I'm a partner at Redpoint. I invest in Series A and Series B SaaS companies. I write daily, data-driven blog posts about key questions facing startups including how to fund raise, startup benchmarks, management best practices and team building. I co-authored the book, Winning with Data. Join more than fifteen thousand others receiving these blog posts daily by email.


The Power of Open Source to Solve the Data Fragmentation Challenge

Most modern data architectures employ many different data stores and processing engines. Hadoop, Cassandra, HBase, Spark, Storm, Phoenix. Data analysts looking to unearth insights within these data stores must move data back and forth between different systems and different data formats. As the number of new open source projects continues to grow geometrically, this data fragmentation is likely to splinter further.

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Venture Debt for SaaS Startups

There are several forms of venture debt. Convertible notes are the most common, today. Most startups raise seed rounds using convertible notes. Startups that have substantial working capital requirements often employ lines of credit/revolvers. Last, many startups take out term loans. They borrow money for several years and repay it over time. Venture debt can supply additional capital for a startup to grow at a lower cost of capital than equity. And the difference can be material.

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The Other Payback Period that Matters in SaaS

When we discuss payback periods in SaaS, we implicitly mean customer payback periods. How much time does it take for us to recoup the capital outlay we invest in acquiring a new customer? But, there's a second and equally important payback period – the payback period on hiring a new account executive.

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How to Become Profitable Faster in SaaS

As the fundraising environment changes, some SaaS companies will look to reach cash flow break even on their existing reserves. Founders may reduce staff, particularly in recruiting or new projects that the company prefers not to finance. But there are three other ways to become profitable that limit reductions in force, enable the company to continue to grow with greater efficiency and increase the value of the company in the process.

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Mr. Market and the SaaS World

Mr. Market is a fictious character imagined by legendary investor Benjamin Graham in The Intelligent Investor]. Graham describes Mr. Market as emotional, irrational, moody - and is in the short run a voting machine, in the long run a weighing machine. It might sound like a children's story, but Warren Buffett lauded the book as the greatest book ever written on investing. So, has is halving of SaaS multiples the work of irrational Mr. Market or a change from the voting machine to a weighing machine?

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The 57% Drop in SaaS Valuations

What a difference a month makes. I wrote a post on January 10, 2016 called The Downward Pressure of Public Markets on Startup Valuations that depicted the slow decline of SaaS multiples in the public markets. Since then, multiples have compressed markedly.

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The Nature of Leverage in Fundraising Conversations Has Changed

Leverage. It's the key to negotiating. Classic negotiating books like Getting to Yes define the BATNA, the Best Alternative to Negotiated Agreement. If you were to walk away from a conversation, what's the next best choice? The BATNA singlehandedly creates leverage in negotiating.

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With Smart Software, Sell Ironman Not Robocop

When buying machine learning enabled software, it's easier to sell like Ironman than Robocop; a product that complements and augments the user's skills rather than a true replacement. As machine learning continues to become a key differentiator among SaaS products, a secular and positive trend, startups are learning how to sell the promise of the software better and better. These are some of the objections customers raise during those sales pitches.

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The 12 Things I Know About You

Here are the first three. You have a great need for other people to like and admire you. You have a tendency to be critical of yourself. You have a great deal of unused capacity which you have not turned to your advantage.

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Chained Probabilities in Startup Business Models

In 1983, Lorne Whitehead, a physicist from the University of British Columbia proved he could knock down the Empire State Building with 29 dominos. A domino can knock over an other domino one-and-a-half times its size. Whitehead's theory concretely demonstrates the power of a chain reaction. Like a series of dominos, a startup's success is a chain reaction.

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