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

In 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 – Introduction

0:56 – 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

Links

Devin on LinkedIn - https://www.linkedin.com/in/devin-ramos-602a811ab

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

Renovo Financial - https://renovofinancial.com/

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/

In 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/

In 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 strategy

21:36 – 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/

In 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/