The 1st Question You Should Ask About Any New Company

The VC vs. bootstrapping debate is the most boring online topic ever invented. Both options are 100% valid because obviously everyone should take their own path.

The important distinction that no one talks about but that actually matters is what strategies and tactics you’ll need to use depending on your ambitions.

“How ambitious are you?”

This should go without saying but no one explicitly says it: you’re going to do very different things if you’re aiming to be Facebook versus Basecamp.

On one hand, some businesses aren’t possible if your ambitions aren’t big enough. Network-based businesses likes Facebook and Uber are good examples of this.

So when someone comes to me with an app idea requires 100 million+ users to be successful, it’s a distraction to talk about whether it’s a “good idea” unless you know what the founder is aiming for.

And on the other hand, some typical startup advice can be very damaging to smaller businesses. For example, trying to grow at all costs.

This is especially important whenever you’re reading so-called business advice online.

Andreessen Horowitz and Y Combinator have awesome info about doing a startup. But if you’re not trying to raise venture capital a lot of it will be irrelevant at best and harmful at worst.1

Make sure you know what you’re looking for a in a business before you listen to advice, and make sure you know what a founder is looking for before you give any advice.


  1. And for god’s sake this isn’t a critique of venture capital as I publish on my venture-funded WordPress blog via my venture-funded MacBook Pro. If only more of us could be as ambitious as Elon Musk and co.