The Inflationary Forces in Startupland

Over the last ten years, the 75th percentile post-money valuation of a cloud software or infrastructure company has grown 11% annually. In 2021, the post-money valuation has spiked 60% from $48.1m to $77.0m. While not as hyperbolic an inflation rate as copper or lumber, the price trajectory of early stage cloud startups does result from a similar supply demand/imbalance. And this isn’t the first time annual valuation deltas have touched this magnitude.

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The One Force that Will Govern How We Return to Work

This summer, startups will define how they return to work. In talking to founders and executives, I suspect the answer isn’t universal. But the force that will shape the decision is universal. That force is competition.

A startup has three main activities: (1) recruit a team to (2) build a product and (3) sell and service the product. Competition influences each of those functions.

Recruitment. Most people in Starupland spend more time looking for a parking space than for a job. The market is that competitive. To differentiate, employers find new ways of enticing the best people to come work for them.

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Never Raising, Always Raising

Startups used to raise once every 18 months. Today, we joke in Startupland that a startup is never raising and always raising. The implication is the most sought after companies often receive offers, whether they are in market raising capital or not.

Take a moment to think through that statement with me. Venture capitalists and boards used to value a company every 18 months. Then, every 12 months. Now every 6 months or every 3 months some startups receive termsheets valuing their business. We, as an industry, are marking-to-market much more frequently than we used to.

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How to Cut a Path through the Jungle of Regulatory Compliance

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Data privacy has become a skill startups must master as they scale. As they grow, startups often collect increasing volumes of data. With great power comes great responsibility. Regulatory regimes demand greater data security and integrity, and add complexity.

How should companies manage data privacy, especially regulations like GDPR and CCPA? To answer that question, Redpoint Office Hours will host Todd Smithline on Wednesday, April 21 at 9AM PT. Todd is managing prinicipal of Smithline, PC, a San Francisco law firm focusing on technology transactions, product legal review, and open source advisory work. He has taught the video game law class at UC Berkeley School of Law since 2021.

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Covid's Impact on Software Sales Efficiency

More than a year after Covid washed over the software ecosystem and the tide ebbs, it’s revealing the impacts on fundamental metrics of public software companies. Sales efficiency is one of those key metrics. Covid altered the way salespeople and marketers engaged their target markets. Travel collapsed, virtual events blossomed, handshakes became Zoom namastes. How did sales efficiency evolve?

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Would You Work for This Person?

Would you work for this person?

It’s a simple question. It’s one I often ask in reference calls on founding teams. During one of those calls, when I should have been paying attention to the answer, I posed my self a similar question. What is it about a person that would make me leap to work for them?

Intellect, ethics, ambition, conviviality, mastery, ethusiasm come to mind. But, those are subordinate characteristics. What’s the one thing?

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The Identity Crisis Facing Open Source Companies in the Cloud

Open source software marries the decentralized community of the Internet with the ambition to build great things. Databases, application servers, streaming technologies, application deployment, and container management - many modern tools were born open source. But the clouds are rolling in for open source companies (pun intended). Today, open source software faces an identity crisis: what does it mean to be an open source company in the cloud?

Imagine you’ve co-authored a massively successful open source project and you’re on the cusp of commercializing it. You face a critical decision. This decision will impact the business for the next 24 months and beyond. It will determine your price point, your roadmap, your hiring plan, your revenue, and consequently your fundraising prospects. The decision reversible, but not without pain and difficulty, and likely 3 to 4 quarters of work. What is that decision?

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UIPath S-1 Analysis: How 7 Key Metrics Stack Up

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.

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The Importance of Building & Maintaining Great Developer Documentation

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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.

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How Selling Has Changed Post-COVID, and How it Will Change Again Afterwards

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.

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