CHAPTER 1
TAKE THE LEAP
Itâs scary looking down. Especially when thereâs a lot at stake.
You know those decisions that make your heart race and your palms sweat? The ones that are so overwhelming you start asking yourself, how in the world did I even get into this position in the first place? I do. Iâve felt that way many times before. Iâm a successful entrepreneur now, but that wasnât always the case. I had to take a lot of risks and leap off a lot of cliffs to get here . . . and even now I still get that heart-racing, palm-sweating sensation before I jump into a new adventure.
Every great story starts with a jumpâa risk, leaping into the unknown, not knowing exactly how you will land. Whether youâre jumping from a place of greatness, from rock bottom, because youâve hit rock bottom, or youâre simply stuck, you can absolutely create positive, transformative change in your life. You just have to be willing to trust yourself and take the leap.
THREE REASONS TO JUMP
Before you dive in, itâs important to know what type of jump you are taking and why. As a seasoned jumper, Iâve noticed that there are three main reasons people take big leaps.
Reason #1: You Have No Other Choice
The Survival Jump. You are forced to change. Youâve been fired, bankrupted, or had a life-changing event, or some other environmental force has you in its clutches. This is less of a choice and more of an emergency exit.
Reason #2: You See an Opportunity
The Opportunity Jump. You want to change because you have a vision. You see a way to improve your life through bold action. Youâre stable or relatively happy now, but you have big dreams, a business idea, or a vision of how you want your life to be. You feel certain you are meant to do something bigger.
Reason #3: Youâre Stuck
The Stagnant Jump. Youâre considering a change because youâve stagnated, are bored, or feel unfulfilled. Youâve reached a certain point in your career where you arenât sure what to do next. You feel comfortable but not challenged. Think of it as a plateau. You stay put because that feels easier than jumping into the unknown.
Hereâs a little secret: your reason for jumping doesnât matter; the only thing that matters is that you have the courage to take the leap.
SURVIVAL JUMPERS
The Survival Jump I was forced to take early in my career felt like the worst thing that had ever happened to me, but it turned out to be the best. It was the catalyst that changed the course of my life for the better. And between us, I wouldnât be writing this book if I hadnât taken that Survival Jump.
Picture this: Iâm twenty-two years old, living in sunny Los Angeles, living in an apartment with my two best friends. Iâd just landed my dream job at a new tech startup. It was the peak of the internet bubble, when any company with a â.comâ was a hot commodity. I was on top of the world. I was elated and convinced that Iâd won the lottery with a new job that would help me thrive and grow during the first stage of my adult life. It was an era of abundance. The money being poured into internet companies was skyrocketing. Big fancy offices, flashy cars, 24/7 parties with champagne and sushi; it was a college gradâs dream. The future seemed limitless, and I had a golden ticket.
I was so excited about the opportunity that I convinced my closest friends to come work with me. Unfortunately, the fantasy and promise of this new job and incredible company didnât last long. The company was a precursor to Dropbox (just a decade too early). Data storage costs were high, customer adoption was extremely slow, and our expenses outpaced our revenue. While the advertising division of the company was experiencing impressive levels of growth, the companyâs core business was bleeding money. Iâd worked tirelessly building and running our digital ad sales teamâworking late nights and weekends, pouring my heart and soul into my workâbut our success wasnât nearly enough to keep that sinking ship afloat. With no cash and a failing business model, I was forced to fire all my friends right before I was fired myself. My âdream jobâ quickly turned into my worst nightmare.
Suddenly I was unemployed, broke, and devastated. I was convinced Iâd reached my lowest point. I went home, turned off the lights, crawled into bed, and cried. I donât think I left my room for days. My roommates tried to cheer me up, but I just wanted to be alone. I ate more tubs of Ben & Jerryâs than Iâd like to admit. I called my mom every day to share my disappointment and fear. Every day, I questioned what I was going to do with my life and wondered if I was a complete failure. Iâd hit rock bottom.
Even in the face of all that bleakness and disappointment, I knew if I stood stillâif I let my fear and disappointment consume meâmy entire future would be in jeopardy. I needed to get my life back on track and take control of my destiny. I was gearing up for the most transformative jump of my career.
Up until this point in my life, every jump Iâd taken had been a proactive choiceâOpportunity Jump. I was accustomed to taking calculated risks when I saw opportunities or felt ready for a change. (That trait is in my DNA. Itâs something Iâd been doing naturally since I was a kid.) But the jump I was about to take was different. It was completely reactive: a Survival Jump. The rug had been ripped out from underneath me, and I had to make some huge changesâand make them fast.
Knowing myself, I recognized that letting this setback derail my life completely would cause me more fear, angst, and misery than gathering my courage and taking a big risk. One late night, eating pizza with my roommates, I made a joke about starting my own business. But my two best friends didnât laugh; they thought it was a great idea. Which made me genuinely ask myself, wait, what if I did?
Even though Iâd grown up in a family of entrepreneurs, Iâd never thought of starting my own business before that moment. As a new college grad, I believed that working for an established company was the most secure path to success. I had been on the entrepreneurial roller-coaster ride with my father growing up, and I didnât like the unpredictability and constant letdowns that came along with it.
I knew better. There were no guarantees, whether you worked for yourself or someone else. This was the hardest lesson. The only thing I knew was I had to try something different. So I started thinking about launching my own digital advertising company. Digital advertising was becoming more mainstream, and even though my startup employer had imploded, the digital advertising division had been solid. Moreover, I was good at it and I loved doing it. I decided to go all in on the digital ad trend. I had built up a solid client list of advertisers, I had experience running a team, and I had serious hustle.
I chose to ignore my excuses. Sure, I might fail, but I had failed already. So, if I was going to fail again, it was going to be on my own terms.
When I started telling more people about my business idea, the reception I received wasnât exactly enthusiastic. And what I mean by that is . . . most thought I was making a massive mistake. I was told I was too young, I had no experience running a company, the timing was wrong, the idea was outlandish, and the chances of success were slim. The adults I told were even more conservative; they said I should scrap my idea, play it safe, and go get a ârealâ job. (Which confused me because the job Iâd just gotten fired from was ârealâ!) Looking back, that makes perfect sense: the market was a graveyard of failed internet companies, the entire economy was in rough shape, and my track record wasnât exactly overflowing with wins (yet!).
Maybe I was crazy. I definitely have a streak of craziness. But thatâs what gives me confidence. In the face of all that uncertainty, I still believed in the opportunity.
Although the dot-com crisis was a wake-up call, I still believed in the potential of a digital business. People assumed that when the bubble burst, the internet was dead too . . . but very soon afterward, it became more popular than ever. Everyone I knew was spending more and more time online; even my grandma had an AOL account! My gut told me that if I could muster up the courage to start my own business nowâwhile everyone else was fleeing from new endeavors and startupsâI had a shot at success. I could let the circumstances of the world define me, or I could take my career and destiny into my own hands and create the future I wanted. I chose the latter. I sat down at my kitchen table, set up my home office, and took the jump that started my journey into entrepreneurship.
It wasnât an easy journey, nor was it a straight line to success. In fact, the line looped up and down with frightening unpredictability, but I wouldnât trade that roller-coaster ride for anything. It was the wild and winding path that shaped me, taught me, and turned me into an entrepreneurâand human beingâwho embraces opportunity and always chooses to jump rather than stand still.
And it all started because I hit rock bottom.
That lonely, hopeless place is where so many find themselves at some point in their lives. Iâm sure many people around you have felt this wayâduring the recessions of the dot-com bust in the early 2000s, the 2008 financial crisis, and, most recently, the COVID-19 pandemic that caused an unprecedented global shutdown. Rock bottom is a place that plenty of people have been before.
And if thereâs just one piece of wisdom I want you to take away from this book, itâs this: if youâve got to jump, rock bottom is a great place to start. After all, thereâs nowhere to go but up.
The Survival Jump is just one way to jump, but you donât need to be pushed off a cliff to make a life-changing leap.
OPPORTUNITY JUMPERS
Nancy Twine is an incredible example of someone who recognized an opportunity and jumpedâbig. After a seven-year career at Goldman Sachs, she took an Opportunity Jump and left her high-paying Wall Street career to become the CEO of Briogeo Hair Care, now one of the fastest growing hair-care brands at Sephora.1
Nancy had been creating her own homemade organic hair-care products for years, using recipes inspired by her grandmother. She found that the hair-care industry was underserved, and she saw that there was opportunity for a newcomer. So she jumped at the opportunity. Nancy presented her products at a beauty trade show and received her first round of purchase orders from retailers like Urban Outfitters. Six months later, Sephora called.
âI know how discerning the merchant team is at Sephora, and having their buy-in to my wild idea really meant a lot to me,â said Twine. âI knew that this was my big opportunity, and I had to go for it.â2
Nancy took the Opportunity Jump to become a clean-beauty entrepreneur and followed her dream of pioneering a transformational brand for all hair types and textures. She is projected to generate $40 million in sales in 2021.
Nancy began with zero experience in the beauty industry, but she has since become a leader in green beauty and the youngest Black woman to launch a line at Sephora. Nancy continues to pay it forward, elevating other founders and women of color by mentoring and advising young entrepreneurs through Sephoraâs Accelerate incubator program.
Like most of the entrepreneurs I know, Nancy had the power of seeing something not as it is, but as the potential of what it could be.
STAGNANT JUMPERS
Chances are that if you are stagnant, you already know. If you dread Mondays, live for the weekend, or have to force yourself out of bed; if you are stuck or bored out of your mind; if you are miserable in your job or see no upward trajectory in your career, youâre probably a Stagnant Jumper. Letâs address the dangers of stagnation. Itâs clear that stagnation is the exact opposite of what youâve set out to achieve by reading this book. We all know monotony is the death of creativity.
In my experience, thereâs no growth in the comfort zone, and if you want to overcome stagnation, you need to change.
Let me prove it to you.
A decade after starting my company from my kitchen table and selling it to Singtel, one of the most prestigious telecommunications companies in the world, I decided to take a jump and step down as CEO.
Itâs never easy to leave a company, especially one that you built from the ground up. I loved my job, the ever-changing environment of the digital world, and the company I worked for. I loved my team of over one thousand talented colleagues a...