Some Advice For People Joining A Tech Startup For The First Time
Joining a tech startup for the first time is extremely difficult. If you’ve come from a big public company or a non-profit or the public sector it can feel really unnatural and even uncomfortable. The way you’ve operated in the past likely won’t work. Things will feel weird.
I’ve had the luxury of working in five different tech startups and have been in a position to see trends around the things successful people do and the things the not so successful people do. Here's some advice based on what I've seen over the years. I hope it’s helpful for people that are joining a tech startup for the first time.
Be incredibly good at dealing with change. Depending on the number of employees in the startup, headcount can literally double in a month or even a couple of weeks. The number of customers serviced can double. Cash in the bank can grow by 1000x. A crucial employee can quit. A major customer can cancel. Because startups are small, change and its impact can feel radical. The company can become a different company in an instant. This is a strange thing. This doesn't happen in a normal company. In addition, in the early days, a startup is really just a hypothesis about solving a problem. And the way that the company is solving the problem will change constantly. For the employee, this means they are likely to have different bosses and jobs and roles and projects in a short amount of time. Learn to enjoy and thrive in this change.
In your first 90 days do something awesome. When you join a startup, because of its small size, you’re going to have a lot of eyes on you — particularly from people that can make decisions about your future. Find a way to impress them. Take ownership of a project or a sale or a product or a process improvement and dive in deep and make it great. Be transparent about what worked and what didn’t. You’ll find that failure is generally not frowned upon and learning is highly valued. Doing something awesome is not necessarily easy. It’s not going to come to you. Have zero expectation that someone is going to set you up for success. Go get it and make it happen.
Avoid playing politics. In larger companies, to get ahead you have to play the political game. This is much less true in startups. In a large successful company an employee can do nothing and play politics and the damage to the company is non-existent. The great employees aren’t playing this game and if you are you’ll stand out. People will pick up on it and you’ll get a reputation as someone that is political and it’ll be hard to shake. Get stuff done and be transparent about your success and learning. The downside of a startup is sometimes if one person doesn’t like you it can hold you back because there isn’t a defined system to move you forward. This is why you should avoid playing politics because it’s a quick way to get people that matter to not like you. The way to be liked is to produce results and share what you're learning.
Think short term and long term. This is one of the hardest things to do. It's not natural but it's necessary. The main thing that is going to get you ahead is your ability to produce short-term results and to be transparent about those results (and your learnings). You have to think short-term and show weekly if not daily progress. But you also want to have a longer-term point of view on your industry and where things are going. Your leadership team is getting paid to predict the future and that's hard to do. They will love the employee that can deliver short-term results but can also act as a thought partner in how the company should be thinking about longer-term strategy.
Make work a very big part of your life. There are times in our lives where we want to focus lots of attention on things outside of work. If you’re going through that time in your life then I’d encourage you not to join a startup. A startup’s cost of capital is generally extremely high. It costs the startup a lot of equity value to raise the capital needed to pay your salary. Because of that, there will be high expectations around your commitment and production. This is a crucial point. It’s simple math. It costs much more for a startup to employ you than it does a big company. And your impact is also greater. If you’re in a 30 person team your contribution, on average, is 1,000 times greater than the same person in a 30,000 person company. The startup is going to rely on you greatly. If you’re uncomfortable with that pressure you’re in the wrong company.
Be humble. It is enormously difficult to effectively operate in startup if you’re not humble. It almost can’t be done. The way you are doing things today is going to change dramatically because it’s not right. Your product isn’t right. Your pricing isn’t right. Your process isn’t right. Your go-to-market isn't right. You have to have a perpetual curiosity about what can be done better, the humility to recognize it can be done better and the willingness to go out and do it better. If you can’t check your ego and do this well you will fail.
Hire people that are better than you. When you’re hiring people there’s a temptation to make sure that you’re not hiring someone that can take your job. Do the opposite. Hire people that can take your job. This may not feel natural but I’ve found over and over again that people that are willing to take this approach win because they build A+ teams and that’s much better than the safety that comes from hiring a B team. A+ teams create exponential value. B teams create linear value and in some cases negative value.
Be insanely commercial. Most startups are not sustainable. If they weren’t taking in outside capital they’d go out of business. Be very aware of this reality. This is not a comfortable situation for the executive team. By definition it’s uncomfortable. Embrace this reality and get onboard with leadership in understanding that it all could come crumbling down. Commercial success is the only thing that matters in the early days.
Challenge yourself to understand context. Because things move so fast and there often isn’t clear ownership and process, decisions made by leadership or other teams may seem dumb. People may seem incompetent. This generally isn’t the case. At one startup I worked in I had the luxury of working closely with the leadership team but I wasn’t on the leadership team. I’d be in the room and see how leadership made decisions and then I’d be out for drinks with my peers and they’d complain about how leadership was clueless and didn't make good decisions. I couldn’t believe what I was hearing. The problem wasn’t that leadership was incompetent, the problem was that my peers lacked the context and lens that leadership was operating under. Challenge yourself to not dismiss seemingly bad decisions as people being uninformed and try to see the decision through the other person’s eyes.
Consider doing the impossible. If you dive into the history of most extremely successful startups they probably did something at some point that seemed impossible. This is true of most major success stories. For some reason, I always think about poker on television. Today, millions of people watch poker on television but there was a time when this was a crazy idea. The reason was that the great players would never agree to have the cameras see their cards during a game. And if the viewer couldn’t see the cards all the drama would be lost. But it was a non-starter with the players. No way. Never going to happen. But some ambitious TV producer saw the opportunity and didn’t accept that reality. He forced it and found a way to get the players to agree and now television poker is a multi-million dollar product. Consider the things that you think are non-starters or are impossible and try to see if you can find a way to break through. Don't be the naysayer. Be the one searching for the solution to the impossible problem. Find a way.