#425: From Accidental Landlord to 7 Rentals - Here’s How

⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm   🎙️ Episode #426 - Not every deal ends in a win—and that’s part of the journey. Coach shares practical advice for handling real estate losses, accepting setbacks, taking action, and learning from mistakes.    ▶️ Next Episode: 22 years of Real Estate Investing Advice in 46 minutes  https://podcasts.apple.com/us/podcast/409-22-years-of-real-estate-investing-advice-in-46-minutes/id1448707654?i=1000708092705   📄 Show Notes: https://www.coachcarson.com/baddealrecovery/   🎬 Timestamps: (0:00) - When deals go bad (1:45) - 3 ideas to handle tough situations (3:38) - The gap between what is & your response to it (5:14) - How to minimize losses (6:55) - Don’t keep funding bad deals (9:00) - Learning from mistakes (10:30) - Playing the cards you’re dealt (12:18) - Share your investing horror stories (12:45) - Sign up for RPM   🔗 Chad's Recommended Links: http://coachcarson.com/rpm  ____________________________________________________________________ ⚒️ Get my FREE Real Estate Investor Toolkit: https://www.coachcarson.com/toolkit-pod 🖥️ Learn with Coach (Courses, Books & more): https://www.CoachCarson.com 👋 Connect with Me: 📸 https://www.instagram.com/coachchadcarson  👍 https://www.facebook.com/coachchadcarson  🐦 https://twitter.com/CoachChadCarson 💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan 💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT

⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm   🎙️ Episode #425 - O’Shea’s first property didn’t go as planned—but it changed everything. Hear how he turned renovation mistakes and budget overruns into a growing rental portfolio and a path toward time freedom.   ▶️ Next Episode: DSCR Loans Explained - How to Qualify Without a W2 or Tax Returns  https://podcasts.apple.com/us/podcast/413-dscr-loans-explained-how-to-qualify-without-a/id1448707654?i=1000709881289   📄 Show Notes:  https://www.coachcarson.com/?p=20803&preview=true   🎬 Timestamps: (0:00) - From accidentally investing to FI (8:38) - O'Shea's daily life & career (11:30) - From Jamaica to NY (12:57) - O'Shea's journey to buy more properties (25:09) - O'Shea's intro to short-term rentals (26:59) - Short-term investing lessons (30:35) - Long-term vs short-term rentals (44:18) - Buying properties w/out enough capital (49:00) - O'Shea's current + future goals (51:19) - Balancing home life & real estate (52:58) - O'Shea's advice for investors (54:16) - DSCR Loans Explained 🔗 Connect with O'Shea:  Instagram: https://www.instagram.com/oshea.gordon/ ____________________________________________________________________ ⚒️ Get my FREE Real Estate Investor Toolkit: https://www.coachcarson.com/toolkit-pod 🖥️ Learn with Coach (Courses, Books & more): https://www.CoachCarson.com 👋 Connect with Me: 📸 https://www.instagram.com/coachchadcarson 👍 https://www.facebook.com/coachchadcarson 🐦 https://twitter.com/CoachChadCarson 💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan 💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT

⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm   🎙️ Episode #424 - What if the path to $1 million wasn't about luck or shortcuts, but about becoming the person who can earn it? I break down why this mindset is more valuable than the $1 million itself.   ▶️ Next Episode: Want Financial Freedom in 2025? Do This. [FULL BLUEPRINT] https://podcasts.apple.com/us/podcast/385-if-i-wanted-financial-freedom-in-2025-this-is-what/id1448707654?i=1000692999289   📄 Show Notes: https://www.coachcarson.com/mindset/ 🎬 Timestamps: (00:00) - Which path would you take to $1 Million? (01:01) - Who these people became (01:57) - The value of becoming (04:01) - The best coach of all time defines success (04:58) - Focusing on controllable details (06:50) - Applying success to real estate (07:46) - Key skills to focus on (08:51) - Mindset: Confidence, patience, persistence (09:56) - Your story and potential (10:52) - You don’t have to do it alone (11:44) - Want Financial Freedom in 2025? Do This. [FULL BLUEPRINT] ____________________________________________________________________ ⚒️ Get my FREE Real Estate Investor Toolkit: https://www.coachcarson.com/toolkit-pod 🖥️ Learn with Coach (Courses, Books & more): https://www.CoachCarson.com 👋 Connect with Me: 📸 https://www.instagram.com/coachchadcarson 👍 https://www.facebook.com/coachchadcarson 🐦 https://twitter.com/CoachChadCarson 💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan 💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT

⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: http://coachcarson.com/rpm    🎙️ Episode #423 – Ashley Hamilton didn’t just build wealth - she changed her family’s future. Ashley shares how she went from hustling to buy her first properties to achieving financial freedom, reversing major health issues, and setting up her kids for success with the 4 powerful financial pillars.   ▶️ Next Episode: Our Rental Investing Journey: 8 Years, 10 Properties, Financial Freedom https://podcasts.apple.com/us/podcast/313-our-rental-investing-journey-8-years-10-properties/id1448707654?i=1000631452829 📄 Show Notes:  https://www.coachcarson.com/4wealthpillars/ 🎬 Timestamps: (00:00) - From waitressing to FI (00:53) - Achieving financial independence (02:03) - Breaking generational curses (03:00) - Setting up children for financial success (06:48) - Investing in children's self-directed IRAs (09:39) - Embracing a health journey (14:49) - Prioritizing self-care and health (17:00) - Qualifying for life insurance (18:29) - Enjoying life and luxury (23:07) - Continuing real estate growth and exploration (25:02) - Maximizing income with fewer properties (26:29) - Section 8 rentals and strategy shifts (30:50) - Short-term rental investments (34:30) - Short-term rental revenue (38:55) - Creative revenue streams (41:10) - Staying connected with Ashley Hamilton (42:43) - Our Rental Investing Journey: 8 Years, 10 Properties, Financial Freedom   🔗 Connect with Ashley:  Instagram: https://www.instagram.com/detroit_investor/ Facebook: https://www.facebook.com/p/detroit_investor-100063539625146/ ____________________________________________________________________ ⚒️ Get my FREE Real Estate Investor Toolkit: https://www.coachcarson.com/toolkit-pod 🖥️ Learn with Coach (Courses, Books & more): https://www.CoachCarson.com 👋 Connect with Me: 📸 https://www.instagram.com/coachchadcarson 👍 https://www.facebook.com/coachchadcarson 🐦 https://twitter.com/CoachChadCarson 💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan 💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT

⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm   🎙️ Episode #422 - What if you could make faster, smarter rental decisions without spending a fortune learning the hard way? I'll show you how ChatGPT is revolutionizing my real estate business, from acquisitions to property management, and even insurance reviews. The ways it’s saving me time and money might surprise you.   ▶️ Next Video: How to Analyze a Duplex Rental Property (Real Life Example) https://www.youtube.com/watch?v=MPbuwBH_ZDo&t=1s   📄 Show Notes: https://www.coachcarson.com/chatgptassistant/ 🎬 Timestamps: (00:00) - Unlock Property Acquisitions with AI (04:54) - Repurpose Content for More Marketing Impact (05:59) - Streamline Property Management with AI (09:33) - Simplify Insurance Policy Reviews with AI (12:32) - Creative Deal Structuring Using AI (14:31) - Build Efficient Systems with AI (15:28) - Update Operating Agreements with AI (17:21) - Automate Checklists and Processes with AI (18:16) - Analyze Your Portfolio with AI Insights (20:09) - Maximize Refinancing, Selling, or Debt Payoff with AI (23:49) - The Role of Community in an AI-Powered World (24:42) - How to Analyze a Real Life Duplex Rental Property ____________________________________________________________________ ⚒️ Get my FREE Real Estate Investor Toolkit: https://www.coachcarson.com/toolkit-pod 🖥️ Learn with Coach (Courses, Books & more): https://www.CoachCarson.com 👋 Connect with Me: 📸 https://www.instagram.com/coachchadcarson 👍 https://www.facebook.com/coachchadcarson 🐦 https://twitter.com/CoachChadCarson 💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan 💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT

📃 Get a Landlord Quote with Steadily: http://www.coachcarson.com/landlordinsurance   ⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm   🎙️ Episode #421 - Think your property is covered? Many landlords discover too late that a standard homeowners policy doesn’t protect rental properties. Coach breaks down the costly gaps in coverage, how landlord insurance works, and the smart add-ons that can save your financial future.   ▶️ Next Episode: 5 Tips to Avoid a Rental Disaster! (Landlord Insurance)  https://podcasts.apple.com/ug/podcast/379-landlord-insurance-5-tips-to-help-you-avoid-disaster/id1448707654?i=1000684689448 📄 Show Notes:  https://www.coachcarson.com/insurancemistakes/ 🎬 Timestamps: (00:00) - The Costly Mistake of Wrong Insurance (00:44) - Understanding Homeowners Insurance (01:18) - What is Landlord Insurance? (02:02) - The Importance of Renter's Insurance (02:24) - Real-Life Insurance Claim Story (04:12) - Key Takeaways on Insurance Types (04:56) - Sponsor Shoutout: Steadily Landlord Insurance (05:28) - Uncovered Gaps in Insurance Policies (11:18) - Special Cases: House Hacking and Family Rentals (13:16) - Ensuring Your Policy Covers Everything (13:59) - 5 Tips to Avoid a Rental Disaster! (Landlord Insurance)   🔗 Chad's FREE ChatGPT Prompts: http://www.coachcarson.com/insurance-prompts   ____________________________________________________________________ ⚒️ Get my FREE Real Estate Investor Toolkit: https://www.coachcarson.com/toolkit-pod 🖥️ Learn with Coach (Courses, Books & more): https://www.CoachCarson.com 👋 Connect with Me: 📸 https://www.instagram.com/coachchadcarson  👍 https://www.facebook.com/coachchadcarson  🐦 https://twitter.com/CoachChadCarson 💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan 💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT

⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm   🎙️ Episode #420 – Most people think real estate investors are all-in on rentals. But the truth is, some of the smartest ones quietly invest in other places that protect their time and freedom when markets shift. I'm sharing the 4 other places I invest. If you’re all-in on rentals, this might change how you think about your strategy. 📄 Show Notes: https://www.coachcarson.com/otherassets/ 🎬 Timestamps: (00:00) - Why diversify beyond real estate (00:55) - My bet inside the stock market (06:11) - Keeping cash for liquidity and security (09:09) - Seller financing and bridge loans  (13:01) - Purely speculative investments (14:55) - Supporting startups that matter to me (17:05) - Real estate as my primary investment focus (18:05) - For real estate investors who want a community ____________________________________________________________________ ⚒️ Get my FREE Real Estate Investor Toolkit: https://www.coachcarson.com/toolkit-pod 🖥️ Learn with Coach (Courses, Books & more): https://www.CoachCarson.com 👋 Connect with Me: 📸 https://www.instagram.com/coachchadcarson 👍 https://www.facebook.com/coachchadcarson 🐦 https://twitter.com/CoachChadCarson 💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan 💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT

⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm   🎙️ Episode #419 - Ryan Phan moved from a small town in Vietnam to the U.S., joined the Navy, and accidentally became a landlord. What started as a forced rental turned into a 12-property portfolio through creativity, grit, and zero excuses.   ▶️ Next Episode:  How to Build your Team — for Long Distance Real Estate Investors https://podcasts.apple.com/us/podcast/337-buying-real-estate-long-distance-how-to-build-your-team/id1448707654?i=1000651050890   📄 Show Notes: https://www.coachcarson.com/navyinvestor/ 🎬 Timestamps: (0:00) - How Ryan got into the navy (2:43) - How Ryan got his first deals (10:50) - When to deploy investing strategies (13:57) - Ryan's homerun flip in SC (16:07) - From the navy to full time real estate (25:07) - Ryan's best deal finding methods (32:36) - Ryan's best financing tool (34:22) - Best advice from Ryan's journey (42:30) - Build your long-distance investing team   🔗 Connect with Ryan:  Ryan's Email: [email protected]   ____________________________________________________________________ ⚒️ Get my FREE Real Estate Investor Toolkit: https://www.coachcarson.com/toolkit-pod 🖥️ Learn with Coach (Courses, Books & more): https://www.CoachCarson.com 👋 Connect with Me: 📸 https://www.instagram.com/coachchadcarson 👍 https://www.facebook.com/coachchadcarson 🐦 https://twitter.com/CoachChadCarson 💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan 💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT

⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm   🎙️ Episode #418 - Everyone talks about scaling fast in real estate, but what if slower, smarter growth is actually the secret? Bigger isn’t always better—especially if you want freedom that lasts.   ▶️ Next Episode: How to Become Financially Free with 5 Small & Simple Rentals https://podcasts.apple.com/us/podcast/357-how-to-become-financially-free-with-5-small-simple/id1448707654?i=1000665864424   📄 Show Notes: https://www.coachcarson.com/skyscraper/ 🎬 Timestamps: (00:00) - Real Estate Growth Myths (00:52) - Rocket vs. Skyscraper (03:07) - Chick-fil-A's Growth and Franchise Model (05:09) - Patagonia's Mission-Driven Skyscraper  (07:24) - The Role of Debt and Organic Growth (09:14) - Focus on Mission-Driven Investing (11:31) - Slow and Steady Wins (14:25) - Debt as a Tool: Use and Risks (15:16) - Redefining Success: Freedom and Time (17:13) - How to Grow Slowly with Others   📕 Chad's Recommended Book:  Small and Mighty Real Estate Investor: https://coachcarson.com/smallandmighty ____________________________________________________________________ ⚒️ Get my FREE Real Estate Investor Toolkit: https://www.coachcarson.com/toolkit-pod 🖥️ Learn with Coach (Courses, Books & more): https://www.CoachCarson.com 👋 Connect with Me: 📸 https://www.instagram.com/coachchadcarson 👍 https://www.facebook.com/coachchadcarson 🐦 https://twitter.com/CoachChadCarson 💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan 💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT

⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm   🏠 Coach Carson’s Capital Expense Cheat Sheet: https://www.coachcarson.com/capex-planning   🎙️ Episode #417 - Want straight talk on seller financing, strong offers, house hacking, and scaling smart? In this no-fluff Q&A, I tackle YOUR real estate questions and break down real strategies that work, especially if you’re just getting started or trying to scale safely.   ▶️ Next Episode: Want Financial Freedom in 2025? Do This. [FULL BLUEPRINT] https://podcasts.apple.com/us/podcast/385-if-i-wanted-financial-freedom-in-2025-this-is-what/id1448707654?i=1000692999289   📄 Show Notes: https://www.coachcarson.com/realestatequestions/   🎬 Timestamps: (0:00) - How to make your offer stand out (4:36) - Would past me be happy with future me? (8:12) - Talking to sellers when buying properties (13:05) - BRRRR Strategy vs flip & sell (16:33) - Starting investing with no money (20:31) - Keeping track of CapEx (26:23) - Handling tenant communications (28:09) - Best bookkeeping software (32:10) - Tips for executing seller-finance deals (38:32) - What is an healthy LTV? (43:20) - Want Financial Freedom in 2025? Do This. ____________________________________________________________________ ⚒️ Get my FREE Real Estate Investor Toolkit: https://www.coachcarson.com/toolkit-pod 🖥️ Learn with Coach (Courses, Books & more): https://www.CoachCarson.com 👋 Connect with Me: 📸 https://www.instagram.com/coachchadcarson 👍 https://www.facebook.com/coachchadcarson 🐦 https://twitter.com/CoachChadCarson 💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan 💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT