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 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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The Decline of Investment in San Francisco Startups

Bloomberg published a post this weekend called San Francisco's VC Boom is Over. The article pointed to the seeming collapse in the amount of venture capital raised by San Francisco startups relative to other regions. The slowing of venture investment more broadly across the US serves as a backdrop to San Francisco's particularly strong correction. I was curious about the drivers of these trends, so I ran my own analysis.

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