The Greater Journey: Stories of Transformation with Gregory Rutledge

Gregory Rutledge
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  • Entrepreneurship

Everybody wants the highlight reel. Nobody wants to talk about the trenches. The Greater Journey is where we flip that. I sit down with entrepreneurs, leaders, and creatives to unpack the setbacks, the doubts, and the messy middle that actually make you GREATER. Each conversation follows my GREATER framework — Grounded in your story, Reframe your beliefs, Embrace learning, take Action, Transition with purpose, Empower your network, and build Resilience through it all. This isn’t theory, it’s real people sharing the real stories that shaped them. If you’ve ever felt stuck, overlooked, or like you were made for more, these episodes will remind you: your story isn’t the end. It’s the beginning of YOUR greater journey.

  1. 3d ago

    Former Gang Member Can Now Start a Business in His Sleep

    At 18 he left a Dallas gang. In 2002 he was making $7.25 an hour when God promised him he'd be the richest man he knew. Christian entrepreneur Mark Drake shares how he went from no degree to director of operations to running his own businesses, and why you can't have hope without wisdom. 📸 Follow Mark: https://instagram.com/beingmarkdrake 📖 Get Gregory's book, From Waiter to Greater: https://amzn.to/3TRTGQe 🔗 Connect with Gregory: https://linktr.ee/gregoryrutledge 🤖 AI business automation with Scyene Solution: https://scyene.com/ On this episode of The Greater Journey, Gregory Rutledge talks with Mark Drake about faith and business, the year that gave him imposter syndrome, and the three pillars behind his success. In this conversation: • The promise God gave him at $7.25 an hour • Why character beat credentials when he had no degree • "An organized mind is more productive": the playbook for starting a business • Letting go of the Porsche: ego and knowing when to transition • Tracing imposter syndrome back to sixth grade • Three pillars: keep your heart right, give God something to work with, find someone to serve • Partnership before profit • Resilience: perspective from a pastor who once faced 20 years in prison CHAPTERS 0:00 Gang member, $7.25 an hour, and a promise from God 0:40 Welcome to The Greater Journey 1:58 Growing up in Pleasant Grove 6:55 The promise in 2002 11:20 You can't have hope without wisdom 17:05 An organized mind: the Super Bowl playbook 21:07 Business is structure, not feelings 26:16 Start in a Porsche, finish on a bike 29:50 Tracing imposter syndrome to sixth grade 36:49 3 pillars: heart right, give God something, serve 39:15 Partnership before profit 46:25 Resilience: facing 20 years 52:53 What greater means to Mark 54:38 Stuck? Take one step back 56:15 Connect with Mark 💬 Which of the three pillars do you need most right now? Tell us below. #ChristianEntrepreneur #FaithAndBusiness #TheGreaterJourney 📖 Get Gregory's book, From Waiter to Greater: https://amzn.to/3TRTGQe 🔗 Connect with Gregory: https://ceogregory.com (Ask me about a free card!)

  2. Oct 26

    He Was Scared to Send a Bill. The Reason Went Back to Childhood.

    Jason McKenzie had run his business for over a decade when he suddenly got scared to send a bill. The reason went back to childhood. On The Greater Journey, Christian entrepreneur Jason McKenzie, founder of Boise Web and host of Small Business Big Visibility, shares how he found his money block, why every payment is a thank you, and how he went from "we need you" to taking October off. 🌐 Boise Web: https://boiseweb.net 🎙️ Small Business Big Visibility podcast: [YouTube link — confirm] 👤 Jason on Facebook (Real Jason McKenzie): [link — confirm] 📖 Get Gregory's book, From Waiter to Greater: https://amzn.to/3TRTGQe 🔗 Connect with Gregory: https://linktr.ee/gregoryrutledge In this conversation: • Why a decade of experience didn't stop him from being afraid to bill • The childhood memory behind his money block • Every payment is an expression of gratitude • "Are you willing to receive it?" • Why serving everyone means you're nothing to anyone • Building a business that runs without you • Failing over and over, and the price you pay for greatness • Paul's thorn: making greatness out of what won't go away CHAPTERS 0:00 Scared to send a bill after 10 years 0:49 Welcome to The Greater Journey with Jason McKenzie 2:07 Candy, basketball and Dad's first business lesson 5:00 Too scared to speak up in college 7:20 A decade in business and afraid to bill 9:25 The childhood root of his money block 12:32 Every payment is a thank you 14:42 "Are you willing to receive it?" 16:18 Stop trying to serve everyone 21:31 From idea to action: go find a customer 26:44 Fireman Jason and the cage he built 32:58 Your business grows at the speed you grow 36:40 When everything failed and he felt cursed 40:19 What he saw at Myron Golden's event 42:25 Paul's thorn and making greatness out of it 45:33 Two definitions of greater 47:41 For the business owner who feels invisible 49:44 Connect with Jason 💬 Should there be a part two? Tell us in the comments. #ChristianEntrepreneur #MoneyMindset #TheGreaterJourney 📖 Get Gregory's book, From Waiter to Greater: https://amzn.to/3TRTGQe 🔗 Connect with Gregory: https://ceogregory.com (Ask me about a free card!)

  3. Feb 10

    We’ll Never Turn a Child Away: The Story Behind Waterfall Academy (Audio Only)

    What do you do when both of your sons are diagnosed with autism… and every door you knock on says, “We’re not a fit”? Connie and Angel Rodriguez were a dual-career, doing-everything-right family—until life rewrote the script.  Two diagnoses. 300 doctors’ appointments a year. Savings gone. Fear, anger, and no clear path forward. Instead of giving up, they did something wild. They prayed in an empty building, told God they would never turn away a child for money, and opened Waterfall Academy—a Christ-centered school for kids on the spectrum who were told they “didn’t fit” anywhere else. In this conversation, we talk about: The gut-punch of a second autism diagnosis and what it did to their faith“God kisses”: the grocery store stranger, the therapist down the road, and the 14-hour flight that changed everythingWhy they promised God they’d never refuse a child over money (and how they’ve never missed payroll or a mortgage)How Waterfall Academy helps kids move from “broken label” to Waterfall WarriorPractical hope for parents who feel alone, exhausted, and out of options If you’ve ever wondered, “Can anything good come out of this pain?”—this episode is your reminder that some stories are too good to not be God. 📖 Get Gregory's book, From Waiter to Greater: https://amzn.to/3TRTGQe 🔗 Connect with Gregory: https://ceogregory.com (Ask me about a free card!)

  4. Jan 3

    From Near-Death to Superconscious: How Kelly Mason Turned a Miracle Into a Mission (Audio Only)

    What happens when your ego becomes your god… and God literally throws you off your high horse? In this episode of The Greater Journey, I sit down with Kelly Mason – filmmaker, healer, and founder of Kula Paradise Academy – whose life changed after a galloping racehorse accident, a near-death experience, and a documented medical miracle that doctors couldn’t explain. We dive into: Her near-death experience and what she saw “on the other sideHow her shattered arm miraculously realigned on the operating table Why ego, identity, and “fake rich” culture keep us stuck in the illusion How to understand soul contracts, assignments, and the real reason you’re here The difference between healing, enabling, and embodying your purpose How to build a life in alignment with God, service, and your superconscious nature If you’ve ever felt like you’re “doing all the things” but still feel empty, misaligned, or spiritually hungry… this conversation is going to hit deep. 📖 Get Gregory's book, From Waiter to Greater: https://amzn.to/3TRTGQe 🔗 Connect with Gregory: https://ceogregory.com (Ask me about a free card!)

  5. 11/16/2025

    From Chaos to Clarity: How Coach Will Smith Found His Purpose (Audio Only)

    In this raw and powerful episode of The Greater Journey, host Gregory Rutledge sits down with Coach Will Smith, founder of Lifestyle Coaching Academy and creator of the New Me Initiative — a 90-day, no-excuses, results-driven transformation program. Will’s story takes us from foster care, addiction, and self-destruction to fatherhood, redemption, and purpose. He reveals how a single wake-up call changed everything and why he believes in accountability over excuses. 🎧 What you’ll learn: The truth about “overnight success” (it’s a 10–20-year night)How to stop blaming and start becomingThe mindset shift from victim to victorWhy peace beats “crazy busy” every timeHow resilience is built through fire, not comfortThe daily habits that keep him grounded and focusedWhy empowering your network starts with owning your story “It’s easy to be comfortable. It’s hard to be great. And just two more letters to be GREATER.” #TheGreaterJourney #FromWaiterToGreater #CoachWillSmith #LifestyleCoachingAcademy #NoExcuses #MindsetShift #Resilience #Accountability #PurposeDriven #NewMeInitiative #EntrepreneurMindset #FaithAndFocus #GreaterFramework #MenWhoLead #FromFireToFocus 📖 Get Gregory's book, From Waiter to Greater: https://amzn.to/3TRTGQe 🔗 Connect with Gregory: https://ceogregory.com (Ask me about a free card!)

  6. 11/11/2025

    She Turned Rejection Into Rhythm—The Power of Starting Anyway (Audio Only)

    In this episode of The Greater Journey, host Gregory Rutledge sits down with Lindsay “Boog” Yancey, founder of No Hook, LNY Bar Services, and LNY Assistant Services. From dreaming of dancing on stage to managing artists and building her own brand, Lindsay shares how trial and error, resilience, and purpose turned rejection into rhythm. 🎧 What you’ll learn: How discouragement can redirect—not destroy—your destinyWhy trial and error is the fastest teacher in entrepreneurshipHow to build something no one can take from youThe power of starting before you’re ready and learning as you goWhat “automate repetition, not relationship” looks like in real lifeThe truth about imposter syndrome and how to keep going when you feel stuckHow purpose evolves through pain, persistence, and communityCore quote: “Every time I felt like quitting something… something came up.”Boog’s story proves you don’t need permission—just the courage to start. 📖 Get Gregory's book, From Waiter to Greater: https://amzn.to/3TRTGQe 🔗 Connect with Gregory: https://ceogregory.com (Ask me about a free card!)

  7. 11/03/2025

    Dirty Energy & Divine Purpose: Jeff Caliguire on Finding Your Calling Beyond Burnout (Audio Only)

    In this heartfelt episode of The Greater Journey Podcast, Gregory Rutledge sits down with Jeff Caliguire—7-time author, former pastor, and founder of WeTrainCoaches.com—to explore the cost of living outside your calling. Jeff shares his raw story of serving in ministry, battling depression, and finally discovering what he calls “clean energy”—the place where your purpose and peace align. Together, they unpack:  🔥 How burnout is often a sign you’re operating outside your true design.  ⚡ Why trying to “be Myron Golden” will never work—and what to do instead.  💡 The 4 essential “checks” for a fulfilled life: Paycheck, People, Purpose, Play. 🕊️ How to trade performance-based faith for God-centered confidence. ❤️ Why courage isn’t hype—it’s living from the heart. If you’ve ever felt trapped by your title, tired from trying, or torn between faith and fulfillment—this one’s for you. 📖 Get Gregory's book, From Waiter to Greater: https://amzn.to/3TRTGQe 🔗 Connect with Gregory: https://ceogregory.com (Ask me about a free card!)

  8. 11/03/2025

    Forged in the Fire: CJ C Boyd on Reinvention, Resilience, and Rising After Ruin (Audio Only)

    When life knocked her down—hard—CJ C Boyd didn’t rise from the ashes. She was forged in the fire. In this powerful episode of The Greater Journey Podcast, Gregory Rutledge sits down with CJ C Boyd—founder of Queen by Design and host of Awaken the Warrior—to unpack what it really means to rebuild after loss. After losing her children, her marriage, and her café, CJ had every reason to quit. Instead, she discovered the warrior within.  Together, Gregory and CJ explore:  🔥 How to unlearn the “rules and roles” that keep women small.  🔥 Why the fire doesn’t destroy—it refines.  🔥 How faith and identity intersect in reinvention.  🔥 The power of charging for transformation (not validation).  🔥 Why authenticity after 50 might be your greatest advantage. If you’ve ever felt forgotten, overlooked, or underestimated, this episode will remind you of one truth:  You were never meant to rise quietly. You were meant to be forged greater. 📖 Get Gregory's book, From Waiter to Greater: https://amzn.to/3TRTGQe 🔗 Connect with Gregory: https://ceogregory.com (Ask me about a free card!)

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About

Everybody wants the highlight reel. Nobody wants to talk about the trenches. The Greater Journey is where we flip that. I sit down with entrepreneurs, leaders, and creatives to unpack the setbacks, the doubts, and the messy middle that actually make you GREATER. Each conversation follows my GREATER framework — Grounded in your story, Reframe your beliefs, Embrace learning, take Action, Transition with purpose, Empower your network, and build Resilience through it all. This isn’t theory, it’s real people sharing the real stories that shaped them. If you’ve ever felt stuck, overlooked, or like you were made for more, these episodes will remind you: your story isn’t the end. It’s the beginning of YOUR greater journey.

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