30 was always a big number. I don’t remember why. For some reason, it always haunted me—and not for the reason you’re thinking.
Yes, in 2022, I turned 30. But 30 was more synonymous with fear than age. At least to me. Expanding Stears beyond 30 people made me anxious. Whenever we came close to adding the 31st employee, I would stall, hesitate or second-guess. I had many excuses. Budget. Too few managers. A good hunch. A bad hunch. Instinct.
For a long time, we hovered between 25 and 30 people. Until 2022. In 2022, we crossed this milestone, and we crossed it boldly. There are now nearly 40 people (and growing) at Stears, and I have never felt more optimistic about building than I do today.
Building, in Silicon Valley culture, is no small feat. They say it gets easier with time. Not because the problems get smaller or less scary. But because the entrepreneurs get better.
You can’t be a successful entrepreneur without being an optimist—or at least that’s my view. You cannot be too careful. Or too cautious. Or cynical. Sceptical, of course. But fundamentally, optimism must be the addiction. You have to believe that what didn’t exist should exist and that you should be the one to build it. Then, you must combine this with the grit, perseverance, and luck that come with flawless execution.
For first-time entrepreneurs like me, this is hard work. That we made it this far is a win. And that there is optimism about the future is a double win.
I reflect on my wins by writing about them. I write a lot because I read a lot. And I read a lot because it's how I learn. So, I hope those who read this learn as I do.
Now, let’s jump into 3 key lessons from building Stears in 2022.
#1 Founder energy matters
The most powerful lesson I learnt this year was unexpected but crucial.
Fundraising, as most people understand it, is a commercial exercise. A capital raising project. A CEO’s job. But that view is too small, too limiting and too practical for this annual reflection. Yes, It is part of the CEO's job, and like any other, it has its commercial goals. But it can also be a transformational exercise if we let it.
Early this year, the fundraising market for technology-driven startups changed. Things were different. YC told founders to plan for the worst. David Sacks publicly spoke about ‘operating in a downturn’. Crypto was rattled to its core. And the US Federal Reserve sent markets spinning. I expected my biggest 2022 lesson would be how to raise funding in a downturn. Instead, this year, I re-learned what it meant to be founder-led.
A lot has been written about the importance of founders in startups. For me, it boils down to one word; energy. Founder energy is, quite literally, unmatched. It’s the 3 am calls. The Sunday morning meetings. The never-ending rants. And the constant worries.
It can be tough to harness, but when founder energy is refined, channelled and transferred, it is a driving force. It is a startup’s oxygen.
I thought I already knew this. I guess I had forgotten. But, right on cue, I found myself drawing closer and closer to my co-founders as we navigated the fundraising markets. I realised we were building new, deeper, founder connections.
Most BHAGs (Big Hairy Audacious Goals) will usually do that, but this time it felt different. I’ve known my co-founders for years. I met one when I was 10 years old and the other two at age 19. It’s been a while. And yet, the shared experience, unevenly distributed, of having our vision challenged, questioned, broken apart and put back together brought us closer together in entirely new ways.
What makes a good founding team? Most investors can reel out the traits they value. Brilliance. Grit. Hustle. Luck. It's an endless list which I know little about. What I do know is that survival matters most when you are on the ropes, in the struggle. And when the struggle comes, what you will want, what you will need, what might save you, is a team that is there for you. The way my co-founders were in 2022.
It’s a lesson I will not soon forget.
#2 Cultures need to evolve
Culture is a strange beast.
In some ways, it is a simple set of values like People, Action, and Quality (the Stears values). But in other ways, it is not a thing to be talked about but rather to be seen and lived. It is actions and decisions compounding. It is what people do when they are not thinking. It is what they instinctively live by.
It is also incredibly hard to change.
I was academically and professionally trained as a lawyer. So, as an entrepreneur, I have a bias for depth. It's part of who I am, and I accept it. I love depth because it reflects something innate to me: a deep addiction to raising the standard, setting apart, and being better than the last. In my world, nothing should satisfy short of the best, even if the best is purely aspirational.
It's also why Stears operates the way it does. With a bias for digging deep. It’s why the average article is 10 minutes, and we prefer to focus on quality, not quantity. At Stears, depth has been more than just a buzzword. It is necessary for survival. The very essence of our competitive advantage.
But, in 2022, it started to feel like a burden. And I had to confront this bias for the company to move forward.
The problem with depth and rigour is that despite its merits, it costs time. More often than not, the extra conversation about the merits of a new feature, the cultural fit of a new candidate or the methodology behind an index slows down decision-making and momentum.
So, this year, I observed the trade-off. I learnt that the perfect can be the enemy of the good. And I learnt that sometimes, you need the people around you to challenge even the most hallowed cultural values.
The most powerful part of this lesson is that it reminded me that values, like companies, need to evolve. The cultural values that drove the first three years of Stears need to be revised for a newer, more ambitious future. We need to evolve how we think as an organisation and the operating models that put our goals into practice. Despite only being around for a short period, it’s already time for a change.
Next year, I expect this lesson to play a bigger role in how we build. More experiments. Less perfection. But still getting the work done better than the competition.
#3 The team that did it at 25 won't do it at 100
As I said above, as an organisation grows, it evolves. New capabilities are made possible. New ways of doing things appear. Some traits also disappear. Just like people.
So, the final lesson I learned this year was acknowledging that because the company is a living, breathing organism, it's not just the values that need change. Its needs, wants and expectations also need to change. What we needed in 2020 is far from what we need now.
For instance, most people know me as an OKR (Objectives & Key Results) champion. It was, and remains, a fantastic goal-setting tool. But, it's not perfect. It’s incomplete. And this year, I watched as a larger, more diverse team needed a revised OKR template to achieve the company goals. It took some experimentation and a few false starts, but eventually, I learned that we needed to combine our goal-setting tools, like OKRs, with newer tools that speak to a more long-term growth plan (for context, OKRs are set quarterly). This is just the beginning, but it's exciting to revisit old truths. The experience here crystallised a profound truth: the people, habits and operational models that help you start may not take you where you need to go.
How did I start to acknowledge the need for this evolution? A pretty common magnifier; mentorship.
Most people understand what mentorship is about—a wiser, more experienced teacher or expert guides a younger, inexperienced, but willing student. It comes in many shapes and sizes, from casual to professional. And it often starts in the most unexpected ways; a coffee meet-up or long chat at a conference.
But at the risk of exaggeration, I will add that mentorship is transformational.
As CEO, I am usually the one giving advice or recommendations. So at first, the role reversal was jarring. But it became refreshing very quickly. And now, it’s a seminal part of my journey. Building can sometimes feel lonely, especially in top leadership positions. Senior leaders are, by necessity, sometimes restricted in whom they can talk to and what they can say. So, having mentors, especially from outside the business, who can help you talk through and tackle tricky business problems is golden.
For me, mentorship changed everything. It made a massive difference to have someone else, not obligated by professional duty, give me an expansive view of where I was coming from and where I am headed. Mentorship is all about getting help to see and find the right path. I believe I found the early stages of that path in 2022, thanks to two amazing mentors, Dave & Fola.
A special shoutout
In the last two reflections, 2020 and 2021, I have emphasised the importance of people. This year was no different. No group of founders, executives or senior managers can do anything alone. Building is a team sport. Teams require people. What we have built and will build is only possible with a fantastic team of people. And it takes work to run a larger team.
Like a racing boat’s crew, we need to pull well together, in sync, each (wo)man doing her best, and with a common goal at the end of the line. We need not, of course, agree on everything, but we must align because alignment is important for winning.
This superstar team changed my world again this year. And I don’t expect it to be different next year. So, as we end this year’s annual reflection, there are no better words to end this than to say: Thank You to all the amazing people who make Stears what it is today.
A section of the Stears team
The bigger picture will matter in 2023.
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