Fresh Insights

Analyses, Musings & Observations

Strategic investors are NOT important

Entrepreneurs are always looking for “Strategic Investors” — corporate VC such as Intel, Verizon, SAP, Microsoft, Salesforce, Cisco, InQTel, etc. The view is that these investors provide not only capital, but also guidance on the product roadmap, engineering/dev resources, critical introductions, and they’re often customers themselves. Demand for strategic investors lead us to ask: how important are…
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Learnings from a SaaS IPO – Expensify

Expensify is a software company that went public in 2021. Below are some of the highlights and learnings from their prospectus. What they do. “Expensify is a cloud-based expense management software platform that helps the smallest to the largest businesses simplify the way they manage money. Every day, people from all walks of life in…
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Learning from Yahoo’s mistakes

Nicholas Carlson wrote a fantastic book about Yahoo entitled “Marissa Mayer and The Fight to Save Yahoo.” Below I have paraphrased what I found to be valuable sections, verbatim; the full book is definitely worth the read. Allow employs to give feedback, anonymously. The questions were submitted during the week leading up to the FYI…
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$49k is the median ACV

Average Contract Value is an important metric in SaaS, but don’t obsess over it as retention, cash efficiency, and growth should come first (in that order). The last 73 SaaS companies to IPO had a modest median ACV of $49,263. A few observations: Bigger software companies have smaller ACV’s. To do the analysis, we looked…
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12 commandments of customer success

We’ve had the good fortune of learning from and investing in SaaS businesses with excellent customer retention and upsells. Below are some of the key learnings we’ve gathered over time. The Customer Success Team is not the only group in charge of customer success. Preventing churn is everybody’s job, so your engineers should talk to…
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What big funds look for in a CEO

Recently, we got a hold of an investor letter from one of New York’s finest late stage venture funds. The letter shared insights into what the fund looks for in a management team, which resonated with us. Below we share these points, verbatim. We like CEOs that are patient with us and believe that all…
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First to market often loses

A lot of companies that feel like they must be ‘first to market’. There is a belief that if you’re not the first and biggest in a market right away, you won’t be successful. If anything, history shows that the first mover and land grabbers always loses to the ‘first innovator’. Consider the following: -Apple…
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Pulling off the acquihire

We just watched a company go through a very intense, distressed M&A process that fell apart in the final hour.  It was an acqui-hire which has its own nuances relative to traditional M&A.  Below are some tips to pulling off your own acqui-hire should it come to that.   Protect your team from getting poached. …
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Non-recurring revenue matters

Everyone loves recurring revenue and rightly so: it’s far more valuable than one-time revenue to VC and acquirers. But don’t forsake one-time revenue. Some of the best SaaS businesses in the world generate a lot of services/one-time revenue as it’s a valuable source of cash and makes the product stickier. The list below shows the…
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Learnings from a SaaS IPO – Backblaze

BackBlaze is a software company that went public in 2021. Below are some of the highlights and learnings from their prospectus. What they do. “We are a leading storage cloud platform, providing businesses and consumers cloud services to store, use, and protect their data in an easy and affordable manner. By substantially reducing the complexity…
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