What kind of deals do most investors avoid?

Usually the ones that look too complicated.

In this episode, I speak with Scott Barone, founder of Borough Management, about identifying opportunities in situations most people avoid and why execution matters more than the deal itself.

Scott shares how his business evolved from a small contracting operation into a platform operating across hotels, affordable housing, rezoning projects, and one of the largest charter school portfolios in New York.

The conversation focuses on how difficult deals are evaluated, how value is created through structure and persistence, and why controlling the process changes outcomes.

Key insights include:

• Why complexity often creates opportunity

• How execution determines whether a deal succeeds

• The importance of verifying assumptions yourself

• Why controlling more of the process reduces long-term risk

• How rezoning and specialty assets create hidden value

• Why reputation matters more than marketing in real estate

One point that stood out throughout the conversation is that most people stop when they encounter uncertainty.

The better operators learn how to work through it.

“Fortune favors the bold.”

But only if the execution holds up once the deal becomes real.

What are you avoiding because it looks more difficult than everyone else wants to handle?