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

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

48 min · 13 de may de 2026
Portada del episodio Using AI to Live the Life We Want: The Blueprint for a Truly Great Life feat. Colin Levy

Descripción

"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

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88 episodios

episode The AMA Episode: Fatherhood, Risk & Running a Business feat. Jordan Ostroff artwork

The AMA Episode: Fatherhood, Risk & Running a Business feat. Jordan Ostroff

💥 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 a highly anticipated, completely unfiltered Ask Me Anything (AMA) masterclass edition of The Laid-Back Life Podcast! In this special solo episode, host Jordan Ostroff takes questions submitted directly by listeners and Atticus members to dive straight into the heart of what modern law firm owners care about most.Jordan strips away the traditional, rigid corporate playbook to share personal stories, tactical frameworks, and pop-culture analogies that will challenge how you look at your calendar, your business connections, and your lifestyle design. From the exact moment he realized he had to step out of constant casework to his unbroken 10,000-daily-step streak, this episode serves as a comprehensive manual for building a profitable firm that wraps entirely around a joyful life. 🧠 Featured Insights ✅ The Hot Sauce Awakening: How a surprise pregnancy in 2017 forced Jordan to escape the 100-hour grind and shift into a CEO mindset. ✅ The Definition of Enough: Why chasing an arbitrary "million-dollar firm" is a trap... and how to scale for true time freedom. ✅ Top Golf Networking: Why traditional bar events fail, and how casual settings naturally build high-value referral partnerships. ✅ Leading vs. Lagging Indicators: Lessons from an unbroken daily step streak applied directly to tracking firm growth metrics. ✅ Business Justice League: Building a corporate dream team by blending radical kindness with historical strategy. ⏱️ Episode Timestamps 00:00 - Announcement: Jordan Joins Atticus 01:48 - Fatherhood Lessons Applied to Business 04:45 - Balancing Risk Tolerance Scale 07:52 - Cannon Funerals & Facing Mortality 12:10 - "Lawyer with a Life" Defined 16:04 - The Spider-Man Marketing Framework 19:01 - Grounded Horror & Reality-Based Storytelling 22:25 - Building a Corporate Justice League 26:16 - Back to the Future vs. Star Wars 27:52 - Shifting From Lawyer to CEO 34:00 - Defining Success & "Enough" 38:18 - Filtering Out Bad Business Connections 41:54 - Surprising Referral Partners 44:39 - 4 Red Flags in Lawyer Networking 51:32 - Macros, Screen Time & Morning Habits 53:26 - 75 Hard & Expanding Personal Capacity 55:42 - Identity & Keeping a 10k-Step Habit 58:52 - 1 Simple Change to Escape Burnout 🦅 Learn more about Atticus: https://atticusadvantage.com 📅 Book a growth consultation with Jordan Ostroff: https://jordanostroff.com/book-an-appointment/ 📰 Subscribe to our weekly newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08

30 de jun de 20261 h 0 min
episode Billing Tips For a Great Firm and An Even Better Life feat. Jyl Warwick and Karyn Campbell artwork

Billing Tips For a Great Firm and An Even Better Life feat. Jyl Warwick and Karyn Campbell

💥 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 [https://atticusadvantage.com] Are you accidentally throwing away 20% of your hard-earned revenue every single week just because you delay entering your billable hours? Discover how to plug your firm's hidden financial leaks, optimize automated collections to 92%, and transform systemic daily chaos into repeatable, predictable profitability. In this episode of The Laid-Back Life Podcast, Jordan Ostroff is joined by Jyl Warwick and Karyn Campbell. Jyl and Karyn are the co-founders of Jurisend, a premier operations, billing, and legal bookkeeping firm that helps solo and small practices build elite operational infrastructure. Having scaled a woman-owned firm from a handful of attorneys to over 20 mid-pandemic before a successful national merger, they bring deep expertise in translating healthcare-level efficiency into the legal arena. Jordan Ostroff, Jyl, and Karyn break down the shocking metadata behind contemporaneous billing leaks, the exact methodology for building law firm standard operating procedures via staff roundtables, and how to spot a crumbling administrative process before it compromises your monthly cash flow. ⏱️ EPISODE TIMESTAMPS 00:00 - Special Announcement: Jordan Ostroff Joins Atticus 00:50 - Welcome to the Show: Introducing Jyl Warwick and Karyn Campbell 02:20 - Shifting From Healthcare Operations to Legal Systems 04:37 - The Massive Operational Differences Between Medical and Legal 06:20 - Reimagining Law Firm Invoicing with Guaranteed Payments on File 07:06 - Demystifying ACH: Driving Collection Rates Up to 92% 08:15 - Implementing Paralegal Roundtables to Crowdsource Operational SOPs 10:41 - Navigating Chaos: Operational Sweet Spots From 1 to 20 Attorneys 12:44 - Diagnosing the Root Cause: Starting with Your Core Operational Pain Points 14:39 - EMR vs. CRM: Why Lawyers Shouldn't Be Afraid of Breaking Software 16:42 - Spotting System Breakdowns via Cash Flow Fluctuations and Late-Night Emails 18:11 - The Shocking Cost of Delaying Time Entries: The 20% Revenue Leak 21:04 - Shifting Non-Billable Overhead Tasks From Paralegals to Admin Desks 35:25 - Overcoming the Flat Fee Trap: Displaying Value in Project-Based Invoices 37:03 - Reclaiming Stolen Profits From Legal Bookkeeping and Case Expense Blindspots 🌐 Visit the Jurisend website to streamline your firm's back office: https://www.juriscend.com [https://www.juriscend.com] 🦅 Learn more about Atticus: https://atticusadvantage.com [https://atticusadvantage.com] 📅 Book a growth consultation with Jordan Ostroff: https://jordanostroff.com/book-an-appointment/ [https://jordanostroff.com/book-an-appointment/] 📰 Subscribe to our weekly newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 [https://www.google.com/search?q=https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08]

23 de jun de 202648 min
episode Designing Your Firm Around Your Life feat. Cristina Hughes artwork

Designing Your Firm Around Your Life feat. Cristina Hughes

💥 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 Are you trapped in the day-to-day logistics of your law firm, dreaming of a practice that scales without consuming your entire personal life? Discover how to ruthlessly prioritize your goals, empower your team to solve problems independently, and shift your mindset from a solo technician to a true CEO .In this episode of The Laid-Back Life Podcast, Jordan is joined by Cristina "Tina" Hughes. Cristina is an immigration attorney, founder of a seven-figure law firm, and an executive coach who intentionally structured her multi-million dollar practice to support a lifestyle centered around family, competitive cycling, and freedom of travel. Jordan and Tina dive deep into the elite athletic mindset applied to business growth, the incredible results of tripling consultation fees to attract ideal clients, and why stepping away from a firm for weeks at a time forces your internal systems to mature... and thrive. ⏱️ Episode Timestamps 00:00 - Special Announcement: Jordan Joins Atticus 01:04 - Redefining the Seven-Figure "Lifestyle Business" 01:45 - The Road Cyclist Metaphor: Balancing Elite Sport and Firm Stress 03:37 - How Pregnancy and Motherhood Accelerate True Efficiency 06:23 - Overcoming Resistance to Executive Accountability and Business Coaching 07:35 - What Reaching Category 1 Tells Us About Continuous 1% Growth 09:52 - Identifying the Blind Spots in Employee Communication 11:15 - The Financial Quote: Driving Authority and Client Respect Through Pricing 13:58 - Tripling Consultation Fees to Eradicate Time-Wasting Tire Kickers 15:52 - Demystifying the Illusion of the Seven-Figure Revenue Milestone 18:30 - Implementing Micro-Visioning and Building Multi-Week Travel Blueprints 20:23 - Giving Employees the Boundaries and Resources to Solve Problems Alone 22:12 - Flat Fee Conundrums and Time Tracking in Modern Immigration Firms 23:50 - The Covey Framework: Sorting Urgent Pebbles From High-Value Rocks 33:05 - Time Auditing the CEO: Defeating the Tech-Stack Frankenstein 45:36 - Final Takeaway: Unlocking Creative Freedom with a 15-Minute Walk 🌐 Visit Cristina's website: https://cristinahughes.com 📱 Connect with Cristina on LinkedIn: https://www.linkedin.com/in/cristinahughes/ 🦅 Learn more about Atticus: https://atticusadvantage.com 📅 Book a growth 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

16 de jun de 202647 min
episode The Most Important Piece of Advice You’ll Hear This Mid Year artwork

The Most Important Piece of Advice You’ll Hear This Mid Year

💥 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 [https://atticusadvantage.com/] Welcome to a special "Best Of" masterclass edition of The Laid Back Life Podcast! As host Jordan Ostroff continues his transition into his role as a practice advisor with Atticus, the show is evolving to bring you a sharper focus on moving out of the daily grind of lawyering and stepping into your true role as a law firm owner. To celebrate this exciting shift, we’ve curated the absolute finest life, mindset, and business frameworks shared on the podcast during the first half of 2026. Five world-class experts lay down the ultimate roadmap to help you redefine success, protect your time, and scale your firm authentically. 🧠 FEATURED INSIGHTS & GUEST LINKS Charley Mann breaks down the powerful Beckard Harris change equation ($D \times V \times F > R$) and explains why true, lasting habit changes require a radical shift in your personal identity. 🌐 Visit Charley: https://www.instagram.com/charleymann/ [https://www.instagram.com/charleymann/] Daniel Pink explores the tactical principle of "surrogation" and reveals how finding true purpose means consciously choosing the specific daily "torture" you are willing to endure for ultimate success. 🌐 Visit Dan: https://danpink.com [https://danpink.com/] Allison Williams dives deep into overcoming the ego-driven "hero complex" that traps owners, sharing a repeatable process for systematically firing yourself from low-level tasks. 🌐 Visit Allison: https://lawfirmmentor.net [https://lawfirmmentor.net/] Robert Hanna explains why "we is greater than me" and demonstrates how to unlock exponential growth for your firm through highly strategic, authentic audience-sharing collaborations. 🌐 Visit Robert: https://legallyspeakingpodcast.com [https://legallyspeakingpodcast.com/] Gordon Firemark challenges you to throw out everyone else's scorecards, redefine what real success looks like for your family, avoid deathbed regrets, and prioritize daily fun. 🌐 Visit Gordon: https://gordonfiremark.com [https://gordonfiremark.com/] ⏱️ EPISODE TIMESTAMPS 00:00 - Special Announcement: Jordan Joins Atticus 01:26 - Charley Mann: Shifting Identity & The Change Equation 08:50 - Daniel Pink: Finding Purpose, Surrogation, & Choosing Your Torture 13:51 - Allison Williams: Overcoming the Ego Hero Complex & Firing Yourself 19:51 - Robert Hannah: Strategic Collaborations & Why We > Me 25:48 - Gordon Firemark: Redefining Success, The Scorecard, & Prioritizing Fun 31:24 - Outro: Finding Your Core Takeaway & Taking Immediate Action 🦅 Learn more about Atticus: https://atticusadvantage.com [https://atticusadvantage.com/] 📅 Book a growth consultation with Jordan: https://jordanostroff.com/book-an-appointment/ [https://jordanostroff.com/book-an-appointment/] 📰 Subscribe to our weekly newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 [https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08]

9 de jun de 202632 min
episode Getting Your Story Out There feat. Jonathan White artwork

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 [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 [https://jonathanwhitespeaks.com] * Law Firm Website: https://jordanwhitellc.com [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/ [https://jordanostroff.com/book-an-appointment/] 📰 Subscribe to our weekly newsletter: https://app.lawmatics.com/forms/share/0680eb74-2022-45fe-946f-000adf894a08 [https://www.google.com/search?q=https%3A%2F%2Fapp.lawmatics.com%2Fforms%2Fshare%2F0680eb74-2022-45fe-946f-000adf894a08]

3 de jun de 202656 min