The 10 Stupidest Marketing Mistakes I've Ever Made

Ian Lurie

This may surprise you, but I tend to dwell on the negative. Here are the ten cringe-inducers I spend the most time pondering. In chronological order, no less:

  1. 1990. I went to law school. OK, it wasn’t a marketing mistake, but it cost me several layers of stomach lining. Law school also nearly killed my ability to write.
  2. 1995. I decide to start Portent Interactive, but name it The Written Word. For the next 5 years, people ask me if I print bibles (I was going for Shakespeare).
  3. 1995. I test my first web crawler on the network of a client (with their permission). I crash the network and earn myself the title “Bringer of Death” from the head of IT.
  4. 1998. I aim Portent at client service, instead of affiliate marketing, thinking the search engines will kill the whole spam thing within a year. I think I had a head injury.
  5. 1999. For reasons I still don’t understand, I sell my company. The next 8 months include a bout of pneumonia, total professional melt-down and at least one instance where I witnessed one of my new fellow employee groping a receptionist in the hallway. I don’t know either.
  6. 2000. Back on my own again, with zero confidence, I sell my services for something under $30/hour, and can’t figure out why I can’t make a living.
  7. 2000. I decide pay per click is a flash in the pan (really) and advise 3 clients to skip it before one of my staff slaps me so hard my eyes rattle against the back of my skull.
  8. 2004. A company offers us cash plus stock to do a project. I accept it. I still have the stock certificate as a placemat.
  9. 2007. Thinking I can Be The Hero, I take on an entire development project on my own. The result resembles three spastic ferrets in a blender. My staff bails me out.
  10. 2010. I lose my temper with a client. Justified? I dunno. But the fallout is personally and professionally excruciating. We’re only human, but the lesson, as always, is to take a walk before you talk. We’ve since begun working together again.

And yet, Portent’s going well (knock wood) and we’re all still here. I think there’s a lesson there…

Nothing related at all

Ian Lurie

Ian Lurie is the founder of Portent. He's been a digital marketer since the days of AOL and Compuserve (25 years, if you're counting). Ian's recorded training for, writes regularly for the Portent Blog and has been published on AllThingsD, Smashing Magazine, and TechCrunch. Ian speaks at conferences around the world, including SearchLove, MozCon, Seattle Interactive Conference and ad:Tech. He has published several books about business and marketing: One Trick Ponies Get Shot, available on Kindle, The Web Marketing All-In-One Desk Reference for Dummies, and Conversation Marketing. Ian is now an independent consultant and continues to work with the Portent team- training the agency group on all things digital. You can find him at

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  1. This list might be the funniest I’ve read yet. Who knew I would race to your blog for the comedic aspects. Thank you Ian for always empathizing with our failures, and inspiring us to remain patient.
    Number 1 kills me… After several years in commercial real estate working with lawyers everyday, I still can’t believe how much time and effort was squandered

  2. You can rejoice in the fact that you didn’t put your ATM pin number in your company name….
    (That’s material for your follow up post – 10 stupidest things I almost did)

  3. Ian, I follow your blog religiously, this post is confirmation why. Your ability to strip away pretense and get to heart of the matter is amazing. I love that you do it with content specific to you as well. Extremely well done, and I will pass this on, as I pass on much of your content.
    Thanks for making me think about things in a different light, and the lesson “to take a walk before you talk” will stay with me for life!
    Thanks again!

  4. I have just discovered your blog and this post brought a smile to my face. I have started a company two years ago and at first couldn’t make any decisons for fear of making big mistakes. What you are showing here is that there is people do mistakes but people also do learn and survive!

  5. Very interesting, at least you express yourself as yourself, it’s not hard to lose tempers with clients, as they most of the time know more than the expert, ha ha. I like the ferrets in a blender. funny stuff.

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