Commercially Speaking Podcast- Commercial Real Estate Investing That Entertains

Bo Barron, CCIM | Timmy Barron, ADHD

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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Oct 28, 2025 • 1h 39min

How to Use Self-Directed IRAs to Invest in Real Estate (and Alpacas) | with Dana Udumulla

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

Oct 21, 2025 • 1h 34min

How She Built an $800M CRE Portfolio Without Being a Broker | Whitney Elkins-Hutten

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 nextIf 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 #WealthBuildingThanks 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!

Sep 9, 2025 • 1h 11min

The Tool 95% of CRE Pros Don’t Use Right (But Should) | Site To Do Business with Ben Wilson

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 missIf 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.comThanks 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

Sep 2, 2025 • 1h 30min

Meet the Woman Behind CRE’s Biggest Brands | MoVo Media Marketing's Mo Regalado and Fly Jamerson

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 socialWhether 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.comThanks 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

Aug 26, 2025 • 1h 26min

AI Just Leveled Up Again. Here’s What CRE Pros Need to Know. | Michael Hironimus is BACK!

Recorded live, this AI-packed episode breaks down the latest tools actually moving the needle for commercial real estate brokers, investors, and analysts.Michael Hironimus is back to share what’s changed since GPT-4 and where things are heading next. From lead gen to underwriting, pitch decks to property tours — if you’re not using these tools, you’re already behind.We cover:✅ New AI tools CRE pros are adopting fast✅ Real-time data integrations (and why they matter)✅ The gap between automation & analysis — and how to close it✅ Why brokers using AI are eating everyone else's lunch✅ Michael’s go-to stack and live Q&A with the audienceAI isn’t the threat. Other brokers using AI are.🧠 Learn more about Michael: https://superpowershq.com/commerciallyspeaking🔗 Watch past episodes: https://www.youtube.com/@commerciallyspeaking—🧢 Hosted by Timmy Barron & Bo Barron🎧 New episodes weekly#CRE #AI #MichaelHironimus #CommerciallySpeaking #PropTech #GPT5Thanks 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 Episode7 Day AI For CRE Challenge: https://docs.google.com/document/d/e/2PACX-1vR7Lr9M-0xVZVIhCilK1A1TvxgSUUG_7L9zfdyIxNFXwTHUA0dOjXNTVOLjPIOQAeYNOWddnMrkXdu9/pub🔗 Follow Michael on X: @Mike_Hironimus10% OFF Michael’s Ai Course when you use the code: CSPOD ⁠https://www.implementingaiincre.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 - Cold Open00:00:51 - Intro00:02:31 - Upcoming CCIM Course In Angel’s Envy00:05:40 - ChatGPT-500:15:32 - Claude MCP Servers00:24:30 - Bo Thinks Through CRE Use Cases for MCP Servers00:29:50 - How Timmy Uses AI For Thumbnails and to Animate Photos00:31:15 - Perplexity’s New “Comet” Browser00:38:46 - Automating Entire Workflows with Agentic AI00:47:00 - AD - Site To Do Business (https://STDB.com)00:47:40 - An Avalanche Of Automation00:52:02 - Perplexity’s Bid For Google Chrome00:54:49 - NotebookLM00:55:22 - NotebookLM’s Video Overviews01:01:06 - Study & Learn Feature01:05:56 - GPT - Create a Pop Quiz for the podcast Commercially Speaking01:14:24 - Rapid Fire Questions For Michael01:21:46 - ImplementingAIinCRE.com - Use Code: “CSPOD” for 10% OFF01:21:59 - Outro

Aug 19, 2025 • 1h 21min

He Cold Called His Way to 2,000 Units (Then Gave 20% Away) | with Joe Huber

What happens when a guy with a physics degree, a Vespa scooter, and a philanthropic mission starts cold calling property owners?Joe Huber, founder of Huber Equity Group, joins us to share how he built a 2,000+ unit multifamily portfolio almost entirely off-market — and why he gives away 20% of profits to fight childhood trauma and water insecurity.We talk:How 150,000 cold calls a year fuels his deal flowWhy "digging for basis" is his favorite investing philosophyThe power of walking away from the right dealWhat it's like to raise $5M for a deal — during COVIDWhy his company fights for profits just to give them awayThis one’s about more than real estate. It’s about building wealth on purpose.🔗 Learn more: HuberEquity.com🎧 Subscribe for more episodes like this every week.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📌 Learn more about Joe: https://huberequitygroup.com/My Village Ministries: https://myvillageministries.com/Design Outreach: Elevating Global Poverty https://doutreach.org/📰 Our Weekly Newsletter: The Inside Scoop On CRE — ⁠subscribe.wgbarron.com⁠💰Hearthstone Capital Fund: Investing in CRE With Purpose: https://hearthstonecre.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 Open00:01:03 - Welcome00:02:40 - Welcome Joe Huber00:04:28 - How I Met Joe00:05:25 - Going from 1 to 2,000 Units00:11:36 - AD - CRE Investor Coach, Site To Do Business stdb.com00:12:50 - Digging For Basis00:15:54 - Losses Hurt More Than Gains Help00:18:52 - How did you know about house flipping?00:21:47 - The Off-Market Strategy00:23:11 - I Got Instant Feedback On Pricing00:24:32 - Vespa Scooter Accidents00:27:54 - One of the Best Deal We Didn’t Do00:30:41 - Bo Breaks It Down For Timmy00:32:00 - We’re Making Sausage00:33:06 - Execution With A Scalpel00:34:39 - Joe’s Secret To Cold Calling00:37:37 - Bo’s Best Cold Open Ever00:40:26 - AD - Site To Do Business (https://STDB.com)00:41:05 - S.o H.appy I.t’s T.hursDay00:43:10 - Transparency When Cold Calling00:43:56 - Why Give 20% Of Your Profits?00:46:22 - We Want To Give Even More!00:48:13 - The Causes We Support: 1. My Village00:52:46 - 2. Design Outreach00:59:04 - Fixing The Malfunctions Of The Wells01:00:17 - Huber Equity Has Inspired Hearthstone To Give01:03:11 - We Want To Make More Of An Impact With The Families In Our Units01:05:45 - Future Goals01:09:01 - CRE Is Not All Evil Like In The Movies01:12:27 - Pop Quiz01:17:42 - Outro01:18:40 - Shoutouts

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