Words of wisdom from Jonathan Crowley and an unconventional pricing approach


Jonathan Crowley of Foursquare (and various entrepreneurial ventures before that) came to visit and had several interesting points to share. (Along with a pretty hilarious story about how the name of his company, Black20, came to be — betting company money on one spin of a roulette wheel.)

One point that jumped out to me was this:

“Working for yourself is both extremely hard and extremely rewarding,” he said. “When you’re sending that 5 am email or working on weekends for another company, you’re thinking ‘Why am I doing this?’ When you work for yourself, you know why you’re doing it.”

Very true, and something that stuck with me as I bounce between working on my own project and doing part-time work for a couple of larger/more established firms. The flip side is that with established companies, there seems to be less uncertainty: When I do X, I know it will yield Y result. (Generally.) It’s easy to revert back to what feels comfortable, a tried and true result, and what you know will generate revenue.

How to generate revenue for my project is something I’ve been trying to wrap my head around, and we also talked a lot about pricing strategies this week. As I put together an eBook on baseball, I was considering anywhere between $.99 and $4.99. I was getting hung up on $2.99 versus $3.99, and naturally, that got me thinking about Chipper Jones, a Braves player who just retired after 19 years with the team — was his career batting average in the high .200s or low .300s? Turns out it was .303. So $3.99 it is!

There’s a lot of value in doing market research and financial models, but sometimes, you just have to make a decision and stick to your guns. So you can make mistakes, learn some lessons, and make the next one better.


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