Midwest Mogul’s Show

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

Alex Hormozi’s $5K Scaling Workshop: The Real Estate Systems That 5X’d Our Conversions Carter Crowley recaps attending Alex Hormozi’s two-day scaling workshop in Las Vegas and explains why the $5,000 ticket paid off after implementing small operational changes that increased deal flow and boosted online-ad conversion rate from 3% to 15%. Key takeaways include auditing your time in 15–30 minute increments to eliminate low-value tasks, using CRM automations to save time per transaction, and focusing on the highest dollar-per-hour activities. He shares advice from the Acquisition.com team that wholesaling and flipping generate cash but aren’t very “exitable,” while rentals, property management, and development are more scalable. The episode emphasizes avoiding shiny object syndrome, choosing a wholesale-first approach, setting strict criteria for flips and rentals, defining “what good looks like” with partners, and making decisions using KPIs while making sales easier through upfront credibility and over-informing sellers. 00:00 Workshop Overview 02:02 Worth the Ticket 02:53 Inside the Workbook 04:20 Time Audit Method 05:28 Automate the CRM 07:42 Stop Doing Too Much 09:58 Wholesale First Strategy 11:25 Flip Criteria Upgrade 13:01 Rental Buy Box Rules 15:35 Founder Roles and Vision 17:57 Define What Good Is 20:06 KPIs and Focus 25:29 Make Sales Easier 28:15 Wrap Up and Next Steps

How We Made $20,116 on a Milwaukee House Flip (With Only 1 Day of On-Site Work) | Friday Deal Breakdown On the Midwest Mogul Show, host Carter Crowley breaks down a Milwaukee, Wisconsin deal at 3930 N 70th St: a 3 bed/1 bath, 1,015 sq ft Cape Cod sold for $165,000 on 6/18/2026 after being sourced via Google PPC. He explains why the property initially seemed ideal as a rental (reported rent of $1,875/month and strong 1%+ rule) but was sold to generate cash for marketing, renovations, and a 12-unit purchase. The rehab was minimal—deep cleaning, junk removal, first-floor paint, yard work, duct cleaning, and plumbing service—totaling $3,127, with holding costs around $2,400 and selling costs about $8,000. Purchased for $124,287, total costs were $144,883, producing $20,116 net profit. He also discusses 100% purchase financing through Kiavi and emphasizes rapport-building to win competitive pre-foreclosure deals. 00:00 Friday Deal Breakdown Intro 01:04 Property Overview Milwaukee 02:39 Rental Math 1% Rule 03:43 Lead Source Google PPC 04:23 Walkthrough Before Photos 05:45 Light Rehab Scope 07:20 After Photos Results 08:14 QuickBooks Numbers Profit 10:08 Flip vs Rental Decision 12:10 Financing With Keyavi 12:47 Winning Deals With Rapport 13:40 Wrap Up And Contact

In this episode, we sit down with Zach Morgan—a real estate investor who’s built a 60+ unit rental portfolio and flips 24 houses a year, all while leveraging one of the most overlooked tools in the game: cold calling. Zach breaks down his step-by-step approach to sourcing off-market deals, building rapport over the phone, and turning distressed properties into long-term cash flow.

Whether you're just getting started or looking to scale your rental business, Zach shares the exact strategies, scripts, and systems he uses to stay consistent and competitive in a crowded market. From lead generation to long-term wealth-building, this is a masterclass in buy & hold investing with a cold-call twist.

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In this episode, we sit down with Mark Pomerenke — a hotel developer, operations specialist, and serial entrepreneur — to unpack his journey from humble beginnings to building business empires across multiple industries. Mark shares how he broke into the hotel business, the power of vertical integration, and how he’s now using his expertise to help others scale their operations and step into real estate lending.

What sets Mark apart isn't just his track record — it's his foundation. A faith-based entrepreneur and committed Christian, Mark talks about how his relationship with God has shaped his values, decisions, and leadership style throughout his career.

Whether you're in real estate, hospitality, or simply trying to build something meaningful, this episode is packed with practical wisdom, spiritual perspective, and entrepreneurial insight from someone who’s done it all — brick by brick.

In this powerful episode, Carter and Joe sit down with real estate investors Derek Loda and Josh Jensema for a deep dive into what it really means to build a business that supports your ideal lifestyle — not just your income goals.

Together, they unpack the importance of clarity of vision, and how defining your personal and professional "end goal" can drastically reshape the way you approach your daily actions, deal flow, and long-term strategy.

We also get into the often overlooked conversation around owning properties free and clear vs. being 100% leveraged. While leverage can be a powerful tool for growth, the guys explore how debt-free ownership can create true peace, freedom, and flexibility, especially as your priorities evolve over time.

What You’ll Hear in This Episode:

• Why not every real estate investor needs to build a 1,000-door portfolio

• The mental shift from “hustle mode” to “lifestyle design”

• The pros and cons of owning real estate free & clear

• How to reverse engineer your life goals into your business plan

• Why slowing down and getting intentional might be your best move yet

Whether you're just starting out or you’ve been grinding for years, this conversation will challenge you to rethink your “why,” and help you take action that aligns with the life you're actually trying to live.

After 20 years of active duty in the U.S. Air Force and multiple overseas deployments, Mike Taddy came home with a mission of a different kind—building a life rooted in family, freedom, and financial independence. In this episode, Mike shares how he transitioned from military life to real estate entrepreneur, starting a property management company, acquiring dozens of rentals, and even owning an assisted living facility. But that’s not all—Mike also runs a full-blown farm in Northeast Wisconsin with his wife and four kids, raising cows, chickens, pigs, and more. From fighter jets to farm chores, this episode is packed with wisdom on discipline, legacy building, and the power of betting on yourself after service. Whether you’re a veteran, an aspiring investor, or someone dreaming of a more intentional lifestyle, Mike’s story will fire you up. __________________________________________________________________________ Carter Crowley runs a house flipping/wholesaling business based out of Oshkosh WI. Since going full-time in 2018, Carter & Bryan have completed over 100+ flips/wholesales and have acquired a portfolio of 40+ rental units & 100+ self-storage units. In addition to the investment business, Carter holds a real estate license in the state of Wisconsin & has helped clients buy/sell over $25,000,000+ of property. Follow along as we grow our real estate investing business from multiple six-figures to a seven-figure operation. Free Course on Wholesaling: https://www.makemoneywithcarter.com/ Free Course on Google Ads: https://www.cartercrowley.com/ Free Course on No Money Down Rentals: https://www.sendcarterrentals.com/ 🚧🚧🚧 DISCLAIMER 🚧🚧🚧 ❎ I am not a CPA, attorney, insurance, contractor, lender, or financial advisor. The content in these videos shall not be construed as tax, legal, insurance, construction, engineering, health & safety, electrical, financial advice, or other and may be outdated or inaccurate; it is your responsibility to verify all information yourself. This is a Youtube video for entertainment purposes ONLY ❎

In this episode, we're pulling back the curtain on the darker side of real estate wholesaling. We're breaking down how investors can avoid working with shady wholesalers who take advantage of distressed homeowners—overpromising, underdelivering, and burning bridges in the process.

We also get real about our own marketing struggles—how we spent $13,000 this past month on pay-per-lead campaigns… and only landed one deal. No sugarcoating here—just raw insight into what’s working, what’s not, and how you can avoid some of the costly mistakes we’ve made.

Whether you're an investor trying to build your business the right way, or just tired of the noise in the wholesaling space, this one’s for you.

Are you holding onto a deal too long? Or selling too soon? In today’s episode, we’re diving deep into real estate exit strategies—the different ways to cash out of a deal and maximize your returns. Whether you're flipping, holding, wholesaling, or refinancing, having a solid exit plan is key to long-term success in real estate investing. ✅ In This Episode, We Cover: ✔️ The Top 5 Exit Strategies every investor should know ✔️ How to choose the best exit based on market conditions ✔️ When to sell, refi, or hold for max profits ✔️ Common mistakes investors make when exiting deals ✔️ Real-life examples of good & bad exit decisions 🎯 Who Is This For? This episode is for new & experienced investors looking to strategically plan their real estate exits. Whether you're flipping houses, buying rentals, or wholesaling, knowing when and how to exit can make or break your deals. 📩 Have questions or want personalized advice? Drop a comment below! 🚀 Subscribe for More Real Estate Investing Tips! 🔔 Don’t forget to like, subscribe, and hit the bell so you never miss an episode! __________________________________________________________________________

Carter Crowley runs a house flipping/wholesaling business based out of Oshkosh WI. Since going full-time in 2018, Carter & Bryan have completed over 100+ flips/wholesales and have acquired a portfolio of 40+ rental units & 100+ self-storage units. In addition to the investment business, Carter holds a real estate license in the state of Wisconsin & has helped clients buy/sell over $25,000,000+ of property. Follow along as we grow our real estate investing business from multiple six-figures to a seven-figure operation.

Free Course on Wholesaling: https://www.makemoneywithcarter.com/

Free Course on Google Ads: https://www.cartercrowley.com/

Free Course on No Money Down Rentals: https://www.sendcarterrentals.com/

🚧🚧🚧 DISCLAIMER 🚧🚧🚧 ❎ I am not a CPA, attorney, insurance, contractor, lender, or financial advisor. The content in these videos shall not be construed as tax, legal, insurance, construction, engineering, health & safety, electrical, financial advice, or other and may be outdated or inaccurate; it is your responsibility to verify all information yourself. This is a PODCAST for entertainment purposes ONLY ❎