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The debate about partnering with Snowflake went back and forth during the investment committee meeting. It was March 2014. My partners, Satish and John, had met the company and were proposing to lead the Series B. The company was about two years away from launch and heading straight into a dance with elephants.

Google and Amazon both offered competing products and were already in market. Here was a plucky group of founders with deep technical expertise seeking to take on the incumbents with a novel architecture. And that was the bet the deal team advocated: Snowflake’s superior architecture will triumph in the end when users begin to query petabytes of data.

Have you ever sold a product while working at the market leader? How about from the market challenger? If you’ve done both, you know how different the role of a salesperson can be in each of these businesses. having them both, I can tell you that though the jobs have very similar titles, the work is quite different.

The market leader benefits from the strength of its brand. Buyers compare other products to the leader. For account executives, everything is easier. The brand’s strength eases prospecting work. Internal champions prefer recommending the leader to their superiors because it’s easier, increasing close rates. And if that implementation fails, there is lesser downside risk. Salespeople leverage the trust the brand has created.

Net Dollar Retention is one of the most important metrics is a SaaS business. It measures the value of a cohort of customers over time including expansion, cross-sell, and churn (loss of revenue). But how do you measure NDR?

Imagine this is your company’s data. The first column is the cohort month for each cohort in a year. The second column is the revenue of this cohort in their first month. The second colum is a random number between -20 and +20 that is the NDR for that cohort. The last column is the ending revenue of that cohort.

When we announced our investment in and partnership with Mattermost about a year ago, I wrote about a new architecture for SaaS. I’m starting to see that architecture more and more, but with a twist. The idea behind the new architecture is split a SaaS app into code and the data. The SaaS company writes, updates, and maintains the code. And the customer manages the data. Typically, the data resides in the customer’s cloud account.

Nathan Heller published an article called Is Venture Capital Worth the Risk? in the New Yorker. It’s a well-researched critique of the venture industry. The key question he poses is: has the industry become so large that it needs to be disrupted?

It’s a thought provoking question and a good opportunity to ask for feedback on how we can imrove. If you have ideas for how to improve venture capital for founders, please tweet me or send me an email with the link above. I’d love to hear them.

Today, the world’s most valuable brand is Apple. Forbes estimates Apple’s brand is worth $205B. Why is Apple’s brand worth so much? It’s the trust the brand inspires in consumers.

Apple customers know Apple the company. They understand the product philososphy, the history, the quality of typical Apple products, and the reputation for quality. A strong brand is the lagging indicator of having built trust. We won’t buy from people or companies we don’t trust.

Payback period is one of the best composite diagnostic metrics of product market fit. I’ve written before about the benefits of short payback periods. In short, startups with shorter payback periods require less capital and also grow more quickly. In 2020, what is an excellent payback period[1]?

Here is a group of publicly traded companies sorted by estimated payback period[2]. Zoom is at the top with a payback period of just over 3 months. DataDog, Slack, Crowdstrike, and Twilio round out the top 5 at 7 months or less.

At this year’s Saastr Annual conference, I’m excited to interview Nick Caldwell. Nick has an incredible background. He started the PowerBI team at Microsoft and grew it from a small number of people to more than 300. He left to become VP Engineering at Reddit and tripled the size of the engineering team to 150 people in 18 months. And then he joined Looker as Chief Product Officer.

In short, Nick has helped grow engineering and product teams from very small to very big three times. In preparing for the session, I’ve learnt a lot about Nick.

Go to market questions are some of the most common questions startups discuss in board meetings. This is especially true around the end of year because many companies develop their financial plans. To help startups understand how their go to market teams compare to peers, Redpoint has constructed a survey. You can find the survey here.

The survey will answer questions like:

• How does the sales team structure differ by stage? by target buyer? by price point?
• How do sales team compensate their account executives and their SDRs/BDRs?
• At what stage do startups hire VPs and C-level executives in each go to market role?

Last year, we published the results on the Free Trial/Freemium survey and it was a huge success. We received more than 600 responses and the data was tremendously insightful. We hope to exceed those numbers this year.

We are 12 years into the longest bull market in US history and this bullishness has powered the venture market. Investors deployed $117 billion in 2019 up from $106 billion in 2018.. This market has grown 20% over the last five years. It’s been go, go, go for nearly a decade.

However, Q4 2019 saw meaningful dip from Q3, but it’s too early to say whether it’s an aberration, or the beginning of a longer-term trend.