
Advertise on podcast: Commercially Speaking Podcast- Commercial Real Estate Investing That Entertains
Rating
5from
This podcast has
138 episodes
Language
EnglishPublisher
Bo Barron, CCIM | Timmy Barron, ADHDExplicit
No
Date created
2023/04/04
Latest episode
2026/02/03
Average duration
81 min.
Release period
12 days
Description
Commercial Real Estate investing has never been so entertaining. Hosted by two brothers, Bo, the eldest, is a CCIM instructor, CRE expert, CEO of Barron Commercial Group and Marine. Timmy, the MUCH younger one, is an improv comedian, award winning actor, and coach with ADHD who, “commercially speaking” is an idiot. With Bo’s gift for teaching, he breaks down complex concepts in a way that’s easy for anyone to understand, while Timmy tests that theory. Whether you’re a seasoned pro, investor, user of space or newbie to the world of Commercial Real Estate, this podcast was made for you!
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DST vs 1031: The Tax-Deferred Option No One Explains | With Taylor Ashland
2026/02/03
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 Ashland, founder of Ashland Pacific, to explore Delaware Statutory Trusts (DSTs) as a 1031-eligible alternative.
DSTs allow investors to:
Defer capital gains and depreciation recapture taxesInvest passively in institutional-quality real estateAvoid the 45-day scramble to identify a propertyEliminate active management and tenant headachesWe break down:
How DSTs actually work inside a 1031 exchangeWhy the 45-day window creates bad incentivesWhen a DST makes sense (and when it doesn’t)Loss of control, lack of liquidity, and real risksHow DSTs can be a full exit strategy or a “supporting actor”Why brokers don’t get paid on DSTs (and why that matters)The emotional side of money, taxes, and decision-makingThis episode is not tax or legal advice. It’s a practical, honest conversation about options most investors don’t hear until it’s too late.
The information discussed in this podcast is for informational purposes only and does not constitute investment advice or an offer to buy or sell any securities. Investing in real estate and 1031 exchange replacement properties may not be suitable for all investors and may involve significant risks. All opinions expressed are those of the speaker and are subject to change without notice. Listeners should consult their own financial professionals before making any investment decisions. Ashland Pacific is a branch office of DFPG Investments, LLC. Securities offered through DFPG Investments, LLC. Member FINRA/SIPC. Investment Advisory Services offered through Diversify Advisory Services, LLC. Ashland Pacific is not affiliated with DFPG or Diversify.
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://cre-investor-coach.mykajabi.com/a/2148133410/9YMWzNXy🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking🎧 Learn more about Taylor:
https://shepherdingyourwealth.comhttps://ashpac.comInstagram: @taylordesmondashland📺 Subscribe for more conversations on real estate, investing, negotiation, and buying back your time.
And yes, Barbara Corcoran… still standing by.
00:00 – The 45-Day Problem With 1031 Exchanges
Why rushed timelines force bad decisions
05:30 – Why Investors Overpay in 1031s
Incentives brokers love and sellers hate
10:40 – What Is a Delaware Statutory Trust (DST)?
Plain-English explanation
18:30 – How DSTs Qualify for 1031 Exchanges
Beneficial interests, not partnerships
27:00 – Passive Real Estate Without Management
No tenants, no toilets, no calls
34:45 – Loss of Control & Liquidity (The Real Risks)
Why DSTs are not for everyone
42:20 – Using DSTs as a Supporting Actor
Solving “boot,” debt replacement, and leftover equity
52:10 – Why Brokers Don’t Get Paid on DSTs
The incentives nobody explains
01:01:30 – Emotional Decision-Making in Investing
Why numbers alone aren’t enough
01:12:00 – Who a DST Is Actually For
Ideal scenarios and red flags
01:22:30 – Final Takeaways
More options, better decisions
You Won. Now What? The Money Problems No One Prepares You For | with Garrett Gatton
2026/01/27
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 build wealth that doesn’t wreck their life or their family.
This conversation dives into:
Why success often creates more complexity, not lessThe difference between being safe with money and being wisePassive real estate investing vs active distractionBuying back time instead of stacking more responsibilityFaith, stewardship, and purpose without sacrificing returnsWhy unmanaged money becomes anxiety with better snacksHow legacy thinking changes every financial decisionAI, executive assistants, and scaling your impact without burning outThe future of housing, including Ohio’s first 3D-printed concrete homeIf you’ve ever thought, “I did the hard part… now what?”
This episode is for you.
🎧 Follow Garrett:
Reinvest Capital: https://www.reinvestcapital.usRE:Invest Podcast https://reinvestpodcast.buzzsprout.com/LinkedIn: Garrett Gatton📺 Subscribe for more conversations on real estate, leadership, money, and meaning.
And Barbara Corcoran… we remain respectfully available.
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://cre-investor-coach.mykajabi.com/a/2148133410/9YMWzNXy🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking
00:00 – You Won. Now What?
When success creates new problems no one talks about
02:30 – When Money Stops Feeling Like a Win
Why unmanaged wealth becomes anxiety
06:00 – Stewardship vs Wealth Creation
Why growing money and using it wisely are different skills
10:00 – From Ministry to Investing
How Garrett’s background shaped his view of capital
15:30 – The Hidden Problem With Active Investing
Why entrepreneurs accidentally buy themselves more work
20:45 – Buying Back Time
How passive investing restores freedom
27:00 – Faith, Business, and Excellence
Why purpose doesn’t mean lower returns
34:30 – Executive Assistants + AI
The real way to scale impact without burning out
44:00 – Safety vs Wisdom With Money
Why “playing it safe” can quietly cost you everything
55:30 – Legacy Thinking
The question every successful founder asks too late
01:08:00 – The Future of Housing
3D-printed concrete homes and what’s coming next
01:15:00 – Final Takeaway
What success is actually supposed to buy you
Modern Neighborhoods Were Designed To Make Us Lonely. The Solution Is Simple.
2026/01/20
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, learning traditional building by hand, and becoming a developer focused on creating beautiful, human-scale neighborhoods.
This episode covers:
Walkable neighborhood design vs suburban sprawlWhy modern architecture lost beauty and durabilityMixed-use development, community-centered design, and urban planningHow zoning laws and incentives shaped American suburbsReal estate development with values-aligned investorsWhy efficiency alone is hurting cities and communitiesHow buildings influence culture, behavior, and belongingIf you’re interested in real estate investing, urban planning, architecture, community development, or building better neighborhoods, this conversation will change how you see cities forever.
🎧 Listen to the full episode on YouTube, Spotify, and Apple Podcasts
📺 Subscribe for more conversations on real estate, leadership, and culture
Get Your EA Today with our friends at Super Powers: Superpowershq.com/commerciallyspeaking
Austin Tunnell
X / Twitter: https://x.com/austintunnellLinkedIn: https://www.linkedin.com/in/austintunnellBuilding Culture
Building Culture Podcast: https://buildingculture.com/podcastRecommended Books
Suburban NationWorks by Christopher AlexanderWorks by Léon KrierOrganizations & Resources
Congress for the New Urbanism (CNU)
https://www.cnu.org
Strong Towns
https://www.strongtowns.org
Urban Land Institute (ULI)
https://uli.org
⏱️ Chapters
00:00 – Why Modern Neighborhoods Feel Broken
Car-dependent suburbs, isolation, and what’s missing from American communities
04:30 – From KPMG Accountant to Quitting Everything
Austin’s Big 4 burnout, depression, and decision to walk away
09:20 – Traveling Europe & Discovering What America Lost
Spain, Portugal, and the architecture that changed everything
13:30 – Learning Traditional Building by Hand
Laying brick, timber framing, and why craftsmanship matters
17:50 – Buildings Shape People (Not the Other Way Around)
Why the built environment is the human habitat
22:30 – Why Beauty Disappeared from Architecture
Efficiency, zoning, and post-WWII suburban development
27:10 – Walkable Neighborhood Design Explained
Mixed-use housing, density done right, and human-scale communities
32:20 – What Makes a Great Neighborhood
Sidewalks, front porches, parks, local businesses, and community spaces
38:00 – Why Suburban Sprawl Is Financially Broken
Infrastructure costs, declining property values, and unsustainable growth
44:30 – The Culture Problem Behind Real Estate Development
Demand, incentives, and why consumers share responsibility
50:10 – Hiring, Leadership, and Building Culture as a Company
Values-aligned teams and long-term vision
55:40 – A New Renaissance in American Cities
Lessons from Florence, patronage, and rebuilding beauty
01:01:30 – How to Get Involved & Learn More
Books, organizations, and resources Austin recommends
CCIM Fall Forum, Capital Camp and Chainsaw Weekend | Happy Thanksgiving | CSPod Ep 124
2025/11/27
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 Fall Forum and Bo found a new hobby when attending Capital Camp.
The Data Center Crisis No One Is Talking About — With Simon Enwia, CCIM
2025/11/19
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% nationwideThe reason America will need 2x the power by 2030What makes land “powered land” — and why it’s becoming the new goldThe exact criteria hyperscalers (Amazon, Meta, Google, Oracle) look forWhy data centers are now measured in megawatts per acre, not square footageHow the U.S. is locked in an AI arms race with ChinaThe brutal truth about NIMBY pushback and community approvalsWhy some utilities are charging $250,000+ just to get in line for power studiesThe four things every site absolutely must have:Simon breaks down the economics, the pipeline issues, the insane permitting timelines, and why the next decade of CRE may hinge entirely on data center development.
This is the deep dive on data centers you’ve been looking for.
🔔 Enjoyed the episode? Do these 3 things:
1. Subscribe on YouTube & Spotify
2. Leave a 5-star review on Apple Podcasts
3. Join the newsletter:
👉 subscribe.wgbaron.com
🚀 Build your CRE business faster
Hire a virtual assistant trained specifically for CRE:
👉 superpowershq.com/commerciallyspeaking
🙌 Huge Thanks
A massive thank-you to Simon Enwia, CCIM for breaking down the world of data centers and the future of AI infrastructure.
Email: [email protected]
Real Estate Forum: forum.senw.io
dc.land
00:00:00 - Cold Open00:01:29 - Welcome Simon Enwia, CCIM00:04:34 - Becoming an SIOR Candidate00:06:37 - Welcome to KY Bourbon Lesson by Bo00:11:01 - Getting Into CRE00:13:23 - House Flipping00:17:04 - Creating The First Digital Security for REITS00:19:50 - COVID Hits00:20:33 - The Love Of Deal Making00:21:46 - Licensed In 3 States In 10 Days00:24:16 - Senior Advisor At SVN00:26:52 - Getting A Managing Broker’s License In Multiple States00:29:38 - Building A Tech-Based Brokerage00:34:36 - CCIM is Better Than Real Estate MBA00:40:23 - Never Use Your Network. Provide Value To Your Network00:40:53 - Knakal Affiliate Program00:41:32 - An Inch Wide And A Mile Deep00:43:29 - How To Figure Out What To Specialize In00:47:54 - Fiduciary Responsibility00:52:06 - Cheers, Jesus!00:53:01 - A Good Name Is Worth More Than Gold and Silver00:55:55 - The Incredible Worth Ethic Of Immigrants00:57:47 - Data Centers01:02:30 - 1. Vacancy For Data Centers Is At A Low 1%01:03:12 - 2. There Is Not Nearly Enough Power (Will Need Double By 2030)01:05:19 - Bill Gates On Climate Change01:07:23 - 3. There Is An AI Race!01:09:55 - How Important Is Taiwan Right Now?01:14:21 - The Ideal Data Center Property01:17:39 - How Much Power a Hyper Scaler Needs! (Meta, OpenAI etc)01:18:34 - Quantifying The Power Needed01:19:38 - Infrastructure Proximity01:20:43 - The High Cost Of Getting In Line01:21:55 - $200K A Year Software Per User01:22:56 - Several Years To Close01:25:26 - Convincing The Community To Allow A Data Center01:31:48 - Land Size01:33:08 - Water Usage01:34:08 - Fiber and Redundancy01:36:37 - Leasing a Humanoid Robot01:39:41 - Behind The Meter (What’s Not Connected To The Grid)01:40:33 - Becoming The Knakal Of Data Centers01:42:35 - [email protected], dc.land01:43:09 - Simon Is Hiring01:44:19 - Pop Quiz02:03:25 - forum.senw.io02:04:04 - Outro
The Executive Coach Your Favorite CEO Is Probably Hiding | with Mary Katherine Wathen
2025/11/11
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 exec wondering, “Is this it?”—this episode is your wake-up call.
📚 Book: Made for More https://a.co/d/5ca0QfV
🌐 westofperfection.com
#Leadership #Coaching #CommerciallySpeaking #CRE #ExecutiveCoaching #MaryKatherineWathen
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl🛠️ **Site to Do Business (STDB) – Powerful CRE analysis and mapping tools: stdb.com🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking📊 CRE Marketing Mastermind – wesgay.com/csResources Mentioned In This Episode
📚 Book: Made for More https://a.co/d/5ca0QfV🌐 westofperfection.com📰 Our Weekly Newsletter: The Inside Scoop On CRE — https://subscribe.wgbarron.com🏬 Barron Commercial Group: CRE Made Simple — https://barroncommercial.com/🥏 All Disc, No Balls! Tizbee, The Secret Game Of Champions — https://tizbee.com
Transforming Commercial Real Estate with Technology | The Birth of Crexi
2025/11/04
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 prospects for Capitalize. Luke emphasizes the need for transparency and trust in commercial real estate, highlighting how technology can empower brokers to better serve their clients.
Chapters
00:00 Introduction to the Podcast and Guest
02:40 Luke Morris: Early Life and Career Path
05:19 The Birth of Crexie: Innovations in Commercial Real Estate
08:00 The Evolution of Crexie: Growth and Milestones
10:48 Identifying Pain Points in Commercial Real Estate
13:32 Capitalize: The Next Step in PropTech
16:25 Understanding Capitalize's Functionality and Market Impact
19:07 Use Cases for Brokers: Enhancing Efficiency and Effectiveness
21:56 The Role of Brokers in Commercial Real Estate
24:34 Exploring the Technology Behind Capitalize
27:27 Real-Time Insights and Market Dynamics
30:28 Conclusion and Future Outlook
33:22 Understanding Mezzanine Debt and Preferred Equity
36:51 Navigating Fund Management and Deal Sponsorship
39:28 Challenges in Data Aggregation and AI Integration
44:08 Personal Insights and Hobbies of Luke Morris
48:52 Engagement and Future Steps for Capitalize.io
How to Use Self-Directed IRAs to Invest in Real Estate (and Alpacas) | with Dana Udumulla
2025/10/28
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 takeaways, tax strategies, and jaw-dropping scenarios (like turning $7K/year into $4.75M tax-free).
We also get into:
Roth vs Traditional IRA pros & consCommon mistakes investors make (and how to avoid getting disqualified)How to structure deals to receive retirement dollarsReal estate, bonus depreciation, and... Brazilian sugar?Don’t invest another dollar until you listen. Your future self will thank you.
📈 Sponsored by: Site to Do Business (STDB.com) and CRE Investor Coach
🎯 Learn more: MadisonTrust.com
👇 Subscribe + rate us if you learned something new!
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl🛠️ **Site to Do Business (STDB) – Powerful CRE analysis and mapping tools: stdb.com🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking📊 CRE Marketing Mastermind – wesgay.com/csResources Mentioned In This Episode
📰 Our Weekly Newsletter: The Inside Scoop On CRE — https://subscribe.wgbarron.com🏬 Barron Commercial Group: CRE Made Simple — https://barroncommercial.com/🥏 All Disc, No Balls! Tizbee, The Secret Game Of Champions — https://tizbee.com00:00:00 – Welcome to Commercially Speaking (and IRR is NOT a pirate noise)00:00:42 – Meet Dana Kudumula: IRA Whisperer & Queen of Custodians00:02:51 – Legal Disclaimer: No Financial Advice, Just Vibes00:04:42 – What Even Is a Self-Directed IRA?00:06:45 – Dana’s Origin Story: $200, Wall Street, and Finding Her Passion00:08:11 – “You Can Invest in WHAT?!” – Real IRA Examples00:10:05 – Roth vs Traditional IRAs Explained00:14:33 – A $400K Tax-Free Growth Scenario00:16:01 – Can You Use Bonus Depreciation in an IRA?00:19:27 – Can a Fund Accept Self-Directed IRA Capital?00:21:48 – What Happens to “Wasted” Depreciation?00:24:42 – The Real Estate Pro Tax Strategy Breakdown00:26:26 – Can You Roll Over Any Retirement Account?00:29:15 – Setting Up a Self-Directed IRA (Step-by-Step)00:32:54 – Who Legally Owns the Asset? It’s Not You!00:33:46 – What Happens to Rental Income?00:34:42 – The Checkbook Control Model00:36:07 – Reminder: It’s Still a Retirement Account00:37:13 – When Can You Take Distributions?00:38:41 – How Much Can You Contribute? (And For Your Kids Too!)00:41:00 – How $7K/Yr Becomes $4.75M – Compound Interest 10100:44:22 – Roth vs Traditional: The Contribution Tradeoff00:45:21 – Yes, Kids Can Have Self-Directed IRAs Too00:46:45 – What Can’t You Do With a Self-Directed IRA?00:48:09 – Creative Legal Loopholes (But Don’t Try These at Home)00:50:22 – Lending to Family: Who’s Disqualified?00:52:13 – Mistakes That Kill Your IRA (Seriously)00:56:05 – The Biggest Scam Red Flags (And How to Vet Deals)00:58:52 – Know Your Risk Profile: Don’t YOLO Retirement Funds01:00:42 – Capital Raising From IRAs: A Hidden Superpower01:03:28 – The $44 Trillion Opportunity01:04:52 – Timmy’s Misconception: “Isn’t There a Menu of Investments?”01:07:16 – Why Financial Advisors Don’t Talk About This01:08:40 – Timmy & Dana Bond Over February Birthdays01:09:10 – Most Common IRA Scams (And the Power of Pause)01:12:02 – The Importance of Trusted Communities01:13:30 – Final Takeaway: Research, Pause, and Diversify
Why Chuck Welden Says CRE is for Idiots (And Why He Might Be Right)
2025/10/21
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 asset in CRE
This one is funny, wise, and brutally honest — don’t miss it.
🎙 Hosted by Timmy & Bo Barron
📺 Subscribe for more: youtube.com/@commerciallyspeaking
📩 Get exclusive updates: subscribe.wgbarron.com
#CRE #CommercialRealEstate #Brokerage #LexingtonKY #SecondaryMarkets #TenantStrategy
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl🛠️ **Site to Do Business (STDB) – Powerful CRE analysis and mapping tools: stdb.com🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking📊 CRE Marketing Mastermind – wesgay.com/csResources Mentioned In This Episode
📰 Our Weekly Newsletter: The Inside Scoop On CRE — https://subscribe.wgbarron.com🏬 Barron Commercial Group: CRE Made Simple — https://barroncommercial.com/🥏 All Disc, No Balls! Tizbee, The Secret Game Of Champions — https://tizbee.comChapters👇
00:00 – Chuck Welden: Gators, Leases & Baptisms
00:30 – The Chuck Welden Masterclass Begins
01:08 – Meet Your Hosts (and Confused Cap Rates)
02:04 – Who is Chuck Welden?
03:01 – The Disclaimer Section
04:28 – WWE Meets Sunday Service
05:28 – Chuck’s Business Philosophy & KPIs
07:16 – Commercial Break: CRE Investor Coach & STDB
08:41 – Chuck’s Origin Story
13:34 – How Chuck Blends Business & Kingdom Impact
17:22 – What is Business as Mission?
19:17 – The Power of Relationship at Scale
24:10 – How Christian Principles Help Business
27:07 – What Loving Tenants Actually Looks Like
31:23 – What You Don’t Measure, You Don’t Treasure
35:09 – Love, Truth, and Trash Pickup
39:25 – Creation Care & Conservation in CRE
45:22 – The Triple (or Quadruple) Bottom Line
51:03 – Nobody Cares How Much You Know...
57:15 – Fund 2: What’s Next for Weldon Field
01:00:02 – Social Needs + Cultural Fluency
01:02:59 – The Prayer Walks & Resident Stories
01:07:16 – Connect, Share, Gather, Train
01:10:12 – What Happens After the Sale?
01:13:08 – Chuck’s Challenge to Churches
01:18:03 – Inventory Your Missional Potential
01:24:25 – Who Should We Talk To Next?
01:26:51 – Chuck’s Final Invite + Lions Den Info
01:32:40 – Outro + Barbara Corcoran Plea
This Is What Separates Good Brokers from Great Ones | with Anthony Humphress
2025/10/14
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 real reason deals fall apart
🔹 Lessons from decades of CRE experience
If you’re a broker, investor, or advisor — this episode will sharpen how you see your market.
🎬 Chapters
00:00 - Intro: Who is Anthony Humphress?
02:45 - How Lexington punches above its weight
08:20 - Anthony’s tenant-first mindset
12:55 - What most brokers get wrong about market analysis
17:30 - How to build trust with tenants and landlords
22:40 - The real reason deals fall apart
27:10 - Lexington’s retail momentum and future outlook
32:05 - Why Anthony loves secondary markets
36:40 - What great brokers do differently
41:15 - Closing thoughts & advice for new brokers
44:20 - Outro
🎙 Hosted by Timmy & Bo Barron
📺 Subscribe for more: youtube.com/@commerciallyspeaking
📩 Get exclusive updates: subscribe.wgbarron.com
#CRE #CommercialRealEstate #Brokerage #LexingtonKY #SecondaryMarkets #TenantStrategy
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl🛠️ **Site to Do Business (STDB) – Powerful CRE analysis and mapping tools: stdb.com🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking📊 CRE Marketing Mastermind – wesgay.com/csResources Mentioned In This Episode
📰 Our Weekly Newsletter: The Inside Scoop On CRE — https://subscribe.wgbarron.com🏬 Barron Commercial Group: CRE Made Simple — https://barroncommercial.com/🥏 All Disc, No Balls! Tizbee, The Secret Game Of Champions — https://tizbee.com
40 Years in CRE: What Brokers STILL Get Wrong | with Allen Buchanan, SIOR
2025/09/30
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 the next generation of brokers
Whether you’re just starting out or leading a team, Allen’s insights will help you sharpen your game and avoid the pitfalls that sink so many others.
🎙 Hosted by Timmy & Bo Barron
📺 Watch more episodes: https://www.youtube.com/@commerciallyspeaking
👤 Connect with Allen Buchanan: @allencbuchanan, [email protected], 714-624-3896
📚 Get Allen’s Book “The Sequence: A Personal Journey and Proven Framework for Commercial Real Estate Brokerage Success”: https://a.co/d/iYzg6K7
#CRE #CommercialRealEstate #Brokerage #CareerAdvice
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl🛠️ **Site to Do Business (STDB) – Powerful CRE analysis and mapping tools: stdb.com🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking📊 CRE Marketing Mastermind – wesgay.com/csResources Mentioned In This Episode
📚 “The Sequence: A Personal Journey and Proven Framework for Commercial Real Estate Brokerage Success”: https://a.co/d/iYzg6K7📰 Our Weekly Newsletter: The Inside Scoop On CRE — https://subscribe.wgbarron.com🏬 Barron Commercial Group: CRE Made Simple — https://barroncommercial.com/🥏 All Disc, No Balls! Tizbee, The Secret Game Of Champions — https://tizbee.com00:00:00 - Cold Open00:01:00 - Welcome Allen Buchanan00:02:55 - The CRE OGs of Twitter00:04:20 - Divorce, Boy Scouts, Baseball and Golf00:09:09 - Interviewing As A Family And Moving To CA00:09:25 - AD: CRE Investor Coach (Link in Shownotes), Site To Do Business https://stdb.com00:10:41 - Interviewing As A Family And Moving To CA00:15:18 - The Ingredients Of An Elite Broker?00:16:13 - The Proper Why00:17:55 - Focus and Put In The Reps00:19:09 - Why Go Through The Brain Damage Of Writing A Book?00:21:16 - Why Your Book Is Worth Reading00:23:33 - What Other Professionals Have The Clients I Want?00:26:56 - The 2008 Minor Economic Setback00:28:50 - Walk Me Through How You Build A Network?00:34:02 - I Want To Understand What You Do So I Can Help You00:36:58 - Transferring Trust (The Referral)00:39:17 - Working Out Loud00:42:39 - The 3 Things You Need To Be Successful On Social Media00:47:45 - AD: Site To Do Business (https://STDB.com)00:48:24 - The Sequence: https://a.co/d/dAHZo5O00:50:54 - Ways To Source Deals00:55:15 - Focused Questioning (Evaluate/Need Assessment)01:02:14 - How Do You Qualify A Lead?01:07:53 - Talk Yourself Out Of The Deal!!01:11:25 - The Superpower Of Specializing01:17:08 - Pop Quiz01:25:00 - Massimo March Madness01:27:54 - Shoutouts!
Why Smart CRE Investors Are Buying Land, Not Buildings | with Quinn McArthur
2025/09/23
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 returns on land outperform most active deals
🔹 How to build a land portfolio with passive investors
🔹 What brokers are missing when they ignore this model
Whether you’re a broker, investor, or someone searching for the most boring, beautiful way to build wealth — this is your sign to start looking at dirt.
🎙 Hosted by Timmy & Bo Barron
📺 More episodes: https://www.youtube.com/@commerciallyspeaking
👤 More on Quinn and Legacy Land Fund: https://www.legacylandfund.com/
#LandInvesting #PassiveIncome #CRE #RealEstateInvesting #CommercialRealEstate
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl🛠️ **Site to Do Business (STDB) – Powerful CRE analysis and mapping tools: stdb.com🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking📊 CRE Marketing Mastermind – wesgay.com/csResources Mentioned In This Episode
👨🏫Legacy Land Fund: https://www.legacylandfund.com/📰 Our Weekly Newsletter: The Inside Scoop On CRE — subscribe.wgbarron.com🏬 Barron Commercial Group: CRE Made Simple — https://barroncommercial.com/🥏 All Disc, No Balls! Tizbee, The Secret Game Of Champions — tizbee.com00:00:00 - Welcome00:03:05 - How Bo and Quinn Met00:04:14 - Quinn’s Unique Onramp Into Commercial Real Estate00:05:46 - The Green Beret’s00:09:51 - Why Timmy Didn’t Join The Military00:11:18 - Quinn’s Real Estate Mentor00:13:53 - AD - CRE Investor Coach (Link in Shownotes), Site To Do Business https://stdb.com00:15:08 - The Lure of Passive Land Investing00:16:19 - The Secret Freedom Of Land Investing00:19:34 - Why Come To You And Not A Traditional Bank or Mortgage Company00:21:10 - An Example Of A Smaller Deal00:22:56 - The Birth Of Legacy Land Fund00:23:48 - How To Get In On This?00:24:59 - Accredited vs Sophisticated Investor - Explained for Timmy00:27:32 - The Legacy Land Fund Model00:31:08 - Testing Timmy’s Understanding So Far00:38:04 - Is it a Stock Market Alternative?00:39:56 - Can You Drip Your Profits Back In?00:41:09 - What’s The Risk?00:43:02 - AD - Site To Do Business (https://STDB.com)00:44:11 - How Has Your Faith Shaped Your Business?00:45:15 - In The Service Of Vets00:46:13 - It’s So Simple, Timmy Understood Quicker Than Bo Did00:48:04 - Being Able To Offer A More Stable Play00:50:20 - What Do The Taxes Look Like?00:53:12 - The Due Diligence On The Other Side Of The Deal.00:57:58 - This Came From My Own Personal Pain Points01:02:48 - Pop Quiz01:15:06 - Outro
How She Built an $800M CRE Portfolio Without Being a Broker | Whitney Elkins-Hutten
2025/09/16
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
🔹 How to vet passive deals (and operators)
🔹 The 3 pillars of long-term investor confidence
🔹 Mistakes LPs make (and how to avoid them)
🔹 Where the best investors put their money next
If you’re a broker, GP, or someone who’s done all the work but not built the wealth — this episode will change how you think.
🎙 Hosted by Timmy & Bo Barron
📺 Watch all episodes: https://www.youtube.com/@commerciallyspeaking
👩💼 More on Whitney: https://www.passiveinvestingwithwhitney.com/ YT: @passiveinvestingdotcom (Passive Investing Made Simple)
#PassiveInvesting #CRE #CommercialRealEstate #RealEstateInvesting #WealthBuilding
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl🛠️ **Site to Do Business (STDB) – Powerful CRE analysis and mapping tools: stdb.com🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking📊 CRE Marketing Mastermind – wesgay.com/csResources Mentioned In This Episode
👨🏫CI102 — https://www.ccim.com/education/ccim-institute-student-tools/find-course?start[date]=&end[date]=&keyword=&sort_bef_combine=default_DESC&title[2756]=2756📰 Our Weekly Newsletter: The Inside Scoop On CRE — subscribe.wgbarron.com🏬 Barron Commercial Group: CRE Made Simple — https://barroncommercial.com/🥏 All Disc, No Balls! Tizbee, The Secret Game Of Champions — tizbee.com00:00:00 - Cold Open00:00:47 - Welcome00:03:46 - You just handed a 25 year old kid $52,000!?00:07:06 - The Scaling Problem of Residential00:08:42 - Active to Passive Income00:10:47 - Explaining Capital Stack for Timmy00:12:44 - AD - CRE Investor Coach (Link in Shownotes), Site To Do Business https://stdb.com00:14:00 - Tell Us About Your First CRE Conference.00:15:17 - Tragedy Strikes00:18:52 - Whitney’s 5 Freedoms00:24:07 - Bo’s 4 Freedoms00:25:24 - How Do You Define Generational Wealth?00:26:04 - Is Generational Wealth A Bad Thing?00:27:35 - Teaching Your Kids About Money00:36:46 - Portfolio Instability00:38:42 - The Problem With So Much Financial Information00:39:09 - P&L vs Balance Sheet00:40:44 - The Strategies To Win The Wealth Game00:42:47 - The Importance Of Tracking Every Cent00:43:44 - How To Get Over The Fear Of Math00:44:46 - People Taking Up My Time00:46:45 - Strategy > Tactic00:48:15 - Create, Keep, Grow, Pass On00:50:17 - One Of The Problems With 1031 Tax Exchange00:51:43 - Understanding Your Goal and Risk Capacity00:53:12 - Ask Yourself The Important Questions00:55:37 - How Do You Want to Feel When We Achieve X?00:59:44 - Is It Hard To Get A Man To Talk About Feeling?01:01:34 - Bo Geeks Out On AI’s Potential To Help Answer These Questions01:03:44 - Put Your Wants Into Containers01:04:58 - Tackle Income Last01:06:11 - Pop Quiz01:13:36 - Connect With Whitney01:16:52 - Like, Comment, Share, Love ya!
The Tool 95% of CRE Pros Don’t Use Right (But Should) | Site To Do Business with Ben Wilson
2025/09/09
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 case studies of deals unlocked through the platform
🔹 The difference between “using it” and using it right
🔹 Tools even CCIMs often miss
If you’ve ever opened STDB and thought “Where do I even start?” — this episode is for you.
🎧 Hosted by Timmy Barron & Bo Barron
📺 Watch more episodes: https://www.youtube.com/@commerciallyspeaking
💡 Learn more about STDB: https://www.stdb.com
#CRE #CCIM #STDB #CommercialRealEstate #BrokerTools
📺 Subscribe for more episodes weekly
🔗 Learn more: subscribe.wgbarron.com
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl🛠️ **Site to Do Business (STDB) – Powerful CRE analysis and mapping tools: stdb.com🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking📊 CRE Marketing Mastermind – wesgay.com/csResources Mentioned In This Episode
👨🏫CI102 — https://www.ccim.com/education/ccim-institute-student-tools/find-course?start[date]=&end[date]=&keyword=&sort_bef_combine=default_DESC&title[2756]=2756📰 Our Weekly Newsletter: The Inside Scoop On CRE — subscribe.wgbarron.com🏬 Barron Commercial Group: CRE Made Simple — https://barroncommercial.com/🥏 All Disc, No Balls! Tizbee, The Secret Game Of Champions — tizbee.com00:00:00 - Cold Open00:01:01 - Welcome00:02:55 - Bo Has A Confession00:04:39 - Why Timmy Love STDB00:05:33 - Who Uses STDB?00:07:23 - How Ben Wilson Fell Into His Role At STDB00:08:16 - What Does It Cost To Access STDB?00:09:20 - AD - CRE Investor Coach (https://bit.ly/43t6Vrl), Site To Do Business https://stdb.com00:10:35 - Bo Presents The Scenario For Our Demo00:12:52 - Looking At The Top Performing Locations of COhatch00:14:54 - Searching Within a 3 min Drive Time00:16:58 - The Tapestry Profile00:18:38 - Points of Interest Search00:21:54 - Let’s Look At The Lower Performing COhatch in Duluth00:23:56 - COhatch Will Not Go Down Town00:26:08 - No Easy Access To An Airport?00:29:52 - Creating A Custom Variable (The Psychographic Cocktail Mixer)00:32:04 - The Hexagon Map (Me Want Honeycomb)00:36:52 - Single Location Vs Multiple In the Same Market?00:39:00 - AD - Site To Do Business (https://STDB.com)00:39:39 - How The Tapestry Chart Is Organized00:41:33 - What Do You See, Bo?00:44:32 - Can It Tell Me What Markets To Look At?00:48:01 - Why This Tool Is A Broker’s Superpower!00:50:50 - CI10200:52:39 - How Will AI Change The Way STDB Is Used?00:58:55 - You Might Be Working Yourself Out Of A Job01:00:58 - Data Discovery Tool01:07:14 - Vancouver!01:08:30 - How To Contact Ben Wilson01:09:03 - Outro
Meet the Woman Behind CRE’s Biggest Brands | MoVo Media Marketing's Mo Regalado and Fly Jamerson
2025/09/02
Everyone knows the names Knakal, Santomassimo, and Azor… but do you know the woman behind their content?
In this episode, we sit down with Mo Regalado, founder of Movo Media, and her content strategist Fly Jamerson, to pull back the curtain on how CRE’s most respected professionals build their online presence — and how you can too.
We talk:
🔹 What brokers are doing wrong on LinkedIn
🔹 Why you are your brand (not your brokerage)
🔹 How Mo became the content voice of CRE royalty
🔹 The Fly test: Would you actually watch this?
🔹 The #1 thing you need to grow on social
Whether you’re a new broker, seasoned investor, or just want to get noticed in CRE — this one’s for you.
🎙 Hosted by Timmy & Bo Barron
📺 Subscribe for more episodes weekly
🔗 Learn more: subscribe.wgbarron.com
Thanks To Our Sponsors
💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl🛠️ **Site to Do Business (STDB) – Powerful CRE analysis and mapping tools: stdb.com🤖 Superpowers HQ – Need a CRE executive assistant? Get one here: superpowershq.com/commerciallyspeaking📊 CRE Marketing Mastermind – wesgay.com/csResources Mentioned In This Episode
🌟Movo Media Marketing: MovoMediaMarketing.com🔗 Follow Fly and Mo: @TheMoRegalado, @hey_itsfly📰 Our Weekly Newsletter: The Inside Scoop On CRE — subscribe.wgbarron.com🏬 Barron Commercial Group: CRE Made Simple — https://barroncommercial.com/🥏 All Disc, No Balls! Tizbee, The Secret Game Of Champions — tizbee.com00:00:00 - Cold Open00:01:16 - Welcome00:05:02 - The Woman Behind Bob Knakal’s, Beth Azor’s and Rod Santomassimo’s Socials00:06:37 - Getting Fired for Calling Somebody a “Douche Canoe”00:09:36 - The Beth Azor Interview00:12:28 - AD - CRE Investor Coach (Link in Shownotes), Site To Do Business https://stdb.com00:13:44 - How Much Level Of Control Do You Have?00:15:31 - Why Bo And Timmy Have A Podcast00:16:56 - When Did Fly Arrive?00:20:27 - Most Common Social Media Mistakes You See Broker’s Make00:20:45 - 1. Posting & Ghosting00:22:06 - Is Youtube Considered Social Media?00:23:54 - 2. Not Being ‘Social” On Social Media00:25:26 - Advertising Vs Content Marketing00:28:11 - The 1st Thing You Should Do To Start00:28:35 - Identify Your Audience00:29:03 - Create 5 Content Pillars (Buckets)00:29:21 - Deal Stories00:30:08 - Personal Interests00:31:45 - Voice Memos00:33:00 - Have Fun! (ie Bob Knakal Hot Tub Video)00:34:42 - Dealing with The Haters00:39:31 - Give it 90 Days00:45:08 - The Conduit btw Interest & Conversion00:46:55 - AD - Site To Do Business (https://STDB.com)00:47:34 - Conversations Your Having With Prospects & Clients Should Be The Content You Create For Social Media00:49:51 - How To End Your Piece Of Content00:53:07 - You Have To Start00:55:22 - Critiquing How Bo Engages With Social Media01:00:40 - Followers Don’t Matter Anymore!01:04:41 - Monroe’s Motivated Sequence01:08:57 - Provide Value and The 3 Es: Education, Entertain, Engage01:11:49 - We Connect With Humans, Dumb Ass01:13:32 - What Is The Point? Why Do Social Media?01:19:36 - Being Well Known Makes Everything Easier!01:21:25 - https://MoVoMediaMarketing.com01:23:59 - Rapid Fire Questions01:27:12 - Final Word01:28:00 - Outro
Podcast reviews
Read Commercially Speaking Podcast- Commercial Real Estate Investing That Entertains podcast reviews
Tarahazel1 2025/08/14
Best in its Class
This show makes commercial real estate actually cool. And by cool I mean informative, interesting, and fun. I love watching Bo and Timmy’s dynamic, an...
Ian Levin, CCIM 2025/06/27
Back to Listening to the Best CRE Podcast
I played the recent podcast on loud and made the whole office listen. Always such great ideas that give new energy to how we do what we do.
Rene' Nelson 2025/06/26
Outwork Your Competition—with Less Work & Learn How to Water Ski
Bo and Michael break down real-world AI tools that every commercial broker should be exploring now—and Timmy’s humor keeps it light, sharp, and engagi...
7448437 2024/11/26
A Podcast About Commercial Real Estate that’s Packed With Knowledge & the Best Humor and Banter
I’ve listened to other podcasts (well…tried to) about commercial real estate because, as a residential real estate agent, I want to know as much as I ...
TonyRishell 2024/10/20
Useful, Funny, & Deep
This isn’t another dry market update or business talk, like some spewing verbal ticker tape on your financial advisor’s hold line.
Instead, your get...
Ehsan Bakhshi CRE 2024/08/22
A phenomenal CRE podcast
As a multi-family broker I truly learn from Bo Barron and his podcast is full of a wealth of knowledge and experience. Highly recommend it!
NickELane 2024/08/08
The best CRE Podcast
Love these guys. Always learning something new and laughing along the way!!
Finnigan MI 2024/07/31
Learning And Laughing
Commercially Speaking with Timmy and Bo Barron is pure gold! 🥇 Our team is absolutely blown away by how much we learn and grow with each episode. The...
Team Ray 2024/07/26
Mark Cypert Music Guesses
I know for a fact that your guest this week Mark Cypert had all of those songs on CDs in his house during the mid 90s.
My dad sent our family group ...
jamesrmilner 2024/07/20
From one CCIM to another; Hey Timmy!!!
This podcast is so good and is a great refresher for all CCIM designees. Talking commercial real estate in a simple way with fun guests. I vote to mak...
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