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Page history last edited by Tantek 8 years ago

My Next Startup

I'm collecting notes on lessons learned from past professional experiences (both my own, and that observed from others) as background material for when I do my next startup.


Totally a work in-progress and expect lots of change as I iterate.


professional requirements

Professional requirements include everything from workflow, work habits, productivity methods, collaboration, meetings, to community presence and interactions.



Everyone in the company, and especially anyone in a leadership position, must use or at least understand and use basic Getting Things Done (GTD) techniques such as splitting work between collecting, processing, doing, and understand terms and phrases such as "waiting for", "date time dependent tasks", "next actions". Exception: if someone is a new college-hire, then they should be paired with a GTD expert in the company and mentored on the use of GTD until they become self-sufficiently proficient at GTD. All other professional hires should be expected to know or teach themselves GTD. Mentorship is an option for professional hires as well, but they are expected to be sufficiently self-aware to explicitly ask for it.



  • Everyone in the company must be proficient with wiki editing and use the company internal wiki daily to collect work related inbox items, keep status on projects, etc.
  • Company internal wiki should be setup with https and accessible from the extranet.



  • Everyone in the company must be at least a little experienced with IRC and should use the company internal IRC channels whenever possible to discuss things on the company internal wiki.
  • Would be nice if edits to the company internal wiki went to the company internal IRC channel.
  • Company internal IRC server should be securely accessible from the extranet (setup info needed).


rational decision making

Develop demonstrate encourage rational decision making under pressure


This applies far beyond doing a startup, but is certainly essential.

The above issues regarding adding investors are a good reason why it is necessary to develop skeptical scientific thinking as a core way of just "being", because when you are under pressure, you revert to your core.


If your core is emotional, you will make the wrong decisions.


Emotions cannot plan moves ahead, emotions merely react. Every good chess player learns this lesson very early on.


This is why scientifically critical thinking is important to integrate as a core way of thinking, training yourself to even react scientifically/rationally rather than mystically/emotionally.


It's because of pressure, high pressure, and at the extreme, the flight or fight response.


collaborative authoring

There will be NO internal use of emailing around Word documents to do collaborative authoring. Seriously, that collaboration culture has been obsoleted by wikis. Here is a picture (from the blog post Wiki collaboration leads to happiness) help make it clearer why:




Currently pertains only to face-to-face (F2F) IRL meetings.


Meetings are such a common source of inefficiency and other problems that they need to be explicitly addressed.

Avoid meetings

Most meetings are an exceptionally inefficient use of time. SeeCommunicationProtocols for how to communicate like 99% of what people think they need a meeting to communicate.


No meetings before noon

People tend to be more creatively productive in morning (compared to afternoon) hours, and thus it is best to have a "no meetings before noon" policy in order to encourage and enable individuals to make use of that time to create. In particular:

  • Build rather than blab. Be creative and constructive rather than communicative. I have found that I'm mentally most alert, and most creative before noon, and thus prefer to spend that time creating, writing, coding etc., rather than communicating.
  • Physical condition is more important than meetings.
    • Physical workouts enhance mental alertness, creativity, energy, and motivation. In addition maintaining and enhancing physical fitness is for me a higher priority than any meetings (and should be for you too) and thus I prefer to keep the morning completely clear in order to provide the most flexibility in the combination of physical workout and creative work output that seems optimal or ideal as of that morning.
    • Physical health is more important than meetings. Sometimes your body needs extra time (asleep) to recover, for any number of reasons:
      • fighting off some virus (cold/flu - see HowToKickColds) and a few more hours of sleep may help crush it. The economic trade-off here of spending a few hours fighting off a cold rather than days in downtime when you come down with it are obvious. And yet, morning meetings force people to go to work when they are in the process of getting sick (they might just feel extra tired) and thus really get sick.
      • worked out a bunch the previous night (like 3-4 hours of climbing) and your body needs extra time to repair/restore itself.
      • returned from a trip to a different time zone (especially more than 3 hours) and your body needs more sleep to recover from travel stresses, and reset its body clock.


Noon-2pm meetings have food

Whoever calls/organizes a meeting from noon-2pm must provide healthy food to at least all requested attendees, and preferably all attendees.

  • People typically eat lunch sometime during noon-2pm. Don't presume to make them schedule their lunch around your meeting time. If you insist on taking up someone's time between noon-2pm make sure you at least offer healthy food to any/all attendees. Be sure to know ahead of time or ask explicitly what everyone's FoodPreferences are. If you are unable to provide healthy food in line with everyone's food preferences, then schedule your meeting 2pm or later.
  • EXCEPTION: recommend to potential attendees well in advance that they should eat an early lunch (late breakfast) BEFORE coming to the meeting as there won't be any food provided. Even then, you should still offer some healthy snacks, like fresh fruit, because people might not get around to eating beforehand.


No status meetings

Status meetings are a complete waste of everyone's time in the meeting and the existence of such meetings are usually are a sign of bad management, irresponsible employees, or both. Instead: every employee should continuously keep their status on any company project up to date on their wiki page(s).


If an employee isn't keeping their projects up to date on their wiki, then as their manager talk to them 1:1 about it, and figure out what's blocking the employee, and remove any obstacles. The far too common practice of calling an employee on the carpet in a status meeting in front of their peers demonstrates a lack of respect for the employee, sets a bad example, and hurts company culture - a sign of really bad management. If you're a manager, don't do that, and if your manager does that, tell them, let's discuss this matter in a 1:1. If they continue to berate you, walk out of the meeting. Yes, you should be prepared to quit if your manager is a) dumb enough to behave in this manner, and b) disrespectful enough to ignore your request to discuss the matter in a 1:1.


No standup meetings

 Theoretically a "stand up" (often called a scrum) meeting is supposed to be a quick meeting at the start of the workday (often starting around 9am to 10am) where everyone in the room gets a chance to indicate what obstacles they have that others in the room can help them with. In practice this almost never works and fails in a number of ways:

  • People treat it like a status meeting and list all the crap they are working on, probably because they are insecure, or have big egos (or both) and thus like bragging about how important all the things they are working on are, hearing themselves speak, or maybe because they enjoy the powertrip of wasting everyone's time in the room.
  • People start discussing the issues rather than just saying hey I need 5 (whatever) minutes of your time to discuss topic X.
  • People end up going around in a circle and going thru the motions of saying "nothing for the team". Day after day.
  • ... I know there are other reasons these are a waste of time, and will document them later. 

See also:


SCRUM does not work

SCRUM = Squashing Creativity + Responsibility Under Micromanagement. As you might infer from previous two points about no status and no standup meetings, I'm very much opposed to the daily-status-standup-meeting of SCRUM. In my opinion use of such an artificial every-24-hour-checkpoint in attempt to apply pressure/force for daily accountability encourages far too much of a micromanagement culture in practice and is thus both an immediate negative to everyone involved (no one likes being micromanaged, and no one should like micromanaging), and encourages an increasingly patronizing and disrespectful corporate culture over time.


War Team Meeting bad framing

War Team Meeting = counterproductive framing. As Chris Wilson tweeted:


"War team" meetings are like dancing about architecture.



community presence

  • be present. Be transparent (proactively honest) with your community. Maintain a PositiveCommunities tone as well as explicit community guidelines (e.g. Flickr) and code of conduct (e.g. O'Reilly).
    • blog. keep a blog and post major and lengthy updates there. if you allow comments, actively removing spam and Trolls.
    • tweet. keep a twitter account (preferably using the name of the company) and provide updates of general interest.
      • status tweet. optional. consider keeping a separate Twitter account (like companyname_status) for more frequent updates with the precise status of the company's services/products (up, down, slow, disabled, updated etc.) for those who want/need more frequent updates and more detail.
  • listen Track all mentions of company and product names on (in relative order of urgency) using feeds from:
  • participate
    • wiki. create a public community wiki and garden it, actively removing spam and Trolls.
    • irc. create a public irc channel, perhaps on Freenode, and actively admin it.
      • set up an irc bot to post public wiki changes to the public IRC channel.
    • follow the users. Create and maintain a company presence whereever users are discussing company and products. be passive and responsive, and avoid any active/proactive marketing. use the company blog and twitter account for proactive messaging.


Value feedback by expertise not money

Value feedback for quality of time not amount money given. This is so important that it deserves it's own subsection.


Whether on a free version (there almost always should be) of a web service or paid version, the community feedback you get, especially public feedback from usability/design/technology experts should be treated as more important than feedback from those that give you money in general.


The time and expertise that such experts choose to give (donate to) you is of far greater value than the money from subscription fees or even from investors.


I emphasize this difference in value because all too many startups have been distracted by the literal demands (bug reports, feature requests, random demands) from so-called "paying customers" and/or investors, at the expense of the much more accurate feedback from those that know better and contribute with their time (and perhaps even reputation) instead of money. Excuse(s) given (with obvious flaws)

  • The VCs are demanding we focus purely on monetization and get profitable by the end of the quarter/year so we don't have to do another round etc. ... therefore we have to listen only to paying customers (since paying = profit right?), advertisers, and ignore all the free stuff/services/advice. Flaw: the free advice will likely provide a better prioritization of service improvements to increase profitability / paying customers than what the paying customers (and certainly advertisers) think they want (and thus ask for).

Often smart folks can figure out how to efficiently use free/commodity tools/services on the web, and the dumb (meaning nothing derogatory, just "not so smart") folks are the customers that pay for tools/services that are otherwise commodities (like text editing). Or you might have a premium quality service (like Flickr) which attracts paying smart folks, that's even better.


I'm not saying to disregard feedback from paying customers, but rather to consider it secondary to feedback from usability/design/technology experts.


adding investors

By definition if you are doing a startup, you are investing. Your time, most likely your money, likely a non-trivial amount, your energy, your creativity etc.


Anyone else is an addition.


Adding investors is very tempting, especially if you don't have savings base to bootstrap with. Or even if you do, it's tempting to address issues of time, speed of scaling/growth, by accepting investment.


The challenge is that every investor you add will influence what you do, how you spend your time, and how much attention you can pay to everything else that matters to making your startup work.


Investors may (likely should) add pressure to you to become profitable. Pressure to be profitable is good, not bad.


This pressure will grow with each investor you add, with the magnitude of each investor, and likely with how much they don't know you. The more socially distant, the less they will just trust you, your track record etc., and thus will apply more pressure for profitability sooner.


Even high pressure is not necessarily a bad thing, as long as you don't have it trick you into thinking/acting irrationally/emotionally. That's the problem.


Listening directly/reactively to the people that buy (or invest in) your product is not the best way to profitability.


Listening primarily to paying customers/investors is an *emotional* reaction, not a rational one.


It takes experienced wisdom to understand this, exceptional "force of will" to follow through on that understanding, and thus every additional investor you consider you need to consider within the context of your capacity for understanding such pressure, and your ability to maintain independent rational thought in the face of such pressure.



Professional requirements (as stated above) and required skills.

  • GTD. See above.
  • Wiki editing and use in personal productivity as noted above.
  • IM (Instant Messaging)
  • ... more to be added.

Desired skills (not required, but certainly will make many things easier, and can be quickly taught)

  • IRC
  • Community Management - everyone who says they work for the company or on a product could be asked a question, in person, online etc. about either and needs to be able to think and act in a PositiveCommunities mindset.
  • ... more to be added.


employee benefits

  • health care
    • provide access to information to help employees make healthier eating and lifestyle choices (related: BodyOptimization).
    • when providing food for employees (e.g. lunch meetings) provide healthy food, preferably with documented source(s) of origin.
    • encourage employees to engage in daily physical fitness exercises (related: BodyOptimizationTechniques )
    • medical insurance - figure out how to make this as seamless and low hassle as possible for employee(s)
  • mass transit commute
    • e.g.: subsidizing Caltrain, MUNI passes.
    • benefits: peace of mind, psychological well-being, reduced risk of in-commute car accident, reduced incidents of car commute stress, reduce stress overall, increase commute productivity


interface design

When designing various interfaces, whether web (desktop/laptop/mobile), custom applications, or even text / command lines (e.g. email or direct messaging), re-use the best aspects of existing successful sites, services, and tools.


social content website design

(perhaps move this section to its own page when it gets big)

When designing or building any site that has any aspects of personalization (where it behaves differently for different people, from preferences to profiles) and content contribution, pay close attention and mimick all the excellent decisions made by existing well-designed sites, e.g. in rough order of design importance / coding order:

  • Twitter, Instagram - simplify simplify simplify
  • Digg - public domain tou. Specifically this paragraph:

    By submitting Content to Digg, you warrant that you own all rights to the Content, agree that the Content will be dedicated to the public domain under the Creative Commons Public Domain Dedication, available at http://creativecommons.org/licenses/publicdomain/ and that you will not object to the use of the Content by Digg in any context. To clarify, the above does not apply to the Content on external sites linked to by the original submission.

    This is a brilliant innovation by Digg (see video interview where I discuss it).
  • Netvibes, Trim, Posterous and SignApp - the ability to personalize and create content (even if such content is just shortened URLs) with just a cookie, no login creation required. Brilliant. lower the barrier to experimenting, trying it out, then once the user has created sufficient value on the site (probably directly proportional to time they've spent on the site, and content/changes made), it provides incentive to the user to create a login.
  • Get Satisfaction - support sign-in/sign-up via hCard and OpenID, as their sign-up page does
  • Flickr - groundbreaking work in dynamic interfaces (e.g. for tagging, changing title/description), shared content curation (editing/deleting notes/comments/tags made by others on your content), blocking. Simple clean elegant layout that's pleasing/relaxing to use.
  • Youtube - make it super easy to share/embed links/content from the site that provides a path back to the original content on the site
  • Dopplr - simple beautiful functionality. "Mute" functionality is genius and should be required for any social site that has both a friending feature and the notion of receiving updates from friends. From their http://www.dopplr.com/account/connections page which shows "Mute" links next to each person:

    Dopplr takes privacy and politeness seriously. Only those people that you choose to share trips with can see your travels.

    When someone shows you their trips we encourage you to reciprocate but you don't have to. If for some reason you'd rather not see someone's travels you can "mute" them. They will not be informed of this, and you can "unmute" the person at any time.

  • Upcoming - very nice and non-judgmental/non-bugging friends vs fans distinction.
  • Pownce (live site no longer available)
  • original Blogger (original Blogger tool no longer available on the Web)
    • you would give it your FTP user/pass (use OAuth instead today), and it would let you post/edit blog posts to your domain. Even if/when the Blogger tool/service went down, your website and thus blog would still be up and available.
    • examples of sites/data/permalinks lost (personally even)
      • 2007 Consumating (.com) - acquired by CNET in 2006 and shutdown in 2007, all permalinks lost.
      • 2008 Pownce (.com) - acquired by Six Apart in 2008, placed into read-only mode 2008-12-15, all permalinks lost 2009-01-31. Very irresponsible of Six Apart, a blogging company who thus should know better (at least some know better), to abandon permalinks of an acquired content posting service.
      • 2009 Magnolia (http://ma.gnolia.com/ has current status of data loss incident)
      • 2009 (expected) Dodgeball acquired by Google in 2005(?), planned read-only transition 2009-03-01, expected loss of permalinks to profiles and user-contributed venues perhaps a month or so after.
      • 2009 (expected) Jaiku acquired by Google. Expected to be shutdown similarly to Dodgeball, shutdown date unknown.
    • lesson: use and make tools that let you host your data and permalinks on your domain. (as tweeted 2009-035)
    • see also related: Building Blocks for Independents presentation/site which mentioned original Blogger tool as an example, and Steven Pemberton at XTech talk (which came long after the original Blogger, but failed to cite/mention it)

Take into account academic studies of / papers on social networks and social network sites.


paid service website design

(perhaps move this section to its own page when it gets big)

There are numerous ways to fund websites, at a minimum making them self-sufficient, and hopefully even providing a source of income to fund the creation of more websites etc. Here are some design inspirations:

  • Ads when not-logged in. show ads to not-logged in users (Flickr does this, but I'm not sure if that was originally their idea, or if they or I saw it somewhere else first.)
  • Amazon Affiliate links. link to Amazon for canonical references to books, music, movies and use affiliate codes
  • Two tiers for users provide two-tier annual subscription vs. free services
    • Pro Flickr/Pownce "Pro" vs. free accounts, better/additional avatar/theme that shows pro users' higher "status".
    • Patron Perhaps when starting out, start with the notion of "Patron" accounts
      • 2008-02 mentioned this idea to Larry Halff to do for Magnolia because there are many people who would proudly donate $20 a year for an excellent free service.
      • Give people a nice way to easily support the service, and show that they do without an expectation of more features etc.
      • Provide them with a badge/avatar/icon (similar to above "Pro" users) that demonstrates their support of the site
      • Maybe auto-upgrade Patrons to Pro users when Pro features are added (if original launch lacks Pro features).
      • Perhaps charge less to Patrons than Pro users, thus rewarding patrons with more services for their earlier support.
  • separate domain for CC charge info. minimize chargebacks by using a custom domain for credit card charge information, e.g. 37Signals shows up as 37SIGNALS-CHARGE.COM on your credit card statement (via Amit 2009-01-22).
  • low latency for shopping. numerous studies (citation needed) have shown that the more responsive the shopping interface, the greater the number of completed sales. When looking at what area of website perf to optimize, transaction related perf might be the best place to start.
  • minimal steps to purchase. Amazon's 1-Click (licensed by Apple and thus also in use on the iTunes music store, and perhaps responsible for making it 36% of Apple's revenue) similarly increases completed sales. Thus one should minimize purchase transactions to two steps (until potential revenue increase can justify licensing 1-Click) to maximize sales completion.


tagging website design

  • Flickr, Delicious - the original tagging popularizers
  • easy copy/paste of tags from one content item to another
    • Both Flickr and Upcoming get this wrong, in that you have to carefully select across several lines of tags, and then when you copy, the tags are interspersed with "[x]" characters.
  • easy deletion/undeletion of tags. one click (no confirmation) to delete a tag perhaps with the common "[x]" UI element, mark it as deleted, and allow simple undeletion with a "[+]"
    • Both Flickr and Upcoming get this wrong with a confirmation dialog that you have to dismiss every single time you want to delete a tag, which makes deletion of several tags quite onerous/tiresome. Plus they lack undo. Per Raskin (citation needed to respective tantek.com blogpost on this from his talk at BayCHI) there should be no confirmation dialog for such a simple undoable action.


event website design

(perhaps move this section to its own page when it gets big)

In addition to the above since all event websites are (or should be) fundamentally social, some really simple design basics learned from existing well-designed sites:

  • Upcoming.org lessons:
    • Make public events public. Don't require login to view public events. Helps with search engine indexing, one less step for people who may not be logged in.
    • hCalendar on all events.
    • private events viewable only by friends/acquaintances. This is a nice simple model for private events that doesn't require a lot of (re)curation of invite lists etc. (as opposed to Evite/Facebook approaches). It's simple, only add people as friends on an event site if you are totally comfortable having them come over to your residence.
  • additionally:
    • watching events from contacts (as opposed to friends/acquaintances) without allowing access to your private events. makes sense for accounts that represent organizations, e.g. I may want to know about events that the user "Creative Commons" creates and or watches, but I don't necessarily want my private events being viewable by the "Creative Commons" user (which may be an account accessed by multiple random people I don't know).


location website design

Sites for publishing/sharing location based information would do well to learn from the design insight (and mistakes) of the following services

  • Dodgeball. The original, and still unparalleled. Unfortunately scheduled to transition to read-only mode 2009-02-28, and shut down perhaps a few weeks later. See Ariel's analysis/writeup of Dodgeball's features
  • Brightkite. The first site/service/tool to make me see a reason for and actually want a camera phone. That being said, lots of really dumb design decisions. At the same time overfeatured/overcomplicated and yet missing key simple/convenient features that Dodgeball pioneered, like the simultaneous checkin/shout: @CTTP ! co-working in the window office on a beautiful day and groups: localsfpeeps @ CTTP ! power outage. anybody else lose power?
  • Google Latitude should take a look at, just because it is Google, which means they will inevitably have some design brilliances and goofs.


photo website design

Whether hosting photos or only allowing annotations of photos hosted elsewhere (better to start there), here are some notes on what to do right both from existing well-designed sites and a few brainstorms:

  • Flickr - there is so much that Flickr did right, that when in doubt, mimic Flickr's design.

Things I've always wanted:

  • add a photo note at any zoom level on a photo. e.g. on Flickr, you can only add photo notes on the main page for a photo, not on any of the "All Sizes" views.
  • low-intrusivity progressive disclosure of photo notes. i.e. per Zeldman's critique of Flickr:

    Hate how Flickr note rectangles demand your attention. Like people leaving a movie, shouting plot spoilers to those waiting to get in.


invoice collections

This is something that every independent I know has difficulty with, either personally (not wanting to do collections tasks) or in actually getting folks to pay. Just collecting notes for now on how to deal with this.








others startup notes


see also



  • Every company I've
    • worked for (see my seriously out of date resume).
    • started (e.g. my previous startup, 6prime.)
    • advised (see my Advisory Roles)
  • Tara's post that mentioned her annoyance with 9am meetings got me to finally start writing this stuff up publicly, in particular the Meetings section, which has long needed to be written up.


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