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!

  1. What Billion-Dollar Investors Actually Look For (It’s Not Your Numbers) | Greg Dugard

    2D AGO

    What Billion-Dollar Investors Actually Look For (It’s Not Your Numbers) | Greg Dugard

    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-worth families, and now partnering with founders through permanent capital, a long-term investment approach that rejects forced exits, short-term incentives, and five-year flip cycles. We explore: What investors actually look for before wiring moneyWhy time horizons destroy more value than bad dealsPermanent capital vs private equity and venture capitalHow misaligned incentives quietly ruin partnershipsWhy selling too early kills compoundingThe difference between IRR and long-term wealth creationHow founders should evaluate partners before signingWhy trust beats returns in the long runWhat “life’s work” really means for a founderIf you’re a founder, investor, or operator thinking about taking on capital, this conversation might save you years of regret. 🎧 Learn more about Greg & Seder Grove: https://sedergrove.com 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 📺 Subscribe for more conversations about real estate, investing, leadership, and building things that last. And Barbara Corcoran… permanent capital only. We’re ready. 00:00 – What Billion-Dollar Investors Really Want Why numbers aren’t the point 04:10 – Raising $5B Without a Med School How Notre Dame broke records 09:40 – Why Most Capital Destroys Value The hidden cost of short time horizons 15:30 – What Permanent Capital Actually Means No flips. No forced exits. 22:20 – Why Selling Too Early Is the Real Risk The compounding everyone ignores 30:10 – IRR vs Multiple on Capital (MoIC) Why IRR lies over long periods 38:40 – Incentives: The Invisible Hand The tattoo founders should get 47:30 – Choosing the Right Capital Partner Who you let around the table matters 55:50 – Trust, Talent, and Long-Term Thinking How great companies are really built 01:05:30 – The Taylor Swift Story Yes, this actually happened 01:10:40 – Advice for Founders Before Signing What to know before taking money ⏱️ YouTube Chapters (Keyword-Optimized)

    1h 23m
  2. DST vs 1031: The Tax-Deferred Option No One Explains | With Taylor Ashland

    FEB 3

    DST vs 1031: The Tax-Deferred Option No One Explains | With Taylor Ashland

    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 taxes​Invest passively in institutional-quality real estate​Avoid the 45-day scramble to identify a property​Eliminate active management and tenant headachesWe break down: ​How DSTs actually work inside a 1031 exchange​Why the 45-day window creates bad incentives​When a DST makes sense (and when it doesn’t)​Loss of control, lack of liquidity, and real risks​How 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.com​https://ashpac.com​Instagram: @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

    1h 20m
  3. You Won. Now What? The Money Problems No One Prepares You For | with Garrett Gatton

    JAN 27

    You Won. Now What? The Money Problems No One Prepares You For | with Garrett Gatton

    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

    1h 16m
  4. Modern Neighborhoods Were Designed To Make Us Lonely. The Solution Is Simple.

    JAN 20

    Modern Neighborhoods Were Designed To Make Us Lonely. The Solution Is Simple.

    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

    1h 11m
  5. The Data Center Crisis No One Is Talking About — With Simon Enwia, CCIM

    11/19/2025

    The Data Center Crisis No One Is Talking About — With Simon Enwia, 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% 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: simon@senw.io 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 - Simon@SENW.io, dc.land01:43:09 - Simon Is Hiring01:44:19 - Pop Quiz02:03:25 - forum.senw.io02:04:04 - Outro

    2h 6m
  6. The Executive Coach Your Favorite CEO Is Probably Hiding | with Mary Katherine Wathen

    11/11/2025

    The Executive Coach Your Favorite CEO Is Probably Hiding | with Mary Katherine Wathen

    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

    1h 3m
  7. Transforming Commercial Real Estate with Technology | The Birth of Crexi

    11/04/2025 · BONUS

    Transforming Commercial Real Estate with Technology | The Birth of Crexi

    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

    1h 3m
5
out of 5
47 Ratings

About

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!

You Might Also Like