The Hustle Harder Show

In this episode of Hustle Harder, James Gaskin and Abbey Hearn sit down with John Robbart, who runs Renovo Financial’s lending business in Tampa. John shares how he went from working in San Diego nightlife to private lending, why he moved to Tampa before having a job offer from Renovo, and how he built his presence in a new market. He also discusses surpassing $100 million in annual production, learning to delegate to his team, building a local office culture, creating social media content, and preparing for fatherhood.

Key Points from This Episode

0:00 – Intro and welcoming John Robbart

00:52 - John’s transition from San Diego nightlife into private lending

02:35 - Betting on himself through career changes and the disruption of COVID

04:30 - Starting an independent lending business and learning from Paul Shaughnessy

06:12 - Discovering the opportunity in Tampa and deciding to build a business there

09:32 - Moving to Tampa without a guaranteed position at Renovo

11:09 - Crossing $100 million in annual production and setting a $200 million stretch goal

12:41 - Preparing for fatherhood and embracing a major life change

13:43 - How John and Taylor met in San Diego and built their life together

16:15 - The team supporting John’s lending business and how their roles fit together

17:15 - Expanding Renovo’s Tampa office and building an in-person culture

18:45 - How delegation allows John to focus on bringing in new business

20:57 - The advice John would give himself about trusting the team and moving to the next opportunity

22:23 - Building John’s social media presence and batching weeks of content at a time

23:35 - Learning that social media performance can be difficult to predict

24:35 - John’s Celsius habit and early-morning routine

26:01 - Life in Tampa, the Tampa–St. Pete rivalry, and being more of a pool person than a beach person

27:47 - John’s unexpected first encounter with a manatee

28:39 - Favorite Tampa date-night spots, food, and local culture

30:09 - Tampa’s cigar scene and using cigars as a social activity with clients

32:40 - Staying connected to Boston after moving to Florida

33:35 - Hurricanes, flood preparation, and the challenges of property insurance in Florida lending

36:25 - The impact Paul Shaughnessy has had on John’s career and life

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

John Robbart on LinkedIn - https://www.linkedin.com/in/johnrobbart/

In this live episode of the Hustle Harder Show from Renovopalooza in Chicago, James Gaskin sits down with real estate investors Teo Scorte and Tom Shallcross, alongside Eric Workman. Teo and Tom share how they built their businesses, lessons learned from difficult deals, and why grit, financial literacy, and strong relationships matter in real estate. They also discuss Chicago’s real estate market, what they value in a lending partner, managing unexpected challenges, and advice for young professionals looking to build long-term wealth.

Key Discussions From This Episode:

[00:00:00] Intro

[00:01:19] Live introduction from Renovopalooza in Chicago

[00:02:37] Teo’s early exposure to construction and transition into real estate development

[00:03:33] How real estate gave Teo greater flexibility and time with his family

[00:05:55] Tom’s path from tech sales to full-time real estate investing

[00:06:47] Family, freedom, and controlling your own schedule

[00:10:16] Why Teo and Tom concentrate primarily on real estate investments

[00:11:38] Teo’s experience through the 2008 crash and rebuilding through construction

[00:14:57] Tom’s high-end flips and smaller multifamily investment strategy

[00:15:54] Building the Straight Up Chicago Investor podcast

[00:17:23] Teo’s demolition-court scare and the importance of a strong team

[00:19:38] Tom’s experience buying a property involved in title fraud

[00:20:39] Why experience and resilience matter when real estate deals go wrong

[00:22:31] Grit and purposeful action as foundations for real estate success

[00:24:05] Why Teo pairs grit with strong financial literacy

[00:24:52] Eric on the importance of relationships and building a strong network

[00:26:38] Tom’s perspective on the long-term opportunity in Chicago real estate

[00:29:04] Teo’s outlook on Chicago and why he continues investing locally

[00:30:14] Chicago’s ability to attract young talent from across the Midwest

[00:33:10] Speed, consistency, and culture in choosing a lending partner

[00:36:04] Why reducing friction and creating certainty matters to borrowers

[00:37:58] Maintaining client relationships in a competitive lending market

[00:39:47] Teo’s advice for Renovo employees as the company grows

[00:41:11] Tom on making every client interaction as simple as possible

[00:42:11] How company culture and consistency shape the borrower experience

[00:44:34] Teo’s stories about building relationships with Daniel Rosen and the Renovo team

[00:48:13] Tom and Eric’s early relationship and first lending experiences together

[00:50:35] Common mistakes investors make when evaluating deals

[00:52:54] Maintaining discipline instead of forcing the numbers on an acquisition

[00:54:35] Turning appraisal misses and unexpected problems into actionable information

[00:56:23] Using scenario analysis to account for uncertainty when underwriting

[00:57:47] Teo’s advice to young professionals: save money and build toward generational wealth

[00:59:39] Tom’s advice to learn from experienced developers, save, and take action when ready

[01:00:02] Closing remarks from Renovopalooza

Links:

Renovo Financial - https://renovofinancial.com/

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

Teo Scorte on LinkedIn - https://www.linkedin.com/in/teo-scorte-ab51b815/

Tom Shallcross - https://www.linkedin.com/in/tomshallcross/

Eric Workman - https://www.linkedin.com/in/eric-workman-1681996/

Straight Up Chicago Investor Podcast - https://www.straightupchicagoinvestor.com/podcast

In this episode of Hustle Harder, James Gaskin and Abbey Hearn sit down with Travis Sperr, Managing Director of Lending for Colorado at Renovo Financial. Travis shares how growing up working alongside his contractor father shaped his understanding of construction and eventually led him into real estate lending. He discusses building a strong Denver-based team, the value of firsthand investing and development experience, and why relationships, local market knowledge, grit, and consistent execution have helped drive the growth of his lending business.

Key Points from This Episode

0:00 – Intro and welcoming Travis Sperr

01:09 - Travis’s background, family, and life in Colorado

02:05 - Hiking 14ers, skiing, and outdoor life in Colorado

05:38 - Travis’s approach to fatherhood and raising capable adults

07:18 - Overcoming his fear of water through adult swim lessons

09:22 - Early-morning workouts and the mental benefits of exercise

11:58 - Building Travis’s lending team and defining each team member’s role

12:22 - How a strong team creates leverage and improves the client experience

14:58 - Growing up working construction alongside his father

16:00 - How construction experience helps Travis advise lending clients

17:11 - Woodworking, building furniture, and working with his hands

18:50 - Travis’s experience as a real estate developer and investor

19:20 - Using firsthand deal experience to empathize with borrowers

21:04 - Entering real estate lending after the Great Recession

22:00 - Building a lending career while working a full-time sales job

22:40 - Buying rental properties and learning through repeated real estate deals

23:51 - The value of seeing many different projects as a lender

24:17 - Advice for new lenders: grit, repetition, guidelines, and relationships

26:27 - Growing annual lending volume beyond $100 million

27:00 - How local knowledge, referrals, and execution are driving continued growth

28:07 - Creating a strong culture within the Denver office

29:25 - Why personal relationships make Travis a better team leader

31:38 - Team goals, hydration, and the Denver office’s Bevi machine

33:05 - Rocky Mountain oysters and Travis’s high-protein diet

34:45 - Favorite Denver food spots and finding meals for different diets

35:40 - Travis’s recommendations for experiencing Denver and Colorado

36:49 - The Coors Brewery and its connection to Colorado

37:46 - Red Rocks, live music, and Travis’s favorite local cover band

38:33 - Denver patio culture and Travis’s favorite breakfast spot

40:37 - Derek Jeter, Travis’s father, and the people he considers his heroes

41:20 - Lessons from his father’s entrepreneurship, work ethic, and commitment to family

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

Travis Sperr on LinkedIn - https://www.linkedin.com/in/travis-sperr-8163977/

In this episode of The Hustle Harder Show, James Gaskin sits down with Nema Daghbandan, CEO of Lightning Docs and partner at Fortress Law, to examine the private lending market through the first half of 2026. They discuss intense competition among lenders, changing RTL and DSCR volumes, rising leverage, pressure on rates, and loan performance. They also address the Kiavi-Figure transaction, potential industry consolidation, geopolitical volatility, and how AI is beginning to reshape private lending and business operations.

Timestamps:

0:00 – Intro and welcoming Nema Daghbandan

01:35 – Nema Daghbandan’s background and Lightning Docs

02:18 – Why competition among private lenders has intensified

05:09 – What the data says about RTL loan volume in 2026

11:47 – How access to borrower data is changing lender competition

16:03 – Building a differentiated lending model

17:00 – Credit discipline in an increasingly competitive market

20:25 – Why leverage can matter more than interest rate to borrowers

21:33 – Rising leverage and the risks it creates for lenders

25:10 – RTL and DSCR interest rate trends

30:23 – Pressure from rates, taxes, insurance, and rental markets

33:32 – Balance-sheet lenders vs. institutional approaches to risk

37:21 – What foreclosure data says about loan performance

41:02 – Delinquencies, securitizations, and increased loan-buyer scrutiny

46:17 – Breaking down the Kiavi-Figure transaction

52:07 – What could shape private lending in the second half of 2026

53:42 – Why strong underwriting fundamentals still matter

57:38 – The outlook for further industry consolidation

1:00:01 – How AI is beginning to reshape private lending businesses

1:03:12 – What to expect at the upcoming Fortra Law event

Links

Nema Daghbandan on LinkedIn - https://www.linkedin.com/in/nemadaghbandan

Lightning Docs - https://lightningdocs.ai/

Renovo Financial - https://renovofinancial.com/

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

Jeremy Goldberg joins James and Abbey for another episode of the Hometown Hustle Series to talk about his unconventional path from the restaurant industry to becoming one of the top loan originators in the country. Jeremy shares lessons from hospitality, building culture inside the Liberty Corridor, family values, New Jersey pride, and the importance of leading with authenticity and relationships.

Key Points from This Episode

0:00 – Intro and welcoming Jeremy Goldberg

0:35 – Jeremy’s background and leading the Liberty Corridor

1:08 – From restaurant owner to real estate investor and lender

3:32 – “Cooking to closing” and Jeremy’s culinary roots

4:15 – Opening restaurants in Miami and lessons from hospitality

7:07 – How restaurant experience influences leadership today

8:39 – Competing in the New York/New Jersey lending market

10:36 – Renovo culture and building the Hoboken office

14:40 – The famous office money tree story

17:28 – Birkenstocks, jam bands, and personal style

18:34 – Jeremy’s glasses clip demonstration

20:47 – Family life, marriage, and raising two daughters

22:37 – Real estate market insights and lending discipline

29:16 – Challenges with excess capital in lending markets

30:25 – Building toward a billion-dollar Liberty Corridor market

31:32 – Scotsman Guide rankings and team success

33:17 – What actually annoys Jeremy

34:00 – Unique New Jersey culture and quirks

35:43 – Sopranos vs. Jersey Shore debate

37:16 – Bagels, pizza, and Northeast food opinions

38:51 – Bruce Springsteen and Jersey Shore stories

39:44 – Favorite Jersey Shore cast members

41:24 – Jeremy’s biggest role model growing up

42:15 – Books, shows, and why Ted Lasso resonates with him

43:27 – Final thoughts and 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

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

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

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

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/

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/