2026-08-02 19:34:00
A teammate shared a lesson this week that a former CEO used to talk about: don’t pave the cow path.
It’s a beautiful warning against taking an inefficient, accidental process and simply making it faster or more permanent.
The image behind it is perfect. Cow paths are meandering trails worn into the ground by cattle wandering more or less at random. When towns grew up around them, people often just paved right over those crooked trails — locking in routes that no one would ever have designed on purpose.
It has no shortage of applications today. We inherit a clunky workflow and reach straight for automation, never pausing to ask whether the workflow should exist in the first place. Speed up a broken process and all you’ve got is a faster broken process — a nicely paved cow path.
So before automating, it’s worth the time to figure out whether you’re automating the right thing at all.
Don’t pave the cow path.
2026-08-01 19:49:00
#OurWorldIsAwesome – Edition 23 | Context on this series – we live in a beautiful world and National Parks are akin to the crown jewels of this planet. These landscapes remind us of the fine balance and complexity woven into the fabric of the world around us. Every time I spend a while inside one of these places, I’m reminded of how precious that balance is, and how much it matters that we try to understand the complexity and our own small role within it.
I think that’s what awe really is. We reach for the word “awesome” in the moments something helps us see our own insignificance — and windows into nature do that for me every time. So this is my small way of sharing it, and passing it along.
It’s hard to visit Jasper and not reckon with the wildfire of 2024. The evidence goes on for miles — hillside after hillside of blackened, branchless trunks. It feels like walking through a forest graveyard.
It was fascinating to understand the why. For thousands of years, the Indigenous people who lived here understood fire as part of a healthy forest — regular, small burns that cleared out dead wood and made room for new growth. They regularly left their campfires burning because the campfire itself told them something about the forest’s health: in a healthy forest it would burn out on its own. In a sick one, thick with deadfall, it would burn and burn.
When the parks were established, that knowledge was pushed out along with the people who held it. Officials suppressed fire for the better part of a century, and the dead wood kept piling up. Jasper, like many National Parks, has since embraced prescribed burning — but it’s playing catch-up against a hundred years of accumulated fuel.
The second amazing thing about the park was the wildlife. For all its remoteness and wildness, Jasper teems with life. Barely a drive along Maligne Lake Road or up to Miette Hot Springs passed without some encounter — an animal at the roadside, a herd in the trees.
My last memory came on the boat across Maligne Lake, out to Spirit Island — one of the canonical images of the Canadian Rockies. High treelines, still water, and trees without end. It has everything that makes these majestic Rockies what they are.
On that same boat, a park ranger said something that’s stayed with me. Home, for most of us, is a place — an address, four walls. For the Indigenous people of this land, she said, home is wherever the sun touches your skin.
It’s a far more expansive way to think about the word. And it leaves a question worth carrying long after you leave: what would the world feel like if we treated every place the way we treat home?
2026-07-31 19:28:00
Eric Weiner had a lovely post about his teenage niece on an airplane — utterly enthralled by the whole thing. The box that lifts into the sky and carries you across the world like a bird. Every part of it a marvel.
It reminded me of an old Louis C.K. bit — everything is amazing, and nobody’s happy. He was brilliant at pointing out how easily we trade wonder for complaint. The seat is cramped, the wifi is slow, the flight is delayed. Meanwhile, we’re sitting in a chair in the sky.
The underlying idea shows up everywhere: happiness is reality over expectations.
The trap is to pour all our energy into the numerator. More, better, faster, growing reality.
But the denominator sits untouched. Expectations quietly creep up, and no amount of growth ever catches them.
And, worse, this happens while a little effort spent lowering expectations tends to return far more than a lot of effort spent raising reality.
2026-07-30 19:31:00
There are always two sides to a story.
You may not like the other side. You may not agree with it. But it certainly exists.
And sometimes, simply acknowledging that it exists is enough to help us make progress.
2026-07-29 19:04:00
I recently started building products focused on healthcare affordability in the US. As I was ramping up on a new space, the biggest question that sparked my curiosity was: how did we get here? This question is the inspiration for this weekly series chronicling the decisions, accidents, and breakthroughs that built the US healthcare system
Over the last several editions, we’ve traced how the US healthcare system accumulated its shape — a wartime wage freeze created employer-sponsored insurance, a tax ruling made it permanent, Medicare and Medicaid covered those the employer system left behind, and EMTALA turned every emergency room into a safety net for everyone else. Each decision solved an immediate problem and created new ones.
Running alongside all of it was an insurance model that was underneath all of it. Today’s story is about that.
In 1929, a hospital administrator in Dallas noticed something in the unpaid bills piling up on his desk. A disproportionate number belonged to schoolteachers.
Justin Ford Kimball was an educator who had a plan for this. As a former Dallas school superintendent who had become executive vice president of Baylor University Hospital, he knew teachers had steady jobs but modest salaries. A hospital stay could wipe them out financially. And when it did, the hospital didn’t get paid either.
His solution was straightforward: 1,250 Dallas teachers could prepay 50 cents a month — $6 a year — for a guaranteed 21-day hospital stay at Baylor. By December 1929, 75% of Dallas teachers had enrolled. The hospital got predictable revenue. The teachers got protection. Two problems, one solution.
The idea spread rapidly. By 1932, community-wide plans offering subscribers a choice of hospitals had emerged across the country. In 1933, a Minnesota administrator named E.A. van Steenwyk put a blue Geneva cross on his stationery — a universal symbol of healthcare — and the name stuck.
The philosophical core of “Blue Cross” was something called community rating. Everyone in a community paid the same premium regardless of age or health status. The healthy subsidized the sick. The young subsidized the old. Risk was pooled across the whole community — not priced to the individual.
This was explicitly a social compact. Boy Scouts handed out brochures. Preachers urged their congregants to join. Blue Shield emerged in 1939 to cover physician services, following the same model. By postwar America, Blue Cross Blue Shield had become one of the most trusted institutions in the country.
Then commercial insurers arrived — and the model that had worked beautifully in isolation met the logic of a competitive market.
Commercial insurers in the 1950s introduced experience rating — pricing premiums based on the actual health profile of a specific group rather than the whole community. A young, healthy workforce at a manufacturing company could now get cheaper coverage than Blue Cross offered. Commercial insurers competed aggressively for those groups.
Blue Cross, committed to community rating, was left covering the older, sicker, more expensive patients the commercial insurers didn’t want.
The math was brutal. As commercial insurers siphoned off the healthy, Blue Cross premiums had to rise to cover an increasingly sick pool. Rising premiums drove away more healthy members. A slow death spiral began because the competitive logic of the market punished the community rating model structurally.
One healthcare economist argued that this dynamic was a direct driver of Medicare and Medicaid in 1965 — that by the early 1960s, commercial insurers had made the elderly and poor effectively uninsurable, forcing the federal government to step in. The employer-based system had left them behind. Now the community rating model was failing them too.
The final blow came from the tax code. In 1986, the Tax Reform Act effectively stripped Blue Cross Blue Shield of its federal tax exemption — ruling that organizations providing commercial-type insurance couldn’t claim nonprofit status. The tax advantage of being nonprofit was gone. The competitive disadvantage of community rating remained.
By the early 1990s, Blues plans were hemorrhaging members — enrollment had fallen from 87 million in 1980 to 66 million by the mid-1990s. Fast-growing for-profit HMOs were taking their market share.
In June 1994, the Blue Cross Blue Shield Association changed its rules. Member plans could now become for-profit organizations for the first time in the association’s history. The primary motivation wasn’t to charge patients more. It was to access capital markets to erase mounting deficits.
Blue Cross of California moved fastest — converting, then acquiring Blues plans across a dozen other states. It was eventually renamed WellPoint, today known as Elevance Health, the second-largest health insurer in the United States. When Blue Cross of California converted, state regulators determined the transaction had failed to protect the organization’s charitable assets. After negotiations, the company agreed to distribute all of its assets — over $3.2 billion — to two grant-making health foundations. The California Endowment and the California HealthCare Foundation both still exist today, funding health access programs across the state.
The Blue Cross Blue Shield story is not a story of corruption or greed. It’s a story of a genuinely good idea — community risk pooling — that was economically unsustainable the moment a competitor was allowed to offer healthy people a better deal.
Once again, nobody made the explicit decision that health insurance should become a for-profit industry. It became one through competitive pressure, tax law, and the logic of markets operating without a defined social purpose.
Once again, we go back to Victor Fuchs’ quote: “Part of the problem is that we have not decided what we want our healthcare system to do.”
Blue Cross Blue Shield is an instructive example of what happens when you build something on a social compact — and then surround it with a market.
2026-07-28 19:17:00
We ate at Otto’s Cache in Jasper recently. The food was good — but the experience was exceptional.
Everybody cared, and it showed. A fork slipped off the table and a replacement appeared within seconds. Someone was always checking in, always happy to help. Warm, attentive, welcoming. It was service at its best.
The same week, we rented a car from Hertz. It hadn’t been cleaned — there was a cup holder filled with leaked orange juice. As I knew better than to ask for help cleaning the car, I asked the counter for a cleaning cloth and got pointed to the bathroom for tissues.
A few days later, we realized that the previous renter had left their Kindle behind in the car. So we called Hertz with a simple ask: reach out to the person on file and let them know we had it. Ten minutes and one supervisor chat later, the answer was no. The employee agreed the request made sense. He just couldn’t act on it.
The magic of Otto’s Cache wasn’t just about a manager setting a high bar. It was that they built an environment where people were given the latitude to figure out how to clear it. Hertz, on the other hand, left its staff wanting to help and unable to.
