The Monastic Startup

Last week at our Yesware board meeting, we talked about the idea of “the monastic startup.” This was a phrase that Matthew Bellows, Yesware’s CEO, came up with, and it characterizes the culture they are creating at Yesware. It embodies two concepts:

The monastic startup is a place where engineers do the best work of their lives. This place involves work with long stretches of uninterrupted time.

This idea sung to me. As I sit here in front of my 30″ monitor, working away in the peacefulness of my office in Boulder, surrounded by 10 of my favorite people (the gang I work with), listening to Lady Gaga, and connected to thousands of others via the computer in front of me, I realize that I long for more “monastic startup” time.

When I think about the culture of many of the companies we are an investor in, the definition of the monastic startup rings true. Oblong immediately comes to mind for me. Kwin Kramer, Oblong’s CEO, wrote an awesome guest post on TechCrunch over the weekend titled The Next, Next Thing. Oblong is one of the most monastic startups I’ve every encountered (using the definition above) – even Kwin and his partner John Underkoffler still spend long stretches of time writing code as they do the best work of their lives.

In my networked world (vs. hierarchical world) a monastic approach works amazingly well. I’ve started experimenting with more non-in person tools to increase the quality of communication across my network, while preserving a level of “monasticness.” The Yesware guys use HipChat for persistent chat. I’m looking for others – suggestions? I’m especially interested in things that work well across organization and communities.

If the phrase “monastic startup” rings true to you, what are the other characteristics that you’d expect to have in this environment? And what tools would you use?

  • I’ve called this ‘distracted focus’ for years – being so focused on a task or outcome that everything else is treated as a distraction, because it is.

  • I’m a really big fan of Yammer for inter company, non-in-person communications. I like it better than hipchat because the conversations are threaded – which means its easy to ignore one I’m not interested in. Also the groups are shown inline in one stream so I don’t have to check multiple “rooms” but can just watch the one feed.

    • I haven’t had experience with it “inter-company” (only “intra-company”). Can you invite me to your inter-company chat so I can see what it looks like?

  • One of the big ongoing debates for startups is open divided space.  There’s a ton of literature about programmers and “the flow” and how it takes a sizable amount of time for a programmer to rebound from an interruption.  You would think that there would be more startups trying out offices or at least cubes.

    • We had cubes at Wily (in the shitty office in Burlingame) + we’d just sorta shout questions + stuff to each other.  The close proximity made this possible.

      It also made it impossible to avoid the one coworker (a great friend, so I say this w/ healthy respect) who’d loudly squawk like a parrot in heat once or twice a day.  made me jump out of my chair first time I heard it.  He said he thought he had Tourette’s (undiagnosed).

    • Well… some monks take a vow of silence.  It wouldn’t matter if it were a cube or open space, if there was 1pm-4pm vow of silence in effect.  I thought 37signals do something like this… self imposed communication blackout.

      • Oooh – I like the vow of silence from 1pm – 4pm – that’s an inspired idea.

        • Communal wine making was my other monastic idea.   Could do a portfolio wine tasting event.  The Oblong Mezzanine Blanc had a great vintage year.  er… nvm.

      • We have a “no-meetings” policy every day until noon. Actually, we do a 15 minute company standup at 10am, but then no meetings until lunchtime. So everyone gets a morning of uninterrupted work time. Thanks for the great post, Brad!

    • Works both ways tho’.

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  • we use the basecamphq to-do feature,  you can have multiple to-do lists with multiple items each and threads of conversation under each item.  this way authors can add notes when they run into things such as bugs and recipients can review when they set aside time to do so, i.e., not an instant distraction.

  • You’re touching on something that I think it’s a silent bomb in our society. Big respect for the value of online networking (Facebook, Twitter, LinkedIn), but I can’t help and notice the toxic factor they also bring. Millions of teens lose their best years with chatter. These networks don’t control or guide the user on a good path, it’s up to the user. You can’t possibly achieve focus and concentration when you’re updating the world every few minutes or checking for news. A massive ADD factor has been created and this is costly. Angry Birds alone costs economy $1.5B/year or 1.2B hours lost/year. To compare, Wikipedia has counted about 100 million hours over its entire lifespan. Many of these users are switching to a virtual lifestyle but unfortunately they’ll have to die in the real world. Ask a preschooler nowadays if they want to go camping or sit on the grass and they quickly raise their eyes from their PlayStation and look at you as if you’re not ok.

    This translates to startups. A vast majority today are what I call mini-tech. Sure some get complex due to the nature of their scaling factor eventually (Twitter right?), but few entrepreneurs dare to start with ambitious and heavy tech. Probably 90% of the Math of this Planet does not make it into startups. Just look at how slow the world of robotics is moving and it should have benefitted well from the low barrier of entry provided by modern cheap hardware. There are lots of other areas that just don’t grow fast enough because they don’t have at core conditions that allow for long concentration and focus on problem solving. I have a feeling Elon Musk won’t have much competition (or enough help) soon.

  • I’ve found that a well tuned forum or two can keep a team communication together, quite passively.  Also more room for “off-topic” discussion as I can’t really clutter up basecamp for that.

    Additionally, having both a customer facing forum, and internal forum, keeps your staff right at-the-customer-level.  It’s much easier for staff to participate in customer discussions that way, vs logging into to some support layer, like uservoice or a ticket system.

  • Like the idea/concept, except generally women aren’t allowed in monasteries. 😉

    • In my monasteries, women are allowed.

  • And like all great monasteries, it’s vital we have our own ‘sanctuary’ – a place where we can just be..

  • +10 for listening to Lady Gaga.

    • We are all about Adele right now at the end of the day.

  • How does this jive with the “law of diminishing returns” that Tony Schwartz from Harvard talks about –  I was just talking with someone about this at lunch today – I was saying how after a few hours by myself I need to have human interaction – now my personality requires something like that (I used to be a programmer a long time ago, but don’t do it much anymore).  I personally cringe at thinking about a monastic approach if it means no other human interaction – it’s interaction that fosters creativity, new ideas, and staying out of a rut, no?

    • I think both modes are important to creativity. And – in different ratios for different people.

  • James Mitchell

    I don’t think this is very much different than “What is necessary for someone to get into and keep flow state?”

    Only a few things are needed: private offices and an understanding about when it is OK to interrupt someone.

    In-person relationships are vastly preferable to virtual relationships. See:

    • I’ve seen this work really well without private offices. In some cases, the lack of a private office culture is even more powerful.

  • Lyndi

    There are lots of tools we use at BizeeBee. Campfire rooms have become a staple in our communication. We have separate rooms for different things ie: customer support room, watercooler, development and so on. We also have Adium/Pigen open for individual conversations. Since we are a 100% remote team getting face to face time is done through Skype and team meetings through Google hangouts. My husband works for Cheezburger and their development team just started testing out Grove, because Campfire and Skype wasn’t working for them. 

  • I love monasteries, convents and cloisters. I’ve stayed in some. There’s an amazing peacefulness to them, which is inducive to lots of productive thinking or working. I don’t think startup environments are that peaceful, but they certainly have a focused streak to them.

    I’m using HipChat at the General Assembly in NYC, and it is revealing to see the inter-company chats across company walls. Technology does permeate the company walls if you let it, or if you poke your head out. 

    • I’m at the gate at my airport right now. Sort of monastery like if you approach it the right way.

      • agreed.  some of my best ‘in the zone’ moments have been at gates w/ headphones in and vi open.

      • True. There is a certain serenity about airports at certain times, contrasted with insanity at others. I’ll think about that tomorrow when I board my gate at 5:50 am.


  • “The monastic startup is a place where engineers do the best work of
    their lives. This place involves work with long stretches of
    uninterrupted time.”

    This idea is so powerful.  I think it means more than just quiet periods during the day without distractions.  It requires periods of weeks or months while developers are focused on a particular , challenging problem.  In many companies software releases are a grab bag of functionality and priorities.  Working towards this type of release divides time and attention in so many arbitrary ways, even if you are not literally interrupted on an intraday basis.  As a developer I find it much more productive to focus on recurring themes and patterns that emerge from the technology itself.  But it can be very hard to communicate how this is the case to someone who is not inside the code base.  In music and in sports I always learned by establishing focus on weak areas.  But in technology we don’t always focus weak areas, instead we add features and fix bugs which is a very different approach.

  • The most important tools are:
    a) set of high quality noise cancelling headphones
    b) respect for the flow of others

  • We are using Kickoff ( internally at Discovr, works quite well, although limited to Mac desktop only. Being a desktop app I find a real bonus, as I don’t get as distracted by opening another tab in the browser.

  • Alexander Close

    I think at times it’s more of a mind-state than physical surroundings.

    Early mornings: Slowly warming light, stillness in the air.  Streets have yet to fill and the phone won’t start ringing for a few hours.  A great time for solid thinking.

    Busy airport: The hustle and bustle.  Headphones on with a consistent, lyric-less track.  Cuppa-joe in the armchair and another hour before boarding.  Completely tuned out and focused in. Sometime surprising how much work can be accomplished.

    Either monastery could be ruined by message checking.  I think “monasticness” can be where you find it.

  • I used to work frequently at a Starbucks – unfortunately it came to the point that all of the regulars would come say Hi, every 15 minutes.  I’ve been working at home ever since and am amazed at how much more productive I have become.  I am more relaxed and at ease in the peaceful surroundings of my place.  I definitely have seen benefits in being able to work for long stretches without any major interruptions.

  • Methinks the new book, Quiet, about the power of introverts and introversion… “in a world that can’t stop talking” might appeal to you Brad…and Amy. Great writing and apt point

  • I do not think the concept of “monastic startup” need be limited to engineers only doing the best work of their lives. Pursuit of this level of serenity and purpose more often than not requires cooperation and collaboration with the other parts of a winning team that make things happen along parallel lines. One venture I led required a heavy respect for our engineers’s time, but also called for my input (strategy/ops). We used Basecamp and a modified ticketing system to track pesky to-dos, and to document points where more monasticism was called for. 

    I find my own monastic peace at cruising altitude over flyover country, B&W’s hugging my ears, Kraftwerk blasting “Computer Love”.

  • I read the article on “The Next, Next Thing”, and it was great–it really motivated me to start thinking not just about what the technology today can do for the future, but rather, what technology can we make in the future to better our world even more?
    What’s the most innovative concept/venture you see in the pipeline now that will enhance our lives 5-10 years from now?

    • Hands-down, the impressive strides being made in medical nano tech. 

  • Maintaining that quiet place where you can get some work done without distractions is hard to do. It helps if you have a physical location and device that simply does not support distractions. e.g. some other room (not the usual office where people can pop in) with a laptop that has nothing installed on it that can lead to distractions (i.e. no skype, chat, links to social sites, etc.). 

  • Tom Labus

    Walking every day is my monastic experience.

    No phone, no music.

    It revives me daily.

  • kjkdc

    I like the monastic reference in your stream of thoughts.  Eric Maisel in his book “Brainstorm” and “Creative Anxiety”, makes the distinction between the Big brain that can tackle big thoughts, and big tasks to  have you conjoined with your muse in no time, vs. the Small brain, that is all about lists, chatter, social networking, that can distract you from the creative process. He recommends getting up early, and first thing, while practically in the dream state, using a ritualized way of getting into your “big brain” to do your most creative work. I find the sooner I do it, the faster I get into that state. Otherwise your brain is riddled with the usual questions; where are my glasses, what will I have for breakfast, did I pay the phone bill….The problem is not only training yourself to get into that flow quickly but creating sacred space for large blocks of interrupted time to create, once in the flow. 



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