20 Lessons from 20 Years – SkyBridge Capital Turns 20

It’s been 20 years since I founded SkyBridge Capital. While I started my career in banking at Goldman Sachs – which my mother assumed was a law firm, as I’d just graduated from Harvard Law – I quickly realized the entrepreneur in me wanted more. I co-founded and ran Oscar Capital Management for five years before selling, and set off to create SkyBridge in 2005. 

I’m not sure I’d have ever predicted that 20 years later, I’d still be here (despite a brief stint in Washington). So, in honor of twenty years, I thought I’d share, in no particular order, 20 lessons learned – many of which you can find in my book From Wall Street to the White House and Back. Whether you’re just starting your career or more than 20 years in, take it from me: if you can find a learning lesson along the way, it was a worthwhile endeavor. Cheers to the next 20.

• Lesson 1: Cultivate Joy – If you’re not finding joy in what you’re doing, create it. Recognize the moments – even the small ones – that bring you the most joy at work and cultivate them daily.

• Lesson 2: Own Your Mistakes – I’ve made a lot of mistakes, but I’ve also made a point to own up to them. Owning your mistakes can be hard, but it’s necessary in order to move forward. Maybe you advised a client incorrectly or made a bad bet on something or someone. Own it. Apologize. And move forward.

• Lesson 3: Learn to Laugh at Yourself – Laughter is oftentimes the best medicine. Be the boss who can laugh at yourself and create a culture that isn’t always too serious.

• Lesson 4: Be Optimistic – As an entrepreneur, you must be optimistic. Look for the positives in all scenarios, and be solutions-oriented in your approach. It’s not always easy but seeing the glass half full when you’re starting something new, can lighten the load just a little bit.

• Lesson 5: Find Meaning – Whether in the day-to-day work or final result, finding meaning in your career helps you with lesson #1.

• Lesson 6: Read Everything – If you’ve ever seen my office bookshelves, you know I am an avid reader (check out my podcast, Open Book). Reading makes you smarter. And what client or colleague doesn’t want to work with a smart person?

• Lesson 7: Take Risks – Being an entrepreneur is all about taking risks. While it may not always pan out, if it wasn’t for taking the risk in starting SkyBridge, I wouldn’t be writing this post today. Hosting SALT in Las Vegas after the 2008 financial crisis and bringing it to New York after the pandemic were both risky ideas, but I believed in the cause. Fortunately, they paid off.   

• Lesson 8: Give More Than You Get – At its core, the act of giving is about time, love and commitment. Time is the most valuable thing you have, so be sure to give it to the people you care about most.

• Lesson 9: Have Integrity – Doing the right thing isn’t always easy, but it is always the better option. Leading with integrity builds trust with those around you and will always pay off in the long run.

• Lesson 10: Finish What You Start…But Know When to Quit – Finishing what you start is a challenge for many entrepreneurs. If you’re like me, you’re always thinking about what’s next. Coming up with the next big thing might be tempting, but you have to finish what you start. That said, you also need to know when to quit. Strategic quitting A strategic retreat is okay so long as you think carefully about the inputs and the outputs, before pulling the plug.

• Lesson 11: Know Who Your Boss Is – Anyone who influences your professional decisions, actions and performance can be your boss, even if you sit atop the org chart. Your decisions at work impact everyone around you, and it’s important to keep in mind that your “boss” will be impacted too.

• Lesson 12: Dream Shamelessly (and Often) – Don’t forget to take a step back from the day-to-day. Take time to pause, recharge and reflect on the past and imagine an infinite future.  

• Lesson 13: Keep Your Relationships – Relationships matter, and if you’ve been in the industry as long as I have, it seems like the world just keeps getting smaller. Apply lesson #8 to help maintain those relationships – give more than you get.

• Lesson 14: Have Perspective – Take the time to zoom out and bring outside perspectives to your day-to-day. Travel, read and talk to people with different views. A broader perspective helps you analyze problems and solve them creatively.

• Lesson 15: Be “Toughnice” – Don’t be a mean person, but don’t let yourself get walked over. Be kind, but also fair, and be the “tough” person everyone wants in their corner.

• Lesson 16: Be Resilient – I often refer to myself as a cockroach – I’m tough and it’s going to take a lot to kill me. Being resilient means keeping your head up even in the most challenging of times and seeing the light at the end of the (sometimes very long) tunnel.

• Lesson 17: Be On Time – This one is easy. Control the controllables. Show up ready and on time, with a good attitude, always. 

• Lesson 18: Be Secure – Own it! Be secure in yourself and your ideas, but admit when you don’t know something. Being secure doesn’t mean you have to be the smartest person in the room, it means you’re comfortable knowing you might not be.

• Lesson 19: Find Your Style – Everyone has their own style of leadership when running a team. Learn from your mentors and create a style that works best for you! Find success YOUR way.

• Lesson 20: Be Present – And lastly, be present. Take it in. Enjoy the moments with family and friends. Take time to reflect and celebrate along the way.