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Brian Valentine was a legendary figure inside Microsoft, as the executive leading the engineering teams for the Windows 2000 and Windows XP releases. He left in 2006 to work as a senior executive at Amazon, and has since gone on to join Napster co-founder Jordan Ritter at the Seattle startup Ivy Softworks.

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Brian Valentine

Valentine and Ritter joined us as our guests on the latest GeekWire radio show. We talked about a wide range of topics, including their venture and the state of the Seattle startup scene. But as part of the conversation, we couldn’t help but ask Valentine to reflect on his experiences at Microsoft and Amazon.

For starters, is he still using Windows?

“I am still using a Windows machine, but since some things we’re doing are cross-platform, I have a Mac, and I have an Android phone, my wife has an iPad, she has an iPhone, so there’s all kinds of devices in my life,” Valentine said.

OK, so on his Windows machine, which version of Windows is he running?

“On my work machine, I’m running Windows 7. On my home machine, I’m running Windows 8.1 — with a Start button,” he said. “I was a little bit upset, but not too bad, that I had to pay a small amount of money — like $6 — to get my Start button back … But other than that, I’m Windows 8 at home.”

His thoughts on Microsoft’s newly unveiled Windows 10 release?

“I think Windows is still very relevant in the marketplace. People still buy PCs, people still buy laptops. Microsoft doing Windows 10 is a natural thing for them to do. They’re not going to walk away from Windows at all. It’s a great business for them. Windows 10, from what I can tell — I haven’t played with it yet — is going to fix some of the things that were missed in the transition from the keyboard and mouse to Metro and back. Being very smart about whether you’ve got a keyboard and mouse, vs. a tablet, and being able to auto-switch between that is a great idea.

“If you look back, it probably should have been done on Windows 8, but you know everybody makes mistakes — or misses some things, I won’t call them mistakes, but they missed some things — but they’re fixing those, which I think is great for the company and great for the people working on that product.”

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Jordan Ritter, left, and Brian Valentine of Ivy Softworks in the KIRO Radio Studios (Erynn Rose Photo).

Valentine talked about the transition from those big companies to Ivy Softworks, saying it has been refreshing to work directly with engineers in the trenches, and even write code himself again. When Valentine arrived at Ivy Softworks last year, Ritter gave him a project to write in Ruby. We joked on the show that it was like a hazing ritual.

“It was!” said Valentine.

But he said the change has been refreshing. “Before I had VPs working for me, who had directors working for them, who had Level 8s working for them — four levels, five levels, six levels of indirection between me and where the work really got done. Now I get to be where the work gets done again. It’s given me a whole new shot of energy.”

Sure, but he had a reputation for being real at those big companies, using humor and stunts to keep things light and motivate his teams. He wasn’t exactly up in his ivory tower.

“I always stayed as close as I could, but this is a whole different level of closeness. I would do reviews of architecture meetings with software architects, where now I get to sit with a developer and do code reviews and be with them while the code’s being written, as opposed to just being a reviewer.”

“I’m never afraid to have a great party. I’m never afraid to do stupid stuff. We can still do that at Ivy Softworks, there’s nothing wrong with that. I will dress in whatever costumes I need to dress in, I will stand on my head and drink beer if I have to. All those kind of things are all still part of me.”

How cool to know that Amazon didn’t suck that out of him, I said.

“What are you trying to say?” he asked.

From the outside, I said, Amazon comes off as very sterile. Not a lot of fun. Is that a misperception?

“My organization inside Amazon always had a lot of fun,” he said. “Here’s the difference: I could build up great, big ship parties at Microsoft, because it would take us two to three years — sometimes a lot longer — to get stuff out the door. So we had these long product cycles, where you could build up a huge amount of pent-up energy in the march to get to the end, and you’d have this big blowout at the end. Legendary parties that we would have.”

“At Amazon, things change every day. So there’s no one big event. In the device world, they have device shipments, but those are remote, and they don’t tend to be organized the way Microsoft was in that way. But in the software side of Amazon, you don’t have these big events, and so you don’t have the opportunity to have these giant party, but you still party, you still have fun. But it’s on an iterative scale. It’s an evolutionary party scene vs. a revolutionary party scene.”

In other words, you read the positioning paper, and then you party, I joked.

So seriously, what was it like to work for Jeff Bezos?

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Amazon CEO Jeff Bezos

“Oh, actually, I’m not sugar-coating anything here,” Valentine said. “I had a lot of fun working with Jeff. I’ve worked for Andy Grove, I’ve worked for Steve Ballmer and Bill Gates, and I’ve worked for Jeff Bezos. All three very successful founding CEOs that created very successful companies. All four of those people were definitely different in their styles, their personalities and everything else.

“Jeff doesn’t yell at you, he doesn’t do those kind of things, at least I didn’t see those things in my tenure there. If you do something wrong, it’s more like you disappointed your parent. That’s the feeling he can make you feel. Which is just as bad as getting yelled out, to be honest with you.

“But he’s brilliant. I always told him that the day I’d quit Amazon — which didn’t actually come true — is the day that I went to three meetings in a row with them where he didn’t tell me something that he didn’t learn. I wanted to be smarter than him for three meetings in a row. …

“Brilliant guy, really fun to work with. The big laugh is legit. Likes to have fun, and he taught me a lot.”

That was just a small part of our conversation, which focused largely on Ivy Softworks and and the state of the Seattle startup scene. You can listen to the whole show below. The conversation with Valentine and Ritter begins in the second segment, at 9:30 in the audio player below, following our weekly news roundup.

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