Overcoming the Fear of Failure with Chrys Bader
A conversation with three-time startup founder Chrys Bader
Hi Grand Fam,
Today's Grand Time is about taking the leap to start a company, and managing the fear and anxiety of the unknown as a startup leader.
Chrys Bader is currently the co-founder of Ikaria, a startup who's mission is to increase social wellness through technology. He was formerly the co-founder of Secret, an app for more authentic sharing amongst friends, and has built many products at Google, Youtube, and other tech companies.
Tell us about your career journey. What drew you to become an entrepreneur?
When I was 13, I was playing text RPG video games, I wanted to edit them and make my own worlds. That led me to download some source code and start pursuing my own projects. I've always been a wandering artist, following my curiosities, and prioritizing what excited me over money. That's been a theme throughout the the choices I made.
In 2007, my friend and I were working on a project and joined Y Combinator. I moved to San Francisco, and that was the first time I was able to discover a community. I was previously in Boston, where you didn't really find a lot of people building websites or apps at the time.
Finding a supportive community and learning there's other people like you going through the same thing, really changed my life forever. That's why I love The Grand and the way you are bringing people together for shared experiences.
This is your third-time starting a company, how did you approach starting a company now versus your first and second company earlier in your career?
Starting a company this time was very difficult, especially after having an optically successful company. I suffered from imposter syndrome and felt people had high expectations for me. I had to overcome the fear of what the world might think if I fail.
That's why this time around, I had to work on a mission I could die on a hill for.
The key lesson for me was, if you work on something you truly believe in, you will never feel shame. Because you know what you're doing is aligned and congruent with your values. If you really believe in a cause, surround yourself with likeminded people, immerse yourself in their energy, and find support from the community.
How did you move past imposter syndrome and the fear of things not working out?
It comes down to self love. Being aware of the inner dialogue you have, and asking yourself whether or not that's healthy is the first step.
Another way to look at it is, if your friend says they're going to start a company, would you immediately tell them, "Oh you're gonna fail, and then everyone's gonna laugh at you?" If you wouldn't say that to your friend, why would you say that to yourself?
Now when the fears come up, I fill myself with more self-compassion. I say to myself, "You're doing your best. It's okay if it doesn't work out, you're going to learn a lot." Changing the dialogue with myself has been critical.
How did you establish the values of your team and company?
My co-founder and I built a timeline of all the decisions we made across the board. Then we asked ourselves, what value is expressed in that?
If you don't know what your values are, look at history. Write your down your decisions, analyze them, understand intrinsically what you're expressing by the decisions you’ve made.
We do this quarterly now in our team retro. We build out the timeline, we put pictures and screenshots on there to make it fun like a scrapbook, and we share that with the team. Then we ask questions like, "What do we learn? What are the values that are being expressed?"
Thank you Chrys for sharing your experiences, frameworks, and philosophies with us.
We hope this conversation gave you more self compassion, and the inspiration to overcome your fears.
The Grand community is here to provide support and guidance as you’re navigating big decisions. Join the upcoming Grand Quest on Becoming an Effective Manager or Making a Career Transition.
💌,
Rei