Talking About Failure

Startups fail. That’s part of the natural entrepreneurial cycle.

A great post is making the rounds from an entrepreneur who has 30 days left before he hits the wall. His blog – My Startup has 30 Days to Live – promises to be a powerful one, at least for 30 days. I’m only sad about two things: (1)  It’s anonymous and (2) There are no comments so it’s one way.

I left a message on “Ask me anything” asking him/her to reach out if I can help. We’ll see if he/she responds – or it’s either (a) a one way rant or (b) a fake failure story.

Either way, entrepreneurs need to talk about failure. It’s fine – I’ve failed at a ton of things. On Monday, I gave my “How To Fail” talk at Techstars Boulder. Included were all the Startup Summer students as well as a bunch of members of the Entrepreneurs Foundation of Colorado. I told the story of my first failure (my first company – Martingale Software) and my biggest failure (Interliant). I made some broad points and then did an hour of Q&A.

I hope it was useful.

I see entrepreneurs, especially first time entrepreneurs, in denial all the time about the possibility of failure. “Failure is not an option”, or “I’m afraid to fail”, or “Everything is going great” (when it isn’t). Sometimes failure is your best option.

Denial of reality – and what you can do – is a big issue. Ignoring reality until it’s too late is another. Not reaching out for help when there is still time is yet another. Fear of failure – which is the mind killer  – is yet another.

In one of my darkest moments of Interliant, I was sitting hunched over at the kitchen table of one of my co-founder’s (Len Fassler) – breakfast table. We had a brutal day in front of us and I was waiting for him to finish getting dressed so we could head to the office to deal with things. When he came into the kitchen, he saw me and said “C’mon Brad – suit up – let’s go.” He patted me on the back in the wonderful way he always does and said “Just remember – they can’t kill you and they can’t eat you.”

Follow My Startup has 30 Days to Live. Learn from it. And if the entrepreneur uncloaks, let’s try to help, even if it’s just providing emotional support.

  • triciatita

    How do you embrace failure? When you are looking failure right in the eye it feels nearly impossible to embrace it and accept it… You have been raising your startup since birth and to be able to accept the fact that its just not going to work out or its beyond saving takes a lifetime of understanding. Especially for young entrepreneurs who are so passionate and determined and believe that nothing can stop them, being able to see beyond your failure or accept the fact that it just won’t happen is something of great maturity in the startup world.

    • André Thénot

      It’s a tough question. There’s a fine line between being in denial and avoiding Target Fixation. I’m not sure where the sweet spot lies.

    • And with experience comes maturity. My first failure was excruciating. My seventh failure was still excruciating. My biggest failure (Interliant) was by far the worst and hardest of them all. But you can gain emotional detachment over time as you understand how it’s part of a broader arc.

      • triciatita

        Thanks Brad… I realize I am just at the starting point of my entrepreneurial career and have many more failures to come. However, as a social entrepreneur I acknowledge failure more as an unsuccessful attempt to solve a social challenge in our world. Whether outside variables influenced the failure or not a social entrepreneurs feels that they have let down the people and communities who need support the most. Luckily there may be other ways to create impact in that particular problem area we just have to keep on pushing and influencing through any feasible means.

  • Nice one Brad.

    I hope he or she does respond.

  • mitelhaus

    Having been on both sides of this coin, I can honestly say that you don’t fully appreciate success without understanding what happens when you fail! Great post Brad.

    • Oh yeah – success is much much sweeter after you’ve had a lot of failure.

  • Derek

    I read the “30 days to live post” and was actually disappointed – this sounds like someone who has thrown in the towel without really trying to change their circumstances. I am generalizing here, as this person is obviously under a lot of pressure, but at no time is there an indication that they 1) had it out with their investors (whose vision they followed but did not share), 2) teamed with their cofounder to try to confront the problems they are facing or 3) did anything tangible to try to help themselves.

    Sorry, this is a really cynical comment, but this is not exactly the coping mechanism I would want to see out of a leader. For context, I am the head of business development of a small biotech startup, which I helped start two years ago. I hope my startup does not suffer the same (assumed) fate as this one – I have been part of startup failures before, although my name wasn’t “on the door” so to speak. Again, I hope to not be in the same situation, but if I am I would wait until the conclusion is already written and blog about it post-hoc.

    • I’m not sure I read it the same way you did. I didn’t read it as a conclusion, but an acknowledgement of the current reality along with an effort to process it and figure it out.

      • Derek

        I would imagine that my present state of being (early stage biotech, lean team, fighting to grow the company) likely makes me less than objective here. My disappointment was probably projecting myself into the writer’s shoes. Great comments on this post, love the discourse.

  • Nick Ambrose

    …Interesting use of language “we had cheques being written”
    “Biz Dev, check. Product Management, check. ”

    I would say England or “English” or somewhere close to Old mother England….

    • Nice catch!

      • NickN

        Good catch, but I’m saying Brit based in the US or a Canadian. Speaking as a Brit in the US, if you’re British enough to write “cheque”, the odds that you will use the word “Bro” are about zero…

        • Got it.

        • Nick Ambrose

          Yes, for sure (I’m a Brit in the US too but thankfully dont say/write “Bro” or “Cheque”)

  • Thanks for sharing this, Brad. Genuine or not, it does bring to light many of the caveats of the current tech start-up environment. The most key traits of a successful founder are fearlessness and critical thinking. These are not the best traits for making friends, but absolutely essential to building the foundation of a strong business. Passion, ideas, and accelerators are catalysts, polarizing influences that get you where you are going, faster. Entrepreneur; you have to intuitively feel the right path. For the love of life, don’t let anyone, not even your best friends or investors, push you off of that path.

    • My partners and I add in “brutal honesty” to our own internal discussions and thought processes.

      • I remember your “grinfucking” post. We always get the most out of honest of conversation. I’m trying to help foster transparency in the DFW area.

        • Awesome. I grew up in Dallas so more goodness there is good!

  • Wow, this person is in pain. I really hope they reach out, they really need some help to get through this.

    • Just writing it down may be very helpful to this person. At least I hope that’s true if they stay anonymous.

  • Dennis Ferrill

    It’s good to talk about this. Thanks to everyone for the discussion. The challenge is to have both the optimism/courage that makes real invention possible while also having the resilience to go through the firestorms, including failure, with humanity and competence intact. Recently I’ve been watching a startup in which I have a very small investment approach what appears to be the end. One of our main topics of conversation is how to navigate the emotional and interpersonal chaos that comes from managing a business during a time of fear, disappointment, self doubt, and denial. My feeling is that courage and honesty are the key ingredients, along with the largest possible understanding of what makes up a life. Incredibly hard work but I think also incredibly rewarding. And then, as I tend to say at the end of every email: “Onward.”

    • Well said. Courage and honesty are biggies. Owning what’s going on. And realizing that it is part of what is hopefully a long and complex journey called life.

      • NickN

        And, having gone through this more than once, that courage and honesty needs to be a two way street. When you’re in the role of CEO of a failing company, you have to be honest with your team. But one of the things i have found the hardest to navigate is when that honesty isn’t returned.

        Two examples:

        1) We were trying to get a product milestone completed (a working demo) that was critical to funding. Payroll had already stopped. We had a team meeting where the plan was laid out warts and all. Everyone was asked to consider if they could commit for the next sixty days, regardless of whether they got paid in the interim. The good and bad were made very clear and everyone was asked to think it over, ask questions one-on-one and come back with an I’m In or an I’m Out. We went to some lengths to be clear that there was no wrong answer and no pressure to stay if you couldn’t continue. All we needed was an honest answer so we could figure out if we had the resources to complete the demo, or if our proverbial goose was already cooked.

        This was a small team (<10) and we had a tradition of open communication. Two individuals in particular committed to staying, took on key parts of the project and then left a couple of weeks in to the 60 day window. They failed to complete key tasks and in doing so helped destroy what little morale was left.

        2) I had a co-founder who had to move on due to financial constraints. This was an unfortunate but amicable transition to an advisory role that was discussed and planned over a period of months. Several months after their end date, when we had merest hint of funding (not big – a small bridge) this person suddenly wanted to change the terms of their exit from the company. They demanded guarantees that back pay be settled (because every investor wants their shiny new money to pay past bills), claimed IP ownership (despite signed agreements to the contrary) and worked to convince one of the board members that giving up their options when they exited was unfair even though they still had a significant ownership stake in the company. They basically switched from a co-founder mindset to an employee "grab what you can" mindset. It was a mess.

        The common thread in both cases is a mindset transition from "our team" to "that company". People don't like to mislead or screw over their team mates, but once you have the mindset that it's a faceless company run by "the man", it gets much easier.

        P.s. On reading this, maybe I'm just an unbearable asshat to be in a startup with?

        • Great examples. I have many awesome counter examples where being completely open with the team (in each case strong to begin with) reinforced commitment to continuing down a path in a difficult / stressful situation. Ultimately the statement around “our team” vs. “that company” is the key. As a leader, you want everyone on “our team” – even when the shit is hitting the fan. And if someone doesn’t want to be on “our team”, let them go find a team they want to be on.

          • NickN

            Absolutely agree! I like your summary better 😉

            As a footnote to example #1, there were also several folks that went unbelievably above and beyond the call, including people outside the company (our attorney and some of our mentors). It was their commitment that kept us going.

          • Dennis Ferrill

            So this is what I meant by the chaos of the situation. We’re talking about people after all…people who come to the situation with their own story and their own complex landscapes. When times are hard you can see things you wouldn’t see otherwise. You do the best you can. (The best you can.) And you move on. Sometimes it sucks but sometimes it’s great. Regina Spektor got it right in “This is how it works.” Sort of.

          • NickN

            Yup. And in aggregate, the great is still winning, which is why I continue to do this…

  • We’ve all heard variations of this nice quote that I re-heard the other day – failure is not the falling down but the staying down.

  • Austin

    Related, great book — and free via Kindle, no less — on training yourself to deal with fear and do it anyway: The Flinch, by Julien Smith.

  • It’s interesting he/she doesn’t talk much about the VCs that were involved & why they are seemingly abandoning it.

    • Hopefully that will come.

  • If not a real story, the author is a talented poser. If real, sounds as if he truly is out of DEFCONs.

  • Elizabeth Kraus

    My entrepreneurial failure was the hardest experience of my life, but also the most educational (you can read about it here: Because I learned so much, I love to talk about it, but I find that very few entrepreneurs want to listen. Our angel group tried to host an event to share the hard lessons I learned a few weeks ago and not one entrepreneur showed up. This was really odd because we host well-attended events on a regular basis and I couldn’t figure it out. Then someone told me that Jim Collins’ book about failure, “How the Mighty Fall”, was his least successful book and he attributed it to the fact that everyone wants to learn how to go from good to great, but few people want to know that failure is a much more likely scenario. I’m not sure if this is true, but definitely made me think. Anyway, I definitely agree that more talk about failure is needed. Thanks for posting.

    • If you ever want to do a “failure” talk with me in Boulder or Denver, just holler. My guess is that we could easily fill Galvanize together and it’s such an important topic to discuss.

      • Elizabeth Kraus

        I’d be honored! And I’d be happy to do the heavy lifting on the organizing. Could be a great Silicon Flatirons topic. If you’d like to give me some times that might work in the fall, I’m on it! I’ll email you. Thanks!

        • Send me an email – plenty of opportunities in July / August – I’m around all summer.

  • Cultivation Center

    Brad, thanks for posting about failure. We’ve been thinking about this one for a while here at the Cultivation Center. Sharing about our failures would be such a valuable cross-sector peer learning opportunity. Too bad to hear that Elizabeth’s Angel Group session on failure “failed”. This demonstrates how truly averse we all are of the f-word. This article is a bit dated (from earlier in the year) but gives an example of a somewhat successful attempt at sharing failure to move social change forward:

  • Brad, any video of your failure talk available anywhere?