Connecting the Dots with Jessica Caresse

Jessica Caresse
  • 5.0 (14)
  • Entrepreneurship
  • Weekly

Conversations with leaders who love their work, and found a way to carry it without losing themselves. I spent years as the one holding everything together at work, and I know what it costs. Here, executives, founders and operators talk honestly about the moment success stopped feeling like success, and what they changed: in the process, the team, the tools, and in themselves. Every episode connects one problem at work to the one inside. You leave with one thing to change at work, and one thing to change in yourself. Where are you right now? Take the free Level of Consciousness Assessment: jcaresse.com/podcast Quielimens, my daily practice for leaders, is coming soon. Join the waitlist: jcaresse.com/wellness Jessica Caresse is Managing Director of J.Caresse & Company, an operations and AI transformation firm. jcaresse.com

  1. 1d ago

    He Did Everything Himself Until His Body Said Stop | Peter McLaughlin

    He did everything himself until his body said stop. Why the people who hold it all together burn out first. Peter McLaughlin, root-cause hypnotherapist and founder of Blue Sky Hypnosis, on stress, identity and change. He spent years on Wall Street, ran a business, raised three kids and took on a 100-year-old house. His job, he believed, was to suck it up and keep moving. Then a diagnosis stopped him cold. In this conversation Peter explains why the body sends warning lights long before it breaks down, why change can feel unsafe even when you want it, and why willpower loses to identity. Then he walks me through a live identity exercise, and tells the story of a client whose father apologized for the first time in his life, hours after a session. If you are the one who holds everything together, this one is for you. Chapters 00:00 Cold open: the apology 00:36 Show intro 00:43 Meet Peter McLaughlin 02:02 The diagnosis that got his attention 03:22 Wall Street, a business, three kids, a 100-year-old house 06:15 "My job was to suck it up" 08:57 Where "I'll just handle it" starts 10:43 Jessica's story: holding everyone together 13:24 The warning signs he ignored 15:16 Your body has warning lights 16:08 What chronic stress does to the body 19:33 Why change feels unsafe 23:38 Identity runs deeper than willpower 28:06 A live identity exercise 33:22 Acting, anger, and permission to change 36:58 You can change, at any age 39:16 Where you hold tension 41:16 Safe or not safe: your nervous system 43:44 Fix the root cause, not the symptom 45:57 Pull up the anchor, raise the sails 48:08 The client whose father apologized 51:13 Emotional handcuffs and forgiveness 56:03 What he would tell his five-year-old self 58:12 Where to find Peter Connect with the guest Blue Sky Hypnosis: blueskyhypnosis.com Where are you right now? Take the free Level of Consciousness Assessment: jcaresse.com/podcast Watch this conversation on YouTube: youtube.com/watch?v=YPz68xPeS_Q Connect with Jessica: jcaresse.com This conversation shares personal experience and perspective. It is not medical advice. Talk with a qualified professional about your health.

    He Did Everything Himself Until His Body Said Stop | Peter McLaughlin

  2. Aug 14

    She Was Fired While Bedridden, Then Built an Empire on Her Own Terms

    Fired while bedridden for 9 months. What burnout and corporate culture taught her about intuition. Dr. Suzzanna Ravenlight, organizational psychologist and executive leadership coach, on staying yourself. I sit down with Dr. Suzzanna Ravenlight, organizational psychologist and founder of Ravenlight Leadership Coaching, for a candid talk about intuition, burnout and corporate culture. You will learn the coin-flip exercise she teaches clients to tell fear from real intuition, why return-to-office mandates and micromanagement backfire on the leaders enforcing them, and how her own health battles shaped the way she coaches. Chapters 00:00 Intro 00:41 Welcome to Connecting the Dots 01:38 Meet Dr. Suzzanna Ravenlight 02:19 Blending Psychology, Business & Spirituality 05:36 Intuition vs. Fear: Why Kids Trust Instinct and Adults Lose It 07:52 The 90-Second Emotion Rule 08:26 The Coin-Flip Decision Exercise 09:31 Catching Yourself Giving Meaning to Things 11:52 Getting Shingles at 31: The Body Keeping Score 14:33 The Passion Behind Her Leadership Work 15:45 Bedridden for 9 Months, and Still Laid Off 16:40 The Performative Culture of Corporate America 18:18 Why Micromanagement and RTO Mandates Don't Work 20:33 Middle Management: Burnout by Design 23:12 "What Do You Do?" and Defining Yourself Beyond Your Title 26:33 Cognitive Dissonance and Undoing Conditioning 31:16 A Young Family and Moving 27 Times 35:21 Health Battles: Lumpectomy, Six Miscarriages, Autoimmune Disease 37:43 Sitting with Grief and the Loneliness of Doing the Work 39:42 Reframe: Who Deserves to Get to Know More of You? 44:14 Top Life Lessons: Stop Taking Yourself So Seriously 45:15 Never Stop Learning + Challenge Your Own Perspective 49:00 Where to Find Dr. Susanna Ravenlight 51:57 Outro Where are you right now? Take the free Level of Consciousness Assessment: jcaresse.com/podcast Watch this conversation on YouTube: youtube.com/watch?v=Xm3kf76PTMI Connect with Jessica: jcaresse.com This conversation shares personal experience and perspective. It is not medical advice. Talk with a qualified professional about your health.

    She Was Fired While Bedridden, Then Built an Empire on Her Own Terms

  3. Jul 3

    The Cupcake War That Made Her Quit Baking Forever (True Corporate Story)

    A CEO told her to choose between her job and her kids. What corporate burnout really costs women. Lori Lalonde, former senior tech leader turned executive coach, on boundaries, power, and office politics. I sit down with Lori Lalonde, CEO of Her Executive Ascent and a corporate tech leader since 1997, about the moments that pushed her out of corporate life. You will hear the town hall confrontation, the cupcake incident, and the practical boundaries that changed how she leads, plus why office politics is a skill worth learning. Chapters 0:00 Intro 0:42 Welcome & Meet Lori Leland 1:57 "Ruining the Workplace Since 1997" 3:11 Sent to the "Doghouse" for Talking Too Much 5:44 Growing Up With Different Rules for Girls 11:23 The CEO Who Made Her Choose: Work or Family 19:55 The Top 3 Lessons From Getting Let Go 21:38 The Plan B Rule: Always Be Job Hunting 25:58 Becoming the Coach No One Else Would Be 30:05 How Companies Really Treat Women in Leadership 37:18 Why Return-to-Office Mandates Are Backfiring 38:57 The 7 Rules of Power: Interrupting, Availability & Being "the Bitch" 44:24 The Cupcake Wars 48:16 Building a No-Fluff Leadership Course for Busy Women 52:33 Leaping From Corporate Into Entrepreneurship 55:33 Her #1 Piece of Advice for Women Ready to Level Up 57:24 Where to Find Lori Connect with the guest Her Executive Ascent: herexecutiveascent.com Lori on LinkedIn: linkedin.com/in/lorilalonde Leadership Recalibrated podcast: podcasts.apple.com/us/podcast/leadership-recalibrated/id1869939398 Where are you right now? Take the free Level of Consciousness Assessment: jcaresse.com/podcast Watch this conversation on YouTube: youtube.com/watch?v=rl4o89-2T7U Connect with Jessica: jcaresse.com

    The Cupcake War That Made Her Quit Baking Forever (True Corporate Story)

  4. May 1

    The AI Platform Built From a Rooftop Conversation in Miami: The Indrasy Story

    Most AI tools ignore small businesses. Three founders built an AI platform just for them. I sit down with Indrasy's leadership team: CEO Kyle, CTO Rose and CRO Athena. I sit down with the full leadership team of Indrasy, three first-generation Americans building an AI operating system for small businesses. You will hear how a rooftop conversation in Miami became a company, how their platform differs from ChatGPT and Claude, and the real reason small businesses fail. Chapters 00:00 Opening 01:09 Welcome & Introducing the Indrasy Team 02:11 Kyle's Origin Story: Coding Since Childhood 03:31 How Kyle Met Rose and Athena 06:11 The "Magic Ingredients" of a Founding Team 07:17 Kyle's First Startup: Lessons From Carmen's Medicinals 08:30 Building Indrasy Full-Time Since October 09:07 What the Indrasy Platform Does 10:23 Use Case: Lead Research, Broadcasting & Marketplace 11:46 Agenda, Relationships & Comms: The Three Core Tools 13:13 How AI Pricing Works (The Starbucks Analogy) 14:25 The June 6th Event: What to Expect 16:53 Why Small Businesses Need Face-to-Face Trust 17:50 "An Opportunity for Giving, Not Getting" 18:52 The Four Pillars: Workshops, Pods, Expo & Main Stage 22:20 The Origin of the Event Concept: Community First 23:01 Being First-Gen Americans & Why Community Matters 25:34 The South Florida Networking Problem 28:37 "If You Go Alone You Go Fast, Together You Go Far" 31:38 Small Businesses Are Dying, And Here's Why 33:16 Small Businesses Are Living Paycheck to Paycheck 34:15 How Indrasy Is Different From Claude & OpenAI 36:38 Why Small Business Beats Enterprise Long-Term 38:42 The Awareness Problem: Big Tech Doesn't Market to Small Business 41:38 "I Want Our Platform to Be a Lifeline" 42:24 The Algorithm That Tells You Where to Start 44:22 Kyle's Focus Struggles & How He Built the Daily Algorithm 46:34 Why Project Management Frameworks Fail Small Business 47:12 Removing Corporate Language From the Platform 49:25 Internal Results: 10x-20x Efficiency Gains 51:17 AI Cybersecurity Warning: Be Careful With Open Source Agents 53:24 The AI Arms Race & Day-Zero Vulnerabilities 56:49 The FBI Director Hack & AI Impersonation Risk 01:02:24 The Problem With Metric-Obsessed Business Culture 01:05:17 Why Kyle Studied Psychology Instead of Tech 01:08:13 "You Always Need a System" 01:11:03 Will Everyone Be a 1099 in 10 Years? 01:12:51 The Psychology of Going From Employee to Business Owner 01:13:01 NPCs, Agency & Sheep Mentality 01:14:13 Jessica's Origin Story: Rich Dad Poor Dad at Age 13 01:18:52 "Stop Blaming. Go Out and Fix It." (Full Context) 01:19:39 Closing Advice: Read History, Know Your Why, Build an Advisor Board 01:25:03 "Your Mentor Is Your First Customer" 01:26:35 Where to Find Indrasy Connect with the guest Indrasy website: indrasy.com Where are you right now? Take the free Level of Consciousness Assessment: jcaresse.com/podcast Watch this conversation on YouTube: youtube.com/watch?v=-zVsYw7Y-AI Connect with Jessica: jcaresse.com

    The AI Platform Built From a Rooftop Conversation in Miami: The Indrasy Story

  5. Feb 20

    How I Quit the Police Force to Build a 6-Figure Assisted Living Business | Carline Cadet-Francois

    Leaving law enforcement to build a 6-figure assisted living business, step by step I sit down with Carline Cadet-Francois, founder of Florida Assisted Living Consulting (FALC). Carline Cadet-Francois, founder of Florida Assisted Living Consulting, walks through how she left the Sheriff's Office and built a 6-figure assisted living facility. You will hear how to start a senior care business in Florida, what her first year really looked like, why a mentor sped up her growth, and how she moved from an employee mindset to an owner's mindset. Chapters 0:00 Overcoming fear and taking action despite being nervous 0:59 Introduction: Meet Carline Cadet-Francois and FALC 2:36 Juggling entrepreneurship and being a mom of three 4:34 The breaking point: Leaving a newborn during a hurricane 9:23 The danger of stalling and being your own business bottleneck 12:55 Sheriff's Office mindset vs. Entrepreneur mindset 14:00 Why investing half your salary into a business mentor is worth it 17:44 Hitting 6 figures in your first year of business 20:57 Why start an Assisted Living Facility (ALF)? 29:44 The $2,500 course story: Why you must drop perfectionism 33:28 How to break the generational cycle of a poverty mindset 43:41 Final advice: Shifting your money mindset and finding community Connect with the guest Carline on LinkedIn: linkedin.com/in/carline-cadet-francois-1128b6323 FALC website: floridaassistedlivingconsulting.com Assisted Living and Caregivers Conference: floridaassistedlivingconsulting.com/assisted-living-and-caregivers-conference FALC on Instagram: instagram.com/floridaalfconsulting Caregivers Conference on Instagram: instagram.com/alfcaregivercon FALC on Facebook: facebook.com/share/19PK5WErKY/?mibextid=wwXIfr FALC on TikTok: tiktok.com/@floridaalfconsulting FALC on YouTube: youtube.com/@UCoVmTzl3xjEyBqdgU_FuVhQ Where are you right now? Take the free Level of Consciousness Assessment: jcaresse.com/podcast Watch this conversation on YouTube: youtube.com/watch?v=hUYs_wZigSQ Connect with Jessica: jcaresse.com

    How I Quit the Police Force to Build a 6-Figure Assisted Living Business | Carline Cadet-Francois

  6. Feb 13

    Stop Firefighting: How to Scale Your Startup Without Breaking It

    Scaling your startup feels like constant firefighting? Build the people infrastructure first. Gaby Enriquez, founder of HRbp Inc. and global People Operations leader, on growth that holds. I talk with Gaby Enriquez, founder of HRbp Inc. and a People Operations leader with 20+ years of experience, about the people and compliance foundation a growing company needs. You will hear how she bridges Finance, Sales and HR, what to watch when navigating M&A or expanding into LATAM and APAC, and how to scale without losing integrity. Chapters 0:00 Introduction 2:13 Meet Gaby Enriquez: The "Not-So-HR" Expert 05:20 The Gap: Why Finance, Sales, and HR don't align 12:45 Moving from Firefighting to Global Expansion 20:15 International Growth: Navigating LATAM and APAC Markets 32:10 Mergers & Acquisitions: Merging Different Company Cultures 45:00 The Blueprint for Turnkey Growth & Sustainable Profit 55:30 How to make your business more "Human" Where are you right now? Take the free Level of Consciousness Assessment: jcaresse.com/podcast Watch this conversation on YouTube: youtube.com/watch?v=7NVdvxfJxY8 Connect with Jessica: jcaresse.com

    Stop Firefighting: How to Scale Your Startup Without Breaking It

  7. 11/16/2025

    Escaping the Tech Trap: How Melissa O’Connor Rebuilt Her Firm from the Ground Up

    Paying thousands for legal software that delivers nothing? How one attorney walked away from it. Melissa O'Connor, founder of O'Connor Elder Law, rebuilt her firm on the Microsoft 365 tools she already owned. I sit down with Melissa O'Connor, founding attorney of O'Connor Elder Law, about why she paid an early termination fee to leave her case management software. She explains how she built her firm's systems on Microsoft 365, what she learned dealing with vendor support, and how she is getting her firm ready for AI by scanning her physical library. Chapters 00:00 The "Early Termination Fee" 03:15 From Environmental Scientist to Elder Law Attorney 12:40 The "Bougie" Reality of Going Solo (Missing an IT Dept) 21:30 The Trap: Switching to "All-in-One" Legal Software 32:15 Invisible Tasks & Calendar Nightmares 41:50 Tech Support Gaslighting ("It's Not User Error") 50:10 The Turning Point: Paying a Fee to Fire My Software 56:45 Building a Custom Stack on Microsoft 365 1:04:20 Future Proofing: Scanning Physical Books for AI 1:10:30 Final Advice: Review Your Contracts Now Where are you right now? Take the free Level of Consciousness Assessment: jcaresse.com/podcast Watch this conversation on YouTube: youtube.com/watch?v=wbrSffnN-7k Connect with Jessica: jcaresse.com

    Escaping the Tech Trap: How Melissa O’Connor Rebuilt Her Firm from the Ground Up

  8. 10/21/2025

    Why Playing It Safe Keeps You Stuck — A Conversation with Kaila Sachse

    She quit a toxic job with no backup plan, right before vacation. Then she built a design agency. Kaila Sachse, founder of Yuri Digital, on leaving medical school and building a creative business. Kaila Sachse, founder of Yuri Digital, walks me through her non-linear path from medical school to mapping rhinestones on tracksuits to running a full-service design agency. You will learn why she stopped billing hourly, how SCORE mentors helped her, and how she hires people who care about the work as much as she does. Chapters 00:00 The "Buy the Ticket Anyway" Story 02:45 The Med School vs. Art School Pivot 08:15 Toxic Work Culture: Getting Scolded for a Birthday Party 12:30 How a Dream Board Party Led to the First Client 17:00 The "Voicemail" That Changed Everything 21:40 Why You Shouldn't Quit Without a Plan (Usually) 25:20 Scaling: Moving from Freelancer to Agency Owner 29:10 Pricing Strategy: Moving from Hourly to Flat Fee/Subscription 34:00 Hiring & "Coachability" in Creative Teams 39:45 The Power of SCORE Mentors for Small Business 44:10 Internal Value: Overcoming Imposter Syndrome Where are you right now? Take the free Level of Consciousness Assessment: jcaresse.com/podcast Watch this conversation on YouTube: youtube.com/watch?v=NRpCfSBfZHw Connect with Jessica: jcaresse.com

    Why Playing It Safe Keeps You Stuck — A Conversation with Kaila Sachse
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5
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About

Conversations with leaders who love their work, and found a way to carry it without losing themselves. I spent years as the one holding everything together at work, and I know what it costs. Here, executives, founders and operators talk honestly about the moment success stopped feeling like success, and what they changed: in the process, the team, the tools, and in themselves. Every episode connects one problem at work to the one inside. You leave with one thing to change at work, and one thing to change in yourself. Where are you right now? Take the free Level of Consciousness Assessment: jcaresse.com/podcast Quielimens, my daily practice for leaders, is coming soon. Join the waitlist: jcaresse.com/wellness Jessica Caresse is Managing Director of J.Caresse & Company, an operations and AI transformation firm. jcaresse.com

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