Entrepreneurship

A short miniseries capturing the story of a short presidency. It’s fascinating to see the different forms and shapes a presidency can take. It’s a clear reminder that there is no straight path to entrepreneurship. Everyone does it in their own way. James Garfield was the epitome of a classic leader: an eloquent speaker who invigorated crowds. But he didn’t want it. Chester Arthur was a completely different type of leader who found himself in a place he never expected and adapted along the way. He also didn’t want it. ...

I’ve had a lot of conversations this past week with friends from various walks of life. These conversations get deep, sometimes meta, and very introspective. I challenge others, I get challenged myself, and on the other side of the conversation, a bit of clarity emerges. This is not something I spent much time thinking about in my teens and early twenties. Over the last few years, though, I’ve spent a lot more time reflecting on it and have found a way to articulate it. ...

Throughout my career, I’ve had consistent success getting jobs at other companies, both small and large. I bring unique ideas and perspectives to the table. I can build and lead small teams. I can communicate clearly and effectively, endure pain, adapt, and I have the hard skills to learn and execute. I also have well-known weaknesses (impatience, aversion to meetings, self-criticism), but that’s not what this post is about. This post is about my weakest muscles: finding PMF, getting my first real customer, and taking a product from zero to one. ...

In 2014, Alan Kay was a guest lecturer in my programming languages class at the University of Toronto. I thought it was cool, but I definitely did not appreciate it as much as I should have. To this day, one of his infamous quotes still resonates with me: “The best way to predict the future is to create it.” A Pattern I Can’t Ignore With the new year, I’ve been reflecting on my career up until this point. ...

Peter Thiel is well known for his infamous book, Zero to One. In reality, most startups fail, so it probably should have been called Zero or One. The skill set required to go from one to ten, to one hundred, and beyond is broad, iterative, heavily experience-driven, and requires a lot of people serving different functions. But, the jump from zero to one really is a jump. And it isn’t just a skill set. It’s a mindset.

A great 2-minute post by Ross Lazerowitz, CEO at https://www.miragesecurity.ai/ The playbook for enterprise software is: Cold outreach Design Partners First Cohort Love it. But, he calls out that desperation != urgency. Being able to sell and raise doesn’t mean success. It means you might get stuck in a local minima. User need to line up for your product. His key takeaway is: Go slow to go fast. Don’t spin up marketing and a sales team until you feel that pull. If you can’t close $1M without marketing spend and 10 AEs, you might be building something middling. Don’t get distracted by desperation if you can’t find urgency. ...

I took a ferry from Seattle to Victoria, and all I could think about on the way back was: Which company should I buy (not build) to generate free cash flow? If you’re a seasoned software engineer in the age of AI who lives to build, you’re probably thinking how ridiculous this sounds. Well, Andrew Wilkinson planted a tiny seed in my mind, and it has started germinating. Strap in. This post is about making plans without expectations, how that mindset extends into everything else in life, and if you’re a Swiftie, I’ve got something special at the end for you as well. ...

The Demo-to-Product Gap? The March of nines? In AI, the last 0.001% takes 99.999% of the time. We need a name for it, and given how much the Andrej & Dwarkesh interview has been cited, it’s only fair to call it “The Karpathy Principle”. Here is a 30 second YouTube Clip for reference.

Founders create problems. Operators solve them. I’ve met a lot of executives and CTOs who resonate with two things: They like to solve puzzles. They like to be given an end goal and just make it happen. The job of a founder is to identify opportunities (i.e. problems), set a vision for what a solution looks like, and build a team that’s enabled to get there. That idea, of course, comes with plenty of qualifiers and caveats. It simply defines a founder’s end goal, not their day-to-day. ...