Startup Life: On Big Bets and Hard Things
Nov 6, 2023
Admittedly, the challenges have outweighed my accomplishments in my stint in startups so far. I’ve second guessed my potential to thrive in this ecosystem, where challenges can be unforgiving when not dealt with appropriately, and the downs can be discouraging. When the decline of startups and tech layoffs have been making headlines the past months, it’s hard not to question whether the startup life as a career path is the “right” move.
Distraction compounds on this self-doubt as you let comparison be the thief of joy.
Having recently digested Status Games by Will Storr, I’ve recently learned that humans play “games”. Some more than others. As with all games, there are rules for its participants and for me, this “game” that I am participating in follows the parameters of the startup world.
What do I seek to achieve from playing this startup game?
Quite frankly, alignment with my following values:
Ownership with my work
Being part of creating something meaningful, even better if its a new category/market where I get to a part of pioneering it
Having pride in what I am building
Working alongside long-term people in a long-term game
Prioritising compounded growth over instant gratification
In the midst of this all, startup life is hard. For me, it’s because of these three reasons:
Dealing with the infrequent imposter syndrome
Understanding how to be comfortable that there is no right answer
Detaching your ego away from the company’s growth
I’d say that alot of this have no silver bullet or playbook, but rather time that will help me overcome these hurdles. Time (and experience) when compounded will help me foster the right qualities and perspective necessary to navigate through the challenges.
At 24, I know I’m still young but when I’m surrounded by so many successful and accomplished individuals who have done so much in their own right, I forget that.
This is particularly harder when working at a pre-Series A company where things aren’t as cemented as they can be, leaving alot of uncertainty about how your role will evolve and how the company will overall grow.
Bottom line is that startup life is hard.
But as the founder of Ecko famously said, “Companies aren’t found, they are built.”
This comes with some new major learnings for myself to navigate in the hard parts of startup life that have added to the reminders I have taken from Paul Graham.
Anyone who knows a thing or two about startups would know that the name Paul Graham is synonymous to this ecosystem. If you know this, you’ll also know that one of his many famous essays reflects on what startups are really like. And while much of this essay speaks mainly to founders, there’s five principles out of the 19 principles that have resonated very well with me as a startup operator over the past few years working at Loopit.
It's an Emotional Roller-coaster
It Can Be Fun
Persistence Is the Key
Think Long-Term
Lots of Little Things
These five principles as a culmination have acted as a friendly reminder, almost a north star as to the game of startups.
As a response to these principles by Paul Graham, I’ve come up with three “mantras” that have helped me stay the path and be more convicted in this startup journey.
1. Taking Big Bets
As I’m getting older, I’m realising how life really is too short to play it safe. And while I admire the risk that entrepreneurs and freelancers alike take; I don’t think I have the capacity (at least not yet) to do the same. On the other spectrum, I don’t think I could play it safe and not be challenged.
However, what does suit my appetite is taking big bets with the belief that if the bet lands, the winning feeling is unmatched. I dare compare this with the thrill of having your multi hit on a sports bet.
Startups (the ones that have high TAMs and growth potential) are a great way to harness those bets. The stake of the bet is almost parallel to the stage of the startup too — the earlier the startup, the larger the winning potential.
Uncertainty at startups can suck but in a way it does force you to ensure that you do whatever you can control to ensure you and the startup is in the best position for success. That’s where the creativity best kicks in. In moments where there’s no answers. In moments where experimentation needs to be embraced. In moments where pushing the envelope may be the only way to exercise your control in times of uncertainty.
And even if that wild project stank, at least you tried and learned something valuable. I think thats the upside with startup. Regardless if bets fall through, its not a zero-sum game in the sense that you’ll still win regardless with the learnings.
2. Thinking Big Picture
Working in a startup allows you to work on a skill that is devoid in todays generation. The ability to think long-term and forego instant gratification. Too often, I hear fellow peers advise on the need to jump between roles as a way to maximise earning potential; and while I’m not saying that’s the wrong way of going about career growth; it’s definitely not for me.
My contrarian view is that putting your eggs into one basket and seeing those eggs compound is all the more rewarding.
Even when learnings come slow, it is still very rewarding when you realise that those have come over an extended period of time. Of course quick wins feel great, but the realisation in retrospective that you as an operator and the startup itself have grown (and persevered) through the tough times is unmatched.
3. Startup = Hard AF = Grow Faster
No doubt the uncertainty and pitfalls that come with being a startup operator can be disheartening. For me, it’s caused me to question my career progression and doubt the ceiling for my financial earnings. However, there is upside to putting ourselves in tough situations.
This sounds a bit self inflicting, after all we would want to live an easy life right?
Allan Watts speaks that life without any obstacles can deprive meaning from life. For example, if we effortlessly get every job we wanted or if a boxer wins every fight; then would the reward be as fruitful compared to the journey that had obstacles?
Paul Bloom speaks about the power of “chosen suffering” - where putting ourselves in hard-fought situations gives our pursuits meaning. Difficulties and challenges gives value.
I’ve also been told to always view years at a startup in terms of “dog years”; where the skills and experiences you learn in one year is equivalent to 3-4 years elsewhere. Often we are told that time is the biggest opportunity cost for career progression; so it only makes to me at least to try accelerate that. Learn as many skills, wear many hats, gain many operational perspectives from different departments — in as little time as possible. I was told to think of it as a slingshot, where the longer (and harder) you pull, the further and higher you will fly in the long-run.
4. Building Perennial Things
The underlying mantra of (most) startups is to be the first to a new market. To forge a new movement. We don’t have to look no further than the likes of Uber, Figma and Canva, just to name a few.
In essence, be a part of companies that have built not only a product, but an (sub) industry that stands the test of me.
There’s joy and pride in being able to say that you were part of the early stage. Maybe it’s an ego-exercise, but there is a prouder sense of accomplishment when you say you helped build something from the ground up.
For me, I personally value being a part of the early discovery stage in all aspects of life.
As a closing note, I think startups are a great way to pursue interesting things and creating value. It is from this that we are able to navigate what exactly we want to work on and what projects we want to commit ourselves to. Sam Altman synthesises this best in his interview on Y Combinator, where he states:
“The fundamental pattern that has always worked for me is take time, explore a lot of things, try a lot of things, try to have a beginner’s mind about what will work and what won’t work. But trust your intuitions, pursue a lot of things as cheaply and quickly as possible. Then be very honest with yourself about what’s working well and what’s not. And then the hard part is cut out all the stuff that’s not working, and focus down and down until you’re eventually focused on the one thing that’s really working.”
Coming from a more philosophical perspective, solving the best problems are the ones that attracts and confronts us. It demands a response from us that we should choose not to deny.
Friedrich Nietzsche claims that self-defence is one of the worst ways to spend your energy.
Instead, tackle these problems head on because it is only then we can unravel who we truly are and what we truly want in life.
