Hi, I'm a partner at Redpoint. I invest in Series A and B SaaS companies. I write daily, data-driven blog posts about key questions facing startups. I co-authored the book, Winning with Data. Join more than 16,000 others receiving these blog posts by email. Subscribe.

The Great Unbundling of Email

Since it was first written in 1982, the Simple Mail Transfer Protocol, the mechanism for sending emails, has remained largely remained unchanged. Today SMTP delivers 70 trillion emails to 5B inboxes each year. Overwhelmed by tens of thousands of emails, most of us can sympathize with Nick Bilton, who said:There is no escape:Email is probably most invasive form of communication yet devised.

Read More...


How Much Should Your Startup Spend to Grow?

Several weeks ago, I wrote a post about the Optimal Contract Value for a SaaS company. I wondered whether startups serving enterprises might be more or less valuable than those serving small-to-medium businesses (SMBs). Interestingly, the data showed there was no optimal customer value to build a publicly traded SaaS company. Having written that post, I began to wonder about other differences between different types of SaaS companies. In particular, do SaaS startups serving SMBs spend more or less than their counterparts in the mid-market and enterprise? And which type of SaaS startup grows the fastest?

Read More...


The Optimal Seed Round Construction to Maximize Series A Success

Is it better to raise your startup's seed round from only angel investors, or is it better to include a VC or two? Several founders on the precipice of launching their seed fundraising processes have asked me this question. It's a very difficult one to answer hypothetically because there are many different variables to balance. For example, VCs may invest larger sums than angel investors. The imprimatur of a VC's investment in a company might help convince potential customers and recruits. But some might argue their money brings potential signaling risk.

Read More...


The Impact of VCs in Seed Rounds in Seven Charts

For the past several years, early stage VCs have entered the seed market with vigor. VC"s entry has resulted five different important trends in the past five years

Read More...


The Riskiest Investment a Startup Can Make

Marketing investments are unlike any other investment a startup. They are the least-tangible, least-measurable investments and that is why they are perceived as the riskiest investments.

Read More...


The Hidden Costs of the Switching Products in the Consumer Web

Michael Porter created the Five Forces Framework in 1979 in a landmark book called Competitive Strategy. One of those forces, the threat of substitutes has intrigued me for quite a while because in the world of the Internet, the prevailing wisdom on switching costs argues they are trivial on the web. After all, how difficult is it to change from Google search to Bing search? This is the question Google wrestled with during its search share battle in the mid 00s.

Read More...


Salesforce's Marketing Secret: The Fourth Marketing P

In his book Behind the Cloud: The Untold Story of How Salesforce went from Idea to Billion Dollar Company and Revolutionized an Industry, Marc Benioff shares the 111 plays he learned through Salesforce triumphant rise to the most valuable SaaS company in the world. Play 15 is my favorite from the book.

Read More...


The Common Characteristics of Successful Freemium Companies

Is there a common characteristic of successful freemium companies? Piotr asked this question earlier this week. This is the framework I've seen work well for freemium startups.

Read More...


The Impact of Varying Sales Hiring Strategies on SaaS Startups

What are the tradeoffs when considering different sales hiring plans and which is the right one for your startup? There are many different considerations in creating a sales hiring plan. Balancing them all can be tricky, but thinking through the trade-offs is important to scaling the business well.

Read More...


The Common Language of Great Teams

Last week, Redpoint held our annual Founder Day gathering. At the event, I listened to the stories of Felix Baumgartner's record breaking jump from 120,000 feet, heard about the astonishing comeback of the US America's Cup team and took part in a creativity workshop led by a Stanford Design School professor. In short, the event revolved around doubt.

Read More...


Index