Will Work For Food: Why I Left Microsoft for a Startup

Free Lunch At Redfin

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, 8) 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.”


  • Savan

    How about:

    - You can wear a bright red hat and $10 flowered shirt and still have a job the next day.

    That’s the one I love the most.

  • Noam Lovinsky

    Never underestimate the power of free food or the speed at which you must foist said food into your mouth when eating with a certain CEO.

    Good post Jeff and congrats on the move from Microsoft!

    • http://www.newhomesteps.com New home building guru

      Free food will always move people. Nice choice.

  • http://doingboeing.blogspot.com Adam Phillabaum

    Congrats. I did a similar job switch a couple of months ago (Boeing –> PayScale). The interesting thing for me wasn’t the change in jobs… but the change in lifestyle.

    At Boeing, I was in bed by 10PM and awake at 5:45AM, so I could be at work ~7AM and leave by 3:30 or 4PM. Just 3 months later (exactly 3 months later), I usually get to work around 9AM and leave at 5:30 or 6PM.

  • http://blog.redfin.com/blog/author/glenn%20kelman Glenn Kelman

    Nice post Jeff. What I don’t understand is the Microsoft employee’s anxiety about job security. It seems hard to imagine that a software engineer would be unemployed for long. Why is this a commonly cited concern?

    • Jalen He

      Some people have been living in a green house for so long and became afraid of the wild world outside, and they start being concerned of how to survive once they are let out

  • http://www.triggit.com Zach Coelius

    Congrats, that first leap from corporate life to a startup is the beginning of a sometimes wonderful journey.

  • http://informationrain.com/ Chris Papadopoulos

    Congrats for doing what you really love. I wish more people did the same.

  • http://www.innovators-network.org Anthony Kuhn

    Thanks for cheerleading the need for young people to try out new things. If things aren’t the way you’d imagine they’d be, there’s only one person with a hand on the tiller of your boat: you! Hard about, and track a new course to future success. You’ll have lots of company in the near future! I cross-posted on your piece to http://blog.innovators-network.org
    The Innovators Network is a non-profit dedicated to bringing technology to startups, small businesses, non-profits, venture capitalists and intellectual property experts. Please visit us and help grown our community!

    Best wishes for continued success,

    Anthony Kuhn
    Innovators Network

  • http://robsnewchapter.blogspot.com/ Rob Mathewson

    “Successful” companies eventually reach a tipping point where they lose their will to take risks and begin protecting what they have. It’s a fuzzy line, no doubt. But those of us who have enjoyed the startup environment know that we always want that line in front of us and never behind.

  • http://blog.redfin.com/blog/author/glenn%20kelman Glenn Kelman

    John Rosemas! What does your comment have to do with Jeff’s post about startups vs. Microsoft? Let us know, or we’ll delete the comment. The only reason we delete comments is if their sole purpose is to promote another site, like a Viagra site. Yours seems to fall into that category.

  • http://www.bkcyprus.com cyprus realty

    I never thought that a person with such a lucrative job will leave it. Anyway I think you have done a great decision considering that principles are more important than money. Anyway its good to know that there are still few people having a grip of its principles over money. I think your living a good life now considering your free of too much stress.

  • Bandito Bandillero

    Good luck on your new assignment. For some of us, Microsoft is the only place we can work. Microsoft culture allows the maverick, non-conformists among us who want to work at 150% one time and then 25% at another, or want to make the splash that starts the next ripple wave, to do what we want to do. But it is not for everybody and I wish more people will follow your lead and go where they can be happier

  • http://jai2c.spaces.live.com J@MS

    Thanks for the tips. Just in time for me :-)

    I am contemplating the move too as I am sick and tired of being fooled by the MSFT system. No, I am not bitching because I got a bad review… I have always received “exceeded” (or equivalent in the old system) in my reviews and my manager can attest to the fact that I am performing @ two levels above where I am. But I am just fed up of the slow growth and the fact that you need to stab someone else to go ahead and ofcourse the zillion reorgs with no light @ the end of the tunnel.

    I have always worked at medium to large sized companies and would love to work for a startup… if you have more tips on selecting a startup, please blog or point me to it if you already have done so.

  • Startups

    It is not always easy to join a startup. There are downsides. I would rather suggest folks to join smaller groups in established companies that give the same opportunities

  • I Love MS

    J@MS… not sure why you feel that this happens only at Microsoft – since you have always worked for large sized companies… is this something unique you have in Microsoft. I love this place and would not trade it for anything.

  • J@MS

    I am sorry- I did not mean to say that this happens only @ MS. I have seen it in ALL big companies. Trust me, I love MS as much as you do but I need to think about growth too. I still feel MS is one of the best companies for college grads not for someone like me who has been in this industry for 10+ years. I think one should work in a startup if he/she wants to start on their own OR want to play a bigger role in the growth of the company.

  • http://thoughtsprevail.blogspot.com Himanshu Sheth

    Though I agree to all your points, I would add one more: A country like India where the social bonding is so much, startups don’t only become a hindrance in marriages but also in many social circles.

    As you pointed out, we have to plan out for next 3-5 years what we need and that is more important.

    Last but not the least, I loved this line :)
    “Our CEO reminds us, “The company’s only assets walk out the door every night.”

    -Himanshu Sheth

  • Vinod

    Although people find it very exciting to join a startup company anticipating tremendous growth opportunities, I would like to warn people to check the company properly before joining as I have been a victim of the same.

    I was working for an organization of repute. Expecting huge growth in a startup, I joined K2 InfoEdge Private Limited that promotes a portal Skills4U.com. The CEO of the company Mr.Manoj Nagaraj utilized my Services in the capacity of Sales & Marketing Manager for one month. After completion of one month, he did not pay me Salary due to which I had to quit the organization. The organization had the malicious intention of just utilizing my rich experience of working with a well known company that was in the similar line of business for a short term and no intention of retaining me as an employee of K2 InfoEdge Private Limited.

    Please refrain yourself from associating with companies like K2 InfoEdge Private Limited/Skills4U.com that cheat people to the core.

  • Harsha

    nice blog… gives good motivation
    but how to find such good company … obviously info wont be available in the net i think

    • Bren

      Interesting article, but you show your inexperience with all those “unanswered questions”. The answers to all of them have been discussed on the right public mailing lists inside the company, and there are quite good reasons for each.

      • Glenn

        Inexperience? I think that's an old school mindset which needs to be squashed out of existence.

        I believe that each of those “unanswered questions” should be reviewed quarterly and discussed – If the answer remains the same then there is something wrong.