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

Lawyer with a Life - Jordan Ostroff
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  • Entrepreneurship
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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. Getting Your Story Out There feat. Jonathan White

    5d ago

    Getting Your Story Out There feat. Jonathan White

    💥 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 wanted while living an even better life. Learn more about Atticus: https://atticusadvantage.com. Welcome to Episode 84 of The Laid Back Life Podcast! In this raw and deeply impactful episode, Jordan sits down with attorney, founder, and keynote speaker Jonathan White. From the outside, elite entrepreneurs and C-suite executives look entirely successful, armored up, and unstoppable. But inside, many are running on empty—hollowed out by a constant need to achieve, without ever understanding why. Jonathan pulls back the curtain on his own intense journey. He shares how growing up in a home shaped by addiction forced him to build adolescent survival tools that later mutated into adult torment. From facing a marriage breaking point to surviving a literal near-death experience—collapsing with a 106-degree heat stroke during a road race—Jonathan outlines how he stopped running from his past and transformed it into absolute presence. If you are a high-performing firm owner struggling to turn off your phone, be present at your kids' games, or step away for a true vacation, this episode is your wake-up call. (00:00) - Special Announcement: Jordan Joins Atticus (00:45) - Welcome Episode 84: Guest Jonathan White (03:04) - Why Add Public Speaking to a Busy Law Practice? (06:31) - Fear vs. Want: Does Everyone Have a Story to Tell? (10:04) - Stepping Into Keynote Speaking & Professional Training (13:07) - True Vulnerability vs. Attention-Seeking on Social Media (19:26) - Stress-Testing Your Team & Systems to Take a Real Vacation (24:43) - Shifting Perspectives: Learning to Tell Your Story From Her Eyes (33:46) - The "Stop Running" Framework Explained (37:54) - Surviving a Heat Stroke: The 106-Degree Collapse (41:00) - Presence Over Panic: A Full-Circle Challenge in 2024 (45:33) - The 4 Foundations: Show Up, Tell the Truth, Let Go, & Be Vulnerable (48:50) - One Actionable Truth You Need to Share Safely Today 🌐 Connect with Jonathan: Speaker Website: https://jonathanwhitespeaks.com Law Firm Website: https://jordanwhitellc.com 📅 Ready to design a law firm that runs smoothly without you? Book a consultation with Jordan: https://jordanostroff.com/book-an-appointment/ 📰 Subscribe to our weekly newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08

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

    May 27

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

    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 transitioned from managing legacy legal automations to building custom-coded case management systems and agentic workflows. Originally recorded as a live interactive webinar, this session breaks down the definitive legal frameworks of Claude Chat, Claude CoWork, and Claude Code to fully automate website compliance, technical SEO schema, and real-time intake data dashboarding. ⏱️ Episode Timestamps (00:00) - Beyond Brains: The AI "Harness" Explained (02:02) - Gemini Integration in Google Workspace (03:39) - Scaling with Workspace Intelligence Agents (05:13) - Consistency Over Platform Hopping (05:46) - Complex Research Capabilities: ChatGPT vs. Claude (08:18) - Cross-Platform Synthesis for Knowledge Work (09:38) - Automating Like Tony Stark to Work Less (11:19) - Deploying Local Models and Desktop Agents Safely (15:48) - Running Enterprise-Grade Models on a Laptop (23:40) - Automating ADA Compliance for Law Firm Websites (25:25) - Hacking Technical SEO with Schema Markup (30:26) - Syncing Google Analytics and Meta Ads to Claude Code (34:19) - Flywheel Loops and Recursive Performance Tracking (36:00) - Persistent Intake and Financial Dashboards (43:34) - Chat, CoWork, and Code: The 3 Frameworks of Claude 🌐 Visit Dan's website: https://schnurbuschlaw.com/ 💼 Connect with Dan on LinkedIn: https://www.linkedin.com/in/dschnurbusch/ 📅 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

    54 min
  3. Networking Your Way to a Great Life

    May 20

    Networking Your Way to a Great Life

    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 purely from referrals. Today, she helps lawyers build genuine friendships that turn into consistent revenue. Jordan and Delisi break down the ultimate blueprint for authentic relationship building, why passing a bad referral is a dangerous reflection of your reputation, and how to unlock a hidden goldmine of cases using your existing phone contacts. (00:00) - Intro & Who is Delisi Friday? (01:35) - Why Lawyers are Terrified of Rejection (03:00) - The Stuffy "Networking Persona" vs. Real Dating (05:25) - Why Referrals Are a Direct Reflection of You (06:57) - The 5% Fee Debate: 75% of a Grape vs. 33% of a Watermelon (09:38) - Automating Like Tony Stark and Leading Like Captain America (14:21) - Offline Relationship Blueprints for Introverted Lawyers (18:59) - Reconnecting with the Ultimate Hidden Goldmine: Law School Friends (24:05) - Using Calendars and "Send Later" to Keep Connections Consistent (40:22) - The 5 Core Practice Areas Every Attorney Needs in Their Rolodex 🔗 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 🌺 Join The Luau Group:https://www.facebook.com/groups/theluau 🧭 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 🌐 Visit my website:https://www.jordanostroff.com

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

    May 13

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

    "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 specializes in helping legal professionals cut through the technology hype to adopt tools with clarity and confidence. In this conversation, we discuss using AI not just for productivity, but for intentionality. In a world where we spend too much time worrying about the "how, what, and where," Colin explains how AI can take over the noise, leaving you free to focus on the signals... the things that actually make you happy. From analyzing meeting transcripts for better client communication to breaking down a 300-item bucket list into actionable steps, this episode is about making the tool work for the person. Timestamps: (0:00) Introduction to Colin Levy (1:20) Are you too far behind the ball with AI? (4:02) Practical workday use cases for AI (5:31) Where to start... The power of simple experimentation (10:42) Will AI replace your job... Redefining tasks vs. roles (13:09) Using AI as an objective mirror for self-evaluation (16:20) Translating medical and legal jargon for better human questions (23:03) Removing administrative work and pointless tasks (27:09) Using AI to find more fun and happiness in life (41:51) Project 300... Organizing your life’s bucket list with AI ▶️ 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 📰 Subscribe to the Lawyer With A Life newsletter:https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 🌐 Visit my website:https://www.jordanostroff.com

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

    May 6

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

    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 fulfillment. Highlights include: ✅ The Loneliness Warning: Why the Surgeon General views isolation as a major health risk ✅ Flow States: How to identify what feels "light" versus "heavy" in your workday ✅ Intentional Calendaring: Why Jordan blocks out Topgolf and networking lunches weeks in advance ✅ Contagious Fun: Why you are the average of the five people you spend the most time with Timestamps: (0:00) Introduction: A Birthday Gift for the Community (1:35) The Science of Happiness: Harvard Research & Social Connection (3:32) Identifying your Flow State: What makes you lose track of time? (4:12) The 75% Rule for Productivity and mid-day resets (6:02) Strategy: Joining someone else's rhythm (The Canoeing Example) (10:35) If it isn't on the calendar, it doesn't exist (13:21) Scheduling "Day Dates" and family dinner boundaries (16:35) Shared Experience: Why solo joy is often rated lower than social joy (19:13) The Outreach Challenge: Reach out to these 3 people today (19:50) The 30-Minute Rule: Cutting out what you don't enjoy 🔗 Next Move: https://linktr.ee/LawyerWithALife 📂 Free Resources: https://jordanostroff.com/resources/ 📅 Consultation: https://jordanostroff.com/book-an-appointment/ 📰 Newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 📚 The Book: Love Your Law Firm - https://amzn.to/4a3ziB4 🌺 The Luau Community: https://www.facebook.com/groups/theluau 🌐 Website: https://www.jordanostroff.com Love life. Love entrepreneurship. Improve daily.

    21 min
  6. We is Stronger Than Me: Collaboration for a Great Life feat. Robert Hana

    Apr 29

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

    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 collaborators and why "playing it safe" in the old legal model is a recipe for irrelevance in the AI era. Robert shares his journey from London to global stages, explaining how to build "relationship capital" that pays dividends for decades. Timestamps: (0:00) Introduction to Robert Hanna (2:01) Defining Collaboration: Why "We" is Greater Than "Me" (5:26) The Secret to Authentic, Long-Term Partnerships (9:04) Out-of-the-Box Collabs: PR Agencies, Paddle, and AI Robots (13:35) Attracting Top Talent through Modern Branding .(18:16) How to Research and Pitch Your Dream Partners (23:54) COI: The Massive Cost of Staying in Your Own Lane (30:51) Overcoming the Procrastination Trap in Law (36:00) Turning Digital Handshakes into Real Friendships (47:44) Closing Thoughts & Contact Info 🎧 Listen to The Lei’d Back Life 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 📰 Subscribe to the Lawyer With A Life newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 🌐 Visit my website: https://www.jordanostroff.com

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

    Apr 22

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

    "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 to enjoying your time off and how to apply the Eisenhower Matrix to your daily decisions. Highlights include: ✅ The 2-Minute Rule: Stop delegating tasks that take less time to do yourself ✅ The Weekly Review: Jordan shares the 4 questions that ensure he spends enough time with himself, his son, his wife, and his friends ✅ Red vs. Blue Calendaring: How to separate the "immovable" client meetings from the flexible "creative" blocks ✅ The Eisenhower Matrix: A quick guide to deciding what to Do, Defer, Delegate, or Drop Timestamps: (0:00) Introduction to "Mind Like Water" (1:32) The 2-Minute Rule for quick wins (6:32) Breaking big projects into actionable tasks (9:31) Why 100% faith in your calendar is the key to vacation sanity (12:55) Identifying where you leak mental energy (Home, Health, Work, Relationships) (17:31) The "Red vs. Blue" calendar system for firm owners (22:06) The 4-Question Weekly Review for life balance (27:42) The "Wave Referral Plan" for better networking (37:17) Scientific focus: Why morning work is different from afternoon work (52:16) The Eisenhower Matrix: Do, Defer, Delegate, Drop Resources for Your Firm: 🔗 Next Move: https://linktr.ee/LawyerWithALife 📂 Free Resources: https://jordanostroff.com/resources/ 📅 Consultation: https://jordanostroff.com/book-an-appointment/ 📰 Newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 📚 The Book: Love Your Law Firm - https://amzn.to/4a3ziB4 🌺 The Luau Community: https://www.facebook.com/groups/forlawyersbylawyers 🌐 Website: https://www.jordanostroff.com Love life. Love entrepreneurship. Improve daily.

    55 min
  8. Focus 90 and the Future of Your Firm feat. Corine Rogers

    Apr 15

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

    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 to be in the room, the essential prep work required, and the three simple questions that will uncover hidden issues before they become disasters. If you want a firm that runs like a well-oiled machine so you can actually step back and enjoy a laid-back life, you cannot miss this episode! In this episode, we cover: (0:13) - Introduction to Corine Rogers and Simple Smart Solo (1:22) - The goal: Moving your firm from chaos to control (3:08) - Who is the Focus 90 meeting designed for? (4:18) - Who needs to attend (why leadership must buy-in) (6:02) - The best day and time to schedule this meeting (7:40) - The "Focus 90" name and the 90-minute time limit (8:20) - Mandatory pre-meeting prep (13:00) - How to create your master list of active matters (15:08) - The golden rule: No skipping files or hiding clients (17:40) - Why you should sort your matters from new to old (19:22) - The only 3 questions you need to ask per matter (23:33) - Why Focus 90 must become a weekly habit (27:30) - Dealing with overwhelmed staff and bottlenecks (32:13) - Triage: What the firm owner must do after the meeting (37:02) - The most common pitfalls (and why you can't have sidebar gossip) 🔗 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 to the Lawyer With A Life 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 community:https://www.facebook.com/groups/forlawyersbylawyers ▶️ 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 🌐 Visit my website:https://www.jordanostroff.com

    42 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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