Earlier in my career I attempted to try as many of the employment options in tech as possible – being an employee in a startup, founding a startup, contracting/freelancing, and working in big tech. It was 2015-17 when I had a go at starting a startup with a friend. It didn’t take off, but I don’t regret trying – I scratched the itch and learned a lot.
Over the past year, through the period of tech layoffs, I’ve had more conversations with friends who are interested in startups than I’d had in the preceding 5 years. While I can’t necessarily say I know how to build a successful startup, I do know what I wouldn’t do the next time in the early stages. Given all my recent conversations, it seems like a good time to put them in writing.
Motivation
Building a startup requires a lot of motivation and energy. Aside from enjoying working with your co-founder/team (the most important thing), the product you’re building needs to keep you engaged.
The best way to validate startup ideas is often to build them as side projects first. The most obvious reason behind this, often spoken about, is that it allows you to see if anyone wants to use it before going too far. Just as important though is that it helps you see what you’re motivated by. If you’re spending a large amount of your spare time building something, and constantly feeling like you don’t have enough time, that’s a good sign. If you’re lucky to get one to a point it’s getting so much use you just don’t physically have enough time to keep up, that’s a good time to jump in full time.
If you’re struggling to get your side project built, it’s worth thinking about if you’d really want to be spending all of your time trying to build it – maybe it’s just not interesting or fun enough? From my side, I’ve never had much of a problem motivating myself to work, so I actually didn’t feel a massive difference here between startups and bigger companies. I did enjoy the freedom to try out new ideas or technology without having to worry about how others would see it though when in the startup world.
Aim for regular use
Especially for first-time founders, I think the best startup ideas are those which users will use regularly over a long period of time. Ideally they’re something you’ll use yourself regularly too.
When I was working on a startup we were building a better way of searching for apartments – you could filter by your commute time, see travel times to your favourite locations right on the listing without having to jump to maps, and book viewings directly through the site. Unfortunately, at least for rentals, these kinds of services have very high retention for short bursts of time, and then people move apartments and you don’t see them again for a year or more. As a founder, you’re also not moving apartments regularly. This makes it hard to see if you’re improving things for particular users over time.
If you have a product where people come back once a month over a very long period of time, that’s something you can work with. You could run A/B tests for improvements and see if you could make the product useful enough they want to use it every week instead, and then maybe every few days. If the product has a natural ending, this is very hard.
Another trap I fell into here was trying to build a marketplace. Property websites need both the apartments (landlords), and the tenants. Marketplaces are sticky when they work, but can be hard to get off the ground – usually you need to build up the supply side before there is any demand, which can be a tough sell. For a first-time founder this can be particularly difficult.
The startup idea often isn’t the most important thing – things like the team and timings play a big role. Some ideas can definitely make your life much more difficult though, especially as a first-time founder.
Tech choices
Tech choices rarely change whether a startup is successful, but I think it’s worth picking languages or frameworks you know well, you are fast at building with, and you know will be stable.
The startups who succeed are often the ones who build new features the fastest. If your tech stack allows you to do this, either by design or just because you know it well, that’s a big advantage – even if it’s not the latest-and-greatest. Some of the biggest websites were built with PHP, after all. You want to be improving what users see and use, and not fighting with something being unstable behind the scenes. Boring is probably good in that sense.
I used Node.js, React, and AWS when building our website. These are battle-tested technologies, so we had no problems there. I also enjoyed the freedom to be able to learn new things like this. In big tech we tend to stay more specialised, for better or for worse, as I have done with iOS.
An exception to this rule is if the technology is the startup itself, but that’s the less common case.
Being in control
This one is less a lesson, and more an observation. Being in control of your own destiny is one of the biggest pulls of being a founder. There are tradeoffs with all different kinds of jobs though. It’s not as clear cut as it first may seem.
As an employee you’re likely to have much more control over your time than as a founder. If you’re a founder and something goes wrong, technical or otherwise, you’re probably going to have to fix it whatever the time. As an employee in a larger company that’s less likely to be the case. In effect, you’re always oncall as a founder.
As an employee you have one manager, and maybe some reports. As a founder you are more likely answerable to a board, investors, and all of the employees under you questioning your decisions. That’s ignoring your users too! In many ways that’s even more people to please. On the other hand, you can make decisions that you wouldn’t be able to make as an employee.
Financially there are obvious tradeoffs too. As an employee you can depend on a salary. As a founder you might feel less control here – you’ll be the one forgoing pay when times get tough. The reward can be much higher if your startup is a success though.
Often I see these tradeoffs as similar to owning vs renting a house. If something goes wrong in your house, whether you own or rent, you still have to live with the problem before it’s fixed, arrange for somebody to come and fix it, and be in when they come. If you own you have to pay, but you also get the choice of who fixes it. If you rent, somebody else will decide how it’s fixed, but you don’t have to pay. There’s no right or wrong here. Which is best is different for everyone. For me both are good in different ways – I sometimes get tired of one and probably need to switch to the other to keep it interesting (until something sticks!)
In summary
Being a startup founder is hard, and definitely isn’t for everyone. You do learn a lot though, and you won’t necessarily know if it’s for you until you try. That is unless you’re somebody who really can’t work for somebody else! In either case, I found it worthwhile trying. Start with side projects, and see where that takes you.