Category: Book Review

This is a great book to read. Some of the business books are a bit of a chore to read, this was one that we looked forward to reading. It is painfully honest at times, and rather than falling for the hindsight bias, that if he is successful now then surely every decision he made before was awesome. Instead he looks hard at what he did, and did not do right. It makes for a much better, much more compelling read. There are several opportunities that he turned down, that in hindsight he explains he would definitely like to have played differently. Hint, if a billionaire comes calling, do at least explore how a possible collaboration might play out…

A Story Well-Told

What kept me engaged on my flight to and from Maui, when I dove into this book, was Lerner’s story. After realizing that a Wall Street career was not for him, he launched an online dating startup (because, you know, that was supposed to be less stressful than working for Lehman Brothers). While the company had wild success after a media mention, the bigger story here is in the mistakes that he made along the way.

Lerner’s story reads like a business memoir (if that’s a genre), peppered with tips to avoid the mistakes he made. Frankly, the tips inserted in the story felt a little redundant to me after the story, but they fell in line with how business how-to books are written today.

Unlike many CEOs, Lerner admits his mistakes and offers insight into how he would have done things differently. Anyone in the startup space would benefit from his insight (such as: don’t leave all the money on the table when you’ve got it…don’t say no to high-profile investors like Mark Cuban, etc.).

The story ends well for Lerner, I think. He’s a media personality and celebrity entrepreneur who has, obviously, written a book. So the moral of the story here is: even if you fail in your business, you can always leverage that loss into something else.