This was originally published in my free weekly newsletter, How It Actually Works.

In Defense of Thinking Bigger

It’s recently become cool to talk about the math behind venture-backed technology startups,and how so few of them achieve their implicit financial goals.

You might have seen funds like Indie.VC, Earnest Capital, Tinyseed… investment funds for bootstrappers. These fill a need in the market for sure. Whether they can be successful is another question, but small companies that don’t want to a billion dollars currently have limited capital sources.

I’ve done the “how many customers do I need a month to make $1m in revenue” more times than I can count. I have multiple spreadsheets showing the different types of products and pricing plans that would get me to that goal.

It was kind of silly.

The problem is that it made my thinking so small. Instead of thinking about how to grow and create value, I thought about how to convince a few specific people to buy a very specific product.

I was shooting for a net worth of e.g. $5 million, so that’s as high as I was ever thinking!

Now I’m around people who are thinking way bigger. It’s changed how I think about what I want to do, and what I could accomplish.

This isn’t to say that everyone should do a big venture-backed startup, or raise a ton of money, or even be an entrepreneur.

It’s just probably true that we each underestimate our potential. We can’t all be Elon Musk, but we can all easily do 3x more, perhaps 10x more, than we each believe.

The Links

Cities and ambition

Paul Graham makes my above point better than I can.

Actionable list of conversational frameworks (twitter)

Example like:

“When confronting somebody:
Instead of ‘Why did you do that?’
Maybe: ‘What was going on for you?’”

and

“When rambling with nowhere to go:

‘I’m going to pause right there for reactions’”

“Inside the mind of a master procrastinator” (video)

Ted talk from Wait But Why writer Tim Urban

A pitch for mediocrity (twitter)

Your weapon against perfectionism.

The truth about hard work (audio)

“Effort is a big deal. And effort is sort an arrival of sorts for society. The ‘look how hard I work, look at how much effort I’m putting in, and therefore I am doing the right thing by doing that.’

“And the problem that arises from that often times is those that are very efficient are demonized.”

You can read all the most popular posts at the full archives.

This was originally published in my weekly newsletter, How It Actually Works.