Sending Stuff To The Wrong People

I got a bunch of emails yesterday that were clearly not meant for me. I replied to let the senders know and deleted them without reading beyond what I had read to know it wasn’t for me.

Then I saw this tweet by Chris Dixon:

Then it all jelled in my mind. Gmail was autosuggesting the wrong people to a large swath of its users over the weekend. I was struggling with the same problem but I hadn’t realized it was a service wide issue.

Sending emails to the wrong people is embarrassing and potentially much worse. The same is true of google docs, dropbox, and a host of other cloud based services where we create and store sensitive information. At least google docs pops up the warning “you are about to send this outside of your domain.” That has saved me many times from sending a google spreadsheet or doc with personal information to a woman with the same first name in Mellon’s Private Bank instead of my wife. You would think Google would know my wife is more important. But it does not, particularly on mobile.

The thing of it is that Google is so good at knowing who you might want to send something to that they should do more than they do right now. They could easily pop up a warning saying “you don’t normally send this kind of document to this person” or “you don’t normally include this person in the group you are sending this to.” These sorts of data driven protections/warnings would further cement the already airtight lock they have on me and many others who use gmail and google docs.

But try as we might, we are human and prone to error. It is almost certain that each of us will send something super confidential to someone who should not see it at some point in our life. My hope is when I do that, the person on the receiving end is decent enough to do what I did, inform and delete, not store and forward.


Comments (Archived):

  1. PhilipSugar

    Maybe its just me, but at a certain point, too much technology gives a worse experience.I like the feature where it waits a minute to send the email and you can take it back.I like when you type in the first several letters and it gives you all the contacts that have that.But when technology tries to “think” for me I find it intrusive. For instance the new cars that try and brake for you. No dammit I want to speed up and past that menace.If you really want to see differences in design philosophy compare Airbus and Boeing.Airbus had that plane go into the woods at the Paris airshow because the computers “thought” it should be landing instead of the pilots knowing they were doing a flyby.

    1. fredwilson

      i feel like we’ve gone too far down that path and we need more, not less, now

      1. PhilipSugar

        More is the right answer for many people. Especially those that really live technology.But I believe there is a large segment that needs less. Not back to the stone ages less, but just optimized less.I’ll give you MS Office as an example, It has just become way too complex. Of course it is protected by the huge bottom up network effect.

      2. LE

        Computer types always do “more” because they can and their brain can easily deal with it. I found this out when I had a business and used to add machines and services. I was able to comprehend immediately an extra product or service but the staff was back trying to master the last 5 products or services. What I will call “the deli menu problem”.For example if you try to learn a language (or a tool) you will find often that there are all sorts of additional ways to mess something up and potential confusion.Take as only one example the Unix tool “rsync”. -v, –verbose increase verbosity -q, –quiet suppress non-error messages –no-motd suppress daemon-mode MOTD (see caveat) -c, –checksum skip based on checksum, not mod-time & size -a, –archive archive mode; same as -rlptgoD (no -H) –no-OPTION turn off an implied OPTION (e.g. –no-D) -r, –recursive recurse into directories -R, –relative use relative path names…snip as they say(That’s the short list of command line options there are a ton more than that..)Note that they go along using a lower case letter to represent a word however when they have two words with the same letter they choose one randomly to capitalize it and one to be lower case. No chance of mistake or confusion there, right?

        1. Rick

          We have way too much technology today that is doing nothing more that wasting people’s time! I must say it again – Does the tech support you reaching your objective(s)? Or is it adding busy work?

          1. LE

            Well, many times, I typically roll my own stuff. So in my particular case I would say it definitely and absolutely does solve problems and bring opportunity.

          2. Rick

            I was being more or less abstract not really commenting on that one particular technology.

      3. ZekeV

        like we’re in an uncanny valley of automation, where the automatons crash and cause destruction in unexpected ways? but if we keep going, we get to the other side where we are served by benign, strong AI-controlled robots that are also good in bed?or, we could follow the retrocomputing cultists, and try to start all over with Lisp machines and Urbit…I’ve been reading about how old farm equipment is becoming more valuable in some markets than newer, automated versions of the same thing. b/c of the lock-in and cost of maintenance for these big systems.

        1. fredwilson

          yessssssssssssthat is so right

      4. J Nicholas Gross

        Yahoo! email already has a feature like this, but it works by whitelisting new names, not flagging potential errors; Facebook has a patent (from 2006) on vetoing potential email errors as you describe:”…determining, using a computing system, if the initial set of designated recipients for the electronic document should be modified” I don’t know if they use it yet

    2. Avi Deitcher

      Heh, do you recall when FrameMaker and Interleaf competed for word processing on Unix? I used FrameMaker, when I typed in “Interleaf”, it would auto-correct to “FrameMaker”!

    3. Jess Bachman

      I agree. It may not be a strict zero-sum game, but the advance in some areas leads to the retreat in others. Take social networks for example, we have more friends then ever, but how are the quality of our friendships and interpersonal relationships affected. It’s hard to argue that mobiel phones haven’t helped us make huge gains, but there are still some losses. Human behavior is a very complex system, and its rare where something is introduced that only has positive effects.

      1. PhilipSugar

        I agree.Could I imagine by existence (I travel a ton) without a Smartphone?? But you have to control.A big part is if you can turn off the “features”. And whether they are automatically turned on.Generalizing, but I think lots of people in tech think about new features as “cool” because they can.Also I think many of these get automatically turned on because a tech person thinks that is good for us or the company.Speaking of social networks, Facebook asked me to put in a mobile number. It said the reason was to send me a text if I got locked out. Ok, put in in. Then I was inundated by texts (I turned off). But did they say put in your mobile and we are going to start texting you?? No.

        1. Donna Brewington White

          I am wary when an app requests my mobile number esp. when it already has multiple ways to contact me. For a long time my mobile number was my last bastion of privacy but that has rapidly changed. Well, with people… I still am pretty discriminating with apps.

          1. PhilipSugar

            Yes but I reserved my kids names for gmail addresses. Somehow I don’t have the password, and the accounts are lost.

      2. Joe Cardillo

        Agree, and many technology companies are individually / collectively guilty of thinking that everything can and should scale. That’s just not possible or even a good idea.

    4. Rick

      “But when technology tries to “think” for me I find it intrusive.”.+100

      1. fredwilson

        i find it soothing

      2. Supratim Dasgupta

        Is that AI which both Elon Musk and Bill Gates have warned us about?

        1. Rick

          In most cases it’s actually AS (artificial stupidity).

          1. Supratim Dasgupta

            ASS(Artificially Stupid Systems)

    5. Cam MacRae

      That’s not exactly what happened with 296. The pilots flew below obstacle height, then exceeded the maximum nose up attitude at flight idle as they tried to avoid said obstacle having applied power too late. The computers simply sought to avoid a stall. Unfortunately the engines were ingesting tree by they time they could have produced the thrust required to go around.Still, as my Captain FIL says, “it’s a Boeing or I’m not going”.

      1. PhilipSugar

        Mmmmmm….not very clear: “A documentary on the National Geographic channel made a detailed claim that the flight recorder might have been tampered with and indicated that four seconds had been cut from the tape; this was shown by playing back a control tower tape and comparing it to the remaining tape. This indicated a problem with the aeroplane’s fly-by-wire system rather than pilot error. It is claimed that the flight data recorders had been switched and were not the original ones in the aeroplane”Somehow maybe the French might not want Airbus to look poorly.

        1. ZekeV

          That famous pilot who landed in the Hudson wrote some book about how fly-by-wire systems are prone to sudden and disastrous failure. Because they work so well MOST of the time, that pilots don’t know what to do (and have insufficient experience dealing with) a crisis where human decision-making is critical. Like if we all had self-driving cars that were perfect 99% of the time, we probably wouldn’t be as good at dealing with the 1% when we have to assume control and make split-second decisions. On the other hand, get enough nines behind the reliability, and you do get to some point of acceptable failure I suppose.

          1. Jim Ritchie

            Yep, buddy of mine is Captain at Southwest. They still believe in “stick and rudder” pilots so actually dumb down much of the Boeing auto-pilot features. They want their pilots to actually be able to fly the plane in an emergency. They have a very good safety record.

          2. PhilipSugar

            My fraternity brother is one of the chief pilots.

        2. Adam

          Hadn’t seen this before. Interesting enough, that crash was caused by human judgement and error. Not from any malfunctioning systems, so maybe we are better off with letting the machines do it?

          1. PhilipSugar

            Not clear. The PIC didn’t think so.

          2. PhilipSugar

            Airbus and France said human error. National Geographic and Pilot in Command said malfunctioning systems.

    6. ZekeV

      Yes!And this is where Google Apps keeps really annoying me. This morning I had the same auto-complete issue that Fred noticed. Fortunately I am super paranoid about auto-complete, so no harm no foul.I get the feeling increasingly with Google Apps that there is some prerogative to keep iterating on features that are already perfect. Like, it’s someone’s job to be the product manager of auto-complete, and so she spends every week trying to think of a new way to do it. This ethos results in about 10% of Google being broken for me at any given moment.Which is why I am switching all my cloud stuff to Office365. It comes with the usual painful Microsoftian cruft, but at least they care about enterprise users who need accuracy, not just power. If a MS feature is broken, it usually stays that way reliably for a few years.

    7. ShanaC

      Yes – because you feel like the technology isn’t responsive to you. There have been cases where tech was artificially slowed down because it made the tech seem more responsive. Google should go back.

      1. PhilipSugar

        Let me give a very specific example. People have tried to design robots which predict what you are going to do. One that I have funded responses in a predictable way to what you do.It kicks ass.

        1. ShanaC

          Awesome. Can I see?

      2. Shana Whitelock

        Why ? How ? When ?

      3. Donna Brewington White

        Part of good UI is striking the balance. Sometimes the bells and whistles distract from usability. I’ve had to gauge sensitivity to this in doing product management searches.

  2. Anthony Serina

    Could it have to do with the new product they launched “Inbox by gmail” or something like that? Gmail isn’t even autofilling people inside our organization properly – that is just weird. It was not like this before.

  3. pointsnfigures

    How many times have you pressed the return button and wished there was a button that could reel it back like a fishing line?

    1. fredwilson

      quite a few

      1. pointsnfigures

        me too

    2. JimHirshfield

      There’s a feature in gmail to do just that. Gives you 5 seconds to change your mind.

      1. Dan T

        I use it at least once a week

        1. Fernando Gutierrez

          I must be more careless when sending… I have to use it much more than that 🙂

    3. William Mougayar

      You can set a delay in the Settings. I have it at 30 seconds. And I do use that feature.

      1. Avi Deitcher

        I had no idea! This is a lifesaver. Thank you, William.

      2. Jess Bachman

        Indeed, this has saved my ass so many times.

      3. WA

        Excellent advice. I had no idea either.

    4. PhilipSugar

      You know I have set a policy for myself. If I am upset, I write the email and don’t send it until re-reading and editing the next day. (and I always say please lets talk, but I wanted to get my points in writing)

  4. Jeff T.

    I believe this is Gmail playing with their algorithms. Hopefully it will go back to the old way, what it was at the beginning of last week, soon. In a similar example, a few weeks ago there was a 12hr period where *all* of our company’s emails were going to spam, even when sending an email from one employee to another. Right about the same time the massive panic attack was starting, all returned to normal.

  5. andjdavies

    Yeah I find it really obtrusive – the contact recommendations rarely give me any value. But I do love the Gmail labs add-on which allows me to undo any email up to 1 minute after send. Saved me many times!

  6. JimHirshfield

    I get these all the time, but for a different reason. Our VP of Finance is also named Jim. I get some interesting emails intended for him. The worst are the unsolicited sales pitches from service providers who think they’ve successfully figured out the VP of Finance’s email address…just because the email didn’t bounce.

  7. Chimpwithcans

    Its an interesting problem when my surname is also a First name – resulted in a couple of meeting invites which were WAY above my position. Was very tempted to accept and give my 2 cents, but I went the polite receiver route.

  8. gzino

    gmail mobile upgrade rolled out to two of my Androids this wkd; perhaps related. I see the same (bad) behavior on those, one non-upgraded Android and web.especially for sharing cloud content (dropbox etc) with groups (as opposed to individuals), will it be much longer before API integrations enable us to choose a group to share with (defined by a name we give it), rather than need to type in list of emails?Ideally with a ‘group DNS’ type layer that enables us to define a group as collection of mobile numbers that can then be used by multiple mobile apps (with sufficient authentication layer)?

  9. Avi Deitcher

    Thank you, Fred (and Chris). I keep having the wrong contacts pop up. I was wondering if I had changed my settings somehow.

  10. Jess Bachman

    On more than one occasion, I have had to physically remove people from my contacts who had similar names to other people I emailed often. Or when you send email to [email protected] and he moved to, you need to make sure you remove the first contact….or bad this will invariably happen.

  11. Ronan Perceval

    Used to work so well where the first two results where the person with that name you had most recently mailed and also the person with that name you had emailed the most. If its not broke – no point fixing;)

  12. WA

    Doing what is right…even when no one is watching…

  13. Tom Labus

    who would be liable if inside info got out?

    1. PhilipSugar

      That’s the problem when the product is free.

      1. Tom Labus

        And Google has deep pockets, lawyers………

      2. LE

        I’m not sure that’s the deciding factor. The terms of the contract, even if paid, would almost certainly absolve them of liability.After all when you buy, say, an Apple computer, even though I haven’t read the “contract” I’m sure it essentially says “we guarantee absolutely nothing”.Now if you look into some kind of class action then anything is possible. But that isn’t going to get anything juicy for any single aggrieved party, right? Besides Google would have to rope a dope drag it out and defend it super vigorously otherwise it would open up a huge can of worms.

        1. Fernando Gutierrez

          And I believe Fred has said in the past that he uses the paid version of Google Apps.

          1. fredwilson

            i do

          2. LE

            I was going to comment that USV should be running it’s own mail server instead of using google for their mail but recognize that there is probably no way you will want to take the time and resources to do a project like that.

          3. fredwilson

            and it wouldn’t be any near as good

          4. LE

            Look I will say again that I know this is a non starter for you because you can satisfice with gmail quite well. But there is no question that you could have someone build a better bespoke messaging solution with exactly what you needed that would be good for you and USV. It wouldn’t be cheap. But neither is a home in LA or many things you spend money on.Imap mail and building a web client (if that is what you want to use) isn’t a mountain that a programmer can’t climb.As only one example, and maybe not the best, let’s say you had a bespoke web client (or native app) that allowed you to click one button that said “thanks” or “ok will look into it” when you saw an email. You wouldn’t even have to hit reply you could just one click. There are so many things you could do to make things more efficient if something is tailored to just what your needs are. And it doesn’t mean you couldn’t also use gmail as well (you can easily forward things to gmail if you are running your own server although what I am describing is a mail client…) Or google docs, whatever.Or doing things that would triage your email because it would be intelligent enough to learn what types of emails were more important without you having to tell it (you sort of gave an example of this with ” You would think Google would know my wife is more important. “)I think you have to stop thinking that this type of thing is a non starter when you clearly invest in many companies (in great amounts of money) that are non starters when the idea comes up.

          5. fredwilson

            i just don’t believe USV or any small business can or should build their own email or dropbox or any other such serviceit goes against my belief system to do such a thing

          6. LE

            it goes against my belief system to do such a thingThat part is fine. It is your belief system. (Like doing things using in house staff.)However on the point of USV and “small business” you are not the same with respect to messaging that the CEO of a 100 or 1000 person company is.That person isn’t managing messaging and doesn’t have the needs that you do. Not even close in a typical case.I agree with you that that person doesn’t need any system that is bespoke most likely. But in your particular case I don’t feel that way. You meet and deal with many more people (on a personal level) than the “small business” that you are referring to.If I was actually trying to “sell you” on this (and I’m not I’m just making a helpful observation) I would meet with you to determine how you use email and then propose a solution that I think would make you more efficient and solve enough problems to be worth the investment. It all starts with research and all I know is what I read on this blog that you say so I have made assumptions. (And I know that gmail is “one size fits all”..)

          7. Rick

            LE… It’s quite easy to build a custom email system. I’ve done it. The problem is again ROI. I think USV is a financial services firm not a technology firm..Many people struggle with being able to see a company’s core business. Fred doesn’t seem to be one of those people..Most importantly if someone is working email at such a speed that they can’t check the “To:” box then there is a bigger problem.

          8. Rick

            But! How much money can you save or how much more money can you make with it? That is the question!.In other words… What is the ROI for such an investment? In USV’s case, I figure, they want things they can sell to make a profit. So an in-house proprietary email system is probably not of much value to them. If it is a system that can have a business wrapped around it so that it can be IPO’ed or something then it would be of value to USV..It’s all about understanding your core business. In my view USV isn’t a technology company they are a financial or investing firm. They don’t build things they invest in them..I saw a quote from a guy on Shark Tank that said something like: I want to buy it for $4 and sell it for $4,000.

          9. LE

            Fred has a world class messaging problem. More efficiency is worth it’s weight in gold. Not about whether anyone else can be sold this same system or not. Just about making a better and more smoother running messaging “factory” if you want to call it that.Your comment, and Fred’s thoughts, remind me a bit about when I started my first business and people wanted to know why I bought the bigger faster machine. After all the smaller machine could do the same work, you’d just have to run it for twice as long. And the larger machine was more than 2x the cost of the smaller machine as well. Why? Because it’s the “right tool” for the job. And in the end when time is involved efficiency can make or break you.

          10. Fernando Gutierrez

            I agree about his problem, but I’m not sure that intellectual jobs can be optimized so much. If you make email faster, then maybe you’ll have to simply pause before opening the next one so your mind has some time to readjust.

          11. Rick

            I try to be open and honest here. Given that. I think Fred would be the best judge of whether or not an internal investment into something that *reminds* email users to check the “To:” address before clicking send is a good idea..Personally I don’t see it as being more than a couple days coding. But then you would have to take into consideration maintenance etc.

    2. LE

      While an attorney might be able to attempt a case auto suggestion is just that “auto suggestion”. The person get’s a chance to proof and if they do not the wrong thing happens. I’m sure google’s TOS wiggles out of this stuff as well.

  14. Guest

    Here’s another type of “sending stuff to the wrong people” scenario.

  15. Johanna Santos Bassetti

    Here’s another type of “sending stuff to the wrong people” scenario.

    1. Sue Wing

      this is hoax. it is the same esther and john having some offboard fun which they don’t do while in person

  16. Matt Zagaja

    In my Machine Learning for Hackers book one of the tasks involves ranking e-mail using priority inbox. From this task, which was adopted based on a paper Google published, I know that Google is analyzing these kinds of factors already (who you normally send certain kinds of e-mails to based on language/words, and also the groups of people). I wonder if it either failed to work as well as they wanted for the purpose you mention, if it freaked people out in user testing, or was too annoying?

  17. Andrew Kennedy

    I’ve been getting gmail bugs recently as well. It’s like one of those double take moments of “did i just see a bug in gmail?”

  18. William Mougayar

    I had that same reaction as Chris Dixon yesterday, and did a double take on these auto-suggestions. As if Gmail did some reset of sorts.

  19. JimHirshfield

    IMPORTANT: This comment is intended for the use of the individual recipient(s) named above and may contain information that is confidential, privileged, or unsuitable for overly sensitive persons with low self-esteem, no sense of humor, or irrational beliefs. If you are not the intended recipient, stop reading now (but feel free to upvote).

    1. Joe Cardillo

      Jim I got your comment, I am very offended and sad and disappointed in you and I hope you know how much it means to me to read your comment even though I know it wasn’t for me and hurts and now I have the feels.

      1. JimHirshfield

        I appreciate you averting your eyes to my above comment. If it’s any consolation, I greatly appreciate and deserve your upvote. So, dry your eyes; chin up.

    2. ShanaC


    3. Supratim Dasgupta


  20. jpwoodland

    Google’s in a tough spot with something like this in that many people revolt against the notion that they’re already reading the content of their emails. They’re damned if they do, damned if they don’t.

    1. Joe Cardillo

      Yes, it’s a sort of uncanny valley but for social / communication and not just androids.

  21. LE

    You would think Google would know my wife is more important. But it does not, particularly on mobile.Google doesn’t know this because they’ve stopped thinking and improving this product. It’s evergreen to them. It’s probably only a few rev’s past when Paul Buchheit wrote it (an exaggeration to make a point..)

  22. LE

    They could easily pop up a warning saying “you don’t normally send this kind of document to this person” or “you don’t normally include this person in the group you are sending this to.”Think of google as you do a car company. They don’t add features and benefits if they are already the market leader and don’t stand to gain from doing so. What do they gain (in their mind that is) if they continue to improve gmail when it seems that just about everyone is already using gmail?

  23. LE

    My hope is when I do that, the person on the receiving end is decent enough to do what I did, inform and delete, not store and forward.Well I think that depends on the person. I would probably never forward anything that wasn’t intended for me (that was sensitive that is) but being a curious person if it’s looked interesting I would probably read it depending on who sent it to me.

  24. Guest

    As a recent victim of this.I wish that they UNDO plugin in gmail gave you a preview like this attached giving you a chance to undo a mistake.The top, is how the plugin works now.The bottom is how I wish it worked.

  25. LE

    I was meaning to tell you and the Gotham Gal to watch the movie “Chef” (is on Netflix) written and directed by Jon Favreau. It’s essentially an ad for Twitter and actually has good food scenes as well.The film starts out with Favreau’s character thinking he is sending a private tweet to a movie critic but instead the tweet is public they get into a bit of a dustup…On Twitter, Carl insults Ramsey, not realizing that his reply is public, and gains a large Twitter following. Lot’s of references to twitter I’d be surprised if Twitter didn’t pay for all of that publicity.

    1. Supratim Dasgupta

      Its an awesome movie. I too felt that twitter paid for that publicity. Though it wasnt ‘in your face’

  26. pasmith

    It could be worse. Your last name could be Smith. I was one of the early active users of email while involved in the venture community for a large institution. My first email was [email protected]. You can imagine the problems that were caused as they added additional people with the same first initial. Eventually, I was able to contact the appropriate people in our systems area. They had a very simple fix. They changed my email address. Of course, it would’ve been nice if they had told me they were going to change my email address before they did it.The only way I found out my email address had been changed is that him I began getting phone calls from business associates asking why all their emails were bouncing back. This happened a number of times before I contacted our systems department and explained how important email was to me. I asked them to provide me with an email that they would not change. It was most amusing when I was asked why I had to change my businesscard every time my email address changed. “Was it really necessary to have my email address on my business card?”

  27. LE

    This really is a problem that is similar in a way to what I warn people about who don’t use .com as their domain name. Or not grabbing typos of their domain (if possible). [1]If you are using .co or .io or .whatever you stand the risk of someone addressing (by auto-completing in their brain to since you are used to chunking that on the keyboard).For that matter using an @gmail or @yahoo etc is also a problem. Someone could send something to FredWilson23@ instead of FredWilson24@[1] I own a four letter .com that is quite similar to a very famous, perhaps the most famous VC firm. Back in the 90’s when I used it for email I would get email intended for the partners of that firm. I forwarded it a few times and then simply decided to stop using the domain for email service. So now the email bounces.

    1. Fernando Gutierrez

      I understand that frustration! My twitter username is @fernando. Every time there is a Formula 1 race (Fernando Alonso) or a soccer match in which Fernando Torres plays, I get many mentions, some of them very nasty :)I also hated Lady Gaga’s song ‘Alejandro’ because it had a sentence that said something like “I’m not your babe, Fernando”. For some reason, people felt compelled to repeat that on Twitter, but with the @ before Fernando. I still get one of those once in a while.

      1. LE

        You could potentially get some nice dollars for that twitter handle btw.

        1. Fernando Gutierrez

          I have received a few messages about that, but nothing that I felt was worth exploring.

  28. Fernando Gutierrez

    I had a really funny instance of this problem 15 years ago while working for HP. There was an external contractor with my same name and lastname working inside HP in another country. External contractors had different email addresses, but in the internal address book we were all sorted by name, so I frequently got emails that were intended for him.One day I got one from a woman in his office saying how much she loved him… there was some dirty talk… and it had some pictures attached!! I know I should probably have deleted it without a word. But I could not resist the temptation. I forwarded it to him, CCed her, recommended them to have sex out of the office and to use personal email accounts. I don’t know what happened after that, but that was the last of his emails that I received.

  29. DJL

    Unfortunately, this same mistake in a corporate setting could costs millions of dollars if there is private customer data involved. I like the idea of building security and privacy “intelligence” into email. Fred – if you fund it, I’ll build it!

    1. fredwilson

      wrong, wrong, wrongif you build it, i might fund iti don’t like the “if you fund it, i will build it” askit means the entrepreneur doesn’t have conviction

      1. Richard

        Yep, the path from a one sentence pitch summary to that of a product with market fit is long and hard and VCs know it.

        1. fredwilson

          having lived it

      2. Rick

        It means the entrepreneur has experience!.What you’re wanting is to eliminate risk. Which is the right thing for an investor to do. You want David to build value that you can buy cheap. I’m liking that myself.,But there is no way to judge conviction based on David’s comments. In fact it may show more conviction because David is not foolish enough to go off and do something he knows isn’t funded properly. So he has the conviction to wait until he can land the proper funding. Just like you as a disciplined investor has the conviction to wait until there is value that can be had on the cheap.

        1. Richard

          This IS the difference between an entrepreneur and contractor.

          1. DJL

            I would propose that this is more like “internal” venture funds at large corporations. They see a market and go after it with money and talent. A “contractor” is hired to develop from specs. A person who develops an entire profitable business model around an idea is still be an entrepenur in my book. .

          2. Rick

            Again I wasn’t replying to David’s post..Fred’s statements- “if you build it, i might fund iti don’t like the “if you fund it, i will build it” askit means the entrepreneur doesn’t have conviction” – don’t have anything to do with measuring conviction..They are about Fred’s position in the business world and the approach he follows to finding investments. It’s about waiting with the purpose of eliminating risk. If you let others spend and work while you wait to see if traction is gained then you will eliminate much of the initial risk. Also it might help to make the buy in cheaper if the company in question has become weak and cash starved..I don’t know if David was offering contracting services or offering to build a business.

          3. Rick

            Oops… That was suppose to be additional info to Rich..David, did you mean you would contract the work or did you mean you would accept funding to build a business?

          4. LE

            While it is entirely possible that it’s also about eliminating risk part of that risk elimination is whether or not the person has any skin in the game and is following (maybe blindly) some idea or dream that they have had about a product or a service. Which means they will maniacally actually work on it.I’ll give you an example. I will often do a game whereby I gauge how motivated someone is to provide a product or service to me by putting up an artificial barrier or creating an artificial and made up requirement to see if they answer the question or supply the information that I’ve requested. The people who are truly motivated to do business will have no problem supplying the needed info and get back to me quickly. The people who are to busy and don’t need the business (or are just lame or triflers or lazy) will be turned off by the “assignment” and not reply or reply late if ever. Make sense?After all if you can’t get me the info I’ve requested and you haven’t gotten the sale yet, how will you be after you’ve made the sale? [1][1] That said of course people will vanish after the sale despite this in some cases.

          5. Rick

            To be on the same page we need to first define what we are talking about. If we’re talking about building a business then we are talking about the systems, processes and procedures, in place at that business. I’m under the impression that Warren Buffet has said something to this effect: He always looks for companies that have expert systems in place so that any idot can run the company. Because he figures eventually some idot will..So if we’re talking about building a company and not talking about someone holding the CEO position for self promotion purposes. Then we need to be more concerned about the company as an entity. Not the person as the Founder/CEO. We need to see that the CEO is putting in place the proper systems. We can always replace the CEO if needed..I agree that they should manically actually work on it. BUT… That, again, should entail putting together a strong company which takes resources – funding, people, buildings, computers, etc. We don’t want them putting in place “bad habits” by wanting to do everything alone which means they are not focused on building the business. They are focused on building their ego..As far as simple assignments go. If you ask for something that the company provides during the sales process then you should get it. Remember you’re dealing with an entity not just one person. So there should be no “feelings” involved with providing what you want. If you are told you will get it and you don’t then you should contact someone higher up in the company structure. If you are told they don’t provide such things during the sales process then you either should find another vendor or accept that many companies are professional companies and don’t fall for such tricks..Keep in mind that at the end of the day you want a vendor that can and will provide what you need. It’s not about testing them. You’ll have a contract. This is one of the reason’s I say companies need proper resources to be built. You can’t “play company” like people “play computer”. That’s not good business..Any sales person should be able to explain to you what you can expect for free and what you have to pay for.

          6. Rick

            I wasn’t replying to David’s post..An entrepreneur applies resources to areas of higher return. They need to have those resources before they can apply them. If they don’t have the correct resources or the right amount. An experienced entrepreneur knows not to go there.

        2. ShanaC

          why is it bad to lower risk?

          1. Rick

            It’s not bad. That’s why I said “I’m liking that myself.”

      3. DJL

        Fred – I wasn’t really serious. The point I was trying to make is that there are hundreds of great ideas that only need the intersection of capital and talent. (You aleady have the pitch for my “real” business that I have been grinding on for some time. )

        1. fredwilson

          i know, but your reply gave me an opportunity to get on a soapbox

          1. DJL

            Glad I could help. :>)

          2. PhilipSugar

            That was a great soapbox. I do the same when somebody says well if I got paid more I would do better. Wrong, wrong, wrong. If you do better I will pay you more (or you go somewhere else)

          3. LE

            I wonder if they have done any actual studies on that. My anecdotes says “agree”.What I always found was that when you pay people more they end up thinking of themselves as worth that amount of money and therefore no longer feel there is anything special about the amount of pay they are getting. On the other hand people with the right attitude tend to do a great job regardless (and as a generality) without respect to the amount of pay they are getting.In a sense this is quite similar to that mention in the Jobs book (only read part of the book) about the fence that nobody would see. Job’s father said something like “but you will know it was done correctly and that is what is important”. As you know when you hire people to do your renovations they either do quality work because they do quality work or they don’t and the amount you are paying (as long as you are being fair etc.) doesn’t really alter how they work. Your experience?

          4. Rick

            i like the ‘wrong wrong wrong’ thingie you copied from fred.copying three wrongs is still wrong ,though 🙂

          5. Rick

            Hmm… This is a perfect example of the things we need to worry about with computers. While I was asleep my computer posted comments using my name..Bad computer… Bad!

        2. ShanaC

          whats the real business

          1. DJL

            Hi Shana – We have developed a simple information security certification and SaaS software for the SMB market. Like “Quickbooks” for IT security.



        1. Rick

          Get funding because that’s how the big boys do it. That make sure you don’t commit suicide!

        2. LE

          Man in bar with ring on finger more attractive to woman than man in bar sans ring on finger.

  30. Rick

    “The thing of it is that Google is so good at knowing who you might want to send something to that they should do more than they do right now. They could easily pop up a warning saying “you don’t normally send this kind of document to this person” or “you don’t normally include this person in the group you are sending this to.””.First you say google is so good. Then you say it should pop up a warning. Which is it? Is google good enough or not?.I think you’re running yourself in circles when you should realize that the concept is bad. People don’t need a suggestion they just need the tool to make it easy for them to do their work. I’ve always said computers should only be a tool not a decision maker. Many times automation works against people!

    1. fredwilson

      i disagreemaybe i didn’t make my case well enoughsorry about that

      1. Rick

        We’ll just have to agree to disagree..People need a way to find who they are wanting. Not a suggestion based on what character’s they’ve typed in. The concept is wrong. It’s a very old paradigm that comes from a combo box implementation done decades ago. It needs to be re-thunk!

  31. William Mougayar

    There’s another twist on this theme. People leaving their screen share ON after a session, and then revealing their Inbox etc… One of out 3 times, I’ve had to remind them to shut if off. “Hey you left your screen share on.”

    1. Supratim Dasgupta

      Happened to me quite a few times until the poor wifi connection cut it off.

  32. LE

    Actual illustration of the issue of email sent to the wrong domain which I discussed in another comment. Note the time period and how many mails messages are being bounced that could, if wanted, be intercepted. (Screen grab attached, click to enlarge)

  33. Kevin Williams

    There is an exception to the last point of “inform and delete, not store and forward”- I had a “business intelligence” firm accidentally forward their detailed plan (in .ppt!) to approach me and other leaders of a start-up under a clever academic pretense to attempt to dislodge some proprietary information for a clearly named Fortune 500 client. Turns out their key account rep was also a “Kevin” and my email autocompleted before his… Oops. *That* email was forwarded to every colleague targeted in the brief.

  34. Menachem

    I’ve noticed that Gmail stopped suggesting the most emailed users on Friday. Usually when I start typing “David,” a specific David always comes first because I email him the most.Since Friday, it’s just putting random Davids there. This happens with any name. Since I’ve noticed, I’m just being extra careful.

  35. hypermark

    I think this underscores the basic truth that more we automate “intelligence,” the less people reflexively think when they click SEND, making it all the more critical that our systems have a “DO NO HARM” throttle.Case in point, a week or so back, I got accidentally added to a vendor’s internal discussion on a different client. As this was a thread with 5 or 6 people on it, I was exposed to no less than ten back and forths over the course of a few days. While the thread was nominally embarrassing, in the wrong hands or with a wrong comment or two, it could have been disastrous.It’s a bit analogous to the “Land of Confusion” video a few years back by Genesis where Reagan wakes up from a nightmare trying to click the button to call up his Nurse, but instead clicks the Nuke button.

  36. Robert Heiblim

    Yes, I have experienced incorrect suggestions from Gmail since they started this. Means sitting back and taking a bit of time to review for correctness. A bit of contemplation prior to hitting send is often good.

  37. Brandon G. Donnelly

    been noticing this over the past few days with gmail as well. i thought it was just me.

  38. panterosa,

    Need better pattern recognition.Which is why I build tools to teach that. Intelligence = pattern recognition.

  39. Dave W Baldwin

    Taking a guess, I’d say Google is changing and has overflow. A lot of what pops up doesn’t make sense. I had a nightmare last week getting things ready for a convention.

  40. Ryan the Jenks

    Why do we still not have a good retractable solution? If you sent a message to the wrong person, you should be able to delete the message.

    1. JoeK

      If you know that it is the wrong person, don’t send them the message. If you don’t know that it is the wrong person, then neither can a software tool. Being able to ‘delete’ a sent message is no different from being able to ‘unsend’ a delivered parcel. As a simple example, when I purchase an airline tickets online (from Shadywings Inc), do I want Shadywings Inc to be able to ‘delete’ the ticket confirmation email, from my inbox (whether I have read it or not), so that they can sell the ticket to someone else? Or for your obsessive stalker to send you threatening emails at night that they can ‘delete’ as soon as you have read them?

  41. Donna Brewington White

    “I have always depended on the kindness of strangers.” — Blanche DuBois (A Streetcar Named Desire)I find this to be true even more so in a digital world.

    1. ShanaC

      I think we all do. I think this is how we all end up stop being strangers. We are all strangers in a strange land.

      1. Supratim Dasgupta

        “”I think this is how we all end up stop being strangers. We are all strangers in a strange land.”” Quite a powerful philosophical line! Original?

        1. ShanaC

          The last part I’m Playing on biblical language involving the redemption in Egypt. But otherwise original

          1. Supratim Dasgupta

            Nice!! I like it!

  42. Varadappa Rajan

    Isn’t that facebook all about ? I still read the comments posted by a russian women to her boyfriend in new zealand, thanks to a mutual friend who I worked with some 15 years ago and happened to accept the connection invite. And by the way, the russian and zealander are planning to take a trip to Maldives in about 2 months, just so if you are curious on the latest updates.

  43. Ben

    i’ve seen a variant of this for months, which is that gmail picks the wrong address for the right person. i have friends who have multiple email addresses. whenever i try to send them an email, i type in their name and it always autocompletes to an address i seldom use. i’ve even typed in the exact email address instead of the person’s name and google does no autocomplete on the frequently used email address. its autocomplete used to work very well but several months ago it stopped working well for me.

  44. Tom Labus

    David Karp on CNBC getting beat up over Net Neutrality. Some one stronger needs to make the case and correct the hosts who are completley on the carrier’s side.

  45. daryn

    whoa, I thought I was just going crazy 🙂 There are two new people in our office whose names keep auto-correcting to different people’s email addresses (people with very different names). Didn’t even think that gmail would be having such a terrible bug!

  46. John

    There’s a Gmail labs that will analyze your email to see if you say the word attach (maybe some variations) and warn you before you send it if you haven’t attached a document. That’s saved me many times. Similar concept to what you described.I also noticed the change in suggestions. The problem with improving those suggestions is that we also have built in habits. So, if the suggestions change too much, it might break our habit of typing a certain thing to get a certain person.What I don’t get is why the To: box in gmail is different than the search box at the top. I wish it used the same technology, because sometimes I can’t find an email in the To box, so I use the search box at the top and easily find the email I’m looking for.

  47. Sue Wing

    OMG, can’t believe you were going wrong countless number of times before correcting yourself each time. Incredible