Ep.1 - From Investment Banking to Building a Finance Company with Matt Milim

In this episode of High School to Wall Street, Tyler and Parker sit down with Matt Milim, a former investment banker, hedge fund investor, and entrepreneur.Matt shares how he broke into investment banking and why it’s one of the most powerful ways to build a foundation in finance early in your career. He then walks through his transition to the hedge fund world, where he spent nearly 14 years analyzing companies and making investment decisions in real time.The conversation takes a deeper turn as Matt explains why he ultimately left Wall Street to start his own business, Probate Advance, and how he navigated the challenges of entrepreneurship—from early failures to scaling the company and eventually selling it.Matt also shares insights on litigation finance, helping people access money during long legal processes, and how his work today connects to real-world impact.In this episode, we cover: What investment banking is really like (hours, skills, and learning curve)  Hedge funds vs. private equity vs. startups  The story behind building and selling Probate Advance  Early-stage business challenges and how to overcome them  Why persistence is the most important trait for success  Advice for high school and college students interested in finance Whether you’re interested in Wall Street, investing, or starting your own business, this episode is packed with practical insights and real-world lessons.