250 Million Dollars and Four Lessons on Resilience

Today we’re announcing that the company I co-founded, Omaze, has grossed $250 million for charity. We raise money by offering the chance to win once-in-a-lifetime experiences like being mentored by Michelle Obama or winning a Lamborghini where Pope Francis hands you the keys. Along the way, we’ve earned 3 billion video views and donors from 180 countries.

That’s the stuff we publicize.

We don’t publicize that our first experience raised $784, that we made so many mistakes after series A that we had to lay off 25 teammates we loved in one morning, or countless other failures.

Successful entrepreneurs are often portrayed as superheroes. When stories of their achievements are told in reverse, it seems as if every move was orchestrated with courage and prescience. Even when failure strikes, it’s transformed into a launchpad for success.

That has not been my experience. At many times I felt hopelessly lost and lonely. Only when I became vulnerable about my fears was I able to learn from the people with the wisdom to help me get through the dark times

I’m writing to let you know that if you’re scared that the obstacles to your dreams seem insurmountable, you’re not alone. I wouldn’t have been able to make it this far without the lessons below. And if I was able to find a path, so can you.

Everyone is scared.

Our big break came in our second year. Disney had just acquired Lucasfilm for $4 billion. After months of meetings, it agreed to partner with us on an experience for UNICEF where the winner would get to be in a Star Wars film. What Disney didn’t know was that we were only six people and didn’t yet have the resources to pull it off.

From the outside, people saw this fearless group that took a big swing. Inside, we were terrified throughout the whole journey, living in near-crippling anxiety that we’d fail publicly.

The bouts of fear used to leave me worried I didn’t have the constitution to be an entrepreneur. Over time, I’ve learned that every entrepreneur, no matter how successful, faces existential crises.

Mavericks like Branson and Musk don’t make bold choices because they’ve eliminated fear, but because they’ve developed a mindset to get to the other side of it. They recognize fear is simply stress caused by the imagined consequences of a future state that only exists in our minds. You don’t need to be fearless to be great. You just have to turn down the volume on the worries enough to focus on the task at hand.

Practice: When you’re scared, ask your 80-year-old self for advice. They don’t overthink short-term consequences. They know that whatever happens, there will be an opportunity to adapt. The more you practice, the better you get. And your 80-year-old self is a great trainer.

The greatest fuel for persistence is serving others.

I once asked President Bill Clinton for advice on public speaking. He told me that it’s important to make it about the people you’re speaking to. Whenever you make it about yourself, you’re more likely to fail. This lesson applies to most things.

We only take the entrepreneurial leap because we believe we can build an impactful business. Naturally, when we face challenges, we look inside for the strength to overcome. Sometimes it can be better to look outward.

When we hired our first employee, I suddenly realized that if we failed, it wouldn’t just impact me, but her and her family. I was initially terrified. But ultimately, writing down how my actions could serve our team and partners unlocked a well of inspiration I couldn’t access for my own benefit.

Practice: Dedicate daily actions to someone, just like people dedicate books. Our brain releases serotonin and dopamine when we know our actions benefit another. Journal daily about how your work will serve, and you’ll unlock a reservoir of energy.

When you don’t know what to do, do nothing.

Entrepreneurship seemingly requires perpetual motion. You’re either full steam ahead, or you’re dying. But with inflection point decisions, you can’t just crank up the intensity to get to your answer.

The importance of following your gut is well documented. We have 500 million neurons in our stomach, and the somatic messages they send to the brain provide critical input. But when stakes are high and accomplished advisors are offering conflicting guidance, it’s hard to find that intuition. I’ve made costly mistakes by allowing others’ voices to drown out my own.

That’s where doing nothing comes in. Finding the space to be still is invaluable. It empowers you to clear the noise and reconnect to your deeper wisdom.

Practice: First, allow yourself the time to do nothing. When big decisions are on the line, there is pressure to move quickly. Resist. Once you take the time, the usual suspects can help: meditation, nature walks, exercise. Visualizing the alternative outcomes and journaling as if they’ve already happened is also helpful. By deeply imagining your future state, you can reconnect to that initial intuition.

Gratitude is your best friend.

Our early days were far from successful. On one particularly bad day, our only developer quit, an investor rescinded his promise to bridge and we were told we’d lost the Breaking Bad campaign we thought would save the company.

That’s when I was advised to start a gratitude journal. It seemed counterintuitive, given everything that could go wrong had gone wrong, but it helped me reframe these experiences. I was grateful for the time we’d had with the developer, that we’d learned about the investor before it was too late and that we could develop a plan to win Breaking Bad back.

Our brain performs better when operating with a positive mindset than when negative, neutral or stressed. Practicing gratitude trains you to look for the positive in situations and absorb lessons more deeply.

Practice: Write down three things you’re grateful for nightly. Then, start choosing one person each week, and write an email sharing your gratitude for them. I’ll start. I’m grateful to you for reading this article.

Co-Founder & CEO @Omaze. Dream the world better.