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.

Sushi, passion, and entrepreneurship

Passion is not something you follow. It’s something that will follow you as you put in the hard work to become valuable to the world. Follow a Career Passion? Let It Follow You

In his book “So Good They Can’t Ignore You”, Cal Newport, a college classmate, champions the idea that passion lags work, instead of passion inspiring work. It’s the same philosophy embraced by sushi master Jiro, in the documentary “Jiro Dreams of Sushi.” Jiro should focusses on mastering a practice, making sushi.

Passion ...

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A six-step framework to make strategic decisions

Any number of challenges can arise during a startup’s initial years. Some of these changes could be major and may require rethinking strategy. Competitors enter your target market. New products are released into your market which undercut yours. Customer acquisition costs rise dramatically.

If faced with these questions, it’s hard to know where to begin or how to structure an analysis to reach an answer.

McKinsey uses a 6 step process to frame the process of answering these strategic questions which is profiled in this month’s Harvard ...

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Should founders join incubators?

Yesterday, I spoke at Columbia Business School. We had a conversation about the role of incubators and accelerators (or the moniker of your choice) within the startup ecosystem.

Given the volume of first time entrepreneurs and the broad growth of interest in entrepreneurship, I think these programs are invaluable. To entrepreneurs, these programs offer up to seven value propositions, listed in order of importance, as I see it.

  1. Education - Examples include General Assembly runs a substantial education program and YCombinator operates Startup School ...

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The startup love affair

Every investment requires a leap of faith, an emotional act that’s not pure reason, and that’s got to carry you through in the inevitable many months, sometimes years, of horrific bad stuff that comes with the company. And you’ve got to have that energy, that sustaining belief to carry you through, because if you don’t, then you regret having done it. So when I have regret, it’s when I didn’t have that, and I’d logically talked myself into [the investment] and checked the boxes. So it was really helpful ...

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The Heyday of SaaS - quick observations from Dreamforce

  1. We are in the heyday of SaaS. The conference spanned 20+ buildings, served 60,000+ attendees and was sponsored by more than 300 vendors. Free food everywhere. Skullcandy wireless headphone giveaways. DJs in every corner. Four square play areas on fake grass outside. It is one huge party.
  2. Benioff delivered a tremendous keynote. I wish I could speak in public with his confidence, control and passion.
  3. Dreamforce created the perception that Salesforce is at the center of a huge ecosystem of their own creation, which inspires confidence in ...

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A startup’s transition from product development to growth

At a recent meeting, David Barrett, one of the founders of Expensify, drew this diagram when explaining his company’s structure. He has overlaid the core teams of a company with a conversion funnel. It’s brilliantly simple.

Screen Shot 2012-09-20 at 7.08.30 AM.png

As every SaaS startup transitions from development to growth, the company must supplement the engineering and product capability with sales, marketing and account management. This diagram is the simplest way to show how they work together harmoniously at a strategic level.

Marketing builds a ...

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Data isn’t a business model - it’s much more important

The throwaway line in pitches these days is “we’ll sell our data.” Most of the time, this notion is wrong.

Data is the most valuable outcome of building a successful product. It’s the insight, the secret, the keys to the kingdom. Don’t sell the keys to the kingdom.

Big-Data-disguises-digital-doubts-UU1M91QI-x-large.jpeg

Data provides economies of scale and insights used to develop huge barriers to entry and it should be kept within an organization. Internal data use is the path to building a huge business.

For example, ...

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The Secret to SMB SaaS Distribution

SMB SaaS companies cannot afford to pay for distribution. At 2 to 4% conversion to paid rates and $5 to $10 monthly subscription fees, the breakeven CPC for these products on search is $0.40. The average Google click costs three times this and the iOS average cost-per-install is more than twice as expensive.

The most successful SMB SaaS companies (Zendesk, Expensify, Square) build communities to drive distribution. Those communities reinforce and build a brand. And the brand drives subsequent organic distribution.

Expensify and ZenDesk are two ...

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Must startup founders be charismatic?

Culturally, we tend to associate leadership with extroversion and attach less importance to judgment, vision and mettle. We prize leaders who are eager talkers over those who have something to say.

Must great leaders be gregarious?

Susan Cain wrote an OpEd this weekend in the Times containing the quote above. In Silicon Valley, the culture seems very much to embrace the idea of introverted leadership. One might even say the two kinds of leaders live in harmony.

On one hand, there are the garrulous Jobs, ...

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Mechanizing business development with social media

Last year, I set a goal of adding 100 followers each week starting at 2000. I crossed the 3500 follower mark on Twitter this week. I’ve fallen a bit behind that goal but I have a wonderful group of people who actively engage with me on Twitter who are interested in the same things I am.

As I’ve been cultivating this audience and community, I kept asking myself a question: who are most of these followers? Who retweets me? Who should I meet in person and build a deeper relationship ...

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