One of the more rewarding aspects of my job is moderating the bi-weekly “Ask Me Anything” sessions with new StackAdapters. And one of the questions that comes up frequently in those sessions is whether I expected the company to get this big when we first started. I admit I didn’t, but not for the lack of ambition. We’ve always been ambitious, but in those early days when we were just trying to survive, it was difficult to daydream nine years into the future and imagine what the company could become. I certainly hoped it would become big, but the truth is I was more preoccupied with execution in the short term or in other words, survival. That being said, I did have some ideas about what becoming a big company would involve, and there are many ways in which I underestimated what it would take to get where we are today. Let me share some of them with you.
But before I do, I must say that underestimation of difficulty is often a natural side effect of being an optimist. And to start a company, you need to be an optimist because entrepreneurship is essentially an attempt to beat the odds.
Ok, let’s go.
The Bad
The following are things that turned out to be much harder than I imagined, or that I should have paid more attention to.
1. I underestimated how long it would take to get where we are now. Despite the fact that our company has consistently ranked on various “fastest growing companies” lists over the years, in my head I thought it was possible for us to grow even faster. I must have been either a bigger optimist than I realized or simply naive and inexperienced – likely a bit of both.
Growing a company is a marathon. Jason Lemkin from SaaStr talks about needing a commitment of at least 7-10 years from the time you start a company to see it properly through. I have to agree with him. Starting a company at the age of 25, it was impossible to imagine I would stick with one task for more years than I had been an adult – 9 years may as well have been 90 years at that age.
Whether you are a founder or a budding executive, the proverbial 10,000 hours are real – it takes many years to develop excellence at anything.
2. I wildly underestimated the number of people it takes to truly capitalize on an opportunity. Have a look at Salesforce, a company I think is doing really well. They have drawn upon the skills of 72,000+ people as of September 2022, and that number is still growing! Wow. To build a big business, you need a lot of people.
3. I underestimated how hard it would be to crack some segments of the market. For example, having started in Toronto, Canada, I was sure the Canadian market would be massive for us. But that was never the case, pretty much from day one. Our activity there is not insignificant, but it’s nowhere near where I thought it would be given that we started in Canada.
When it comes to opening new markets – whether it’s industry segments, geographies, or types of customers – it’s best to just go after the low-hanging fruit and double down on things that work. Sometimes you just need to tell yourself “this is an important segment, but we’ll put it on the back burner and revisit it in a few years”. Your product will never satisfy everyone’s requirements, and that’s O.K. Just focus on a large enough market where you have a good product-market fit – especially in the earlier days.
4. I underestimated how much things slow down as the company gets larger. Quick decisions were favoured in the beginning, but now they can do more harm than good. “Change management”, a term I laughed at in the early days, is a serious consideration that I now try (not always successfully) to not take lightly. Changing a small versus a large company is like turning a motor boat versus a navy ship. In a small company, you can pivot quickly and make a quick start. Try to turn a large ship quickly like that, and you very well may capsize.
But to go far and to weather turbulent seas, you need to be building a large vessel, and that means investing in the long-term, and building for sustainability – activities that inherently come at the cost of speed. But as your company becomes larger, so do its horizons. When we were a small company I was thinking one month ahead. Now I think in terms of a 10-year horizon. At that scale, it’s more important to choose the right direction than to try to save a few months.
The Good
These are the surprising tailwinds that made the journey easier than I had expected.
1. I underestimated how large the economy is. It’s hard to wrap your head around what hundreds of billions of dollars are since these aren’t numbers we deal with on a daily basis. The immensity of the market means that it can support a lot of business and there can be many successful companies in the same market.
2. I underestimated what can be done without PR or hype around your company. You don’t need to be in the spotlight to be successful; in fact, that kind of attention can often create more distractions than it’s worth.
When we raised our seed financing, we came very close to getting coverage on a coveted tech website. In the last hour, the journalist made the decision not to proceed with the story because he didn’t understand (or we weren’t able to communicate) what distinguished us from another company in the space that they covered regularly. I was devastated and felt like we had failed. The next day, I looked at our company and recognized that the most important things were still with us: new funding, our team, and our drive. So we just kept building. And I haven’t thought of that failed PR attempt again until now.
3. When you start a company, you naturally look up to other businesses, tech news, and business leaders for inspiration. As you grow larger, it’s easier to derive inspiration from within – from your own experience, customers, and team – and to create something unique. I always wondered how companies grow to become distinct in their product, their brand, and their culture. I understand now that this happens through a never-ending process of self-reflection and improvement. In the early days of running the company, I underestimated the importance of looking inwards, doubling down on our strengths, and focusing on what made our company unique.
4. I underestimated how many bright people from all walks of life I would have the honor of working alongside and learning from. I underestimated how many new and surprising doors open up when you reach scale. And I underestimated how much I could continue developing and growing – and how much fun I would be having – once the company has grown up.
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When growing a company, much like with other activities in life, you will never have a perfect window into the future. There will be miscalculations and setbacks. But the good news is that there will also be lots of positive surprises along the way. Many memories will be created – guaranteed.
Good luck!
Footnotes:
Image of the post is generated using Open AI's DALL·E