The Hustle Harder Show

James Gaskin
  • 5.0 (6)
  • Entrepreneurship
  • Updated Monthly

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.

  1. Hometown Series Episode #3 -Brendan Ochinero

    Jun 11

    Hometown Series Episode #3 -Brendan Ochinero

    In this episode of Hustle Harder, James and Abbey sit down with Brendan Ochinero to discuss his journey from growing up in San Diego to becoming one of the top-producing lenders in the country. Brendan shares how an early career in renewable energy land acquisition unexpectedly led him into private lending, the coffee shop conversation that changed everything, and the lessons he learned working every side of the lending business before joining Renovo during the COVID era. The conversation dives into building a high-performing team in Southern California, what gives Renovo an edge in competitive West Coast markets, and why strong borrower relationships matter more than ever in today’s environment. Brendan also opens up about family life as a husband and father of two girls, balancing the intensity of lending with life at home, and what makes San Diego such a unique place to live and work. Along the way, the group talks surf culture, tacos, golf trips, dive bars, Cubs memories, and plenty of California lifestyle stories. Key Points from This Episode 00:00 – Welcome back to the Hustle Harder Show from Chicago 00:56 – Brendan’s San Diego upbringing and early career in renewable energy 02:06 – Learning sales, relationship building, and handling rejection 03:06 – The coffee shop conversation that launched Brendan’s lending career 04:43 – Learning every side of the lending business early on 05:51 – Joining Renovo during the COVID era 06:28 – Brendan’s relationship with Paul Shaughnessy and entering the industry 07:37 – Producing $245M in 2025 and ranking #5 on Scotsman Guide 09:02 – Family life, marriage, and raising two daughters 10:05 – Transitioning from work mode into dad mode 11:37 – Brendan’s morning routine and life with kids and dogs 12:54 – Surf culture and the San Diego lifestyle 14:08 – Building the San Diego Renovo office culture 14:54 – Brendan’s team structure and daily operations 16:19 – What gives their team a competitive edge in California 18:24 – Understanding San Diego real estate pricing dynamics 19:41 – Dream neighborhoods and ideal places to live in San Diego 21:11 – Brendan’s perfect Saturday in Del Mar 22:50 – Best tacos, burritos, and local San Diego food spots 24:41 – Cubs memories, Petco Park, and growing up around Chicago sports culture 26:08 – Childhood hero: Michael Jordan 26:49 – Podcasts, TV shows, and what Brendan is currently watching 28:47 – Favorite golf courses and memorable golf trips 30:51 – Renovo golf competition and team dynamics 32:05 – What top investors are doing differently in today’s market 34:07 – Scottsdale vs. San Diego nightlife debate 35:44 – Favorite dive bars and local hangout spots 37:00 – Final thoughts and episode wrap-up Links Renovo 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 Brendan Ochinero on LinkedIn - https://www.linkedin.com/in/brendanochinero

    38 min
  2. Hometown Series Episode #2 - Brandon Moulton

    May 21

    Hometown Series Episode #2 - Brandon Moulton

    In 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 Episode 00:00 – Welcome back to the Hustle Harder Show from downtown Chicago 00:44 – Brandon’s background growing up in Toledo, Ohio 01:57 – Early exposure to development work and discovering real estate 03:22 – Transitioning from traditional banking into private lending 04:19 – Brandon’s 2024 production numbers and multifamily lending focus 05:14 – Moving from Chicago to St. Louis and balancing both markets 07:01 – Parenting life with two young boys and family routines 08:13 – The legendary Wally’s gas station discussion 09:36 – Reflecting on Renovo’s early startup culture and hustle mentality 12:06 – Memorable moments from Brandon’s first days at Renovo 14:25 – The craziest site visit story from Brandon’s lending career 15:15 – Building and managing Brandon’s six-person lending team 18:05 – Brandon’s most overused phrases and pipeline meeting habits 19:05 – The current state of Chicago’s multifamily market 20:44 – The biggest challenges facing investors today 20:52 – Why focus is the defining trait of successful operators 22:03 – How Renovo supports repeatable business plans and experienced borrowers 24:13 – Strategic introductions, contractor relationships, and tax incentives 25:18 – Cubs vs. Cardinals and life between Chicago and St. Louis 26:50 – Books, routines, workouts, and balancing work with family life 29:03 – Debating who would win a foot race: Brandon or Eric Workman 30:31 – Chicago food takes, favorite snacks, and movie theater traditions 32:42 – Final thoughts and episode wrap-up Links Renovo 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 Brandon Moutlon on LinkedIn - https://www.linkedin.com/in/brandon-moulton-7447519

    34 min
  3. Hometown Series Episode #1 - Eric Workman

    May 7

    Hometown Series Episode #1 - Eric Workman

    In 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 Workman 2:05 – Eric’s background and entry into real estate 3:31 – Early days at Renovo and company evolution 5:03 – Approaching $1B in loan originations 6:40 – Building and structuring a high-performing team 8:51 – Delivering consistent customer experience and borrower loyalty 10:50 – Importance of in-person collaboration and team culture 13:15 – Scaling production and training new talent 15:55 – Chicago real estate market insights and trends 19:32 – Challenges and complexity of investing in Chicago 22:30 – Building a client base of professional investors 24:30 – Value of expertise and local market knowledge 26:05 – Transition from operator to lender 27:19 – Early exposure to real estate and career path 31:49 – Advice to younger self and betting on yourself 32:57 – Favorite Chicago neighborhoods and lifestyle insights 34:07 – Chicago food debate: pizza, hot dogs, and more 36:18 – Personal interests: bourbon, music, and podcasts 39:50 – Rapid-fire questions: movies, food, and fun facts 42:03 – Closing thoughts and series wrap-up Links Renovo 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

    44 min
  4. From Carpenter to Community Builder: Dajuan Robinson’s Real Estate Journey

    Apr 23

    From Carpenter to Community Builder: Dajuan Robinson’s Real Estate Journey

    In 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 introduction 1:02 – Dajuan’s background and multiple roles 2:02 – Growing up in Chicago and early ambitions 4:43 – Introduction to carpentry through family and school 6:23 – Building a client base before graduating high school 10:03 – Leaving a stable job to pursue entrepreneurship 11:06 – First real estate deal and partnership 13:09 – Scaling early investments and learning financing 14:32 – Challenges with predatory lenders 15:21 – Cook County Land Bank explained 20:40 – Transition into new construction projects 24:32 – Meeting Tiffany Taylor and entering C3/Renovo ecosystem 26:42 – Securing funding and scaling developments 29:08 – First new construction success and community impact 31:32 – Economic and neighborhood impact of development 33:35 – Becoming a mentor and launching education programs 34:21 – “Real & Rehab” mentorship program creation 36:12 – Building a full real estate course 41:20 – Cohort structure and learning experience 43:18 – Hands-on site visits and real-world training 48:12 – Who the program is for 52:31 – The reality of real estate commitment 54:21 – Portfolio growth and scaling 55:24 – Advice on mentorship and avoiding losses 56:46 – Long-term vision: helping others succeed Links Renovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/

    1h 2m
  5. The Financial Blueprint for Real Estate Entrepreneurs

    Mar 25

    The Financial Blueprint for Real Estate Entrepreneurs

    In 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/

    1h 18m

  6. Mar 4

    Adventures in Land Development

    In 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 Sétanta 05:22 – 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/

    1h 3m
  7. 2026 - 2025 Review & New Year Kickoff

    Jan 28

    2026 - 2025 Review & New Year Kickoff

    James 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 Episode 3:08 – Welcome to Season 3: New energy, evolving content, and a look back at 2025 7:23 – Recapping 2025: Intense competition, rate compression, and investor capital influx 12:56 – Fraud & valuation issues: Major incidents spark industry-wide reassessment 19:38 – Market volatility: Inventory buildups in Texas, Florida, and the Carolinas 24:58 – Tariffs & immigration: Anticipated impacts on materials and labor that didn’t fully materialize 29:28 – The rise of AI: Opportunity for efficiency, but also new risks — especially in fraud 35:18 – Increased scrutiny from loan buyers: Discipline and underwriting standards on the rise 39:53 – 2026 forecast: Expect continued volatility and political intensity 43:23 – Talent wars: High switching costs, but strong lenders have an edge 48:08 – AI in 2026: More use cases, more fraud threats, and the need for balance 52:23 – “Higher for longer” interest rates: The market vs. Fed intentions 56:18 – Trump-era housing policies: Hedge fund bans & affordability narratives 59:38 – Fortifying capital structures: Why redundancy and liquidity are crucial 1:03:13 – Hyper-local insights: The importance of boots on the ground & relationships 1:05:23 – The need for industry self-regulation: Avoiding government intervention 1:07:38 – Smarter investing in 2026: Discipline, stress-testing, and capital reserves 1:10:38 – Over-leveraging & the hidden danger of 100% financing 1:12:18 – Final thoughts: The power of “no,” picking the right partners, and planning for volatility Links Renovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/

    1h 10m
  8. California Dream'n with Andy Pollock

    11/19/2025

    California Dream'n with Andy Pollock

    In 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

    1h 11m
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Ratings & Reviews

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out of 5
6 Ratings

About

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.

Information

  • Creator
    James Gaskin
  • Years Active
    2024 - 2026
  • Episodes
    25
  • Rating
    Clean
  • Copyright
    © Copyright 2026 James Gaskin
  • Show Website
    The Hustle Harder Show

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