In 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 took
• The painful reality of transitioning into the corporate world with a $65K salary
• How Dean discovered real estate and landed his first wholesale deal with no money
• Lessons from losing six figures in bad deals—and how he bounced back
• The birth of Deal Champs and how it grew into a national real estate movement
• Why investing in yourself and asking for help can shortcut years of pain
• How Dean’s family and freedom mindset fuel his hustle every day

Timestamps:

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 freedom

Links

Renovo Financial - https://renovofinancial.com/

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

In 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 Episode

00:00 — 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.

Links

Renovo 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

In 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 Episode

00:00 — 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.

Links

Renovo Financial - https://renovofinancial.com/

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