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:
- Be a great storyteller. The three jobs of a CEO are: setting the vision; recruiting talent; and making sure there’s money in the bank. All three require an ability to spin a yarn that will transfix others.
- Always overdeliver on the product. It’s no fun selling a product you don’t love. As the CEO, you are the last line of defense on the standards set by your company. Focus on building a tremendous product or service, and the rest will follow.
- Be a people person. Relationships are everything in life. Show compassion to your team, and care about others and their lives. Treat everyone like they matter, because they do. Those nights when you’re stuck in the office all by yourself trying to deliver a product, you’ll see if you’ve really brought others on board for the ride. You don’t want your team to consist only of mercenaries. Build the bonds that matter.
Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?
- Your vehicle is more important than your driving skill. The biggest determinant of success in your career is the vehicle you choose to ride in. You can be mediocre in a thriving industry and still succeed. But it’s supremely difficult to succeed in a dying industry, even if you are world-class.
- Build your network sooner, rather than later. Many young careerists are shy about building their network. I used to be as well! Competing in the academic world I grew up in, I figured everything was a meritocracy. As I’ve matured, I’ve realized that the rules are different later in your career, and it can be both fun and rewarding to build relationships that are business-driven and mutually beneficial.
- Get technical. In this day and age, you have to learn to code. Go to a coding bootcamp, take an online course, or just research on Google. Non-technical founders get so frustrated with engineers, but it’s really their own fault when engineering work goes sideways.
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!