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Host Carter Crowley discusses whether storage units are worth investing in based on his experience owning about 188 units (previously closer to 300 after being bought out of one facility). He explains that larger facilities are easier to run because on-site managers can handle lockouts, collections, auctions, notices, and daily software checks, while small or distant facilities create a heavier owner workload. He notes automation doesn’t always work in rural Northwoods, Wisconsin, where some tenants lack cell phones, email, bank accounts, or discretionary income, making collections difficult. Crowley says storage units are nearly maintenance-free (under $1,000 total across two facilities since 2021/2023) but can be time-consuming due to rent chasing, rating the investment a 6/10. He emphasizes location, SEO, and high visibility, recommends starting with a smaller facility, and suggests hiring local management for 7–10% of gross rents. 00:00 Show Intro 00:17 Are Storage Units Worth It 00:54 Bigger Facilities Win 03:18 Automation Meets Reality 05:12 My Rating and Tradeoffs 05:47 Maintenance vs Collections 07:25 Should You Hire Management 08:56 Location and Marketing 10:13 Start Small to Learn 11:39 Final Takeaways and Q&A

On the Midwest Moguls Show, Carter and Joe discuss how to stay profitable flipping houses, wholesaling, or buying rentals in a declining or seasonal market, especially in Wisconsin winters. They recommend underwriting conservatively by reducing ARV estimates about 5–10% depending on how fast the market is shifting, accounting for longer days on market, smaller buyer pools, and higher holding costs. They note that median-priced, highly desirable homes (like typical 3-bed ranches) tend to sell faster than unique, rural, or higher-priced properties, which are harder to comp and move in winter. They emphasize keeping marketing going but shifting toward wholesaling to reduce risk, targeting sellers who transact year-round (absentee owners, vacant/inherited properties, landlords), and maintaining multiple exit strategies while prioritizing lean operations and strong deal selection. 00:00 Show Intro and Topic 00:55 Conservative ARV Estimates 02:41 Seasonality and Interest Rates 03:52 Longer Days on Market 05:01 Price Points That Still Move 05:58 Sweet Spot Flip Targets 07:40 Switching to Wholesaling 08:39 Safer Exits in Downturns 09:01 Deleveraging Old Flip Inventory 09:33 Wholesaling to Stay Liquid 10:28 Landlords Selling in Shifts 11:02 Winter Seasonality Marketing 12:17 Comp Conservatively Stay Flexible 12:51 Cut Holding Costs Before Year End 14:04 Say No to Mediocre Deals 14:13 Multiple Exit Strategies Math 15:25 Wrap Up and Next Episode

On the Midwest Moguls Show, host Carter Crowley examines whether rental properties make financial sense in 2026, using Wisconsin (including Milwaukee) examples. After deciding to resell a potential BRRRR rental because it wouldn’t work after property management, repairs, vacancy, and maintenance, he breaks down a typical commercial cash-out refinance scenario: a $175,000 single-family home at 7.25% interest on a 20-year amortization with estimated taxes and insurance yields about a $1,808 monthly payment, leaving little to no cash flow even at $2,000 rent. Carter argues investors should more aggressively pursue seller financing—e.g., 5.5% interest over 25 years dropping payments to about $1,520—and negotiate terms like balloons, low down payments, or even principal-only/0% interest structures to improve cash flow, while acknowledging rehab funding challenges and encouraging passing on deals that don’t pencil. 00:00 Show Intro 00:17 Do Rentals Work 2026 01:51 Bank Refi Numbers 03:43 Why Cash Flow Fails 04:57 Seller Financing Pivot 05:35 Seller Finance Example 07:25 Negotiating Terms 09:58 Balloon Refi Strategy 12:24 Funding Rehab Reality 13:53 Zero Interest Power 16:42 When to Walk Away 17:41 Closing Thoughts

Host Carter Crowley reviews an active BRRRR rental remodel in Milwaukee, Wisconsin (2038 W Neil Pl), a 3-bed/1-bath single-family home with a detached garage bought from a wholesaler for $80,000 plus a $10,000 assignment fee. He shows before-and-after conditions and outlines a full rehab (paint, windows, roof, soffit/fascia, flooring, kitchen with quartz and stainless, updated bath, and basement cleanout) targeting $1,650–$1,700/month rent based on local comps and Rentometer. The project stretched to seven months due to contractors disappearing and poor workmanship, forcing his team to finish the job, driving rehab costs from a $40,000 estimate to about $58,560 and likely $60,000+ (around $155,000–$160,000 all-in with holding/closing). Funded by Kiavi at ~10%+ interest with 1 point, he compares renting (refi ~$150,000 at 7.25% on 20-year AM: ~$1,531/mo; modest cash flow) versus flipping for ~$205k–$210k, and stresses contractor due diligence and project management. 00:00 Show Intro 00:17 Deal Overview 00:53 Property Backstory 01:57 Remodel Walkthrough 03:09 Rent Estimate 04:58 Before Photos 07:09 Contractor Problems 08:32 Budget Reality 10:13 Rent Or Flip 11:10 Refi Cash Flow Math 12:41 Long Term Strategy 14:16 Lessons And Wrap Up

On the Midwest Moguls Show, Joseph and Carter explain why homeowners who appear highly motivated—such as those facing probate, inherited properties, foreclosure, or other distress—may still refuse to sign a purchase contract due to overwhelm, lack of information, and “threshold resistance” at the moment of decision. Using an inherited hoarder-house scenario, they describe how sellers often spend weeks to months (or longer) gathering guidance and reassurance, especially during probate. They recommend separating from typical investors by providing value upfront with free, low-barrier resources like guides, packets, newsletters, and vendor recommendations, building trust without being pushy. They emphasize a marketing-first mindset, long-term follow-up through automated email drips and retargeting, and positioning as a local, knowledgeable, authentic resource to improve conversions, protect relationships, and generate referrals. 00:00 Show Welcome 00:19 Why Sellers Stall 01:04 Inherited House Scenario 01:49 Probate Timeline Basics 02:31 Build Trust With Resources 05:26 Be The One Stop Shop 05:50 Threshold Resistance Explained 07:01 Free Guide Lead Magnet 10:26 Answer Their Real Questions 11:42 Stay Top Of Mind 12:16 Ad Spend ROI Thresholds 12:41 Build Helpful Owner Resources 13:22 Lead With Genuine Help 14:50 Avoid High Pressure Closing 16:12 Marketing Makes Sales Easy 17:40 Automated Follow Up Flywheel 18:53 Lower The Ask With Value 20:00 Create Guides With AI 20:53 Repurpose Guides For Referrals 21:40 Wrap Up And Call To Action

On the Midwest Mogul Show, Joseph and Carter discuss their Friday Deal Breakdown on what they’ve found to be the most profitable real estate deals in Wisconsin. They explain why three-bedroom, two-bath ranch-style homes—ideally built from the 1950s onward, and preferably 1980s or newer—tend to be easier, faster, and more predictable flips and rentals than older two-story homes. They describe common hidden issues in early-1900s houses (wiring, plumbing, insulation, code problems, inspector surprises) that can blow up rehab budgets and timelines, shrinking profits through added costs and holding expenses. They recommend larger buffers for major rehabs on older homes (about 15–20%), share costly examples, and note they often wholesale riskier older properties while keeping newer homes when possible. 00:00 Show Intro 00:20 Deal Breakdown Setup 01:28 Best House Type Ranches 02:36 Avoiding Old House Surprises 03:18 Flips vs Wholesales Risk 06:22 Rehab Budget Creep Example 07:18 Why Ranches Make Easy Rentals 08:01 Rental Demand and Rates Shift 08:32 Buying for Growth 08:48 Margin and Exit Plans 09:30 Hidden Costs in Old Homes 10:14 Flip vs Wholesale Strategy 10:52 Timeframes and Real Examples 12:23 Wholesaling Risky Deals 13:32 Budget Buffers and Reputation 15:27 Holding Costs and Deal Flow 16:16 Wrap Up and Next Episode

Why You Keep Losing Real Estate Deals (And How to Win More Offers vs Other Investors) Host Carter Crowley explains why real estate investors lose deals in competitive situations and how to secure more opportunities when flipping, wholesaling, or buying rentals by improving pre-appointment, appointment, and post-appointment actions. He emphasizes being personable rather than scripted, responding quickly, doing what you say you’ll do, and sharing credibility materials like testimonials, examples, or videos before meeting. He recommends sending a personal selfie video text to confirm appointments and consistently following up. During walkthroughs, he advises against belittling homeowners or the property, focusing instead on solving the seller’s problem, building rapport, and communicating clearly about when you’ll deliver an offer. He also suggests politely asking sellers to share what price is needed if you’re close, and following up creatively with value rather than generic “just checking in” messages. 00:00 Show Welcome 00:17 Why Deals Get Lost 01:34 Pre Appointment Edge 02:42 Credibility And Video Texts 05:32 Win The Appointment 07:59 Follow Through And Reminders 09:31 Ask For Best Price 10:45 Post Appointment Value 11:54 Wrap Up And Next Steps

Our Worst Door County Flip: 9-Month Nightmare, $28K Holding Costs, and a -$1,213 Loss (Lessons Learned) Carter Crowley reviews a Forestville (Door County, Wisconsin) A-frame flip that went wrong at nearly every step, ultimately losing $1,213 despite selling for $255,000 and receiving multiple offers over list. The inherited property was severely neglected, filled with thousands of beer cans, smoke-stained throughout, and had major structural issues including rotted crawlspace floor joists and floors sagging 7–8 inches, requiring a full gut, new footings, and a reframed floor system. The project ran March to November, went well beyond a 6-month hard money note, and racked up about $28,000 in holding costs plus $91,000 in rehab on a ~750 sq ft, one-bedroom loft home with no garage. He shares key lessons on handling seller objections, avoiding emotion-driven buys, underwriting conservatively, and being cautious with small, crawlspace, highly distressed, remote rehabs. 00:00 Deal Gone Wrong 01:08 Where It Happened 02:25 Seller Objections 04:33 Why We Bought It 07:25 The Real Damage 07:56 Gut Rehab Nightmare 10:12 Loan and Holding Costs 12:22 Finished Before and After 15:41 Lessons Learned 16:37 Final Numbers Breakdown 19:53 Underwrite Conservatively 21:31 Wrap Up and Next Steps

Why Most Real Estate Investors Never Get Past 10 Deals (And How to Scale) On the Midwest Mogul Show, host Carter Crowley explains why many real estate investors stall before 10 deals and outlines the core systems needed to scale flips or rentals without burning out. He highlights common constraints like limited capital and financing, recommending networking with local hard money and commercial lenders and leveraging home equity when possible. Carter emphasizes moving off the job site by building a reliable contractor base through consistent “contractor lead generation,” sharing tactics like connecting at big-box store pro desks and early-morning parking lot outreach, and warns how a bad contractor can stall projects. He encourages hiring sooner (bookkeeping, accounting, assistants) to buy back time, compares buying from wholesalers versus running your own marketing, stresses predictable lead flow, and closes with the importance of thinking like an investor, improving systems, and upgrading mindset to grow consistently. 00:00 Why Most Quit Early 01:15 Funding and Capital Options 05:10 Stop Doing It All 06:07 Contractor Lead Generation 10:44 Hire and Delegate Sooner 15:08 Build Predictable Deal Flow 19:20 Think Like an Investor 22:51 Mindset and Next Steps 24:21 Wrap Up and Contact

Friday Deal Breakdown: How We Made $12,750 Wholesaling a Milwaukee House Sight Unseen On the Midwest Mogul Show, host Carter Crowley breaks down a Friday wholesale deal in Milwaukee, Wisconsin where his team made $12,750 profit on a sight-unseen offer in a high-crime area they chose not to visit in person. The lead came from SEO when Freeman submitted an inquiry about his late mother’s vacant, borderline-hoarder home, where utilities were off and later pipes froze, causing basement water; they disclosed the issue and credited for the inconvenience. Carter partnered with an experienced local wholesaler via a joint venture to price and disposition the deal, recommending a double close to protect a fee over $10,000. They contracted the property for $10,000, had about 30 days to close, resold for $37,500, and used SpotCrime to assess neighborhood risk and explain why the exit strategy was rental-only. 00:00 Deal Breakdown Intro 01:32 Lead Story and Property Issues 03:18 JV Partner and Exit Strategy 04:30 Photos and Rehab Scope 07:21 Contract Price and Closing Numbers 09:06 Wholesaling Pitch and Ethics 10:53 Crime Map Due Diligence 12:35 Marketing and Final Takeaways

How We Bought $10M+ in Real Estate From ONE Lead Gen Method (Google PPC, SEO & Scaling by Expanding Markets) On the Midwest Mogul Show, host Carter Crowley explains how his business has bought over $10 million (likely closer to $15 million) in real estate primarily through online advertising—Google PPC, Facebook leads, and SEO—and why focus and consistency matter more than constantly switching strategies. He shares acquisition totals by channel (including 53 from Google Ads and 46 from SEO since late 2024), discusses fast “speed to lead” response expectations with paid leads costing about $500 each, and outlines budgeting and performance targets, including spending over $20,000/month and aiming for a 4X return with roughly $4,000–$4,500 cost per deal. Crowley contrasts paid marketing with manual methods, recommends evaluating ROI over 6–12 months, and details how expanding from the Fox Valley into larger Wisconsin metros like Milwaukee improved scalability, lead costs, and deal margins. 00:00 Online Ads Overview 01:41 Marketing Basics 03:13 Proof and Deal Counts 04:42 Why Google Ads 07:51 Consistency and Focus 10:15 Budget and Deal Costs 14:28 ROI and Doubling Down 15:45 Expand Your Market 21:53 Neighborhood Risk Example 22:32 Final Scaling Advice

Friday Deal Breakdown: $70K+ Profit in 2 Months Flipping Two Duplexes in Middleton, WI Host Carter Crowley breaks down a buy-and-resale deal involving two side-by-side duplexes (four units total) at 6715 and 6719 Century Avenue in Middleton, Wisconsin. He explains how the opportunity came from a pay-per-lead list (Speed to Lead), how he built seller confidence with a non-refundable $9,000 earnest money deposit and a non-appraisal-contingent commercial loan plan, and why he chose to resell instead of hold as a rental despite a $1.18M appraisal. After purchasing for $860,000 (April 17) and addressing tenant move-outs via cash-for-keys, cleaning, and listing, he sold one duplex for $500,000 and the other for $510,000 (by June 30), netting roughly $70,000–$80,000 profit after fees and commissions, while emphasizing the value of resourcefulness and relationships. 00:00 Deal Breakdown Intro 01:22 Finding the Lead 03:32 Seller Trust and Terms 05:48 Purchase Price and Financing 08:31 Rehab Numbers and Appraisal 11:10 Sell vs Hold Decision 12:42 Tenant Strategy Cash for Keys 15:10 First Duplex Sale Breakdown 16:42 Second Duplex Sale and Profit 19:31 Lessons and Wrap Up

How to Run Numbers on Rural House Flips (20 Acres Tri-Level Deal Breakdown in Wisconsin) Host Carter Crowley explains how he evaluates and comps rural house flips using a real example: a tri-level at N11822 County Road P in Iola, Wisconsin on 20 acres. He breaks down the property details (3 bed/3 bath, ~1,762 sq ft above grade plus 986 below grade, built 1959, 1-car garage) and shows why rural, multi-level homes are hard to comp, requiring larger radius searches and older sale dates. He compares a few multi-level sales (including $500k, $445k, and $336k) and discusses adjusting for acreage using vacant-land value (e.g., $10k/acre) and price-per-square-foot logic, then recommends staying conservative on ARV (often subtracting ~10%) due to appraisal and buyer-pool risk. He shares their appraisal ($481k), their purchase price ($347k; prior 2017 sale $332k), estimated $11–12k light rehab, and a conservative resale target around $450k to preserve roughly a $50k margin, plus lessons on following up on offers and key remodel updates (paint, floors, carpet, closets, possible central air). 00:00 Rural Flip Overview 01:23 Subject Property Details 03:28 MLS Radius Search Basics 05:45 Finding First Key Comp 07:27 Expanding Radius and Land Value 09:54 Conservative ARV Strategy 12:07 Three Multi Level Comps 14:14 Adjustments and ARV Estimate 16:42 Appraisal vs List Price 18:08 Deal Math and Profit Buffer 20:09 Offer Follow Up Lesson 21:26 Remodel Photos and Scope 23:52 Final Comping Checklist 24:47 Wrap Up and Subscribe

Midwest Mogul Show Host Carter Crowley explains how to question motivated sellers to get better results, emphasizing a conversational, open-ended approach tailored to lead source (cold outreach vs warm inbound). He recommends starting with “Fill me in on what’s going on” and then asking why the seller contacted a direct buyer instead of listing with an agent, using pauses and “tell me more” to uncover the emotional reasons behind selling rather than peppering condition questions or pushing price early. Carter suggests confirming mortgage, liens, taxes, or other encumbrances to gauge equity, shares an example where solving probate-related issues led to a much lower purchase price than the seller’s initial ask, and offers a key prompt for larger property owners: asking what information they need to feel comfortable sharing details. 00:00 Show Intro 00:41 Cold vs Warm Leads 02:33 First Open Question 04:08 Dig Deeper Without Talking 06:06 Emotion Beats Logic 10:30 Avoid Price Talk Early 12:49 Probate Deal Example 14:48 Questions for Big Owners 17:12 Wrap Up and Next Steps

Seller Financing Explained: How to Structure Offers + 10-Property Milwaukee Deal Breakdown Host Carter Crowley breaks down seller financing—when an owner acts as the bank—and explains why it can beat traditional lending, especially for free-and-clear properties and rental acquisitions. He shares how to pitch terms, stress relationship and trust, and present 4–5 offer options (including low down payments and even 0% interest) while pushing back on 20% down requests. Using a 10-property Milwaukee package as a case study, he walks through an LOI with a cash offer and multiple seller-finance structures, including the accepted option: $900,000 purchase price, 5% down, 6% interest, 30-year amortization, fixed for 7 years. After a 2025 flood affected 9 of 10 homes, he negotiated about a $46,000 price reduction, details current cash flow, renovation costs, estimated portfolio value, and lessons on property management and delinquency. 00:00 Deal Breakdown Intro 01:08 Seller Financing Basics 02:18 When It Makes Sense 04:11 Pitching The Offer 07:00 Down Payment Pushback 07:58 Trust And Relationships 08:52 LOI Walkthrough Setup 09:39 Cash Offer Option 11:28 Seller Finance Options 16:40 Flood Renegotiation Fallout 19:26 Cash Flow And Returns 21:47 Long Term Portfolio Vision 22:37 Wrap Up And Next Steps