2023-09-08

Maybe it is sleep debt, maybe it is stress and adrenaline leaving the system. But either way, even after an objectively good night (so says the sleep tracker), I feel terrible.

Well not terrible per se. It’s more of a zombie like grogginess. The sort of slow thinking, “the world is too bright” kind of day that really can only be resolved with mimosas, dark glasses and a nap after a pleasant brunch.

Ah brunch! Remember those? They were the most illusive hints at what adult life could be. I mean, they only really unlocked as a thing when I was in Vancouver and pushing 30. But the problem there was that we did not have the financial capital to indulge in such activities very much - only when our more sophisticated friends invite us out. And at that time, even having a coffee outside felt luxurious, so the notion of sitting down on a terrace for a cocktail or mimosa was much above our station.

I remember back in 2018, one of ’s friends took us to a “proper” brunch in New York’s Upper East Side in one of those glorious Americana, dark wood, white tiles and brass fixtures places. I don’t really remember for the food, drink or even what we talked about. What I remember most was the people. It was a big place, and yet we were rammed in tight. I was lead to believe it was the sort of place you had to book at least a week ahead and with precision that bordered upon the scientific.

I left that place with a slight ringing in my ears, like I’d been to some sort of music performance - no doubt from people shouting over the background din of so many people. But there was a definite vibe. A certain vitality to the place. Like everyone there was alive.

Looking back now, I understand why New York was so badly affected by Covid. Not just from the initial contagion perspective but from a cultural impact too.

I think I miss that. I miss being surrounded by busy people, with no agenda of my own. No clock watching. No thinking about the babysitter and having to get back soon. Just having a weekend free, to do as I please when I please. Which right now, would be just about nothing.

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2023-09-07

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2023-09-09

How do you define successful engineering leadership?

The Philosophy

Many view technical leadership as being the “smartest architect in the room.” I see it as the opposite. My job is to build a room where I don’t have to be the smartest person because the systems, culture, and communication are so robust that the team can out-innovate me.

The Strategy

  • Alignment: Does every engineer understand how their sprint task impacts the company’s bottom line?
  • Velocity vs. Stability: We aren’t just “shipping fast”; we are building a predictable, repeatable engine that doesn’t collapse under its own weight at the next order of magnitude.
  • The Human Growth Curve: Success is when the engineering team’s capability evolves faster than the product’s complexity. If the team feels stagnant, the tech stack will soon follow.

What is your approach to scaling technical organizations?

The Philosophy

Scaling isn’t just “hiring more people” - that’s often how you slow down. Scaling is about moving from Individual Heroics to Organizational Systems.

The Strategy

  • The 3-Continent Perspective: Having managed global teams, I focus on “High-Signal Communication.” As you grow, the cost of a meeting triples. I implement “Asynchronous-First” cultures that protect deep-work time while ensuring no one is blocked by a timezone.

  • Modular Autonomy: I advocate for breaking down monolithic teams into autonomous units with clear ownership. This reduces the “communication tax” and allows us to scale the headcount without scaling the bureaucracy.

  • Automation as Infrastructure: At petabyte scale, manual intervention is a failure. I treat the developer experience (CI/CD, observability, self-service infra) as a first-class product to keep the “path to production” frictionless.

How do you balance high-growth velocity with technical stability?

The Philosophy

Technical debt isn’t a “bad thing” to be avoided; it’s a set of historical decisions that no longer serve you. Like any loan, leverage can accelerate growth when investments payoff. But if velocity and returns are slowing you need a payment plan before the interest kills you.

The Strategy

  • The ROI Filter: I don’t refactor for the sake of “clean code.” I don’t refactor a micro-service with no users. I refactor when the pain on that debt - measured in bugs, downtime, or developer frustration - starts to exceed the cost of the fix.

  • Zero-Downtime Culture: Especially at scale, stability is a feature. I implement “Guardrail Engineering” where the system is designed to fail gracefully, ensuring that a Series B growth spike becomes a success story rather than a post-mortem.

  • The 70/20/10 Rule: I typically aim to dedicate 70% of resources to new features, 20% to infrastructure/debt, and 10% to R&D. This ensures we never stop innovating, but we never stop fortifying either.