Stubborn Visionaries & Pigheaded Fools

How to make decisions faster, with less guilt. And less credit.

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You’re a company when…

My hope is that you’ll point up to that sign five years from now and explain to the children in your back seat that it’s there because of you, not just because “I was there,” but because you actually helped create it, one customer at a time, whether you thrilled them with customer service so deeply that they convinced a friend to sign up too, or helped them find us through the fog of “web hosting” propaganda, or helped them decide whether we’re the right partner for their business, or got them excited and saved them hours of drudgery through platform features, or helped all of us run the company smarter through finance and metrics, or made our office a lovely place to come to, or ensured that everyone we hire shares our values, or if you’re the silent hero who put out fires at 3:15am while everyone else slumbered in bliss.

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In its emptiness, there is the function of a startup

Thirty spokes join in one hub
In its emptiness, there is the function of a vehicle

Mix clay to create a container
In its emptiness, there is the function of a container

Cut open doors and windows to create a room
In its emptiness, there is the function of a room

Therefore, that which exists is used to create benefit
That which is empty is used to create functionality

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The only way to guarantee startup success

“Backstage, after their amazing performance, I chatted with [lead singer] Dave Gahan as he cried from pure happiness. He told me that the tears were because he didn’t know if the group could ever pull off anything this great again and for him it was the most emotional concert of his career.”

But what does it mean for you or me, that reaching the pinnacle of success is not only strikingly fleeting, but also sad? That tears of joy transmute immediately to tears of sadness, because reaching the peak means by definition your next steps must be downhill?

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No, *I’ll* tell you the answer!

When are you going to stop, take a breath, think quietly, shut out the cacophony of expectations and press releases and chest-thumping and biased storytelling, and decide what’s right for you? And then, harder still, can you be comfortable and confident in your choice?

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Why startup biz dev deals almost never get done

As the founder of WP Engine, I get a few emails a week from startups wanting to “do a deal” with us. So far, almost zero of them have resulted in an actual deal.

Here’s the problem, and how you can change your approach to business development so that it has a chance of succeeding.

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The public invisibility of running mid-stage successful companies

So says Keith Rabois, and the Internet generally: “I don’t know of a single successful CEO or entrepreneur who blogs regularly.”

If true, why?

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Smart Bear Live 8: Edwin from

Listen to this episode if you want to hear about a founder who has a product and users and paying customers … and is trying to figure out how to take his company to the next level and grow faster.

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Come visit @asmartbear and the @wpengine gang at SxSW in our new office space!

If you’re in Austin for SxSW, come say hello between 10:00 and 2:00 on Saturday, March 8. We’ll have an open lounge with food and coffee at our World Headquarters.

It’s an easy 5 blocks from the convention center, so there’s no reason not to hang out with us for a while, an oasis amidst the craziness.

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Raising money & selling companies at the end of the year

People say the end of the year is a terrible time to raise money or sell a company, because “everyone’s only thinking about the holidays” and “people with money are away skiing in Aspen.”

Except, my previous company Smart Bear was sold on Dec 20, 2007. And we completed our Series C round here at WP Engine on Dec 23, 2013. And no fewer then three other companies I was previously an investor in also raised a round that closed in December of 2013.

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Visualizing the Interactions Between CAC, Churn and LTV

You may have seen these metrics defined before, but this is the best visualization of their effect that I’ve ever seen.

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LARGE x RARE == DIFFERENT: Why scaling companies is harder than it looks

Scale causes rare events to become regular. Things happen with 2000 servers that you literally never once saw with 50 servers, and things which used to happen once in a blue moon, where a shrug and a manual reboot every six months was in fact an appropriate “process,” now happen every week, or even every day.

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More money if you do, more money if you don’t

A business always takes more money than you expect, even when you take this fact into account.

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