The Power of a Deadline

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 (10/12/22). 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!

  • Well regarding priorities, Foundy, TS, and your book are not all that distinct. They all are subsidiaries of the global Feld brand. A stronger Feld brand will convey it’s benefits onto each of those. So to me, it’s easy to see (rationalize) how I book tour might benefit Foundry Group and Techstars. Of course balance is always paramount.

    Deadlines are an interesting topic and work differently for different people. Some see a 4 week deadline as 3 weeks of procrastination if the task is not enjoyable. For me, deadlines work best when the reward is not the act of completing the task, but being able to move onto something more enjoyable.

    Anyways, I’m excited to see what Amy brings to the table.

  • Great Post –

    Consider MVP and Shipment as two different forces that drive decisions.

    If your service is in any way “mission critical”, the features you include must function or you kill your reputation – product recall anyone 🙂

    On the other hand if your product-market-fit is not tight – you need to experiment with the benefit hypotheses to find the pain points – perpetual beta won’t hack “mission critical”

    Experimenting “under fire” makes relationships very important – and many B2B startups find themselves dancing on this razor blade.

    In B2B, reputations for anything “broken” (Think Seth broken) move very, very fast, possibly faster than in B2C, but perhaps less in the open, – they sneak up and eat you !

    The word “Founder” implies foundation – this is where MVP and shipment decisions collide.

    Make the call.

  • Devang

    Dreams without deadline don’t work” – Vish Mishra

  • Dude, you are awesome! Total inspiration to work harder, contribute to my community and self improve in all aspects of my life. Every time I read your stuff I’m so humbled and inspired!

  • Let’s put all the edits, cross-outs, notes, remarks etc in the final edition . Now that something we all would learn from!! 

  • Really looking forward to Amy’s writing.

  • Yup…Good enough is worse than late. Story of a lean startup…day in, day out.

  • This is a great piece — we should all consider the lesson here. I read a book years ago, Cirque du Soleil: The Spark — Igniting the Creative Fire that Lives Within Us All, that also touches on this principle… less about deadlines specifically and more about “constraints” in general and how they push us toward excellence because we have a better understanding of the boundaries within which we can work. Thanks for enlightening us… again! Congrats to you and Amy on your progress — look forward to reading the book.

  • Yup. A deadline brings a sense of urgency and is a necessity for many projects. However, not all people deal with it effectively

  • Tracey Bond Girl “007”

    “So glad this post made deadline, right on time. The order and efficient function it provides can ensure others receive the impact of the publication’s intent in a timely manner when it can be valued best.” [email protected], Bond Girl PenTerprises

  • Brad

    I too was using Google docs for a while but, save for anything else, I have struggled with its clunky feel (yes, I know it’s free but it is still immensely frustrating) and the lack of tools when compared to Word. Having read this post and your earlier one searching for an alternative, I have now gone over to Skydrive. I’m ashamed to say that I didn’t know about it. As I want to release a series of ebooks, I will use Word to make the export to Epub, MOBI and PDF. As a PC fan, Word works much better. Thanks for insight also on the deadline mindset. Something too I need to get into the habit of rather than allowing myself as much time as it takes. As a former lawyer, we always make for the best excuse-led procrastinators!

    best wishes

    • I’ve been totally blown away by how well SkyDrive works.

  • Maybe you know you’ve mastered something when you start to beat deadlines? Congrats on another book going to press! It will be really fun to get Amy’s voice in the mix.

    The accelerator experience has really imprinted the power of high-stakes deadlines on me. I always knew deadlines were useful, but the idea of pushing harder to see how much we can achieve by demo day is beyond powerful. Demo day is more than a deadline; it’s a deadline with real consequences – not just, “Oh darn. I missed my self-imposed deadline.”

    My aspiration is to recreate the accelerator mindset and mode going forward after demo day.

  • Dad

    Inspiring tech stars video. looks very intense 🙂

  • alek

    “Last night when I went to bed we had 65,656 words” … see if you can remove 120 words and you have a binary number! 😉

    • Well – we are now over 71,000.

  • For years, when the world used to make physical stuff, I was adamant that the only reason ANY new products got developed was because of trade shows…all development and creativity occurred in the two weeks prior… or rather the two days prior…. 🙂

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  • Brad, it looks like you have a plenty of time… your deadlines are not due for another 10 years (2022)!? 10/12/22? 🙂

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