Midwest Mogul’s Show

About Midwest Mogul’s Show

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.

Publisher

Carter Crowley

Category

business

Language

en

Explicit

No

First episode

29 Dec 2020

Latest episode

10 Oct 2026

Latest episodes

103 episodes in the feed.

1. 

   10 Oct 2026

   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. 

   6 Oct 2026

   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. 

   2 Oct 2026

   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

Who has been a guest on Midwest Mogul’s Show

Names identified in recent episode analyses. Showing up to five guests.

• Carter Crowley
• Zach Morgan
• Mark Pomerenke
• Derek Loda
• Josh Jensema

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

4 ratings

Spotify

5.0 / 5

1 ratings

Podcast Authority Score: 30 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

47

Social presence

0

YouTube

0

Engagement

32

Contact Midwest Mogul’s Show

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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