I’m pretty sure that everyone who has innovated beyond the incremental has been called foolish, and that being silly is inextricably tied to chasing dreams. I find carrying oneself too seriously to be ridiculous, and staying playful and unashamed in the face of doubt to be of incalculable value.
As a sports handicapper, my dad loved making big plays on underdogs. The parallels between sports betting and investing have never been lost on me. In his spirit, I try to stay open-minded, explore investments in less-trafficked areas and discover the edge that others might not see.
I am always looking for companies that enable wider audiences of people to build and create in ways not possible before – from software development platforms to consumer apps. I’m also looking for products that have the potential to become professionals’ “third screens,” beyond a web browser and email.
There is an unstoppable movement towards transparency, accessibility and streamlined experiences enabled by technology. Industries like healthcare, law and insurance are highly lagging in tech adoption. I don’t think the millennial-and-beyond consumer will allow it to go on for much longer – there will be a tipping point in the next 5 years.
I get excited by products that are so beloved by customers that they tell their friends about them, whether they are in the same industry or not. In general, I find that not enough companies rely on word-of-mouth, customer referrals and inside sales.
I used to run creative writing workshops with middle schoolers. Getting students to be vulnerable and share their art was often challenging. One day, I tried getting one of the students to dance. We jumped, spun and waved our arms. Afterward she wrote and presented her “utopia” to our forty-person group. To this day, I do that same dance in bathroom stalls before meetings, and I still experience deep joy in empowering others to share their stories.
In the long run, the organizations that make the world a better place will generate the most market value. A technology company’s mission should start with progress, not profit.
I feel incredibly lucky to wake up every day to meet with the most knowledgeable and passionate people in their respective industries. I’m most inspired by the people who are hellbent on changing those industries and are sacrificing so much to do so.
In my prior investing life, I cold-called prospects on behalf of founders and helped negotiate partnerships and acquisitions. If we’re lucky enough to join forces and you need an extra push, I’ll also happily call job candidates, suppliers and customers, whether they’re in your pipeline or not. I’ll be your SWAT team and someone to talk to the next time you have a long, lonely drive.
What I cherish most in my interactions with founders are the flashes of personality and the moments where we help each other grow. The movie quotes in emails. Sharing advice when a family member passes away. Being told I’m wrong, and agreeing.
I knew I had to be at Sequoia when Doug recognized how I was a misfit for so much of my life. He told me about a place that celebrated individualism and eccentricity. At the time, I didn’t feel more hopeful for my career, but I did for my place in the universe.
I want to know what makes you weird.