Rejection Proof: How I Beat Fear and Became Invincible Through 100 Days of Rejection (2 page)

For the longest time, I had fantasized about the day I would quit my job and start a company. Now that day had arrived—and I wasn’t sure how to go about it. Should I pull a Jerry Maguire, making a loud speech in the office before storming out? Or should I do something even more dramatic, making a grand exit like the JetBlue flight attendant who quit by going down the evacuation slide of his plane?

I didn’t do either of these things, because on the day that I gave my two-week notice, July 5, I was actually scared out of my mind. My job had been a safety net for a very long time. Once I quit, there would be no going back. I was about to embark on the great unknown. Also, I felt oddly worried about my boss’s reaction. Apparently, my fear of rejection ran so deep that I was actually concerned that she’d
reject
my quitting. I didn’t want to upset her. But I knew I had to do it.
So I visualized the drawer filled with dusty blueprints—and mustered enough courage to knock on her office door.

Once inside, I stumbled through my rehearsed speech, telling her about my dream of becoming an entrepreneur. “If I don’t do it now, I will never do it,” I told her, almost pleading for her to understand and not get upset. The speech was a far cry from Jerry Maguire’s.

My boss was visibly shocked. She stared at me for what felt like minutes, and I wondered what she was thinking. She was probably contemplating what kind of insanity had come over me, that I would give up a nice income and quit my job right before having a baby. I didn’t want her to think ill of me, which felt like a kind of rejection. But I didn’t know what else to say, so I just sat there, shifting around uncomfortably.

Eventually, she found her voice. “Oh my God!” she yelled. “Who’s going to take on all your projects now? We just had a hiring freeze. Now what do I do?” I’d been afraid of her rejection, but it was clear that she had other things on her mind.

Soon after that, I started telling my friends that I’d quit my job, feeling a little surprised each time by my own words. When I made the announcement to everyone who came to our baby shower, there was an awkward silence. Instead of a pin drop, I think I actually heard a chopstick drop.

Two weeks after quitting, I walked out of that mammoth office building for the last time—saying good-bye to my salary, health benefits, 401(k), and my air-conditioned office. All my comforts—and all my excuses for not living my dream—grew smaller and smaller in the rearview mirror. I felt excited
and free, but also scared. Tracy was scheduled to deliver my son, Brian, in four days.

Holy crap
, I said to myself.
This is for real. I’d better not screw it up
.

There is no manual for building the Next Big Thing, but every start-up begins with an idea. I had been mulling one over for a while, something I believed in and that was better—and more sophisticated—than wheels on shoes. For a while, I’d been thinking about how and why people keep their promises. People make casual promises to friends, family members, and coworkers every day. What if I could develop an app that would issue some kind of points or credit for fulfilling a promise? “Gamifying” promises could potentially motivate people to keep their word, improve their relationships, and generate fun in the process. I’d spoken with plenty of friends about the idea, as well as several entrepreneurs whom I admire, and the majority of them liked the idea. Some talked to me about it for hours. Their feedback told me that I was onto something and gave me the confidence to finally—
finally!
—try turning one of my entrepreneurial ideas into a reality.

On the same day that I quit my job, I started looking for people to help me create the app. Specifically, I needed top-notch software engineers with the programming skills to write the code. (In the software start-up world, I was considered a “nontech” founder, meaning I had the idea and business expertise but didn’t have the killer programming skills needed to write the app myself.) So I started recruiting. I asked everyone I knew for potential leads. When I ran
out of acquaintances, I approached strangers at meetups and even at local basketball courts. When I ran out of in-person options, I hopped onto Craigslist and LinkedIn.

My frenetic efforts paid off. Within weeks, I’d assembled an international team of whip-smart engineers. The first was Vic, who was finishing his master’s in computer science and already had a job offer from IBM. If I could dream it, Vic could code it. The second person was Chen, a computer science PhD candidate who specialized in programming algorithms and read advanced software architecture theory for fun. Then there was Brandon, who lived in Utah and was literally a hacker. In high school he sold his own hacking software for profit. Later, he dropped out of college after his own small mobile app company became successful enough to support him. The last person, Vijay, was an engineer in India and a former colleague of mine. We’d never met in person, but I knew him to be a hard worker and a master at coding.

I was very proud of my team and honored that they believed in my vision and were willing to jump on board. Soon after hiring them, I rented space in a coworking facility—specifically designed for entrepreneurs—in downtown Austin, and we got to work. Building the app, and the business, was hard, complicated, and required long hours, week after week. But I was having the time of my life.

I was amazed by how fast a team of capable engineers could build software. We blazed our way through five iterations of product development. In three months, we built a web app and an iPhone app that felt intuitive and fun. We started using the app among ourselves and were surprised by how much our desire to keep score of our promises to one
another boosted our productivity. Of course, it’s one thing for an app’s inventors to love it. Getting outside customers to engage with a new app—in a landscape filled with mobile apps—was a much tougher sell. Thousands of apps get launched every day, and we were competing with all of them for attention. Still, it was evident we had a good concept on our hands. It might not become an instant hit, but I knew we could make it work given a bit more time.

But we needed money. Tracy and I had been married for two years by that time, and we were big savers. I had invested most of our savings in kick-starting my new venture. As personnel and operation costs piled up, those funds started dwindling. I couldn’t invest more without putting a huge strain on our finances, especially with a newborn child. Tracy had given me six months—and I needed to start showing traction to justify our investment.

Four months into the journey, it looked like my prayer was about to be answered. Our promises app had attracted the interest of an outside investor. I spent hours preparing and scripting our pitch. The team practiced it together over and over again, as if we were rehearsing for the reality TV show
Shark Tank
. The pitch couldn’t have gone better, at least in our minds. Afterward, we high-fived each other in celebration. And then the waiting began—the most agonizing wait I’d ever experienced.

It wasn’t the first time that I’d had the tense experience of waiting for others to decide my fate. When I was fifteen, I waited for weeks for the U.S. Embassy in Beijing to decide whether to grant me a visa so that I could come to the United States (I got it). When I was seventeen, I waited for BYU to
decide whether to offer me the scholarship that would mean I could afford school on my own (I got it). When I was twenty-five, I waited for an admission letter from Duke Business School (I got it). When I was twenty-eight, I waited for the yes from Tracy after proposing to her in front of four hundred classmates (the best yes of my life). Those were nerve-racking moments, with life-changing decisions hanging in the balance. But I don’t know why, in terms of anxiety level, they paled in comparison to waiting for this investment decision.

I still believed that I was destined to become a great entrepreneur. But I had just two months left to save my dream, and this investment felt like a lifeline. I wanted it so badly that I actually dreamed about getting a yes from the investor five different times, each time waking up thinking that the investment had come through. I vividly remember picking up the phone and calling my wife and family to tell them the good news in those dreams.

Several days later I was at a restaurant, attending a friend’s birthday party, when my phone vibrated. It was an e-mail from the investor. My hand started to shake, and an ominous feeling engulfed me.

I held the phone for a long time without opening the e-mail, trying to channel all kinds of positive mental energy into its content. Then I clicked it open. It was a very short e-mail. The investor said no.

I
handed my phone to Tracy so that she could read the e-mail; then I excused myself from the table and walked outside. All around me, diners were leaving the restaurant, and new groups were coming in. I could hear my friends singing “Happy Birthday” inside. Just like on July 4, I felt like a lonely, sad person adrift in a sea of other people’s happiness. Before, I had failed to take a risk. Now, I had taken a risk and failed.

I stood there in the parking lot for a good fifteen minutes, trying to control my emotions. Eventually I returned to the table, but I don’t think I said another word at the party. Tracy later told me that I looked like the kid from
The Sixth Sense
who was seeing dead people.

For months, I’d been driving to work each day feeling uplifted—like a man finally living his destiny. But the day
after the investor turned us down, everything felt different. My drive felt depressing, and the traffic unbearable. Our coworking office space, which I’d grown to love, no longer felt inviting. Even the usually cheerful office manager somehow didn’t seem friendly anymore. I had been rejected. My dream had been rejected. And it hurt.

Success no longer seemed like the sure outcome. In fact, it didn’t seem probable or even plausible anymore. I started doubting my idea:
The investor is an entrepreneurial veteran. If he thinks my company is not worth investing in, there must be some truth to it
.

I started doubting myself, too:
Who do you think you are? Who told you that you were ordained to be a successful entrepreneur? You are living a childish dream. Welcome to reality, my friend! Start-up success is for special geniuses like Bill Gates and Steve Jobs. You are just like everybody else—a wannabe
.

Then I started getting angry with myself:
What the hell were you doing? How foolish were you, giving up a good job and diving headfirst into an unknown venture?

I also felt sorry for Tracy, convinced that I had let her down and that she’d be so disappointed in me.
You see how painful that was? Are you going to go through all that and get rejected again? No way!

Finally, I started getting scared:
Now what? What are your friends going to say? Your in-laws? They probably think you’re irrational and an irresponsible husband and father—and maybe you are
.

The problem with insecurity is that you start feeling like everyone might reject you, even your closest loved ones. My first day back at the start-up after the investor’s rejection was
dismal. When I got home that night, I felt compelled to apologize to Tracy. I told her I was sorry that I’d failed, and that I was beginning to think that the start-up life wasn’t for me. I suggested that I might cut my losses and start looking for a new job a few weeks earlier than I’d planned, so that we could get the income flowing again.

When I finished talking, I looked at Tracy, expecting her to walk over and hug me in sympathy. Instead, I got a wake-up call. “I gave you six months, I didn’t give you four,” she said. “You have two months left. Keep going and leave no regret!” I was ready to give up, but Tracy had another idea. She was fired up, like a pissed-off quarterback who grabs the offensive lineman’s face mask and screams into it after he gives up a sack. It was another “I realized I married up” moment.

I agreed that I would stick it out for two more months—and that during that time I would do everything in my power to lift my idea and my company off the ground.

But the funding debacle had left me terrified of the next rejection. I wanted to pursue other investors, but I felt stuck in fear that they’d all say no and my dream would die. When I looked at myself in the mirror, I saw an ambitious guy who couldn’t handle rejection. I’d spent years working in a safe corporate environment and hiding from risks inside a team. I wasn’t used to putting myself out there. If I really wanted to be an entrepreneur, I needed to get better at dealing with
no
. Would Thomas Edison, Konosuke Matsushita, or Bill Gates have wanted to quit after only four months? No way!

I had two months to improve the app and find additional investment. But I realized that I also needed to find a way to
become stronger when facing rejection. I needed not just to overcome my fear of no but to learn how to thrive in the face of it. If I was David, then rejection was my big, hairy Goliath. I needed to find the right tools, the right armor, and the right slingshot and stone to take him down.

I started with the most high-tech weapon in my arsenal: Google. I typed “overcoming rejection” into the search box and quickly scanned the results: a how-to article, a bevy of psychology articles, and a smattering of inspirational quotes. None of them called out to me as a solution to my problem. I wasn’t interested in counseling or bits of inspiration. I wanted action.

After meandering through a series of links, I stumbled upon a website devoted to something called Rejection Therapy—a game of sorts developed by a Canadian entrepreneur named Jason Comely, in which you purposely and repeatedly seek out rejection to desensitize yourself to the pain of the word
no
. For some reason, I fell in love with the idea. It reminded me of the ancient Iron Fist technique in kung fu, where a person repeatedly pummels hard objects with his or her fist to gain resistance to pain.

Maybe I’ve seen too many kung fu movies, but the idea of overcoming rejection by throwing myself at it again and again and again held an odd sort of appeal. This was exactly what I needed—an Iron Fist approach to rejection. In an over-the-top move reminiscent of my teenage promise to conquer Microsoft, I made a vow not only to try rejection therapy but to do it one hundred times, video-record the entire
experience, and start a blog on the topic. I found a domain name called
FearBuster.com
. There I would start my blog, which I called “100 Days of Rejection.” I had never blogged before. But I liked the built-in accountability that blogging seemed to promise. If I managed to get any followers, then it would be hard to quit halfway.

Comely’s game sells a deck of cards preloaded with tasks that players can do each day that will likely lead to a no—things like “Friend a complete stranger on Facebook” or “Ask for directions from someone on the street.” But to me, these sounded too tame. If I was going to do this, then I wanted my rejection attempts to be creative, maybe even a little bit crazy. I also wanted them to be uniquely my own. I figured this might inject a little fun into a task that pretty much terrified me.

The next day, my rejection journey began.