Telling Like It Is

I told a Rob Kalin story yesterday and I am going to start this post with another one. When Rob left Etsy for the second time, it fell to me to tell everyone what was happening at the company’s all hands meeting. I asked Rob what he wanted me to tell the several hundred employees who would assemble to hear the news. Often there is a story concocted about the founder or CEO wanting to step back, take more time with their family, needing a break, etc. And so I wanted Rob to tell me how he wanted this story told.

Rob said “Tell them you fired me. They will know anyway. You might as well tell them the truth.” So that’s what I did, with empathy, respect, and appreciation for Rob and his work. It went well. The team was happy that I was being straight with them. I then handed the stage to Chad who took it from there and has been doing a great job ever since.

I don’t tell that story to bring up old unhappy times. Although it may for some. I tell it because Rob had the courage to allow me to tell it like it is.

And yesterday Chris Poole told it like it is. With a blog post that is simple, honest, and sad. He made the decision that our portfolio company Canvas has failed. Running out of money is always the thing that brings this moment of reality. But so often an acquihire is arranged, or the company is put on mothballs, or you just stop hearing about the company. The story of failure is buried.

I prefer the way Chris did it. We tried, it didn’t work, we failed.

The truth is, as Chris explained in his post, that the first product Canvas was a failure. The pivot to DrawQuest came too late, took too long, and now DrawQuest is a succeeding product inside a failing company. I know that Chris is going to try to find a way to keep DrawQuest going. It’s got 400,000 people who use it every month and 25,000 people who use it every day. But it has not monetized particularly well and the Company hasn’t found a good way to inject virality into the product so it can spread without expensive marketing dollars. If you know of a good home or a good steward for DrawQuest, email me. There is a contact link in the footer of this blog that will send me an email.

Chris says he is going to blog about the things he learned from this experience. Chris hates writing. But I think he will do this, as therapy for him, and as a post mortem for him and everyone else. So pay attention to his blog, subscribe to his RSS, or follow it on Tumblr.

Like his post yesterday, I expect Chris will continue to tell it like it is.


Comments (Archived):

  1. falicon

    I’m a big believer in telling it like it is and really liked how Chris did this as well.I took this same approach when I shut down Statsfeed and when I shut down Knowabout It…neither was venture backed but both had significant personal time/money involved (and at least some acquihire interest).Both times it was *very* painful getting to that point…but eventually you reach a pull the bandaid off moment and then once you do it, the world immediately feels like a better and happier place.Still – I hope I *never* have to do it again…

    1. fredwilson

      so many things are like that. removing a bad hire is like that too.

  2. pointsnfigures

    Howard Cosell would be proud.I read that post yesterday about Canvas yesterday and appreciated it. There have been other companies that have exposed their failure. For entrepreneurs this is a good thing. First, it can be cleansing for the ones that failed (as you point out) Second, for anyone deciding whether to trod down the path of a startup, it helps them think about risk/reward in a more concrete probability based way. Going into it with eyes open understanding more about what needs to be done should cause less failure.Hope they find a way.

    1. fredwilson

      an entrepreneur asked me yesterday what kind of stats would allow a company with a mobile app to get funded.i said at least 50,000 daily activesand he said “are you nuts? if you can get to 25,000 daily actives, you are off to the races”and then i thought about drawquest and its 25,000 users who come back day after day after dayand i said, “not really”there is a warped sense of what success is out there in the world of startups and its not healthy

      1. falicon

        Amen.I talk to a lot of people building things at a lot of different stages…every single one of them has a different definition for “what’s working”…and MASSIVE confusion on just what “product/market fit” means.Part of the problem is that very few companies take the time to go back and share the real milestones they were hitting along the way…and even if they did, yesterday’s bar for ‘working’ is 10x today…just the nature of the industry I guess.

      2. William Mougayar

        Exactly, and you already wrote that Traction doesn’t mean Product-Market fit.There has to be alignment along 3 paths: Traction, PM Fit, and (sustainable) Business Model validation.

        1. awaldstein

          I’m going to keep asking this.Business model validation examples for startups (not Apple, Google, game companies)?I may have one in mind but still in stealth but the list is very small, yet the # of startups huge.

          1. William Mougayar

            when growth is steady and it’s accompanied by revenue growth, that’s it. they know it.but maybe where you’re going is…there are business models that have the appearance of success, but their weakness is they plateau at a certain revenue level. then success becomes relative: either the market isn’t big enough, or they need some leapfrogging where incrementalism didn’t cut it, or it could be other reasons, e.g. marketing related perhaps. it’s tough to generalize.

      3. Richard

        In previous blogs you spoke about back of the envelope income statement projections of about 100k per engineer per year. Is there a number for the cost per MAU (not acquisition but server overhead) ?

      4. Kirsten Lambertsen

        Makes me think of the 20K party scene in “Girls.”

      5. markslater

        and in mobile it is getting exponentially harder.

      6. Donna Brewington White

        What needs to happen to change this perception?

      7. ShanaC

        there is too much money out there because angel money is getting better returns than the stock market…(and definitely better than the risk free rate)

  3. Robert Holtz

    Impressive story. Now, whenever I think of Rob Kalin, I won’t think “Etsy”… I’ll think “Gutsy.”

    1. fredwilson

      he is that and much more

  4. Richard

    Thanks for this post. It is often overlooked that the VC (via its power as a board member) has a fiduciary responsibility to its limited partners to make this type of decision.

    1. fredwilson

      we did not make this decision. Chris did. it is true that i told him it would be very hard for USV or any of the other investors to put more money into the company on its current trajectory. but he could have pushed it. he made the call to wind things down.

      1. Adrian Bye

        sounds to me like he made the right decision. its a terrible feeling that “success is just around the corner”, when it isn’t. go big or go home!

  5. William Mougayar

    It’s weird that since 90% of startups fail (one way or the other), we always hear about the successful ones, and not enough about lessons learned from the ones that didn’t make it. Arguably, the lessons of failure are more important than the lessons of success, because you often need to avoid a lot of mistakes in order to succeed.This reminded me of a post you wrote a few months ago, Revenue Traction Doesn’t Mean Market Success…Since closing Engagio, I’ve been blogging citing indirectly the lessons I learned, but not as openly or directly. It’s not that easy. But here’s a curated collection about failing and lessons from it, via the Startup Management library:http://startupmanagement.or

    1. JamesHRH

      Its media issue, in a way.People who are just grazing eyeballs (the Bored @ Work market, as Mark Cuban calls it) want the tantalizing stories of insane success or abject failure.@moot isn’t an abject failure, as someone like Jerry C can attest. Canvas isn’t an abject failure either.But people who are passing the time on upworthy aren’t up for learning, just mind candy.

    2. Elia Freedman

      I’ve managed to keep Infinity Softworks going for 17 years now but I am probably in the last year of it being a full-time endeavor. We are working on something new, finally hope to launch next month, and suspect it will either be successful and spun out into a new entity or the entire endeavor will be nice income but not great and become part-time.We had a number of fail points though. I feel strongly that to move on and even be able to think about the new ideas I had to come to terms with these failures. I’ve done that publicly on my blog — both personal and other’s accounts — but not certain that’s required. I am positive that I wouldn’t be working on the exciting new thing if it wasn’t for understanding the successes and failures if the old.

      1. matthughes

        Excited to hear more about the new venture.

    3. Jordan Thaeler

      Sometimes. More often than not, the major successes you hear about are just luck. I guess a lot of business success can be tied to luck: mainly timing. Timing of the macro markets, the financial markets, technology development, etc. It would have been nearly impossible for Facebook to fail. People were signing themselves up. No sales needed. Just keep a platform up so people can scale it themselves. Likewise with Snapchat. Do the frat founders know anything more about running a business than Yahoo’d former COO de Casto? I think not. And an astute outsider would have bet on de Castro and been wrong. Which is what makes venture capital so tough, and why most VCs are really just growth equity investments now. Bet on the sure thing.

      1. William Mougayar

        True that luck and timing are important factors.

        1. Richard

          Truck of Luck

      2. LE

        Business is about being able to “execute and take advantage of the low hanging fruit of opportunity.” [1]If that low hanging fruit doesn’t exist you can bang your head against the wall and nothing will happen. I guess this is a variation of a cliche “a rising tide floats all boats”.This is why it can be a waste of time to read all this shit about what other people did. Not that you can’t glean something from it (I can certainly teach people some cool moves like anyone can) but all in all there are parts of the puzzle that can’t be duplicated. It’s not science it’s not computer programming.[1] My saying which I take full credit for.

  6. awaldstein

    Two reactions:-25K uniques a day not enough! Success is a stratospheric # is seems for mobile.-Loved the unvarnished truth. 99.9% of those in similar situations opt for a soft landing story. Many lauding it today will I bet have chosen this path. It’s just easier.

    1. falicon

      It’s not just about the uniques…it’s about the revenue plan.If you only have 10 uniques a day, but each is earning you 10k then you are golden…trouble is that very few people have figured out a ‘venture worthy’ way to make money via mobile yet.You can make good money with mobile apps…but it’s not clear that you can build a real, and large, business via just mobile yet…the majority of wins so far feel like “hit driven” stories…

      1. awaldstein

        I understand that.Then why if there are 50K is it doable and at 25K not? This is not about a plan it is about scale. Not the same thing in my book.

        1. falicon

          I don’t think 50k means anything either (it might get the conversation going, but they’ll dig into more important things before a deal would get done).I think it’s really more about the speed and rate of growth when you are talking about uniques…but even still, I don’t think it’s a very good metric to focus on (unless your business model is proven to be tied directly to that metic [and working]).

          1. awaldstein

            Examples of a or a few mobile business models that work then.If the absolute numbers aren’t it, then growth is irrelevant as well.

          2. fredwilson

            here’s a few mobile business models that work- be apple, tax the market 30%- be google, use the phone as a trojan horse for your services- be twitter or facebook and lead the market into native mobile ad formats – be candycrush – make games that are more addictive than crack and make users pay for more when they run outthe sad truth about mobile is that there aren’t as many models that work at scale, but the ones that do work work incredibly well

          3. awaldstein

            ThanksI had Apple, Google, FB on my list but damn–it’s a short list and only the top of the chain survive.Not great odds and huge guts to go after for investor and entrepreneur. Go big or go home crosses the line from investing to gambling to me in many ways.

          4. falicon

            That was my point – not a lot of proven or repeatable models yet…I would argue the only ‘repeatable’ one so far has been the “hit driven” like that of the video game or movie industry.Part of the fun of an early industry though…it’s the wild west and everyone is still trying to figure out what the rules should be and how the game can best be played…

          5. awaldstein

            Pre mobile, there was (almost) always a way to translate usage and attention into dollars.That’s the change and the challenge.

          6. falicon

            Yep.The advertising model of days past is not translating well to mobile for many reasons…which means it’s time for some of us to do the “real work” and figure out model will work…

          7. markslater

            The model is a PPC API model. I’ll post a link shortly to a white paper on the future of PPC on mobile.

          8. falicon

            What is PPC? Price per click? Price per customer? Pay per capture? Pray people care?Regardless…very interested to read the white paper you mention.Here’s what I know about mobile so far:1. It’s rapidly reaching *everyone*.2. You have seriously limited ‘in-app’ attention from most people. They may go back to the app many many times throughout the day, but they aren’t spending a large amount of time ‘hanging out’ once they are there.**This might simply be a side effect of not having solved enough *serious* problems with mobile yet…3. Partially because of #2 People currently prefer *very* specific and focused experiences (the OS is the portal).4. Combine #2 and #3 and you realize that the only models that can possibly work have to be in-line with the intent/use of the app (hence the ‘native’ mantra).5. Distractions to the core intent/use of the app (advertising being a big example) will not generate serious revenue *and* will seriously hinder engagement and growth.

          9. markslater

            whats your email – i’ll send you a copy in PDF

          10. falicon

            Thanks! My email is info at falicon dot com

          11. markslater

            and you are bang on the mark.Apps need to act like remote control devices. Native, Quick, focused.with PPC i was referring to the wildly successful Pay Per Click model on the web – that wont translate to mobile in its current form.

          12. markslater

            absolutely correct arnold – this is the challenge for sure.

          13. Brandon Kessler

            I’d love to see a blog post from you expanding on this comment alone. Much here for folks to discuss.

          14. Aaron Klein

            Incredibly valuable comment for those thinking about mobile. I’ll add one more to it.Provide “magic button” value that drives a transactional service. It’s sort of like “native ads” but you might call it “native revenue.”

          15. awaldstein

            Care to expand on this?

          16. Aaron Klein

            Uber is a terrific example. We’ve got a plan for Riskalyze down the road that could be another.Yes, you’ve got to have 50K uniques for a VC to take a bet on you building out some kind of monetization strategy for free users.I’d argue that if you can provide real value, and deliver it through the sensors and reach of mobile, transactional apps can break through with far fewer uniques at the beginning.At the end of the day…I would have saved a lot of time with Riskalyze if I had ignored the tech scene’s free user + monetization game, and focused on building a business #PoweredbyRevenue.Not saying it’s not a good game to play — Fred has built some great businesses that way. But there are other ways to build great value on mobile.

          17. awaldstein

            Agree–just wanted to hear you articulate it.I’m working with ones on both sides of this and agree, it can be done.Also, there are some dual web and mobile solutions that are a smart hedge and bringing value to where the customer is today that make sense.

          18. Aaron Klein

            +1. It’s been interesting in our current position because I’ve come to the strong belief that native mobile is a 100X better experience than mobile web.And yet, all I’m shipping is mobile web, because that actually is doing a better job of fulfilling what my particular customer base wants from mobile.

          19. awaldstein

            Iterating on a native mobile app is a huge challenge. Smart and I buy this strategy for you.

          20. Aaron Klein

            Absolutely true.We’ve thought about doing mobile apps and we aren’t scared of them at all, but the clients of our advisors just get a simple questionnaire by email and they don’t want to have to install a new app to respond. A simple tap on the email gives them a mobile web questionnaire that they can quickly and easily answer.Thinking through the actual use cases and length of usage that you’re looking for can quickly expose that mobile web is actually superior to native app because of install hassle.

          21. markslater

            we talk about this magic button here in wired…i am absolutely convinced that this is a huge opportunity.My CTO is publishing an article on how the magic button will transform the PPC model with an API. Mobile is API thats what we have concluded.

          22. Aaron Klein


          23. William Mougayar

            What category is Kik in? i’m curious what the revenue model is, eventually.

          24. jason wright

            android will mutate and turn on its creator.

          25. LE

            “use the phone as a trojan horse”Isn’t it odd that the “brand” used the name “trojan” for their rubbers?As if the woman (or I guess, um, for some people the man) don’t see what is hiding behind the plastic? “Oh, wow a penis is there I was fooled”.

    2. ShanaC

      35k is enough without venture money, but they wouldn’t have gotten the 25k without venture money is near impossible.

  7. laurie kalmanson


  8. Rohan

    It helps when you’re able to tell it like it is. That way, you learn to see it as it is and not as you would like it to be – which I think is really valuable.

  9. JimHirshfield

    It’s been 13 years since I failed and had to wind down my startup. It still hurts to think about it and think about what I could have done differently. But I remind myself that 2000 was a very different time than the current one we live in; different cost structures, less acceptance of failure, and of course, post-dot-bomb apocalypse.

    1. fredwilson

      2000 was awful

      1. JimHirshfield

        RIP 2000…and all my equity.

        1. pointsnfigures

          2008 was no walk in the park either….

          1. markslater

            i win. I was at CMGi in 2000. 😉

          2. JimHirshfield

            my condolences

          3. Cynthia Schames

            2000, 2001, 2002 were all a disaster. I worked at CMGI during that period too, plus 2 VC backed startups, both of which fired me/laid me off. That’s how I ended up starting my first company. Which didn’t fail. So: bright side, lessons learned.

    2. awaldstein

      You forced me to look back.Advisory and investments aside, in ones I was founder or in first 10 employees, looks like: 5 that were variations of a soft landing, 2 went public, 2 successful public turnarounds and 2 ongoing.

      1. fredwilson

        better distribution of outcomes than most VCs, including me

        1. awaldstein

          Been lucky Fred and honestly, my career chose me and it’s been a good one so far and still going,

    3. Kirsten Lambertsen

      I lost my net worth in one day in 2000. But I was too young to let it worry me. Would love to have it back now!

      1. JimHirshfield

        I feel yer pain.

  10. Jess Bachman

    Well I am excited to see what Chris comes up with next, assuming he does. He is a unique talent and I think the internet needs him in the space right now.

  11. JamesHRH

    Its Be a Grownup Week on AVC.Kudos to Rob.

    1. fredwilson

      And he’s been front and center in it

      1. JamesHRH

        Monday he was Interesting. Tuesday he was Impressive.That’s a rare double.

  12. Benjamin Yoskovitz

    For me, the best quote from Chris Poole’s post was this:”Few in business will know the pain of what it means to fail as a venture-backed CEO. Not only do you fail your employees, your customers, and yourself, but you also fail your investors—partners who helped you bring your idea to life.”Until you’ve been the CEO, the last guy in the office literally turning the lights out, when everyone else is gone, you just can’t know how it feels. I wrote a post reflecting on Chris’s comment today (http://www.instigatorblog.c… — “Welcome to the club.”

    1. LE

      Certainly much better to fail with someone else’s money and to be able to say you failed at a VC funded startup then to fail in the IRL business world with your own (or families) money where failure is definitely with no question about it – failure.And not failure that earns you a badge of courage and a place on the startup map and some partial fame. In other words better to have flunked out of Harvard than get an actual degree from a community college.Some of this reminds me a bit of when a celebrity gets cancer. Of course it’s terrible for anyone but it’s much worse to be a schnook in Staten Island living by yourself to get cancer than someone the Dr.’s and nurses are all going to fawn over. (If you’ve read “House of God” in other words a “gomer”).

      1. Benjamin Yoskovitz

        No one gave me a badge when I failed. There was no cheering or celebrating. It was me, sitting in an empty office, with the lights out. Still had a roof over my head, food to eat and a loving wife, but it sucked a lot.Taking family money and losing is worse, I agree with that. But I don’t think the VC funded world isn’t real life 🙂 It felt pretty real to me.

        1. LE

          IRL isn’t the best way to term what I meant I guess.I mean the world before the funny money of the internet.The vast majority of people who start business are not in the startup scene and in many cases they are risking their own money.Of course failure hurts no matter what. Because it’s a psychological thing. Even a person with a rich family to fall back on will feel that pain. In many cases because they have something to fall back on that may very well be the reason they took the risk in the first place.

  13. Tom Labus

    It hurts, a lot

  14. Brandon Burns

    I feel like I died along with the company. So sad. Especially considering that the pivot got it “right,” but not in enough time. Just another lesson in why its important to make bold decisions and make the quick.Growing up, my mom’s favorite bible verse to quote was Mark 9:47. “If your eye causes you to stumble, pluck it out. It is better for you to enter the promised land with one eye than to have two eyes and be thrown into hell.” Take out the religious undertone, and you still get the point: if something’s not working, no matter how much it is apart of you, get rid of it and move on.

    1. Cynthia Schames

      It’s so true that you have to be willing to “kill your baby”. I’m right in the middle of that, and it’s scary and sometimes painful, but it’s the right thing to do. And it’s less scary and painful than regret. Just grab hold of whatever gives you courage, and jump into the abyss.

  15. reece

    read, and appreciated Chris’ post yesterdayhuge props to him for ‘telling it like it is’

  16. SDB

    Some great topics this week. As someone mentioned, this has been a “growing up lesson” week at AVC. While we are there, any good lessons about co-founders staying on good terms through acquisition process, after acquisition, and while part of the new co?

  17. Sebastien Latapie

    Honesty and truth are admirable traits, and will lead to being seen with respect and trust. It’s incredibly hard to share failures, but there are many lessons to be learned. Chris’s post reminds me of James Altucher who does a great job of being completely honest and open which has led to some great stories and helpful advice:

  18. Kevin OKeefe

    Another founder who blogged about his struggles, and, ultimately, failure was Ev Williams at Odeo. I learned from Ev’s transparency and Ev certainly did pretty well with Twitter, an offshoot of Odeo.

  19. matthughes

    That’s crummy news for the Canvas team but no doubt, better days are ahead.

  20. Harry Glaser

    I’m curious how the possibility of an acquihire plays into all of this.As an entrepreneur, I admire the integrity & honesty of Chris’s approach. That said, in this situation, I would feel an obligation to my employees & investors who made sacrifices and took risks to back our adventure, if that is what they want.As an investor, would you encourage entrepreneurs in this situation to take acquihires if they’re available?

    1. fredwilson

      It depends. I need to write a post about that

      1. Harry Glaser

        Please do – I would love to read that post.In that situation, I generally wouldn’t want to go work at most acquirers, but I think I’d feel honor-bound to salvage a modicum of financial return for my investors. So I’m very curious about the investor’s perspective.

      2. Anne Libby

        I’d love to see a post on acquihires, period. It’s easy to see the exit side of things, but I wonder how often the acquirers retain the bulk of the team for any period of time.

  21. PhilipSugar

    You know what would be a great USV event? One where we get some entrepreneurs together and only talk about times we got kicked in the teeth. No pussy footing around, no sugar coating (pardon the pun), but unadulterated stories of when you got your dick knocked in the dirt.People sometimes say I should do stand-up (I don’t think so) but I know when I start telling stories about terrible failures people howl.Nobody ever does it, but you only know you are real if you can. I used to live next door to a super nice guy that happened to be an ex-Pagan and owned most of the coin operated machines in the tri-state region. He was a tough dude. One time I had a party at my house and he was talking about fighting and I said: So Rob: I hear you you are a tough guy, but tell me about the times you got your ass kicked. He had so many stories we were literally crying.

    1. panterosa,

      Love this idea! Can I come?

      1. LE

        What part of “when you got your dick knocked in the dirt.” didn’t you understand?You can come and serve the food and clean up afterwords if you want though. Just don’t interrupt the men.Note: The above is my attempt at humor. I really hate that I have to soften the joke by saying that. I think the 2nd paragraph I just added allows me to strike the note.By the way (Phil) that’s why I want to be a standup comic. Or write a fiction book or make a movie. Because that way I can say what I want because there is a difference apparently between saying something IRL and saying something which is cloaked in creativity.

        1. Tyler Hayes

          I tried to upvote this twice but the system just kept saying “Not necessary. We know this guy.”

        2. PhilipSugar

          No I really shouldn’t use that language here.

          1. LE

            But I appreciate the opportunity to crack a joke so I’m glad you did say that.

          2. panterosa,

            I never heard the phrase. The image is quite unsettling! And as LE points out, I ain’t even got one!

    2. ShanaC

      there was founders @ fail for a bit. But it wasn’t great…

    3. JamesHRH

      I could do a set at that gig.

    4. bsoist

      You certainly got me laughing when we met. 🙂

      1. PhilipSugar

        That’s the exact point. Totally forgot what I said.

        1. bsoist

          I don’t remember exactly what was so funny, but we did talk about a company you started not far from where I am living now. I think you said you still drive up almost to my place frequently.BTW, I’ve heard people say that everyone should try to do standup. It’s so hard to do, it’s supposed to be like therapy or something.

    5. sachmo

      I think that’s a great idea for a USV event. Give enough notice, I’d be there for sure.

  22. panterosa,

    “Radical Transparency” is what caught my attention. It takes some serious cojones to do that outwardly, and it’s vital to having one’s own perspective inwardly.Good Luck on next steps and stay brave, an achievement in itself.

  23. SD

    Most people, particularly in the tech community, see failure as a necessary step to achieve success. Telling it like it is can be useful in exorcising the demons, and eliminating ambiguity. Telling it as it is can be the way to move on to the next thingBut I think what sometimes gets lost in the discussion is the corrosive impact failure can have on ones self confidence.Having failed in my most recent project, I can attest to this. Even if people don’t see me differently, I feel like they do. I play back every step from inception to demise, and often it is hard to avoid the thought: “how could I have EVER thought this was a good idea?” And every critique of the original idea becomes more resonant.At least for me, it becomes harder to trust my own instincts…the naysayers were right last time, why won’t they be right the next? At least for now, this has led to paralysis. I’ll break through eventually, because I have no other choice. But in this process of embracing failure, lets not forget how painful failure actually can be.

    1. LE

      it becomes harder to trust my own instincts…the naysayers were right last time, why won’t they be right the next? At least for now, this has led to paralysis. I’ll break through eventually, because I have no other choice.Impossible without knowing what your idea was, and the particulars to determine if they were right or not.Obviously the big boys have some really spectacular failures. And so do VC’s and angels. Rarely is there an idea that comes along that everyone agrees is a winner (or, and I think as Paul Graham has said, “someone would have already done it”).What you want to avoid is a stupid idea that is easy for people to tell you why it won’t work. Probably best to think really hard about that one. And listen to what they have to say and know why you think they are wrong. Then it might be worth a gamble. Sometimes you can still make it work though (I did). Simply because people who know are jaded in their perspective.Knowing a bit about business (and particularly this business) I immediately realized that Phil Kaplan “pud” (adbrite and fucked company) [1] [2] idea of tweetname (where you can register a domain by using twitter) wasn’t going to fly. And it didn’t. Kaplan didn’t understand the market and mistook a need he had for something that would be good for the others who register domain names.Yet Kaplan was a big success with other things.[1]…[2]

  24. Amar

    There were two really strong and honest exit blog posts yesterday. Canvas was one of, the other was outboxmail (

  25. Antoine

    I have been faithfully following the AVC blog for the past 7 or 8 years now and I have always been impressed by the quality of the posts. However, the past two stories – “You are not your work” and this one “Telling it like it is” – are truly powerful. They are sharp, sincere, thoughtful. Based on real life experience, not just high level concepts, those stories certainly feel very personal and I can relate closely to them.Thank you very much.

    1. fredwilson

      Thanks for saying that. I’ve been getting a lot of sleep lately. Maybe that is why

  26. Semil Shah

    I loved this post so much. Why, I wondered, did everyone stop to read this? I think it’s because we are so blinded by people puffing themselves up, something like this cuts through all the noise and touches us. We know what it feels like. My hope is Chris’ writing helps change the conversation here, and helps people realize that even good, growing products may have to face the music if certain things (revenue, virality, investment rationale) aren’t in place.

  27. Twain Twain

    What would be great is an online db of founders and team members who’ve previously failed in one of the 90% of startups that fail.In lots of ways they’re good future co-founders because their hands are calloused and their souls weather-beaten and resilient from their experiences.Sure, they didn’t make it to the top of the rarefied air of the top of the Himalayas but they know what life is like at base camp and that’s valuable knowhow.

  28. Brad Lindenberg

    I’m loving this new movement of discussing failure in detail – Everpix et al. I think someone should start a “Crunchbase” for failed start-ups so we can learn what went on. There is way more to learn from this sharing of experience than there is from sharing vanity numbers on TechCrunch. Great post Fred.

    1. LE

      There was back in the day.…In any case the history you read about the failed companies will be about as accurate as the history and stories you read about the successful ones.Like with the saying about advertising “50% is lost you just don’t know which 50%” (Wanamaker said that).It would be interesting and entertaining no doubt. But as far as accuracy surely lacking.

  29. jason wright

    better to have loved and lost than to have never loved at all.better to have tried and failed…

  30. Jan Schultink

    Related: American culture is relatively indirect and careful in the way things are said, as a non-American doing business across the ocean I need to adjust:1) Input: interpret weak signals/feedback that could point at a huge issue2) Output: watch out with language that can come across brutal (especially jokes in the absence of a face-to-face connection)

  31. Jose Aberg

    I feel tremendous admiration for all entrepreneurs, but specially for those who have the strength and courage to admit failure. I thank you Fred and Chris for sharing this post. I wish we could read more about failure. It would help wanabe entrenpreneurs like myself to be more preapred for the worst. Thank you.

  32. JimHirshfield

    Someday. When are you in NYC next?

  33. PhilipSugar

    I’ll host and start off the festivities.

  34. panterosa,

    Can we call it SuperFail?

  35. ShanaC

    How did you figure out forgiveness?

  36. ShanaC


  37. Cynthia Schames

    Charlie, that is powerful stuff. Thank you.