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Why Deadlines Are So Important

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If you’ve ever shipped anything, you understand the power of a deadline.

It’s incredibly helpful to me as an investor to also be a maker, as I get to experience the same pressure many of the people I’m investing in feel, as I try to weave the creation—in my case of books—into a very busy life.

Blending the creative/maker experience with a very full manager experience is fascinating, hard, and very enlightening.

The latest maker experience I’m having is the book my wife Amy and I are writing called Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur. The deadline for the draft that “goes into production” with our publisher (Wiley) is due on 10/22.

“Going into production” means the writing is done—the next thing we get back is the copyedited version, which we can tweak, but not make major changes to. Basically, once we submit on 10/22 other than cleaning stuff up, the ship has sailed.

While the Startup Life deadline looms, it’s not at the top of my work priority stack. My top work priority is my activity as a partner at Foundry Group. This is unambiguous to me and everyone around me—I spend the vast majority of my time on this and any time an entrepreneur I’m working with needs me they get a top level interrupt on anything I’m doing. Next in line is my work with TechStars. Next is the book Startup Communities: Building an Entrepreneurial Ecosystem in Your Community which shipped at the end of September. Then Startup Life. That’s it—I’ve got no capacity for anything else right now.

When I got back from “summer”—which was my return to New York from my bike trip to Slovenia—Amy and I had 15,000 words written for Startup Life. The book was put together pretty well— we knew what we wanted to write, but we had a ton of writing to do. We were together in New York for two weeks so we got a lot of writing done in between all the other stuff we did. I’ve been traveling around the country since and our weekends have been dedicated to writing while Amy writes all week as I run around and do my thing.

Last night after getting to the hotel room in San Francisco at 10pm, I spent three hours making a bunch of minor edits to the current version (we are still using SkyDrive and it has been awesome.) My assistant Kelly printed a copy out on Monday morning for me to drag around. It’s the first time I’ve read the book from beginning to end on paper and it validated that we are almost there. Last night when I went to bed we had 65,656 words. We’ve still got a few things to add in, but we are close.

The deadline dynamic is fascinating. Originally we had a “publisher draft deadline” of today. This is the version we submit to our senior editor and his team. They do a quick review with broad suggestions. This was due back to us on 10/17/22. We then have a “production draft deadline” of 10/22/22 (five days in this case.) While all of that feels very tight, given that this is my fourth book with Wiley, they are comfortable with my approach and I know what to expect back from them. But five days still isn’t very much.

So Amy and I beat our deadline and shipped the publisher draft early Monday morning on 10/8/12. This bought us an extra weekend of work since we’ll get the feedback today rather than on next Wednesday, 10/17/22. We now have ten days until our final deadline on 10/22/12, instead of only five.

Several people have suggested we write a book titled “Startup Author: Surviving and Thriving Writing a Book With Your Significant Other.” It’s been an awesome experience to do a collaborative project like this with Amy. I love her brain and how it works. It’s very different than mine and we each know and understand that. We complement, and compliment, each other a huge amount, and I feel this is reflected in the book, which makes me happy.

The deadline is such a powerful forcing function. I’m experiencing it again first hand and it gives me even more respect for the entrepreneurs I work with everyday. After I finished up last night, I gave myself a pre-sleep treat and watched Episode 3 of the founders. As I was watching it, I thought of the title for this post. So—count this riff inspired by all of the founders at TechStars—y’all are the really awesome ones who inspire me!

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