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Know Before You Owe

Know Before You Owe

By: Jim Black
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Know Before You Owe with Jim Black brings you conversations with top voices in real estate, finance, and entrepreneurship. Each episode explores practical lessons, industry insights, and personal stories from leaders shaping the future of housing and business. Whether you’re an investor, agent, or entrepreneur, this podcast helps you stay informed, inspired, and ready to grow.

Copyright 2025 All rights reserved.
Episodes
  • Real Estate’s “Pizza Tracker”: How Rays Is Exposing What Agents Actually Do

    Real Estate’s “Pizza Tracker”: How Rays Is Exposing What Agents Actually Do
    Oct 20 2025
    You can track your pizza but not your house sale? That’s the problem, and James Dwiggins, CEO and co-founder of NextHome, is here to fix it.

    On this episode of Know Before You Owe, I talk with James about Rays, the platform bringing real transparency to real estate. Think of it as a “pizza tracker” for your transactions, one that shows clients exactly what their agent is doing.

    We cover: • How transparency builds trust (and saves your reputation) • Why most clients think agents don’t do much • How Rays could reshape commissions and consumer expectations • What the future of tech looks like when it’s built for trust, not just transactions If you’re an agent tired of explaining your value, this one’s going to hit home. #realestateagents #realestatetech #realtorlife #raysapp #proptech #realestatenews #realestatecoaching #mls #homebuying #realtorvalue #realestatetrends #housingmarket #realestateinnovation #realestatepodcast #realestatebroker
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    15 mins
  • Massive 705-Home Project Between Chicago & Milwaukee | Jim Black x Sanjay Kuttemperoor

    Massive 705-Home Project Between Chicago & Milwaukee | Jim Black x Sanjay Kuttemperoor
    Oct 13 2025
    What do you get when you mix farmland, a family with 40 years of real estate experience, and a housing shortage the size of Kenosha County? Apparently, 705 new homes. In this episode of Know Before You Owe, Jim Black chats with Sanjay Kuttemperoor, the man helping turn Pleasant Prairie, Wisconsin, into the Midwest’s hottest new zip code. They talk about how his family went from “empty fields” to “fully approved development,” why major players like Microsoft and Haribo have moved in (yes, the gummy bear people), and how this project survived COVID, zoning, financing, and everything else real estate throws your way. Think of it as a masterclass in land development… with a few Packers vs. Bears jokes thrown in.

    🔗 Learn more about Highland Estates: https://highlandestateswi.com/ 🔗 Join the waiting list: https://highlandestateswi.com/reserve #RealEstateDevelopment #MidwestHousing #HighlandEstates #JimBlack #SanjayKuttemperoor #KnowBeforeYouOwe #PleasantPrairie #WisconsinRealEstate #LandDevelopment #HomeBuilding #RealEstatePodcast #HousingShortage #NewConstruction #Chicago #Milwaukee #PropertyDevelopment
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    15 mins
  • How Smart Lenders Are Scaling Without Burning Out

    How Smart Lenders Are Scaling Without Burning Out
    Oct 6 2025

    In this episode of Know Before You Owe, Jim Black sits down with Matt Coles to demystify what it takes to go from mortgage broker to banker, and why warehouse lines and AI-backed decision-making are key to scaling in today’s environment. They also explore how to prepare now for the next market cycle in 2026, how smaller lenders are outpacing big institutions, and how to avoid the burnout of previous booms. A must-listen for mortgage pros building for the long game.

    #mortgagebroker #mortgagelending #broker2banker #warehouselending #mortgagetechnology #realestatefinance #aifinance #loanofficerlife #mortgageindustry #knowbeforeyouowe
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    21 mins
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