All Is Well, Everything Is a Mess
January 2026
The best opportunities are obvious in hindsight. Why can't we all see them earlier?
The Tyranny of Legibility
Governments, investors, and large organizations want clean data tables, standardized metrics, smooth trend lines. Legibility creates common language and reduces variation. When everyone measures things the same way, we can compare, benchmark, and coordinate at scale.
But legibility smooths out reality's spikes. It turns messy experiences into averaged aggregates. We lose the secrets in that smoothing process.
James C. Scott wrote that high-modernist planning fails because it ignores "mētis," the local, practical knowledge that can't be captured in spreadsheets. The real texture of how people actually live, work, and solve problems gets lost when we prioritize what's easy to measure over what's true.
To find secrets, you can't float above the surface looking at trend lines. You have to touch the bottom of the ocean and feel the spikes.
The 50% Solution
For every complex problem there is an answer that is clear, simple, and wrong.
Smoothing out the spikes leads to solutions that do 50% of what's needed for 100% of people. For any individual user, that delivers roughly zero value. The averaged solution solves the averaged problem, which solves no one's actual problem.
Within those spikes, in the variation we've smoothed away, people have already found better ways to do things. They've created workarounds, developed informal systems, cobbled together solutions that work for them. They just need someone to notice and formalize what they're already doing.
Secrets in Practice
Before Uber, my friends and I saved the phone numbers of reliable drivers. We knew which ones would show up, wouldn't gouge us, and accepted our preferred payment method. This wasn't fringe behavior. It was widespread enough that you'd share driver numbers like restaurant recommendations. The solution was hiding in plain sight.
At Shiftsmart, we discovered that gig workers were using multiple phones to stack shifts across different apps. The system was so bad that people were buying extra devices to make it work. Give them a single place to find jobs and get paid quickly, and you're serving what turns out to be a massive workforce. COVID made this more visible, but that's another story.
Starbucks was ubiquitous. But if you went to Starbucks locations, the experience had deteriorated. Overcrowded, chaotic, aesthetically sterile. Blank Street offers something that looks and feels good. Suddenly there's a new model. Coffee wasn't done if you looked at the obvious reality of what people were experiencing day to day.
I'm watching Geeta build Van Goethem Diamonds. She's found people tired of choosing between massive brand markups and low-trust direct dealers. They discover her on TikTok, build trust through her content, and solve their own problem of where to get jewelry they can afford and trust. The need was always there. It just wasn't legible in industry reports.
Open Secrets
My goal is to notice, and hopefully improve, places where there's an open secret about how bad an experience is. Here are a few on my mind:
LinkedIn is the most valuable social network for business, yet it's drowning in low-quality, bait-y content. People pump meaningless advice, contrived anecdotes, and disguised sales pitches into LLMs and post nonstop. The algorithm rewards this behavior. There's real appetite for thoughtful content about how companies and individuals solved problems, but LinkedIn isn't a reliable place to get that knowledge.
Customer Success in the AI era is broken. The value-generating moments in software were contracting and renewals, so org design followed suit. But as we sell AI transactions and outcomes, contracting matters less than ongoing usage and value delivery. Revenue cycle management (measurement, attribution, collection) will require new skills that historical CS practitioners need to develop.
Business hotels are awful. From check-in to basic amenities (water, coffee), the cookie-cutter chain hotel delivers mediocre experiences that business travelers charge to their companies. Enormous money being made, minimal customer value provided.
Startup equity remains opaque and impossible for employees to understand. Before accepting an offer, while vesting shares, and after leaving. This is supposed to be one of the huge benefits of startup work, yet the experience of navigating it is terrible.
Mass-market clothing has deteriorated. The quality at mainstream brands has fallen off a cliff, but people keep buying because the alternative (figuring out better options) requires too much work. The race to the bottom is legible in margin expansion. What's not captured is the dissatisfaction people feel every time they buy something that falls apart in six months.
There Is So Much to Improve
The spikes are where the secrets live. You just have to be willing to feel them.