I'm a partner at Redpoint. I write daily, data-driven blog posts about key questions facing startups. I co-authored the book, Winning with Data. Join more than 20,000 others receiving these blog posts by email.

The Volatility of Multiples in the Public SaaS Market

We've seen quite a bit of volatility in the valuations of publicly traded software companies over the last 5 years. In 2014, the average software company traded at 7.7x forward revenues - the sum of projected revenues over the next 12 months. Two years later, that multiple dropped 57% to 3.3x forward. Today, we're exactly where we were in 2013, at 5.4x, which is coincidentally, is the average over this time period.

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The Limiting Factor of Voice and Dictation Adoption

Harry Stebbins published a podcast with David Beisel this week in which they discussed the importance of voice. David says, "Voice is the most natural user interface possible." I think the biggest challenge for voice is the skepticism and cynicism engendered by a decade or two of poor experiences. It's no longer the technology.

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Why Cash Conversion Cycle Matters for Your Startup

The cash conversion cycle is a key metric for startups, but one that often isn't talked about until a business hires a CFO. Once a business established product market fit, the cash conversion cycle is a key metric of a company's cash efficiency - how quickly a company can convert a dollar of investment into a dollar of cash flow.

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When, If Ever, Should Profitable Bootstrapped Startups Raise Capital?

Would you compare a bootstrapped SaaS company to a seeded company? At what point does the bootstrapped company have to raise if it's profitable, if ever? One founder asked me this question recently.

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Three Big Ideas on Technology Innovation Cycles

Invest Like the Best is one of my favorite podcasts. Hosted by Patrick O'Shaugnessy, Invest Like the Best profiles investors from many different disciplines. Recently, New York seed investor Jerry Neumann spoke on the show and talked about three key ideas on the technology innovation cycle.

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How to Decide When To Move Upmarket

At some point in the life of most SaaS companies, the business will be faced with the question, when should we move up market? The strategic question might be catalyzed by increasing cost of customer acquisition in the core SMB segment. Alternatively, a surge of large customers paying for the product might trigger the question. Or account executives might raise it. Whatever the reason, this is a key strategic question.

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Labor Arbitrage Comes to Silicon Valley

Last week, I wrote about the decline of investments in San Francisco startups. On Hacker News, this post engendered a lengthy conversation on the challenges facing founders and start-up employees in San Francisco. In short, the cost of living in San Francisco has reached untenable and unacceptable heights for many.

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How Developed is Global Venture Capital Market?

Just where is the US venture market relative to the rest of the world? After most US analyses I publish, a few founders in other geographies ask questions about their own. These inquiries made me wonder, how has the global market evolved?

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The Quickest Way to Estimate How Much Your Startup Needs to Raise

Tell me three numbers and I can estimate the amount of capital your startup will need to raise. Which figures are those? The startups' revenue target, the average revenue per customer and the average cost of customer acquisition.

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Self Service Data

During every person's working life, there comes a time when you have a question that could be answered by having access to the right data. Unfortunately, the time and effort required to find that data, package it the right way, and send it to an analytics or business intelligence tool present a formidable obstacle to answering the question. Two years ago, Redpoint partnered with Dremio to solve this problem. This morning, after an enormous amount of hard work from the team, the company has made its product publicly available.

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