Business (and Life) Is Messy

Posted on April 8, 2011
Filed Under Business |

A few years ago, shortly before my grandfather passed away, my grandparents celebrated their 50th wedding anniversary. On a day when family and friends were celebrating this achievement, my grandmother pulled me aside in the middle of it all to tell me something she had to get off her chest. She said that if she could do it all over again she wouldn’t. So much for the admiration of true love. But surely this is an outlier, right?

Fast forward to last summer when a friend of mine told me about the couple who used to live across the street and how she and her husband grew to know the couple over time and admire their marriage. The older couple gave them marriage advice during the many dinners they shared together. Then, as the elderly husband got sick and was on his deathbed, the wife confessed that every day, she hoped he wouldn’t come home from work. She said that she hated him and wished he had died long ago.

Memories of both stories were triggered this week when an interesting message was posted on a usergroup to which I subscribe. The gist of the message was that dropbox sucks and the company is looking for an alternative solution. Apparently, as groups that share a file or folder increase, dropbox’s performance moves in the other direction.

I was surprised to see that message about a company so beloved by the press and supposedly by their users as well.

The lesson here is that things are never really what they seem. The outside view of a company, of a marriage, of someone’s life, are carefully constructed to convey what we want people to think, not what really exists. I don’t think this is necessarily a bad thing, but it can lead to problems at times when you have problems and you think you are the only person or company going through such things.

For example, people rarely volunteer that they have had a miscarriage, but if you ever have one, and discuss it with your friends, you will be surprised at how common they are.

And sometimes the truth is just difficult, or uninteresting, to disseminate. We had a problem at Backupify several weeks ago when, after a massive influx of new users, we had some routine maintenance go awry. We had to keep putting our site in maintenance mode for most of a several day period because of a problem with the Cassandra upgrader (it was an estoeric memory allocation error) and some users freaked out because in maintenance mode they can’t access their archives. All of our user data was fine, most of our users had no problems, and the real details of the technical issues and the users that were affected by them were never really discussed. When I actually offered some journalists the real explanation, their eyes glazed over. It wasn’t an interesting story.

The most interesting thing about moving to Boston and taking VC money is the things I have seen now that I am an insider in this ecosystem. I’ve learned that so much of what you read about who is, or has been, successful, is wrong. There are companies held up as role models that are really a mess if you raise the hood, and companies you have never heard of that are crushing it. There is hype, and there is substance, and the two are rarely in sync.

What is the point of all this? The point is that as an entrepreneur, or startup employee, it is easy to get derailed. We all want someone to look up to. We are quick to idolize. We cherish heroic stories and after the fact narratives that may not be totally true. When things get messy in your own startup, you can think you are the only one. You can think you won’t get through these things. But you aren’t alone. You are normal. Business is messy. Life is messy. Messiness is the normal condition of the world. Embrace it, and you are more likely to get through it successfully.


9 Responses to “Business (and Life) Is Messy”

  1. Bill Dotson on April 9th, 2011 4:38 pm


    True. Very true. The inside is often much messier than the outside.

    Along the same lines…the cliche that one should never meet his/her heroes is often true.


  2. Messy and Fluffy | Solojent on April 11th, 2011 7:05 pm

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  4. laurence haughton on April 13th, 2011 11:48 am

    Great note… I’m so happy to see you keeping a clear eye and looking below the surface as you are sorting through the mess.

    On the subject of the press I always keep in mind what Scott Adams observed, “Reporters are faced with the choice (he says daily, but now it’s hourly) of painstakingly researching stories or writing whatever [PR] people tell them. Both approaches pay the same.”

    He right, except I would add that the latter approach, with an eye toward writing confirming evidence (writing what people want to believe) and flattering those who the writer perceives as someone who could advance his career, pays even better.

    So reader beware…

  5. Janet Aronica on April 14th, 2011 7:39 pm

    I’m so glad I got to read such a candid post. I think that at the end of the day only you and your team can *really* know what is going on with your startup (and maybe some of your closest inner circle friends who will love you whether your company is sold or folds.)

    I feel like startups are glamorized by the press. Look at Tech Crunch: you don’t really get coverage unless you raise money or get acquired. Where’s the story of the everyday, what really happens? How you launched a new featured, did customer development… then no one liked that so you tried something different the next week. Then a competitor came into the space so you had to re-think your business model and sat in a two hour meeting brainstorming that. That doesn’t get headlines so much but that’s startups.

    The best we can do is focus on our goals. Learn from others and support each other yes, but focus on our young businesses first and foremost and *never ever* buy into your own hype.

  6. Bradley Joyce on April 15th, 2011 10:58 pm

    Rob, great post… it’s so true. I think that a lot of entrepreneurs who are fighting through the trenches right now need this kind of reinforcement. All the hype can get out of control and can be a bit depressing if you let it get to you.

  7. Alex Pyatetsky - CMO @ The HOTH on April 15th, 2011 11:20 pm

    One of my mentors once told me, “You are going through a growth phase in your life right now. You’re going to experience some awkwardness. There always is with growth. We want you to be comfortable with awkwardness.”

  8. Dror on April 16th, 2011 12:23 am

    And what sucks about this is that companies that are better at talking the talk than walking the walk will get more exposure, funding earlier and other perks that will make it easier for them. To some extent it can be a self fulfilling prophecy.

    Can’t let it drag you down though. Just keep focusing on building a great product.

  9. Vishal Mehta on April 17th, 2011 7:49 am

    Very profound and straight. I couldn’t agree more to the dimension you’ve expressed neatly. Thanks.

  • About Rob

    Rob is co-founder of He likes value investing, the Rolling Stones, college basketball, artificial intelligence, economic history and people who think independently.