Cloud to Ground Podcast Episode 7 – Derik VanVleet

Cloud to Ground Podcast Episode 7: An Interview with Derik VanVleet

On this episode of the podcastwe talked to Derik VanVleet from Cloud Sherpas about the “aha moments” you have in the cloud, why and how Google is winning the war against Microsoft and the future of backoffice IT. We had a really great discussion that all you cloud enthusiasts will enjoy! To hear more from Derik, you can visit the Cloud Sherpas blog or follow him on Twitter.

Andrea Bridges-Smith: Hi everyone, and welcome to another thrilling episode of the Cloud to Ground podcast presented by Spanning! If you’re using Google Workspace at work or at school or at home, make sure your files are protected by visiting and signing up for a 14-day free trial of Spanning Backup to see if it’s right for you. I’m your host Andrea Bridges-Smith, and with me today is Mr. Derik VanVleet, director of Cloud Strategy at Cloud Sherpas. Thank you so much for being on the show today Derik.

Derik VanVleet: Absolutely, thanks for having me.

ABS: So, as any seasoned listener or viewer of the show knows, we have to start out by establishing your cloud expertise. So how long have you been working in the cloud?

DVV: So I’ve been with Cloud Sherpas about two years now. Prior to that I spent a large number of years in the Microsoft ecosystem, sort of before cloud really took off. It was in the early Office 365 days, so back when they were trying to figure it out.

ABS: Okay. Great. You’ve got a couple of years experience under your belt, you’ve kind of seen the growth from infancy to– are we at maturity yet? I don’t know.

DVV: No, not quite yet but yeah.

ABS: We’re headed in that direction.

DVV: That’s right, it is more than just a buzz word now.

ABS: Absolutely, okay good, so it sounds like you’ve got some cloud experience under your belt, I am going to go ahead and declare you an official cloud expert and–

DVV: Fantastic.

ABS: There’s no medal, there’s no trophy, but the next time you’re in Austin, I will buy you a beer; in fact, I will buy you lots of beers–

DVV: [laughter] No problem, I love Austin.

ABS: So it’s not completely worthless.

DVV: That’s right.

ABS: So before we get to the good stuff, first of all let me say that I’m really excited to talk to you because we share a mutual passion which will get to later, but first of all, tell me a little bit about what Cloud Sherpas does and what you do over there. And just a quick disclaimer for all of our viewers and listeners, Cloud Sherpas is one of our partners and they are terrific people to work with.

DVV: Cloud Sherpas was founded in about 2007 by three guys here in Atlanta. We’ve quickly grown to one of the world’s leading cloud services brokerages. So we have three main industries – industry practices, that being Google, another being Salesforce and the third being ServiceNow. So, we are a pure cloud company, sort of born and raised in the cloud if you will. My role as director of cloud strategy is reporting to the office of the CTO, David Hoff, who’s one of the founders and my primary responsibility is around really around Microsoft compete for the Google business space, again, having had that background, so I do a lot of sales, training, education, kind of keep an eye on the market, white papers, blogs, etc.

ABS: Okay great, and I did a little bit of research on you online. Some people might call it e-stalking, I call it I just looked at your LinkedIn profile. So nothing too scary. But, I see that you used to be a SysAdmin back in the day and that role of course has some, shall we say unique pains that go with it. So how does that experience kind of play into what you’re doing now?

DVV: Yeah, so it seems like forever ago I was a systems administrator for a pretty large bank in the Southeast. So one of the advantages there is when I talk with customers or we’re talking with the system administrators or even the IT management team, I have direct experience dealing with the challenges that they have today. So some of the common terminology or common themes in terms of doing more with less and those sorts of things, I get pretty much get instant credibility because I’ve done it, I know what their experiencing and I know what they are going through in sort of this transition and this thought process going from on-premise messaging or whatever it is to the cloud or whatever they choose, then I can help guide them through some of that decision process as well as some of the things that they need to be on the lookout for.

ABS: This idea of doing more with less, that seems like it’s something that’s pretty universal to anybody out there. On our last podcast, we had a tech coordinator from a school in Colorado, and of course in the education world, they are always trying to do more with less, so is that something that you kind of see across all of your clients, pretty much with everybody?

DVV: Pretty much with everybody, right. In the cloud and cloud technology, the mass scales that you have today, if you think of Google Workspace and just the mass scale that Google has, companies now – CIOs specifically – are coming to the realization that ‘Hey, I am not an email company. I can’t do email as well as Google can. Why am I in this business? I can re-purpose those administrators to do– my company makes widgets, why don’t I re-purpose these guys that help find the best and most efficient way to make widgets instead of backing up my on-premise mail system every night?’ It doesn’t make sense and I think that they’re quickly realizing, based on the economies of scale, that it doesn’t make sense for them to be in that business anymore.

ABS: So what was it like moving from a traditional Microsoft-based IT setup to a cloud setup where you’re working now everyday?

DVV: So, the transition for me was pretty straightforward. But what I explain to a lot of customers is when you go from this traditional backoffice software environment – file server, SharePoint, email, and so forth – and you go to the cloud, you have these series of what I call “aha moments” where the way you used to do things, for example, accessing your on-premise SharePoint or file server, and you had to have your VPN client and you had to VPN in to access those resources, and now being in a pure cloud environment– when I was kind of going through my orientation, one of the first things I looked for is a VPN client and I have it, it’s like “Aha, I don’t need one, it’s all in the cloud.” It just works. So you have these, again these series of “aha moments” throughout. Going from organizing email and just being absolutely psychotic about creating folders or filters and organizing my email to going, I don’t organize anything anymore. I just search for whatever I’m looking for. So you just have these series of “aha moments” and incremental points of efficiency where, like I mentioned I don’t organize email anymore I just search, even if I don’t know what I’m looking for, I just type it in as if I were doing a Google search on the web. I don’t have to know what I’m looking for in order to get results and hone in on what I’m looking for. It was a very freeing reality, because again, I’m device-agnostic, I can be on the Mac, I can be on the tablet, I can be this mobile phone, I can be at a Windows PC. Here in the office I use primarily Chrome devices, Chromebook, Chromebox, and when I go to customers I think one of the more compelling things is I don’t always take a machine with me – a laptop – because I can just grab somebody in the room that brings one and literally just use any device that is there to do my demo presentation or whatever it is I’m doing. I think that’s pretty compelling for the customers as well because there is no way they could do that in the way they work today.

ABS: So just a quick note for the folks who are very OCD like myself, you still can organize psychotically if you would like to. I do that everyday. I have a lot of folders, so you can still do that with the cloud, so don’t freak out.

DVV: I started doing that, again coming from the Outlook world, I had folders from all my customers, rules based on where I was getting mail from or whatever and I just felt like “Wow, I’m here now, I should probably create all these labels and all these rules,” and I started doing it, and about ten minutes later I thought, “What am I doing?” And I just stopped and so now I search for everything. But that’s just something that I– that’s just me.

ABS: I’m the type of person that right now I have 20 emails in my inbox and it’s making me kind of itch a little bit. I got down to four last week so, if that tells you anything about how fun I am at parties. Also, what you were talking about with the “aha moment,” I definitely know what you are saying there because when I started working here in January of this year, I came from a very traditional Outlook/Microsoft Office kind of environment and came here. One of the things that was kind of my “aha moment” was I kept hitting Command-S to save my files, just out of reflex, because I was so used to losing my work, in the middle of it, that saving every so often had become this reflex, and so I kept doing it even though it wasn’t saving or doing anything. So, at this point I should probably explain the mutual passion that I referred to earlier. As anyone who has listened to or watched the show before probably has gathered, I hate Microsoft products and I think that they die constantly in the middle of you trying to get work done. They don’t do what you are trying to get them to do, even though the capability is clearly right there and it is supposed to be doing that, and I have spent a lot of hours saying four-letter words to my computer whenever Microsoft was involved. And I think the only another person who shares my deep passion for disliking Microsoft is Derik here. So Derik, tell us what you hate most about Microsoft products.

DVV: That’s pretty funny. Yeah, so I use the term dislike immensely, right? Try not to hate too much other than brussels sprouts I guess. But yeah, the one thing, that’s–  wow, narrow down to that. We have a guy in our office here that kind of– he’s got a shirt that explains it pretty well. He’s got a shirt that says “Patch Tuesday made me go Google”. I think that’s a huge thing for me is, they have all these different products in their portfolio, I mean they’ve got a bloated product set, and there’s a lot of duct tape and baling wire that happens in the background that keep these things “integrated” versus say Google, where they’re just kind of built from the ground up to be integrated. But the whole concept of having it reboot and patch, and patch and reboot, the patch didn’t work and so now you’ve got to roll back that patch– which they’ve been having a lot of problems with it lately. Just drives you crazy, you just want to turn on the device and connect to the internet and just have it work, without all this sort of client-side download this, flash that, those sort of things, and that absolutely drives me crazy. And after being out of that world now for a couple of years when I grab a Windows machine, nine times out of ten if I boot it up, the first thing that kicks off is Windows update, must restart and I’m going “Oh my gosh,” and then I just throw it back in the closet and give up. That’s probably the biggest problem that I have, if you made me choose one.

ABS: Yeah, I know this sounds like not the biggest problem in the world, but I really hate any kind of software update. It always pops up in the middle of me doing something else. You never log in to your computer to do software updates. You log in to your computer or your device or whatever to do something else, to get work done or to look at Facebook way more than you should be or there’s a lot of reasons. Software update is never one of them and so every time one pops up, you know it’s — okay, your user experience. Think about the user experience. This doesn’t fit into the user experience anywhere. And I love that Google has just kind of taken that away. I don’t know when they update stuff and I don’t care and I don’t know what updates they did and I do care about that, but I can read about it on Tech Crunch or on their blog or whatever.

DVV: That’s right. Yeah. It’s distracting for a user. You’re trying to do something and then boom, there’s the pop-up, there’s a new update. Again, really? And today is Tuesday, there’s all kinds of new ones coming out I’m sure.

ABS: Well, luckily I will not have pay any attention to that.

DVV: We’ll read about other ones that went bad tomorrow.

ABS: Yeah, exactly. So how do you think that Office 365 and Google Workspace stack up against each other in terms of the functionality that you get, as well as how well they perform?

DVV: How Microsoft 365 – Office 365 – and Google are different and work in the cloud. One of the biggest differentiators, for me between 365 and Google Workspace is the fact that 365 is not cloud technology, right? By Microsoft’s own admission, Office 365 is nearly the same software package with bits and bytes that you as the customer could install in your own data center and run. Versus Google which was built in this huge massive scaled-out multi-tenant environment, designed from the ground up as a cloud platform. What Microsoft is doing is really nothing more than hosted services. Hosted services with limitations. So, if you’re running SharePoint online, for example, or you’re running SharePoint on-premise and you’ve got a nice workflow, custom workflow or a custom application that you’ve developed on SharePoint on-premise, chances are you’re not be able to run that in SharePoint online because it’s restricted because of the multi-tenancy and just the overall architectural limitations that they have. They don’t allow you to do a lot of customization, versus Google which, one thing that customers leave aside pretty quickly or you just sort of forget is Google is a platform, the whole thing is a platform. You can customize just about anything in there you want, more so than you can 365. So, I think architecturally, it’s a huge differentiator and if you do some basic metric testing, it becomes very apparent. For example, just doing some basic monitoring of the two platforms just to get to the landing pages where you would log in. Microsoft is roughly somewhere between three and almost four times as long to get to their login page from the latency perspective. Now you think, that’s not a big deal. It’s a big deal. We just talked about user experience and today when people – because of Google now, when you type in a search and it says, 1,200 million results and in .20 seconds, right? That’s what people expect and when it takes you roughly a second and a half to load the login page to log in 365, users notice that. They notice that big time and that doesn’t even include logging in. The architecture and the massive scale are probably the biggest one. Microsoft likes to talk about Office 365, you don’t have to train your users, because they’re familiar with it, no. If anybody has seen the latest and this is crazy, they say the latest version of their cloud offering in 2013 is actually nothing like what most customers are on which is probably 2007 . Even if you’re on 2010, it doesn’t look the same, it doesn’t act completely the same. That is just absolutely false, and is a huge caution flag for customers. Those are some of the biggest differentiators, but you have time and availability which I’ve blogged about in the past and you can read about and how we’re sort of monitoring that. Microsoft is a little ambiguous in how they’re calculating that. For example, SharePoint online has been in a service degradation mode for six or seven days now, but they never call it a service interruption and they don’t offer credits on it. Why not? Yet they claim they have their 99.98% uptime. It’s just a little bit how they handle that and how they define that and what their definitions of that are. I always caution customers to take a look at that very closely, sign up for a trial account if you want, just so that you can see the dashboard, and just look at, there’s always dots everywhere constantly.

ABS: Yeah. Absolutely. I can tell you that in– let’s see, I’ve been here for ten months now, I’m working on Google all day everyday, and I think in that time there was about a two-hour period were my emails were delayed and that was it. And in the Microsoft environment the server was constantly– seemed like it was always going down.

DVV: Yeah and that’s again, from a user perspective if you look at their dashboard, they’ll see service degradation, email delivery timeouts, those sort of things. That’s frustrating as all get out to a user. Google recently had their low latency issue here and I think they deemed that as a service interruption. That happens every week on Microsoft platform and they never call it an interruption. They call it service degradation. So, be careful what you are paying for.

ABS: Well, that kind of starts to get to another aspect of Microsoft that I wanted to ask you about which is their culture, which you hear about some of their cultural practices and it’s a little interesting. I am pretty sure that you have heard of their stack ranking system with their employees.

DVV: Absolutely.

ABS: So, for anybody who is out there who might not be familiar with it, the idea is that everyone at Microsoft gets ranked in their team. So if there are four people on a team, one of them is the best and one of them is the worst, and two of them are in the middle, even though all four of them maybe really, really good at their jobs. So what do you think about that?

DVV: Yeah it sounds sort of good on paper and things have been pretty well documented in the last few months. It’s just from former employees and just the culture that it lead to everybody working in silos. So, if you and I are on a team and I have a great idea, my great idea directly correlates to my work performance review in my bonus, so why would I share that with you, right? Unless I’m just the nicest person on the planet. So, I think it means to this just the silos of people not wanting to collaborate with individuals and competition is only good if those who actually working before me are rewarded collaboratively and it just killed innovation. Nobody wanted to work as a team to get things done and so everybody was doing things individually. If you just look at their products in the last 10 years, almost, there’s not really much innovative things that have come out of that unless– the Xbox Connect is kind of neat. That’s not an enterprise thing, but if you work at the enterprise phase they haven’t innovated anything in a long time. It’s all been new acquisition and I think that stack ranking just crushed the innovative and collaborative spirit of the company and I think now that obviously Ballmer is leaving, that would be a subject for review and change as well.

ABS: Well, you know, it’s like they always say: working in silos is the future of the modern workplace. People say– no, no one ever says that.

DVV: [laughter] I was like, uh, are you going to quote your source there?

ABS: No one has ever said that. That was a thing that I definitely made up just now. So getting outside of Microsoft for just a minute, as much fun as it is to talk about them and I could all day. What other companies are out there in the cloud right now that you think are really doing some innovative stuff that we should keep our eye on?

DVV: Obviously Google is doing some pretty innovative stuff with their various projects, and Glass and so forth. I think one of the areas that I see a lot of opportunity as things move over to the cloud are folks, like yourselves, like expanding that are doing what it’s traditionally been backoffice sort of technology and importing it to the cloud. You see technology such as the backup/disaster recovery moving to the cloud, you see networking moving to the cloud, conferencing those sort of things. Because I think from an enterprise perspective, those are the sorts of things that people can relate to, like messaging is pretty easy, but at the same time you have the server-huggers that are a little bit scared. Server-huggers being the guys that want to go in and hug your server, they want to go to touch the server, right? They’re afraid to relinquish that power to the cloud. But slowly I think you’re going to see like I mentioned, Hey, we’re not in the email business, let’s move it to the cloud. I’m not in the networking business let’s move it to the cloud. I think those are the ones that come from a kind of innovative standpoint to keep an eye on, I think a lot of the sort of what’s next is probably not even thought of yet. There’s a lot of companies that are coming out with cloud-based office productivity suites, we’ve seen more of that. Google obviously and then Microsoft retrofitting Webex, Fox here recently and then a bunch of others. That is going to be an interesting space to watch. But I think those are migrating traditional backoffice technologies to the cloud are some of the big winners.

ABS: Yeah, that makes a lot of sense, it seems like the cloud lately is the answer to a lot of problems, and it is interesting to think about which problem it’s going to solve for us next. It seems like there is a lot of people out there kind of thinking about that and thinking about what are the pains in the neck that the cloud could make less painful. So I for one am thrilled that that industry is out there.

DVV: Yup. Absolutely.

ABS: Because, yay job security! Derik, this has been a fantastic discussion and I want to thank you from the bottom of my heart for being on the show today. Thank you so much for taking the time to talk to us, and for anybody who needs some help getting into the cloud, you should look up They are a wonderful company to work with. They will take your hand and gently lead you up in the mountain of cloud integration like a sherpa.

DVV: That’s right.

ABS: You see the idea. And they’re just generally a nice bunch of folks, you should definitely consider doing business with them. And to all of you out there in podcast land, I want to thank you for listening and watching. This show is really fun to do, and it’s nice to see people out there enjoying it. Thank you very much. As always, if you’re one of those people who likes having your files in the same place where you left them the last time you looked at them, please visit us at and check out a 14-day free trial of Spanning Backup to see if it’s a good solution for keeping your files safe and in the same place. My name is Andrea Bridges-Smith. Thanks for watching, and we will see you next time.