I’ve been revisiting my Kindle highlights of Pattern Breakers, co-authored by legendary angel investor and friend Mike Maples Jr.
Mike was the kind soul who taught me the fundamentals of angel investing back in 2007/2008. He deserves a lot of credit for the wild startup adventures that followed. He’s one of my favorite people in Silicon Valley, he’s a co-founding partner at Floodgate, and he has been on the Forbes Midas 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 from Pattern Breakers worth revisiting often is this: interested vs. 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 people like what 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 your 1,000 True Fans? Sometimes, starting small is what allows you to go big.
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How many startup founders and company owners smile when they hear the story of the Mexican fisherman and the American stock broker in 4HWW? I sure do, and modeled my company to provide enough revenue to make a living within the local maximum only. I’m curious, what are examples of companies that live long-term within their local maximum, while staying dedicated to the kind of career Mastery that results in occasional BIG, hairy, audacious goals?
Love this, Joel. Yes and yes.
Hey Tim! Not sure if you’ll read this but I wanted to say thank you for something you taught us in your interview on Diary of a CEO in November 2025. You mentioned how people can become conversationally fluent in Spanish (or most any language) by focusing on the most frequent 1,500 words, because they cover 80% of spoken conversations.
A lightbulb went off when you said this, and I decided to design a language learning app called Lexium based around this premise. The science behind this comes from “Zipf’s Law” in linguistic studies, showing how words cluster exponentially around use frequency.
The app went live for iOS recently, so I just wanted to thank you for the inspiration and drawing attention to how there are smarter ways to learn languages. I had a blast building the app and hope people who are interested in learning languages will have an easier time on their journey!
Yes. The value of “extreme need” customers can’t be overstated. Dan Pope of the Hungry Podcast just said this on Linked In about how he grew sponsorships:
On Zoom calls, with potential sponsors, I’d always say “I could put you in front of 267,00 people who have a mild interest in your service” “or 113 people who NEED your service to grow their business, they control budgets, and could be your client by Friday noon this week”
How rich is rich enough? If your aim is to lead and help might you discuss the corruption that takes apart our governing bodies? The word blithe comes to mind.
Nice post 👍
Thanks for this reminder to not aim for the “mild middle”. Otherwise I am either hedging my bets or I am not fully aware if what others need. I’m saving this question (now generalized): “What is the most urgent problem my clients/customers are trying to solve right now?”
Desperation is a better framing than the SV status quo of “problem to be solved.” There are a lot of tactical problems that don’t have any desperation behind them.
For example, I’m reminded of one of Chris Paik’s essays: “Never underestimate a person’s willingness to pay to close the gap between how the world perceives them and how they perceive themselves.” Elasticity of Demand
Kind of incredible that despite this being absolute gold, I am the first comment. It certainly says something about the ratio of signal to appreciation.
Wonderful insight, keep up the great work.
Love this reminder, and the brilliant power in a carefully selected word: desperate.
Thanks Tim! The timing of this is perfect as I plug away in the evenings on my own little project. Now I can desperately look for what my desperate customers need! Cheers from Wellington, New Zealand!
Tim, the AI generated thumbnails on Youtube are so, SO tacky. For a supposed artist, and someone with the money to support actual artists, it’s such a massive turnoff that you are using such a cheap tactic especially when you had a perfectly fine template already.