Lack of management experience leads to a variety of predictable people issues and operational mistakes, but they’re rarely fatal.
So I’d separate those operational mistakes (running slowly) from strategic mistakes (running in the wrong direction) which are a more serious blind spot.
Young founders are often good at building an initial product and talking to early users but don’t know what they don’t know. As a result, they often have trouble seeing the bigger chessboard. This was certainly true for me (I was 24 when we founded Dropbox).
There’s more to building a successful company and getting to scale than building a good product — you also need to make good decisions around markets, distribution, business models, strategy and dealing with competition, how to build and run a team, and so on.
The good news is if you’re systematic about training yourself, you can learn most of these things on the job. Even hyper-growth companies aren’t created overnight — curiosity and moving up the learning curve quickly are more important than avoiding mistakes. One of the most helpful questions for me has been “one year from now — or two years, or five — what will I wish I had been learning today?”
####### Someone once told me that life as a technical CEO is a journey from coder to psychiatrist. What made you good in one phase often becomes a liability in the next, and your job changes entirely every 6 to 12 months.
It’s exhilarating — I personally love the variety of challenges and can’t think of a job that forces you to grow as quickly. But it’s also uncomfortable: you’re repeatedly thrown into new roles you’re totally unqualified for just as you’re starting to get the hang of the last one.
In particular, what makes scaling hard is that every day you have to be as good or better at everything you were doing yesterday while constantly adding new things to your plate.
You want to hire people to help build the product, but to do that you need money. You raise a round of financing, but then you need lawyers and accountants. You build a product, but then you need to attract users. You get users, but then you need to support them and grow a sustainable business, and so on.
When things start to take off, that hyper-growth feels like harpooning a whale. “The good news is you’ve harpooned a whale; the bad news is you’ve harpooned a whale.” It takes all your effort just to stay above water.
You end up hiring a lot of people but then recruiting and keeping everyone on the same page turns out to be a lot of work. Hiring itself presents a catch-22: how do you hire a great marketing leader if you have no marketing experience? Meanwhile, the list of things that are broken never gets shorter and you feel like you’re always firefighting. Ultimately you realize that this is a good thing — if nothing is broken you’re probably not moving fast enough — but you get tired of hearing the phrase “good problem to have”.
How do you keep up? The answer is you need to move up the learning curve faster than the company changes, and the only way to do that is to hire really good people and systematically train yourself.
“Systematically training yourself” means regularly setting aside time to think about: what will my job become? What skills will I need to learn? How long will it take to learn them?
For me, reading was critically important (see: What are the most important books for startup founders to read?). Having a variety of mentors and friends — some a few steps ahead, some many steps ahead — also gave me a lot of perspective.
Finally, you need a growth mindset. I’ve found that just about everything is trainable, including things that seem innate. You can learn to be more confident, a better speaker, a more inspiring person, or whatever skill you want to develop. But you need to be patient with yourself — many of these things are like playing an instrument. You won’t make much progress in five days but you’d be surprised what you can do in five years.