Leading Through Risk, Failure, and AI: Adam Massaro on Building a Winning Legal Practice

Success in business often means making tough decisions when the outcome is not guaranteed. For trial attorney Adam Massaro, learning how to manage risk, prepare for different outcomes, and stay willing to fail has been a major part of building his career.

In this episode of the Mile High Success Podcast, Nick Elder sits down with Adam Massaro, a litigation partner at Reed Smith who helped launch the firm’s Denver office.

Adam shares how his career grew alongside Denver and how he went from building a broad corporate litigation practice to helping establish the Denver office of a global law firm. He also talks about the responsibility that came with bringing members of his team along for that transition.

Nick and Adam explore what separates great attorneys when technical skill alone is not enough. For Adam, one of the biggest differences is being able to connect with clients on a human level. Litigation can last for years, and clients often face major decisions with uncertain outcomes. Adam explains why strong, clear advice and honest conversations are so important.

They also discuss Adam’s approach to risk. Before going to trial, he thinks through multiple possible outcomes and builds different paths forward. That same idea carries into leadership: prepare for Plan A, but be ready for Plans B and C.

Adam also shares one of the biggest challenges he has faced as his practice has grown: learning how to scale without becoming the person who has to make every decision. He explains why leaders need to trust their teams with meaningful responsibilities so those people can grow.

The conversation also covers Adam’s daily habits, his decision to stop drinking alcohol in 2020, his use of cold exposure, and the role failure has played throughout his life and career.

Finally, Adam explains how artificial intelligence is changing litigation. Rather than using AI only to review documents or research case law, Adam uses it to test arguments, identify weak points, explore different scenarios, and “war game” cases before making important decisions.

Adam’s message is simple: if you spend your life trying to avoid every failure, you may also avoid the risks that create your biggest opportunities.