Following up on my post yesterday, below are answers to the question of what's been harder than expected at Judy's Book.
Achieving critical mass in local
Momentum in any one location doesn't transfer to others – you have to fight the same fight over and over.
Attracting + keeping people (i.e. consumer users as opposed to businesses)
Getting onto a person's radar screen is hard (harder than anticipated). Even with a big funnel, converting visits into signups, signups into repeat visits, & then into active use requires lots of money or passion or (best case) both at once. I know this is the process any business must go through, but doing this in the domain of "local reviews" only was hard. It's not so hard to get people engaged at the point of time when they are searching for a plumber but this engagement doesn't necessarily translate into a huge number of reviews.
Getting money from local merchants
Local merchants and local marketing spend just hasn't moved online at the rate that we anticipated when we started the business. Moreover, the degree of fragmentation (location + category + size + etc.) and the inability to reach the decision-maker (I came to believe that self service for this market won't work -- I think you need feet on the street to address this market). We began to talk about this problem as the cost of sale problem at Judy's Book.
SEO should be pretty straight forward but when your business gets 30% of traffic from Google search, being good at this is harder than we thought it would be. Google holds all the cards, they keep changing the rules, and the time delays before results are make the entire process of getting traffic from google painful.
This is not an exhaustive list. There are lots of other things that have been hard too...but this is what bubbled up for my management team. Tomorrow, I'll post what has been surprisingly easy for us at Judy's Book.