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