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.
21episodes
Episodes
Newest firstAll episodes
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 16, 202500:59:59Tap 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
Transcribe →Roundtable | Trends, Tribulations, and Independence Day
Jul 2, 202500:45:39Tap to summarizeIn this roundtable, James Gaskin and Kevin Werner unpack the current lending environment and share an insider’s perspective on the real estate private credit market. They discuss trends from the recent National Private Lenders Association (NPLA) conference, the challenges of balancing abundant capital with responsible lending, and the importance of long-term credit discipline. They also touch on the industry’s growing pains, potential risks like fraud, and why a “back to basics” approach matters now more than ever. The episode wraps with a lighthearted look at summer plans and what Independence Day means to the team. Key Points from This Episode00:00 — James and Kevin reconnect after travel breaks and get ready for the 4th of July week.02:25 — Behind the scenes of Renovo’s biggest team event and why culture and awards matter.05:18 — James shares takeaways from the Atlantic City event, including market optimism and broker dynamics.08:14 — Rising institutional capital, credit quality concerns, and how easy money is changing the game.13:40 — Kevin and James break down why some lenders are “gambling” instead of lending.17:34 — How fraud cases can shake investor trust and why self-regulation is critical.23:30 — Why “back to basics” lending is the real edge and lessons from past downturns.35:23 — Why new entrants must build strong foundations and be ready for the next cycle.42:12 — James and Kevin share what Independence Day means to them and their families.44:53 — Staying disciplined, protecting reputations, and a thank you to listeners.LinksRenovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/
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From House Hacking to 1,400 Units: How Mark Ainley Scaled His Real Estate Empire
Jun 17, 202500:59:28Tap to summarizeIn this episode of Hustle Harder, host James Gaskin sits down with real estate investor, property manager, and podcast host Mark Ainley. Mark shares his journey from growing up on the less affluent side of Chicago to building GC Realty & Development, a firm that manages over 1,400 residential units and one million square feet of commercial space. He unpacks his first experience with house hacking, the lessons from early failures, scaling a property management business, and navigating the complexities of investing in Chicago’s real estate market. Mark also dives into how he built a successful turnkey investment business, the challenges of partnerships, transitioning into industrial real estate, and how starting the Straight Up Chicago Investor podcast helped boost his credibility and network. This episode is full of strategic insights, candid stories, and hard-earned lessons for anyone serious about scaling in real estate. Key Points from This Episode [00:00:00] – James introduces the episode and welcomes Mark Ainley [00:01:13] – Mark shares his early life, growing up in Chicago, and his first steps toward real estate [00:02:44] – How limited resources pushed Mark to become financially savvy and discover house hacking [00:05:12] – Mark talks about his first rental gone wrong and the lessons learned from bad tenants and poor screening [00:06:57] – Becoming a licensed agent and earning multiple revenue streams through buying, rehabbing, and selling [00:08:42] – How the property management business accidentally began with a $50/month deal [00:10:50] – The pain and chaos of scaling without processes, and how they eventually implemented structure [00:13:49] – Mark shares the pivotal moment that drove him to formalize operations and improve training [00:15:30] – The journey from flips to BRRRRs and turnkey rentals, and how he built a portfolio of 482 properties [00:20:45] – Why they shifted from residential to suburban industrial investments in 2018 [00:24:10] – Insights into partnership breakups and the importance of clear operating agreements [00:26:20] – Mark reflects on his long-standing relationship with Renovo and working with Eric Workman [00:29:43] – Mark and James discuss the value of relationship-based lending and the importance of being “easy to do business with” [00:33:38] – Why Mark and his co-host started the podcast and how it transformed his brand and reach [00:37:53] – How the podcast drives authority, referrals, and educational content for investors [00:40:41] – How the show helps educate investors on neighborhoods, laws, and best practices in Chicago [00:42:58] – Why in-person interviews lead to better engagement and storytelling [00:44:45] – Mark explains how he learned from others’ mistakes and constantly seeks out growth [00:47:15] – Influential reads, creative strategies, and staying memorable in business Links Renovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/
Transcribe →Roundtable with Brett on the Latest Macro Trends
Jun 5, 202500:45:56Tap to summarizeIn this roundtable edition of The Hustle Harder Show, James Gaskin and Kevin Werner are joined by Brett Sims, Head of Growth at Renovo Financial, for a high-level conversation on economic shifts, capital markets, and strategic growth. The trio dives into policy changes around Fannie & Freddie, inflation data, Fed leadership speculation, bond market concerns, and the importance of discipline amid volatility. Whether you're a seasoned investor or scaling your business, this episode offers tactical insights and measured perspectives to navigate uncertain times. Key Points from This Episode 00:00 – Intro and Brett Sims joins the roundtable 01:29 – Brett’s role at Renovo and where he spends his time 02:27 – Bridging the street and capital markets perspectives 04:13 – Fannie & Freddie privatization back on the table 06:31 – Liquidity concerns and potential impact on interest rates 08:17 – Could Fannie/Freddie fund a US sovereign wealth fund? 10:06 – Moral hazard, underwriting discipline, and housing stability 13:09 – Is now the right time to shake up what’s working? 14:39 – Fed policy, Powell’s job security, and political pressure 16:30 – Shadow Fed president concept and market messaging 18:54 – PCE data, inflation outlook, and Fed strategy21:36 – Jamie Dimon warns of bond market cracks 23:52 – Discipline in the bond market and political consequences 26:00 – Renovo’s culture of discipline and sustainable growth 29:22 – What discipline looks like for real estate investors 32:27 – Expanding with purpose: crawl, walk, run 34:45 – Advice: don’t be brave—be careful, be smart 36:55 – Find mentors, partner wisely, and grow responsibly 39:40 – Admitting what you don’t know and building thoughtfully 40:52 – Brief thoughts on the big budget bill and deficits 42:12 – Foreign investment risk and potential tax changes 44:10 – Rising cost of capital if foreign appetite slows 45:13 – Final thoughts: stay disciplined and stay focused 46:00 – Closing out and looking ahead to the next roundtable Links Renovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/
Transcribe →Empowering Communities Through Real Estate with C3 Impact Fund
Jun 3, 202501:03:21Tap to summarizeIn this episode of Hustle Harder, James sits down with Tiffany Taylor and Aloni Harris to explore the mission-driven work of the C3 Impact Fund, a subsidiary of Renovo Financial and a certified CDFI (Community Development Financial Institution). They share personal stories, the transformative role of C3 in underserved communities, and the ways they’re using real estate to close the wealth gap, create jobs, and revitalize neighborhoods. Key Points from This Episode [00:00:23] – Welcome and introduction to Tiffany and Aloni [00:01:54] – What C3 Impact Fund is and the mission behind the work [00:03:07] – What a CDFI is and why it exists [00:06:06] – C3’s origins and the meaning behind the name [00:07:58] – Lending focus, loan types, and differences from Renovo [00:09:52] – How C3 expands access to capital with flexible underwriting [00:11:22] – Tiffany’s personal story of housing insecurity and community ties [00:17:29] – CRA explained: how banks support C3’s mission through impact investing [00:19:41] – Aloni’s background, identity journey, and introduction to CDFIs [00:26:55] – Launching the Real + Rehab mentorship program [00:28:56] – Educational support, capital access, and building investor pipelines [00:30:56] – Teaching wealth-building strategies post-renovation [00:33:00] – How the Cook County Land Bank helps unlock affordable inventory [00:34:23] – Tiffany’s background in banking and raising capital through CRA [00:38:01] – What banks look for when investing in CDFIs [00:41:01] – C3’s current markets and strategy for expanding nationally [00:44:12] – Aloni’s site visits and local borrower engagement [00:45:39] – Key impact numbers: $70M in originations, 4,000+ jobs, 500+ units [00:47:01] – New construction success story: transforming West Woodlawn [00:50:15] – How these investments set new comps and change neighborhood perception [00:52:44] – What’s next: goals for capital, growth, and investor diversification [00:55:14] – Client story: from taxi fleet to developer through C3 mentorship [01:00:00] – Final reflections and team appreciation [01:01:10] – How to connect with Tiffany and Aloni Links Renovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/
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Navigating Real Estate Trends in 2024 and 2025 with Darren Weaver
Jan 29, 202500:53:41Tap to summarizeIn this episode of the Hustle Harder Show, host James Gaskin welcomes Darren Weaver, Renovo Financial's Chief Credit Officer, to discuss the highs and lows of 2024 and the outlook for 2025 in the real estate market. Darren shares key insights into risk management, credit structuring, and the unique collaboration between lending and credit teams that sets Renovo apart. The conversation covers challenges such as fluctuating interest rates, regional market dynamics, and emerging opportunities for real estate investors. From simplifying strategies to understanding local markets, this episode offers actionable advice for navigating a complex landscape and planning for success in the year aheadKey Points from This Episode[00:00:00] James introduces the episode and guest Darren Weaver, highlighting the theme of reflecting on 2024 and looking ahead to 2025.[00:01:55] Darren introduces himself, his role as Chief Credit Officer, and his focus on managing risk and working closely with Renovo’s lending teams.[00:03:48] The importance of collaboration between credit and sales teams to enhance customer experience and manage risks effectively.[00:06:12] Reflections on 2024: Addressing fluctuating interest rates, the challenges of absorbing increased costs, and rationalizing market conditions.[00:09:43] Shifts in market strategies in 2024, including reduced project sizes and a focus on core competencies.[00:13:17] Discussion on interest rates, differences between short-term and long-term impacts, and why investors must consider broader economic indicators.[00:18:34] Darren emphasizes the importance of picking reliable lending partners who align with client interests for long-term success.[00:26:18] Regional challenges in taxes and insurance in markets like Texas and Florida and their impact on real estate projects.[00:32:40] Market trends in Austin, Florida, and other regions, highlighting opportunities and stress factors for real estate investors.[00:40:23] The supply-demand imbalance in single-family housing and its implications for builders and flippers.[00:45:14] How understanding buyer needs and targeting the right market segment can mitigate risks and increase project success.[00:51:22] Darren shares optimism for 2025, highlighting better predictability in rates and opportunities for value creation in an evolving market.LinksRenovo Financial - https://renovofinancial.com/ James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/ Darren Weaver on LinkedIn - https://www.linkedin.com/in/darren-weaver-20859396
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Building Success in Tampa's Real Estate market with Scott Randall
Nov 15, 202401:29:42Tap to summarizeIn this episode of Hustle Harder, James Gaskin interviews Scott Randall, a real estate investor and builder based in Tampa, Florida. Scott shares his journey from a corporate finance career in Dallas to becoming a successful builder in the Tampa Bay area. He discusses the challenges and triumphs of his first real estate deal, his analytical approach to selecting Tampa, and his experiences in construction and property development. Scott emphasizes the importance of building safe and high-quality homes, understanding local markets, and adapting to changing environments. Key Points from This Episode[00:00:18] Scott Randall's background and introduction[00:05:18] Transitioning into real estate investing[00:08:44] Scott's first real estate deal[00:13:17] The importance of having the right contractors[00:21:02] Early challenges and lessons in construction[00:25:21] Scott's philosophy on building safe and quality homes[00:30:47] Getting a contractor's license and expanding services[00:38:33] Scott's perspective on the Tampa real estate market[00:41:06] Affordability and housing supply issues[00:48:22] The impact of density and smaller dwelling units[00:53:28] Dealing with municipal challenges and infrastructure[01:02:06] Home affordability and the future of real estate[01:06:15] Opportunities in the luxury market[01:15:45] Impact of regulation on real estate development[01:19:38] Balancing growth and sustainability in businessLinks7 PinesScott Randall on LinkedInJames Gaskin on LinkedIn
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Building Renovo's Success: A Journey from the Ground Up with Kevin Werner
Oct 9, 202400:35:49Tap to summarizeIn this debut episode of Hustle Harder, host James Gaskin sits down with Kevin Werner, CEO of Renovo Financial, to introduce the podcast's vision and explore Kevin's entrepreneurial journey. They discuss Renovo's customer-centric approach to lending, emphasizing the importance of storytelling from successes and setbacks. Kevin shares his early experiences in the lending business, from selling ice as a child to establishing Renovo as a leader in real estate finance. This episode provides insights into how Renovo builds meaningful client relationships and focuses on delivering exceptional customer service across various local markets.Key Points from This Episode[00:00:00] Introduction to the podcast and its purpose[00:01:43] The podcast's format and goals[00:02:49] Kevin's enthusiasm for sharing business stories and learning from them[00:04:35] Kevin's journey from selling ice to becoming a top loan officer[00:09:11] Kevin discusses starting in his father's lending business in high school[00:13:41] The evolution of Kevin's role and growth in the lending industry[00:21:04] Rebuilding after the financial crisis and the birth of Renovo[00:24:29] The importance of local expertise and customer service at Renovo[00:30:25] Kevin's insights on building long-term relationships with clients[00:32:23] James reflects on his journey with Renovo and his excitement for the futureLinksRenovo FinancialKevin Werner on LinkedInJames Gaskin on LinkedIn
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