Commercially Speaking Podcast- Commercial Real Estate Investing That Entertains

Most founders don’t hire an executive assistant for one simple reason:

They think it will create more work.

More training.

More managing.

More explaining.

But what if the opposite is true?

In this episode, we bring in Terry Pham to break down the real reason founders stay stuck—and how delegation actually works when it’s done right.

We cover:

• The 5 delegation roadblocks holding founders back
• Why “I don’t have time” is the biggest lie
• How...

If your business isn’t working… it might not be your hustle.

It might be what you’re missing.

In this episode of Commercially Speaking, we sit down with Tommy Martin of the Tebow Group to break down why even smart, driven entrepreneurs fail—and the framework that finally changed everything.

After 3 failed businesses, Tommy discovered that success isn’t about working harder… it’s about having the right structure.

We dive into:

• The 5-...

Artificial intelligence can:

• Underwrite• Model• Analyze• Draft• Summarize• Prospect• Automate follow-up

Faster than most brokers.

This isn’t about average producers.

This isn’t about junior analysts.

This is about the brokerage model itself.

If AI removes information asymmetry, compresses labor, and accelerates execution… what’s left?

In this episode, we explore whether brokerage as we know it survives this decade.

Not softer.Not ...

How do you close 2,500+ commercial real estate deals?

In this episode of Commercially Speaking, we sit down with Gary Martinez, CCIM, SIOR, industrial specialist, CI 102 instructor, and one of the most respected brokers in Southern California.

Gary shares:

• How he went from property manager to top 1% broker
• Why specializing changed his income trajectory
• The difference between fighting for business vs fighting for relationships
• The “Kn...

What do billion-dollar investors and donors actually care about?

It’s not your pitch deck.

It’s not your financial model.

And it’s definitely not your IRR slide.

In this episode of Commercially Speaking, we sit down with Greg Dugard, COO of Seder Grove Holdings, who previously helped raise over $5 billion during Notre Dame’s historic capital campaign.

Greg breaks down what he learned from raising billions, working with ultra-high-net-wo...

If you sell an investment property and want to defer taxes, a 1031 exchange is usually the answer.

But there’s a problem no one likes to talk about:

You only have 45 days to identify a replacement property.

That pressure often leads investors to overpay, settle for deals they don’t love, or rush into more active management when they were actually trying to slow down.

In this episode of Commercially Speaking, we sit down with Taylor Ash...

You built the business.

The money showed up.

And suddenly you’re asking the questions no one warned you about:

Where do I put this money?

How do I make sure it actually lasts?

In this episode of Commercially Speaking, we sit down with Garrett Gatton, founder of Reinvest Capital, to talk about what comes after success.

Garrett works with business owners who’ve already “won” and are now trying to steward capital wisely, buy back time, and ...

Why do modern neighborhoods feel disconnected, car-dependent, and soulless?

In this episode of Commercially Speaking, we sit down with Austin Tunnell, founder of Building Culture, to talk about real estate development, walkable communities, architecture, and how the built environment shapes human behavior.

Austin shares his journey from Big 4 accounting at KPMG to quitting everything, traveling Europe, joining the Peace Corps, learni...

Happy Thanksgiving to all! We are so thankful for every one of you for giving us your eyes and ears for 124 episodes! We will be back in January with bigger guests, wider topics and the same brotherly chemistry.

Bo and Timmy relive the last couple months starting with last weekend’s annual chainsaw weekend. The Barron boys join their dad at the cabin to prepare wood for the winter.

Timmy talks about what it was like to emcee the CCIM...

If you want to understand data centers, the power grid crisis, and the real estate race behind the future of AI — this is the episode.

Today on Commercially Speaking, we sit down with Simon Enwia, CCIM — a multi-state broker, tech-driven developer, and one of the few people specializing in data center development sites. And what he reveals is wild:

Here’s what you’ll learn in this episode:

• Why data center vacancy is below 1% natio...

She built a coaching company, wrote a book in four days, and raises seven kids—Mary Katherine Wathen is redefining what it means to lead a meaningful, integrated life. In this live studio episode, she joins Bo and Timmy to talk executive coaching, identity, leadership burnout, humility at the top, and how to live authentically at work, at home, and everywhere in between.

💥 Whether you're a burned-out broker or a high-achieving ...

In this bonus episode of Commercially Speaking, Bo and Timmy welcome Luke Morris, co-founder of Crexi and Capitalize. They discuss Luke's journey in commercial real estate, the evolution of Crexi, and the launch of Capitalize, a platform designed to streamline commercial real estate financing using AI. The conversation delves into the challenges faced by brokers and lenders, the importance of data in the industry, and the future pr...

Can your retirement account buy real estate? Startups? Alpaca farms?! Yes. And in this episode, Dana Udumulla from Madison Trust breaks down how self-directed IRAs actually work, what they can (and can’t) invest in, and why more commercial real estate investors should be using them to raise capital.

Whether you're an accredited investor or a confused podcast co-host (cough Timmy), this conversation is packed with practical takea...

Chuck Welden doesn’t just talk real estate — he lives it.

He’s a landlord, developer, and manager who still picks up trash on his own properties. In this episode, Chuck brings the heat (and the humor), breaking down:

🔹 The dangerous illusion of scale

🔹 What “boots on the ground” really looks like

🔹 Why managing properties makes you a better developer

🔹 The mindset most brokers will never get

🔹 Why being “dumb” might be your biggest ...

What do top brokers really look at when evaluating a market?

In this episode, we sit down with Anthony Humphress, a commercial real estate powerhouse out of Lexington, KY, to unpack what makes a secondary market thrive — and the blind spots brokers often miss.

We dive into:

🔹 Why Lexington is outperforming much larger markets

🔹 Anthony’s tenant-focused approach to brokerage

🔹 How to think like a strategist, not a tour guide

🔹 The rea...

What does 40 years in commercial real estate teach you?

In this episode, we sit down with Allen Buchanan — one of the most respected veterans in brokerage — to talk about the habits, mistakes, and mindset that make or break a CRE career.

We dig into:

🔹 The #1 mistake brokers still make today

🔹 Why talking yourself out of the deal beats short-term wins

🔹 The ingredients of an elite broker

🔹 The secret to networking

🔹 His advice for th...

What if the most stable real estate investment wasn’t buildings…

It was land?

In this episode, we sit down with Quinn McArthur, a land investor who quietly built a business that offers nearly guaranteed 10% returns — all while working from anywhere and skipping the headaches of tenants, toilets, or debt.

We dive into:

🔹 How his land business works (and why it’s so stable)

🔹 The software tools that make it scale

🔹 Why risk-adjusted ret...

Everyone talks about building wealth through real estate.

Whitney Elkins-Hutten actually does it.

As the Director of Investor Education at PassiveInvesting.com, Whitney has helped guide more than $800M in assets under management — and in this episode, she breaks down how passive investing actually works, who it’s for, and why so many brokers miss the bigger wealth picture.

We cover:

🔹 Why being a GP isn’t always the smartest path

🔹 Ho...

What if your best CRE hire was already in your toolkit… and you were barely using it?

This week we’re joined by Ben Wilson, the guy who trains the instructors who teach brokers how to use Site To Do Business (STDB) — the most powerful (and most underused) platform in commercial real estate.

We dig into:

🔹 The biggest mistakes brokers make with STDB

🔹 How to use trade areas, drive times & custom maps to win business

🔹 Real-life ca...