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UIPath, leaders in the Robotic Process Automation (RPA) category, filed their S-1 last week, revealing an impressive business. Founded in 2005 in Bucharest, Romania, by Daniel Dines and Marius Tirca, the company now operates more than 60 offices housing nearly 3000 employees.

UIPath offers software to build robots, programs that automate repetitive work. Some examples include streamlining customer onboarding. Robots read pdfs that customers provide and input that data into other computer systems. Customer support teams might use RPA robots to read the contents of an email, find an order number, look up the order, and present the support agent with some key data.

Developer tools and business-to-developer companies are among some of our favorite category of startup. We’ve had the privilege to partner with many of the leaders like Stripe, Twilio, Hashicorp, LaunchDarkly, SourceGraph, and Heroku, among many others.

Developer documentation is one of the differentiators in developer community building efforts. If you’re an engineer, and you hear about an interesting project, the first place you’ll land is the documentation. Guides that are easy to follow, have clear examples, and guide an engineer through a smooth experience grease the user engagement and acquisition funnel.

Recently, Jim Benton joined us for Redpoint Office Hours to share insights from his vantage point as CEO of Chorus.ai on how sales has changed during the COVID era.

Jim shared many data points that opened up my eyes to some of the challenges and the opportunities before modern sales professionals. I took away three key ideas, though we covered much more in the session.

I’ve been following many public market investors on Twitter over the past few weeks to understand how they view the vacillation of the public markets. One of the tweets linked to a speech Stanley Druckenmiller gave in 2015 about Black Wednesday.

At the time, Druckenmiller worked for George Soros at a hedge fund.

“George, I’m going to sell $5.5 billion worth of British pounds tonight and buy deutsche marks. Here’s why I’m going to do it, that means we’ll have 100% of the fund in this one trade”.

A 20% delta in net dollar retention (NDR) may not seem like much, just a trifle, but make no mistake, it’s massive. In preparing for a presentation at next week’s Saastr Build conference, I reviewed this S-1 analysis for DataDog that I had published a few years ago.

It shows the difference in the net dollar retention across three competitors in the same space, Application Performance Monitoring: DataDog, New Relic, and AppDynamics.

About a year ago, I wrote a post on the hub and spoke data model. The idea is that in the future SaaS applications would be built on a single database, instead of each SaaS application writing to its own proprietary database.

I was wrong about the catalyst for this hub-and-spoke model. I thought it would be cloud-prem and customers driving SaaS products to use a single database. Instead, the SaaS ecosystem and the data ecosystem are moving in this direction on their own.

If you asked 5 people in Startupland to define the role of a COO, you would receive 10 different explanations. I have three myself. What does a modern COO do?

The role of a COO has evolved over the past decade or so because of broader changes within the ecosystem which has created some confusion what what precisely should a COO do. Recently, Redpoint Office Hours welcomed Allison Pickens to clarify the COO role and when startups should consider recruiting one.

So you’re looking to start a company. What do you call it? Once you’ve figured that out, which domain suffix do you choose? .com, .net, .biz, .monster, .duck, .theworldisyouroyster? Given the explosion in domain suffix permutations I wondered if startups’ behavior had changed over the last decade.

In fact, it has changed significantly as the chart above shows. Click to enlarge the image.

On Wednesday, March 3rd at 10:00 AM PT, Redpoint Office Hours will host Jim Benton, CEO of Chorus.ai, a leader in conversational intelligence. As Co-Founder of ClearSlide and later as CEO of Apollo, Jim helped create the Sales Engagement category. From Evite to AdBrite to ClearSlide, Jim has expanded new categories and scaled revenue teams from zero to tens of millions in SaaS revenue.

If I gave you $1000 to invest, and five investment options how would you decide? What if you were the CEO of a startup, and a VC invested $10m, and each of your five VPs had different project ideas?

This is the question John Kelly, researcher at Bell Labs, sought to answer.

A contemporary of Claude Shannon, Kelly intertwined Shannon’s information theory with probability to develop an idea of his own: the Kelly criterion. His theory would translate into tremendous investing prowess and lead him to one of the best long term track records of all time at Princeton-Newport, a hedge fund he managed to 15% net IRR compared to the S&P at 8%.