Collecting Keys Podcast

Hosted by Mike DeHaan

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Episodes

515

Latest episode

Oct 2026

Language

EN-US

About the show

Collecting Keys is a weekly real estate investing podcast hosted by Mike DeHaan, Dan Austin and Dylan Koch, three active investors with hundreds of wholesale, flip, rental and creative-finance deals between them. Since 2021 the show has published more than 500 episodes on finding off-market deals, wholesaling, novations and subject-to, flipping, rentals, private lending and scaling a real estate business, plus straight talk on the market and on the gurus selling courses.

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60 recent

October 27, 202643 min

EP 515 - Your AI Is Your Coworker Now. Next It's Your Friend

What did you think of todays show?? If AI can run your back office and keep you company while you drive. In this episode, Dylan shows how his AI bot pulls county data, skip traces leads and loads them into a dialer, and we break down why you need less money than you think, why talking to AI instead of people will leave you empty, and what happens if your AI bill jumps 10x. Plus, Elon's $250K Roadster that still hasn't shown up. Topics discussed: Introduction (00:00) Why it's so hard to care about anything (02:51) Chasing fitness with $5 in your checking account (04:00) Why you need less money than you think (07:27) Mike Tyson and the insanity of being the best (10:18) Are religious people really wealthier? (13:36) Dylan's AI bots that could replace PropStream (15:24) Bots, bot managers and the staff roles going away (21:25) The people talking to AI instead of listening to podcasts (24:29) Why AI friends will leave you empty (25:57) Only 4% use AI beyond search: bubble or barely started? (32:05) What happens when your AI tokens cost 10x (34:48) Elon's timelines, the $250K Roadster and self-driving promises (36:27) 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 (https://podcastboutique.com/) (The corrected text was re-run through `boilerplate_diff.py CKP`: CLEAN, exit 0. 13 topics, every topic 5–10 words, description 81 words.)

October 20, 202651 min

EP 514 - How to run a Real Estate Wholesale company for $100 w/ Greg Helbeck

What did you think of todays show?? Your flip is sitting, your margins are shrinking, and the easy money of 2016 isn't coming back. So who's still winning? In this episode, Greg Helbeck shares the losses he's taking on Seattle-area flips, Dylan explains why Cincinnati is the slowest he's ever seen it, and we break down how AI cut the cost of starting a real estate business to about a hundred bucks. Plus, why most of your competition makes it easy to stand out. Topics discussed: Introduction (00:00) Clickbait thumbnails vs a thousand true fans (00:45) Procrastination by learning and the golden handcuffs (04:15) Greg's $25K Seattle flip loss and why New York sells (10:57) Cincinnati is the slowest Dylan has ever seen it (14:40) Why real estate isn't sexy at an 8% rate (18:53) When toilet paper mailers made deals easy (22:08) How AI cut lead data costs to nothing (24:41) Ego pricing and the guru closing 2 out of 10 (33:34) The New York seller who thought Greg was the wholesaler (37:58) Ask your mentor when they last bought a unit (40:44) Georgia's $25,000 consulting fee workaround (43:24) Revenue down, deals flat: why surviving is thriving (46:23) Connect with Greg Helbeck: https://www.youtube.com/@GregHelbeckREI https://reifasttrack.podbean.com/ https://www.instagram.com/grego_37/ 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 (https://podcastboutique.com/)

October 13, 202642 min

EP 513 - Dylan Replaced His Lead Manager With AI, Should You?

What did you think of todays show?? Who's actually getting paid when you donate, borrow, or hire? In this episode, we break down what nonprofit executives really get paid, how Dylan replaced his lead manager with Claude and cut $1,200 a month in overhead, and why a major mortgage lender just dropped its credit floor. Plus, why investor loans now run cheaper than a regular mortgage. Topics discussed: Introduction (00:00) Why your vote gets ignored after you cast it (02:06) What nonprofit executives really get paid (03:43) Why Mike's fire nonprofit got called a grift (06:23) Mike's $500 challenge: spot the AI episode (10:22) Dylan replaces his lead manager with Claude (11:51) Why AI replaces tasks, not your whole team (16:54) How Grok traced an $80,000 wire in 15 seconds (20:47) Would you get a Neuralink to be 1,000% more efficient? (23:42) Why an insurance company wants to be your lender (27:47) A big lender drops its credit floor (32:38) Why investor loans now beat conventional rates (35:57) Dylan's lease option deal gets hit with two rate hikes (37:31) 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 (https://podcastboutique.com/)

October 6, 202643 min

EP 512 - Regular Rich: Why $2M Liquid Beats $20M in Rentals

What did you think of todays show?? How much money makes you regular rich? Probably less than you think. In this episode, we break down the $2 million liquid number going around Instagram, why Mike says more people are already there than would admit it, and why Dan thinks your rentals don't make you as wealthy as you believe. Mike also explains how he is saving well over $100K a year by building his own software with Claude, and why a former guest's $10 million SEC settlement proves fraud is a choice. Topics discussed: Introduction (00:00) Everyone in America is sick (and third-world bathroom stories) (02:20) Hater for the love of the game: why we call out gurus (06:09) What an SEC settlement should tell investors (07:58) Mike rebuilt the Collecting Keys website with Claude in an evening (10:24) The $3K a month in subscriptions Claude replaced (and what it still can't build) (11:45) The $5K a month pricing tool that sent Mike to collections (14:30) AI is a productivity tool, not Jarvis (and the swear-at-the-robot trick) (20:50) Property taxes, the $28 fire levy, and where the money actually goes (24:26) Why the government, not the bank, owns your house (26:29) What does "regular rich" actually mean? (28:35) Why your rentals don't make you as rich as you think (35:47) Mike's 81-year-old dad stops saving (and $25M vs $250M) (39:02) 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 (https://podcastboutique.com/)

September 29, 202646 min

EP 511 - Self Storage, AI Hate and Extortion w/ AJ Osborne

What did you think of todays show?? Two weeks ago we bashed AJ Osborne on this show. The story was fake, and he came on anyway. In this episode, AJ breaks down why the self-storage numbers you read come from less than 1% of the industry, why no institution is coming to buy your $1M facility, and why he's buying developers' stuck deals at 40% under replacement cost. Plus, the AI phone system that holds his missed calls under 10% while the industry runs 30 to 40%, and why he calls AI hate a psyop. Topics discussed: Introduction (00:00) Setting the record straight on AJ Osborne (00:58) How AJ built a storage business without investors (02:49) Why the REITs can't buy the storage you can (06:26) The 2021 self-storage bubble AJ called (and Goldman shorted) (12:05) Why AJ is buying developers' facilities 40% under replacement cost (16:11) 30-year fixed debt is coming to commercial real estate (18:11) How the REITs crashed storage rents from $200 to $60 (23:41) AI hate is a psyop, millennials are the new boomers (26:57) AJ's AI call center: 300 man hours saved (29:19) AI is the biggest barrier destroyer for small investors (32:14) How to start using Claude in your business (33:31) Survive first: why the pain is the opportunity (38:59) Connect with AJ Osborne: https://www.instagram.com/ajosborne/ https://www.ajosborne.com/ https://www.selfstorageincome.com/ 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 (https://podcastboutique.com/)

September 22, 202637 min

EP 510 - Build Your Own RESimpli, ChatGPT As Your Lawyer, And Home Sales At A 31-Year Low

What did you think of todays show?? Stop paying for software you can build yourself. In this episode, Mike explains how he built his own e-sign tool with Claude in about an hour instead of paying $1,000 a seat, and why the platforms you rent are about to get cooked. Dan shares how ChatGPT wrote the demand letter that killed a $1,000 cancellation fee, we break down why home sales just hit a 31-year low with rates headed for 8%, and Dylan lays out what you should own before the Fed inflates its way out of the debt. Topics discussed: Introduction (00:00) Hyrox, Sydney Sweeney, and women tearing women down (00:01) Fake AI videos and the boomers who fall for them (05:14) RESimpli's 6.0 update broke everything (07:49) Mike built his own loan software with Claude (09:19) Mike's petty lawsuit over a cold text (17:35) Dan's ChatGPT demand letter kills a $1,000 fee (20:01) The $6,000 roof that was a condensation line (21:58) Rates in the high sevens and nobody can qualify (24:49) A 31-year low in sales, no forced sellers (27:14) Shrinkflation: your chicken is now water and salt (28:41) The Fed hikes 25 points, gas at all-time highs (30:22) Dylan's playbook: own assets the government can't print (34:22) 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 (https://podcastboutique.com/)

September 19, 202632 min

EP 509 - Pace Morby's investors are about to lose everything

What did you think of todays show?? The people selling you the deal get paid whether you make money or not. In this episode, we go through the accusations piling up around Pace Morby's sub two fund, the investors who say they can't log in or get their money back, and the payroll theft case that came long before the fund. You'll hear why the gurus are all selling the same dream, plus what Trump's $5,000 check promise would really cost. Topics discussed: Introduction (00:00) The Anthropic quitter and the AI fear grift (00:01) Dylan almost sank the family boat (02:46) Sub two investors locked out of their money (04:12) What the SEC filing on Pace actually shows (07:00) An RV park and a surprise $1.5M note (09:38) Payroll theft long before the fund (13:33) They're all selling the dream (15:46) Trump promises $5,000 checks, the math says $1.3 trillion (17:12) Who actually collects your social security (20:40) F-150s, the Taliban, and government waste (24:55) 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 (https://podcastboutique.com/)

September 8, 202642 min

EP 508 - After Mike's Fire: The Insurance Every Investor Should Check

What did you think of todays show?? The guys who got rich in 2021 will tell you it was skill. It wasn't. In this episode, we break down why almost every big investing win is timing you didn't control, from Northwestern Mutual reps who get paid whether or not you stick around to the real estate gurus who quietly stopped saying go bigger, sooner. Plus what Japan's yen crisis has to do with Bitcoin, and the insurance you should already have before any of it matters. Topics discussed: Introduction (00:00) Why lending companies cannot advertise but pill sellers can (00:01) The insurance every business owner should already have (05:28) What happens when partners skip key man insurance (07:50) Why Northwestern Mutual reps sell you more insurance (10:02) Why nobody actually shows up to industry conferences (14:04) Japan's yen crisis and what it means for Bitcoin (16:30) Trump accounts and whether government money helps you (21:16) Where the money goes when corporate profits rise (25:28) Why no news story matters for more than a week (30:31) Why big investing wins are luck, not skill (34:54) Why the 2021 boom was luck, not skill (38:02) 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 (https://podcastboutique.com/)

September 1, 202645 min

EP 507 - D.R. Horton Neighborhoods are the next Mobile Home Parks

What did you think of todays show?? Nobody tells you the most expensive thing in a deal right now is time. A payoff takes three weeks when a lender can pull one in 15 minutes. A finished flip sits 42 days at a price cut below both comps. In this episode, we break down Dylan's 36 unit seller finance deal and the two year balloon inside it, why note servicers get paid to stall you, and when it makes sense to hire your own property manager. Plus Berkshire Hathaway's bet on home builders. Topics discussed: Introduction (00:00) Why gurus find religion when business dries up (01:39) Soft serve at home and the steroid question (02:17) China, electric cars, and the petrodollar (05:39) Aging politicians and the citizenship test idea (08:47) Dylan's 36 unit deal and the two year balloon (13:42) When it makes sense to hire your own property manager (18:35) Why a payoff takes three weeks (22:47) The payoff that expires before you can close (25:00) The flip that has been sitting 42 days (27:35) Buyers going for blood and offers that never existed (30:37) Berkshire Hathaway's $1.2 billion bet on home builders (37:20) Why D.R. Horton neighborhoods age like mobile home parks (40:41) 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 (https://podcastboutique.com/)

August 25, 202643 min

EP 506 - Do the gurus actually believe in God? Or is it the next grift?

What did you think of todays show?? Every washed up influencer on your feed suddenly found God, and the timing is not an accident. In this episode, we break down faith as a sales pitch, the borrower who filmed himself explaining how to lie for an Airbnb loan, and why real estate advice from 2015 is still ranking on YouTube and still wrong. You'll also hear what a $20 million yacht really costs to keep, and what Mike learned about insurance checks after his house burned down. Topics discussed: Introduction (00:00) Why washed up influencers suddenly found God (01:35) Andy Elliott and the faith sales pitch (03:05) What a $20 million yacht really costs (10:53) The buyer who tried to retrade Dylan (14:55) How a Chinese AI cracked a Bitcoin wallet (17:15) The Airbnb owner who filmed himself telling people to lie (22:35) Why non-recourse debt doesn't exist (24:34) Why 2015 real estate advice still ranks (25:16) Pace Morby and guru advice that was never true (26:09) Mike's burned house and the insurance checks (29:26) The property every landlord wishes would burn (29:42) What servers in Maui and Vail actually make (37:27) Why the 30 year yield hasn't moved DSCR (40:01) 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 (https://podcastboutique.com/)

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