Midwest Mogul’s Show

Carter Crowley
  • 5.0 (4)
  • Investing
  • Updated Weekly

Running a business is nothing short of exhilarating. The highs are high & the lows are low. We are all trying to chip away & fulfill a vision to earn incredible amounts of money, have a lasting impact, and make a difference in the local community. But, we can only do that if we stay in this game we call business. The core concept of Midwest Mogul’s Show is to share experiences on how to Make Business Enjoyable Again. We will be interviewing & meeting with other business owners to share their secrets to success. And most importantly, how they consistently stay ”in the game” after dozens of years.

  1. 4h ago

    Is the BRRRR Strategy Still Worth It in 2026? (Real Deal Breakdown)

    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

  2. 4d ago

    Why Motivated Sellers Aren’t Calling You

    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

  3. Oct 2

    The Most Profitable Houses to Flip (And What We Avoid)

    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

  4. Sep 29

    How We Win Deals Even When We’re NOT the Highest Offer

    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

  5. Sep 12

    We LOST Money on This House Flip… Here’s What Went Wrong

    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

  6. Sep 8

    Why Most Real Estate Investors Never Make It Big

    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

  7. Sep 4

    We Bought This Milwaukee House for $10K Sight Unseen

    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

  8. Sep 1

    We Bought $10M+ in Real Estate Using This ONE Strategy

    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

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Ratings & Reviews

5
out of 5
4 Ratings

About

Running a business is nothing short of exhilarating. The highs are high & the lows are low. We are all trying to chip away & fulfill a vision to earn incredible amounts of money, have a lasting impact, and make a difference in the local community. But, we can only do that if we stay in this game we call business. The core concept of Midwest Mogul’s Show is to share experiences on how to Make Business Enjoyable Again. We will be interviewing & meeting with other business owners to share their secrets to success. And most importantly, how they consistently stay ”in the game” after dozens of years.

Information

  • Creator
    Carter Crowley
  • Years Active
    2020 - 2026
  • Episodes
    100
  • Rating
    Explicit
  • Copyright
    © Copyright 2020 All rights reserved.
  • Show Website
    Midwest Mogul’s Show