Episode Overview

In this episode of the Ironclad Underwriting Podcast, host Jason Williams welcomes returning guest Frank Patalano for a deep dive into the current challenges facing commercial real estate investors. From refinancing hurdles and cap rate expansion to rising insurance costs and shifting debt service coverage requirements, Jason and Frank break down how today’s unpredictable market is impacting deals, underwriting strategies, and investor expectations. They share real-world examples, lessons learned, and practical advice on navigating this volatile landscape while keeping long-term goals in sight.

Topics Covered

• Cap rate expansion and its impact on property values
• Refinancing challenges and the rise of cash-in refinances
• Interest rate hikes and their ripple effect on underwriting
• Insurance and tax increases altering projections
• Debt service coverage ratios and lender requirements
• Balancing conservative vs. aggressive underwriting in today’s market

Key Quotes

• "Underwriting is not perfect; you have to go with your best assumptions, but even markets are screwing everybody over."
• "There are many people in much worse shape because they were not figuring in cap rate expansion, and that’s why some are just turning in keys."
• "Real estate is not a short-term game. If you can weather this storm, you will probably find light afterward."

🎧 Connect with Jason:

✅ LinkedIn

✅ https://IroncladUnderwriting.com

✅Linktree

🎧 Connect with Frank:

✅LinkedIn

📌 Episode Overview:

In this episode of The Ironclad Underwriting Podcast, host Jason Williams and recurring guest Frank Patalano take a deep dive into one of the most misunderstood aspects of commercial real estate: the capital stack and waterfall structures. From senior debt to common equity, they unpack how each layer of financing works, who gets paid first, and where the risks and rewards lie. Whether you’re a new investor or a seasoned operator, this episode will give you clarity on structuring deals that stand the test of time.

🗂 Topics Covered:

• The fundamentals of the capital stack: debt, equity, and everything in between
• Why senior debt is the safest investment and how secondary/mezzanine debt works
• Understanding preferred equity vs. common equity and their risk profiles
• The mechanics of waterfall structures: preferred returns, splits, and IRR hurdles
• Why keeping structures simple is often the smartest move for syndicators and GPs

💬 Notable Quotes:

• “Remember, the very first rung gets paid first with the lowest risk, and common equity is last with the highest risk, but also the highest potential reward.”
• “A confused mind says no. If you overcomplicate your waterfall with dozens of hurdles and classes, investors won’t sign up.”
• “Debt is fixed. Equity shares in the upside. That’s the tradeoff: security versus potential.”

🎧 Connect with Jason:

✅ LinkedIn

✅ https://IroncladUnderwriting.com

✅Linktree

🎧 Connect with Frank:

✅LinkedIn

Episode Overview

In this episode of the Ironclad Underwriting Podcast, Jason Williams and Frank Patalano dive into one of the most common struggles new investors face: choosing a market. They share why focusing on a single market early on can help you gain an edge, how to spot pitfalls in neighborhoods, and the importance of truly knowing the area beyond just the numbers. With real-world stories, market analysis tips, and lessons learned from decades of experience, this conversation will help you avoid spreading yourself too thin and build a stronger foundation for long-term success.

📌 Topics Covered

• The importance of starting with one market and mastering it before expanding
• Why boots on the ground and local partnerships are critical for investors
• Market analysis tools, comps, and the role of neighborhood insights
• Risks of over-diversification and benefits of concentrating investments
• Real-world examples of deals that fell through due to local competition
• How neighborhood quality impacts asset class upgrades and rent growth potential

💡Quotes from the Episode

• "You need to know where your tenants are going to go for pizza on a Friday night."
• "I’d rather own the worst house in a nice neighborhood than the nicest house in the worst neighborhood."
• "When you’re starting out, stick with one market—even if it’s not perfect—because you know it best."

🎧 Connect with Jason:

✅ LinkedIn

✅ https://IroncladUnderwriting.com

✅Linktree

🎧 Connect with Frank:

✅LinkedIn

Episode Overview

In this episode of the Ironclad Underwriting Podcast, host Jason Williams is joined by his wife and business partner, Angel Williams, along with fellow partner and former educator, Frank Patalano. Together, they dive into the importance of continuous education, the role of real estate events, and the mindset shifts that separate transactional hustling from transformational growth.

From lessons learned at national conferences to the power of mentorship and mindset, this conversation offers practical takeaways for both new and seasoned investors. Whether you’re looking to expand your knowledge base, connect with like-minded professionals, or learn from others’ mistakes instead of your own, this episode is packed with insights.

🗂 Topics Covered

• The value of education and networking in real estate investing
• Why some investors only learn through their own mistakes
• Transactional vs. transformational approaches in business and life
• How events and summits accelerate growth and shorten the learning curve
• The role of mindset in achieving long-term success

💡 Memorable Quotes

1. “You can’t coach somebody who doesn’t want it. You can talk till you’re blue in the face, and it’s not going to matter.” — Jason Williams
2. “Education and networking are super important aspects of every single part of all my businesses right now.” — Frank Patalano
3. “People aren’t always going to remember what you said or what you did, but they’re always going to remember how you made them feel.” — Maya Angelou

🎧 Connect with Jason:

✅ LinkedIn

✅ https://IroncladUnderwriting.com

✅Linktree

🎧 Connect with Frank:

✅LinkedIn

🎧 Connect with Angel:

✅ LinkedIn

✅TAP Community

✅REI Rocks Podcast

✅ Summit

Overview

In this episode of the Ironclad Underwriting Podcast, Jason Williams and his business partner Frank Patalano tackle one of the biggest red flags in real estate underwriting, blindly plugging numbers into models without understanding what they mean. From overwritten formulas to unrealistic rent projections, Jason and Frank break down common mistakes they see investors and analysts make, and how these errors can cost deals, returns, and credibility. Whether you’re building your first model or reviewing your tenth, this episode will sharpen your eye for detail and help you spot the traps before they derail your underwriting.

Topics Covered

• Why blindly entering numbers into spreadsheets creates hidden risks

• Common pitfalls with rent premiums, occupancy rates, and renovation timelines

• Insurance and tax assumptions that can make or break a deal

• Loan-to-value (LTV) misconceptions in today’s lending environment

• The gap between gross scheduled rent and effective gross income

• How limited partners (LPs) often misinterpret projected returns

Quotes

✅“My red flag is just blindly putting numbers into a model, if you don’t understand how it’s calculated or how it affects your returns, you’re flying blind.”

✅“I’ve seen clients double dip, even triple dip on rent premiums, taking a property from $850 to $1,300 overnight. That’s not just unrealistic, it’s dangerous.”

✅“You can’t be blind on taxes. If you don’t plan for reassessment increases before you close, you’re stuck, and the county will take your property if you can’t pay.”

🎧 Connect with Jason:

✅ LinkedIn

✅ https://IroncladUnderwriting.com

✅Linktree

🎧 Connect with Frank:

✅LinkedIn

🎙️Episode Title

"Mindset Meets Metrics: Underwriting with Certainty, Clarity, and Confidence"

🔍Overview

In this episode of the Ironclad Underwriting Podcast, host Jason Williams sits down with business partner Frank Patalano and master coach Trevor McGregor to explore the deep link between mindset and successful commercial real estate underwriting. They break down why success is 80% psychology and 20% mechanics, how to protect yourself from market swings, and the importance of keeping both your emotions and your deal analysis in check. With real stories, proven frameworks, and practical advice, this episode gives listeners the tools to operate with certainty, clarity, and confidence, especially when handling other people’s money.

📌 Topics Covered

✅Why “white hot desire” drives results in real estate

✅The 80/20 rule of psychology vs. mechanics in success

✅Avoiding analysis paralysis and overconfidence

✅Reading and respecting red flags in deals

✅Surrounding yourself with experienced investors

✅Seeing failures as feedback, not defeat

✅The three C’s of underwriting: Certainty, Clarity, Confidence

✅How mindset impacts investor trust

✅Navigating market cycles with caution and opportunity in mind

✅Lessons from investors who lost everything due to poor risk management

💬3 Key Quotes

✅“Success is 80% psychology and 20% mechanics.” – Trevor McGregor

✅“There is no failure, only feedback.” – Trevor McGregor

✅“When you have certainty, clarity, and confidence in your underwriting, you give that same confidence to your team and your investors.” – Trevor McGregor

🎧 Connect with Jason:

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✅ https://IroncladUnderwriting.com

✅Linktree

🎧 Connect with Frank:

✅LinkedIn

🎧 Connect with Trevor:

✅LinkedIn

🔍 Episode Overview:

In this episode of Ironclad Underwriting, host Jason Williams is joined by business partner Frank Patalano to discuss one of the most common (and costly) red flags in real estate investing: relying on short-term trends for long-term decisions. From unsustainable rent growth projections to unrealistic interest rate assumptions, the duo breaks down the pitfalls of over-aggressive underwriting and emotional investing. This is a must-listen for investors, underwriters, and CRE professionals navigating volatile markets with uncertain futures.

📌 Topics Covered:

✅The trap of using peak rent growth projections (San Antonio & Phoenix case studies)

✅How low interest rates and aggressive refi assumptions led to financial ruin

✅Emotional investing and the illusion of permanent market conditions

✅Airbnb, oil, RV parks: how temporary trends lure in short-term thinkers

✅Why underwriting needs to account for cycles, not spikes

✅Lessons from missed deals, failed forecasts, and post-COVID volatility

✅The fine line between healthy risk and reckless optimism

💬3 Key Quotes:

✅”Markets run in cycles: you’ve got to think of the ups and the downs. Especially if you’re doing mortgages, not 30-year holds.”

✅”People were underwriting like interest rates would stay at 2.5% forever… then rates tripled.”

✅“Temporary trends feel permanent in the moment, but in real estate, the long game always wins.”

🎧 Connect with Jason:

✅ LinkedIn

✅ https://IroncladUnderwriting.com

✅Linktree

🎧 Connect with Frank:

✅LinkedIn

🔍 Episode Overview:

In this eye-opening episode, Jason Williams and Frank Patalano dive deep into the critical principle of “trust, but verify” in commercial real estate underwriting. What starts as a conversation about mentorship and broker-provided information turns into a masterclass on due diligence. Highlighting real-world experiences with misleading offering memorandums, surprise costs, and costly omissions.

Whether you're buying a 100-unit property or a single-family rental, today’s discussion will give you the tools and mindset needed to avoid costly mistakes and make sound investment decisions. Jason and Frank cover everything from property taxes and insurance hikes to lease audits, metering myths, and Federal Pacific panel hazards.

📌 Topics Covered

✅Why “trust but verify” is a must, not just advice

✅How brokers use best-case assumptions (and why you shouldn’t)

✅Tax reassessments and insurance shockers post-acquisition

✅Hidden liabilities: leases, laundry contracts, and water heaters

✅Due diligence tactics: roof inspections, sewer scopes, lease audits

✅The danger of relying on pro formas and unverified underwriting

✅Building a third-party verification team: tax advisors, insurers, PMs

💬 3 Key Quotes:

✅"They’re showing you the tax of what they were last year, but that’s last year at a purchase price of $5 million, not when they’re selling it now at $14 million." - Jason Williams

✅ "It’s still a pig. Maybe it’s a little prettier, but they just put lipstick on it. And once it’s sold, the broker and seller couldn’t care less”. Jason Williams

✅"Even a $100,000 house can be a nightmare if you skip your due diligence” - Frank Patalano

🎧 Connect with Jason:

✅ LinkedIn

✅ https://IroncladUnderwriting.com

✅Linktree

🎧 Connect with Frank:

✅LinkedIn