Collecting Keys - Real Estate Investing Podcast

Mike DeHaan
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In the 'Collecting Keys - Real Estate Investing Podcast,' seasoned Real Estate experts Mike DeHaan and Dan Austin discuss how to use Real Estate to create Massive Income not just Passive Income. Real estate doesn't have to be a get-rich slow game, and by bringing over 500 successful deals worth of experience in three years, their episodes unpack the art of real estate investing, wholesaling, house flipping, and transforming properties into profitable rentals. Listen as they share uncensored insights and strategies, from compelling guest interviews revealing personal journeys and finding off-market deals to in-depth deal analyses and the latest market trends. Whether you're taking your first investment step or scaling up your portfolio, embark on your investment journey with the Collecting Keys podcast - where every episode unlocks a door that brings you one step closer to financial freedom so you can finally live the life of your dreams.

  1. 4D AGO

    EP 481 - Mortgage Rates Fell… So Why Didn’t Investors Win?

    What did you think of todays show?? Lower rates are supposed to unlock the market, so why does it feel harder than ever right now? In this episode, we unpack why things can look better without actually getting cheaper, how pricing is influenced behind the scenes, and the recurring revenue obsession that’s turning everything into a subscription — from weight-loss meds to “free” HVAC inspections. Plus, hear about our real estate bottlenecks, tenant drama, and when paying a property manager actually makes sense. Topics discussed: Introduction (00:00) Rebranding the podcast (01:37) The business of GLP-1s (02:47) Recurring revenue has invaded everything (06:13) The State of the Union Address (09:38) Rates check-in: FHA, DSCR loans, and who's winning (12:34) Insider info and betting: Polymarket, “reverse Jim Cramer,” and real estate (15:42) Media manipulation and real-life Succession (20:55) The hardest part of a flip (23:41) Landlord headaches and tenant grievances (27:12) The truth about the “inventory shortage” (33:14) Sign up to join the FREE Scale Community! https://collectingkeys.com/ Want deeper breakdowns like this every week? Subscribe to the Collecting Keys newsletter! https://collectingkeys.com/newsletter/ Follow us on Instagram! https://www.instagram.com/collectingkeyspodcast/ https://www.instagram.com/mike_invests/ https://www.instagram.com/investormandan/ https://www.instagram.com/dylan_does_deals This episode was produced by Podcast Boutique https://www.podcastboutique.com

    37 min

  2. FEB 24

    EP 480 - The Problem With “No Money Down” Investments

    What did you think of todays show?? Your portfolio might look strong on paper… until you try to use it. This episode focuses on the uncomfortable gap between net worth and liquidity — and how getting that math wrong can quietly kill your options. We break down the cost of selling a rental right now, why desperation in a deal is the fastest way to destroy returns, and where AI realistically fits in real estate (and where it absolutely doesn’t). Topics discussed: New AI agents and the future of the workforce (00:00) How we AI in our real estate business (05:25) What cash-flow calculators get wrong (12:45) Why new investors lose money on "good" deals (17:54) The type of investor you shouldn’t work with (21:40) False net worth and  the refi trap (29:25) Are Airbnbs worth the investment? (33:57) Scaling vs. managing risk (38:43) Sign up to join the FREE Scale Community! https://collectingkeys.com/ Want deeper breakdowns like this every week? Subscribe to the Collecting Keys newsletter! https://collectingkeys.com/newsletter/ Follow us on Instagram! https://www.instagram.com/collectingkeyspodcast/ https://www.instagram.com/mike_invests/ https://www.instagram.com/investormandan/ https://www.instagram.com/dylan_does_deals This episode was produced by Podcast Boutique https://www.podcastboutique.com

    44 min

  3. FEB 17

    EP 479 - How AI Could Change Real Estate Forever

    What did you think of todays show?? AI is moving fast… and the real question is which parts of real estate it will disrupt first. In this episode, we dive into AI hype and why transactions could change sooner than people think. Then, we zoom out to the bottlenecks actually affecting investors right now: from getting rentals leased in this market to why “qualified” borrowers are having liquidity problems. Topics discussed: Rental costs that kill cash flow (00:00) How property management companies cost time and money (03:26) Why new or small investors should self-manage (09:16) Why the “crash” didn’t feel like a crash (14:57) The real lending bottleneck: liquidity and reserves (16:53) The Super Bowl Ring Doorbell controversy (25:22) New AI tech, reliability, and the impact on the economy (28:31) Where AI could change real estate first (41:07) Sign up to join the FREE Scale Community! https://collectingkeys.com/ Want deeper breakdowns like this every week? Subscribe to the Collecting Keys newsletter! https://collectingkeys.com/newsletter/ Follow us on Instagram! https://www.instagram.com/collectingkeyspodcast/ https://www.instagram.com/mike_invests/ https://www.instagram.com/investormandan/ https://www.instagram.com/dylan_does_deals This episode was produced by Podcast Boutique https://www.podcastboutique.com

    46 min

  4. FEB 10

    EP 478 - What Are the Real Reasons Bitcoin Crashed?

    What did you think of todays show?? Bitcoin just crashed below $70K, but why should you care? This event exposed the leverage trap of Bitcoin-backed borrowing and why there were so many forced liquidations. In this episode, we break down what really caused the drop, what's happening as Bitcoin becomes more financialized, and if any of this changes the way long-term investors should think about risk and building a portfolio. Topics discussed: Introduction (00:00) GoBundance event recap (02:30) Market sentiment among high-net-worth entrepreneurs (06:16) How AI will truly impact the real estate market (08:15) Why we’re not ready for an AI buildout (11:58) Why Tesla is building robots (19:39) Solutions to the AI power problem (24:00) Why productivity looks different for the next generation (27:23) The factor privilege plays in who’s successful (31:47) What Brandon Turner’s story says about this market (35:16) Sign up to join the FREE Scale Community! https://collectingkeys.com/ Want deeper breakdowns like this every week? Subscribe to the Collecting Keys newsletter! https://collectingkeys.com/newsletter/ Follow us on Instagram! https://www.instagram.com/collectingkeyspodcast/ https://www.instagram.com/mike_invests/ https://www.instagram.com/investormandan/ https://www.instagram.com/dylan_does_deals This episode was produced by Podcast Boutique https://www.podcastboutique.com

    39 min

  5. FEB 3

    EP 477 - AI Hype vs. Real Estate Reality: Here’s The Catch

    What did you think of todays show?? What are high-net-worth operators actually saying about the market right now? In this episode, we share what we’re hearing from investors — and why AI is showing up in almost every conversation. You'll learn what impact the AI boom could really have on real estate, why some people have become more bearish on the market, and why the country might not be ready for an AI buildout. Topics discussed: Introduction (00:00) GoBundance event recap (02:30) Market sentiment among high-net-worth entrepreneurs (06:16) How AI will truly impact the real estate market (08:15) Why we’re not ready for an AI buildout (11:58) Why Tesla is building robots (19:39) Solutions to the AI power problem (24:00) Why productivity looks different for the next generation (27:23) The factor privilege plays in who’s successful (31:47) What Brandon Turner’s story says about this market (35:16) Sign up to join the FREE Scale Community! https://collectingkeys.com/ Want deeper breakdowns like this every week? Subscribe to the Collecting Keys newsletter! https://collectingkeys.com/newsletter/ Follow us on Instagram! https://www.instagram.com/collectingkeyspodcast/ https://www.instagram.com/mike_invests/ https://www.instagram.com/investormandan/ https://www.instagram.com/dylan_does_deals This episode was produced by Podcast Boutique https://www.podcastboutique.com

    39 min

  6. JAN 27

    EP 476 - The Five-Year Reality Check Every Investor Needs

    What did you think of todays show?? Profitable one year, underwater the next — real estate doesn't always math the way you expect. In this episode, Mike shares why short-term numbers lie and what his once cash-flowing rental portfolio looks like five years in. You'll hear why “looking good on paper” can still turn into a cash problem, what most people misunderstand about tax incentives and lending rules, and how you can avoid surprise tax bills. Topics discussed: Introduction (00:00) Your five-year portfolio reality check (01:13) What people misunderstand about real estate tax incentives (04:00) Why you need to stay on top of professionals you hire (09:53) Why Dylan is replacing his acquisitions manager (13:30) How your problems evolve as you scale (20:28)  Lending rules that catch investors off guard (23:05)  The truth about private mortgage insurance (28:51)  What investors miss about DSCR rates and loan structure (31:02) Early takeaways from 2026 (35:37) Sign up to join the FREE Scale Community! https://collectingkeys.com/ Want deeper breakdowns like this every week? Subscribe to the Collecting Keys newsletter! https://collectingkeys.com/newsletter/ Follow us on Instagram! https://www.instagram.com/collectingkeyspodcast/ https://www.instagram.com/mike_invests/ https://www.instagram.com/investormandan/ https://www.instagram.com/dylan_does_deals This episode was produced by Podcast Boutique https://www.podcastboutique.com

    38 min

  7. JAN 20

    EP 475 - Why Your Real Estate Business is Always Out of Cash w/ Greg Helbeck

    What did you think of todays show?? More doors won’t fix a cash problem. If you’re doing deal after deal but the money never stacks, something in your real estate business isn’t working the way you think it is. In this episode, we unpack what’s keeping investors stuck in that cycle and how to finally get out of survival mode — from the reality of building wealth with rentals to the skill that will keep your business afloat. Topics discussed: Introduction (00:00) Asset protection vs. tax strategy (01:04) Why most investors leave after a few years (03:31) The risk/reward of scaling flips and assignments (06:08) Building wealth with rentals from day one (09:30) Rentals and generational wealth (15:01)  Paper wealth vs. cash reality (16:01) The deal-to-deal trap for flippers (18:59) Why marketing and sales are your most valuable skill (19:52) Market delusion and unreliable comps (21:11)  The difference between systems and operations (27:14) How contractors can make or break a deal (33:39) How to promote your business without it getting awkward (40:37) Connect with Greg Helbeck: https://www.instagram.com/grego_37/ Sign up to join the FREE Scale Community! https://collectingkeys.com/ Want deeper breakdowns like this every week? Subscribe to the Collecting Keys newsletter! https://collectingkeys.com/newsletter/ Follow us on Instagram! https://www.instagram.com/collectingkeyspodcast/ https://www.instagram.com/mike_invests/ https://www.instagram.com/investormandan/ https://www.instagram.com/dylan_does_deals This episode was produced by Podcast Boutique https://www.podcastboutique.com

    45 min

  8. JAN 13

    EP 474 - Why January is Prime Time To Get Deals for FREE

    What did you think of todays show?? Housing affordability; it's everyone's favorite argument. From Trump's ban on institutional buyers    to what's really driving housing prices, this episode breaks down the numbers people ignore and what, if anything, they mean for investors. You'll also hear how to work your CRM with no marketing spend and win deals when taxes and Medicare premiums are a concern for sellers. Topics discussed: Introduction (00:00) Trump’s ban on institution buyers explained (05:46) Why regulations are hard to enforce (09:00) Housing affordability vs. what happens if prices drop (12:25) Who is really driving up housing prices? (16:47) Why housing issues are hard to solve nationally (20:00)  Minneapolis: the nuance most people are missing (19:20) How to get deals with no marketing spend (23:20) Strategies that win deals from people on Medicare  (31:46) Sign up to join the FREE Scale Community! https://collectingkeys.com/ Want deeper breakdowns like this every week? Subscribe to the Collecting Keys newsletter! https://collectingkeys.com/newsletter/ Follow us on Instagram! https://www.instagram.com/collectingkeyspodcast/ https://www.instagram.com/mike_invests/ https://www.instagram.com/investormandan/ https://www.instagram.com/dylan_does_deals This episode was produced by Podcast Boutique https://www.podcastboutique.com

    39 min
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4.9
out of 5
97 Ratings

About

In the 'Collecting Keys - Real Estate Investing Podcast,' seasoned Real Estate experts Mike DeHaan and Dan Austin discuss how to use Real Estate to create Massive Income not just Passive Income. Real estate doesn't have to be a get-rich slow game, and by bringing over 500 successful deals worth of experience in three years, their episodes unpack the art of real estate investing, wholesaling, house flipping, and transforming properties into profitable rentals. Listen as they share uncensored insights and strategies, from compelling guest interviews revealing personal journeys and finding off-market deals to in-depth deal analyses and the latest market trends. Whether you're taking your first investment step or scaling up your portfolio, embark on your investment journey with the Collecting Keys podcast - where every episode unlocks a door that brings you one step closer to financial freedom so you can finally live the life of your dreams.

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