Midwest Mogul’s Show

Carter Crowley
  • 5.0 (4)
  • INVESTING

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. 05/02/2025

    Cold Calling for Cash Flow: Zach Morgan’s Buy & Hold Playbook

    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. Want to Join Caffeine & Cashflow on a Monthly Basis?  https://www.facebook.com/share/g/1EmkisAhEg/ Follow Zach:  https://www.facebook.com/zack.morgan.1441

    1h 1m

  2. 04/23/2025

    Brick by Brick: Building Empires in Hospitality and Beyond with Mark Pomerenke

    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.

    58 min

  3. 04/18/2025

    The Real Estate Life You Actually Want w/ Derek Loda & Josh Jensema

    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.

    54 min

  4. 04/15/2025

    Air Force Discipline Meets Real Estate Hustle with Mike Taddy

    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 ❎

    1h 2m

  5. 04/08/2025

    Working with Slimy Wholesalers & Spending 13k on Leads...

    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.

    35 min

  6. 03/14/2025

    Which Exit Strategy Wins?

    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 ❎

    17 min

  7. 03/11/2025

    Flip or Flop? Running Rehab Numbers like a Pro...

    In this episode, we break down the key factors you must consider when running renovation numbers for a flip or wholesale deal. Whether you're a seasoned investor or just getting started, knowing how to accurately estimate rehab costs can make or break your deal. We’ll cover: ✅ The key components of a rehab budget (materials, labor, permits, and more) ✅ How to quickly estimate renovation costs without overcomplicating it ✅ The biggest mistakes investors make when budgeting for repairs ✅ Pro tips for getting accurate contractor quotes and negotiating pricing ✅ The difference between light, moderate, and full-gut rehabs ✅ How to factor in holding costs, contingency buffers, and timeline overruns By the end of this episode, you’ll have a clear framework for running renovation numbers like a pro—ensuring you never overpay or underestimate your costs again. 🎧 Tune in now and start making smarter real estate deals!

    20 min

  8. 03/07/2025

    Scaling to 255+ Rental Units in 5 Years with Kevin Gracyalny

    In this episode, we sit down with Kevin Gracyalny, a powerhouse real estate investor who has built a 255-unit rental portfolio in just five years—and he's not slowing down. Kevin shares his journey from his first deal to scaling his investments, discussing the strategies, challenges, and mindset that helped him reach this level of success. But Kevin isn’t just focused on buy-and-hold properties. He’s now expanding into new construction and house flipping, leveraging his experience to diversify and accelerate his growth. We dive into how he’s financing deals, finding opportunities in today’s market, and managing such a large portfolio while still looking for the next big move. If you’re looking for insights on scaling fast, managing growth, and expanding into new areas of real estate investing, this is an episode you won’t want to miss. 📢 Tune in now and learn how Kevin Gracyalyn continues to build his real estate empire!

    1h 2m
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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 - 2025
  • Episodes
    89
  • Rating
    Explicit
  • Copyright
    © Copyright 2020 All rights reserved.
  • Show Website
    Midwest Mogul’s Show