Jul 6How to mess up a good company and not make any money along the wayA financing to exit cap table breakdown — I wrote previously about the various ways to be wrong in investing here: https://alexoppenheimer.substack.com/p/expensive-options-and-losing-big And I wrote about investing in turbulent markets here: https://alexoppenheimer.substack.com/p/capitalization-and-financing-for But there is one thing I wanted to call out specifically, which is probably the most painful way to be wrong: When you invest early in…Down Round6 min readDown Round6 min read
May 4Capitalization and Financing for a Turbulent MarketAs we continue to see how tougher market conditions impact startups, there’s a deeper, more nuanced reality that depends heavily on the deal terms. When things go consistently great, everyone wins, and when things go consistently poorly, everyone loses (especially at the early stage). When a business OR the market…VC2 min readVC2 min read
Mar 27Understanding and Describing Groups with AveragesMean, Median and Mode Most people learn about averages in math class when they are young. We learn that there is mean, median and mode. There are all supposedly ways to understand and summarize a group of… anything (but mostly just a list of numbers in the class setting). Colloquially…4 min read4 min read
Dec 29, 2022Expensive Options and Losing BigHow to be Wrong Early stage venture investing is all about option betting — whether you’re investing as an angel, a fund or a syndicate, returns are generally driven by a small number of very large successes. The conventional wisdom is that in a fund of 20 companies, one should be able to return…Venture Capital5 min readVenture Capital5 min read
Published inStartup Stash·Nov 16, 2022Valuation And Primary CapitalOverpaying Versus Paying Ahead The capital markets are starting to settle down after the most aggressive venture investment environment ever. The amount of capital deployed in 2021 was absolutely astounding at over $300Bn… and that is just what got announced. As with any massive influx of supply into a market, price goes down. In…Valuation7 min readValuation7 min read
Sep 19, 2022Directional Valuation ModelingFinding Accuracy in a world of low precision — understanding change impact over absolute answers. — There’s no secret that valuations for nascent technology companies are more art than science. …Dcf8 min readDcf8 min read
Aug 17, 2022The Revenue MultipleUnderstanding the Fundamentals of Valuation For the last 10+ years I have been working in the startup world. It moves fast, breaks rules and changes the world — it’s awesome. While some rules do get broken, there are more fundamental rules that do not. …SaaS5 min readSaaS5 min read
May 15, 2022Proxy Valuation ModelingBringing valuation all the way back to the fundamentals… no matter how far in the future they might be. I have been reading a super interesting book called Investing: the Last Liberal Art, very slowly over the last year. I’d recommend it to anyone who wants a slightly different and…Valuation5 min readValuation5 min read
Mar 3, 2022How are SaaS Startups Valued?or how should they be… How are SaaS Startups Valued? I get asked this question all the time. There’s no doubt that the SaaS business model has dominated the last decade (do I even need to list out the SaaS subscriptions you probably paid last month?). And we’re all the better for it: SaaS is…SaaS9 min readSaaS9 min read
Feb 8, 2022Churn — How it works operationally and ways to calculate itThis is an analysis tool for thinking about churn: Churn Calculations Single Cohort Churn Calcs Simulator - why definitions matter by @alexoppenheimer Initial Customers,1,000 Month 1,Month…docs.google.com Anyone who has spent more than 5 minutes thinking or hearing about SaaS companies has certainly bumped into churn. Having spent the last 6+ years neck deep in SaaS companies and their metrics, it is something that I am constantly looking…SaaS5 min readSaaS5 min read
