Anything is possible.

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. With Oh Hey World, I tried to use a Zillow strategy – build something that everyone can use (EVERYONE shares their location with someone upon arrival in a new city, right?) – without any real money. As you can imagine, that didn’t work out so well (see here). Over the past few years, I’ve learned strategies differ substantially bootstrapping a company (which is how most startups are built).

I talk to founders in the real estate industry on a weekly basis. Most find me via this blog, though I meet some via friends or inside communities I belong to.

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.

I’ll be honest, I often hate that I now look at every website/app (aka business) from an investor perspective as a result of being peppered with questions for the last few years about Oh Hey World / Horizon. Investors are a skeptical bunch because real dollars are at play and there is no sense throwing them down a hole they can never climb out of. They want to understand your thought process, and need to believe you’re smart and perseverant enough to gain real traction in the market. I’m skeptical when I speak to founders, on purpose. It doesn’t impress me anymore that someone can build a product. That’s the minimum bar to build a start-up; table stakes. Having a number of people in your trusted circle say “oh yea, that’s a great idea, I would use it” – doesn’t mean anything to me. Virtually everyone you know will tell you that, because they want to be supportive. What people say they will do, and what they actually do…are two completely different beasts. A start-up is a massive undertaking you are likely to spend years working on. That is time you will never get back, and could be spent doing something else. Or with your family.

I’ve had a lot of smart people tell me what I’m working on won’t work. That’s fine, they don’t know the market like I know the market. As a founder, you’ll never succeed if you believe everything, everyone tells you applies to your specific scenario. I genuinely appreciate those who provide real tangible feedback about what they’ve seen work / not work. The themes that emerge over the course of those conversations are what’s important. Oh Hey World missed the “location check-in craze” by about 4 years (people are now bored of checking in). Maybe, if we had launched it back in 2008 or 2009, or even 2010 (when I originally dreamed up the idea), it would have caught on enough to reach critical mass with the early adopter crowd. We didn’t have anything to do with the accommodation (the monetization mechanism of the entire industry). We made countless other mistakes; way too many to list here. I would have saved a lot of my own personal money had I listened to recurring themes heard from those with extensive travel industry expertise early in 2012 and 2013. But I didn’t. I was young and naive, and ultimately, had to learn those brutally hard lessons for myself.

I genuinely feel I’m helping founders by being honest rather than just blindly telling everyone to go build their idea even if fairly certain the particular product and/or strategy won’t work.

That said, don’t let me or anyone else ever tell you you can’t do something. Because that’s false.

Don’t take it from me. Take it from Will Smith.

So…remember….

[Photo via http://www.anugrah.net/]