Default Optimism
All Things Venture #076
I think one of the things I enjoy most about working in early stage startups/tech,/VC is that there is this overwhelming belief in the possible. Building a successful venture backed startup is an absolutely daunting task. It’s Sisyphean in nature where your reward for doing fantastic work is ultimately just more work. The vast majority of variables are outside of your control, and (depending on the category) you will have competitors who are quite literally trying to eat your lunch. That being said, in no other professional environment (outside of sports) have I encountered more enthusiasm, passion, or belief in the possible.
It’s infectious.
The default mode for most people I meet in this environment, whether they are investors, engineers, marketers, PMs, AEs - whomever, is to be optimistic. The default mode is to believe change is not just possible, but necessary. Samantha John, the founder of Hopscotch, shared that exact sentiment when retelling how she knew she wanted to be a founder. Here’s what she said:
“Honestly, I am not a very good employee, and I think an aspect of my personality is that when I see something that I think is not quite right, I feel very compelled to fix it. It’s both good and bad and it extends to everything…. The amazing thing about being a founder is yeah, you get to make all the mistakes yourself, but YOU ultimately get to decide what to do. YOU are the one who makes sure the company is functioning well, that the meetings are efficient, that the design is top notch. You know that the mission is clear, and that if any of those things are not happening, it's because YOU are not doing it.”
Said another way and in not so many words, at startups, whether you’re the founder or the first on board - you get to be the agent of change.
The people who join startups want to build, they want to kill inefficient meetings, they want to take a shot at success, and I do too. I absolutely love it, and it feels like such a stark contrast to the professional environments I was previously exposed to (i.e consulting - BOOOO and banking - BOOOOOOOOO). I chafed at the structure, the process, the bureaucracy of those environments, and I think a lot of people find them to be mind-numbing, transactional, and soul crushing. Or as Matt Taibbi so eloquently put, in reference to Goldman Sachs’s responsibility and involvement in the Great Recession they are, “great vampire squid(s) wrapped around the face of humanity, relentlessly jamming [their] blood funnel(s) into anything that smells like money.”
Frankly, I would prefer not to work at a place that is referenced in popular culture as a vampire squid and I’m not saying that venture capital is a spring chicken either. BUT, if we all have opted in to participating in our capitalist system, I would personally prefer to be paid to be creatively constructive versus selectively extractive.
I fully understand that work will always be WORK, and nothing worth really doing in life will ever be easy. But I also believe that my work doesn’t need to be a mind-numbing, repetitive, clock in-clock out, hopefully see you never type of environment inside the belly of a massive, colloquial vampire squid.
Why?
Because, there was a point in time in my life where I got smacked in the face with a mid-20s realization I’m sure everyone has: If I get an average of 8 hours of sleep a night, and the average workday in the long run is 8 hours, then 50% of my waking life, my conscious life, at a minimum, will be spent at work until I’m 60-65. I realized I would spend more time at work, than with my family, with my friends, and with my future children, and when I had that moment (and panicked a wee bit). I realized I had to do something that I innately CARED about, that aligned with my view of the world, that aligned with my default optimism, and sense that there’s always a way for things to change. And for me, that escape hatch was entrepreneurship.
I think what I’m trying to communicate and part of what I think my path in venture will be is just to help more people become comfortable with the inherent risk involved with joining an early stage startup and realizing how rewarding (and actually not risky) it can be. I want people to realize that the belief in the possible, in the arena of the startup world, is awarded in spades. I want people to realize that working at a startup, while inherently chaotic, unstructured, and ambiguous, is simultaneously invigorating, collegial, and fulfilling. Things will break. You will fix them. Things will change. You will adapt. In every part of the entrepreneurial process that I have been exposed to over the last 3 years, from paper napkin businesses to billion dollar unicorns - the unifying themes that I observe in people are a desire to work hard and be commensurately rewarded, to be a part of something bigger than themselves, and to leave a meaningful impact in some way, shape, or form. Startup people want to use their most valuable asset, combine it with a sense of default optimism, find their little band of pirates, and take a shot at changing the world.
That, to me, is the heart of entrepreneurship. It’s the heart of the startup ecosystem. It’s the heart of venture capital. I think that the predominant narrative of entrepreneurship is:
Have a crazy idea, stare deep into the abyss, jump head first, build the plane while you’re flying, become Facebook, make billions OR, die
In reality what I think entrepreneurship is, is a little more like this:
Have a crazy idea, stare deep into the abyss, jump head first, build the plane while you’re flying, fail, pull your parachute, land in front of another crazy idea, stare deep into THAT abyss, build THAT plane while flying, fail. Pull a NICER parachute, rinse and repeat until you realize it was never about making billions or making Facebook; it was about enjoying building and working with smart, talented, motivated people who want to change the world.
The inherent failure associated with startups by no means diminishes the initial intent or desire, nor should the prospect of failure scare people away. Parachutes and soft landings are built into the ecosystem, and there will always be opportunities for builders to build.
As I always talk about with All Things Venture, I want this newsletter, and this little community we’ve built to be a genuine source of insight, education, and a platform for people doing the work, day in and day out, staring into the abyss and jumping any way. My hope is that our generation will make the startup ecosystem more dynamic, more exciting, and more accessible to more people. At the end of the day, who gives a shit if we have parachutes or not? It’s still going to be one hell of a ride.