Enforcing Carve-Out or “Bad Boy” Guaranties

Enforcing carve-out or “bad boy” guaranties in real estate loan agreements—especially in Illinois and other jurisdictions that favor lender protections—requires a strategic blend of contract clarity, trigger precision, and procedural discipline. Here’s how to do it effectively: First, the guaranty must be clearly drafted, with carve-out events precisely defined. Courts have upheld full recourse liability […]

Key Legal Issues in Real‑Estate Loan Defaults

Both lenders and borrowers–no matter how sophisticated they are or how much artificial intelligence they may use–often need reminders of the key issues they need to think about. Are There Any Event of Default & Acceleration Clauses?Most commercial loans define specific “events of default” (e.g., missed payment, breach of a covenant, insolvency). Upon default, lenders […]

Drafting Carve-Out or “Bad Boy” Guaranties

Drafting effective carve-out or “bad boy” guaranties—especially in Illinois or similar jurisdictions—requires a careful balance between lender protection and guarantor fairness. Here are some nuanced tips to help you structure them strategically: Start with precise definitions. Avoid vague terms like “waste” or “bad acts” unless they’re clearly defined. Courts have interpreted ambiguous carve-outs as triggers […]

Forecasting the Key Legal Issues for SMBs in 2026

It is never too early to start worrying about how the legal world will impact your business in 2026. That said, I foresee the key legal issues in 2026 to largely mirror those from 2025. This is not intended to be a comprehensive list; rather, this is a “greatest hits” of generally applicable issues businesspeople […]

Simple Mistakes That Cause Expensive Litigation

No one is perfect. This is why many of us have jobs. However, many mistakes are avoidable. REALLY AVOIDABLE. These three cases are reminders to sweat the small stuff. Bissell Street I, LLC v. Westbrook Partners LLC (New York): Parties that co-funded and worked together in the acquisition of a $139,000,000 real estate property failed […]

Real Estate LOI Basics

Real estate letters of intent (LOIs) set forth economic terms, provide a checklist of the basic substantive terms, and serve as the starting point for attorneys to draft the formal agreements. Put differently, LOIs are the preliminary understandings of parties who intend to enter into a contract in the future “if the deal works out.’” […]

Seidman Law Group Podcast Interview

We were recently featured in a podcast: Essential Legal Strategies For Business Owners With David Seidman. Here is the link: Zero To A Hundred – Episode 25 – Zero to a Hundred – Apple Podcasts Thank you to the very impressive Jarrod Guy Randolph. You can learn more about him here: Jarrod Guy Randolph David […]

Key Considerations When Asserting or Defending Reasonable Reliance in Fraud Cases

Plaintiffs must prove that they “reasonably relied” on fraudulent misstatements of material facts to win their cases. Defendants often argue (1) the plaintiff did not sufficiently investigate the truth of the misstatements; or (2) the misstatements were so unbelievable that no reasonable person could have relied upon them. Failure to Investigate: The law does not […]

Newly Enacted Illinois Laws

I am proud to write that the Illinois legislature passed quite a bit of substantive legislation that was signed into law by Governor Pritzker. Business owners need to be aware of what new laws are passed every year. This post shares summaries of a limited number of business-related laws that Illinois companies should know about. […]

Have You Really Thought Through Your Due Diligence?

Due diligence identifies potential risks before closing a deal.  The goal is to find problems that may lead to renegotiating, reducing the purchase price, or walking away from a deal. Yet many issues remain hidden despite rigorous due diligence.  Earlier in my career I read about issues that were raised in a bankruptcy asset sale […]