Should you Start a Startup? 🚀
An opinionated take from an ex VC-backed founder, now turned bootstrapped creator.
As I have written other times, my professional life has been made up of three main experiences so far:
I have been co-founder and CTO of Wanderio for 8 years — I raised ~$4M in Italy, grew a 20-ish people team, and served 25M+ customers.
I have been Head of Engineering at Translated for about one year — a larger, 150-people tech company working on AI and translation services.
I am now the creator / writer of Refactoring — the very newsletter you are reading right now. It’s been ~2.5 years so far.
I am grateful to have seen work from different angles — co-founder / manager / creator — but there is no deny my longest and most profound experience has been as a startup founder.
It was my first job out of university (I dropped out of my PhD), and I guess it was my imprinting with the tech world. In fact, startups are still a big part of my identity today: I advise/mentor many, invest in a few, and many Refactoring articles are written with them in mind.
So, people sometimes ask me whether they should start a startup. They may have an idea, sometimes a prototype already, and wonder if they should go all-in.
This question has at least two angles, which are equally important:
💼 Business — is this idea startup-worthy? Are you the right person / team to do it? Is going VC the right route vs e.g. bootstrapping it?
☀️ Personal — would you enjoy being a founder? Is it the right call for your life, and based on everything else you have going on?
These questions are hard. In most cases, answers are murky and there is a lot you can’t predict.
Not asking them, however, is worse.
I have seen far too many startups who had to stay side-projects, founders burning out because life is not what they expected to be, or, conversely, side-projects with fantastic potential that never graduated into businesses.
So let’s try to unpack this. Here is the agenda:
💡 The Right Idea — how to figure out if your idea is worth working on.
💸 VCs vs Bootstrapping — we talk about freedom, bootstrapping, and what VC money is really for.
🏅 Founder Experience — what it is like to be a founder.
Let’s dive in!