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Carson's Corner: Entrepreneurship & Investing

Carson's Corner: Entrepreneurship & Investing

Written by: Carson Jones
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About this listen

Carson's Corner is the podcast for entrepreneurs, investors, and commercial real estate operators who think in decades, not quarters.

Host Carson Jones — investor, author of The Red Flag Playbook, and licensed commercial real estate advisor and business broker — interviews founders, family offices, and industry operators to unpack the deals, strategies, and hard lessons behind real wealth creation.

Carson's Corner is built for investors, entrepreneurs, and operators who are serious about long-term wealth creation — not get-rich-quick schemes.


The world’s wealthiest investors approach investing very differently than most people. Instead of chasing short-term returns, they focus on preserving wealth, reputation, and legacy across generations. Their decisions are often driven as much by relationships and trusted networks as by financial models, and many of their best opportunities come through private deals, family offices, and invitation-only circles, not public markets. Each episode brings a commercial real estate lens to capital deployment, business partnerships, and alternative investments.


Topics covered: commercial real estate investing · industrial real estate · syndications · passive investing · oil & gas · alternative assets · business acquisitions · capital partnerships · entrepreneurship · wealth building · family office strategies · market risk · reshoring trends

For business or property evaluations you can reach Carson Jones at 615-212-5524 - Carson@passive.investments
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© 2026 Carson's Corner: Entrepreneurship & Investing
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Episodes
  • The Future of Live Music Monetization: Band Buddy Founder Gregg Trosper
    May 13 2026

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    A bucket on a fishing pole. That's how Gregg Trosper first watched a Nashville band collect tips, and that's the moment Band Buddy was born.

    In this episode of Carson's Corner, I sit down with Gregg Trosper, founder of Band Buddy, the mobile platform turning live performances into interactive, cashless, revenue-generating experiences for artists and venues. After a five-month beta across 295 live shows, artists using Band Buddy saw an average 42% lift in tips. Now Gregg is scaling the platform to power everything from neighborhood bars to stadium crowds.

    We get into:

    • Why traditional tipping feels like "begging" and how digital changes the artist-fan dynamic
    • The gamification mechanic that lets fans bid up song requests and drives total tips higher
    • Building "stage mode" vs. "crowd mode" — designing one platform for bars, theaters, and festivals
    • Reducing friction with QR-code and text-based access instead of app store downloads
    • Why 60% of venue patrons stay longer and return when interactivity is higher (and what that means for bar owners)
    • The power of surrounding yourself with mentors, advisors with prior exits, and the right development partner
    • Building a startup inside Nashville's music ecosystem

    This conversation is bigger than live music. It's a case study in spotting a real-world problem, validating it with data, and building technology that aligns the incentives of artists, fans, and venues all at once. If you're an entrepreneur, investor, or anyone curious about where fan engagement and creator monetization are headed, this one is for you.

    Learn more or get Band Buddy at your venue: https://bandbuddylive.com


    Support the show

    For business or property evaluations you can reach me at 615-212-5524

    Or Carson@passive.investments

    Connect with me:

    https://www.linkedin.com/in/carsonjones/


    Other Episodes:

    https://carsonscorner.media/

    https://passive.investments/podcast/

    https://rumble.com/c/Carsonscorner

    Disclaimer: This podcast is for informational and educational purposes only and should not be considered professional advice. Always consult your attorney, CPA, or financial advisor before making any financial decisions. All investments and property ownership carry risk, including the potential loss of principal.

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    38 mins
  • Extend & Pretend Is Over: Negotiating Distressed CRE Debt from Strength with Shlomo Chopp
    Apr 28 2026

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    The era of "extend and pretend" is winding down — and for borrowers staring at distressed multifamily and office loans, the next move could define the next decade of their portfolio. In this episode, Carson sits down with Shlomo Chopp, Managing Partner of CASE and one of the most respected voices in distressed commercial real estate, to break down exactly how borrowers can negotiate from a position of strength when the loan starts going sideways.


    With over 20 years in the trenches and nearly $5 billion in CRE deals invested, structured, or advised on, Shlomo has seen every flavor of workout — from CMBS nightmares to family-office repositions. He's also the inventor behind four CRE-related patents and the retailOS™ platform, and has been named a "Top Retail Expert" by RETHINK RETAIL five years running. In other words: when Shlomo talks distressed debt, lenders, borrowers, and operators listen.


    Inside this conversation, you'll learn:

    • Why relationships only carry you so far — and what actually moves a lender to grant relief
    • The single biggest mistake borrowers make with their cash before walking into a workout (and why it kills their leverage)
    • How to "re-underwrite" your own asset like a new acquisition so you can have an honest conversation with the lender
    • What lenders actually want (hint: it's almost never the keys to your building)
    • The negotiation tactics that work in high-stakes restructures — and the ultimatums that blow deals up
    • When to fix it at the property level vs. when it's time to bring the lender to the table
    • The early warning signs that your business plan has shifted from a real plan to "hope"


    Whether you own a single value-add deal or a portfolio of 70+ properties, this episode is a masterclass in protecting your equity, your guarantees, and your reputation when the market turns against you.


    If you're an entrepreneur, investor, or operator in commercial real estate, this is the conversation you need to hear before you make your next call to your lender.


    🎧 Tune in to Carson's Corner: Entrepreneurship & Investing — and don't forget to subscribe, rate, and share with someone navigating a tough deal right now.

    Support the show

    For business or property evaluations you can reach me at 615-212-5524

    Or Carson@passive.investments

    Connect with me:

    https://www.linkedin.com/in/carsonjones/


    Other Episodes:

    https://carsonscorner.media/

    https://passive.investments/podcast/

    https://rumble.com/c/Carsonscorner

    Disclaimer: This podcast is for informational and educational purposes only and should not be considered professional advice. Always consult your attorney, CPA, or financial advisor before making any financial decisions. All investments and property ownership carry risk, including the potential loss of principal.

    Show More Show Less
    34 mins
  • Dave Seymour: From A&E Flipping Boston to Impact Investing
    Apr 6 2026

    Send us Fan Mail

    Impact investing isn’t just about returns—it’s about changing lives while building real cash flow.

    In this episode, Dave Seymour shares how he went from firefighter and paramedic to starring on Flipping Boston—and ultimately into one of the most compelling impact investment models in real estate today: sober living facilities.

    Now 36 years sober, Dave is combining purpose and profit by acquiring multifamily properties and converting them into recovery housing—creating strong returns through a “rent-by-the-bed” model while building environments that genuinely change lives.

    We break down:

    • How impact investing can outperform traditional real estate
    • The sober living model (and why it works financially)
    • The role of the Dover Amendment in scaling
    • How insurance-backed outpatient programs boost revenue
    • Structuring deals targeting ~14% returns over 24 months

    This isn’t theory—this is a model where mission and margins align.

    Support the show

    For business or property evaluations you can reach me at 615-212-5524

    Or Carson@passive.investments

    Connect with me:

    https://www.linkedin.com/in/carsonjones/


    Other Episodes:

    https://carsonscorner.media/

    https://passive.investments/podcast/

    https://rumble.com/c/Carsonscorner

    Disclaimer: This podcast is for informational and educational purposes only and should not be considered professional advice. Always consult your attorney, CPA, or financial advisor before making any financial decisions. All investments and property ownership carry risk, including the potential loss of principal.

    Show More Show Less
    36 mins
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