Pragmatic Optimism

To my friends and colleagues, I’m known for staying calm under pressure. Stress hardly seems to faze me, and I carry an air of confidence that sometimes borders on cockiness (though no one’s ever said I’ve crossed that line). But beneath this composed exterior is a whirlwind of thoughts and emotions that I’ve learned to process internally.

In the coming months, I’ll be embarking on a journey I’ve never taken before: becoming a founder. It’s a path filled with unknowns, and if you listen to most founders, you’ll hear an endless litany of reasons why it’s a terrible idea. A few months ago, I was chatting with a friend who’s a repeat founder. I told him how I was both excited and terrified about starting something from scratch. He asked me what I was afraid of, and as I’ve had more time to reflect, I decided to write those fears down — not just for myself, but in the hope that others in similar situations might recognize that they’re not alone.

The more I spoke with other founders, the more I realized that these fears aren’t as unique as they might seem. Everyone has their own set of anxieties, and the key difference lies in how openly we discuss them.

So, here's my unfiltered list of founder fears, in no particular order:

Irrational optimism: The best founders I know believe that anything is possible. They tackle challenges with unbounded optimism, pushing through when others say it can’t be done — and they’re usually right. Can I cultivate that kind of optimism, or can my pragmatic, hyper-rational approach still succeed?
Vision: Great founders are guided by a clear, long-term vision and have mastered the art of working backward from it, inspiring others along the way. In most businesses, a handful of key decisions can dramatically influence success or failure. Get them right, and you increase your chances of success. Get them wrong, and recovery is nearly impossible. I’ve so far been an operator, someone who executes someone else’s vision. Can I craft a compelling vision and turn it into reality?
Seeking rejection: Founders must become rejection magnets, constantly putting themselves out there despite the high likelihood of hearing "no." Can I not only tolerate, but actively seek out these situations, knowing that the rare "yes" could be transformative?
Traveling: With my co-founder in San Francisco and me in Los Angeles, not to mention the need to meet customers face-to-face, how will I balance the demands of travel with my family life? Will a move back to SF become necessary? And how will that impact my loved ones, especially my daughter?
Jack of all trades, master of... all?: Founders wear many hats, often learning entirely new skills on the fly. Will I be able to learn quickly enough, picking up the essentials of every business function before even considering hiring experts?
Creativity: I've never considered myself an "ideas person", and been fortunate to work with people who are much more creative than I am. Can I cultivate this skill through networking and osmosis, or is it an innate trait that successful founders must possess?
Boundaries: At almost twice the age of many first-time founders and with a family to consider, can I find the right balance? Will my tendency to become obsessive about work hinder my ability to be a supportive partner, present father, and successful founder?
Mediocrity: People think most startups either fail quickly or achieve monumental success. But what about the vast middle ground – the "successful enough" scenario? Can I stay passionate if I find myself running a venture that's neither failing nor soaring, just perpetually adequate? Will I be able to maintain my drive if the magnitude of success falls short of my ambitious dreams?
Optionality: Will my passion for the business endure for five, ten or more years? What if, along the way, I find something else that captivates me? My entire career, I’ve had optionality and flexibility, but as a founder, I’ll have neither. Will I be comfortable with this shift?
Relationship dynamics: Beyond my family, how will being a founder affect my relationships with friends and industry peers? If I’m successful, will people be genuine? If I fail, will they distance themselves?

When discussing these fears with friends, a few asked why “fear of failure” wasn’t on the list. The truth is, I’ve never shied away from it. When immigrating to the United States, I didn’t even consider what would happen if I couldn’t adapt to American life. When I left Microsoft for Stripe, I had massive impostor syndrome, moving from a huge corporation to a 100-person startup. And when I joined Brex in an executive role, I thought I was more likely to get fired in my first year than to complete my equity grant. But none of these fears ever factored into my decision-making. Failure is one of the deepest ways we learn, and while I’d prefer to avoid major setbacks, I’m eager to learn from the smaller ones along the way.

I’ve always felt restless when my learning slowed down. This is, without a doubt, the biggest learning opportunity of my career. Despite the fears, my excitement for growth far outweighs them. As I embark on this adventure, I hope that when I look back on these words in a decade, I'll feel the same mix of anticipation and resolve. The path of a founder is uncertain, challenging, and often lonely, but it’s also a journey of unparalleled growth, impact, and fulfillment. Here’s to embracing the unknown, growing through the journey, and bulldozing through every fear.