Mike Maples Jr. (@m2jr) taught me the fundamentals of angel investing back in 2007/2008, and I’ve been revisiting my Kindle highlights of his book Pattern Breakers. One simple distinction from from the book worth revisiting often is this: are your customers interested or desperate? My new short post on the subject, including real-world examples:

On The Importance of Desperate Customers - The Blog of Author Tim Ferriss

Source: https://tim.blog/2026/06/01/desperate-customers/ I’ve been revisiting my Kindle highlights ofPattern Breakers, co-authored by legendary angel investor and friendMike Maples Jr.

Mike was the kind soul whotaught me the fundamentals of angel investingback in 2007/2008. He deserves a lot of credit forthe wild startup adventuresthat followed. He’s one of my favorite people in Silicon Valley, a co-founding partner atFloodgate, and has been on theForbesMidas List eight times in the last decade.

Of course, Mike’s principles apply to founding or investing in early-stage tech companies, but many of them also apply to evaluating public stocks or creating anything for the wider world.

One simple distinction fromPattern Breakersworth revisiting often is this:interestedvs.desperate.

Mike writes:

[Some of these startups] embraced all the tenets of disciplined entrepreneurship. But, still, something’s missing. They aren’t getting the traction they expected. Why? Because customers are interested in what they have built, but they are not desperate for it. Suddenly you realize that your idea isn’t big enough. You followed the best practices for good execution, yet you’ve encountered the pitfall mentioned earlier in this chapter: settling for a limited upside, the dreaded local maximum. … Ultimately, in a start-up, there is a huge cultural difference between finding any number of desperate customers versus zero desperate customers. Many start-ups have a huge theoretical market opportunity but never find a single customer desperate for what they propose to build.

Seeking desperation—a signal for a potentially valuable problem to solve—starts early. One early testing ground is the “implementation prototype”:

Implementation prototype: A focused deliverable that helps you engage potential early believers to identify: What is the most important benefit? Who are the most desperate customers?

To get to the right product and the right business, you have to ask the right questions. Two examples:

In the case of Chegg, the most important question was “What is the limit of someone’s willingness to pay to rent a textbook?” In the case of Okta, it was “What is the most urgent management problem early-adopter cloud customers are trying to solve right now?”

Don’t ask whether peoplelikewhat you’re planning to make.

People can love or hate what you’re creating, but you don’t want to land in the mild middle.

This applies to writing books, building companies, making crochet socks on Etsy, and a million other projects and paths.

The real name of the game is this: How quickly and clearly can you find your1,000 True Fans? Sometimes, starting small is what allows you to go big.