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Commercially Speaking Podcast- Commercial Real Estate Investing That Entertains

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Rating
★★★★★
5
from
51 reviews
This podcast has
149 episodes
Language
English
Date created
2023/04/04
Latest episode
2026/07/21
Average duration
80 min.
Release period
17 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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How to Break Into Commercial Real Estate With No Connections | Daynon Kirby
2026/07/21
Most people never choose a career in commercial real estate because they never realize it is an option. They do not grow up around brokers, developers, investors, or property managers. They do not know the language, the career paths, or the people who can open the first door. Daynon Kirby is working to change that. In this episode of Commercially Speaking, Daynon returns to introduce the Black Foundation, a commercial real estate-focused private foundation built around access, education, investment, and attainable housing. The organization helps minorities, veterans, students, and aspiring professionals discover the many career paths available throughout commercial real estate while creating practical pathways into the industry. Daynon also explains why the foundation is building its own investment arm rather than depending entirely on donations. Its model combines people and profits, using commercial real estate, private equity, and other investments to create a mission that can sustain and expand itself. We also get extremely practical about what someone should do when they want to enter commercial real estate but have no family connections or industry experience. In this conversation: How to break into commercial real estate with no connections • Why CRE offers far more careers than brokerage • How to identify the strongest firms in your local market • What young professionals can offer a brokerage immediately • How AI can help you research firms and create real value • Why joining a collaborative team may be better than starting alone • How to approach experienced professionals without asking to “pick their brain” • The power of CCIM education, scholarships, and relationships • How veterans can transition into commercial real estate • Why attainable housing is a central part of the Black Foundation’s mission • How the foundation combines philanthropy with investments • Why a hand up can create more lasting change than a handout This episode is for students, veterans, career changers, young professionals, and anyone who senses that commercial real estate could change their future but has no idea where to begin. Learn more about Daynon and the Black Foundation: The Black Foundation: theblackfoundationinc.com LinkedIn: Search “The Black Foundation” and Daynon Kirby CCIM resources and education: ccim.com Find a local CCIM professional: findaccim.com Thanks To Our Sponsors 🤖 Superpowers HQ – Need an executive assistant that will anticipate your needs? Get one here: superpowershq.com/commerciallyspeaking💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6VrlSubscribe to Commercially Speaking for more conversations about commercial real estate, investing, brokerage, business, and the people changing the industry. 00:00 – Daynon Kirby Returns With a New Mission 03:20 – What Is the Black Foundation? 08:15 – Building a Nonprofit That Funds Itself 12:50 – Commercial Real Estate Creates Generational Wealth 17:10 – Why Most People Never Consider a Career in CRE 22:30 – Careers in Commercial Real Estate Beyond Brokerage 27:40 – Who Is Actually Suited for Commercial Real Estate? 33:20 – How to Break Into Commercial Real Estate With No Connections 39:30 – Join a Team or Start Alone? 45:10 – What Young Professionals Can Offer Immediately 51:25 – How to Find the Best CRE Firms in Your Market 58:10 – Using AI to Research Commercial Real Estate Companies 01:05:00 – How to Approach a Broker Without Wasting Their Time 01:11:30 – Networking When You Don’t Know Anyone 01:18:20 – The Truth About Affordable and Attainable Housing 01:24:10 – Creating Change Through Mindset and Opportunity 01:31:00 – Paying Opportunity Forward 01:36:40 – How CRE Professionals Can Become Mentors 01:42:30 – Why CCIM Can Transform a Commercial Real Estate Career 01:49:00 – Opportunities for Veterans in Commercial Real Estate 01:54:30 – How to Get Involved With the Black Foundation
Why Hobbycraft Might Be the Most Satisfying Way to Engage Your Creativity Post-50 | Joe Daly
2026/07/07
Most of us never realize how transformative a simple hobby can become—especially when it unlocks a renewed sense of purpose, presence, and creative joy. In this episode, Joe Daly, founder of Daily Goods, reveals how discovering artisan leathercraft at 49 turned into a full-blown business and a new way of living. Joe shares the surprising story of starting with a side passion, the exponential growth fueled by word-of-mouth, and the deliberate decisions to scale while staying true to handmade craftsmanship. You'll discover how a small leather journal transformed Joe’s life—teaching him that creating with his hands isn’t just about products; it’s about connecting to something deeper—faith, purpose, and family. We break down the essential difference between hobby and business, the importance of keep-it-simple product design, and how strategically investing in tools like clicker presses can accelerate growth without sacrificing quality. This is essential listening for skeptics, hobbyists, and entrepreneurs alike—anyone craving more purpose, productivity, and peace in their busy lives. Joe’s story illustrates that it’s never too late to find what makes you come alive and that the pursuit of craftsmanship can be a journey to better mental health, meaningful work, and stronger relationships.Get inspired to pick up your tools, slow down, and rediscover what it means to craft—and why sometimes, the best business move is simply making something with love. Whether you're a seasoned maker or just curious about what it really means to create, this episode will challenge your assumptions and ignite your own creative fire. Thanks To Our Sponsors 🤖 Superpowers HQ – Need an executive assistant that will anticipate your needs? Get one here: superpowershq.com/commerciallyspeaking💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl👍 Like, Subscribe, and share this episode with someone who's deciding what comes after high school. 🎙 Commercially Speaking Smarter Business. Better Conversations. Bigger Laughs. Chapters 00:00 Introduction and Background06:08 The Journey into Leather Crafting13:02 Transitioning from Hobby to Business20:02 The Importance of Craftsmanship and Creativity27:51 Finding Purpose through Creation29:30 The Power of Presence and Creation31:01 From Hobby to Business: The Journey Begins33:38 A Leap of Faith: The Turning Point37:23 Crafting a Unique Niche in Leather Goods45:12 Defining Handmade: The Debate56:17 Building a Meaningful Work Culture01:00:21 Inventory Management and Production Challenges01:08:00 Bulk Orders and Business Growth01:13:47 Transitioning from Hobby to Business01:18:31 Future Projects and Aspirations01:25:28 Content Creation and Marketing Strategies
He Left for Marine Boot Camp a Boy... He Came Back Different | Ben Barron
2026/06/30
What is Marine Corps boot camp really like? In this special episode of Commercially Speaking, Bo Barron sits down with his son, Ben, just nine days after graduating from United States Marine Corps boot camp, to talk about what really happened during those 13 weeks. From arriving at the famous yellow footprints to the mental and physical challenges of training, Ben shares what surprised him most, the moments he wanted to quit, and how boot camp changed him. Bo also reflects on his own Marine Corps experience and what it was like watching his son leave for the same journey decades later. Along the way, they discuss: Why Ben chose the Marines instead of a traditional college pathThe biggest lessons from boot campHow Marine training builds confidence and resilienceWhat parents should know if their child is considering military serviceThe truth about Marine Corps cultureLife after boot camp and what's next in Marine Combat Training (MCT)Whether you're considering military service, raising teenagers, or simply interested in stories of discipline, leadership, and personal growth, this conversation offers an honest look inside one of the toughest training programs in the world. Thanks To Our Sponsors 🤖 Superpowers HQ – Need an executive assistant that will anticipate your needs? Get one here: superpowershq.com/commerciallyspeaking💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl👍 Like, Subscribe, and share this episode with someone who's deciding what comes after high school. 🎙 Commercially Speaking Smarter Business. Better Conversations. Bigger Laughs. ⏱ Chapter List 00:00 Introducing Ben, Fresh Out of Marine Boot Camp 02:25 Why Ben Chose the Marines Instead of College 08:56 Growing Up as Bo Barron's Son 17:52 The Decision That Changed Everything 25:05 Shipping Out Earlier Than Expected 31:45 Arriving at Parris Island 38:52 The Hardest Part of Boot Camp 46:40 Letters From Home 54:30 Passing the Physical Fitness Test 1:02:10 What It Felt Like as a Parent 1:11:12 Marine Combat Training & Becoming Military Police 1:21:05 Could He Be Deployed? 1:30:08 Why College Isn't the Right Path for Everyone 1:39:52 What Boot Camp Teaches Every Young Man 1:48:30 Final Advice for Parents and Future Marines
The Mindset Shifts That Separate the Ultra-Rich from Everyday Investors | Bob Fraser
2026/06/16
Most investors start by asking: "How much money can I make?" Bob Fraser thinks that's the wrong question. In this episode, the co-founder and CFO of Aspen Funds explains why the best investors in the world focus on risk before returns, how billionaire investors build portfolios differently, and why protecting capital matters more than chasing upside. We dive into: ✅ Why good technology doesn't automatically create good investments ✅ The hidden problem with most capital raising strategies ✅ How billionaire investors think about risk ✅ Why Evergreen funds may outperform traditional syndications ✅ The biggest mistakes operators make when raising capital ✅ What Bob looks for before investing in any deal ✅ The future of multifamily, industrial, and retail real estate ✅ Why natural gas may be one of the most important investments of the next decade Plus, Bob shares lessons from being wiped out during both the Dot-Com crash and the Great Financial Crisis and how those experiences shaped the way he invests today. If you're an investor, operator, broker, or entrepreneur trying to build wealth that survives market cycles, this episode is packed with practical insights. Thanks To Our Sponsors 🤖 Superpowers HQ – Need an executive assistant that will anticipate your needs? Get one here: superpowershq.com/commerciallyspeaking💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl
The Human Element in Real Estate Will Outlive AI—Here’s Why | Andie Edmonds, CCIM President-Elect
2026/06/09
Most real estate insiders agree: AI is disrupting brokerage faster than anyone expected. But what if the biggest shifts come from the human side? Andie Edmonds, a trailblazer in commercial real estate and the new president of the CCIM Institute, reveals why trusted relationships—and human intuition—will remain the backbone of the industry, even as artificial intelligence transforms how deals get done.In this eye-opening conversation, Andie shares her journey from Oregon to Arizona, navigating market changes, industry disruptions, and a slower shift towards tech. You’ll discover how AI tools like ChatGPT and Claude are influencing broker decision-making, the undeniable importance of human empathy in client relationships, and the subtle ways ethical dilemmas—like fraud and tenant mix—shape property investments today. Andy also dives into the evolving landscape of healthcare real estate, exploring how demand for behavioral health and senior housing is reshaping asset types, and why landlords need to stay vigilant about new challenges.You'll learn how industry leaders are balancing innovation with trust, and why the future of CRE hinges on mastering both technology and human connection. This episode is perfect for brokers worried about AI replacing their jobs, emerging professionals eager to stay relevant, and anyone interested in how real estate must adapt to survive and thrive in a new era.With decades of experience and a sharp eye on the next generation, Andie Edmonds exemplifies leadership that combines faith, industry insight, and a pioneering spirit. She’s a CEO, a CCIM, and now, the president shaping the future of the largest professional designation in commercial real estate—a must-listen for those who want to understand not just what’s changing, but how to lead through it.Whether you’re a seasoned broker, a future investor, or curious about the ethical dilemmas facing real estate today, this episode offers real talk, actionable insights, and a compelling reminder: Humans are irreplaceable, and trust will always be the most valuable currency in CRE. Thanks To Our Sponsors 🤖 Superpowers HQ – Need an executive assistant that will anticipate your needs? Get one here: superpowershq.com/commerciallyspeaking💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl
Is Multifamily About to Break… or Boom? | Reid Bennett, CCIM
2026/04/08
Everyone is asking the same question right now: Is multifamily still a good investment in 2026? In this episode, we sit down with Reid Bennett, one of the most connected multifamily brokers in the country, to break down what’s actually happening in the market. And the answer might surprise you. We cover: Why multifamily is still outperforming other asset classesThe key difference between today and the Great Financial CrisisWhy tenants aren’t leaving apartments right nowHow overbuilding is impacting Sunbelt marketsWhy Midwest markets are tighteningHow brokers are doing deals in markets they’ve never visitedThe real power of LinkedIn for finding dealsHow AI is about to reshape commercial real estatePlus: A wild story about saving a deal with… a knee injury 🤝 This episode is part market analysis, part strategy, and part glimpse into the future of brokerage. 10x Your Time and Get Paired with an EA Today Superpowers HQ - https://superpowershq.com/commerciallyspeaking 00:00 – Intro 02:00 – Reid Bennett’s Origin Story 10:30 – The Deal That Changed Everything 18:00 – Why CRE Investor Coach Matters 24:00 – How LinkedIn Actually Gets Deals Done 32:00 – How to Create Content That Works 39:00 – Multifamily Market Breakdown (2026) 45:30 – Why Tenants Aren’t Leaving 50:00 – AI Is Changing Everything 57:00 – Collaboration > Competition 01:03:00 – License Portability Explained 01:10:00 – The Future of Brokers 01:16:00 – CCIM + AI Evolution 01:20:00 – Outro
When Should You Hire an Executive Assistant? | Terry Pham of SuperPowersHQ™
2026/03/24
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 backWhy “I don’t have time” is the biggest lieHow founders accidentally become the bottleneckWhat a great executive assistant actually doesThe crawl → walk → run system for delegationWhy control is costing you growthHow to get 10–20 hours of your week backThis episode isn’t about hiring help. It’s about removing yourself as the thing slowing everything down. 00:00 The Value of an Executive Assistant02:29 Terry Pham's Journey and Insights05:08 Common Misconceptions About EAs08:04 Delegation Roadblocks and Overcoming Them10:52 The Role of EAs in Managing Entrepreneurs13:45 Creative Delegation Examples16:20 Identifying Tasks to Delegate19:21 The Importance of Clarity in Delegation21:42 Building a Productive Relationship with EAs24:44 The Emotional Aspect of Delegation27:34 Final Thoughts on Executive Assistants39:36 Evolving the EA Relationship40:23 Understanding Personal Work Styles41:53 Building Effective Partnerships44:43 The 90-Day Integration Process46:47 Anticipating Needs and Responsibilities49:42 Daily Syncs and Accountability52:51 Refining Communication and Expectations55:54 Gatekeeping and Access Management59:02 Balancing Accessibility and Boundaries01:06:30 Transformative Experiences with EAs Resources Superpowers HQ - https://superpowershq.com/commerciallyspeakingEO Dallas - https://www.eonetwork.org/Strategic Coach - https://www.strategiccoach.com/ guest links LinkedIn - https://www.linkedin.com/in/terrypham/
Tebow Group CEO Tommy Martin | Why Smart Entrepreneurs Keep Failing (And Don’t Know Why)
2026/03/17
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-part framework behind every successful business• Why most entrepreneurs only focus on outcomes (and why that’s a mistake)• The hidden reason your business feels “stuck”• How to diagnose what’s missing before you waste another year• The difference between momentum, ministry, and movement• How to build a business that actually makes an impactThis isn’t motivation. This is diagnosis. And if you’ve ever felt like you’re doing everything right—but it’s still not working… this episode will hit. Thanks To Our Sponsors 🤖 Superpowers HQ – Need an executive assistant that will anticipate your needs? Get one here: superpowershq.com/commerciallyspeaking💰🏙️ CRE Investor Coach: No Guess Work, No Wasted Time — https://bit.ly/43t6Vrl00:00 – Cold open 01:30 – 3 failed businesses → what changed 05:00 – The missing pieces framework 12:00 – Why most businesses fail quietly 20:00 – Harvard lesson that changed leadership 30:00 – The “movement vs momentum” model 45:00 – Building a business that actually matters 60:00 – What to do if you’re stuck About The Show: Commercially Speaking is where business, investing, and real life collide—hosted by Bo Barron (CCIM) and Timmy Barron (ADHD). If this episode helped you: Share it with someone building something right now.
The Last Broker Is Alive Right Now | Michael Hironimus, CCIM Is Acting Different
2026/02/24
Artificial intelligence can: Underwrite• Model• Analyze• Draft• Summarize• Prospect• Automate follow-upFaster 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 smaller. Survives. This isn’t hype.It’s trajectory. The last broker is alive right now.
How Top Brokers Actually Think | Gary Martinez, CCIM
2026/02/17
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% brokerWhy specializing changed his income trajectoryThe difference between fighting for business vs fighting for relationshipsThe “Know, Like, Trust” mindset that built his careerHis Santa Fe Springs canvassing strategy (door-knocking an entire city)Why most brokers over-educate and lose trustHow to read your client’s sophistication levelAnd a brand-new Industrial Demand Gap Model that projects supply shortages years in advanceIf you're a broker trying to scale, an investor analyzing markets, or a developer planning your next move, this episode will sharpen your edge. 📊 Want to see the Industrial Gap Model live? Watch the full episode on YouTube. 📬 Subscribe to the newsletter: subscribe.wgbaron.com 🧠 Get an executive assistant: superpowershq.com/commerciallyspeaking And yes, Barbara Corcoran… we’re still waiting. ⏱ CHAPTERS 00:00 – 2,500 Deals and Still Learning 05:12 – From Property Manager to Broker 12:30 – Why Specializing Changed Everything 18:40 – Industrial vs Office vs Retail Personality Types 26:10 – Door Knocking an Entire City 35:20 – Capacity Utilization & Spotting Expansion 44:15 – Stop Chasing Deals 50:10 – The Know, Like, Trust Principle 58:30 – Over-Educating Clients (Big Mistake) 01:07:10 – The Industrial Gap Model Explained 01:25:00 – Forecasting Demand & Vacancy 01:35:20 – Negotiation Strategy in Tight Markets 01:43:00 – The Humility of Mastery
What Billion-Dollar Investors Actually Look For (It’s Not Your Numbers) | Greg Dugard
2026/02/10
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)
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 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
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.

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5 out of 5
51 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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