Adam: What is something about you that would surprise people?
Hamilton: I was Kobe Bryant’s corporate lawyer. Back in the early 2000s, Kobe was interested in purchasing a basketball team in Italy. It’s where he grew up and where his Dad played professional basketball. Growing up in Los Angeles and being a huge Lakers fan, it was awesome to meet Kobe and work with him on this deal. I found Kobe to be highly intelligent and, contrary to his public persona, quite approachable. I remember he laughed at my jokes!
Adam: How did you get here? What failures, setbacks or challenges have been most instrumental to your growth?
Hamilton: I took a windy career path to get where I’m at today. Having attended Harvard College and Harvard Law School, and having worked as an investment banker at JP Morgan and a corporate lawyer at an elite law firm, the career road in front of me was paved with financial security. But I couldn’t bring myself to do work that I didn’t find personally fulfilling. I wanted to use all of my dimensions – my creative side, my interpersonal side, my risk-taking side – not just my research and writing skills, in my career. So I dove off the deep end and became an entrepreneur. Fourteen years later, I found myself running two businesses simultaneously, and while I loved being an entrepreneur, it was also crushing me. I was truly uncertain whether I would be able to come out on top. After I achieved a successful exit in 2016, I decided to help other entrepreneurs deal with the stress of being a founder, and that started my executive coaching practice. Now, as a Professor at Loyola Law School heading LLX – our new online Executive Education program – I have the chance to share these and other lessons with many businesspeople across the globe.
Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?
Hamilton: Having been an executive coach now for more than 200 Y Combinator founders (YC is a venture fund that funded my tech startup), I think there are three critical qualities of an effective leader:
Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?
Adam: What is the best piece of advice you have ever received?
Hamilton: Be likable. When my Dad and I worked side by side, he always said, “Do you know why people buy from me? It’s because they like me.” Sometimes, likability gets a bad rap. It is true you can’t be an obsessive people pleaser, but when who you are comes from a genuine place and you just like meeting people – something true of my Dad and of myself – the world starts to open up for you. Seek connection with people in everything you do, whether it’s getting a cup of coffee and talking to the cashier or reaching out to someone in your industry who can help you out. Be a people person, and watch your world respond in kind.
Adam: What is one thing everyone should be doing to pay it forward?
Hamilton: Answer emails and calls from those seeking advice or mentorship. There’s nothing more deflating than not getting a return call from someone you truly admire. As a potential mentor, you have the opportunity to deliver an outsized return on another person, because you already have their ear. This is part of what has driven me to be a coach and to launch Loyola Law School’s Executive Education program. As lifelong-learning becomes the default mode for all professionals, we can pay it forward by mentoring and teaching the next generation.
Adam: What are your hobbies and how have they shaped you?
Hamilton: I have a renewed interest in tennis and a newfound interest in golf. I also rekindled my desire to play piano. All of these things I had to do as a kid, I didn’t enjoy. And of course now that I don’t have to, I suddenly love it! I also love that I can enjoy these activities now with my children. This has shaped me in that I now realize I am truly a lifestyle and relationship guy first and foremost. It’s what drives me.
Adam: Anything else you’d like to share
Hamilton: If you find yourself in a situation where you are stressed out or over your skis, find someone objective to talk to. There are resources everywhere now. I happen to be involved in executive coaching and executive education, but there are many other forms of advice and mentorship out there. Bring on a wingman and solve the world together!