You probably won’t be a success from day 1. Most founders struggle and may even come close to failure (more than once). The good news: there are plenty of examples of companies that had setbacks along the way, but were still a great success. Docusign is one such success story.

Docusign went public in 2018 with $381mm of total revenue and 350,000 total customers. While Docusign is a success, it wasn’t a straight line. Below is a graphic taken from Docusign’s public filings which shows what I’m talking about.

A few things stand out.

Docusign muddled along for years. Founded…


Are startups a young man’s/woman’s game? No. We have made 24 investments of which 5 of them have CEO’s who are over 45 with families. That said, being young is definitely an advantage:

You don’t need much money. At the early stage of a startup you’re probably on a low or even no salary. It helps if your personal expenses are low. Overhead like kids, a mortgage, a stay at home spouse, etc, will severely limit how long you can go without a salary.

You have more time. You can’t be successful in your personal life without committing significant time…


The most important metrics for B2C companies are customer acquisition cost or “CAC” and life time-value or “LTV”. The first measures the cost of acquiring the customer while the second measures the profits of the customer over it’s life with you. We found only 5 public companies that disclose real detail about the metrics, but the data was valuable to understand how your CAC and LTV should trend.

Chewy’s LTV to CAC is 2.4x for a 3 year old cohort. Chewy doesn’t disclose CAC or LTV individually, but does disclose the ratio. The chart below shows the 2015 and 2014…


If you’re depending on your customer base to add users as a way to drive upsells, you’re doing it wrong. Here’s why:

Charge based on value, not seats. You shouldn’t be charging the customer based on the number of seats/users they have on your platform. You should be charging based on the value and ROI you’re generating for the customer, materially discounted of course so they can realize that value. Then, you should allow the customer to onboard as many users as possible onto your platform. This creates strong evangelism at the client and prevents you from losing the customer…


In software, there are a few ways to measure the health of the customer base and stickiness of the product. Zuora does a nice job of showing four measures of customer health in their S1.

Processed Transaction Volume

Zuora’s first measure of the overall health of the business is processed transaction volume. According to their S1, “Our customers’ increasing usage of our solution is evidenced by the growing amount of transaction volume processed by our customers on our platform. For the quarter ended January 31, 2018, our customers processed nearly $7.0 billion in invoice volume through Zuora Billing.” …


There are countless examples of ‘first to market’ not being a sustainable competitive advantage. Comparing the 2018 public offering of Spotify to Pandora’s original IPO in 2011 is a major example. Below are some excerpts from Pandora’s S1 (official IPO document filed with the SEC) that show its dominance at the time:

Pandora is the leader in internet radio in the United States…. In January 2011, we had over 80 million registered users and we added a new registered user every second on average. We have more than a 50% share of internet radio listening time among the top 20…


Bill.com, SumoLogic, and Confluent are public SaaS companies with excellent customer performance. In their prospectus’, each of these companies was generous enough to share beautiful contribution margin data. Specifically, Bill.com shows the contribution margin of customers acquired in 2017, and SumoLogic and Confluent do it for customers acquired in 2018. It’s a very nice illustration of the first three years of a SaaS customer in a healthy SaaS business. The charts are below. Commentary follows.


I read Trish Bertuzzi’s book ‘The Sales Development Playbook’ and it was by far one of the best sales books I’ve read in a while. The book focuses heavily on building pipeline with SDR teams. This is the second post of a few I’m going to share about this book: there was so much good information that putting it all in one post would be too long. Below are some of the excerpts I found to be very insightful.

Reps are giving up too quickly. Studies have found that it takes between six and ten attempts (including at least four…


Trish Bertuzzi’s book ‘The Sales Development Playbook’ is by far one of the best sales books I’ve read in a while. The book focuses heavily on building pipeline with SDR teams. This is the first post of a few I’m going to share about this book: there was so much good information that putting it all in one post would be too long. Below are some of the excerpts I found to be very insightful, through page 55 only.

Intro meetings and Qualified Opps. “There are two main models in play: setting introductory meetings and generating qualified opportunities.” With introductory…


One the most important metrics in SaaS is net dollar retention (“NDR”). It tells you what percent of revenue from current customers you retained from the prior year, after accounting for upgrades, downgrades, and churn. For SaaS businesses with annual or multi-year contracts, formulaically it’s beginning of period revenue + upgrades — downgrades — churn all divided by beginning of period revenue.

Similarly, you can also calculate NDR by starting with the ARR from all subscription customers as of 12 months prior to the current month (Prior Period ARR). Then calculate the ARR from these same subscription customers as of…

Sammy Abdullah

co-founder at Blossom Street Ventures. Email me at sammy@blossomstreetventures.com

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