Learning the “whole” business

Last year, I went full-time on my productized service. In just over a year without any funding, we’ve now got over 60 clients and 130 freelance writers.

The thing is, I couldn’t have grown this quickly, hired this many people, or built scalable systems like this without the nearly 10 years of startup engineering experience I had before.

If you want to start your own business someday, the best thing you can do is join a small business or early stage startup.

I probably made less money by working at small companies (especially because none of the equity every really amounted to much), but seeing three companies go from 1 to 10 employees was invaluable for understanding what really matters when you get started.

For example, I saw every startup I worked for overindexed on cool products and underinvested in understanding customers. The biggest wins we had were when the market demanded something from us and we responded.

I also learned what matters in early stage company hires. For example, you don’t want to bring on managers or senior level people until you have the infrastructure and challenging work they’ll want to do. A lot of startups mistakenly hire senior people when junior people with good documentation and training is all they really need.

Finally, I saw all the administrative tasks that startup founders need to take on. Before I started, I had a lawyer, bookkeeper, LLC, and a lot of other paperwork ready because I had seen how annoying it would be to set up later.

Anyway, if you’re on the fence between big company or small company jobs while you get your side project off the ground, let me just say, the confidence and learning you get at a startup far outweighs the extra cash you’ll get at a big company.

I talked more about this on the Insights Into Success Podcast last week if you want to hear more about the early days at Draft.dev.