The Strategic Success Podcast

In this first episode of the Messy Money Podcast, Courtney Fricke sits down with Ellis San Jose, a 30+ year Real Estate investor who specializes in curative title work, the side of Real Estate most people avoid. ATTENTION: The information shared in this episode is for educational and informational purposes only and reflects personal experiences and opinions. It is not intended as legal, tax, finan...

In this episode, Courtney sits down with returning guest Joey Long, an active investor in the Tampa Bay market (primarily St. Petersburg and Pinellas County), for an honest review of what 2025 exposed for Real Estate operators and what Joey is doubling down on in 2026. The Tampa Bay market surged post-COVID, then flatlined heading into 2025. Between shifting buyer demand, rising property taxes, an...

Most Real Estate investors try ChatGPT once, get vague or generic answers, and walk away thinking it’s overrated. In this episode of AI for REI, Courtney Fricke and Maria Giordano break down why that happens and what investors are actually doing wrong when they first start using ChatGPT.This conversation is not about tools, upgrades, or technical jargon. It’s about mindset and usage. The biggest m...

Most couples do not intentionally design their life together. They drift, repeat the same year, and mistake effort for alignment. Every year, my wife and I sit down for one conversation that prevents that drift. This episode walks through the exact annual framework we use to review the past year, get aligned in the present, and intentionally plan the next season of life. This is not about resoluti...

Most Real Estate operators are still marketing like it’s 2012. Cast a wide net, say “we buy houses,” and hope the right deal shows up. In 2025, that approach quietly failed a lot of otherwise hardworking investors. In this episode, Courtney sits down with title attorney and business owner Jared Miguez to break down what last year exposed behind the scenes and why 2026 will reward operators who get...

Courtney Fricke sits down with Adam Johnson, a long-time Real Estate investor with over two decades of experience, to reflect on the lessons 2025 forced him to confront and how those lessons are reshaping his focus for 2026.What began as a normal year quickly turned into a life-altering wake-up call when Adam faced a serious health crisis that removed his ability to work for months. That interrupt...

Most Real Estate investors are hearing about AI everywhere but still feel unsure how it actually fits into their business. In this episode of AI for REI, Courtney Fricke and Maria Giordano break down AI basics in plain English for investors who already know how to do deals but feel lost when people start talking about prompts, automations, and AI tools. This is not a technical conversation and it...

Most investors assume Seller Financing fails because of bad terms or weak negotiation. In reality, it fails because it’s offered to the wrong sellers. In this episode, Courtney reframes Seller Financing as a seller-specific solution, not a universal strategy. She explains why most sellers will never need Seller Financing and why that’s not a rejection, but a filter. The investors who succeed with...

In this episode, Courtney sits down with her student Colleen Gallagher for an honest, behind-the-scenes look at what 2025 actually looked like as a wholesaler experimenting with multiple Real Estate strategies. From wholesaling and creative finance to managing a highly intensive shared-housing property, Colleen breaks down where she made money, where she lost time, and which decisions she would ab...

Many buyers and investors across Louisiana are sitting on the sidelines right now. They’re waiting for interest rates to drop, headlines to improve, or for someone online to say it finally feels “safe” to buy again. In this episode of Louisiana Real Estate Talks, Courtney Fricke is joined by longtime business partner and investor Stephen Keighery (aka Aussie Steve) to make a clear, grounded case f...

Real Estate meetups and REIAs are struggling and it’s not because people stopped wanting community. In this episode, Courtney breaks down the uncomfortable truth many meetup leaders don’t want to admit: attention has moved. Investors are discovering education, credibility, and leadership online long before they ever walk into a room. And if your meetup doesn’t have a strong online video presence,...

Land investing gets written off as boring until you see what’s actually possible when it’s done intentionally. In this episode, I’m joined by Chris Johnsen, a full-time land investor who generated roughly $750,000 in gross profit in 2025 despite a more competitive and demanding market. We break down what really worked, what stopped working, and why his strategy in 2026 looks very different than it...

2025 forced a lot of Real Estate operators to pause and reassess what they were actually building. In this episode, Courtney sits down with returning guest Shaun Stephens, a full-time landlord and buy-and-hold investor in Ohio, to unpack what 2025 revealed about portfolio growth, management overhead, and lifestyle tradeoffs. What starts as a conversation about buying rentals turns into a deeper di...

Many Real Estate investors feel hesitant about AI. It sounds complicated, risky, or like just another thing to add to an already full plate. In this episode, Courtney Fricke and Maria Giordano cut through the noise and explain why AI is not a trend, a gimmick, or a replacement for experience. Instead, they make a clear case for why AI is quickly becoming essential infrastructure for modern Real Es...

If you are facing foreclosure, the most dangerous thing you can do is wait for permission to act. In this episode, Courtney walks through what she calls the “come to Jesus” conversation she has with homeowners and property owners facing foreclosure. This is the conversation that happens before any offer is ever discussed. The goal is clarity, not pressure. Courtney breaks down how foreclosure actu...

If you’ve ever lost a deal to someone with less experience than you, this episode isn’t about ego. It’s about adaptation. The Real Estate investors getting picked today aren’t always the most skilled operators. They’re the ones people recognize, remember, and trust because they show up consistently. Skill still matters. But visibility is how credibility is built now. In this episode, I break down...

Every investor lived through 2025 differently. For Rich Rice, 2025 marked a major shift. A new season of fatherhood, multiple moves, joint ventures that tested relationships, deals that went sideways, and a full restructuring of the Fire Center forced him to reassess how he spends his time, energy, and reputation. In this episode, Rich returns to the show for a candid year-in-review conversation....

Most Real Estate deals don’t fall apart because of price. They fall apart because of complexity. In this episode, I break down the 10 real estate problems I solve frequently that most investors, buyers, and even professionals avoid because they’re messy, emotional, or legally complicated. These are the situations where sellers feel stuck, deals stall, and options feel limited. This video walks thr...

In this video, Courtney breaks down exactly what Known Deal Maker Fundamentals is, who it’s for, and why building visibility through content is no longer optional for Real Estate investors and Real Estate-related businesses. This is not about becoming an influencer. This is about becoming known as the person who solves Real Estate problems and closes real deals. What Is Known Deal Maker Fundamenta...

What 2025 Taught Maria Giordano the Hard Way About Running a Real Estate Business2025 exposed a hard truth for a lot of Real Estate investors: deals don’t save you if your operations are broken. In this episode, Maria Giordano joins me for an honest breakdown of what 2025 revealed about running a Real Estate business in a changing market. With over 20 years of experience, Maria isn’t new to cycles...

2025 was the year a lot of Real Estate investors hit pause. Higher friction, tighter spreads, shifting demand, and plenty of people waiting on the sidelines. Stephen “Aussie Steve” Keighery did the opposite. In this episode, Steve breaks down why 2025 became his best year yet, how he expanded while others retreated, and what he believes is required to win in 2026. If you want a grounded look at wh...

2025 forced me to relearn a hard truth: random effort creates random results. It also reminded me that revenue has to stay in first position. This past year was full of distractions. I still did deals, but a lot of my personal life pulled my attention away. In the middle of that, I also made the biggest shift of my career. That combination made one thing very clear as I look toward 2026. If I want...

Last week, legendary investor Peter Fortunato shared a powerful truth: “Your deal is your fault.” That episode sparked a lot of conversation and maybe even a little discomfort because it challenged how we think about responsibility in Real Estate. In today’s follow-up, I’m breaking that idea down even further. This isn’t about blame, it’s about power. When things don’t go according to plan, when t...

If your deal goes wrong, it’s not the market. It’s not the seller. It’s not the lender. It’s you. In this episode, legendary creative investor Peter Fortunato breaks down what it really means to take full ownership of your deals — from how you structure them, to how you treat the people involved, to how you handle things when they go south. For over 60 years, Pete has taught investors across Ameri...

Everyone thinks they have a money problem when it comes to real estate investing. The truth? It’s almost never about money—it’s about having the right skills. In this episode, I break down 5 proven ways to fund your first or next deal with little to no cash of your own. Whether you’re just starting out or you’ve been stuck waiting to “save up,” this will show you how investors actually get deals d...