Why did you decide to write Hopping Over the Rabbit Hole—what is the main lesson you want to impart?
Too often successful people paint a sanitized picture of their life’s journey. I wanted to write a brutally honest book about the ups and downs of business and entrepreneurship. My path to success wasn’t a straight line—it was littered with failures and setbacks. I try to share some advice in the book for people who are struggling to find their way or looking to take their career to the next level. To be successful and self-actualized, you must be willing to take risks, and with risk comes inevitable failure. You have to condition yourself to bounce back.

You started SkyBridge at a tough economic time, and acquired a Citigroup unit in even more perilous times. What’s the secret of knowing when to hold and when to fold?
I will never discount the role luck played in my career. But I also abide by the old investing adage of “be greedy when others are fearful and fearful when others are greedy.” To outperform the competition, you have to be a contrarian. Around 2008 everybody was unloading financial assets, worried that the economy and financial industry were entering a dark age. I knew that if I could stay solvent and make some strategic moves, it would be a generational buying opportunity.

You write in the book, “In business, nothing worthwhile ever comes easy”—that there are really no overnight successes. Why is it important for young people starting out in business to understand that?
Because of social media, we all see hermetically sealed versions of our friends’ lives. You see pictures of beautiful vacations and smiling babies, and you wonder why your life isn’t perfect all the time. The same goes for business—we apotheosize entrepreneurs that hit home runs like Facebook, but for every one of them, there are thousands of brilliant people toiling over less successful ventures. Don’t expect any shortcuts—understand that success involves a lot of hard work and, most of the time, not a lot of glamour.

You also write, “If you’re afraid of failure, don’t become an entrepreneur.” Most people have some natural fear of failure—how do you overcome that?
You have to condition yourself to being told “no”—and being undaunted by it. Cold calling is a great example. Most people hate it because inevitably they will be told “no” thousands of times. But I always used to look at it from the perspective of “to reach my sales goal I need one thousand no’s.” Once I framed and embraced failure as part of the process, I was able to bounce back from it without hesitation.

The business lessons you recount in your book are aimed at entrepreneurs. Who else could benefit from them?
I think the lessons I share about business also apply to life as a whole. To be a successful entrepreneur, or a happy person, you must cultivate a resilient mindset, unquenchable intellectual curiosity, and relentless positivity even in the face of adversity.