Introduction

Here’s the most common way of telling my story.

Robert Reffkin was raised by a single mother without much money.

He made more than $100,000 running his first business while still in high school, DJing bar mitzvahs, high school dances, and house parties.

He graduated from Columbia University in two and a half years.

He was the only student from his college class hired at the New York headquarters of the exclusive management consulting firm McKinsey & Company.

He then had a fast-paced career at Lazard, the White House, and Goldman Sachs.

He started a nonprofit at age twenty-nine to help kids who were the first in their families to attend college.

He ran fifty marathons—one in each US state—to raise $1 million for charity.

He founded his own tech start-up, Compass, which is now worth billions of dollars.

That’s the heroic way to tell my story.

But it’s nowhere near the whole story.

When my mom tucked me into bed at night when I was a child, she didn’t tell me to have sweet dreams—she told me to have big dreams. And I always have. But it’s not easy to turn big dreams into reality.

In my life, I’ve failed much more often than I’ve succeeded. The only reason I’ve accomplished anything is because I learned early how to bounce back with unrelenting energy and passion, and come up with a new dream every time I stumbled.

No matter how hard I tried to succeed in high school and college, I always ended up with a C average.

I failed to land literally hundreds of different college scholarships that I applied for.

I applied to dozens of jobs as I was graduating from college and was turned down by all of them except one.

I felt like an impostor in every job I had in my twenties, like I was one day away from being fired—and in many cases, I wasn’t wrong.

I knew nothing about running a nonprofit when I launched New York Needs You, and our first year of trial and error was a lot more error than anything else.

Our first idea for Compass failed to make renting a home more efficient for our customers, so just one year in, we had to pivot and change the entire business model.

Much of the early team lost faith in my leadership because of that pivot, and I was almost forced out of my own company.

At Compass, we’ve experimented with hundreds of offerings for our customers—software, support programs, and marketing. Most didn’t work at all.

It’s only because I’ve kept going—because I’ve been eager to learn from every challenge and keep trying until we solve each problem—that I’m here today. And because, from a very young age, I’ve never believed that the answers were inside me. I’ve always looked for answers in the work of others trying to do similar things, in the wisdom of my mentors, and in the energy of my collaborators.

I’ve learned that opportunity is everywhere around you if you’re willing to dream, ask, and listen.

The lessons I’ve learned are grounded in the journey I’ve taken. So I’d like to share some of my story—and some of the lessons people have taught me—with you in the pages that follow.

My dreams for this book

Before someone at Compass embarks on a project, I ask them, “What does success look like?” as a way to focus their energy on the results that really matter. So I’ll take my own advice and do the same.

Here’s what success looks like for this book if all my dreams for it—and you—come true.

Something you read in this book will inspire you to dream bigger than you ever have before.

Something in this book will help you realize your full potential—not just the potential you think you have right now.

Something you read here will motivate you to reach out and help someone else make their dreams come true.

And all these “somethings” added together will make this book valuable enough to you that you’ll decide to give a copy to someone you know within three months of finishing it yourself.

If all that happens, it will mean that you have come to believe, as I do, that no one succeeds alone—and that together anything is possible.

Best,
Robert