Douglas Olson discussed his experiences working in the world of startups and large corporations on Friday at Thinc Iowa. Photos by Anna Jones from Anna Jones | Art of Photography and Tom Woolery from Ikonix Studio.
Douglas Olson brings almost two decades of lessons learned in the software business and entrepreneurial development to his current position as the partner director of development for Microsoft’s suite of creative design and media applications: Microsoft Expression Studio. Now the head of the Expression team, Olson manages development and user experience within Expression Studio. During his talk on Friday afternoon at Thinc Iowa, Olson touched on some of the lasting lessons he has learned in his career.
Five T.I. Takeaways
1. Calculated risks often pay off
Olson pulled no punches on the topic of taking risks as an entrepreneur: “You will not be successful if you are not willing to take risks.” Olson touched on gaining traction and making things happen at Adobe. “If I don’t blow you away within the first six months, fire me,” Olson recalled telling Adobe. Of course, he didn’t get fired, and the release of the first cross-platform version of Adobe Photoshop was the start of an impressive run. “None of it would have been possible,” Olson said, “without taking some risk.”
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2. World-class Midwest talent
Olson discussed misconceptions about finding software talent in the Midwest. “I was completely wrong about being able to hire good people in the Midwest,” he said. “There are good people here.” Olson pointed out the Adobe team (mainly producing Photoshop and Illustrator) that he built out of a basement in the Twin Cities over a decade ago. Since then, the team has grown (70-plus strong) and no longer works out of a basement, but it is still proud to call the Twin Cities home. “There is awesome talent here,” Olson said. “You just have to know where to look for it.”
3. There’s no room for hubris
There is no question that Olson has enjoyed great success in his software career, but his cautionary message was grounding. “You can get caught up in your success in a way that just isn’t healthy sometimes,” Olson said. “I’m not known as the guy who did Photoshop or the guy that did Macromedia,” Olson continued “It’s what you do today that matters.” Success is something to learn from, but it shouldn’t define you.
4. Small vs. big
Although Olson has been with Microsoft since 2005, his roots are startups like Macromedia, Authorware and Zoapworks (later time4.com). “I’ve always loved the feeling of a startup,” he said. But, at the same time, Olson enjoys his current gig. “Microsoft is one of the most amazing places I’ve ever gotten to work,” he said. The challenge is to build a startup culture inside the biggest software company on the planet. That is the only way Expression studio can engage, compete, and win with the creative software on the market.
5. Have passion
Olson reiterated one of the central themes of Thinc Iowa: the ingredient of passion in what you do is absolutely essential. “If you don’t love every hour of what you’re doing, you’re just not going to be very good at it,” he said. “(Passion is) crucial to be successful in this business.” Olson also made it clear that people are the cornerstone of any organization, regardless of size. Treat them well and it pays off in the end, he said.
*Update October 25, 4:40 p.m. – Takeaway 1 was updated to identify Adobe Photoshop 2.5 as the product in question. Previously, it was misidentified as Creative Suite 3. Takeaway 4 was updated to reflect the name of one of Olson’s startups as Zoapworks. Previously, it was referred to as Zoapbox.
