Podcast
The Hustle Harder Show
Hosted by James Gaskin · EN
If you’re a veteran real estate investor, just starting your journey as a real estate pro, or simply fascinated by the entrepreneurial spirit then this podcast is for you.
This is the Hustle Harder Real Estate Podcast hosted by James Gaskin and powered by Renovo Financial.
As a lender to real estate investors since 2011, we’ve had the honor of helping thousands of talented real estate entrepreneurs build their dream life one 2x4 at a time – this podcast is about them.
We believe that real estate investing is a hyper-local business, so we’ll leverage our network of local branch offices across the country to interview local investors and other rockstar real estate professionals. We’ll go behind the curtain to uncover the “why” that fuels them to hustle harder than the rest and learn what drives them to succeed and win against the odds in the market they call home.
James Gaskin is an executive with Renovo Financial and has spent the last 10+ years helping build real estate lending companies to support local investors. At Renovo James focuses on growth strategy, sales talent acquisition, business development, and culture building.
Renovo Financial is a leading lender for professional real estate investors. Our local branch offices across the US are led by experienced lending experts who provide our clients with tailored lending solutions using deep local knowledge and an elite network that professional investors count on to help push their businesses forward in all market conditions.
Join us as we look beyond the sticks and bricks to get to know guests on a deeper level, and hopefully pull out some lessons and concepts that can help you on your journey to building a life of financial freedom using the incredible vehicle of real estate.
18episodes
Episodes
Newest firstAll episodes
Hometown Series Episode #2 - Brandon Moulton
2w ago00:33:58Tap to summarizeIn this episode of Hustle Harder, James and Abbey sit down with Brandon Moulton, one of Renovo’s top multifamily lenders, to discuss his path from Toledo, Ohio to becoming a nationally recognized originator in real estate finance. Brandon shares how early experiences in development and banking shaped his career, why he transitioned into private lending, and what has kept him at Renovo for more than a decade. The conversation explores the current state of Chicago multifamily investing, the importance of focus and repeatable business plans, building strong borrower relationships, and the evolution of Renovo’s culture over the years. Along the way, the crew dives into family life, moving to St. Louis, favorite Midwest food stops, old Renovo stories, and plenty of laughs.Key Points from This Episode00:00 – Welcome back to the Hustle Harder Show from downtown Chicago00:44 – Brandon’s background growing up in Toledo, Ohio01:57 – Early exposure to development work and discovering real estate03:22 – Transitioning from traditional banking into private lending04:19 – Brandon’s 2024 production numbers and multifamily lending focus05:14 – Moving from Chicago to St. Louis and balancing both markets07:01 – Parenting life with two young boys and family routines08:13 – The legendary Wally’s gas station discussion09:36 – Reflecting on Renovo’s early startup culture and hustle mentality12:06 – Memorable moments from Brandon’s first days at Renovo14:25 – The craziest site visit story from Brandon’s lending career15:15 – Building and managing Brandon’s six-person lending team18:05 – Brandon’s most overused phrases and pipeline meeting habits19:05 – The current state of Chicago’s multifamily market20:44 – The biggest challenges facing investors today20:52 – Why focus is the defining trait of successful operators22:03 – How Renovo supports repeatable business plans and experienced borrowers24:13 – Strategic introductions, contractor relationships, and tax incentives25:18 – Cubs vs. Cardinals and life between Chicago and St. Louis26:50 – Books, routines, workouts, and balancing work with family life29:03 – Debating who would win a foot race: Brandon or Eric Workman30:31 – Chicago food takes, favorite snacks, and movie theater traditions32:42 – Final thoughts and episode wrap-upLinksRenovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/ Abbey Hearn on LinkedIn - https://www.linkedin.com/in/abbey-hearn-37aa7526Brandon Moutlon on LinkedIn - https://www.linkedin.com/in/brandon-moulton-7447519
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Hometown Series Episode #1 - Eric Workman
4w ago00:43:53Tap to summarizeIn the first installment of the Hometown Hustle series, James Gaskin and co-host Abbey Hearn sit down with Eric Workman, one of Renovo’s most tenured originators. Eric shares his journey from working in construction to becoming a top-producing lender, while helping his team approach $1B in originations.The conversation dives into what makes the Chicago real estate market unique, why it’s often misunderstood, and how consistency, relationships, and local expertise have fueled Eric’s success. The episode also explores team building, company growth, and what it takes to scale in a competitive lending environment—all with a dose of personality and rapid-fire fun.What You’ll Learn:Chicago is a highly resilient and often misunderstood real estate market.Success in lending comes from consistency, reliability, and strong relationships.Building a dedicated, in-house team improves both efficiency and client experience.In-person collaboration accelerates growth, training, and problem-solving.The best clients are long-term, professional investors seeking true partnerships.Local market expertise provides a major competitive advantage.Timestamps:0:00 – Introduction to the Hometown Hustle series and Eric Workman2:05 – Eric’s background and entry into real estate3:31 – Early days at Renovo and company evolution5:03 – Approaching $1B in loan originations6:40 – Building and structuring a high-performing team8:51 – Delivering consistent customer experience and borrower loyalty10:50 – Importance of in-person collaboration and team culture13:15 – Scaling production and training new talent15:55 – Chicago real estate market insights and trends19:32 – Challenges and complexity of investing in Chicago22:30 – Building a client base of professional investors24:30 – Value of expertise and local market knowledge26:05 – Transition from operator to lender27:19 – Early exposure to real estate and career path31:49 – Advice to younger self and betting on yourself32:57 – Favorite Chicago neighborhoods and lifestyle insights34:07 – Chicago food debate: pizza, hot dogs, and more36:18 – Personal interests: bourbon, music, and podcasts39:50 – Rapid-fire questions: movies, food, and fun facts42:03 – Closing thoughts and series wrap-upLinksRenovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/ Abbey Hearn on LinkedIn - https://www.linkedin.com/in/abbey-hearn-37aa7526 Eric Workman on LinkedIn - https://www.linkedin.com/in/eric-workman-1681996
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From Carpenter to Community Builder: Dajuan Robinson’s Real Estate Journey
Apr 2301:02:26Tap to summarizeIn this episode of The Hustle Harder Show, host James Gaskin sits down with Dajuan Robinson, a Chicago-based general contractor, real estate investor, and mentor. Dajuan shares how he went from learning carpentry at a young age to building a thriving real estate business and leading impactful community development projects.He breaks down the lessons learned from early mistakes, navigating predatory lending, and how partnerships—especially with the Cook County Land Bank and Renovo’s C3 program—helped scale his work. Dajuan also dives into his passion for mentorship, creating educational cohorts to help aspiring developers avoid costly pitfalls and build sustainable success.What You’ll Learn:Start where you are—hands-on skills can evolve into full-scale investing.Mistakes are part of the process, but persistence is what creates success.Access to capital and the right partnerships are critical to scaling.Community-focused development creates long-term impact beyond profit.Mentorship can save time, money, and costly errors.Real estate success requires discipline, sacrifice, and consistency.Timestamps:0:00 – Show intro and guest introduction1:02 – Dajuan’s background and multiple roles2:02 – Growing up in Chicago and early ambitions4:43 – Introduction to carpentry through family and school6:23 – Building a client base before graduating high school10:03 – Leaving a stable job to pursue entrepreneurship11:06 – First real estate deal and partnership13:09 – Scaling early investments and learning financing14:32 – Challenges with predatory lenders15:21 – Cook County Land Bank explained20:40 – Transition into new construction projects24:32 – Meeting Tiffany Taylor and entering C3/Renovo ecosystem26:42 – Securing funding and scaling developments29:08 – First new construction success and community impact31:32 – Economic and neighborhood impact of development33:35 – Becoming a mentor and launching education programs34:21 – “Real & Rehab” mentorship program creation36:12 – Building a full real estate course41:20 – Cohort structure and learning experience43:18 – Hands-on site visits and real-world training48:12 – Who the program is for52:31 – The reality of real estate commitment54:21 – Portfolio growth and scaling55:24 – Advice on mentorship and avoiding losses56:46 – Long-term vision: helping others succeedLinksRenovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/
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The Financial Blueprint for Real Estate Entrepreneurs
Mar 2501:17:40Tap to summarizeIn this episode of Hustle Harder, James sits down with Marcus Crigler, Founder of BEC CFO & CPA, to break down what truly separates real estate operators who build lasting wealth from those stuck in the hustle cycle. Marcus shares his journey into real estate-focused accounting, explains why most investors struggle with the “language of business,” and outlines a practical framework for moving from hustle to security, expansion, and ultimately investment-driven freedom. The conversation dives into financial discipline, reserves, hiring strategy, key ratios, market shifts, and advanced tax strategy—offering a blueprint for building a resilient, scalable real estate business in an “earn it” market. Key Points from This Episode 00:00 – Welcome to the Hustle Harder Show and introduction 00:24 – Introducing Marcus Crigler, fractional CFO for real estate investors 02:26 – Marcus’ origin story and how 2008 shaped his career path 05:44 – The meaning behind “Beck” and building a business around family 07:59 – Why most real estate investors struggle with financial sophistication 12:29 – The hidden cost of ignoring bookkeeping and financial structure 17:19 – The evolution from DIY bookkeeping to full financial back-office support 21:44 – Why growing businesses need more than a shoebox of receipts 27:12 – The four phases of every entrepreneur: Hustle → Secure → Expand → Invest 30:52 – The danger of expanding before securing reserves 33:46 – Growing expenses with reserves instead of revenue 37:18 – The impact of 2022–2023 growth and 2025 margin compression 42:04 – Why today’s market rewards disciplined operators 45:50 – Sharpening strategy and adapting to shifting buyer demand 50:22 – Competing by differentiating product in an “earn it” market 56:13 – The core financial ratios every real estate operator should track 59:40 – Running a 30% margin business: marketing, human capital, and G&A 01:01:32 – Cash flow timing, liquidity, and managing construction draws 01:07:20 – Tax strategy, marginal rates, and why deductions matter more at scale 01:11:44 – Leveraging real estate for tax efficiency through bonus depreciation 01:13:01 – Real-world client examples of improving liquidity and tax positioning Links Renovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/ Marcus Crigler on LinkedIn - https://www.linkedin.com/in/marcus-crigler-cpa-977a45b7 BEC CFO & CPA - https://beccfo.com/
Transcribe →Adventures in Land Development
Mar 401:03:25Tap to summarizeIn this episode of Hustle Harder, James sits down with John Curry, Co-Founder and CEO of Sétanta Development Capital, to break down the misunderstood world of land acquisition and development (A&D) lending. John shares his journey from Irish lawyer to U.S. real estate investor, explains why land earned its “toxic” reputation after the GFC, and walks through how modern land development actually works. The conversation covers risk, entitlement challenges, public builders going land-light, private credit replacing banks, and why land remains a critical “widget” in solving the housing shortage. Key Points from This Episode 00:00 – Welcome to the Hustle Harder Show and introduction of guest John Curry 01:09 – John’s background, move from Ireland, and entry into A&D investing 02:39 – Founding Sétanta and closing the firm’s first loan 03:04 – The origin and meaning of the name Sétanta05:22 – What Sétanta does and how land lending differs from construction lending 07:34 – How land development works from raw land to buildable lots 10:48 – Why builders stopped self-developing land post-GFC 12:51 – Public markets, land-light strategies, and risk perception 14:32 – Why land became a “four-letter word” after the GFC 20:49 – How forced selling distorted land values and wiped out developers 23:35 – Sétanta’s borrower-first philosophy and partnership mindset 24:42 – COVID-era deal challenges and honoring commitments 29:23 – How the land business has evolved since the GFC 31:29 – Land scarcity, entitlement challenges, and affordability pressures 35:01 – Opportunity created by a shortage of land developers 38:02 – Builder takeouts, deposits, and reduced speculation 41:10 – Sétanta’s leverage model and long-term developer relationships 43:48 – The retreat of banks and rise of private credit in land lending 47:32 – Experience, cycles, and why focus matters in A&D lending 50:15 – “Developers who lend” and managing execution risk 52:36 – Strategic alignment between Sétanta and Renovo 56:24 – Shared values, Victory Park connection, and partnership outlook 59:13 – Final thoughts and closing remarks Links Renovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/ John Curry on LinkedIn - https://www.linkedin.com/in/johnfcurry Sétanta - https://setantadc.com/
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2026 - 2025 Review & New Year Kickoff
Jan 2801:09:47Tap to summarizeJames Gaskin kicks off Season 3 with a deep dive into the major themes that shaped real estate lending in 2025 — and what's ahead for 2026. From market trends and fraud risk to AI adoption and the war for talent, James offers a candid, insightful look at the state of the industry. This solo episode is packed with hard-earned wisdom for both real estate investors and lenders navigating an uncertain, competitive environment.Key Points from This Episode3:08 – Welcome to Season 3: New energy, evolving content, and a look back at 20257:23 – Recapping 2025: Intense competition, rate compression, and investor capital influx12:56 – Fraud & valuation issues: Major incidents spark industry-wide reassessment19:38 – Market volatility: Inventory buildups in Texas, Florida, and the Carolinas24:58 – Tariffs & immigration: Anticipated impacts on materials and labor that didn’t fully materialize29:28 – The rise of AI: Opportunity for efficiency, but also new risks — especially in fraud35:18 – Increased scrutiny from loan buyers: Discipline and underwriting standards on the rise39:53 – 2026 forecast: Expect continued volatility and political intensity43:23 – Talent wars: High switching costs, but strong lenders have an edge48:08 – AI in 2026: More use cases, more fraud threats, and the need for balance52:23 – “Higher for longer” interest rates: The market vs. Fed intentions56:18 – Trump-era housing policies: Hedge fund bans & affordability narratives59:38 – Fortifying capital structures: Why redundancy and liquidity are crucial1:03:13 – Hyper-local insights: The importance of boots on the ground & relationships1:05:23 – The need for industry self-regulation: Avoiding government intervention1:07:38 – Smarter investing in 2026: Discipline, stress-testing, and capital reserves1:10:38 – Over-leveraging & the hidden danger of 100% financing1:12:18 – Final thoughts: The power of “no,” picking the right partners, and planning for volatilityLinksRenovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/
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California Dream'n with Andy Pollock
Nov 1901:10:43Tap to summarizeIn this episode of the Hustle Harder Show, host James Gaskin sits down with Andy Pollock, the veteran lending leader spearheading Renovo Financial’s California expansion. With nearly 40 years in the industry, Andy shares invaluable lessons from his career, his passion for building teams, and the mission of bringing Renovo’s unique people-first, locally driven model to the West Coast. Key Points from This Episode 00:00 – Introduction: Hustle Harder in San Francisco 01:30 – Meet Andy Pollock: Lending legend with 40 years of experience 02:20 – Andy’s start in lending and learning through mistakes 04:40 – Climbing to CEO—and why he prefers being #2 06:40 – What keeps Andy hungry after all these years 08:00 – Why humility and sincerity matter at Renovo 11:50 – California expansion: vision, products, and Renovo’s edge 14:25 – What “decentralized” really means 18:00 – Building trust in a mature, competitive market 20:47 – The five-market California blueprint 23:22 – Respect for real estate entrepreneurs and the value of perseverance 27:16 – Why California is key to Renovo’s national ambitions 31:58 – What kind of leaders Renovo California needs 36:02 – Building something from scratch vs. fixing what’s broken 39:43 – The challenge of recruiting great talent—and the upside 44:09 – Why now is the moment for first movers 50:39 – “Powered by Renovo”: What it really means 52:16 – The importance of culture and the Renovo flywheel 59:38 – The opportunity for growth in a highly competitive landscape 1:01:41 – RenovoPalooza, longevity, and being part of something bigger 1:07:48 – Final thoughts: A legacy worth building Links Renovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/ Andrew Pollock on Linkedin - https://www.linkedin.com/in/andrew-pollock-4b46825
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From Military Service to Real Estate with Purpose, with Devin Ramos
Nov 501:00:48Tap to summarizeIn this powerful and inspiring episode, Devin Ramos shares his journey from a 15-year career in the military—including time as a Green Beret—to becoming a full-time real estate investor and co-founder of a growing residential cleaning business, Maid in America. Devin opens up about the internal shift that led him from military service to entrepreneurship, the trials of his first BRRRR deal, and the lessons learned from scaling both a real estate operation and a service business. He and James explore the overlap between leadership, service, and entrepreneurship—diving into topics like marketing mistakes, building a team, navigating business with your spouse, and what it means to stay focused during uncertain market conditions. This episode is packed with strategy, reflection, and entrepreneurial wisdom from someone who’s been through the trenches—literally and figuratively. What You’ll Learn: How Devin transitioned from a 15-year military career into full-time real estate investing Why a service-first mindset and strong values can drive business success The reality of starting with little capital and scaling through creative deal-making What a “novation” deal is and how it compares to wholesaling and flipping The importance of cashflow and how Devin used a cleaning business to fuel real estate investments Lessons from managing two businesses at once—and how to stay focused without burning out Why discipline, margin, and strategy matter more than volume in today’s market How Devin and his wife grew a residential cleaning company with national potential Timestamps: 0:00 – Introduction0:56 – Devin’s background: Small-town roots, military service, and discovering his desire to serve 5:30 – Entering Special Forces and grappling with career/life purpose 10:40 – A pivotal mindset shift around money, freedom, and retirement 13:10 – Faith, family, and the role of values in business decisions 18:43 – Starting in real estate: Rich Dad Poor Dad, BiggerPockets, and learning by doing 24:29 – From one BRRRR to 40 deals a year: Building the real estate business 27:15 – What’s a "novation" and when does it make sense? 30:32 – Creative problem solving: A multi-family deal using sub-to and wholesaling 34:57 – Balancing two businesses: Real estate and residential cleaning 37:55 – Launching “Maid in America” cleaning company with his wife 42:06 – Scaling the cleaning business while reinvesting in real estate 49:11 – Devin’s current focus: High-margin deals and replicating business units 54:06 – Navigating burnout, risk, and learning to slow down 57:25 – Where to find Devin online and learn about his podcast LinksDevin on LinkedIn - https://www.linkedin.com/in/devin-ramos-602a811abJames Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/ Renovo Financial - https://renovofinancial.com/
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From NFL Dreams to Real Estate Domination: Dean Rogers' Journey of Grit, Growth & Giving Back
Oct 801:24:51Tap to summarizeIn this inspiring episode, James sits down with Dean Rogers—former NFL player turned powerhouse real estate investor and community builder. Dean shares his raw and powerful journey, from living the dream as a San Diego Charger to walking away from football for the sake of his health, to starting from scratch and building a thriving real estate empire in Central California. Dean opens up about hitting rock bottom, losing $187K on a single deal, and the lessons that shaped his comeback. He also discusses the origin and explosive growth of Deal Champs, the community he co-founded to empower investors with collaboration and abundance.Whether you're chasing financial freedom or building something from the ground up, this episode is packed with insights, grit, and motivation.What You’ll Learn:Why Dean walked away from a 3-year NFL contract and the mental toll it tookThe painful reality of transitioning into the corporate world with a $65K salaryHow Dean discovered real estate and landed his first wholesale deal with no moneyLessons from losing six figures in bad deals—and how he bounced backThe birth of Deal Champs and how it grew into a national real estate movementWhy investing in yourself and asking for help can shortcut years of painHow Dean’s family and freedom mindset fuel his hustle every dayTimestamps: 0:00 – Welcome to the show + intro to Dean Rogers 0:44 – Dean's NFL to real estate highlight reel 3:05 – The full story: getting to the NFL the hard way 12:05 – NFL locker room culture & wild competitiveness 22:42 – Why Dean walked away from football at his peak 29:19 – From 7-figure NFL contract to $65K salary in SF 35:46 – Losing $100K in house flips & lessons in grit 43:13 – “Better to do no deal than a bad deal” 46:33 – Gaining skills: sales, accounting, leadership 53:47 – Realizing the power of coaching & mentorship 57:08 – The origin of Friends With Benefits (wholesale model) 1:04:25 – Building Deal Champs and scaling the community 1:11:23 – Dean’s family, his “why,” and a life of freedomLinksRenovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/
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From Firefighter to 70 Units a Year: Josh Swart’s Blueprint for Building Wealth
Jul 1600:59:59Tap to summarizeIn this episode, James sits down with Josh Swart in his Concord, NC studio to unpack his journey from firefighter to full-time real estate investor building and renting 70+ units a year. Josh shares how he went from grunt demo jobs as a teenager to developing subdivisions, the lessons learned from big wins and big losses, and how building the right team changed his business. They dive deep into scaling up, hiring, managing risk, why Josh prefers new builds to flips now, and the mindset shifts needed to go from employee to entrepreneur.Key Points from This Episode00:00 — James welcomes listeners and introduces Josh Swart, recording from Concord, NC.01:01 — Josh explains how he got into investing, starting in 2017, and what his business looks like today (70 units/year).02:58 — Why Josh holds some properties as rentals and how new builds help avoid old-house headaches.04:27 — From working fire department shifts to working construction on his days off — and realizing he was on the wrong side of the equation.05:10 — Scraping together family money for his first flip, making $1,000 — and deciding to bet on himself.07:00 — Josh talks about the uncomfortable personal growth needed to run a business — from hunting deals to building a team.08:51 — How his team grew to 10 people, including virtual staff for admin and bookkeeping.09:40 — Living in a flip, swiping pre-workout from work to stay energized — and how the first real profit opened his eyes.13:20 — Josh’s lightbulb moment — using larger lots and subdivision to unlock value.17:08 — Focusing on Charlotte’s secondary markets, not the city core — and why that works for his strategy.20:19 — The surprises (and headaches) of working with different cities and counties.23:56 — Why Josh prefers to go deeper in his market instead of spreading too thin.24:03 — Building passive income, growing a trusted local brand, and scaling what works.28:21 — Starting with one hire out of necessity, then learning how to delegate and find the right people.30:15 — How Josh learned to give up control — and the freedom that gave him to grow.33:53 — The role of coaching, masterminds, and being held accountable.35:26 — From hiring mistakes to using personality tests and finding the right culture fit (and a shared love of The Office).51:27 — The flips that lost him $150K — and how that refocused him on new builds and predictable returns.56:53 — Beyond the deals, Josh says his biggest win is the people on his team.58:44 — James thanks Josh for sharing openly about the ups and downs, and they wrap up.LinksRenovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/ Josh Swart on LinkedIn - https://www.linkedin.com/in/joshua-swart-699b1b157
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