Business ResourcesChange Wave 003: Gary Ogasawara

Treehouse for Teams

Treehouse for Teams
writes on October 5, 2018

As VP of Engineering at Cloudian, Gary Ogasawara heads up a global team with operations in Silicon Valley, Milan, Tokyo and Beijing. His responsibilities cover product development, deployment and operations. Prior to Cloudian, he lead Engineering teams at various companies building search engines and real-time commerce and advertising systems. Gary holds a Ph.D. in Computer Science from the University of California at Berkeley, specializing in uncertainty reasoning and machine learning.

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Show notes:

Gary on LinkedIn

Gary on Twitter


Careers at Cloudian

The Checklist Manifesto: How to Get Things Right by Atul Gawande

Transcript, edited for clarity:

Ryan Carson: Welcome to Change Wave, an exclusive look at the real, first-hand stories of how cutting edge leaders rose to the top, smashed through barriers and created real change. I’m your host Ryan Carson, the founder of Treehouse, the company that’s taught 850,000 people to code. We also help companies like Adobe, Nike, MailChimp, Airbnb and more hit their hiring plans and create diverse teams. If you’d like to know more, head to

Today I’m joined by Gary Ogasawara from Cloudian. Thanks for joining us.

Gary Ogasawara: Thanks, Ryan. I’m a fan of the show, so I’ve been listening to a few of your podcasts, so it’s great.

Ryan Carson: Good to have you on the show. So, I’d love to know more about your job title and what Cloudian does.

Gary Ogasawara: Sure. I’m the VP of Engineering here at Cloudian. We’re about 165 total people right now, but I’ve been here when we were about 10 people, just starting out.

What Cloudian does is we provide software or also hardware appliance for scale-out file or object storage. If you’re familiar with AWS, Amazon, we provide an s3 API for enterprises, companies or service providers to store data — which could start from a few terabytes to now we have customers in the hundreds of petabytes of data. It’s growing amazingly, and we have some customers from across the spectrum. Saturday Night Live is an example; some of their video, all of their backed-up video assets are on us. A public radio station WGBH, like Terry Gross is also a customer. We have some cool customers like Formula One racing teams. They’re basically collecting all their data from their air tunnels, from even fluid dynamics in StarNet. We have state governments storing records. And then we power cloud storage for companies that are providing it to the end users, like NTT, and in Europe, and throughout. Companies like that. So, yeah.

Shedding work, letting go, allowing others to grow

Ryan Carson: I bet the audience would love to hear some of the stories behind that, so, and maybe this next question will reveal that. So the first big one I have for you is, I’d love to hear a story about a time when you encountered a massive barrier, either in your career or personal life, and how you tackled it.

Gary Ogasawara: I think it’s a traditional story, or traditional sort of barrier that a lot of people who study — we go through school, we study computer science, we become individual contributor engineers, and then the question is, after the first step of being an individual contributor to managing a team and that sort of goes well, but then at some point say, okay, we need someone to manage a huge team and to represent all of the engineering organization. That’s a real step, and I think that’s a real step or barrier, and then people who don’t do that — I mean, I have full respect for and do useful work, but I think the key is you have to decide you can’t do it all, right?

Ryan Carson: Right.

Gary Ogasawara: You have to shed some work or let some things go, and that’s a big step.

Ryan Carson: How do you let go emotionally?

Gary Ogasawara: I think you have to show trust in your teammates. It’s not much different from a team sport. You have to understand that people aren’t always going to do the same thing you’re going to do. It’s often not easy, and it takes practice, but you have to let go and allow others to grow.

Errors of ignorance and errors of ineptitude

Ryan Carson: Yeah. Gosh, that’s a good lesson. I’d love to know about your favorite book, course or person that’s affected you, influenced you in your career.

Gary Ogasawara: Sure. As far as work-wise, I’ve really been putting into effect this very simple but powerful book called Checklist Manifesto by Atul Gawande. He’s a surgeon, and he was trying to solve the problem of why in some hospitals, the surgery rate is much more successful than others, sort of for himself. The basic bottom line is make checklists and use them for different things, he said. There’s basically two types of errors, right? So there’s errors of ignorance, and then there’s errors of ineptitude. And most of the problems are the second type, “you know what to do, but you just don’t do it,” and that’s avoidable. I see you guys in this process going through a lot of that, you have sort of like a fixed process and go through step by step by step. So that book talks about how different domains apply checklists, like the pilots in an airplane before taking off. The building of a skyscraper needs to schedule a bunch of activities in sequence.

I’m trying to do the same thing in as many things as possible. So an obvious one is for a software release — we go through a checklist, right? “Have you compiled all the test results? Have you done the release notes review? Have you upgraded this cluster?” etc. etc., and we just go through those one by one, and then we can keep score then, too. “We’ve done seven out of 20 of the items, and this much remains.”

Ryan Carson: Yeah, that’s true, because it’s almost like operational excellence, you know? You can get all excited about innovation and creativity, but there’s a reality too, and we know the right things to do, are we going to be disciplined and do them?

Gary Ogasawara: Right, right. And then, another example, I think, goes to what you guys are doing at Treehouse, in terms of interviewing candidates — we want to make sure we’re applying the same criteria to all the candidates. So I personally go through a fixed set of questions and scoring scores of those, and go based on that.

Ryan Carson: Right. That helps you not veer off into questions that you’re interested in during the day, and-

Gary Ogasawara: Exactly, or your mood, or-

Ryan Carson: Yeah. You could be biased.

Gary Ogasawara: Biased, or-

Ryan Carson: That’s smart. Gosh. So The Checklist Manifesto is the book.

Gary Ogasawara: Yeah. Yeah, it’s a great book. I buy it for all my friends. I send it out, etc.

Ryan Carson: Make lists, and put me on them.

Gary Ogasawara: That’s right.

From butcher to VP of Engineering

Ryan Carson: I’d love to hear about the funniest, worst and most interesting job you’ve ever had.

Gary Ogasawara: It’s easiest to choose the worst: So, back when I was in school, in college, I had a job during a winter break in a meat shop, basically as a butcher. First off, you’re the junior guy on the totem pole, so you get these most mind-numbingly repetitive tasks, like wrapping things in the plastic wrap. Just physically, it’s in a refrigerated room, right, so I like to say it’s like physically-numbing and mind-numbing.

Ryan Carson: Sounds brutal. The reason why I ask this question is because I think it’s easy for listeners to hear about somebody like you. Okay, Gary has become an executive at a growing tech company, he’s taken it from 10 to 160. It’s intimidating, but it’s refreshing to know you used to work in a butcher shop. There’s a progression. These things can be done. So thanks for being humble about that. I appreciate that.

I’ve interviewed 50, 60 people now and no one’s worked in a butcher shop.

Gary Ogasawara: Yeah. It paid pretty well, so …

“Stay as deeply technical for as long as possible.”

Ryan Carson: So I’d love you to imagine that you hop in a time machine and you go back to earlier in your life. And you get out, and there’s the young Gary. What would you grab his shoulders and say, “you have to do this. You have to know this.” What are those, what are two-

Gary Ogasawara: Sure. I guess one of the things is to keep very technical. I have kids right now where one’s starting college, two more are younger. What I tell them is, stay as deeply technical for as long as possible. Once you build this really strong foundation, it makes it easier to branch out and do different things that you want. I think that’s really key and useful. I try to do that as well, today: Write code, read code as much as possible.

Ryan Carson: And what’s the why behind that? Why stay technical longer?

Gary Ogasawara: For one, it gives you a better understanding of the people you’re managing, so you could understand how difficult things are. I think one of the keys to management is, how do you estimate things and how do you predict “when is x going to be done?” That’s the basic question of management.

Ryan Carson: “When is x going to be done?” Yeah.

Gary Ogasawara: If you have a better understanding of what x is and what’s really involved to do x, then you could modulate the responses you get from people. With this recent Agile-type of software development that basically everyone is doing, it becomes this discussion of “okay, developer, how long is it going to take you to get done?” and you wait and sit and listen. You need some way to apply some standards to that — and without that technical background, it’s difficult. You don’t know when someone’s bullshitting you, you don’t know when people are too optimistic about, “oh, I’ll knock that off tomorrow and be done.”

Ryan Carson: Yeah. Right. You can’t do that.

Gary Ogasawara: Right.

Ryan Carson: Right, it’s impossible. I think we could abstract that it’s interesting, because I’ve had the same experience with sales.

Gary Ogasawara: Okay.

Ryan Carson: And it’s crazy, you know. And so for anyone listening that doesn’t happen to manage engineers, I think that lesson could be abstracted and say, whatever your profession is, because, I didn’t know how to do sales, and so I couldn’t understand what people were saying, or if it was realistic, or even have empathy.

Gary Ogasawara: Mm-hmm.

Ryan Carson: And now that I do it, it’s, you’re right. It keeps you in the craft of that.

Gary Ogasawara: Exactly.

Ryan Carson: And you can be a better manager, you can be more realistic, you can be more empathetic. So I think you’re right. That’s a great lesson.

The value of possessing deep knowledge on one feature of a project

Ryan Carson: So that’s lesson one. What would be the second lesson you’d grab your shoulders and say, “know this!”

Gary Ogasawara: I would go back to my thesis advisor back in school and he said, “In order to get a Ph.D. you have to be the world’s expert in one topic. So what is that going to be, and how are you going to do that?” That really stuck with me for a long time. You have to master a few topics. The more the better, but if you could be good in at least one thing or a few things, that’s very important. Even now, at Cloudian, we’ve grown and the product has grown, but I try to take one feature per release and work on that. When there’s questions for something on that, then I could be the expert in that one thing.

Ryan Carson: Got it. So the kind of generalized lesson is, focus on one thing. Get good at it.

Gary Ogasawara: That’s right, that’s right.

Ryan Carson: Yeah, yeah. Gosh, we’re so unable to parallel-process as humans, aren’t we?

Gary Ogasawara: Right. Right.

Ryan Carson: It’s unbelievable. “This is going to be all I’m doing.”

Gary Ogasawara: Yeah, and a lot of people can do up to a certain depth, but you need a deeper knowledge, and that makes you valuable.

Ryan Carson: Yep. Love it. All right. Thanks for sharing those two lessons. Those are valuable.

Gary Ogasawara: Sure.

Ryan Carson: I wish I could go back in time and tell myself those things.

If you can count things, you can understand things

Ryan Carson: What is a story where you caused significant change in your personal or professional life?

Gary Ogasawara: I use a phrase — again, that some mentor once told me — you should count things, and if you could count things, you could understand things. So I like to use that phrase all the time. You see it recently and all over in management by objectives, marketing metrics, things like that. It’s really important in as many phases of your life as possible, to count things and then you can understand it. You have the data, so data-driven analysis in that way.

Ryan Carson: Got it. What’s one of those things, one of those projects where you’re just really happy that you collected the data and used it, and learned?

Gary Ogasawara: So one of the things is customer issues. So your software’s out there, you’re getting bug reports — one of the things we pay a lot of attention to is, what’s the average age of an issue out there? So how long does it take to resolve? If you could keep a handle of that — and it’s not so much the absolute number, but the trend. If the average age of issues is growing, then you have to dig and see exactly what’s going on there.

Ryan Carson: Right. And then you have data and you know, and say, okay.

Gary Ogasawara: Exactly.

Ryan Carson: The average age of this issue is growing. This is a problem.

Gary Ogasawara: Right. Exactly.

Ryan Carson: Great. Well I really appreciate you sharing those life lessons and stories.

Gary Ogasawara: Sure.

Ryan Carson: It’s a really interesting picture into your life, and congrats on all your success. If the listeners want to get in touch with you personally, where are you on the internet?

Gary Ogasawara: You can find me on LinkedIn, just do a search for my name. I’m not that active but just do a few retweeting on Twitter @go10, so you can find me there.

Ryan Carson: Go10, that’s a good user name.

Gary Ogasawara: Yeah, just keep it short.

Ryan Carson: Yeah.

Gary Ogasawara: You can ping us at on the web, or We’re looking to grow quite a bit, so I appreciate people who are interested getting in contact.

Ryan Carson: Check them out. Well, thanks, Gary. Good to chat, and we’ll hopefully talk soon. Take care.

Gary Ogasawara: Thanks, Ryan.



talentpath, treehouse, diversity, tech, hiring plan, diverse team


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