My 3 Greatest Failures in My First Start Up.

Failure number 1 of 3.

In my recent ‘stepping down’ blog post, I mentioned my average 140 hour work weeks. While some might have read this as a self-fulfilling pat on the back, it was nothing more than a call out to one of my greatest failures.

Mistaking muscle for strategy.

Moreover, believing the popular belief of “but if I wasn’t naïve, I wouldn’t have made it this far…”

This far? You mean, I wouldn’t have almost had a Britney Spears circa 2007 meltdown!?

Come on…  

If that were true, everyone’s first business would be more successful than their second. And we all know, that is rarely the case.

So here I am, in full transparency, telling you that one of my greatest mistakes was A) being dumb and B) thinking it was ok, because I was willing to dedicate every waking hour of my life to being less dumb.

A recipe for complete and utter burn out.

On Sophia Amoruso’s Girl Boss podcast, she interviewed the ex CEO of Lululemon, Christine Day, who also mentioned this as being her greatest advice to new entrepreneurs. She then went on to tell a story about when she was running Starbucks and mistook muscle for strategy. The entire team was working long days and longer weekends, only to end the year missing their goal by 60%. A 60% miss with more hours clocked than ever before. So they went back to the drawing table, limited hours, focused on strategy, and finished the following year meeting their goal 100%.

Strategy and Knowledge; it’s actually important.


You work less, because you waste less time. You fail less, because you have a plan.

When focusing on strategy (and/or productivity of your time and talents) the hours you work are more meaningful and directed. My life was essentially a never-ending loop of throwing spaghetti noodles against a fridge and seeing which ones were cooked enough to stick.

Example: I spent over 1100 hours one summer trying to set up an inventory management system, only to realize it was not the right system for what I was trying to accomplish… 1100 hours where I literally hated everyone and everything with nothing to show. NOTHING TO SHOW. I was not only pissed off, but I had also just wasted 1100 hours of time that could have otherwise been used to grow my business. Moreover, team morale hit an all-time low as I climbed the raging asshole ladder.

Strategy: I would have calculated the ROI of my time to come up with an hourly budget for an experienced consultant. I would have hired the consultant and then focused my attention back to doing the things I excelled at (which always equaled growth). In the end, I would have had a working inventory management system and one less (unnecessary) failure. However, had I not been able to find a consultant within my budget, I would have tabled the entire project as it was not an immediate fire.

Sadly, the above example is 1 of 6,784.

Strategy is knowledge. Knowledge is experience.

I’d now advise any new entrepreneur to know their industry inside and out before diving head first into it. Get a job, beg for an internship, whatever it takes – do it, and do it for at least a year or two… preferably two. If at the end of those 2 years you find yourself saying ‘no thank you’ because you now know too much… Well, then you’re welcome. If you know too much and you don’t want part of it – THEN PLEASE UNDERSTAND – you shouldn’t fucking be in it.

I’d also advise entrepreneurs to build a large and powerful advisory group of experienced professionals in a similar/same industry. Large, because it allows for multiple outreach without over taxing 1 or 2 individuals. Powerful, because you won’t have the time, money, or headspace for shitty, sort-of accurate advice. Go straight to the source… lots of them.

Which leads me to my 2nd greatest failure.

To be continued…







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