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 […]


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 […]


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 […]


Vocabulary for Startups – Part 1 of N

I was recently invited to get an opening talk at Startup Weekend Houston specifically on customer validation. I enjoy developing interview questions and actually talking with potential customers, so it seemed like a great opportunity. As I got closer to the actual presentation, I realized that by jumping into the interview stage, I would be […]


Interview Tip: Passion will Win the Day

Although I attended the event below on behalf of my employer Twilio, this is not necessarily their position on this topic. I write representing my own opinion and thoughts.. Last week, I was tapped to represent Twilio at the Made In Austin recruiting event at University of Texas-Austin. While the event was well-organized, the students […]


Recruiting Investor #2

In the past couple months, I've chatted quite a bit with different startup founders. Most were non-technical people looking for a developer to expand what they have (rare) or build it from the ground up (the vast majority). In all but a few cases, something rubbed me wrong about the conversations… In a few cases, […]