If a property keeps showing higher maintenance costs, is it still the best place to keep your capital?

This week on the Not Your Average Investor Show, Gregg Cohen and Pablo Gonzalez welcome back Michael Santorios to explore how to think through operational intensity, property performance, and whether a move like a 1031 exchange into newer construction may make sense.

You’ll Learn:
🔁 The 1031 question: What investors should think through before exchanging into newer construction.
📊 Looking beyond surface frustration: How experienced investors evaluate property performance through a bigger portfolio lens.
🏠 Business-minded property decisions: Why costs like tenant upgrades or repairs sometimes need to be weighed against turnover and long-term value.
📈 Portfolio stage matters: How your strategy changes when you move from simply buying properties to optimizing the ones you already own.

This is a helpful episode for investors who want to make more thoughtful portfolio decisions with clarity and confidence.

Listen NOW!

Chapters:

00:00 Sell or Hold Big Questions
01:28 Meet the Hosts and Guest
02:13 Breaking Rent Payout Milestone
03:47 Michael Portfolio Snapshot
05:31 Pacman Profit Centers Explained
07:22 Rebalancing and 1031 Idea
11:00 Maintenance Emotion vs Math
18:03 Greg Numbers Based Reality Check
23:08 Long Term Investing Mindset
28:47 Portfolio Cashflow Scorecard
31:26 Sky Drive Case Study Setup
32:28 Pro Forma vs Actual Returns
35:00 Market Value and ROI Reports
38:12 Tax Savings Explained
38:50 Appreciation And Rent Growth
41:25 Maintenance Surprise Breakdown
45:20 Paying For Big Repairs
47:43 Sell Or Hold Framework
50:51 Cap Rate Comparison
55:04 True Cost Of Selling
01:01:23 Decision To Keep Property
01:04:11 Rapid Fire Q&A Wrap
01:09:27 Final Takeaways And Thanks

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

We’re hearing Detroit come up in real estate conversations because of low prices and promises of cash flow. So we’re here to ask the question, “How does it compare to Jacksonville?”

This week on the Not Your Average Investor Show, Gregg Cohen and Pablo Gonzalez dig beyond surface level stats to do a deep market vs market comparison.

We’ll talk about:
✅ Short-Term Cash vs Long-Term Appreciation: how both markets compare over time
✅ Population Demographics and Growth: How long-term population trends affect risk and upside between both markets
✅ Neighborhood Class Comparisons: The sneaky tactic we see in most Detroit performas and how to see through it
✅ And Much More!!!

Listen NOW!

Chapters:

00:00 Detroit Hype Setup
01:36 Show Intro and Welcome
02:03 Spring Break Catch Up
03:10 Correcting Population Stats
04:49 Why Detroit Keeps Coming Up
07:37 Cash Flow vs Real Growth
10:25 Zooming Out on Appreciation
15:19 Long Term Data Mindset
17:36 Population Growth Drives Prices
22:21 Downtown Jacksonville Upside
28:05 Eight to Sixteen Hour Downtown
28:51 Downtown Flywheel Effect
29:47 Detroit Growth Reality Check
31:27 Jacksonville Sustainable Tailwinds
33:24 Zip Codes And Turnkey Ratings
36:23 Why Workforce Housing Wins
42:35 Risk Mitigation And Cash Flow
45:00 Workforce Housing Quick Test
49:13 Team First Then Property
51:57 Wrap Up And Next Week Preview

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 US-Iran conflict dominating headlines, real estate investors are asking the same question: Should I be worried?

We have a small update on it in last week’s market update, but in this episode of the Not Your Average Investor Show, Gregg Cohen and Pablo Gonzalez we are taking a closer look at how global conflict, especially involving Iran, can affect the economy, inflation, interest rates, and the housing market.

We’re also answering the questions everyone had in the market update that we didn’t get to!

You'll learn:
✅ Wartime Headlines: How global uncertainty can affect the housing market without changing the core principles of long-term investing.
📊 Historical Perspective: What past periods of war and uncertainty can teach us about how housing markets actually behave over time.
📍 Local Market Update Questions: How Jacksonville's growth and demand trends continue to support the bigger picture.
💡 Your next move: How to make thoughtful decisions as a long-term investor when the market feels uncertain.

Join us LIVE if you’ve been watching the news and wondering what it may mean for your portfolio, this episode will help bring clarity.

Listen NOW!

Chapters:

00:00 War and Housing Outlook
01:42 April Incentive Package
04:01 Roll Call and Q&A Setup
04:49 Multifamily vs Single Family Rents
08:06 Sharing the Market Slides
08:29 Military Deployments and Rental Risk
12:14 Taxes and Insurance vs Rent Growth
15:41 Florida Property Tax Relief Buzz
18:21 Cash Flow With 25% Down
21:33 Co-Living and Buying Plans
23:17 ADUs Bill 48 Impact
27:36 ADU Numbers That Work
29:38 Can JWB Manage ADUs
30:45 Lot Value Upside
31:22 Property Tax Cut Debate
33:42 Oil Prices Hit Housing
37:36 Supply Side Self Regulation
40:21 War Data Deep Dive Setup
42:35 Conflict Case Studies
50:25 Key Takeaways And Wrap
55:35 Community Thanks Next Topic

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

Join us for the Q2 2026 Jacksonville Real Estate Market Outlook by JWB. We'll be joined by Gregg Cohen, Co-Founder of JWB Real Estate Capital.

The headlines say home sales are falling. But is that actually what's happening in Jacksonville?

Here's what we'll cover:
✅ What's actually happening with Jacksonville home prices, inventory, and rents right now
✅ Why the headlines may be misleading and how to read the data the right way
✅ What rising mortgage applications could mean for buyers in 2026
✅ Where the market stands compared to JWB's earlier 2026 outlook

You won't want to miss this opportunity to get a clear, data-driven view of the Jacksonville real estate market straight from one of JWB's owners.

Listen NOW!

Chapters:

00:00 Q2 Outlook Kickoff
01:55 Why This Report Matters
05:00 Housekeeping And Disclaimers
05:57 Jacksonville Market Snapshot
06:40 Home Prices Normalizing
10:17 Rent Trends And PM Metrics
12:38 Multifamily Overbuild Q&A
14:18 Home Price Data Debate
16:20 Iran War And Rates
20:35 Demand Vs Supply Coil Effect
23:54 Investor Strength In Inflation
30:27 Military Deployment Concerns
32:05 Road To Housing Act Intro
33:54 Bill Status Overview
34:29 What’s Inside the Bill
35:39 Investor Limits Explained
36:32 Seven Year Sell Rule
37:58 Why Capital Won’t Fit
40:04 Build to Rent Fallout
44:30 Seasonal Doom Headlines
45:48 Month vs Year Data
49:10 Seasonality EKG Effect
51:13 2026 Predictions Check In
53:31 Three Investor Takeaways
55:24 Stay the Course Closing

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

Maintenance costs can feel unpredictable for real estate investors.
And when you do not know who is making the decisions, how pricing is being managed, or what work really needs to be done, it can create stress fast.

That’s why this week on the Not Your Average Investor Show, Gregg Cohen and JWB’s New Construction Senior Superintendent, Tom Leon, are taking you behind the scenes to show how JWB works to control maintenance costs before they turn into bigger problems.

You’ll learn:

✅ How JWB Helps Control Maintenance Costs Early: Why the biggest cost-saving decisions often happen before a repair is ever needed.
✅ In-House Project Management Changes: How JWB’s construction team helps guide the work from start to finish, instead of leaving investors to manage the process.
✅ Better Pricing Happens: Why having the right team and process in place helps create stronger pricing for clients.
✅ Scope Management Matters: How clear oversight helps make sure the right work gets done without adding unnecessary cost or confusion.
✅ The Vertical Integration Advantage: Why JWB’s model creates a smoother experience for investors during turns, renovations, and maintenance decisions.

This episode is about the system behind the work and how it helps create a smoother, more thoughtful experience for investors.

Listen NOW!

Chapters:

00:00 Low Maintenance Costs
01:14 Show Intro Guest
02:06 Market Update Promo
03:25 Why Maintenance Worries
04:47 Construction By Numbers
06:49 In House Team Breakdown
13:21 Managing Many Trades
16:45 Vendor System Savings
24:07 Investor Mindset Decisions
30:10 JWB Standard Explained
34:44 Vendor Fixes and QC
36:42 Turn Payments and Holdbacks
38:09 Renovation vs Turn Mindset
43:23 Accountability in Vertical Model
45:31 Live Q&A Vendor Onboarding
49:35 Standardization and Materials
50:25 Carpet vs Vinyl Decision
53:53 Owner Approval on Turns
56:33 Wrap Up and Next Steps

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

The real estate industry just got a new label for 2026: “The Great Reset.”

That phrase alone is enough to make investors uneasy.
But here’s the real question: Does reset mean retreat?

This week on Not Your Average Investor Show, Gregg Cohen and Pablo Gonzalez unpack the 2026 Emerging Trends in Real Estate Report from ULI and PwC and explain how this permanent recalibration changes the game for long-term investors.

You’ll learn:
✅ The Great Reset vs. Crisis: Why this moment is a strategic recalibration rather than a repeat of 2008.
✅ The Affordability Megatrend: Why providing workforce housing is the smartest market play for 2026.
✅ Suppressed Demand: How higher rates kept buyers on the sidelines and why that pent-up demand is coming back as rates adjust.
✅ Asset Adaptability: Why single-family rentals perform in both good times and bad and why that's your unfair advantage in 2026.

Smart, patient, fundamentals-first investors may have more leverage today than they realize.

Listen NOW!

Chapters:

00:00 ULI Report Preview
01:14 Show Welcome and Hosts
01:32 Q2 2026 Outlook Promo
03:10 Why ULI Matters
05:03 Trend One Great Reset
07:59 Back to Basics Operations
12:50 Bonus Why Next Decade
13:17 Return of Yield
19:33 Supply Shortage Worsens
23:51 Institutions Flood Housing
29:21 Distressed CRE Deals
30:12 Debt Maturity Opportunities
31:58 Demographics Drive Demand
35:02 Buy and Hold Wins
35:51 Smart Money Era
36:29 Interest Rate Fog
40:33 Affordability and Policy Risk
45:41 Resilient Asset Classes
49:24 Operations Beat Engineering
54:32 Wrap Up and Next Episodes

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 rentals still delivering what you invested for? Are they stronger today than yesterday, or are the tradeoffs getting bigger?

On the Not Your Average Investor Show, Gregg Cohen and Pablo Gonzalez are turning a Summit keynote into a practical conversation focused on one thing: how to make better rental property decisions right now. 

✅ The Promise of Rentals Today: What rental properties still do well in this market and what’s changed.
✅ Decision Filters That Matter Now: How to make confident buy or hold decisions without relying on predictions.
✅ Asset Class Lens: How to judge rental properties on fundamentals instead of headlines.
✅ Your Next Best Move: The clearest factors to weigh before you add your next rental property to your plan.

When you step back and look at rental properties through the right lens, you stop reacting and start deciding. That’s what this episode is built for.

Listen NOW!

Chapters:

00:00 Are Rentals Riskier
01:43 Q2 Market Outlook
03:48 Business Journal Spotlight
08:28 Summit Theme Origins
10:38 Five Years Whiplash
14:40 Thriving Through Chaos
17:47 2010 Inflection Point
22:34 Boring Beats Chaos
25:49 Boring Gets Better
31:18 Downtown Growth Engine
35:18 Downtown Momentum Feels Real
36:52 The Warren Buffett Comparison
43:15 Boring Investing Wins
44:19 Certainty Beats Shiny Objects
46:43 Passive Income Planning Tool
48:36 Refinance for Property Babies
54:02 Why and Meaningful Impact
56:37 Homeownership Mission HomeStep
01:00:04 Audience Q&A Septic to Sewer
01:01:34 AI at JWB Today
01:03:43 Allocation and Black Swan Strategy
01:08:48 Wrap Up and Next Week

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

New York, like many great cities in the US, has high wages and even higher real estate prices.  Add a growing anti-landlord political environment and you can see why it's hard for many to invest in their local market.

But investing isn't your only option.

That's why we are bring on John Williams, a real estate investor from Long Island, NY,  as our next guest investor on the Not Your Average Investor Show!

JWB's cofounder, Gregg Cohen, and show host, Pablo Gonzalez, will dive into John's story to uncover:

- why he decided he would invest in a market 1,000 miles away (instead of somewhere he can drive to)
- what made him choose Jacksonville out of all the Florida markets New Yorkers are flocking to
- how he is growing his real estate portfolio to fit his goals
- and much more!

John is famously known in our community as "Il Maestro".  Join us live to meet him on the show for the first time, and be part of the conversation!

Listen NOW!

Chapters:

00:00 Meet John Williams
01:56 Early Real Estate Spark
02:54 Self Managing Mistakes
03:35 Team First Mindset
04:59 JWB Community Breakthrough
06:42 First Buys and Fast Growth
07:57 Tree Damage Trust Test
10:02 Doing the Right Thing
12:37 Remote Landlord Lessons
14:15 Legacy and Identity
17:15 Why Community Changes You
20:00 Why Not New York
24:01 Spouse Buy In Matters
27:42 Goals for Ten Properties
29:08 Legacy Planning Goals
30:04 Three Phase Wealth Plan
31:21 Debt Snowball Paydown
33:25 Family Involvement Strategy
34:39 Portfolio ROI Breakdown
37:25 Credits And Buydowns
39:39 Real Estate Language 101
40:50 Cashflow Credits Explained
44:11 Reserves And Bank Accounts
46:14 Rate Buydown And DSCR
48:44 Pac Man Profit Centers
50:42 Retirement Funds To Real Estate
52:51 Team First And Summit Wrap
55:54 Final Takeaway Dont Be Average

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

So many people who want to invest in real estate know they're not ready yet, and want to find a path to get there, but can't find an example to follow.

That’s why this week on the Not Your Average Investor Show, Gregg Cohen and Pablo Gonzalez are joined by client investor, Gregory Roberts, to share what actually happens in the year between “not ready yet” and feeling confident enough to move forward.

Gregory showed up to the Not Your Average Investor Summit knowing he wasn’t ready to take action. Instead of forcing a decision, he focused on learning, gaining clarity, and giving himself time.

A year later, everything looked different.

In this conversation, you’ll hear:

✅ Why showing up before you feel ready can be a smart move
✅ How clarity builds when pressure is removed
✅ Who you need in your corner to get over the hump

Listen NOW!

Chapters:

00:00 What Can Change in a Year: From Observer to Investor
01:23 Summit Week Kickoff + Meet the Panel (Pablo, Gregg, Lee, Dr. Roberts)
02:26 How Dr. Roberts Found the Summit & the JWB Community
04:06 His ‘Why’: From Poverty to Advising Students Through Real Estate
07:27 Early Investing Journey: First Townhouse, First Rental Lessons (2017–2018)
09:25 Hitting the Wall: Traditional Lending Roadblocks After Relocating
11:39 The Breakthrough: Selling, 1031 Exchange, and JWB’s Step-by-Step Support
14:11 What ‘Real Turnkey’ Means: Condensing Years into a Few Calls
26:16 1031 Exchange Explained: Deferring Taxes to Buy More Real Estate
28:24 1031 Exchange Deadlines: 45-Day ID & 180-Day Close (No Wiggle Room)
28:50 How a Coordinated Team Makes a 1031 Exchange Actually Work
29:27 From One Property to Two: Understanding Capital Gains & the Exchange Flow
31:15 Real Estate as a New Language: Learning the Vernacular Through Repetition
32:52 Meeting People Where They Are: Teaching Investing with Analogies
37:14 Dr. Roberts’ Next Chapter: Growing a Portfolio & Helping Others Start
41:23 JWB’s Home Step Program: Helping Renters Become Homeowners at Scale
45:30 Summit Lightning Round: How to Get the Most Out of Not Your Average Investor
50:04 Final Send-Off: Community Impact, Gratitude, and “Don’t Be Average” 

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

You’ve probably heard us talk about “properties having babies” when investors use a cash out refi to buy new properties with no new capital.

But what does that actually look like when you’re the investor making the call?

In this episode, show host Pablo Gonzalez opens up his real-life portfolio to walk through the decision to do a cash-out refinance, and whether the short-term drop in cash flow is worth the long-term growth.

JWB co-founder, Gregg Cohen, will unveil a new tool he just developed that helps visualize the trade-offs investors face when they refinance like:

➕ What changes immediately in your monthly cash flow
➕ How much quicker it gets investors to their goal
➕ When it wouldn't make sense to do it

If you’ve been sitting on equity and wondering what to do next, this behind-the-scenes breakdown will help you figure out if a cash out refi could work for you!

Listen NOW!

Chapters:

00:00 Cash-Out Refi & “Property Babies” — What We’re Building Today
01:33 Welcome to Not Your Average Investor Show + Why This Topic Matters
02:25 The Equity Fear Factor: When to Harvest Without Killing Cash Flow
03:10 Tool Tease + Live Case Study Setup (Pablo’s Portfolio)
05:02 Quick Housekeeping: Summit Update + Important Disclaimer
05:55 Pablo’s 3-Property Origin Story (2021–2022) & Funding Moves
07:07 Profit Breakdown: Appreciation, Paydown, Tax Savings & Cash Flow Reality
08:37 Eviction, Vacancy, and the Long Game: Staying Invested Through Pain Points
13:01 Pac-Man Principle: Why Appreciation Dominates the “Profit Pie”
14:48 Introducing the Passive Income Planning Tool (Beyond a Profit Snapshot)
16:15 Setting the Target: $10K/Month Net in 15 Years — Why It Matters
18:18 Phases of the Plan: Acquisitions → Debt Paydown → Distribution
20:34 Current Snapshot: $366/mo, $270K Equity, and 43% of Acquisitions Done
23:23 If You Do Nothing: 15-Year Projection for Income and Equity Growth
24:29 Delivering the Next Property Baby: How Much Cash You Need ($60–$75K)
27:55 15-Year Upside: Cashflow Growth + Massive Equity Gains
28:54 “Go Find the Money”: Cash-Out Refi Options & Portfolio Cashflow Impact
32:05 Which Properties to Refinance? Protecting Low Rates & Picking the Winner
35:49 New Passive Income Plan: 4 Properties, Small Cashflow Trade-Off, Big Long-Term Win
39:03 Is $63K Enough to Buy Another Rental? Down Payment Targets & Inventory Fit
40:00 Small vs Big Homes Debate: Appreciation, Neighborhood Cycles & Workforce Housing
45:31 Live Q&A: HELOC vs Refi, Taxes/Insurance Included, and Using Primary Home Equity
49:27 Summit Next Steps + Community Updates (C3X, Greg Roberts, Karaoke)
54:18 Final Wrap: Summit Logistics & “Don’t Be Average” Send-Off

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