From Childhood Hustles to Entrepreneurial Insights

What a conversation! In this episode of OGs of Playmaker Original presented by DraftKings, I sit down for an unfiltered, wide-ranging talk about where I came from, what shaped me, and why I see the world the way I do today.

We go deep on my childhood as an immigrant kid from the USSR, growing up in Queens and New Jersey, and how the adversity I faced gave me a hunger that shaped my whole career. I share stories about building my dad’s liquor store into a $60M wine business, spotting the early days of YouTube, and the lessons I learned (and big misses!) as an angel investor in companies like Twitter, Facebook, Snapchat, and yes, even Uber.

We also dive into how I read culture, stay ahead of trends, and why mixing up your circle is the secret sauce to learning and winning long-term. And of course, we chop it up about the Knicks, Jets, and how New York sports fandom is religion for me.

This one’s raw, real, and packed with mindset shifts for anyone who wants to build, bet on themselves, and stay hungry.