2023-09-13

Well my day in a rapper’s entourage is over and what a weird experience it was. Hilariously, I found out that there was a Rue Ryan AND an Avenue Ryan in the city some 15 km apart on different sides of the airport. So there was a hundred dollar taxi ride around a part of town I don’t usually see.

But even after a twenty something minute detour I was then so early to the VIP lounge that there was nobody there and no lights on so I wondered around a bit and bumped into security. They told me that I did in fact have the correct door but that people don’t usually arrive so early. There I am, acting like a poor person again and arriving at the airport an hour and a half before the flight time.

The security folks called across to the lounge to make sure I could get in and I was greeted with the enthusiasm and hospitality of a professionalism of a customer satisfaction rep. Anne asked me about my accident, and how I arrived in Canada. In hindsight a very clever play, in the space of 15 minutes she had most of my life story and yet I know absolutely nothing of hers. Although I did appreciate some of her assessments. When I refused her offers of coffee or tea, she instantly switched to “well a do have a selection of tequilas”. Bit early for that, but I think that confirms my suspicions that tequila is the new scotch.

The jet itself was a little underwhelming. The decoration was that of “fancy caravan”, with the sofa being functional foam rather than a real sofa. But us poor folks still sat in the back which meant that we got to experience takeoff sideways. Which is surprisingly unpleasant as soon as the nose pulls up and you’re thrown sideways.

Interesting to see how the other half lives though. The eight of us had climbed aboard and were sat waiting in the aircraft, when the boss makes the predictable big balled move of turning up twenty minutes late and having her SUV drive across the tarmac to the plane’s stairs. The pilot obviously knew her by name and had prepared her coffee.

On the other end, a motorcade of blacked out SUVs worthy of the president in a knockoff TV show drove to the plan and whisked us away to our destination. Formation driving on the highway drew the horns of a few truck drivers, but our own chauffeur appeared to have not been programmed with emotions.

The drivers dropped us off at a discreet distance from the main entrance to our destination such that nobody looking out a window would notice our arrival.

The meeting itself was brisk, but surprisingly uneventful. It wasn’t quite the bloodbath of lusty hard selling I’d perhaps hoped it would be. Context was set ahead of time and it was mostly just pleasantries with a clear expectation that we’d be working again, just as soon as they’d got a rubber stamp on the finances for next year.

After that we were whisked away in the same SUVs and taken directly to the plane. Within 20 minutes we were in the air.

I wouldn’t rate the private plan experience as any better than business class. But not having to deal with crowds at an airport. The huge queues at drop off and the taxi rank of leaving. Just walking onto a plane without security demanding you take everything apart. Heck! I just grabbed some water and walked on the plane with a bottle. The private terminal experience was amazing. And of course, the lack of the constant clock watching. You know you’re never going to miss the plane when the plane is waiting for you.

I would estimate that the whole experience was probably around the $10k mark. But considering nine of us travelled down and Air Canada was wanting over $1000 per person last minute. There is definitely a case to be made for it.

I’ll be surprised if I have a day again anytime in the future where anyone tries to give me so many bottles of free water !

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2023-09-12

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2023-09-15

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.