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 18,000 others receiving these blog posts by email.

How Much Money Should I Raise for My Startup?

How much should a founder raise for their startup? I imagine almost every founder contemplating a fundraising round ponders this question. There are many different paths to developing an answer. The right answer that every startup founder has told me is as much capital as possible at the highest possible price. But what strategies exist to justify increasing the round size and consequently price? These are the three most common I've observed.

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The Software Startup Sectors Raising the Most Capital in 2017

Over the last seven years, software startup investing has changed quite a bit. In 2010, classic SaaS was booming, the benefits of a subscription model were finally becoming clear to the public markets and the mass-market. Since then, many other types of software businesses have been created in new categories like agriculture technology and robotics. Which of these markets are growing the fastest for investment dollars?

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The Biggest M&A Multiple in Software History

Cisco announced yesterday it would acquire AppDynamics for $3.7B. We've analyzed AppDynamic's growth and key metrics, because the business had filed its S-1 to go public. However, the management team and board changed plans and made history. By my estimate, AppDynamics is the fifth largest software acquisition in modern times. More astounding, the AppDynamics acquisition does set the absolute high water mark in one regard - acquisition multiple. It's a very promising predictor of the 2017 M&A environment.

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Is Machine Learning Overhyped?

For the nine years I've been a venture capitalist, there's always been a buzzword of the year. Solomo (social local mobile). Mobile-first. Realtime. Big data. 2016 was the year of machine learning. Is ML just another wave to crash and dissipate on the trough of disillusionment?

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One of the Greatest Entrepreneurial Stories Ever Told

Over the last few days, I've been reading Shoe Dog, Phil Knight's autobiographical tale describing the formation of Nike, and I think it might be one of the very best founding stories I've read. Easy to read, brimming with passion, full of harrowing business crises, the book is an inspiration to anyone who has a crazy idea and commits to persevering.

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Using Chat in Content Marketing - Observations Several Months In

I've been struggling with the right way to enable commenting on this blog for a long time. In 2013, I wrote a post called Letter to the Editor about my challenges with comments. Several months ago, I deployed a chat widget at the bottom off this page as an experiment. Here are my observations so far.

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The $100M ARR Customer

Most SaaS companies dream of attaining the $100M ARR mark. The very fastest attain the goal in 6-7 years. Last week, Workday halted trading to announce it had signed Walmart as a customer. Brian White, research analyst at Drexel Hamilton investment bank, estimated this one customer could generate $100M-$200M per year for Workday in recurring revenue - a single customer.

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What I Learned from Complete Burnout at Work

During my first few weeks at Google, I read through the internal resumes of my new colleagues, which detailed their work and promotion paths. Google promoted people quickly. Some college graduates who had distinguished themselves had been promoted every quarter for more than a year, and were managers, senior managers, even directors. And I wanted the same type of trajectory.

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How Does Your Startup's Management Spend its Time?

Calendars contain one of the under-studied data sets within companies. How we spend our days, is of course, how we spend our lives, wrote Anne Dillard. How we spend our days at work determines what we and the company ultimately achieve.

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Which Round Will Be the Hardest to Raise in 2017?

The fundraising market is in flux. The data indicates that it is certainly reverting to the mean after two record years in 2014 and 2015. Late stage market dynamics are changing as hedge funds and mutual funds seek other areas to invest. In 2017, there will be a lot of comparison between the prices public bound companies fetch at IPO compared to the last round private valuations as the public window opens. Given all that change, which early round will be the hardest to raise for founders in 2017?

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