Wisdom

I heard a definition of wisdom from Naval Ravikant that’s stayed with me. Wisdom is knowing the long-term consequences of your actions.

It’s a beautiful, analytical way to put it, and I think it captures a real part of what wisdom is.

But there’s a second part. Seeing a trade-off clearly is one skill. Knowing which side of it you’d actually pick is another. The first is analytical. The second asks for a great deal of self-knowledge, and a fair amount of acceptance.

So maybe wisdom is two things held together. Understanding the long-term consequences of your actions, and knowing which of those consequences you could live with without resentment, and still be at peace.

Grumpy Grumperson

There’s a type of person you meet when you’re on holiday. I call them Grumpy Grumperson.

They live in or near the places tourists flock to — famous landmarks, national parks, pretty little towns — and somewhere along the way, they decided they’ll expect visitors to know what the locals know. So they throw their hands up when a car ahead slows to figure out a turn. They honk when they see sense someone is tentative. They shake their heads when someone stands in the wrong part of the sidewalk, breaking a rule that’s obvious to them and invisible to everyone else.

But of course newcomers are still figuring things out. Of course they’ll make mistakes. That’s what being new means. All it takes is a little understanding to meet them there.

All of this inspired a note to myself: don’t be a Grumpy Grumperson. Wherever we live, there are newbies finding their feet.

A little grace goes a long way.

Always reaching, already enough

I came across this line recently and thought it was profound. “Always reaching, already enough.”

It speaks to the power of holding two opposite ideas at once. When you’re secure enough in yourself, you can keep reaching, knowing it might not work out… and that’s okay.

It encapsulates so much of the way I seek to approach life. It went straight into my daily commitments note.

Default alive

A friend running a company was telling me about a run of hard decisions he’d had to make recently to get to a major milestone – hitting cash flow positive. Or, as he put it with a grin, going from “default dead” to “default alive.”

It’s one of those lessons that’s easy to lose track of. Amid the noise of valuations and fundraising, it’s easy to forget that the whole point is to build a profitable business.

Right now there’s a huge gulf between the AI haves and the have-nots. The haves seem exempt from any of this. Profitability, cash flow, none of it appears to matter.

And for now, that’s true. While the party is on, it makes sense to dance.

But the party will end. All parties end eventually.

Which is why I keep coming back to a simple line: people come for the magic, but they stay for the math.

The magic matters enormously. It’s what gets people to the door. And a rare few can hold off the math for a very long time.

But the safe bet is that you’re not one of them. For the rest of us, the math is what keeps the lights on. Better to start making it work as early as we can.

Locations and drill bits

A few years ago, when we were house hunting, a friend gave me a piece of advice I still use. Better to buy a house that needs work in a good location than a perfect house in a bad one. You can renovate a house. But you can’t move it. The location is the one thing you’re stuck with, so it had better be the part worth keeping.

The more I sat with it, the more places it turned up.

Hiring is the obvious one. Better to work with a sprinter who has bad technique than someone with good technique and average potential. Technique you can coach. Raw speed you can’t. It’s hiring for slope, not just intercept.

Then there’s choosing which company to join. Think of it like drilling for oil. Better to be at place that’s struck oil but is drilling with a terrible bit than somewhere with a beautiful bit and no oil under it. You can always swap the bit.

The funny part is that all three analogies – the house, the sprinter, the drill bit – came from the same friend.

Maybe that’s the real lesson. The best ideas are simple and widely applicable. And the role of good stories and analogies is to help us remember them in different contexts.

Banff National Park

#OurWorldIsAwesome – Edition 25 | 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.


Banff was Canada’s first national park, and one of the very first anywhere — the second oldest surviving park in North America, after Yellowstone.

Interestingly, Banff wasn’t established with a grand vision of protecting the wilderness. It started with an argument. In 1883, railway workers found hot springs in the Bow Valley, and the fight over who owned them — and who had the right to profit from them — got messy enough that the government stepped in and set the land aside. Conservation won, almost by accident.

On most lists of the most beautiful places on earth, Banff lands in the top five, and you can see why the moment you see one of the glacial lakes. This is the Peyto Lake.

That impossible blue isn’t a trick of the camera — it comes from rock flour, fine rock ground up by the glaciers and left suspended in the water, scattering the light back as turquoise.

Lake Louise looks similarly splendid (while remaining a frigid 4 degrees Celsius even in the summer) after a hike that involves traversing through snow in the summer.

Then you pair those lakes with peaks you can climb. At Moraine Lake, the Valley of the Ten Peaks rises straight out of the water.

I also loved the many wildlife crossings that have been built in Banff that you can see on the drive. I learnt that there are over 40 overpasses and underpasses built across the Trans-Canada Highway, now so grown over with grass and trees that they look like natural hills.

We didn’t see much wildlife near them as there were far more people than animals at Banff. But the crossings themselves were remarkable because animal-car collisions here have fallen more than 80% since the crossings went in.

Banff National Park earns its place as one of the most beautiful places on this planet. I hope to go back.

Epic Systems – the software that powers everything – American Healthcare Chronicles

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.


To understand why Epic exists, you need to understand what happened to American healthcare after World War II.

The wage freeze of 1942 didn’t just create employer-sponsored insurance — it created a three-way relationship between patients, providers, and payers that hadn’t existed before. A doctor saw a patient. But now a third party — the insurer — decided what to pay, and under what conditions. To get paid, physicians had to document, code, and justify every interaction to a bureaucracy with its own rules.

Medicare and Medicaid in 1965 added the federal government as the largest single payer in the country. The documentation requirements didn’t just continue — they multiplied. A diagnosis needed a code. A procedure needed a code. The attending physician’s notes had to justify both. By the 1970s and 80s, as private insurers followed the same model, getting paid had become a full-time administrative task running parallel to the actual practice of medicine.

This created the conditions for a software behemoth.


In 1979, a computer science graduate student named Judy Faulkner started a company in a Madison, Wisconsin basement with $70,000 borrowed from friends and family. She called it Human Services Computing. Her co-founder wanted to raise venture capital and grow fast. Faulkner refused. He left in 1983.

What Faulkner built — slowly and deliberately over the following two decades — was deceptively simple in concept. A single database. She called it Chronicles. Every clinical record, every billing entry, every scheduling note, every lab result — all of it living in one place, all of it connected. No separate systems that needed to talk to each other. No data loss between the clinical side and the billing side. One source of truth for the entire patient journey.

The contrast with competitors was stark. Cerner, Epic’s main rival, had grown quickly through acquisitions — eventually an amalgamation of 24 different companies stitched together. Integration was always incomplete. Data lived in silos. Chronicles was the opposite of that.

By 2001, Epic had fewer than 90 customers and $50 million in revenue. Then the phone rang.


In 2003, Kaiser Permanente — the largest nonprofit health system in America, the one that appears earlier in this series — issued a request for proposals for a new electronic health record system. The contract was part of a $4 billion infrastructure project covering 30 hospitals, 400 clinics, and 11,000 physicians.

Kaiser’s initial instinct was to split the work. Use Epic for outpatient care — where Epic’s reputation was strongest — and Cerner for everything else. Judy Faulkner said no. Splitting clinical records between two systems meant data loss at the handoff between outpatient and inpatient care. Bad patient experience. Bad medicine. All or nothing.

Kaiser also asked for equity in the deal. Cerner offered 10%. Faulkner said no to that too. Epic didn’t negotiate. It didn’t discount. It didn’t give away equity. They knew they had better software and just prepared harder — Epic’s team flew in the night before the technical due diligence meeting and rebuilt their entire presentation to model Kaiser’s specific transaction flow.

Epic won. Revenue went from $50 million to $162 million almost overnight. The Kaiser deal established Epic as the gold standard for large health systems. The floodgates opened.


Then in 2009, the federal government accelerated everything.

The HITECH Act set aside $27 billion — eventually rising to $35 billion — to incentivize hospitals and providers to adopt electronic health records. In 2008, only 10% of American hospitals used EHRs. The incentives were enormous — up to $44,000 per physician, up to $6.37 million annually per hospital. After 2015, providers who hadn’t adopted EHRs faced Medicare reimbursement reductions.

Epic has faced criticism for its role in drafting the HITECH legislation — Judy Faulkner was involved in the process. Whether that shaped the outcome in Epic’s favor is debated. What’s less debated: Epic was already winning before HITECH. Kaiser had already chosen them. The legislation added tailwinds to a company already on the ascent. It also added complexity — the Meaningful Use requirements created new documentation mandates that compounded the billing burden EHRs were supposed to reduce.

Today Epic supports the records of over 250 million Americans and generates $6.7 billion in annual revenue. Faulkner, who still runs the company at 82, has never taken outside investment, never made an acquisition, and has committed to giving 99% of her assets to charity.


A unified patient record that follows someone across a health system catches drug interactions, flags allergies, and surfaces clinical history at the point of care. Hospital mortality statistics improve meaningfully after EHR implementations mature. MyChart — Epic’s patient portal launched in 1999 — gave patients access to their own records a decade before competitors thought to try it.

And yet physicians today spend roughly half their working hours on EHR documentation. The tool built to manage billing complexity created its own complexity. Doctors enter data not because it helps them treat patients but because it satisfies reimbursement requirements. EHRs became the single most cited cause of physician burnout in the country.

The software that runs American healthcare was built because billing became as complicated as medicine itself. It made medicine safer — and it made being a doctor significantly harder.

Paul Starr’s line applies here too. The dream of reason did not take power into account. Epic didn’t create the billing complexity. It was built to survive it. But in doing so, it became the behemoth that now defines how American healthcare runs — for all its good and all its challenges.

Consider what switching away from Epic actually means. When one major health system attempted to migrate to a different EHR, the project took over a decade and cost tens of billions of dollars — and still wasn’t complete. That’s not a software contract. That’s infrastructure.

Epic controls records for over 250 million Americans, sits at the center of clinical workflows in more than half of US hospital beds, and keeps 35% of its revenue invested in R&D. Every year it expands further — into scheduling, billing, staffing, AI documentation, population health. The question healthcare startups ask isn’t whether to compete with Epic. It’s whether Epic has noticed them yet.

In healthcare technology, you don’t fear running out of runway. You fear ending up on Epic’s roadmap.

H/T: Acquired’s episode on Epic Systems

The Coopers

Two years ago, for a short period in the summer, we had two juvenile Cooper’s hawks call a couple of trees in our backyard home.

Juvenile hawks are still learning to be adults. So they usually make a lot of noise as part of this process. This included chasing squirrels, walking around the yard, and constantly calling on each other at all hours of the day.

A few weeks ago, we had two juveniles show up again. We have no idea if they were connected to the pair who showed up two years ago. But, sure enough, they made themselves at home and woke us up on weekends with a din of high-pitched calls.

I was reminded of a time at home when my grandparents were telling me off for blasting music before heading out for an exam a few months before college.

My mom told me to not bother and told them – “You’ll miss this when he leaves home in a few months.”

They did. And said so many times after.

It is now good advice for me as a parent. But it turns out it was equally good advice for us as temporary juvenile hawk neighbors as well.

Now that they’re gone, we miss the din they created and are grateful for the time they shared space with us.

On its own merits

An experience doesn’t have to be the greatest of all time for you to enjoy it.

It’s easy to fall into the comparison trap. You can compare this place to the last one, this beach to that one from 2 years ago, and so on. Doing so simply lets the memory of one good thing rob us of another.

It takes a quiet kind of discipline to reset our expectations and take an experience on its own merits, rather than dismissing it for all the things it isn’t.

After all, the only Zen on the mountaintop is the Zen you take with you.