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Should you Start a Startup? 🚀
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Should you Start a Startup? 🚀

An opinionated take from an ex VC-backed founder, now turned bootstrapped creator.

Luca Rossi's avatar
Luca Rossi
Mar 06, 2024
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Should you Start a Startup? 🚀
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As I have written other times, my professional life has been made up of three main experiences so far:

  1. 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.

  2. I have been Head of Engineering at Translated for about one year — a larger, 150-people tech company working on AI and translation services.

  3. 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!

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