I’ve been asked by many of my friends and family why I decided to leave my position at Microsoft, where I was appreciated and rewarded, for more work, more responsibility, and more stress. Well, the decision was mainly a result of three factors. First, someday I may start my own company, and transitioning from a startup makes that much easier. Second, I didn’t agree with many of Microsoft’s decisions and direction. Third, I wanted to build a product that would really cater to consumers and could stand on its own.

Almost all the top engineers I know talk ad nauseum about starting their own company, with the caveat of, “I’ll stay at big company XYZ for 2-3 years, then I’ll go out on my own.” Well, it never made sense to me how they thought that they could make the transition from being so removed from the business and the end to end process of creating and shipping a product. Working at a startup, you’re about as close as you can be to running your own business, and you don’t have to spend nearly all of your time and effort trying to raise money. For instance, the only financial statements I ever saw at Microsoft were quarterly reports (as a shareholder), and even those were a mystery. At Redfin, we get to see all of our financials, like pro forma cash flow statements that we might show to investors, and are encouraged to understand it and ask questions. Even raw talent can’t make up for this kind of experience.

While I was at Microsoft, many things didn’t make sense to me. I didn’t understand the massive “re-orgs”, which, if you hadn’t heard about ahead of time, it meant nothing material changed for you. I didn’t understand why we’d try to enter dominated markets with an uncompetitive offering. I didn’t understand those little table tents on the cafeteria tables or the giant banners and posters promoting intranet websites. I didn’t understand why site searches on MSDN were abysmal. I wasn’t the only one who was confused. Minimsft would try to speculate about a re-org or an acquisition. And on popular internal aliases like “litebulb”, for instance, there’d be email threads where people would ask why Vista had 6 (ok, SKUs, why Zune wouldn’t work with PlaysForSure, why their product had to be renamed from something cool to something like Windows Communication Framework, or why there were 2 confusing boxes on local.live.com (or so adverse to just calling it “maps.live.com” in the first place). Legitimate questions often got defensive responses. To paraphrase one developer, “Why are these responses always along the lines of, ‘We know what we’re doing’? Personally, I’d welcome the feedback, because that’s how I’ll improve. Why can’t you provide the reasons that led to your decision?” I couldn’t have agreed more.

Once I had decided I was leaving the company, I spent a lot of time trying to find the startup I’d be most passionate about. It sounds arrogant, but good software engineers can pretty much choose where they want to go. And it’s nearly frictionless to change jobs these days. You can post your resume up on Monster and get daily calls and emails. So, you do your homework and find a startup that really appeals to you. I was definitely not looking for some me-too social networking site or some company that was funded purely based on its management team’s connections. When I found Redfin, I knew it was just what I was looking for. During my home buying process a few years ago, I was convinced the real estate industry needed some serious changes. For instance, searching online required clicking in a multiple highlight box with 50 neighborhoods I’d never heard of, but I checked them anyways just in case they were somewhere near where I wanted to live. After much research, I learned that my agent would probably be getting a 3% commission when I bought a house. It wasn’t a “free” service as many led me to believe. Ten grand to drive me around and guilt me into buying a house I didn’t feel was right for me? Redfin’s scrappiness and audaciousness to battle it out with the traditional agents, brokerages, and MLSs on behalf of consumers like me was very appealing.

Startups aren’t for everyone. But for any of you on the fence and considering the startup world, here’s my advice:
- Plan for the future. Thinking about what I could accomplish in 5 years at a well established company versus a nascent one intrigued me. You’ll have much more influence over the development of an infant than you will a 30 year old, and the rewards should be commensurate.

- If you refer to your company in the third-person, or have to ‘beat’ the system to be productive, it’s a bad sign. (One rumor at Microsoft was that your group should spend exactly 100% of its budget/headcount, otherwise ‘they’ would cut next years.)

- Make sure your whole company feels like one team. Ballmer once joked at a company meeting, “Why do the different groups only clap for themselves?”

- Be as important to the company as it is to you. In a technology startup, the people ARE the startup. Our CEO reminds us, “The company’s only assets walk out the door every night.”

- Consider working where there are no sacred cows. Don’t like something? Be able change it!

- And finally, to quote Paul Glen, “Never underestimate the power of free food.”