Most investors know property management is critical to rental property success, but very few know the right questions to ask before choosing a manager. The truth is, better questions lead to better results.

On this episode, Gregg sits down with Kate Winter from JWB’s property management team to break down the key questions every investor should ask before hiring. You’ll learn how to spot if a manager’s incentives align with your goals, how their team and systems are built to deliver on the promise of consistent returns, and what separates the best from the rest.

They'll cover topics like:

- What is the telltale sign that will tell you that you can trust a PM longterm?
- How can property managers prioritize relationships in a way that adds value beyond the investment?
- Why is transparency so key to staying in the game as an investor?

If you’re serious about building a rental portfolio that performs for the long run, this conversation will show you how to evaluate property management the right way — before you sign on the dotted line.

Listen NOW!

Chapters:

00:00 Introduction and Welcome
01:57 Meet Kate Winter: Property Management Expert
03:19 Common Questions When Hiring a Property Manager
07:25 Understanding Property Management Fees
08:33 Maintenance and Goal Alignment
19:38 The Importance of Renewals
24:06 Resident Experience and Satisfaction
30:58 Aligning Goals for Better ROI
31:17 Ensuring Resident and Investor Satisfaction
31:41 Addressing Viewer Questions
32:06 Implementing AI in Property Management
34:04 Property Management Software
35:08 Maintenance Fees and Vendor Selection
39:19 Setting and Adjusting Rent
41:06 Unique Property Management Structure
43:41 Specialized Roles in Property Management
48:51 Client Service and Communication
51:16 Rapid Fire Q&A
59:34 Concluding Remarks and Upcoming Events

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

This week on Not Your Average Insights, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez discuss President Trump’s landmark executive order that opens the door for Americans to invest their 401(k) retirement savings in alternative assets like cryptocurrency, private equity, and real estate along with other interesting headlines for real estate investors.

We’ll explore:

- How will this executive order affect the investment real estate market?
- What the rise in age of 1st time home buyers means for the housing market
- Why professional sports franchises are becoming sophisticated real estate investors

Listen NOW!

Chapters:

00:00 Introduction and Overview
00:06 Executive Orders and 401k Investments
00:26 Football Season and Stadium Deals
01:48 Welcome to the Show
02:28 Alternative Assets in 401k Plans
03:05 Real Estate vs. Other Investments
05:20 Challenges and Opportunities in Real Estate
08:00 JWB's Business Model and Fund Structures
16:42 Median Age of Home Buyers
17:24 Affordability Challenges and Solutions
18:45 Investing in Workforce Housing
19:19 The Importance of Home Ownership
24:49 Encouraging Young People to Invest
29:08 Understanding Real Estate Affordability
29:34 Teaching Kids About Real Estate
30:11 The Importance of Financial Education for Kids
30:43 The Role of Relationships and Education in Real Estate
31:24 Challenges and Opportunities in Real Estate Investment
32:22 Discussing Real Estate with Kids
33:36 Community Shares and Foreign Investment
34:17 The Economic Impact of Professional Sports Teams
35:21 Stadium Deals: Downtown vs. Suburban
42:03 Jacksonville's Stadium Renovation and Economic Growth
49:14 Addressing Real Estate Taxes and Affordability
53:56 Future Topics and Closing Remarks

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

Are tales of rising insurance rates making you second-guess investing in Florida real estate? For the past two years, headlines have fueled fear but the reality looks very different today.

On this episode of the Not Your Average Investor Show, we’re bringing back community favorite Whitney Ricci to clear the air. Her past appearances drew record attendance, and she’s back with critical updates investors need to hear.

Join JWB Co-Founder, Gregg Cohen, and Show Host, Pablo Gonzalez, as they talk with Whitney about:

- The New Reality of Florida Insurance: What’s actually happening in the market and why things are turning around
- Conquering Investor Anxiety: Straight answers to your biggest concerns about hurricanes and insurance risks
- Unlocking Opportunity: How up-to-date info can give you a strategic edge in Florida investing

Don’t let old headlines shape your decisions. Get the facts, understand the trends, and move forward with confidence.

Listen NOW!

Chapters:

00:00 Introduction and Welcome
01:32 Meet the Guests
02:23 Insurance Market Overview
02:43 Florida's Insurance Crisis
07:31 Tort Reform and Its Impact
08:11 Current Insurance Landscape
25:25 Hurricane Season Preparedness
32:59 AI and Technology in Insurance
35:00 Reflecting on AI's Impact on Insurance
35:22 A Real-Life Example of AI in Claims Processing
36:39 The Humanizing Effect of AI in Business
37:33 Predictions for AI in Future Hurricane Seasons
40:47 Understanding Sinkhole and Catastrophic Ground Collapse Coverage
45:37 Proactive Measures for Insurance Rate Reductions
47:40 High-Risk Umbrella Insurance and New Carrier Options
50:39 Flood Insurance and Risk Management
58:18 Fun Memories and Community Engagement
01:01:24 Charity Referral Program and Final Thoughts

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

This month’s Portfolio of the Month isn’t just about property selection, it’s about tax deferment and leverage.

JWB Co-Founder Gregg Cohen and host Pablo Gonzalez break down how property selection goes when you use a 1031 Exchange.

You’ll see:
- Why you need an easy way to pick properties to meet the 45-day and 180-day rules 
- How “like-kind” requirements shape your next purchase
- What type of mistakes can cost you hundreds of thousands of dollars in a 1031 exchange 

If you own an investment property, this episode will show you how to multiply your returns without multiplying your tax bill in one easy to understand case study.

Listen NOW!

Chapters:

00:00 Introduction to 1031 Exchange
01:24 Meet the Hosts: Pablo Gonzalez and Gregg Cohen
01:43 Understanding the Importance of 1031 Exchange
03:21 How 1031 Exchange Works
05:41 Real-Life Example: California Property
06:44 Maximizing Tax Savings with 1031 Exchange
09:14 Interactive Q&A: Alex Diaz's Scenario
11:07 JWB's Portfolio Generator Explained
15:34 Selecting Properties for 1031 Exchange
16:08 Key Players and Timelines in 1031 Exchange
20:40 Financial Engineering: Optimizing Your Investment
25:13 Interest Rates and Down Payments
29:48 Investment Down Payment Strategy
30:13 Maximizing Tax Savings
30:50 Adjusting Down Payments for Optimal Returns
33:14 Exploring Additional Property Investments
36:08 Handling Unexpected Scenarios
40:04 Q&A Session
42:46 Community Engagement and Future Plans

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

Feeling stuck investing only where you live? Many believe local real estate is their only option but what if you could build wealth from anywhere?

On this episode of the Not Your Average Investor Show, we're joined by Michael Santorios, a highly mobile JWB client who retired at 53 after building a long-distance rental portfolio that gave him freedom and peace of mind.

Join JWB Co-Founder, Gregg Cohen, and Show Host, Pablo Gonzalez, as they talk with Michael about:

- Overcoming the “time crunch” of hands-on, local investments
- Leveraging a 1031 exchange to build a remote portfolio in Jacksonville
- Achieving stress-free passive income and a truly mobile lifestyle through JWB’s turnkey model
- Gregg’s insights on “time ownership” and how Michael’s portfolio gained in appreciation

This is a powerful conversation for anyone looking to break free from traditional real estate constraints and embrace a truly location-independent investing strategy.

Listen NOW!

Chapters:

00:00 Introduction and Welcome
02:19 Michael Santorios' Real Estate Journey Begins
03:42 Gregg's Similar Start in Real Estate
04:41 Challenges and Realizations in Property Management
05:03 Transition to High Tech and Expanding Portfolio
07:15 Meeting Gregg and Formulating a Plan
12:42 Achieving Financial Freedom
22:59 The Importance of Team and Market Selection
29:29 Advanced Real Estate Strategies and Tax Benefits
31:04 Promoting the Jacksonville Real Estate Market Report
32:13 Introduction to Jacksonville Real Estate Report
34:11 The Importance of Local Focus in Real Estate
35:16 Michael's Referral Success Story
36:02 Understanding Investment Portfolios and End Games
37:45 The Benefits of Real Estate Over Stocks
41:44 Michael's Real Estate Portfolio Breakdown
44:02 Tax Strategies and 1031 Exchanges
48:03 Michael's Retirement and Cash Flow Strategy
57:44 Final Thoughts and Community Engagement

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

With the Fed's latest decision to hold rates, one thing became clear- tariffs are already affecting the real estate market.

This week on Not Your Average Insights, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez break down the role tariffs play in the Fed’s decision, and other headlines to consider.

We’ll talk about:

•⁠  ⁠Why the Fed’s pause on rate hikes is tied to tariffs
•⁠  ⁠What Florida’s governor is proposing that has everyone looking at Florida real estate
•⁠  ⁠Where the “10 Slowest Housing Markets” were reported to be, and which ones we agree with
•⁠  ⁠and more!

Listen NOW!

Chapters:

00:00 Introduction to Not Your Average Insights
01:24 Welcome Back to the Show
04:13 Discussion on Fed's Interest Rate Decision
06:05 Impact of Tariffs on Housing Market
13:05 Jobs Report and Fed's Future Decisions
19:34 Ron DeSantis' Proposal to Eliminate Property Taxes
25:06 Debating Property Tax Elimination
25:44 Governor's Perspective on Government Spending
26:19 Impact of Sales Tax on Different Income Groups
26:54 Feasibility of Sales Tax Increase
28:57 Potential Property Tax Rebate
29:14 Revisions to Government Job Numbers
32:52 Interest Rates and Mortgage Market
36:59 JWB Cares Fundraising Update
38:25 Analyzing Housing Market Data
42:54 Long-Term Investment Strategies
49:40 Conclusion and Upcoming Events

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

Downtown Jacksonville is starting to feel different—and that’s not by accident.

New developments, ambitious planning, and private-public partnerships are creating serious momentum… but what does that mean for you as an investor?

That’s why we’re bringing Bryan Moll, CEO of Gateway Jax, back to update us on what’s really happening downtown, and how it could impact long-term rental property values.

 Join show host Pablo Gonzalez as he talks to Bryan about: 

- The strategy behind the Pearl Street District and why it matters for Jacksonville
- What other developments are spurring up now that Pearl street has started
- How to spot the early signs of explosive market transformation
- What Bryan’s work in Tampa and Austin taught him—and why Jacksonville is next

If you’ve been wondering how downtown revitalization impacts rental investors, this is your chance to go behind the scenes with the guy leading the charge.

You’ll leave this episode with a clearer view of where Jacksonville is headed—and how to get ahead of it.

Listen NOW!

Chapters:

00:00 Introduction and Welcome
00:10 Revitalizing Downtown Jacksonville
00:42 Introducing Gateway Jacks and Bryan Moll
02:19 The Genesis of Gateway Jacks
03:51 Pearl Square: Inspiration and Vision
05:33 Placemaking and Urban Design
07:46 The Role of Public Spaces and Retail
10:25 Jacksonville's Growth and Future Plans
11:36 Pearl Square Project Details
21:35 Brooklyn Neighborhood and Urban Activation
26:43 Urban Development Patterns in Various Cities
27:16 Challenges and Successes in Tampa's Urban Projects
29:20 Jacksonville's Economic Fundamentals and Growth
33:25 Institutional Investment in Jacksonville
44:23 Entertainment and Cultural Venues in Downtown Jacksonville
46:04 Community Questions and Future Developments

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

Life-changing wealth in rental properties comes from the five profit centers of rental property investing but most investors focus on only one when choosing a market.

The truth is…the market you invest in plays a crucial role in maximizing all five. That’s why we’re here to break down the top rental property markets and show how they really stack up.

Join Gregg Cohen, Co-Founder of JWB Real Estate Capital, as he helps you learn:

- What investors think matters most when picking markets (and what actually does)
- How the 5 profit centers stack up across today’s strongest markets
- What to watch for in 2025 that could unlock even bigger returns
- And more!

This is one of the most requested topics and we’re bringing it to you live with real data, strategy, and answers to your questions.

Listen NOW!

Chapters:

00:00 Introduction and Recap
00:29 The Importance of Market Selection
02:15 Introducing the Home Step Program
03:41 Success Stories and Impact
08:09 Fundraising for Home Step
13:49 Finding the Best Market to Invest
15:56 The Five Profit Centers of Rental Property Investing
22:09 Criteria for Choosing the Best Market
28:22 Red Flags to Avoid in Market Selection
29:48 Understanding Cash Flow in Real Estate Investments
30:12 Identifying Red Flags in Real Estate Markets
32:00 Rating and Comparing Real Estate Markets
34:03 Analyzing Top Real Estate Markets
41:41 The Importance of Balanced Markets
42:44 Jacksonville: A Prime Investment Opportunity
43:46 Resources for Real Estate Market Data
50:23 Community Engagement and Future Developments

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

Rental properties can look amazing on paper. That’s exactly why you need to know what to watch out for.

In this episode of the Not Your Average Investor Show, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez break down real deal sheets from other turnkey providers to reveal how numbers can be stretched, spun, or conveniently left out.

You’ll learn:

- The common line items that get manipulated to make deals look better
- How small tweaks can dramatically impact your projected returns
- Why JWB is committed to transparency, even when it means showing lower numbers
- What questions savvy investors ask before saying “yes”

If you want to separate the hype from the real value, this episode is for you.

Listen NOW!

Chapters:

00:00 Introduction and Welcome
01:35 Setting the Stage: The Importance of Evaluating Deals
01:56 Greg's Approach to Deal Evaluation
06:56 Understanding Turnkey Rental Properties
09:18 Key Questions Before Analyzing a Proforma
22:36 Common Pitfalls in Turnkey Evaluations
25:03 Breaking Down a Real Proforma
25:28 Introduction to Key Investment Factors
26:03 Understanding Turnkey Properties
26:44 Evaluating Rehab Costs and Risks
28:14 Analyzing Financial Assumptions
30:45 Spotting Red Flags in Proformas
39:03 Q&A Session
42:34 Concluding Thoughts and Advice

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies

Every investor loves a success story, but what about when things don’t go as planned?

On this episode of the Not Your Average Investor Show, we’re diving into what happens after a rental property investment goes wrong and how some investors come out even stronger.

Join Allie King, the manager of the JWB Portfolio Management department, and Not Your Average Investor Show host, Pablo Gonzalez, as they help you understand:

- The most common reasons investors lose confidence in real estate
- What bad buys and bad experiences really look like in the field
- How vertically integrated support can turn failure into long-term success
- What steps you can take if you’re looking to bounce back from a rough investment

This will be a candid, empowering conversation for anyone who's had doubts, setbacks, or second thoughts about their investment journey.

Listen NOW!

Chapters:

00:00 Introduction and Show Overview
01:44 Meet the Guest: Allie King
02:09 Allie King's Journey at JWB
04:34 Common Mistakes of First-Time Investors
05:33 Leslie Wilson's Real Estate Journey
07:05 Importance of Market Knowledge
14:43 Understanding Turnkey Real Estate
15:39 Jag Chatta's 1031 Exchange Experience
16:54 Navigating 1031 Exchanges Successfully
20:12 Real Turnkey vs. Fake Turnkey
27:23 Comparing Market Options
29:22 Challenges of High HOA Fees
30:47 Navigating HOA Decisions
35:04 Transitioning from Active to Passive Investing
36:30 Airbnb vs Long-Term Rentals
43:42 Landlord-Friendly Markets
49:16 Annual Performance Reviews
54:04 Final Thoughts and Community Engagement

Stay connected to us! 

Join our real estate investor community LIVE: 
https://jwbrealestatecapital.com/nyai/

Schedule a Turnkey strategy call: 
https://jwbrealestatecapital.com/turnkey/ 

*Get social with us:*
Subscribe to our channel  @notyouraverageinvestor  
Subscribe to  @JWBRealEstateCompanies  
🌐 Facebook Group - https://www.facebook.com/groups/rentalpropertyinvesting
📸 Instagram - https://www.instagram.com/nyai_community
📸 Instagram - https://www.instagram.com/jwbrealestatecompanies