It’s been an incredible year and one I’m grateful for. The most gratifying thing writing this blog is the feedback from readers who say the content is useful. That’s the goal. Thank you for making this so much fun and deeply rewarding.

These are the top posts of 2019 with some commentary and behind the scenes notes on each.

1. 1.01^365 = 37.7 - The idea behind this post is that small, daily improvement leads to huge compounding gains. A 1% daily improvement yields a 37x improvement in a year!
2. Setting the Salesforce/Tableau Acquisition in Context - A wave of consolidation swept the BI industry. Salesforce bought Tableau. Google bought Looker for $2.7B and I was so lucky to have a front row seat. This article talked about the sizes of these acquisition relative to history.
3. Mattermost’s $50M Series B - We are big believers in open source. We’ve invested in more than 15 open source companies over the last 15 years (eg, Hashicorp, Cockroach Labs, Dremio…). Less than 9 months after leading the A, Mattermost raised a large B to push forward open source chat and chatops.
4. The 37% Rule: How to Decide When to Stop Wondering and Start Deciding: I read Algorithms to Live By, which was terrific. And then I listened to a podcast from the author who reminded me about this simple math principle that gives me confidence about making quick decisions.
5. What a Valuation Implies About a Business: I’m curious about the way different investors value different businesses. And for a long time, I wondered how to translate the valuation multiples of a company into a more tangible concept. This is my mental model.
6. A Clever Hack to Reading More Books: There’s so much knowledge in books, and as a society we’re spending less and less time with books. It’s a format that is in slow decline. One way of reading more books is to reduce the cost of them. Here’s my hack to do exactly that!
7. The SaaS Valuation Environment in Mid-2019: 2019 saw the highest valuation environment for SaaS companies for the last 15 years. This chart documented the rise from about a 3.3x EV/forward rev to a 9.5x. A few months later, the market would hit 10.5x forward. Now we’ve regressed a bit, which is good thing.
8. Observations from the Enterprise Tech 30 List - Wing.vc ran a coaches poll of the most promising startups. I broke down the buyers, the layers of the stack they belong to, and the customer size segment to see if patterns exist. Redpoint invested in 8 of the 30, more than any other venture firm.
9. A Random Walk Down Sand Hill Road - Mental models are supremely powerful. There’s a book called The Model Thinker that delves deep into the topic, showing you the math of why you should play basketball faster if you shoot better; and the implications of different types of social networks.
10. The Fundraising Environment in 2019 - Three Major Shifts - At the beginning of the year, the ICO was a thing, and that’s gone for now. But the broader trend is financial products aren’t discrete any more. They are continuous. And the monikers no longer carry meaning. A $7m round might be a seed, a series A or a Series B. Time to jettison the labels and just use the numbers.
11. Before You Raise a Round of Funding, Ask Yourself This Question - Make sure you do plan your options grants for key hires and employees before raising a round of capital.
12. Why Product Innovation Slows After the Series A - The transition from finding product market fit to scaling has real costs, and they appear in the product innovation cadence.
13. That Will Never Work - The history of Netflix is a fascinating adventure. Marc Randolph, the founder who is also part of Looker’s board, narrates the wild ride.
14. Why Churn Rates Can Spike When Your SaaS Startup Experiences Hypergrowth - An important nuance when evaluating churn for your company.
15. The Benefits of and Questions Facing Remote and Distributed Startups - One major trend for 2019 and for 2020 is the rise of distributed companies. I explored the pros and cons of this corporate structure. Regardless of the cons, distributed teams are an inexorable force in startupland, analogous to globalization in the the broader economy.