Episode Overview:

In this episode of The Ironclad Underwriting Podcast, host Jason Williams sits down with Frank Patalano to unpack the many layers of risk in real estate investing. From financing challenges and market shifts to tenant turnover and operational missteps, they explore how each factor can influence an investor’s long-term success.

Jason and Frank discuss why financing risk often peaks at refinance rather than at purchase, especially in today’s high interest rate environment, and how smart contract structuring and proper underwriting can make or break a deal. They also talk about the realities of running properties through changing market cycles, the importance of strong management teams, and why having the right systems and people in place can minimize operational setbacks.

Topics Covered:

• Market risk and how economic trends affect investment performance

• Tenant and resident risk in varying market conditions

• Financing risk at purchase and refinance stages

• Operational risk from management and maintenance challenges

• Liquidity risk and the importance of cash reserves

• Location and economic risk tied to neighborhood and policy shifts

• Valuation risk and the dangers of overestimating property performance

• Legal and liability risk and how to protect assets

Key Quotes:

• “Financing risks often come at refinance time, not at purchase, because by then the market may have changed and your options are limited.” — Frank Patalano
• “Good underwriting is not about predicting the future. It is about preparing for what could go wrong and knowing how to pivot when it does.” — Jason Williams
• “Every deal has risk. The question is whether you understand it well enough to manage it.” — Frank Patalano

🎧 Connect with Jason:

✅ LinkedIn

✅ https://IroncladUnderwriting.com

✅Linktree

🎧 Connect with Frank:

✅LinkedIn

Episode Overview

In this episode, Jason Williams and recurring guest Frank Patalano break down one of the most overlooked truths in real estate: you can’t do it all yourself. From accountants to attorneys, property managers to insurance brokers, your success depends on the strength of your team. Jason and Frank share real stories, costly lessons, and the systems they use to make sure every deal is backed by the right people.

Whether you’re underwriting your first deal or scaling a portfolio, you’ll walk away knowing which professionals are indispensable, how to choose wisely, and why cutting corners with the wrong advisor can sink your investment.

Topics Covered

• Why property management will make or break a deal
• The essential advisors every investor needs on their side
• Accountants vs. bookkeepers (and why both matter)
• How tax advisors can save you thousands with the right strategy
• The role of insurance brokers in protecting your assets and underwriting deals
• Working with real estate brokers for deal flow and insights
• Why attorneys (love them or hate them) are critical for contracts and compliance
• Inspectors, contractors, and the importance of due diligence teams
• Lenders and lending brokers as your biggest financial partner

Quotes from the Episode

💬 “Property management will make or break a deal. You can have the best business plan in the world, but without good management, it’ll sink.”

💬 “Sometimes it’s better to be vacant than to have a bad resident.”

💬 “Your lender is often your biggest investor. If they’re covering 70–80% of the deal, you’d better make sure they’re on your team.”

🎧 Connect with Jason:

✅ LinkedIn

✅ https://IroncladUnderwriting.com

✅Linktree

🎧 Connect with Frank:

✅LinkedIn

Overview

In this episode of the Ironclad Underwriting Podcast, Jason Williams and Frank Patalano dig deep into the concept of stress testing in commercial real estate underwriting. They explore why sensitivity analyses are critical, how assumptions around interest rates, exit cap rates, hold periods, and expense ratios can make or break a deal, and the importance of preparing investors with realistic projections. Through real-world examples, they highlight lessons learned, common pitfalls, and practical ways to build more resilient underwriting models.

Topics Covered

• Why stress testing and sensitivity analyses are essential for conservative underwriting

• The impact of interest rate volatility and cap rate assumptions on deal performance

• How to stress test hold periods, rent growth, and stabilization timelines

• Using expense ratios to prepare for realistic operating costs

• Communicating scenarios with investors to build trust and confidence

Quotes

• "Who would have thought interest rates would have tripled in nine months? Nobody. That’s why you have to stress test."
• "You don’t want to underwrite cap rate compression—you want to underwrite cap rate expansion. If you end up with compression, that’s just gravy."
• "Improvement, not perfection. Each deal teaches you something new that makes the next one stronger."

🎧 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 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