What to do when the hockey stick doesn't happen on your timeline?

It's been almost 2 years since we sold Judy's Book for a loss.  Recently, I've been reflecting upon the experience with the benefit of hindsight and of time. 

In the past, I've already blogged here about mistakes I made at Judy's Book : the failure of aggressive customer acquisition, poor market selection, and too ambitious of scope in categories and geography. All these factors led to a local web site that lacked necessary critical mass.

As a reminder, there were two parts of Judy's Book --
i) as a company we were a local reviews social network for 24 months and then,
ii) we shifted directions and we were a local deals site for 12 months.

As I look back on the business decisions I led during that time, I see a company that was early in a market, executed pretty well, but didn't have the perseverance or patience it needed to succeed.

I remember looking for a hockey stick moment and when it didn't happen on MY timeline, emotions kicked in. I got down on myself, the company and the opportunity.  Emotionally, I became depressed and that led to greater impatience. The daily emotion toll of unmet expectations clouded my business judgment and prevented me from appropriately evaluating the situation  -- it undermined my assessment of the value of assets we had created.  You know when you feel like shit, everything tends to look like shit and reinforce the feeling.

What I should have done

  • Personally:
    I should have taken a minimum 2 week vacation. Yep -- totally counter-intuitive. But I should have gotten out of the storm to gain perspective.
  • Business wise :
    I should have downsized the local reviews site and let it grow organically with at most two developers rather than trying to convert the entire thing into a local deals site. 
    I should have gone back to the original documents and revisited the initial theses of starting the company. I likely would have been re-focused on the social network and viral acquisition strategies that had us excited about the opportunity in the first place.

A business that changes directions is fine -- but comes at a great cost of TIME to a founding team and to investors.

Remember that perseverance is critical to success. Success rarely happens in a straight line and the emotional toll on entrepreneurs is HUGE. Don't underestimate this. Exercise a lot. Take a break and then come back and kick some ass.