A few times a month, someone in my network introduces me to a fellow GWOT vet who is thinking about starting (or joining) a tech company designed to grow fast (i.e. “a startup”). I often end up having several with them but have noticed I recommend the same articles, books, and open courses. So for the sake of scalability and simplicity, I’m going to just record them all here (and cross-post it to my Substack, which you should sign up for*, PWN THE FUTURE).*
For those of you who want to engage more, here’s my userguide (doc that describes how best to engage with me, given that I’m time-bankrupt due to my young/growing family, my company, etc.). The TLDR: I prefer to engage in the open, via Twitter. No DM’s, just “@ me” (I respond to most DM’s with a public-facing tweet).
Personally, I have found three professional activities in my life that force me to operate on all cylinders: forward-deployed operations in contested environments, no-limit texas hold’em, and startups. In their own way, each one is an exercise in taking incalculable risks. Volatility, uncertainty, complexity, ambiguity. There are ways to decrease specific risks, but certain variables always remain, requiring one’s fullest capacities to bear in order to succeed.
Combine this aptitude with the thrill of building something new, or solving a novel problem with technology, and perhaps starting a “startup” is for you.
But don’t take my word for it, here’s a great interview with YCombinator partner Michael Seibel:
Why Should I Start a Startup?: Becoming a Founder, College Students | Y Combinator
Now that you’ve finished, you might be thinking that you want some more resources to consume before making a decision.
Reading list on motivation:
Zero to One - One part how-to, three parts call-to-action, Blake Masters worked with Peter Thiel to turn his notes from the 2012 CS183: Startup class that Peter was teaching at Stanford into a New York Times bestseller. Personally I like the tumblr notes better, but you can do ZtO on audio book, and it’s of course a bit more polished.
The Secret History of Silicon Valley - Written by Silicon Valley OG (and USAF vet) Steve Blank, this series of essays, and accompanying talk, describe how today’s technology industry is in many ways downstream from several major waves of technological demand from the U.S. military. A great way to spend a few hours to get you in the headspace.
The first and most important thing I recommend to folks who are thinking about working at a startup is to go through the YCombinator Startup School curriculum. It is fifteen lectures given by some of the startup world’s best operators and venture capitalists, covering all of the important facets of “starting a startup”:
Curriculum | Startup School - The Best Resource for Founders
The lectures are great, and in addition, the team at YCombinator has created a cadre-based program that runs multiple times per year and get some informal mentoring, pitch practice, and once you complete the curriculum, access to free resources to help you build a company.
In addition to the lectures and the school, YC also has an online library of sorts with articles about nearly any question you might have regarding starting a startup:
YC Startup Library | Y Combinator
If you’re looking for something even more substantive, there’s also a myriad of programs run by “OnDeck,” a startup that is aiming to create a flywheel of flywheels for founders starting companies, ops people joining companies, engineers helping build companies, and so on. There are various programs with a relatively low price point: