ee/LawyerWithALife

  • 🌺 Join The Luau (Life-First Lawyer Community): https://app.lawmatics.com/forms/share/782ca378-c8ab-42d9-8b05-19c62f932f15

  • 📋 The Carpe Hiring SOP (Your Blueprint to Hiring Right):

    https://app.lawmatics.com/forms/share/574169e4-3db9-478e-86e0-a6ab67df6e27

  • 🏝️ Visit My Website: https://www.jordanostroff.com

  • 📰 Subscribe to the Newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08

  • 📖 Love Your Law Firm (Amazon Best Seller): https://www.amazon.com/Love-Your-Law-Firm-Roadmap-ebook/dp/B0CWQSLCF7

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    3 months ago
    51 minutes 18 seconds

    The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
    The Leid Back Life: The Benefits of Being You feat. Bryan Haskins

    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. Tune in at 6 PM!

    📌 Learn more at: https://www.jordanostroff.com
    👉 More here: https://linktr.ee/LawyerWithALife
    ✉️ Subscribe to the weekly newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08
    ▶️ YouTube: https://youtube.com/playlist?list=PLrh5y6Kzkyb3qfxys1KV_cl8u7BGooZKe&si=aHk7wPFIeyasU4HU

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    3 months ago
    49 minutes 7 seconds

    The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
    The Leid Back Life: The "Present" of AI for Business and Life feat. Carolyn Elefant

    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, creativity, and client experience without losing the human touch. Whether you’re curious about leveraging AI in your own practice or just want to hear how it’s already changing the game, this conversation delivers clarity, strategy, and inspiration.

    🎧 Tune in on Spotify, Apple Podcasts, and YouTube to catch the full episode.

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    4 months ago
    50 minutes 42 seconds

    The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
    The Leid Back Life: Becoming a Resilient Business Owner

    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 conversation is for you.

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    4 months ago
    42 minutes 42 seconds

    The LEI'D Back Life: Loving Entrepreneurship and Improving Daily
    The Leid Back Life: Being a CEO

    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 stepping into the CEO role, you’ll leave with practical, no-fluff takeaways you can apply today.


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    4 months ago
    48 minutes 27 seconds

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