Think Until it Hurts: A Startup Manifesto

“Look, he owns Pan-Am. He owns Congress, he owns the Civil Aeronautics Board, but he does not own the sky!”
- Howard Hughes, as depicted in The Aviator
“All the problems of the world could be settled easily if men were only willing to think. The trouble is that men very often resort to all sorts of devices in order not to think, because thinking is such hard work.”
- Thomas J. Watson, Builder of IBM

I have been a businessman, and a founder, and a software developer. I haven’t been an investor yet but I’ve seen millions of dollars flow from them into various projects, including my own.

I’ve seen good, earnest people spend years and much of their own money doing what they thought they were supposed to do: getting into the arena and trying to make something.

I’ve seen developers take tens or hundreds of thousands of dollars to develop a half-baked idea.

But one thing I have almost never seen or heard of is a founder exhaustively using the one relatively unlimited resource they have: their own thinking.

Let’s not even get into business models, competitive advantage, etc. Let’s just focus on the product. Thinking about a product idea is free. Envisioning something people value and pay for is, in embryo, a startup.

I sincerely doubt that 99% of people in the world who have a potentially promising entrepreneurial idea even take one step. Even the step of jotting it down on a Post-It.

But of those who take some kind of step, the few thousands or tens of thousands per year, how many push themselves to think about their idea as hard as humanly possible, to express it as clearly as they are able, to exhaust the various ways to explore and test their concept (which are often free)?

And, while we’re at it, how many experts and professionals and institutions and service providers who should damn well know better push new founders to do any of this legwork before taking their money?

Where the founder is not also developing their own idea (although sometimes then too), here’s what almost every single software project I’ve seen or heard about looks like: some general business idea is expressed (Uber/Tinder/Whatsapp for something — people will love it!), a cursory planning process occurs (which if it does at all you’re already at Varsity level, relatively), and then there’s a rush to develop with all the determination and clear headedness of a late stage pub crawl. If some third party provider musters up a document with the title ‘Specification’ somewhere at the top then they deserve a medal for nearly heroic resistance to the inevitable.

Somehow I’m pretty sure skyscrapers and jet airplanes aren’t built this way.

There’s something about the infinitely flexible potential of software that makes many people lose their minds and throw thousands or millions of dollars and hundreds or thousands of hours at half baked ideas.

But this is all backwards: thinking is fast, lightning fast, and infinitely flexible. Not only is it fast, if you lean into it (hard and rare as that truly is) it can be magical.

Building software is (for the overwhelming majority) about as fast and flexible as drying cement. And much like cement, once it’s in progress the opportunity to change anything rapidly evaporates.

So I’m going to nail some Theses on the door of the Silicon Valley village church for first time entrepreneurs:

  1. Developers shouldn’t take money from unprepared Founders. This is more or less fraud. Or at best malpractice, negligence, and a waste of our time.
  2. Founders don’t need to be coders, designers, product managers, or experienced entrepreneurs, though any of these help.
  3. However, Founders must think very, very hard before starting, and only decide to spend their or others’ time and money once they’ve thought so much and expressed their thoughts so clearly, as clearly as they can, that it makes them nearly physically ill to think any more. The following is all for the Founder.
  4. Thinking is free. Its ROI is potentially infinite.
  5. Thinking inside your own head is just the start.
  6. Write a lot about your idea. About why it’s special. About why the world needs it. About why everything sucks until your brilliant innovation fixes the problem.
  7. Write very little: summarize your thoughts into a very short space. Start with a page. End with a postcard. Go through a stack of postcards until you get to the last one.
  8. Draw. Take a pencil and a piece of paper and draw what your product looks like, what it does, who uses it, how they use it, how it makes them happy, what different processes occur, what concepts are involved. Draw stick figures and a smiling sun and a box with boxes in it with labels if that’s all you can do. Draw until it’s all on one page and it’s beautiful and amazing.
  9. Read. Read everything you possibly can about your topic. Read until everyone starts repeating the same ideas.
  10. Write more. This time break your idea into parts. What does each part do? Why does it matter? How does the user experience it? Why does the user need it?
  11. Talk, and listen. Try to talk to 100 friends. Talk to 100 strangers. (Are you afraid to talk to strangers? What makes you think the cold, heartless void of the market will be any more merciful?) What about your idea do they like? What do you learn from talking about it?
  12. Research. How did people solve this problem in the past? How do you know it’s a problem? Who else is trying to solve it? If you can’t think of anyone, you’re wrong.
  13. Talk to some experts. Share your best writings and your drawings, get their feedback. Write and draw more.
  14. If humanly possible, develop some time consuming, manual way if necessary to deliver your idea to anyone willing to pay you for it. Even one person. Can you make any tiny version of what you want to do, however inefficiently, that someone is willing to pay for?
  15. Imagine yourself totally failing. Imagine launching your idea and getting no interest from anyone, no users, no revenue. Imagine how you’d react, and what you’d wish you had done differently.

[Updates from the network, paraphrasing:]

  • Talk to as many potential customers as you can find. Learn about their problems. Find out what they do today. Try your best to understand their point of view, their priorities and how you can help. The “ inside of your head is wonderful, but there’s also a very important outside.”— ㋡ Miko Matsumura™

Maybe, MAYBE, after you’ve done all of this you’re ready to begin as a Founder. But if someone wants to take your money to build your idea before you’ve done any of it, run.


The feeling of finally getting the motivation to build something is a beautiful thing. The excitement can feel utopian, often manic. But it’s no fun at all to finally get the great new sports car and immediately crash it. There is a way to harness all of this energy and still be smart. They’re not mutually exclusive.

If you enjoyed reading this post, please recommend and share it to help others find it!

I’m currently working with very talented colleagues to develop some resources that will help new, first time founders get a lot further on a lot less as long as they’re willing to think hard. If you’d like to learn more drop me a line.