It's worth hearing Betsy and then hearing the investors take on execution (roughly 45 minute mark). Quite a contrast.
We had talked to them when they were getting started. Sounds like its good we didn't end up working with them. Still I think the concept is fantastic if the model can be figured out to make it work.
It's funny to hear Betsy describe it as dating for product placement. Because of our work on eHarmony, we often find matching as a core component of systems. Interesting to hear Betsy say that the technology was not differentiated. Yet while the rest of the people on the podcast talk about some of the things that customers were asking for, there was lots of opportunity to make it differentiated. Maybe we should have talked more. :)
I asked this of them two years ago, but I still don't understand is why they weren't able to manually make matches while they were looking to get larger sales and scale both sides of the business. Scaling a match making business can be challenging since you need critical mass on both sides. But a manual match would be found money/opportunity for both sides. There's not much downside for the customers on each side and would lower resistance. Further you could make payments be a percentage of the deal.
I'm surprise this wasn't part of the model of how they'd get to scale. It's hard work, but very common. I know we discussed this back at the start.