I left Shopify in June last year. My team had just launched the new Point of Sale, rewritten from scratch using React Native. It was a multi-year undertaking and a big deal for the company. Many folks doubted whether React Native was the right technical choice for an app that had so many custom hardware dependencies. I have to admit that it felt amazing to prove the naysayers wrong by shipping an app at the level of polish and performance that Shopify is known for. But as I reflected on this accomplishment in the days after we launched, I couldn’t help but feel restless to get started on the next thing. By this point it was already clear to me that the next thing was to start my own company.
Why did I leave?
When I tell people that I left Shopify, I’m usually met with some well-meaning remarks.
I get it. The stock’s been tanking hard, so time to jump ship, right?
Is it because you had to go fully remote? Shopify was known for their offices. Don’t they get that teams actually prefer working in person?
I thought you liked it there. What happened?
The assumption is that I left because there was something wrong with Shopify or its culture. I’ve been in the industry long enough to know that there’s no such thing as a perfect company. Shopify is no exception. That said, it is without question the best place I’ve ever worked. Companies like Shopify are exceedingly rare. They offer product builders a wealth of challenging problems and ample autonomy to tackle them. There was never a time when I felt disengaged by the work I was doing there. It all felt meaningful.
But something was missing. I wanted to learn more, build more, own more. I’ve never been the kind of person who gives themselves completely to a big company. I can’t help but hold something back. Before Shopify, I started an app development agency called Secret Mission Software. We eventually grew to ten people as we took on bigger and bigger clients, including Shopify (sidenote: they eventually acquired us for our mobile and React Native expertise). Starting a company was like having a baby. I wanted it to grow up healthy and be successful. When I was running my own company, I gave it everything I had. You know what I’m talking about: that all-in energy. The stuff we reserve for the things most important to us.
I missed not holding back. Here I was, doing some of the most important work of my career, all the while feeling like I could be doing so much more. What does one do with that extra fuel? At times I worried that I’d lost the desire to start another company; the pandemic aged me considerably. But I knew, deep down, it was something I had to do.
Why now?
You might have noticed that we’re in the middle of the worst economic time in recent history. I wouldn’t blame anyone for asking the question: why would you start a company right now? It’s not for the faint of heart. What they don’t tell you is there are some advantages to starting a business during a downturn. Think about it: the job market has cooled off significantly over the past few quarters. Layoffs continue at large tech companies, creating a deeper talent pool for startups to hire from. They no longer have to compete for talent with the tech behemoths because the latter are growing much more cautiously. While the industry as a whole grew at an insane rate over the last decade, stock-based compensation in these large firms is looking far less attractive today. If you’re at a big tech company, gone are the glory days of hypergrowth. But not for startups!
Startups, by definition, have a much greater potential for growth ahead of them. The less-than-ideal market conditions level the playing field. If they can stay lean and make it across these choppy waters, they’ll experience significantly more upside than any of the large tech companies can during the next bull market. That’s a big “if” though! I don’t mean to minimize the challenges startups face, especially when VCs are increasingly mindful about where to allocate their funds. But for the entrepreneur, there’s a bigger opportunity available now even as the economic outlook looks uncertain.
Without a doubt the most challenging part of leaving a well-paying, full-time job has been the impact on my personal income. We’re bootstrapping the initial version of our product, which means that for the first year, at least, I’m taking a 75% pay cut. For most people this reality is too sobering to bear.
“The three most harmful addictions are heroin, carbohydrates, and a monthly salary.” — Nassim Nicholas Taleb
Nobody wants to change their spending habits. And on top of that, hedonic adaptation ensures that our desires and needs increase imperceptibly as we earn more. It takes a concerted effort to tighten the belt and live within your budget from a decade ago.
One way to look at this pay cut is to treat it as an investment in my own ability to create value. Thinking about it this way is surprisingly motivating and makes the sacrifices easier to accept.
The Allure of Entrepreneurship
When markets are booming and valuations are through the roof, it’s easy to make the case for pursuing a startup. This is especially true if you’re interested in generating wealth. But you can easily fool yourself into believing that it’s all rainbows and unicorns at the end of the startup journey. Don’t get me wrong, I’m all about that upside! But the road is a challenging one. The first couple of years at a startup are often lonely and full of self-doubt. If you struggle with imposter syndrome as an individual contributor, imagine the pressure of setting the vision for an entire company year after year. When faced with these difficult conditions, the entrepreneur experiences a shift in their thinking. They realize that there’s much more to starting a business than the money.
Entrepreneurship is a lot like a turn-based strategy game. One of my favorites growing up was Sid Meier’s Civilization. In Civ and its many sequels, your goal is to build the strongest and most resilient civilization. The game world is shrouded in a fog of war, and the player must explore, learn and adapt quickly to survive. You start with very little: just a small band of nomads, searching for a place to settle down and start building your culture. From these humble beginnings, you must decide how to allocate your finite resources. Will you focus on research, or building an army, or maybe set to work on a world wonder? There are many so-called victory conditions in the game, but ultimately, the player’s objective is to create a more efficient engine of research, production and expansion than the competition. Just like in the game, these three factors stand out as being key to a winning strategy in building a business:
- The ability of the founders to learn fast and iterate
- The productivity of the team and their ability to ship often
- The amount of leverage that they can apply over time
What’s obvious to anyone who grew up playing these games is that great decisions at the very beginning have a compounding effect over time. In the early days of a company, you have very little leverage. Most of it has to be built from the ground up. But being ruthlessly focused on generating momentum is how great civilizations and companies are built. The reason startups can move so quickly is because they’re not bogged down by the bureaucracy and decision-making paralysis that plague many larger companies. They can use this to their advantage and apply these principles to create a winning strategy.
You might be wondering, “Well couldn’t I just apply these within an established company? Couldn’t I have a similar impact there?” Yes, of course! Applying these ideas within your team at a big company can have a massive impact. But there are limits. You might be dependent on an adjacent team that doesn’t operate as efficiently. As companies grow, the impact of the founders gradually dissipates as the responsibility of maintaining a culture of shipping and learning spreads out across the organization. Continuous upkeep is required to keep the engine of growth strong. From my experience, starting a company effectively removes any constraints in applying these principles. In fact, the innovation that we sometimes see come out of large companies very often germinates within small independent teams that operate just like a startup.
One last reason that I find entrepreneurship so appealing is that it serves as an incredibly efficient tool for personal development, especially if the founders are supported by mentors who are not afraid to give them candid feedback. It’s empowering to realize that changes in your own behavior or thinking can have an outsized impact on your business. Change is no longer something your mind tries to avoid in order to protect your self-esteem. You begin to welcome it, perhaps even crave it, once you witness the effect it has on the culture you’re creating.
What’s next?
The past year has not been quiet! After taking some time off last summer, I started collaborating with Robleh Jama on ways to improve how we do work online. After some initial prototyping, we settled on Boom, a virtual camera to help bring the energy to remote meetings. You can check out our website and read the manifesto at getboom.app. We’re getting closer to a public launch, so stay tuned!
The shift to remote work was challenging for me on so many levels. I found it much harder to make friends at work and connect with my team. Impromptu coffee meetups became a rare occurrence. Even the most casual chat needed a calendar invite and a week’s notice. Why all the formality? It felt like the fun had been sucked out of work. I don’t think it has to be this way. There’s a universe out there where remote meetings are actually fun, energizing and allow you to get more done.
Often our most challenging experiences lead to our greatest insights. I left Shopify with the belief that working remotely can be the default and that it doesn’t have to be a subpar version of working from an office. I’m excited to continue playing my infinite game of learning, building and growing while exploring new ways of making remote work truly great.
If you’d like to hear more about the product and company we’re building, please follow me on Twitter / X @mrkrishsatya.