I recently came across a post by Tomasz Tunguz titled The Best Advice I’ve Ever Received, which included the following paragraph:

When I reflect on the best advice I’ve received in my life, it has never been the counsel that provided an immediate point-of-view on an answer. Rather, it was the guidance that started as a single probing question that I couldn’t answer immediately, a question that invited me to look upon the puzzle with a new perspective and demanded deeper thought. A little Buddhist Koan.

It struck a chord with me because a probing question is precisely what pushed us to pivot from Oh Hey World’s original location sharing focus to facilitating hospitality exchanges among trusted community members. We had the concept of a location aware community page in the original Oh Hey World product (see Kiva supporters here), but we didn’t have a strong answer to “why” someone should join them aside from to “connect”.

The probing question came in an email thread with Taylor Davidson. He said something to the tune of:

WHY do you want people to connect? Figure that out, and solve THAT.

I didn’t have an answer. As it turns out, “connecting” for the sake of “connecting” isn’t a compelling value proposition to most people. As we continued to think about the question over the course of a few weeks, we realized accommodations are what drives the entire online travel vertical. When it comes to the intersection of accommodations and community, we had to look no further than private hospitality exchanges for our product focus. Finding a cheap or free place to stay with someone in one of your trusted communities, is an extremely compelling reason to try a new website or app as it both saves considerable money compared to a hotel or even AirBnB, and provides a more “authentic” travel experience.

That single probing question led us down a completely different path…which ultimately resulted in the new private hospitality exchange app we are working on now (we are close to a finished MVP).

It goes without saying, but I’ll say it anyway. Thank you for probing, Taylor.