The lesson [.] is that if you work longer and harder you might get there, but it’s more likely that you won’t. Now I’m now always looking for opportunities where spending more money vs. more of my time will have a disproportionate effect on the success of my company.

Hiring too slowly is equally bad. My most painful memory? In the first year I was at Mint, content was a big part of our on-the-cheap marketing strategy and there wasn’t a blog post we put out that I didn’t write or edit. I was doing my CMO job during the day, and spending nights and weekends as our blogger. Initially, I thought that was the only solution. Heck, we even earned Webby accolades. But, after 6 months, I realized it wasn’t scalable and I started looking for a Blog Master. Once I hired Lee Sherman, it was like going from black-and-white Kansas to TechniColor Munchkinland. Overnight, the blog ran so much better and was so much more efficient. He knew how to hire writers, manage content and edit – all of which I didn’t – and he introduced infographics and tools that took the blog to a different level.