Brad's Books and Organizations

Books

Books

Organizations

Organizations

Hi, I’m Brad Feld, a managing director at the Foundry Group who lives in Boulder, Colorado. I invest in software and Internet companies around the US, run marathons and read a lot.

« swipe left for tags/categories

swipe right to go back »

Software and Failure

Comments (13)

As Amy and run around like silly people packing up to head back to Boulder tonight, I stumbled upon two fantastic posts on the web.  Consider this your daily reading if you read nothing else.

The first is titled Five Life-Changing Mistakes and How I Moved On by Julie Wainwright.  Julie is now the co-founder of SmartNow.com but is infamous for being the CEO of Pets.com.  Her post is personal and phenomenal.  She identifies five mistakes she made leading up to and during the simultaneous failure of Pets.com and her marriage.  She then describes – point by point – how she moved on.  The mistakes follow; you’ll need to click through to her article to see how she moved on. (Thanks Heidi).

  1. Allowed others to define me.
  2. I built my image of myself on two main supporting pillars.  When those collapsed, I did too.
  3. I stopped believing in myself.
  4. I stopped taking care of myself.
  5. Allowing my head to rule my heart.

The second is titled It’s the Software, Not You in the NY Times by David Pogue.  If you’ve been following along at home you know that I’ve been deeply immersed in human computer interaction (HCI) during the past year.  Pogue gives several great examples and ends with "Why do software designers want their work to appear more complex instead of less? I just don’t get why they don’t get it. So the next time you’re frustrated by software complexity, take heart; much of the time, it’s not you. It’s them. It’s designers who have something on their mind other than software intelligence."  Right on!

Both are worth reading and savoring.

  • Luca

    I am doubtful about David Pogue's mental sanity. He wrote: “I actually like Delta quite a lot”. How could a sane person say that about any airline these days??? ;-)

    And yes, Julie Wainwright's piece is indeed phenomenal.

  • tedr

    I expect when my story is said and done I'll have a lot more than 5 key mistakes made, so I don't mean to sound smarmy, but when I started my current venture I could really feel people trying to move into being a different person.

    Around that time I got a fortune cookie, that was move advice, that said 'Write your own story. Don't let others write it for you.' which I kept in my wallet for 4 years until I recently taped the pieces together and have pinned next to my desk.

  • bill

    The Pogue question is a simple one, and the answer(s) are as well (done in 2 comments)

    1. The curse of the startup – you duct-tape your app together and by the time you get customer traction it's too involved for most companies to rebuild on the architecture they should have used in the first place. Chalk this up to poor planning or lack of budget to do it right in the first place.

    2. Ego. Everyone in software knows of the person who's “way” can't be questioned. Like what was alluded to in Julie's piece, people often get behind that person (it's easier) rather than question them, and often you're company is stuck with his/her version of “great”. Oftentimes these people are praised for the elegance of their coding, not the elegance of their results.

  • bill

    3. Lack of ego. In some environments, engineers are rewarded (i.e. – they keep their jobs) by “appearing” busy or entrench themselves in a position where it is dangerous to remove them. Or they are misguided and think that the measurement of their skills is defined by how much they overthink the problem, and a very complex solution proves they really “get it”. In these people's mind, if the solution was really more simple, the others would have thought of it already. So it becomes a complexity arms-race, avoiding the simplicity elephant in the room.

    4. Haste and impatience. This goes along with number 1, but even in established companies, sometimes the need to meet deadlines or “get this feature in” means that sometimes UI gets put to the back burner in lieu of being able to say it is in there – Apple's fiasco with Exchange in MobleMe seems to be a recent example of this.

  • bill

    I'm not an engineer, but I've had to sell the fruits of those labors, and I have seen first-hand good designs, as well as many of the examples above. Good UI and good design in my opinion have to come from the top down – a cult of personality that praises those qualities – in order for the right engineers to feel confident in prioritizing them over gettin' er dun. And the management that praises simplicity, scalability and iterative design from the start? I can count those managers that I've met on one hand (and they're all retired rich and successful).

  • Aziz Grieser

    I left a long comment on Julie's blog. You've sent me to other blogs where I've done the same. I'll say it once more: you should be charging for referral traffic. :)

  • http://observationists.blogspot.com/ Allen Sligar

    Good stuff on both blogs. I've experienced some of the same things over the last few years less as exec management coming in from the top laterally than as an entrepreneur building up from the bottom. It's hard either way, but the good thing is that even in less than optimal outcomes you get the benefit of learning great lessons.

    Good stuff, thanks Brad

  • Steve Bergstein

    Pogue needs to read The Design of Everyday Things. The reality is that building usable software takes work (and, therefore, money) – there are effective methodologies for achieving it.

    Apparently you and your partners have decided that there may be a market for highly-usable software. I hope that you're right. A prior employer believed that “usability doesn't sell sofware.” That always irritated me.

  • Jim

    Pogue is mistaken about the airline software, and your endorsement of it his piece simply adds to the volume coming from the peanut gallery.

    Delta and others ask those questions as a security measure. It's a common security aphorism that two key elements of a secure transaction are a) something you physically possess (a credit card in this case), and b) something you know. Should someone have misappropriated his credit card, allowing possession of it alone to provide access to the flight would have been a significant security breach.

    By the way, when was the last time you funded “good design”? Never, I'm going to guess.

    • http://www.feld.com Brad Feld

      Jim – I respectfully disagree. If you compare the various airline kiosk software some ask many more of the “obvious” questions than others. Ultimately, the kiosk doesn't provide real security – presumably that's why the TSA is omnipresent before you can actually get to the gate.

      Good design is a very important part of what we are looking for in software companies that we fund. Our entire theme around human computer interaction is based on the notion that there is a much better way to interact with computers vs. the way we currently do it – and much of that is a software (and design) problem.

      • Jim

        Oh? Unless you've simply made up your mind, you might want to look at:

        http://tinyurl.com/6ar69x (“Special Report: Are airline kiosks a security threat?”)

        As the Secret Service men quoted are trying to convey: convenience is incompatible with security. A related piece appeared in Slate on Oct. 30, 2006.

        And what is this “real security” you speak of? There is no such thing. In addition, there is not just one layer of security, but several.

        It is very pleasing to hear of your commitment to good design and HCI. Any examples of investments that meet this standard? There are indeed so few.

        Have a safe flight.

        (By the way, I would have left comments for Pogue, but he doesn't allow that. I suppose he just likes to complain.)

        • http://www.feld.com Brad Feld

          I took a look at the Special Report. I completely agree with it. I think it's saying “the kiosks are not an effective security layer.” My comment was “the kiosks don't provide real security.”

          I didn't assert that there is actually any “real security”. Rather, I said the kiosks don't provide it. I don't think TSA provides it either – that's the thrust of a lot of the article.

          Re: Good design: I think you'll see this as a core of Oblong. It's also a core of Smith & Tinker. I like to think that many of our other investments outside the HCI segment also have great software and UI design.

  • sigmawaite

    I read Ms. Wainwright's thoughts and would have approached the situation with a simpler and hopefully better explanation: By analogy if going to fly across the Atlantic, then need to be quite sure of the planning and engineering or risk getting cold, wet, and maybe dead.

    Then I would say that the causes of Ms. Wainwright's difficulties were just in planning and engineering. This does not necessarily mean that she was at 'fault': Sometimes are in a hurry and just tie it together with wire and glue, takeoff, and hope, and that's a large club. Sometimes that works, and that's a smaller club. If wire and glue are what she had in mind, then she should have no struggles with bad feelings and troubling questions. Otherwise, she just needed better planning and/or engineering, may want to do this the next time, and that's a large club.

    For more on the analogy, during the flight have good charts, do good navigation, and use instruments, radio, and radar. Before the flight, have alternate destinations, reserve fuel, redundant equipment, life rafts, etc. Aviation learned these lessons the hard way, and they are good lessons.

    Generally, if stay anonymous, then the world is not thinking about you, is indifferent to you, is not working against you, and is just often challenging. Make a good attack on the challenges and can expect to win. Otherwise might get lucky and still win.

    If fail, then should address indifferent external reality or the possibly non-objective opinions of other people? That is, primarily facing reality or people?

  • http://intensedebate.com/people/luca8090 luca8090

    I am doubtful about David Pogue's mental sanity. He wrote: "I actually like Delta quite a lot". How could a sane person say that about any airline these days??? ;-)

    And yes, Julie Wainwright's piece is indeed phenomenal.

  • bill

    I'm not an engineer, but I've had to sell the fruits of those labors, and I have seen first-hand good designs, as well as many of the examples above. Good UI and good design in my opinion have to come from the top down – a cult of personality that praises those qualities – in order for the right engineers to feel confident in prioritizing them over gettin' er dun. And the management that praises simplicity, scalability and iterative design from the start? I can count those managers that I've met on one hand (and they're all retired rich and successful).

  • tedr

    I expect when my story is said and done I'll have a lot more than 5 key mistakes made, so I don't mean to sound smarmy, but when I started my current venture I could really feel people trying to move into being a different person.

    Around that time I got a fortune cookie, that was move advice, that said 'Write your own story. Don't let others write it for you.' which I kept in my wallet for 4 years until I recently taped the pieces together and have pinned next to my desk.

  • http://intensedebate.com/people/aziz_griese5636 aziz_griese5636

    I left a long comment on Julie's blog. You've sent me to other blogs where I've done the same. I'll say it once more: you should be charging for referral traffic. :)

  • Allen Sligar

    Good stuff on both blogs. I've experienced some of the same things over the last few years less as exec management coming in from the top laterally than as an entrepreneur building up from the bottom. It's hard either way, but the good thing is that even in less than optimal outcomes you get the benefit of learning great lessons.

    Good stuff, thanks Brad

  • Jim

    Pogue is mistaken about the airline software, and your endorsement of it his piece simply adds to the volume coming from the peanut gallery.

    Delta and others ask those questions as a security measure. It's a common security aphorism that two key elements of a secure transaction are a) something you physically possess (a credit card in this case), and b) something you know. Should someone have misappropriated his credit card, allowing possession of it alone to provide access to the flight would have been a significant security breach.

    By the way, when was the last time you funded "good design"? Never, I'm going to guess.

  • http://intensedebate.com/people/sigmawaite sigmawaite

    I read Ms. Wainwright's thoughts and would have approached the situation with a simpler and hopefully better explanation: By analogy if going to fly across the Atlantic, then need to be quite sure of the planning and engineering or risk getting cold, wet, and maybe dead.

    Then I would say that the causes of Ms. Wainwright's difficulties were just in planning and engineering. This does not necessarily mean that she was at 'fault': Sometimes are in a hurry and just tie it together with wire and glue, takeoff, and hope, and that's a large club. Sometimes that works, and that's a smaller club. If wire and glue are what she had in mind, then she should have no struggles with bad feelings and troubling questions. Otherwise, she just needed better planning and/or engineering, may want to do this the next time, and that's a large club.

    For more on the analogy, during the flight have good charts, do good navigation, and use instruments, radio, and radar. Before the flight, have alternate destinations, reserve fuel, redundant equipment, life rafts, etc. Aviation learned these lessons the hard way, and they are good lessons.

    Generally, if stay anonymous, then the world is not thinking about you, is indifferent to you, is not working against you, and is just often challenging. Make a good attack on the challenges and can expect to win. Otherwise might get lucky and still win.

    If fail, then should address indifferent external reality or the possibly non-objective opinions of other people? That is, primarily facing reality or people?

  • bill

    The Pogue question is a simple one, and the answer(s) are as well (done in 2 comments)

    1. The curse of the startup – you duct-tape your app together and by the time you get customer traction it's too involved for most companies to rebuild on the architecture they should have used in the first place. Chalk this up to poor planning or lack of budget to do it right in the first place.

    2. Ego. Everyone in software knows of the person who's "way" can't be questioned. Like what was alluded to in Julie's piece, people often get behind that person (it's easier) rather than question them, and often you're company is stuck with his/her version of "great". Oftentimes these people are praised for the elegance of their coding, not the elegance of their results.

  • http://intensedebate.com/people/steve_bergs2127 steve_bergs2127

    Pogue needs to read The Design of Everyday Things. The reality is that building usable software takes work (and, therefore, money) – there are effective methodologies for achieving it.

    Apparently you and your partners have decided that there may be a market for highly-usable software. I hope that you're right. A prior employer believed that "usability doesn't sell sofware." That always irritated me.

  • bill

    3. Lack of ego. In some environments, engineers are rewarded (i.e. – they keep their jobs) by "appearing" busy or entrench themselves in a position where it is dangerous to remove them. Or they are misguided and think that the measurement of their skills is defined by how much they overthink the problem, and a very complex solution proves they really "get it". In these people's mind, if the solution was really more simple, the others would have thought of it already. So it becomes a complexity arms-race, avoiding the simplicity elephant in the room.

    4. Haste and impatience. This goes along with number 1, but even in established companies, sometimes the need to meet deadlines or "get this feature in" means that sometimes UI gets put to the back burner in lieu of being able to say it is in there – Apple's fiasco with Exchange in MobleMe seems to be a recent example of this.

  • http://intensedebate.com/people/bfeld bfeld

    Jim – I respectfully disagree. If you compare the various airline kiosk software some ask many more of the "obvious" questions than others. Ultimately, the kiosk doesn't provide real security – presumably that's why the TSA is omnipresent before you can actually get to the gate.

    Good design is a very important part of what we are looking for in software companies that we fund. Our entire theme around human computer interaction is based on the notion that there is a much better way to interact with computers vs. the way we currently do it – and much of that is a software (and design) problem.

  • http://intensedebate.com/people/bfeld bfeld

    I took a look at the Special Report. I completely agree with it. I think it's saying "the kiosks are not an effective security layer." My comment was "the kiosks don't provide real security."

    I didn't assert that there is actually any "real security". Rather, I said the kiosks don't provide it. I don't think TSA provides it either – that's the thrust of a lot of the article.

    Re: Good design: I think you'll see this as a core of Oblong. It's also a core of Smith & Tinker. I like to think that many of our other investments outside the HCI segment also have great software and UI design.

  • Jim

    Oh? Unless you've simply made up your mind, you might want to look at:

    http://tinyurl.com/6ar69x ("Special Report: Are airline kiosks a security threat?")

    As the Secret Service men quoted are trying to convey: convenience is incompatible with security. A related piece appeared in Slate on Oct. 30, 2006.

    And what is this "real security" you speak of? There is no such thing. In addition, there is not just one layer of security, but several.

    It is very pleasing to hear of your commitment to good design and HCI. Any examples of investments that meet this standard? There are indeed so few.

    Have a safe flight.

    (By the way, I would have left comments for Pogue, but he doesn't allow that. I suppose he just likes to complain.)

Build something great with me