Startup Lessons from Microsoft Employee No. 121 – Scott Oki!


Last week was the maiden voyage of Startup Grind Eastside, hosted by Impact Hub Bellevue.

Mike Grabham grilled Scott Oki, aka Microsoft employee 121. They chatted about his ten years under Bill Gates, his subsequent ventures and adventures, and of course, the state of the public school system.

Some things you might not have known about his time at Microsoft:

  • Scott went three years without taking a single day off. When he mentioned that to The Big Bill G, the response was “So what?! I’ve worked seven and never had a day off!”
  • His interview was more like a lecture – Gates asked him only one question (and he never mentioned what it was…)
  • He remembers sending emails on Christmas day to Gates, and getting an email right back. This was back when you needed to be hardwired to the machine, none of these devices.

Two weeks after starting at Microsoft he noticed no one was paying attention to the international market. So he pitched for $1 million (think Doctor Evil) to make it happen. Fours years later, the international market accounted for 42% of revenue and over 50% of profit.

Spearheading this effort, Scott worked the 100 hour weeks, and flew more miles in a year than the average commercial pilot. Exactly ten years to the day after he started, Scott bowed out of Microsoft. His wife Laurie and their young kids (whom he “tries not to spoil”) were the reason – he wanted to be there for his family.

 When Oki mentions his wife Laurie, his face lights up. He talks about their recent trip to Cambodia and their plans now they’re going to be empty-nesters. It’s clear their marriage is a source of strength and inspiration. Laurie was in fact the catalyst for his most recent non-profit venture, into the public school system.

 Scott sits on the board of over 40 non profits, and has personally founded 20 non profits. He is candid that some are more successful than others, and he does have some darlings in the mix.

 Scott believes these should be a world without non profits, and instead, for profits with a social mission.

His major grievance is that when you’re non profit you don’t have the luxury of offering the most cash and stock options, cutting you out of the higher end of the talent pool. For example, he credits Nancy Cho (CEO of Oki Golf) with the company’s success, but he would not have been able to place a competitive offer on the table for her with a non profit.

When asked about his biggest point of pride(other than children, of course):

Scott is most proud of being the only college dropout on The University of Washington Board of Regents.

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