Six Questions That Start Startups

This is a repost from my article on Medium.

I collect heuristics: processes that enable problem solving, learning, or discovery. One of my favorite collections is what I call “Questions that Start Startups.” It’s a set of patterns designed to help to overcome schlep blindness and see opportunities to change the world. Here are a few:

1. Why? What If? How?

In A More Beautiful Question, Warren Berger suggests that innovation begins with inquiry. In order to uncover problems and formulate solutions, you should continually ask “Why?”, “What if…?”, and “How?”

Let’s look at an example using peer to peer money transfer:

  1. Why is it expensive and slow to transfer money electronically between two people? The Automated Clearing House (ACH) model isn’t real-time. Instead, it’s a batch process that runs three times per day and involves five entities: you, your bank, the recipient, their bank, and the central bank. Transactions are all sent through the central bank, rather than banks talking directly to each other in real-time.
  2. What if we could transfer money directly from person to person safely and in real-time?
  3. How? Distribute all transactions publicly to facilitate auditing (no central bank). Cryptographically sign transactions to prove my identity. Collectively confirm transactions and make them immutable for future distribution. We shall call it Bitcoin.

2. Live in the future. What seems interesting?

Paul Graham has written extensively on how to find an idea for your next startup. In How to Get Startup Ideas, he offers this piece of wisdom:

Live in the future and build what seems interesting.

In other words, instead of brainstorming ideas with the potential to become a billion dollar business, look ahead several years and pick problems that would be cool to work on. As PG notes, Facebook, Apple, and Google all started as “toy” solutions to “cool” problems.

3. How could I help a billion people within 10 years?

Singularity University was founded in 2008 by Ray Kurzweil and Peter Diamandis. Its goal is to gather leaders from across industries and challenge them to change the world by asking:

How would you tackle the problem of helping a billion people in ten years?

It’s a well worded question. It forces you to “zoom out” and address problems of a huge magnitude like food, water, shelter, transportation, and income inequality. These problems can be overlooked by people who don’t immediately suffer from them, like most Silicon Valley technologists. Asking “how” presupposes that innovation is possible.

4. What are the fundamental truths?

Elon Musk is a co-founder of Paypal, SpaceX, and Tesla Motors. Each company has been the source of massive innovation.

So how does he innovate in industries where others have failed for decades? Musk calls his approach Reasoning from First Principles. It involves two steps:

  1. Ask “What are we sure is true?” about a concept. Strip away all assumptions, leaving just facts.
  2. Reason up from these fundamental truths to a solution.

Here’s an excerpt of Musk explaining his method to Kevin Rose on Foundation:

5. What important truth do very few people agree with you on?

Peter Thiel’s CS183: Startup class at Stanford is a treasure trove of deep thinking about startups. Blake Masters did a phenomenal job transcribing the lectures he attended. Be sure to check out his new book, Zero to One, co-authored with Peter Thiel himself.

One of my favorite lectures is 11: Secrets. Secrets are not widely known or accepted answers to hard questions. The “hard”ness of the question creates a barrier to entry, and a “not widely known” answer creates a competitive advantage for the person who knows it.

To uncover what secrets you know, Peter advocates asking:

What important truth do very few people agree with me on?

In a business context, that translates to:

What great company is no one starting?

6. What steps can I remove?

Long, cumbersome processes are excellent opportunities for innovation. Removing, consolidating, or outsourcing steps in the process can lead to improvement.

One way to find an idea for your next startup is described by Nathan Kontny:

  1. Find a job people have.
  2. List out every step people take to complete that job.
  3. Remove as many steps as possible.

A great example of this is Shyp. If you sell products online you’ve probably experienced how much of a pain shipping is. Typically you must:

  1. Sell your product.
  2. Package it (assuming you have a box that fits).
  3. Buy a shipping label.
  4. Drop the package off at a post office or schedule a courier pickup.
  5. Send the tracking number to the customer.

Shyp removes steps 2-5. Take a photo of your product using Shyp’s iPhone app and a Shyp Hero will arrive to pickup, pack, and ship your product for you.


During a Y Combinator dinner, Paul Graham drew this graph:

The Startup Curve. Property of Silicon Alley Insider, avc.com and PG

The Startup Curve. Property of Silicon Alley Insider, avc.com and PG

Finding a great problem to work on is only the first step in a very long startup journey. Optimize for problems you’re passionate about to make it past the Trough of Sorrow.

I hope these questions above help you find your next adventure.

You can find me on Twitter and AngelList. Say hi.