The Hustle Harder Show

In this premiere episode of the new Hustle Harder roundtable format, host James Gaskin is joined by Renovo Financial CEO Kevin Werner and Chief Credit Officer Darren Weaver to unpack current events shaping the U.S. economy and housing market. The trio revisits predictions from earlier in the year and evaluates how they’ve held up amid Moody’s credit rating downgrade, rising national debt, and persistent inflation. With their signature blend of insight and banter, they discuss whether the downgrade truly matters for investors, and how shifting interest rates might shape the remainder of 2025.

The conversation then turns to the state of the housing market, where trends in affordability, inventory, and regional market performance take center stage. From the surprising resurgence of older urban markets like Chicago and Boston to the growing pains of boomtowns like Austin, Kevin and Darren emphasize the importance of local knowledge, product-market fit, and disciplined investing. With actionable strategies like mortgage rate buy-downs and hyperlocal focus, this episode lays the foundation for a practical, insightful new series designed to help real estate professionals thrive in any market.

Key Points from This Episode

00:00 – Intro to the new roundtable format and weekly cadence

01:29 – Introducing Darren Weaver and Kevin Werner

04:41 – US credit downgrade: what it means, and does it matter?

12:11 – Market reaction and long-term implications of the downgrade

13:21 – National housing update: inventory, affordability, and trends

16:47 – Regional breakdown: where supply is rising and where it’s tight

20:00 – Logan Mohtashami’s “savagely unhealthy” market, revisited

22:27 – Why product-market fit is everything right now

24:51 – Chicago’s resurgence and strength in legacy markets

27:14 – Mid-year market awards: NE leads, Chicago steady, CA resilient

30:23 – Challenged markets: Austin and Tampa overbuild examples

33:56 – Real estate discipline vs. chasing speculation

36:23 – Interest rates: hope vs. operational readiness

39:16 – 7%+ rates: normalizing the new normal

42:03 – Builders using rate buy-downs as sales strategy

45:42 – The gap in smaller investor awareness of buy-downs

48:11 – Actionable tip: partner with local mortgage pros for better rates

50:46 – Tariffs, labor pressure, and proactive cost planning

53:10 – Supplier conversations: relationship-building & preparation

56:28 – Don’t be a bottom-20% customer: how to stay prioritized

59:06 – Random WSJ article game: Art Deco vs. Affordable Housing

1:01:25 – Final thoughts on preservation, change, and smart development

1:03:36 – Sign-off and teaser for next roundtable episode

Links

Renovo Financial - https://renovofinancial.com/

James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/

In this episode of the Hustle Harder podcast, host James Gaskin sits down with Patrick Soares, a South Florida-based real estate investor and construction entrepreneur. Starting from a family-run countertop business, Patrick walks us through his journey of intentional growth in real estate — from his first rental in 2013 to a 94-unit portfolio today. He shares the pivotal moment when he shifted from side hustle to scaling up, the importance of setting clear goals (like retiring at 35), and how he built and refined his business model through partnerships, out-of-state investing, and strategic property management. Patrick also opens up about managing risk, market challenges like rising insurance costs, and why quality always trumps door count.

Key Points from This Episode

0:00 – Intro: Meet Patrick Soares

1:00 – From countertops to construction to real estate

3:30 – Buying the first rental and learning through family

6:45 – Intentional growth and setting the goal to retire by 35

9:15 – Scaling from 7 units to 94 — and how he did it

13:40 – Expanding into North Carolina with a new partner

17:15 – Focusing on quality over quantity in 2025

21:00 – Realities of risk, cash flow, and portfolio management

23:50 – Letting go of control: Lessons in hiring property managers

28:00 – Managing locally vs. out-of-state

32:15 – What to look for in a good property manager

36:30 – Vetting and interviewing PMs: Patrick’s checklist

41:00 – Communication, alignment, and ethical practices

44:45 – Building strong vendor relationships and long-term loyalty

50:55 – Florida’s insurance challenges and market implications

59:30 – Why Patrick is still buying and what smart investing looks like now

1:02:50 – Long-term thinking, surviving the cycles, and advice for new investors

Links

Renovo Financial - https://renovofinancial.com/

James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/

In this episode of Hustle Harder, James Gaskin sits down with Brentin Hess, a dynamic real estate investor from Pasadena, Maryland. Brentin shares his journey from growing up in a real estate family to flipping his first house at 21 and scaling up to 100 flips annually. He reflects on the lessons learned from early challenges, the importance of trustworthy contractors, and the value of building a supportive investor community. Brentin also discusses his strategies for sourcing deals, work-life balance with a growing family, and plans for expanding his investor network into new markets.

Key Points from This Episode

[00:00:00] Brentin’s early exposure to real estate through his family and his first flip at 21

[00:03:02] Diversifying his portfolio: flipping, commercial properties, and rentals

[00:05:18] Challenges of scaling a business to 100 flips per year

[00:09:07] Sourcing deals through realtors, wholesalers, and direct-to-seller marketing

[00:12:13] Lessons learned from contractor relationships and how to avoid costly mistakes

[00:17:15] Navigating the ups and downs of managing rental properties

[00:21:46] The pivotal role of a trusted contractor in Brentin’s scaling journey

[00:28:23] Building an acquisitions team and leveraging virtual assistants

[00:33:17] Insights on local markets and staying focused within Maryland’s suburban areas

[00:39:35] Strategies for maintaining work-life balance with a growing family

[00:50:02] Founding and scaling the Maryland Investor Network to foster community growth

Links

Renovo Financial - https://renovofinancial.com/ 

James Gaskin on LinkedIn - https://www.linkedin.com/in/james-gaskin-b675593/ 

Brentin Hess on LinkedIn - https://www.linkedin.com/in/brentinhess

In this episode of Hustle Harder, James Gaskin interviews Jon Grabowski, CEO of Red Cedar Capital Partners. Jon shares his journey from a pharmaceutical sales rep to a leader in real estate development, detailing Red Cedar Capital's innovative approach to land development and home building. He discusses the company's growth, the importance of relationships and trust, and the role of thoughtful design in creating affordable, high-quality homes. Jon also highlights his work-life balance strategies and the significance of long-term partnerships in business success.

Key Points from This Episode

[00:01:01] Overview of Red Cedar Capital and its operations

[00:01:39] Jon’s early career and entry into real estate

[00:02:23] Challenges faced in the Detroit real estate market

[00:03:25] Impact of the 2008 financial crisis on Jon's career

[00:04:26] Pivoting during COVID-19 and the growth of Red Cedar

[00:06:05] The importance of thoughtful design in home building

[00:08:46] Jon’s daily routine and work-life balance

[00:11:53] Expansion strategy and market selection

[00:19:33] Addressing affordability in housing

[00:23:21] The role of community and thoughtful business practices

[00:26:28] Memorable projects and lessons learned

[00:30:05] The significance of multiple exit strategies in deals

[00:34:07] Building a disciplined and autonomous team

[00:37:04] Hiring practices for cultivating ownership and accountability

In this episode of Hustle Harder, James Gaskin sits down with Paul Sparks, a real estate investor based in Denver, Colorado, and founder of The Whale Club. Paul shares his unconventional journey from engineering sales to real estate investing, discussing the evolution of his business strategy, the importance of relationships, and the lessons learned along the way. He emphasizes the value of understanding your buyer, the power of local knowledge, and the importance of building a reliable business. Paul also dives into his experiences with flipping houses, developing townhomes, and leveraging relationships to succeed in a competitive market. Tune in for an in-depth look at how Paul navigates the challenges of real estate, scales his business, and plays the game of business like a sport.

• Paul's journey from engineering sales to real estate investing.
• Discovering real estate as a path away from corporate travel.
• The impact of the COVID-19 pandemic on Paul's career shift.
• Paul's first investment properties and lessons learned.
• The "deal triangle"–sourcing, funding, and operations.
• Building partnerships and identifying value in business relationships.
• Challenges faced during development projects, including unexpected setbacks.
• Balancing large developments with more consistent flipping income.
• Paul's approach to finding his niche in the flipping market.
• Avoiding common mistakes when flipping homes and staying focused.
• The importance of flexibility and learning in the early stages of business.
• Understanding your buyer: Paul's focus on serving his ideal client.
• Building trust and navigating the real estate ecosystem in Denver.
• Leveraging relationships for success and finding the right partners.
• Insights on paying to access valuable networks and A-player circles.
• Paul's business philosophy: balancing reliability with big opportunities.
• Introducing The Whale Club and helping investors build reliable businesses.
• Closing thoughts: clarity of purpose and playing the long game in business.

Links:

Renovo Financial-https://renovofinancial.com/

James Gaskin on LinkedIn-https://www.linkedin.com/in/james-gaskin-b675593/

Whale Club-https://www.realestatecertainty.com/

In this episode of Hustle Harder, James Gaskin interviews Jeff Nydegger, co-founder of Kendall Partners, a top direct-to-seller house-buying company in Chicago. Jeff shares his journey from military service to building a successful real estate business with his partner, Kevin Hanson. He explores their early challenges, including launching during the 2008 financial crisis and the strategies that helped them grow. Jeff highlights the significance of strong partnerships, the power of a trusted brand, and the importance of playing the long game. Tune in to hear how grit, strategic pivots, and team culture have fueled Kendall Partners' success.

Key Points from This Episode

• Jeff's journey from military service to real estate.
• Partnering with Kevin Hanson and their early business dynamic.
• Discovering a passion for real estate while deployed in Afghanistan.
• Challenges faced during the 2008 financial crisis.
• The importance of freedom in time, money, and relationships.
• Evolving their business model and strategies.
• Building a strong culture and hiring based on core values.
• Jeff's philosophy on playing the long game and maintaining grit.
• The role of coaching and mentorship in business growth.
• Building trust through strong relationships and referrals.
• Developing a resilient company culture and leading by example.
• Scaling Kendall Partners: from local player to market leader.
• Challenges of rapid growth and maintaining core values.
• Strategies for managing a large team and staying agile.
• Jeff's vision for Kindle Partners' future and upcoming challenges.

Links

Renovo Financial: https://renovofinancial.com/

James Gaskin on LinkedIn: https://www.linkedin.com/in/james-gaskin-b675593/

Kendall Partners: https://www.kendallpartnersltd.com/

Jeff Nydegger on LinkedIn: https://www.linkedin.com/in/jeff-nydegger-8b5bb42/

In 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 ahead

Key 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.

Links

Renovo 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

In 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 business

Links

7 Pines

Scott Randall on LinkedIn

James Gaskin on LinkedIn

In 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 future

Links

Renovo Financial

Kevin Werner on LinkedIn

James Gaskin on LinkedIn

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.