Get the most from your holiday rental

I believe that. In fact, I know that. Starting my start-up career at Zillow (see this for some perspective) was a very good and very bad pre-cursor for my entrepreneurial journey over the past few years.

It was great in the fact that I now KNOW building a technology business at massive scale is possible; I’ve seen it done from the inside. Most people seriously question whether building something that reaches millions of consumers is possible, because they haven’t seen it with their own eyes

It was bad in the fact that, prior to starting my own company

I thought start-ups were easy. As an employee at Zillow, sure there were challenges, but from my perspective there was never any real risk the company wouldn’t succeed. That’s why I took a personal loan when I left in 2010 to buy my options; I knew there was basically zero chance I’d end up on the short end of the stick (and I didn’t). Of course, Zillow’s not the average start-up. Most start-ups don’t have $6 million in funding pre-launch, a team of 50+ without having shipped a product, or a founder with a multi billion dollar company that transformed an entire industry under his belt.

They seek product feedback and strategy. They want to know about problems and incentives for agents as well as consumers. They are looking to get a handle at how to gain adoption, traction, and partnerships in this massively complex and wide-reaching industry we operate in.

Many have no prior history in the industry. Others were agents at one time or another. Still others grew up in a real estate family.

I’ve seen 10 years of what has worked, and what hasn’t. When I hear a pitch or play with a product, I tell it how I see it, regardless of whether that’s what the founder wants to hear. Sometimes, it doesn’t validate their strategy.

“Some don’t like the brutal honesty. Others love it.”