How Unprofitable Companies IPO

Disclaimer: In this post, I describe business models of tech companies where I hold positions. Don’t use this to draw conclusions about any specific company or rationalize any particular investment. Follow your own investment strategy, not some knucklehead with a blog. In the last few years, we’ve seen a variety of major tech companies go […]


That Conference Panel on Entrepreneurship

Late last summer, I participated in a panel discussion at my favorite conference of the year: That Conference. Wait, which conference? That Conference! Now that we have that out of the way, let’s dig in.. You can catch the full video here but first some background. If you listen closely, you’ll realize that we have […]


My Reading List (2018)

After college, I resolved to read one book a month. It can be fiction, non-fiction, technical, business-oriented, or whatever as the goal was to always be absorbing and digesting new ideas and information, even just for fun. More recently, I’ve generally tried to read 3 per month which works great with a Kindle and a ton of […]


On Job Titles at Startups

I’ve worked for organizations of every size, from being employee #1 to starting at #25 to a massive US federal department. Further, I’d advised companies starting from a single founder to a couple hundred employees. From being on every side of that, one of the things I’m most sensitive to is job title but probably […]


Building Version 1 is Dangerous

Building software is hard. You have all the fun of being excruciatingly specific in certain situations, incredibly general the rest of the time, and expressing all of it in a language that isn’t your own. In the context of a new product – whether it’s for a startup or an established company – it’s even […]


Gandalf, still not making sense of your docs

The Three Styles of API Documentation

API Documentation comes in a variety of forms. You can find it in pdfs, html, or even a Postman-collection that lets you play immediately. You can provide project examples, detailed blog posts, or video walk throughs.There are tradeoffs of each. Regardless of how you deliver the documentation, all  documentation fall into one of three buckets: […]


The Brand Strategy Canvas

I’m not a branding strategist. I am not a designer. I came into technical marketing through the backdoor of developer evangelism. In terms of my own approaches to marketing, I have reasonably good instincts but nothing resembling formal training. That said, I know when something is awful. A few years ago, my friend and occasional […]