Not Your Average Investor Show

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...

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 decisi...

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 whe...

It’s been years in the making, and now Jacksonville’s urban core is on the cusp of something big: 10,000 downtown residents.

This week on Not Your Average Show, JWB Co-Founder Gregg Cohen and show host Pablo Gonzalez break down the newly released State of Downtown Report and explain what this milestone means for investors and the future of the city.

With nearly 9,000 residents already downtown and a 31% population surge since 2020, the long-talked-about “24-hour city” is finally becoming a reality.

Here’s what we’re diving into:
✅ Why 10,000 is more than just a number and h...

The real estate market is entering 2026, and many investors are trying to make the right move.

And when things feel unclear, it’s easy to get distracted by headlines or make decisions that drift away from long-term goals.

That’s why this week, we’re taking you inside JWB Real Estate Capital’s annual “State of the Union.”

In this special episode of the Not Your Average Investor Show, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez walk you through how JWB reviews performance, filters noise from signal, and builds a strategy rooted in real data...

Big headlines make it sound like housing is about to change overnight — but will it?

In this episode of the Not Your Average Investor Show, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez break down two major headlines: 

President Trump’s proposed “Wall Street ban” on single-family rentals, and the historic move directing the GSEs to buy $200B of mortgage-backed securities.

They’ll explore:
- The real share institutional investors have in single-family homes
- How a proposed ban would actually affect affordability and supply
- What the $200B MBS move signal...

One of the great things about rental properties is that they often lead to more rental properties without needing additional capital- what we call "rental property babies"-

PLUS if you bought a rental property a few years ago, there’s a good chance you already have what you need to have one of these new babies!

The problem is that opportunity doesn’t always show up clearly on a spreadsheet.

That’s why on this episode of the Not Your Average Investor Show, we’re bringing on JWB client, Sarann Jennings, who recently...

Every year, we set aside one show to turn the spotlight where it belongs: on our community.

This Upcoming Show is a celebration of the people who show up week after week, tune in, ask great questions, and actually apply what they’re learning along the way.

And on this show… we won’t be the ones sharing the lessons.

Instead, members of our investor community will join us live to reflect on the past year and share the real takeaways that stuck with them; the ideas, conversations, and moments from the show that c...

Real estate investing is full of numbers you can verify.

But the part investors struggle with is simpler:

Who are the people behind this? And can they actually run the play for the next 10 years?

In this episode, we share how JWB builds a team that consistently executes — from the way we recruit and hire, to the culture we protect, to the incentives we align so outcomes stay strong for investors. Join our host, Pablo Gonzalez, and SHRM-CP–certified HR professional at JWB, Laura McLogan.

This is a behind-the-scenes look at what...

Planning season is here, and this year, the community gets a behind-the-scenes look at how JWB shapes its strategy long before the predictions go public. In this episode, host Pablo Gonzalez sits down with JWB Co-Founder Gregg Cohen and President Alex Sifakis to walk through how JWB plans for the future — live from the new JWB building in Downtown Jacksonville!

This episode explores the internal process: how the leadership team interprets early signals, how conversations evolve, where debates sharpen the vision, and how today’s approach differs from the early “good old days.” With Gregg and Alex together...

Mortgage headlines are loud again. Between talk of 50-year mortgages, the FHFA revisiting assumable and portable loans, and lenders raising questions about feasibility, there’s a lot of noise on how this will affect the housing market, but few are talking about what this means for investors, specifically.

In this week’s Not Your Average Insights, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez break down what is happening and add the investor's perspective.

They’ll unpack:
- Why 50-year mortgages look different from an investor’s perspective, and may be a momentary opportunity you need...

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

Here's what we'll discuss:

* Current Jacksonville real estate market pricing, rents, and months of inventory (MOI)
* Learn why Jacksonville's current home pricing represents an opportunity for higher future home price appreciation
* See how Jacksonville's 2025 home sales volume compares to 2024 - and what this means as far as pricing stability and future growth
* JWB's predictions for the 2026 Jacksonville real estate market

You won't want to miss this opportunity to...

Everyone’s watching the latest rate cut, mortgage headlines, and Fed press conferences… but most investors are missing the real policy shift that could reshape the housing market.

In this week’s Not Your Average Insights, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez break down why the end of Quantitative Tightening (QT) on December 1 may be the single most important signal for investors right now, even more influential than rate cuts or inflation updates.

They’ll unpack:
- Why the Fed ending QT could push mortgage rates even lower and what that means for affo...

Headlines love to say real estate has never been less affordable — but is that actually true?

In this episode of the Not Your Average Investor Show, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez take a look back in time to compare housing affordability in 1982 vs. 2025 and the results might surprise you.

They’ll unpack:

- Why 1982 was actually less affordable than today - even with lower home prices
- How interest rates, incomes, and homeownership are actually creating a good buying opportunity right now
- What this history lesson reveals abou...

A lot of investors are buzzing about the newest tax bill, but very few truly understand how these updates impact Bonus Depreciation, Cost Segregation, and long-term rental property savings.

So this week on the Not Your Average Investor Show, we’re bringing in tax expert Bryan Reyes to break down what changed, what it means, and how you can use it to your advantage.

Join co-founder of JWB Real Estate Capital, Gregg Cohen, and CPA and Tax Partner at Pivot CPAs, Bryan Reyes, to learn:

✅ Why the extensions to Bonus Depreciation, QBI, and SALT...

You’ve got a few property tabs open. The photos look good. The numbers are in the range you were hoping for. On paper, any one of them could work, but choosing the one that actually fits your long-term plan? That’s where most people hit pause.

If that moment feels familiar, you’re not the only one. The best investors don’t pick properties by gut feeling or guesswork; they follow a clear process.

In this live session, Gregg Cohen (co-founder of JWB Real Estate Capital) will walk through a real decision scenario using JWB’s Po...

You’ve heard the strategies. You’ve seen the data. But what does it actually look like to build a rental property portfolio that fits your life, your goals, and your timeline?

On this episode of the Not Your Average Investor Show, we sit down with a JWB client, Mike Foster, to walk through his real investing journey of how he shaped a plan that aligned with his long-term vision, what the experience has been like so far, and how working with JWB helped him move forward with clarity and confidence.

Join show host, Pablo Gonz...

Property taxes have become one of the biggest talking points for investors.
Rates are rising, and for many, it feels like a growing burden that’s eating into returns.

But what if these increases actually signal strength in your investment?

On this week’s episode of the Not Your Average Investor Show, Pablo sits down with Hannah Feran, Portfolio Management Supervisor at JWB, to unpack what’s really driving property taxes higher and what it means for long-term investors.

You’ll learn:
- Why higher property taxes often track rising home values a...

Headlines are buzzing about government shutdown, shifting interest rates, and all time highs for gold, but what do those stories actually mean for real estate investors?

In this week’s Not Your Average Insights, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez look beyond the politics and into the data to reveal how these macro events really shape the housing market.

They’ll unpack:

- What history tells us about how past government shutdowns affected prices, rents, and new construction
- Why the concurrent all time highs of gold prices and the stoc...

It’s official: Publix is opening a 31,000-square-foot store in Downtown Jacksonville’s Pearl Square, part of Gateway Jax’s $2 billion redevelopment plan. On the surface, it may look like just another grocery store opening, but for investors it is a powerful signal that downtown has reached its tipping point.

In this episode of the Not Your Average Investor Show, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez will break down why this milestone is much bigger than it seems.

You’ll learn:

- Why grocery stores are considered anchor tenants in every major do...

Many investors are noticing that rental property cash flows are looking stronger right now but what’s actually driving that improvement?

In this Portfolio of the Month episode, JWB Co-Founder Gregg Cohen and host Pablo Gonzalez will walk through a real investor portfolio live on the show and unpack how current market conditions are creating stronger-than-expected cash flow.

They’ll talk through:

- How today’s property pricing and interest rates are affecting returns
- What role JWB’s incentives play in boosting cash flow (and how it actually works)
- A transp...

The number one thing we hear is: “I want to grow my portfolio… but I need more capital.”  Our answer?  Capital and cash flow are the easiest part.  De-risking the experience is the hard part

That's what JWB's approach to rental property investing and Tardus Wealth Strategies income Snowball have in common.  They are uncommon approaches to systematic wealth creation.

That's why we're bringing the CEO of Tardus (and author of Creating Your Income Snowball), Tanisha Souza, on the Not Your Average Investor Show to share the innovative way she's developed to raise capital for real estat...

The Fed just cut interest rates, and that's a clear signal that change is coming for real estate investors. Lower rates should lead to more cash flow and better buying power.

But there’s still a lot of confusion about what happens next.

Just one day after the Fed’s announcement, 30-year mortgage rates actually went up. That doesn’t mean the Fed's move won’t work—it just means the mechanics of the market take time, and most people don’t understand how this all plays out.

That’s why this week on the Not You...

Join us for the Q4 2025 Jacksonville Real Estate Market Outlook by JWB. We'll be joined by Gregg Cohen, Co-Founder of JWB Real Estate Capital.

Here's what we'll discuss:

* Current Jacksonville real estate market pricing, rents, and months of inventory (MOI)
* Key trends and updates impacting the Jacksonville market
* JWB company stats and Key Performance Indicators

You won't want to miss this opportunity to spend some time with one of JWB's owners and learn more about how you can take advantage of the Jacksonville real estate market. Hope to see you there!<...

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.<...

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 esta...

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 actu...

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 s...

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 buil...

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
•⁠ ...

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 Jacksonvil...

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...

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 tran...

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...

Curious what’s ahead for real estate in the second half of 2025? The experts are weighing in, and we’re breaking it all down.

In this episode, JWB Co-Founder Gregg Cohen joins Pablo Gonzalez to react to the top national forecasts from Fannie Mae, NAR, Zillow, and others. They’ll explain what these predictions mean for rental property investors like you.

We’ll unpack:

- Which predictions matter (and which ones miss the mark)
- What could happen with interest rates, prices, and rent growth
- Why Jacksonville could outperform again in a tig...

There’s one question we hear from every new investor: “How do I know which rental property is the right one for me?”

On this episode of the Not Your Average Investor Show, we’re going to answer that question the same way we do on real sales calls by walking you through the process we use to help investors build portfolios that match their goals.

Join JWB Co-Founder, Gregg Cohen, and show host, Pablo Gonzalez, as they break it down:

- The three things you must know before picking a property (goals, resource...

Join us for JWB’s Q2/Q3 2025 Jacksonville Real Estate Market Update. We'll be joined by Gregg Cohen, Co-Founder of JWB Real Estate Capital.

Here's what we'll discuss:

* Current Jacksonville real estate market pricing, rents, and months of inventory (MOI)
* Key trends and updates impacting the Jacksonville market
* JWB company stats and Key Performance Indicators

You won't want to miss this opportunity to spend some time with one of JWB's owners and learn more about how you can take advantage of the Jacksonville real estate market. 

Listen NOW!

C...

Most investors think their retirement accounts are off-limits for real estate—but they’re missing a huge opportunity.

That’s why this week’s episode of the Not Your Average Investor Show is all about how to use 401(k)s and IRAs to build your rental property portfolio—without triggering penalties or unnecessary risk.

Join JWB co-founder, Gregg Cohen, and show host, Pablo Gonzalez, as they break down:

✅ What you need to know about buying real estate INSIDE your IRA or 401k
✅ The biggest mistakes investors make when trying to use retirement funds for real...

You'd be surprised to hear how many people can afford to invest in rentals, but don't- just because they don't have a clear vision of how to grow from there.

But here's what most don't realize- 

The key to portfolio growth isn't how much extra income you have.  
The key is having the right strategy for your income. 

That's why week on the Not Your Average Investor Show, Gregg Cohen (co-founder of JWB Real Estate Capital) and show host Pablo Gonzalez show host break down exactly how passive investors can go from one...

Ever wonder how experienced investors actually decide which rental property to buy?

Most people start by browsing listings—but that’s not how the pros build long-term wealth.

That’s why we’re giving you a behind-the-scenes look at how JWB matches you with the right property—after creating a strategy around your budget, cash flow goals, and return expectations.

On this week’s Not Your Average Investor Show, JWB co-founder Gregg Cohen and show host Pablo Gonzalez will walk you through:

✅ How to use JWB’s Portfolio Generator to sort and narrow prope...