Really, really good blog posts on building, scaling, and financing startups

How not to die by Paul Graham (2007). "As long as you've made something that a few users are ecstatic about, you're on the right track. It will be good for your morale to have even a handful of users who really love you, and startups run on morale. But also it will tell you what to focus on. What is it about you that they love? Can you do more of that? Where can you find more people who love that sort of thing? As long as you have some core of users who love you, all you have to do is expand it. It may take a while, but as long as you keep plugging away, you'll win in the end.” Pair with Do things that don’t scale (2013). 

How much funding is too little? Too much? by Marc Andreeseen (2007). The most important part of this piece is the final third, the part that starts with “How much money is too much? There are downside consequences to raising too much money.” If you are a founder who recently raised venture capital I would strongly encourage you to read this part over 17 or 18 times. I have seen every one of these things happen in our portfolio companies (often many times).

All revenue is not created equal: The keys to the 10x revenue club by Bill Gurley (2011). Beginning with the end in mind. Gurley’s business worldview is grounded in Michael Porter (and Michael Mauboussin) which is why he is so good at taking public company valuation concepts and applying them to early stage businesses.

The unprofitable SaaS business model trap by Jason Cohen (2013). This is essentially a primer on the key drivers behind SaaS economics, written almost a decade ago when much of this was novel and not yet well-understood. It answers some basic questions such as “why is seemingly every SaaS company unprofitable?” and explains why you need to get clever around finding leverage anywhere you can in your P&L (via net expansion, CAC, and cost of sales).

I also enjoy some of the anachronisms, like companies IPOing with $60m in revenues, or 75% being a “great retention rate”.

A framework for your first SaaS comp plan by Jason Lemkin (2013). Required reading if you came out of a very large company and need to unlearn everything you know about sales management.

Speed matters: Why working quickly is more important than it seems by James Somers (2015). "If customers find out that you take two months to frame photos, they’ll go to another frame shop. If contributors discover that you’re slow to merge pull requests, they’ll stop contributing. Unresponsive systems are sad. They’re like buildings grown over with moss. They’re a kind of memento mori. People would rather be reminded of life. They’ll leave for places that get back to them quickly.” 

Startups are risk bundles and How to de-risk a startup, both by Leo Polovets (2016). This is a must-read answer to the question of “what are early stage investors looking to see in my company?” and a good reminder that all attributes of your business (traction, team, competition) exist on a continuum.

ZIRP explains the world by Ranjan Roy (2020). An excellent overview of the distorting effects of ZIRP (“zero interest rate policy”) and how this was a catalyst for the technology booms (crypto, WeWork, delivery) that came after the Financial Crisis. A good reminder that macroeconomics provides the backdrop behind which various kinds of companies can or cannot be successful.

Your board of directors is probably going to fire you by Jerry Neumann (2021). Not really, but… you know, maybe.

The wrong bet: The next decade in SaaS won’t look like the last by Buck on Software (2021). Pair with Declining returns in software & defensibility (2023).