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. 2d ago

    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.

  2. 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.

  3. 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

  4. Jul 13

    312 - She Left Caregiving to Build Luxury Memory Care Mansions with Nicole Becerra

    She watched residents cry alone on the floor, calls for help go unanswered, and a client ask her point blank, "Am I gonna die today?" That first shift as a professional caregiver didn't just break Nicole Becerra's heart. It gave her a mission. Instead of accepting that this was just how senior care worked, she asked a different question: what if it didn't have to be this way? In this episode, Nicole shares how she went from sitting bedside with dementia patients to acquiring raw land, navigating septic and zoning laws, and securing an SBA loan to build Mosaic Memory Care, a 16 room luxury memory care mansion in the Texas Hill Country. She breaks down what it actually took to move from caregiver to developer with zero real estate background: interviewing contractors until she found ones who would explain things in plain language, commissioning third party feasibility studies for her bank, and financing the entire project herself and her husband rather than bringing on outside investors. She also opens up about Builders of Care, the nonprofit she founded to help families afford quality senior care and to help other small operators get the capital they need to build homes like hers. This episode is for real estate investors looking at senior housing and memory care as an emerging niche, anyone weighing land development for the first time, and listeners who have watched a parent or grandparent struggle to get real dignity in a care facility. With an aging population and booming Hill Country demographics, Nicole makes the case that small, intimate memory care homes are one of the most overlooked and needed opportunities in real estate right now. 5 Powerful Takeaways Learn how to structure a memory care real estate deal from raw land purchase through SBA financing, including how a land loan gets wrapped into a construction loan. Discover why septic and zoning rules can dictate your entire site plan, and how Nicole turned a 14 acre parcel into two 16 room luxury homes with room for walking paths and a courtyard. Get a real playbook for building trust with contractors and city officials as a newcomer, including the exact question to ask when you're in over your head. Understand how a nonprofit arm like Builders of Care can create scholarships and grants that make quality senior care and small operator development more financially accessible. Hear why financing a project entirely with personal savings and a bank loan, without outside investors, can be a deliberate strategy for proving a concept before scaling. 00:00 Show Intro 01:00 Cash on Cash Return 03:24 Meet Nicole Becerra 05:23 Caregiving Wake Up Call 09:32 Luxury Memory Care 11:31 Builders of Care Nonprofit 12:40 Land and Zoning Hurdles 16:57 Designing the Neighborhood 19:08 Mosaic Name Meaning 20:14 Newbie Advantage 21:31 Contractors and Communication 22:43 SBA Loan Process 24:12 Funding the Build 25:23 Control Over Investors 27:06 Builders of Care Mission 28:46 Timeline and Next Steps 31:06 Being Mortal Insights 34:26 Advice and Action 35:53 Drive and Aspirations 39:08 Systems and Delegation 40:53 Success and Where to Find Nicole 42:31 Final Thanks and Sign-Off About the Guest Nicole Becerra spent years as a frontline professional caregiver before deciding the industry needed to be rebuilt from the ground up. She taught herself land acquisition, entitlement, financing, and new construction with no prior real estate background and is now developing Mosaic Memory Care, a luxury memory care community in the Texas Hill Country. She is also the founder of Builders of Care, a nonprofit that provides scholarships to families who need senior care and capital support to small operators building their own care homes. Nicole is currently finalizing her SBA loan and permitting, with construction expected to begin this fall. Resources & Websites Mentioned buildersofcare.org Instagram: @caringwithnicole 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 New episodes drop every Monday at 6am EST. See you next time.

  5. Jul 6

    311 - Why This Investor Ditched Multifamily for Hot Springs and National Parks

    What if the smartest move in real estate right now isn't multifamily at all? While thousands of investors keep fighting over the same overpriced apartment deals, Zander Kemp walked away from 23 apartment buildings to chase something almost nobody else was building: luxury glamping and hot spring resorts parked right outside America's busiest national parks. In this episode, Zander, founder of Clear Summit Investments, breaks down exactly how he identified outdoor hospitality as a massively underpriced niche, still 90% owned by mom and pop operators, trading at cap rates nearly double what multifamily and self storage command. He walks through his entire investment thesis: why proximity to growing metro areas and capped national park visitation numbers create built in demand, how amenities like cold plunges and hot tubs drive outsized returns per unit, and how his Real Freedom Income Fund structures investor returns across three distinct paths, from 10% monthly cash flow to 14% compounded over three years. He also gets refreshingly specific about deal sourcing, the "work camper" staffing model that keeps his resorts running lean, and the exact criteria his team uses to evaluate a property before writing an offer. This episode is essential listening for accredited investors tired of razor thin multifamily margins and looking for a niche with real pricing power, and for anyone curious how a former military officer turned house flipper built a five resort portfolio averaging 24% annual returns. If you have ever wondered whether there is a smarter way to invest passively while still getting to enjoy what you own, this conversation lays out the blueprint. 5 Powerful Takeaways Discover why outdoor hospitality assets are trading at nearly double the cap rate of multifamily and self storage, and what that spread means for investor returns. Learn the exact location criteria Clear Summit uses before buying a resort, including proximity to national parks and growing metro job markets. Understand how strategic amenities like cold plunges and communal hot tubs can dramatically boost revenue per unit without ballooning costs. Get a clear breakdown of the three investment paths in the Real Freedom Income Fund and how to choose the right one for your cash flow goals. Hear how the "work camper" staffing model solves the on-site management problem for remote hospitality properties at a fraction of traditional labor costs. 00:00 Welcome to REIGN 00:53 Tax Lien Basics 03:26 Meet Zander Kemp 05:14 From Military to Multifamily 07:39 Why Outdoor Hospitality 11:02 Shifting in Tough Markets 13:54 National Parks Strategy 17:01 Resorts vs Short Term Rentals 18:11 Amenities and Day Passes 19:19 Investor Returns and Deal Criteria 22:53 Investor Paths Explained 24:27 Security and Redemption Terms 25:02 Resort Perks and Stays 27:01 Inside the Properties 28:44 Food Beverage Add Ons 29:28 On Site Staffing Model 31:34 Accredited Investor Rules 31:56 Clear Summit Growth Plans 33:01 How to Invest Now 34:13 Dogs and Dog Parks 34:58 Badass Book Mindset 36:24 Advice Focus and Drive 38:36 Goals Systems and Success 41:20 Closing and Subscribe About the Guest Zander Kemp is the founder of Clear Summit Investments, where he helps accredited investors build passive wealth through luxury RV and glamping resorts situated near America's national parks. Over nine years in real estate, he has completed 55 deals and worked with roughly 150 investors, scaling from single-family turnkey rentals to 23 apartment buildings before pivoting entirely into outdoor hospitality. He has since grown Clear Summit to five resorts across the Rocky Mountain region, delivering investors an average 24% annual return. Zander's background spans military service, high-rise and industrial development, and hands-on distressed multifamily renovation, giving him a rare, full-spectrum view of real estate investing. He now leads the Real Freedom Income Fund, built around the same freedom-focused philosophy that drives his own life between Hawaii's North Shore and the mountains he loves to climb. Resources & Websites Mentioned Clear Summit Investments: https://www.clearsummitinvestments.com Zander Kemp on LinkedIn Jen Josey: https://www.therealjenjosey.com/ REIGN Mastermind: https://www.reignmastermind.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 New episodes drop every Monday Morning at 6am EST. See you next time.

  6. Jun 29

    310 - The Pilot's Checklist That Built a $1 Billion Self Storage Empire

    310 - From Airline Pilot to $1 Billion Self Storage Empire: Ryan Gibson's Blueprint for Passive Wealth What if the same checklist that keeps a commercial jet from crashing could also keep your real estate deals from blowing up your bank account? That is the mindset Ryan Gibson brought from the cockpit to the boardroom, and it is the difference between investors who build lasting wealth and those who get burned chasing the next shiny deal. In this episode, Ryan, president of Spartan Investment Group and co-host of Passive Income Pilots, breaks down the go or no-go framework he uses to evaluate every deal, the same discipline that keeps an airplane in the sky. He shares the 10/30/30/30 principle for structuring your net worth, explains why self-storage has outperformed every other asset class over the last 40 years at roughly 17 percent annually, and reveals how Spartan grew from a single house flip with his neighbor turned business partner into a billion-dollar portfolio spanning 15 states and over seven million square feet. He also gets into the strategy behind converting old retail boxes, including a former Kmart and Macy's, into thriving storage facilities, plus the surprising real-world hazards that come with owning thousands of storage units. This episode is essential listening for high-income professionals, especially airline pilots, who want true passive income without taking on a second job, as well as any real estate investor looking to diversify into a historically high-performing, recession-resistant asset class. If you have ever wondered how to evaluate a deal with the same clarity a pilot uses before takeoff, or whether self-storage deserves a spot in your portfolio, this conversation will change how you think about both. 5 Powerful Takeaways Learn the "extension clause" negotiating trick for 1031 exchanges that buys you extra time on the 45 and 180-day deadlines so you are never forced into a rushed, overpriced purchase. Discover the go/no go decision framework, borrowed directly from cockpit protocol, for knowing exactly when to walk away from a real estate deal and when you are too committed to turn back. Get the 10/30/30/30 net worth allocation strategy high-income earners use to balance liquidity, market growth, tax-advantaged real estate, and truly passive investments. Understand why self-storage has delivered roughly 17 percent average annual returns over 40 years, outperforming multifamily, data centers, and mobile home parks. Hear how a single house flip with a neighbor turned into a billion-dollar, 15-state self-storage portfolio, and what that growth story reveals about building investor trust early. 00:00 Show Intro 00:59 1031 Exchange Basics 03:22 Meet Ryan Gibson 04:51 1031 Exchange Pro Tip 07:00 From Pilot to Investor 11:32 Finding a Business Partner 13:55 Pilot Mindset for Deals 20:01 Leading Under Pressure 22:20 Passive Income Explained 24:12 10 30 30 30 Portfolio 28:33 1031 Legacy Planning 29:51 Why Self Storage Wins 33:00 Market Consolidation Play 36:14 Conversions and Reuse 37:32 Tax Foreclosure Surprises 40:34 Spartan Growth Plans 41:16 Wild Storage Stories 43:30 Badass Rapid Fire 48:34 Success Definition and Wrap About the Guest Ryan Gibson is a commercial airline pilot turned self-storage entrepreneur and president of Spartan Investment Group, now the 29th largest self-storage operator in the country with more than one billion dollars in capital organized across 15 states and over seven million square feet. He built Spartan alongside business partner and Army veteran Scott Lewis, growing the company from a single neighborhood flip into a major institutional-grade platform. Ryan also co-hosts the podcast Passive Income Pilots, where he teaches airline pilots and other high-income professionals how to build genuine passive income without adding a second job to their schedule. He applies the same disciplined, checklist-driven decision-making from his years in the cockpit to how he vets deals, operators, and markets today. More than 400 airline pilots have invested alongside him in Spartan's self-storage portfolio. Resources & Websites Mentioned https://spartan-investors.com ryan@spartan-investors.com Passive Income Pilots podcast (available on iTunes, Stitcher, and YouTube) 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 New episodes drop every Monday Morning at 6am EST. See you next time.

  7. Jun 22

    309 - From Addiction Recovery to 1,100 Lots: The Mobile Home Park Strategy Nobody Talks About with Tim Woodbridge

    309 - From $250K to $570K in 14 Months: How Tim Woodbridge Built a Mobile Home Park Empire Through Recovery and Resilience What if the deal everyone told you was bad turned out to be the foundation of an 1,100 lot portfolio? Tim Woodbridge bought his first mobile home park for $250,000 in 2019 with only 10 of 36 lots occupied. Experienced investors told him to walk away. Fourteen months later, after bringing in new homes and raising occupancy, that same property appraised for $570,000 and he returned every dollar of investor capital through a refinance. This episode is proof that your first deal does not have to be perfect to change the trajectory of your life. Tim is the founder and acquisitions lead at WCG Investments, where he and his two partners now manage roughly 25 mobile home parks and more than 1,100 lots across the southeast. He breaks down exactly how mobile home park investing works, including the hybrid ownership model his company uses to balance investor returns with affordable housing for tenants, and why he targets a 16 to 20 percent IRR that roughly doubles investor capital over five to seven years. He also opens up about being in long-term recovery from drugs and alcohol and living with multiple sclerosis, and how both experiences shaped a leadership philosophy built on meeting people exactly where they are. This episode is for accredited investors looking for a recession-resistant alternative to apartments and single-family rentals, for anyone curious about how mobile home parks actually generate returns, and for investors who need permission to stop waiting for the perfect deal and start taking action. If you have ever felt stuck in analysis paralysis, Tim's story is the push you need to hear today. 5 Powerful Takeaways How Tim turned a $250,000 mobile home park with 26 empty lots into a $570,000 asset in just 14 months by financing new homes through a manufacturer infill program during COVID Why chasing a "perfect" deal kept other investors on the sidelines while Tim built a portfolio that now spans 25 parks and over 1,100 lots The hybrid ownership model WCG Investments uses to balance park-owned homes, rent-to-own homes, and tenant-owned homes, so they never overpay for a single rigid strategy What accredited investors can actually expect to earn with a $50,000 minimum investment, including monthly distributions and a target of doubling their capital within five to seven years How Tim's long-term recovery from addiction and his multiple sclerosis diagnosis reshaped his approach to leadership, partnerships, and treating every tenant and investor like a human being first 00:00 Show Intro 00:40 Badassery Bestowment 01:01 First Deal Mindset 03:11 Meet Tim Woodbridge 04:35 Recovery and MS 09:04 Serving Residents 10:19 First Park Breakdown 14:56 Hybrid Ownership Models 16:54 Depreciation Myth 18:26 Risks and Resilience 20:03 Affordable Housing Shift 21:09 Tenants vs Investors 21:35 Recession Resistant Strategy 23:19 Investor Terms Explained 24:12 Returns Example Breakdown 25:38 Meet WCG Investments 26:30 Scaling Base Hits 28:21 Badass Books Advice 29:42 Drive Goals Systems 34:13 Partnership Tips 35:40 Defining Success Wrap   About the Guest Tim Woodbridge is the founder and acquisitions lead at WCG Investments, where he helps accredited investors build recession-resistant portfolios through mobile home park investing. He purchased his first park in December 2019 for $250,000 and doubled its value within 14 months through a strategic refinance. Today, he and his partners manage roughly 25 parks and more than 1,100 lots across the southeastern United States. A retired nurse, Tim is in long-term recovery from drugs and alcohol and lives with multiple sclerosis, experiences that shape a people-first approach to both his tenants and his investors. He is currently working toward $250 million in assets under management by 2029 and is driven by a long-term goal to help end homelessness in the United States by 2050. Resources & Websites Mentioned WCG Investments: https://wcginvestments.com Mobile Home Park Store: mobilehomeparkstore.com 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 New episodes drop every Monday Morning at 6am EST. See you next time.

  8. Jun 15

    308 - He Lost 6 Figures as an LP and Then Became the Guy Who Vets the Operators

    308 - From 52 Houses to Fund Manager: How Tom St. John Built a Portfolio Powered by Discipline, Loss, and Unshakeable Due Diligence What happens when a single telescope changes everything? For Tom St. John, watching his father retire after 32 years at a power plant with nothing but a telescope as a gift was the moment that cracked his world open. That telescope became a symbol of what following the rules without building real assets actually gets you. Tom made a vow to find another way, and what followed was a decades-long journey through single-family rentals, multifamily acquisitions, devastating loss, and hard-won wisdom that now fuels NorthCorp Capital, his private capital allocator and fund management firm based in Toledo, Ohio. Tom's story is not a highlight reel. He built a portfolio of 52 single-family homes, auctioned off nine of them at minimum bids just to scrape together a down payment on his first multifamily deal, and then lost his brother and maintenance manager in a tragic car accident that forced him to run everything alone for six years. He later lost six figures as a limited partner by trusting the wrong operator, and that painful lesson transformed him into one of the sharpest due diligence practitioners in the private markets space. Today, Tom vets operators for a living, manages funds across multifamily, real estate debt, and private credit, and delivers annualized returns of 12% to accredited investors who want the economic benefits of real estate without the operational headaches. If you are a real estate investor wondering whether to stay in the grind of active operations or start thinking about passive investing and private alternatives, this episode will shift how you see both. Tom breaks down exactly how he stress-tests deals, what operator red flags look like in the wild, how to increase net operating income by improving tenant experience, and why significance matters more to him than success. Whether you are just starting out or ready to level up into multifamily or fund investing, you will walk away with a smarter framework and a deeper sense of what building a lasting portfolio actually requires. 5 Powerful Takeaways Auctioning nine houses to fund his first multifamily deal taught Tom that letting go of smaller assets strategically is often the fastest path to real scale, and that conviction in the right next move matters more than comfort. After losing six figures to the wrong operator, Tom learned to invest in people first and deals second, focusing on track record through difficult markets, conservative underwriting, and whether operators earn based on performance rather than fees. Increasing net operating income does not start with jacking up rents. It starts with building community, improving tenant experience, and making residents want to stay, because one lease renewal is worth far more than a $100 rent bump. High-pressure sales tactics from operators ("We're 85% subscribed, invest now!") are a major red flag that signals someone is in the business of raising money, not managing property. Tom's shift from pursuing growth and net worth to pursuing income replacement and significance is a mindset upgrade that every investor scaling toward time freedom needs to hear. About the Guest Tom St. John is the founder of NorthCorp Capital LLC, a private capital allocator and fund management firm based in Toledo, Ohio, with over 20 years of experience in real estate and private markets. Tom began his real estate journey in 2005 after watching his father retire from 32 years at a power plant with almost nothing to show for it, which set him on a relentless path toward financial independence. He built a 52-unit single-family portfolio, transitioned into multifamily, and navigated serious personal losses including the death of his brother and a six-figure loss as a limited partner, each of which sharpened his operational and due diligence skills. Today Tom manages funds across multifamily syndications, real estate debt, and private credit, helping accredited investors access vetted operators and stable income streams. He is known for his thorough stress-testing of deals, his deep operator relationships, and his conviction that significance is a more meaningful measure of success than net worth. 00:00 REIGN Podcast Intro 00:53 BRRRR Method Breakdown 02:51 Meet Tom St John 04:41 Telescope Turning Point 07:32 Learning Through Books 09:26 First Rental Deal 10:05 Scaling Single Family Ops 12:40 Auction to Go Multifamily 14:21 Why Multifamily Scales 16:52 From Operator to Investor 18:09 Boosting NOI With Amenities 21:19 Vetting Operators as LP 23:41 Losing His Brother and Rebuilding 26:29 Vetting Operators 27:57 Underwriting Stress Tests 29:16 Red Flags and Trust 31:04 NorthCorp Capital Today 34:13 Fund Structure Explained 35:38 Podcast and Guests 38:06 Badass Framework 38:12 Books and Advice 41:21 Drive Goals Systems 44:58 Significance and Wrap Up   Resources & Websites Mentioned NorthCorp Capital: https://northcorpcapital.com Tom St. John on LinkedIn: search Thomas St. John Book recommendation: "Parable of the Pipeline" by Burke Hedges Book mentioned: "Who Not How" Book mentioned: "Buy Back Your Time" by Dan Martell Book mentioned: "Rich Dad Poor Dad" TriVest (investor portal and fund administration platform) 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 New episodes drop every Monday Morning at 6am EST. See you next time.

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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
    315
  • Rating
    Explicit
  • Copyright
    © REI Growth Network LLC
  • Show Website
    Comfort To Courage

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