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. When Should You Hire an Executive Assistant? | Terry Pham of SuperPowersHQ™

    5D AGO

    When Should You Hire an Executive Assistant? | Terry Pham of SuperPowersHQ™

    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/

    1h 21m
  2. Why Smart Entrepreneurs Keep Failing (And Don’t Know Why) | Tebow Group CEO Tommy Martin

    MAR 17

    Why Smart Entrepreneurs Keep Failing (And Don’t Know Why) | Tebow Group CEO Tommy Martin

    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.

    1h 13m
  3. How Top Brokers Actually Think | Gary Martinez, CCIM

    FEB 17

    How Top Brokers Actually Think | Gary Martinez, CCIM

    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

    1h 34m
  4. What Billion-Dollar Investors Actually Look For (It’s Not Your Numbers) | Greg Dugard

    FEB 10

    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
  5. 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
  6. 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
  7. 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
out of 5
48 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!

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