Bryan Mistele of INRIX and Bryan Trussel of Glympse
Bryan Mistele of INRIX and Bryan Trussel of Glympse at a networking event hosted by GeekWire, 9Mile and StepNW

There’s a common stereotype in the tech community that ex-Microsoft employees don’t necessarily make for the greatest entrepreneurs or startup employees.

Of course, there are countless examples that run counter to this stereotype — whether Rich Barton at Zillow or Forest Key at Buuteeq.

Karan Khanna of 4C
Karan Khanna of 4C

But, at least according to three Seattle area startup entrepreneurs who cut their teeth at Microsoft, there’s a hard truth that comes along with their Microsoft DNA.

The software giant — a one-time monopoly known for internal politics and a challenging bureaucracy — is not really the best training ground for entrepreneurship.

That was the word from Glympse CEO Bryan Trussel, 4C co-founder Karan Khanna and INRIX CEO Bryan Mistele — who together put in more than 30 years at Microsoft in the 1990s and early 2000s. Now entrepreneurs of successful Seattle area startups, each shared insights from their entrepreneurial voyages, and what impact Microsoft played in their journeys.

Bottom line: Not much in those critical early stages. In fact, in many ways their Microsoft backgrounds were stumbling blocks.

Last night’s panel discussion was a Startup Day warm-up event co-hosted by GeekWire, 9Mile Labs and StepNW — with this topic also on the agenda for the big entrepreneurial bootcamp on Jan. 30th.

Asked whether his Microsoft lineage helped or hurt when starting Glympse, Trussel noted that it was a “delicate” issue.

“For me, starting a startup and trying to raise money, I think it hurt. I was told it hurt,” said Trussel, who worked in the games business at Microsoft from 2001 to 2008 prior to co-founding Glympse.

Venture capitalists cast a wary eye on his past career, with Trussel noting that fundraising was an “uphill battle” in part because of his Microsoft DNA.

“I think both perception-wise it was hard. And, to be honest with you in practice, there was truth to it that some of the big company speed and bureaucracy was stuff that I had to shake when I was in a different model of a startup,” he said. “It definitely hurt early-on, but I will say now since we are a little bit larger and have a little bit more funding, now all those things that I learned (at Microsoft) are actually really helpful. Now, we are getting to the easy part. I know how to scale, and I know how to run big organizations.”

Attendees at a Startup Day warm-up event at Kirkland's Nytec
Attendees at a Startup Day warm-up event at Kirkland’s Nytec

Mistele, who spun off INRIX from Microsoft in 2004, offered a more biting criticism. “I think the Microsoft brand, especially in 2014, hurts any entrepreneur that is trying to raise money,” he said.

Mistele said part of it is a perception that Microsoft is not the innovator that it once was, but he also noted that there’s truth to the stereotype.

“At Microsoft, you live in a bubble. You think the world codes in C# and uses .Net frameworks and uses SQL Server,” said Mistele. “The rest of the world does not do that folks. So, there is a real aspect that Microsoft technologies do not dominate the world anymore.”

Mistele, however, agreed with Trussel that the Microsoft training has helped once the business got off the ground.

“For better or worse, Microsoft knows how to build software, and I learned how to run a large technical organization and how to do world-class marketing that I would have never have learned from a startup,” he said.

Both Trussel and Mistele stressed the importance of breaking out of the Microsoft bubble, networking with people from the startup community or other tech companies. They also noted that most big companies have multiple departments that take care of key issues, rather than everyone carrying the load at a startup.

Bryan Mistele of INRIX
Bryan Mistele of INRIX

“Understand the different world that you are jumping into when you jump into a startup,” said Trussel, adding that he often asks job candidates from big companies how they’ll survive when they don’t have brand recognition or a big marketing department behind them. “When you go to a startup, nobody knows who you are.”

Khanna, who spent 14 years at Microsoft before moving onto executive roles at Amazon.com and Salesforce, offered an interesting perspective given his work at the three tech giants.

In pitching his startup to Silicon Valley VCs, Khanna said that his Microsoft background was a “real negative” but his Amazon lineage was a “real positive.”

“Amazon still has a lot of cachet in the Valley,” he said.

Asked which company gave him the best footing as an entrepreneur, Khanna did not hesitate. It was most definitely Amazon.com, which drilled into him a customer-centric approach to product development.

“Amazon still tends to behave like a startup,” he said. “I can think of three or four things that I took away from Amazon, and still apply to my startup now.”

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