Comfort To Courage

Jen Josey
  • 5.0 (22)
  • Entrepreneurship
  • Updated Weekly

Comfort to Courage Because courage is contagious. Hosted by Jen Josey, the Bestower of Badassery™, Comfort to Courage is a weekly podcast featuring inspiring conversations with people whose bold decisions changed the course of their lives. Every episode proves one simple truth: when one person chooses courage over comfort, it gives someone else permission to do the same. Maybe you're standing at the edge of a decision you've been avoiding: a career change, a business launch, a difficult conversation, a health challenge, or simply the next chapter of your life. Whatever your crossroads, this isn't another motivational podcast built on hustle culture or empty inspiration. It's a collection of honest stories that remind you that stepping into the unknown is not only survivable, it can also be life-changing. Each episode begins with Jen's Badassery Bestowment, a practical mindset lesson designed to help you grow your courage muscle before diving into an authentic conversation with someone who made the leap. Together, you'll uncover the turning point that changed everything, the obstacles they faced, and what they discovered on the other side. Every episode ends with a Courage Challenge: one small, actionable step you can take to move from comfort to courage in your own life. Whether you're navigating entrepreneurship, career transitions, personal growth, recovery, relationships, reinvention, resilience, or simply trying to become the person you know you're capable of being, you'll leave every episode with practical wisdom, renewed confidence, and the motivation to take your next bold step. New episodes every week. Because courage is contagious... and your story could be the one that inspires someone else. Subscribe to Comfort to Courage and start building the life waiting for you on the other side of your comfort zone.

  1. 11h ago

    319 - From 20 Years in Corporate to 90,000 Followers: Nicole Fiorella on AI, Automation, and Betting on Yourself

    What happens when the identity you built for two decades stops fitting the life you actually want? Nicole Fiorella spent over 20 years climbing the corporate ladder in pharmaceutical, biotech, and medical talent acquisition, building the kind of career most people would call secure. Then a divorce, a career change, and a location change hit her all at once, not once, but twice in her life, and she chose to rebuild from scratch instead of staying comfortable. In this episode, Nicole breaks down exactly how she turned two decades of corporate systems thinking into a business that now reaches more than 90,000 entrepreneurs and professionals across Facebook, Instagram, and LinkedIn. She shares the skill-stacking strategy that gave her an edge as an early adopter of every major platform since 2004, the real financial and emotional cost of walking away from a stable paycheck, and a practical framework for using AI tools like Claude, ChatGPT, and Gemini to find your business's immediate constraint instead of drowning in a to-do list. She also gets candid about the $1,200 lesson that taught her to never post content she doesn't own, and the mindset shift that lets her stay grounded through repeated life upheaval. This episode is for the service-based entrepreneur who feels chained to social media, the corporate professional wondering if there's more, and anyone rebuilding an identity after a major life change. If you've ever felt overwhelmed by AI, unsure how to grow an audience without burning out, or afraid to bet on a new version of yourself, Nicole's story and strategy are exactly what you need to hear right now. 5 Powerful Takeaways Skill stacking, not starting over, is what turns a corporate background into a unique competitive edge in a new industry. Naming your business's single immediate constraint (not trying to fix everything at once) is the fastest path to real progress. Using AI "projects" or custom knowledge bases, instead of one long ongoing chat, keeps your results sharper and your usage costs down. Growing a real audience isn't about chasing virality. It's about consistently solving one specific problem at a time. Protecting your reputation legally and financially before you need to is cheaper than learning the hard way. 00:00 Courage Is Contagious 01:22 Badassery Bestowment 04:30 Meet Nicole Fiorella 06:35 Breaking Social Media Chains 08:57 AI Tools And Invisible List 14:01 Leaving Corporate Comfort 19:38 Costs Of Going Solo 21:35 Growing A Following 27:55 AI Automation Workflow 33:49 Courage Challenge 35:05 Badass Rapid Fire 41:31 Where To Find Nicole 42:25 Final Sendoff About the Guest Nicole Fiorella is a business strategist and AI-driven marketing expert who helps service-based entrepreneurs simplify, scale, and reclaim their time through proven ad frameworks and automation systems. Before launching her own business, she spent more than 20 years in corporate strategy, operations, and talent acquisition within the pharmaceutical, biotech, and medical industries. Today she mentors service providers, from med spas to creative agencies, on using AI and marketing to generate consistent, high-quality leads without relying on social media around the clock. Her community has grown to more than 90,000 entrepreneurs and professionals across Facebook, Instagram, and LinkedIn, with her content regularly reaching tens of thousands of viewers each month. Resources & Websites Mentioned Website: nicolefiorella.com Instagram: @thenicolefiorella YouTube: @nicolefiorella Book: The Next Conversation by Jefferson Fisher App mentioned: Granola (AI note-taking app) Connect With Jen Josey To learn more about Jen Josey, visit https://www.therealjenjosey.com/ If you enjoy Jen's Witty Shirts, shop the whole collection at https://www.shopwittygoods.com/ New episodes drop every Monday at 6am EST. See you next time.

  2. 11h ago ·  Bonus

    You Might Also Like: The Ben Shapiro Show

    Introducing Ep. 2504 - One Year Since Charlie Kirk’s Murder... What The Hell Happened?! from The Ben Shapiro Show. Follow the show: The Ben Shapiro Show One year after Charlie Kirk's assassination, we discuss what should have happened... and why it didn't; we're joined by TPUSA's Andrew Kolvet; and Victor Davis Hanson stops by to explain what's likely to happen in the post-Trump GOP. Ep. 2504 - - - Turning Point USA:  Help chase ballots this mid-term election by joining Turning Point Action. Visit: https://www.tpaction.com/commit100 Join a chapter or start a new one at: https://tpusa.com AmericaFest "AmFest" is December 17th-20th in Phoenix, Arizona. Buy tickets today! https://www.amfest.com - - - "The Counter Revolution: The Fall and Rise of Donald Trump and the MAGA Movement" by Victor Davis Hanson is available here: https://a.co/d/0hVmFOKD - - - Today's Sponsors: PureTalk - There's a better wireless choice out there. And at just fifteen bucks a month for your first three months on ANY plan... now's a great time to choose PureTalk. Simply go to https://PureTalk.com/SHAPIRO to claim this offer. Helix Sleep - Go to https://helixsleep.com/ben for 27% off sitewide during Helix's Labor Day sale. - - - DailyWire: Become a Daily Wire Member and watch all of our content ad-free: https://www.dailywire.com/subscribe 🎆 🇺🇸 Celebrate America 250 with 3-Months of DailyWire for just $17.76 📜 📲 Download the free Daily Wire app today on iPhone, Android, Roku, Apple TV, Samsung, and more. 📰 Follow me on the Daily Wire app or DailyWire.com to read my daily articles and receive my Friday newsletter. 🍿 Run Hide Fight: Infidels will premiere on The Daily Wire, Wednesday September 16th. 📘 My book "Lions and Scavengers: The True Story of America (and Her Critics)" is available here:  https://dwplus.shop/LionsandScavengers 👕 Get your Ben Shapiro merch here: https://dwplus.shop/BenShapiroMerch - - - Socials: YouTube — https://youtube.com/@BenShapiro Facebook — https://www.facebook.com/officialbenshapiro Instagram — https://www.instagram.com/officialbenshapiro Snapchat — https://www.snapchat.com/officialbenshapiro TikTok — https://www.tiktok.com/@real.benshapiro X — https://twitter.com/benshapiro - - - Privacy Policy: https://www.dailywire.com/privacy Learn more about your ad choices. Visit podcastchoices.com/adchoices DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to team@podroll.fm.

  3. Sep 7

    318 - From Corporate SVP to Spiritual Practitioner: Dr. Brandon Croud's Courage to Answer a Deeper Calling

    318 - From Corporate SVP to Spiritual Practitioner: Dr. Brandon Croud's Courage to Answer a Deeper Calling What happens when you spend 20 years climbing the corporate ladder, checking every box the world told you to check, and then one night a TikTok rabbit hole cracks your entire identity open? Dr. Brandon Croud knows exactly what that feels like. After building a two-decade career in mortgage underwriting and rising to Senior Vice President, while simultaneously becoming a nationally recognized podcast host interviewing NASCAR legends, Brandon walked away from all of it. Not because he failed. Because something deeper finally refused to be ignored. In this episode of Comfort to Courage, Dr. Brandon Croud breaks down what a spiritual awakening actually looks like from the inside, including the moment his young son's fascination with the moon cracked open abilities Brandon had suppressed since childhood. He shares what it really means to reset your nervous system, why inner child healing is the real work beneath every surface-level habit change, and how releasing guilt and regret is the first step toward true abundance. Brandon also unpacks why the five people closest to you are already shaping your ambition, your standards, and your ceiling, whether you've noticed it or not, and what it took to trade a guaranteed paycheck for a life built entirely on purpose. If you're sitting in a job that pays the bills but costs you your soul, this episode is for you. Whether you've been too afraid to follow a calling that doesn't fit neatly on a resume, or you're already deep in a life pivot and need proof that it's possible, Dr. Brandon Croud's story is both permission and evidence. He went from SVP to spiritual practitioner, from corporate certainty to real freedom, and he's here to tell you exactly how he made the leap and what was waiting on the other side. 00:00 Courage Is Contagious 01:25 Support System Audit 04:45 Meet Dr Brandon Croud 06:52 Awakened Croud Origins 09:12 Tarot Coaching Offerings 12:32 Alden And The Moon 15:51 Corporate Success Inside 18:41 TikTok To Awakening 21:38 Layoff And Reinvention 24:33 Nervous System Healing 25:34 Resetting Your Nervous System 27:00 Peeling Back Reactions 28:22 Awakening and Inner Child 30:12 Lion's Gate Portal 34:16 Forgiveness and Abundance 36:17 Trust Your True Self 39:24 Courage Challenge Journaling 42:02 Badass Book and Formula 44:05 Advice Doubt and Goals 46:14 Strength Success and Wrap 5 Powerful Takeaways The five people you spend the most time with are already normalizing your standards, your fears, and your comfort zone. Auditing your circle might matter more than auditing your habits. Resetting your nervous system isn't about willpower. It starts with paying attention to how your body reacts to everyday triggers and tracing those reactions back to their origin. Inner child healing is the layer underneath every pattern you can't seem to break. Telling your younger self they're safe is some of the most powerful and underrated work you'll ever do. Releasing guilt and regret isn't about excusing the past. It's the prerequisite to attracting abundance, because the energy you project outward is exactly what gets reflected back to you. Journaling, or speaking out loud if writing isn't your thing, is the fastest way to start hearing your true self clearly instead of all the external noise that's been making your decisions for you. About the Guest Dr. Brandon Croud is an author, speaker, podcast host, business consultant, and metaphysical practitioner who helps people bridge the gap between practical success and authentic living. He spent over two decades leading corporate underwriting teams, rising to Senior Vice President of Credit Underwriting, and simultaneously built a nationally recognized podcast interviewing NASCAR legends and championship crew chiefs. After a profound spiritual awakening, Brandon earned his PhD in Metaphysics and founded The Awakened Croud, a practice offering spiritual coaching, tarot readings, chakra alignment, inner child healing, and immersive local experiences like his signature card charcuterie and champagne nights. He is also the author of the children's book Alden and the Light That Blinked Back, a tool for parents who want to nurture curiosity, wonder, and spiritual awareness in young children. Based in Metro Detroit, Brandon brings a rare combination of corporate credibility, metaphysical depth, and genuine warmth to every conversation. Resources & Websites Mentioned The Awakened Croud: https://www.theawakenedcroud.com Alden and the Light That Blinked Back by Dr. Brandon Croud: available on Amazon The Formula by Bashar/Darryl Anka (book recommendation from the BADASS segment) Connect With Jen Josey To learn more about Jen Josey, visit https://www.therealjenjosey.com/ If you enjoy Jen's Witty Shirts, shop the whole collection at https://www.shopwittygoods.com/ New episodes drop every Monday Morning at 6am EST. See you next time!

  4. Aug 31

    317 - Robin Reed-Hicks Didn't Wait for Cancer. She Chose a Double Mastectomy and Became a Previvor.

    After 25 years of biopsies, scans, and being told to just "keep monitoring it," Robin Reed-Hicks finally asked the question most women are too afraid to ask their doctors: why am I waiting for cancer to show up before I'm allowed to do something about it? In this episode, Robin shares the decision that turned her into a previvor: someone who takes proactive action before a diagnosis ever arrives, not after. Robin walks through the entire arc of her 25 year medical journey, from her first surgical breast biopsy in her early twenties to the moment a doctor told her that a benign diagnosis still carried a 43 percent chance of developing into breast cancer within a decade. She unpacks what it actually took to push past a system that kept telling her to wait and watch, how she advocated for the surgery she wanted instead of the one she was offered, and what nobody tells you about drains, tissue expanders, and rebuilding your body from the inside out. Her story is a masterclass in self-advocacy inside a medical system that isn't always built to move as fast as your instincts. This episode is for anyone who has ever been told to "just keep an eye on it," anyone managing a health scare that keeps circling back, and anyone who has ever doubted their own read on their own body. If you have ever felt dismissed by a doctor or unsure whether your concern was "enough" to push for answers, Robin's story is proof that trusting yourself is not overreacting. It's survival. 5 Powerful Takeaways Why "benign" doesn't always mean safe, and how a specific diagnosis can still carry a double-digit cancer risk How to push back when a provider offers you a smaller solution than the one your situation actually calls for What a preventative double mastectomy really involves, from tissue expanders to nerve-sparing reconstruction How to turn 25 years of medical anxiety into an advocacy platform instead of letting it stay private Why becoming a "previvor" is its own category of courage, separate from a cancer diagnosis or survivorship 00:00 Courage Is Contagious 01:25 Badassery Bestowment 02:21 Five Confidence Moves 05:20 Meet Robin Reed Hicks 07:39 Friends And Flashbacks 09:58 Robin Life And Career 13:23 Gluten Free And Hashimotos 15:31 Lets Talk Boobies 16:53 25 Years Of Surveillance 22:01 The Turning Point Biopsy 26:15 Oncologist And Previvor 28:36 Fighting For Approval 30:03 Surgeon Options Decision 30:48 Mastectomy Types Explained 32:08 Nipple Sparing Risks 34:00 MRI Changes Surgery Plan 35:00 Stage One Lumpectomy Lift 36:51 Double Mastectomy Expanders 37:31 Drains Sensation Recovery 39:32 Exchange Surgery Complications 40:42 Relief Life After Surgery 41:38 Portraits Of Hope Advocacy 45:13 Advice Self Advocacy 47:42 Badass Rapid Fire 55:07 Success Contentment Closing About the Guest Robin Reed-Hicks is a communicator, executive and life coach, real estate professional, voice actor, actress, spokesperson, MC, and content creator who has spent more than 25 years helping people move forward with confidence, clarity, and purpose. She is an ICF associate certified coach who works with executives and individuals through her coaching practice, and she is coming up on 25 years as a working real estate professional. She also hosts the YouTube channel Cook With Me Gluten Free, built around accessible, joyful gluten-free living. After more than two decades of breast biopsies, surgeries, and scans, Robin chose a preventative double mastectomy and reconstruction, becoming a previvor, and was selected as one of only 12 Portraits of Hope ambassadors through the American Cancer Society. Resources & Websites Mentioned https://bookcoachrobin.com YouTube channel: Cook With Me Gluten Free https://knowyourlemons.com Connect With Jen Josey To learn more about Jen Josey, visit https://www.therealjenjosey.com/ If you enjoy Jen's Witty Shirts, shop the whole collection at https://www.shopwittygoods.com/ New episodes drop every Monday Morning at 6am EST. See you next time.

  5. Aug 24

    316 - From Burnout to Betting on Herself: Kim Kelly on Leading Under Pressure

    From Burnout to Betting on Herself: Kim Kelly on Leading Under Pressure What happens when the version of you that looks the most successful on paper is actually the most unwell you've ever been? Kim Kelly spent two decades advising Fortune 500 companies, leading global teams, and making decisions with hundreds of millions of dollars riding on the outcome. From the outside, it looked like she had it all figured out. On the inside, she wasn't sleeping, wasn't eating, and was waking up at 2am in a full-blown panic, until her body forced her to stop. In this episode, Kim opens up about the medical leave that became the turning point of her life and the four-pillar Lead Under Pressure Framework she built out of it: seeing clearly, owning your state, aligning to what matters, and executing with discipline. She shares what it actually looked like to rebuild trust with herself, why she believes endurance is built alone but resilience is built with others, and the exact moment she decided to leave a stable, high-paying career to launch her own consulting practice, AVENNI, named after her two children. Jen also delivers a bonus Badassery Bestowment on making faster decisions, a skill Kim herself puts directly into practice. This episode is for the high-achiever who is quietly running on fumes and calling it dedication, the leader who has confused pushing through with actually being okay, and anyone standing at the edge of a career pivot they haven't given themselves permission to make yet. If you've ever needed someone to tell you that slowing down is not the same as falling behind, this conversation is your permission slip. 5 Powerful Takeaways Why "endurance built alone" and "resilience built with others" are two completely different things, and which one is actually sustainable long-term The four-pillar Lead Under Pressure Framework Kim uses to help leaders make clear-headed decisions without burning out How Kim went from a private medical leave to launching her own company in a single week, and what finally made the leap feel possible A simple gratitude-based practice for the exact moment you wake up at 2am spiraling about everything you have to do Why treating every decision like it's permanent is quietly draining your confidence, and how to tell which ones you can actually reverse 00:00 Courage Is Contagious Intro 01:27 Badassery Bestowment Decisions 02:32 Five Ways to Decide Faster 05:30 Meet Kim Kelly 07:54 AVENNI Mission And Name 09:41 Corporate Success Burnout 13:22 Medical Leave Turning Point 15:43 Building Resilience With Others 20:26 Leaving Corporate, Starting AVENNI 23:43 Lead Under Pressure Pillars 29:38 Advice For Running On Fumes 32:15 Badass Segment Rapid Fire 37:39 Success Definition And Wrap 40:24 Final Sendoff Courage Challenge About the Guest Kim Kelly is a leadership consultant, keynote speaker, and founder of AVENNI, a consulting practice built around her Lead Under Pressure Framework. She spent two decades building and leading global teams inside the workforce solutions industry, advising Fortune 500 organizations on decisions carrying hundreds of millions of dollars in outcomes. After a medical leave forced her to confront how unsustainable her pace had become, Kim combined her background in theater performance with two decades of boardroom experience to build a system for staying clear-headed under pressure. She now works with organizations and leaders, with a particular focus on women and up-and-coming leaders, who are ready to stop white-knuckling their way through stress and start leading through it on purpose. Resources & Websites Mentioned Website: avenniconsulting.com Email: kim@avenniconsulting.com LinkedIn: Kim Kelly AVENNI Instagram: @AVENNI_KimKelly Connect With Jen Josey To learn more about Jen Josey, visit https://www.therealjenjosey.com/ If you enjoy Jen's Witty Shirts, shop the whole collection at https://www.shopwittygoods.com/ New episodes drop every Monday at 6am EST. See you next time!

  6. Aug 17

    315 - She Was Internally Decapitated. 98% Don't Survive. Here's How Angie Breaux Rebuilt Her Real Estate Empire From a Hospital Bed

    315 - She Was Internally Decapitated. 98% Don't Survive. Here's How Angie Breaux Rebuilt Her Real Estate Empire From a Hospital Bed In April 2022, real estate investor Angie Breaux was on the verge of closing a 120-home rental portfolio, sitting on a $200,000 stake in a cannabis facility, and building toward becoming the first millionaire in her family. Then a single car accident internally decapitated her, a survivable event in only two percent of cases. Most people who live through it never walk again. Angie not only walked again, but she also picked up her phone from a hospital bed, still wheelchair bound, and closed a real estate deal. This episode is the full story behind that moment. Angie walks through what it actually felt like to lose everything she had built while she was in a medically induced coma, the four-year recovery that included multiple surgeries on both arms and her eye, and the mindset shift that let her start over completely from zero. She gets specific about the financial reality no one warns you about after a catastrophic injury, what it took to trust her business partners after they closed the 120-door deal without her, and the exact moment she decided to get back into real estate investing after four years away from it. This is a conversation about identity, loss, and what it really means to rebuild. If you have ever lost something you spent years building, whether it was a business, your health, or your sense of who you are, this episode is for you. Angie's story proves that starting over is not the same as starting from nothing, and that the comeback can be even bigger than the version of success you originally planned. Anyone facing a setback that feels too big to come back from needs to hear this one. 5 Powerful Takeaways How Angie closed a real estate deal from a hospital bed while still wheelchair bound, and what that moment taught her about momentum Why she refuses to blame her former business partners for closing their 120-unit deal without her, and the mindset behind that decision The financial reality of surviving a catastrophic injury that no one prepares you for, from medical costs to four years without income What actually pushed her back into real estate investing after a four-year gap, and why March 2026 became her turning point Her simple daily gratitude practice for anyone rebuilding after a major loss, and why she still uses it even on the hardest days 00:00 Warning And Welcome 01:20 Badassery Bestowment Rejection 04:54 Meet Angie Breaux 07:06 Rebuilding Real Estate Again 09:28 Cancun Origin Story 11:23 Life Before The Crash 14:38 The April 2022 Accident 16:46 Internal Decapitation Explained 17:59 Coma Surgeries And Recovery 20:06 Losing The 120 Doors 21:06 Closing A Deal From Hospital 22:27 Dealmaker Turning Point 24:46 Goals Speaking And Support 27:29 Courage Challenge Gratitude 29:47 Badass Q And A 39:54 Redefining Success And Farewell About the Guest Angie Breaux is a real estate investor who built her business from scratch in Mississippi starting in 2019, expanding into two states and closing in on a 120-home rental portfolio with two business partners by 2022. In April of that year, a car accident left her internally decapitated, a survivable injury for only two percent of the people it happens to. She spent four to five weeks in a coma, endured multiple complex surgeries on both arms and her right eye, and was told she would never drive again. Two months before this recording, she passed her driver's test. Angie is now rebuilding her real estate investment business, pursuing flips and rentals, and working toward public speaking so she can share her story with others navigating catastrophic loss. Resources & Websites Mentioned Never Split the Difference by Chris Voss Mic Drop Club (women's speaking and workshop community) Dealmaker conference Connect With Jen Josey To learn more about Jen Josey, visit https://www.therealjenjosey.com/ If you enjoy Jen's Witty Shirts, shop the whole collection at https://www.shopwittygoods.com/   New episodes drop every Monday Morning at 6am EST. See you next time.

  7. Aug 10

    314 - Rock Bottom, Recovery, and the Red Hat: Larry Roberts on Losing Everything and Choosing Courage

    314 - Rock Bottom, Recovery, and the Red Hat: Larry Roberts on Losing Everything and Choosing Courage He had 12 years of sobriety, a thriving podcast production company, a recognizable personal brand, and a speaking career that put him on stages across the country. And then, quietly and completely, he lost all of it. In this episode of Comfort to Courage, Larry Roberts, founder of Red Hat Media and one of the most recognized voices in the podcasting world, pulls back the curtain on his very public and brutally honest battle with alcoholism, including multiple rehab stints, a DUI, a dissolved business partnership, near-death, and the moment a phone call he almost didn't answer saved his life. Larry doesn't sugarcoat a single chapter of this story. He walks through how 12 years of sobriety left him dangerously overconfident, how his drinking exploded from a couple of shots before a speaking engagement to a seven-week stretch where he ate just five cups of noodles, and how he ended up in a San Diego recovery facility on day 51 with no income, a dissolved business, and a marriage hanging by a thread. What makes Larry uniquely worth listening to is not just how far he fell, but what he's choosing to do next. He talks candidly about rebuilding Red Hat Media, an upcoming AI-powered podcast production tool he's developing, and the mindset shifts that are making this recovery attempt different from the ones that came before. This episode is for anyone who has ever hit a wall and wondered if there's a way back. It's for entrepreneurs who have watched a business they built from scratch fall apart. It's for anyone who has been touched by addiction, in their own life or someone else's, and needed proof that asking for help is not weakness. It is the bravest thing you can do. If you're standing at the base of a steep hill and you're not sure you have what it takes to climb it, Larry Roberts just spent the better part of an hour showing you it's possible. 5 Powerful Takeaways Isolation makes recovery impossible: Larry explains why going dark and cutting off his entire network was the single most destructive decision he made, and how one vulnerable phone call set everything in motion toward healing. Twelve years of sobriety can become a trap: Larry reveals how his previous success staying sober created a dangerous arrogance that left him completely unprepared when alcohol came back into his life. Brand damage is survivable: After going silent on social media for nearly 10 months and burning real professional bridges, Larry lays out the exact mindset he's using to rebuild Red Hat Media from scratch. The "God smack" moment is real: Larry shares the story of a phone call from a recovery facility that came in the exact window when he had stopped answering his phone and had quietly accepted he might not survive the week. Affirmations aren't soft, they're strategic: Inspired by David Goggins, Larry explains why writing and repeating daily affirmations is one of the highest-leverage tools available to anyone trying to rewire their mindset from a place of rock bottom. About the Guest Larry Roberts is the founder of Red Hat Media, a podcast production, branding, and AI solutions company he built into a nationally recognized platform. Known across the industry as the Red Hat Guy, Larry has spoken on major stages including PodFest, consulted with brands on positioning and content strategy, and amassed a loyal following under the handle @TheLarryRoberts across social media. He authored the book Under the Red Hat, exploring how personal identity shapes brand power. He is currently in recovery in San Diego and is developing an AI-powered podcast production tool with a projected launch at PodFest, aiming to remove up to 90 percent of manual production from the podcasting workflow. 00:00 Courage Is Contagious 01:17 Badassery Bestowment 02:12 Five Courage Reps 04:48 Meet Larry Roberts 06:22 Red Hat Media Origin 09:50 Branding And AI Expansion 11:29 Red Hat Pushback 13:31 Relapse And Rock Bottom 19:08 Rehab Spiral And DUI 25:14 Rebuilding The Red Hat 27:34 Jen Reacts And Support 29:02 Why This Time Sticks 31:10 Hitting Rock Bottom 32:56 Sober Living Reality Check 34:12 First Steps to Sobriety 35:30 Finding Rehab Options 38:20 Mindset and Affirmations 40:15 Badass Rapid Fire 43:16 AI Podcast Production Dream 46:16 Strength and Success Redefined 48:34 Where to Find Larry 49:33 Final Send Off Resources & Websites Mentioned Larry Roberts website: https://www.larryroberts.com Larry Roberts on social media (Instagram, Facebook, LinkedIn): @TheLarryRoberts Book by Larry Roberts: Under the Red Hat Book recommended by Larry: Extreme Ownership by Jocko Willink Connect With Jen Josey To learn more about Jen Josey, visit https://www.therealjenjosey.com/ If you enjoy Jen's Witty Shirts, shop the whole collection at https://www.shopwittygoods.com/ New episodes drop every Monday Morning at 6am EST. See you next time.

  8. Jul 20

    313 - How Alpha Funding Gets Investors to the Closing Table Fast with Vance Josey

    You found the deal. You ran the numbers. And then you lost it to another investor because your lender couldn't get you a proof of funds letter over the weekend. If that scenario makes your stomach drop, this episode is about to change how you fund every deal from here on out. Jen sits down with her husband and business partner Vance Josey, real estate broker, general contractor, and hard money lending expert with Alpha Funding, to pull back the curtain on how investors actually get deals financed. Vance breaks down the difference between prequalification and underwriting, why speed matters more than the lowest rate, and exactly what loan-to-value percentages look like for brand new investors versus those with six or more deals under their belt. He also reveals how to fund a deal with none of your own cash using unsecured lines of credit, what red flags make an underwriter nervous, and the exact habits that make you a borrower lenders want to keep working with. Whether you're brand new to fix and flip investing or you've been doing this for years and want faster, more reliable funding, this conversation gives you the insider playbook most investors never get. If you've ever been outbid because your financing was too slow, or you're wondering how to scale without draining your own bank account, you need to hear this one. 5 Powerful Takeaways How to get an instant proof of funds letter so you can compete and win in multiple-offer situations, without waiting on your lender The exact loan-to-value percentages for new versus experienced investors, and how completing just six deals unlocks significantly better terms How to fund a deal with none of your own cash using unsecured lines of credit through Alpha Funding's partner MB Alpha What underwriters actually look for behind the scenes, and how to avoid the kind of last-minute closing disaster that can cost you a deal The simple communication habits that make you a "good borrower" lenders want to keep funding, especially when a project runs long or over budget 00:00 Welcome to REIGN 01:03 Build Your Power Team 03:16 Meet Vance Josey 04:29 Alpha Funding Overview 06:05 Prequalification and Proof Funds 07:59 Lending for New Investors 08:58 Loan Products Explained 09:39 Fix and Flip Numbers 11:10 DSCR Refinance Basics 12:09 No Money Down Strategies 13:31 Underwriting Behind Scenes 15:06 Be a Great Borrower 17:24 Where They Lend and Next Steps 20:00 Badass Acronym Rapid Fire 25:53 Podcast Rebrand Announcement 27:59 Final Thanks and Sign Off About the Guest Vance Josey spent nearly 30 years climbing the ranks in corporate manufacturing before stepping into real estate full time. A graduate of Appalachian State University with a degree in accounting, Vance co-founded Jolific Homes with his wife Jen Josey in 2017, renovating homes throughout the Raleigh, North Carolina area. That hands-on experience led him to earn both his real estate broker's license and his general contractor's license, giving him a rare, ground-level understanding of a deal from acquisition through renovation to resale. Today, Vance brings that background to Alpha Funding, a boutique hard money lender based in New Jersey, where he helps investors across 43 states get fix and flip, new construction, DSCR, and bridge loans funded quickly. He and Jen are now also exploring manufactured home development as a path to more affordable housing. Resources & Websites Mentioned alphafunding.com vance@alphafunding.com Call to Action To learn more about Jen Josey, visit https://www.therealjenjosey.com/ To join REIGN, visit https://www.reignmastermind.com/ Stuff Jen Josey Loves: https://www.reignmastermind.com/resources Buy Jen Josey's Book: From Beginner to Badass: https://a.co/d/bstKlby

See All (320)

5
out of 5
22 Ratings

About

Comfort to Courage Because courage is contagious. Hosted by Jen Josey, the Bestower of Badassery™, Comfort to Courage is a weekly podcast featuring inspiring conversations with people whose bold decisions changed the course of their lives. Every episode proves one simple truth: when one person chooses courage over comfort, it gives someone else permission to do the same. Maybe you're standing at the edge of a decision you've been avoiding: a career change, a business launch, a difficult conversation, a health challenge, or simply the next chapter of your life. Whatever your crossroads, this isn't another motivational podcast built on hustle culture or empty inspiration. It's a collection of honest stories that remind you that stepping into the unknown is not only survivable, it can also be life-changing. Each episode begins with Jen's Badassery Bestowment, a practical mindset lesson designed to help you grow your courage muscle before diving into an authentic conversation with someone who made the leap. Together, you'll uncover the turning point that changed everything, the obstacles they faced, and what they discovered on the other side. Every episode ends with a Courage Challenge: one small, actionable step you can take to move from comfort to courage in your own life. Whether you're navigating entrepreneurship, career transitions, personal growth, recovery, relationships, reinvention, resilience, or simply trying to become the person you know you're capable of being, you'll leave every episode with practical wisdom, renewed confidence, and the motivation to take your next bold step. New episodes every week. Because courage is contagious... and your story could be the one that inspires someone else. Subscribe to Comfort to Courage and start building the life waiting for you on the other side of your comfort zone.

Information

  • Creator
    Jen Josey
  • Years Active
    2020 - 2026
  • Episodes
    320
  • Rating
    Explicit
  • Copyright
    © REI Growth Network LLC
  • Show Website
    Comfort To Courage