Scott Olechowski

Scott Olechowsk, Co-Founder & Chief Product Officer at Plex, operates one of the most successful global streaming media services available.

With countless different devices all storing personal media, the need to design a system that would allow for communication across platforms became increasingly apparent to Scott Olechowski, Co-Founder & Chief Product Officer at Plex. Join Alison Dean as she and Scott explore his experience in the world of cybersecurity and software development, and how his desire to create a simple and effective streaming solution evolved into one of the best media server apps available.

About the Guest

Scott Olechowski is Chief Product Officer and Co-founder of Plex. He is responsible for driving the product strategy, product management and business development for Plex’s suite of personal media software and services.

Over the past fifteen years, Scott has applied his entrepreneurial know-how and spirit to a number of software & Internet focused start-ups. His professional experience includes executive positions in product strategy, business development, marketing, and international sales for a number of established brands such as Cisco, PostX and IronPort. He is an expert in cryptography with six issued encryption and authentication patents, and was a technical and thought leader in Cisco’s global threat intelligence operations. Fresh out of college, he co-founded a video software company that pioneered the synchronization of video testimony and official transcripts, which dramatically improved conviction rates for trial lawyers.

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Alison Dean (00:09):

TheoremOne is the leading innovation and engineering firm for the fortune 1,000. We design, build, and deliver enterprise-scale technology solutions and are very excited to present The Breakthrough Podcast. An ongoing series where we interview technology leaders to share their experiences and perspectives on what's next in tech.

Alison Dean (00:38):

Welcome to The Breakthrough. I'm Alison Dean VP of Operations at TheoremOne. Today we are talking with Scott Olechowski, currently the Co-Founder & Chief Product Officer at Plex, which according to happens to be the best media server app that you can get. Scott sent me this quote from Mark Twain, "Continuous improvement is better than delayed perfection." So hello, Scott.

Scott Olechowski (01:03):

Hey, Alison. How are you?

Alison Dean (01:05):

I'm good. What does that quote mean to you?

Scott Olechowski (01:07):

To me, it's the heart of what we do in software in particular, but just in product, generally, you have to ship. You have to get what you're doing out there and it's never finished. You're always improving it. You're always working on it. You always know you can do better. You always know you're going to get feedback. To me, it's just that ethos of you're never done and you're just getting started every time you ship.

Alison Dean (01:30):

I can only imagine as someone that leads product for a company that when you're looking at anything now in your life, you're literally thinking, "Well, I would improve this here. I would improve that there."

Scott Olechowski (01:42):

Certainly, when it comes to stuff closer to my domain in the software app realm, that sometimes does do that or I'm like, "Oh, phew, glad we didn't do that." And then other times it's like, "Oh man, we should do that."

Alison Dean (01:54):

I'll take that.

Scott Olechowski (01:55):

But outside of my domain, when it's like eggs at the grocery store, I'm usually just like, "All right, these are fine, I don't know."

Alison Dean (01:59):

No. I think anything in the world of your computer screen, if you're going somewhere and checking things out, I can imagine how the brain is going all day long.

Scott Olechowski (02:11):

I'll tell you a funny story about that. Our users, they're fanatical about Plex and they just love the product and they're amazing, and they're not afraid to tell us what they love and tell us what they hate and if we screw something up, they make sure we know. It's actually a great part of what's been built by us in this community. But if we move some cheese, you'd think we like slapped their grandmother or something like that. It is like visceral sometimes and we're always like, "Man, they just don't ever give us a break." But then we use products like Slack and other stuff. And when they moved the cheese, you should hear our team bitch and moan, we’re just as bad when it comes to that thing too. So it's definitely a two-way street out there.

Alison Dean (02:52):

So as CPO, I always think it's nice to hear what a typical day looks like so that people

listening to have some context.

Scott Olechowski (03:00):

So I will just clarify. I'm one of the co-founders. I run product management, but I also own business development, which has all of our strategic alliances and partnerships and things like that, as well as what we call shared services, which is our customer success team, our quality assurance team, all of our metrics, infrastructure, and reporting both for internal and our partners as well as our ad operations team. So it is like an array of different stuff. I don't run engineering, I don't run finance and I don't run marketing, but a lot of the other stuff I own in some way.

Scott Olechowski (03:30):

So most of my days are full of meetings, literally what it's become now as I'm sure most people watching and listening probably feel like all they do is sit in meetings. There's a lot of coordination, right? We're always trying to move fast. We're always iterating. We're always working on new things. We're maintaining existing things. We're running a business. We're hiring people.

Scott Olechowski (03:49):

So a lot of it is taking that muscle on the board. So we got the board-level objectives. We've got exact team coordination and objectives and goals and planning, which includes budgets and figuring out where to invest and all that stuff down to, "All right, we're going to hire an individual contributor. What type of candidate are we looking for? What type of role are we trying to fill?" And then there's just a lot of execution-related stuff, ensuring sure the team has what they need to get stuff done, and doing it in the best way possible and managing resource constraints. Because like every other company on the planet, I think we're always feeling we want to do more, but then we're trying to figure out where those resources are going to come from and what the trade-offs are.

Scott Olechowski (04:26):

So there's a lot of horse-trading going on all the time, which is fun. And then looking at the market opportunities, trying to assess where we should be going and where the puck needs to be as we go. It's a lot of decisions in coordination, right? Execution and assessment are the balance that I'm going through all day. It is tough because the context switching from this hour to the next hour, to the next hour, all over the place, which I'm sure everyone is experiencing.

Alison Dean (04:51):

I do really wonder how to address that harmoniously because it's so true going from meeting to meeting and needing to turn your brain on in different ways, depending on who you're talking to. When I was in college, I was a waitress for many, many years. Just needing to go from table to table and knowing how to react instantly. So maybe I have a knack for it, but it's definitely a problem. I agree. I wonder what the solution is for this and not to say that I'm asking you for that answer, but I think it's a good question.

Scott Olechowski (05:20):

Oh, I think it is. And I will say this, I've never waited tables, but I know I couldn't do it. It's like one of those things like why you tip well. I'm like, "Listen, I know I couldn't do this. There'd be food everywhere at the wrong places on people's laps." I have a huge amount of respect for people who can do that. I get bored. My attention span has shrunk over time. I admit that. So I actually enjoy the context switching and building those muscles, but it is tiring. I know I'm not doing as good a job as I could be if I was giving myself more dedicated time to focus in certain areas, but then I start to view my role now as making sure that I have a team that can do that. I'm there to help make sure my teams are successful with the things they're doing and I'm clearing the way for that and giving them the structure they need. My co-founder, his name is Elan. He's now our CTO and he's a developer, right? He's coding all the time.

Scott Olechowski (06:06):

It's just a fact, if you're writing complicated code, you need a lot more time to focus. There's some article I came across, I couldn't tell you who wrote it, but it was about managers versus makers and creating time for makers. People who are building things. So we actually instituted this thing where it's certain days of the week when people are expected to be available for meetings. But then there are other days of the week where engineers are allowed to make and carve out time for them to not necessarily have this context switching, setting meetings effort.

Alison Dean (06:37):

Two big thumbs up to that idea. I like it.

Scott Olechowski (06:39):

Yeah, it doesn't work. I mean, one of our biggest challenges as a business is we're a remote company from day one. I'm originally from Chicago. I moved to the Bay Area of California. So I was living there and my co-founder was in Maui. He lives in Maui. So we started this thing as a hobby, and it eventually grew up, but we started it. We had an ocean between us when we started the company. So we started online, but thankfully all these tools were coming along at the same time to make it possible to do something like that. So now we have employees in almost 20 countries around the world. We have headquarters in Los Gatos, California, but only a handful of people ever work out of there. It really is this remote work thing.

Scott Olechowski (07:19):

That changes a little bit to how you have to operate, and our biggest issue is time zones. Everyone, in general, loves the remote work model, but there is no question that time zones become a challenge. Like you end up with these certain people who they'll work in the morning, and then they will do their family stuff in the afternoon and the early evening, and then they're back on meetings into the late evening, and then it starts over. And then there's some of us that's like all in the mornings. You get these times that get contentious based on where folks are if we can solve time zones.

Alison Dean (07:46):

That's it.

Scott Olechowski (07:47):

No problem.

Alison Dean (07:49):

Let's just figure that one out. So you've definitely done a lot in your career. You founded a video software business right out of college. You managed biz dev at Cisco, and now obviously, as co-founder for Plex, you've seen a lot of things. You've done a lot of things. What do you think is the most crucial aspect of a company's IT strategy?

Scott Olechowski (08:08):

That's a really good question. So when I started my career, it was me. For beer money in college, I would write databases for people and companies and stuff that just needed to manage data in a way. Sometimes it was simple billing systems, but other times it was way more complex things, but it's usually solving some business problem that they weren't ever going to have their IT group build. So I would come in and build a little app, and it was great because they could do something quickly and solve a problem. But at the same time, I saw the other side of it: they let some kid come in and start writing software that snuck in the back door and ran on these systems inside their house. So it gave me a little bit of, "Man, these are big companies, Fortune 100 companies, and my software is running inside there now, and I haven't even graduated from school yet, and I'm not a software developer. What's going on here?"

Scott Olechowski (08:56):

As things are getting more connected, the internet was really making things possible there. So it was a little different security problem, right? It was almost more of a physical security problem than it was a cybersecurity issue, but it was laying the groundwork. What software should be allowed in? What type of rigor should be applied to what's allowed in and who should own these things, right? Because what might be totally secure today, maybe wildly insecure tomorrow, and who owns it? So from a strategy perspective, the tools are available now to do a lot of what people need to do in a wide variety of different ways. Some of those tools are really well-designed tools that are designed to be secure and be scalable and managed and all that stuff, which is wonderful, very different from me writing a database that would get dropped into some big company and who knows who wrote it or where it came from.

Scott Olechowski (09:46):

So that part's good, but still, because things are moving so fast and so many different people can now write software and throw it in the cloud, you start to see this patchwork of things that can lead to real issues, right? From a strategy perspective, you have to understand that, or you have to understand where the risk is. Where's the sensitive stuff? What's it connected to? How could it be compromised? Where can it come from? Because again, I think we're in a different place from IT. A lot of the tools are out there and the means to get what you need built. People can figure that out and there are a hundred different ways to do it, but 90 of those might be dangerous a year from now or 10 years from now. Security is a big part of it and it's just part of my DNA, not to the fault, I'm also a business person and a product person.

Scott Olechowski (10:24):

So I'm like we have to get stuff done and we have to do it in smart, reasonable ways, but we cannot just start to introduce these back doors into our worlds that we don't understand, or we don't have a plan for. So there is just this component of that. What I've been really lucky with is throughout my career, finding people who do value security, but also value business productivity. So it's nice ying-yang of putting the two things together. Not just security for security sake and not just productivity without thinking about security.

Alison Dean (10:52):

Yeah. This is the dance that I do every day. Let's talk about the biggest project that you've spearheaded.

Scott Olechowski (10:59):

I could probably come up with a number of interesting projects that I've been involved in over the years. When I was at a company called PostX, we did a secure communication platform, an enterprise software company focused on secure email, secure communication. We were trying to take something that was really technical, like photography and security and all this stuff and make it available for mass consumer usage. Customers were folks like Schwab and HSBC and Citibank and lots of big financial institutions, healthcare institutions, insurance companies, and one of the big ones was Chase. And they realized, "Oh my gosh, we have all these divisions, all these different use cases. We need a platform for secure communication that we can use internally with partners, with external associates, and with customers that scales that meets our standards, has all the controls and things in place."

Scott Olechowski (11:50):

So we actually ended up winning that business and took years to win and it was a very specialized sort of thing, but that was a pretty big transformation project, as well as an infrastructure enablement IT project there. Almost every group had inputs into this. So that was an exciting one. And then internally here at Plex, we historically have been focused on people's personal media, but over the last several years, we're getting more and more into cloud streaming media. We started with music and we had some other news and web shows, but then our big effort that came together was our Avon launch at the end of 2019, where we launched with a whole bunch of studio partners, Warner Brothers, and MGM, and Lionsgate. And now we've got almost 20,000 titles available on-demand for free all over the world. That was a big effort. It was a BD effort to go and get all these deals in place with the studios.

Scott Olechowski (12:44):

We had some third-party platform stuff that we brought in to help us deliver on this solution. We had all of the work on our clients and the user experience team and the client development, got a bunch of backend stuff. We had to get all of our ad operations in place and do all the deals with all the ad partners. We had to get all the reporting in place and all the portals so partners to come in and see how they're doing. And we had the instruments, all this stuff. That was a massive, massive project from inception, understanding the business model, getting all the partnerships in place, and then building all the tech and delivering it. And then it's an iteration we had never done.

Alison Dean (13:19):

Is there a reason why someone shouldn't be using Plex at this point? It's free. You have 20,000 titles that are free. I feel like everyone should have Plex in their lives.

Scott Olechowski (13:32):

I think you and I are in violent agreement. So historically, it's been helping people manage their personal media. So people would take their CDs and rip them or their DVDs and rip them. And then our media server software would scan that in and you'd get these libraries and we'd get all the metadata and we'd make it streamable anywhere. In the home, outside the home. That's all free. Like you can do everything I just described for you. And then if you want to sync it to your mobile device and take it with you on a plane, we have a feature that allows you to use an antenna and get terrestrial broadcast TV, right?

Scott Olechowski (14:01):

So in the US it's ABC, CBS, Fox. So there's a couple of features that we have that are valuable features that you need a subscription for. But a lot of people use it completely for free, which is great. And it does a lot. It really is a nice polished experience for that. To me, that's just one of the pillars of this thing. We have a relationship with the company called TIDAL music streaming service. We can sell that service to you, or you can bring your existing titles subscription in, and now you can stream that inside of our apps, it'll augment your personal music collection. So if you have that CD collection. I can't buy CDs anymore. I'm not even sure.

Alison Dean (14:36):

You can.

Scott Olechowski (14:36):

Okay. You're pushing it, but let's just imagine a world where you rip that CD collection and you have the U2 albums up to Joshua tree, but you don't have the rest. What we'll do is we'll fill it in with the title collection. So you're bridging your collection with the stuff that's available online. So our ethos. Just make it all come together in one place. You don't have to go to 80 different apps to get the content you want. So now with all the free ad-supported stuff, by definition, most of this content isn't available on a paid service. It's the way the studios make this content available. If it's in a subscription service, it's not available free on-demand and vice versa.

Scott Olechowski (15:10):

All these titles that we have are not available on Netflix, not available on Amazon or whatever. So it's a great compliment. We're not trying to replace Netflix, but it's a perfect compliment for things like Netflix and Disney+.

Alison Dean (15:21):

Hear that everyone, get your Plex subscriptions today. It just made me think of Amazon Music. So typically, I buy my CDs via Amazon, and many of them are then made available in their Amazon Music Player. So CDs that I have a hard copy of go there, which is cool. When you were working on everything at Plex, did you leverage any outside consultants at any point, or did you choose to do everything in-house?

Scott Olechowski (15:50):

That's a good question. So we actually have an interesting model on how we've hired a lot of our engineers in the past. So because we're remote and because the bar for being an engineer here is pretty high, what we often have done is use contracts and consultants as a funnel to full-time employment. So you'll find that most of our engineers have done a stint with us as a contractor, as a consultant. And usually, we try to find a project that can be done in a month or two. So it's usually not something massive thing. It's a part of a bigger project typically, but then we get to work with them. We get them into Slack with us. We have all the agreements in place that enable them to contribute code. And then we get to work together for a little while and be like, do they like working with us? Do we like working with them? They bring in something special to the table, all that.

Scott Olechowski (16:35):

So in that way, we've always had this influx of people contributing and us working together to figure out is this going to lead to something bigger? And some of those folks stay on as contractors because they're not ready to do it full time, or they have a couple of other contacts they are doing. If there's something that we need to do, there's typically a service or a platform that we can plug in to augment. And we'll do a lot of that integration on our end ourselves. We view a lot of what we do as really critical to the long-term business. We haven't just outsourced. Here's a project, go do this project for us because it's software that we're going to be maintaining forever.

Scott Olechowski (17:08):

It's pretty unusual for us to have a piece of software and then we don't touch it again. We've actually licensed code from third parties in certain cases where we're able to bring in libraries and bring in even big chunks of code and take ownership of it and do that. We're not opposed to the shortcut if it makes sense and/or the augmentation if it makes sense as a software company that hasn't been a big part of what we've done historically.

Alison Dean (17:31):

Yeah. So you spoke earlier about continuous improvement almost with how you approach products. How has Plex's UX/UI evolved over time? All those changes were driven by your users solely, or was it internally? People were saying, "No, this is definitely a problem."

Scott Olechowski (17:52):

Yeah. That's a great question. So we're users first. This is one of those great jobs where I use our software almost every day in some form or other, whether it's in the car, listening to music, or if it's watching a movie on the weekend or whatever. So a lot of it does come from that organic internal stuff. We have forums that our users can go and engage in. I have handwritten letters where people are asking us for features and tweaks and stuff that comes from all over the world. I mean, they feel a part of this community and it's really great to get that input.

Scott Olechowski (18:19):

So definitely a decent portion of stuff does come from users through various different means. The biggest challenge that we have is, it's very difficult for us to pre-announce big projects. "Hey, we're thinking about doing this Avon thing in two years, or, Hey, we're thinking about adding this music service and sometime over the next two years." We can't really pre-announce that stuff. Sometimes these things will happen. They will come to fruition. We don't know when they might,  if they do. There's a bunch of unknowns when you're building things and you've got a lot of competing priorities and sometimes even just business issues that might halt you for some period of time or whatever.

Scott Olechowski (18:52):

We have an internal north star of what we want to achieve as a business on our mission here. And our mission is, we want to bring as much content together in one beautiful, smart place as possible, but that's not going to happen overnight. That's going to take a lot of not only development work, but also lots of partnership works, and a lot of business model understanding like, "Okay, does that work? Where do we start? What do we do first? What do we do next?" All that stuff that needs to happen. And the big changes we've made to the user experience are based on where we're going and prepping on where we're going.

Scott Olechowski (19:20):

I think a lot of companies struggle with this, right? Like, "Why did they add this new thing here? Why did they change that thing there?" Well, I'm pretty sure most rational companies aren't doing that because they were bored. That's not typically the reason. It's usually because they have to change something to get to where they're going, and this is just an adjustment along the way. So there's been a lot of that, but I will say user experience is one of the core competencies as a business that we have. So we've got an amazing team there, and they are juggling where we are today with where we're going, and there are always trade-offs, but I think we've trended well.

Alison Dean (19:50):

I guess my question then would be, you must be on those forums saying, thank you for that feedback.

Scott Olechowski (19:55):

We do as much as we can. The problem is that the more attention we divert to that, the less we can build on things. So it's like, life's a balance, man.

Alison Dean (20:03):

Well, that's so true. I mean, that was a role at some point, right? When forms were so big.

Scott Olechowski (20:07):

Our team is actually pretty good about engaging there. It's tough because, again, everyone's got work to do. There's not a day that goes by that I don't somewhere get alerted to some discussion on the forums that something's going on and we need to think about, or we need to address, or we need to get on top of, or we need to explain. Sometimes just because of non-disclosures and things we can't explain what's going on. And that's so frustrating because it's like, "Oh, I wish I could tell you."

Alison Dean (20:29):

Well, I guess it's one of those things when a big release happens and then you're getting all that new feedback. "Oh my gosh, the thing that I asked for." However long ago, it was.

Scott Olechowski (20:37):

You could let it get you down or you could let it excite you and I choose to let it excite me. Whenever we launch something and we do scratch that itch for some portion of people, the only ones that are popping on our Facebook or Twitter or our forums or whatever is the people who want the other thing that we can build for them. So it's like, "Oh great. You care about this thing." And then it's one of those arguments where something goes wrong and 11 people tell their friends versus…

Alison Dean (21:02):

Something goes right and no one says anything. Yeah. Right.

Scott Olechowski (21:05):

Exactly. So to me, it's part of the joy of it is like. Like, I know they wouldn't take the time to moan if they didn't care. So I know they care.

Alison Dean (21:14):

They care. How much does AI and machine learning play a part in the user's viewing experience?

Scott Olechowski (21:22):

I think it's starting to play a much bigger role. We live in this golden time where there is so much content available to us. And the reality is what you're into and what I'm into, that Venn diagram may overlap but the reasons why it overlaps might be wildly different. I think that's where machine learning can help us help each other find those nuggets out there. I view my leisure time where I'm going to consume some of this content as some of my most sacred time and the amount of time I spend figuring out how to spend that time makes it painful. And I know that is definitely a first-world problem, but it could be really enjoyable. And instead, it's sometimes very frustrating, very painful, right?

Scott Olechowski (22:03):

So we're independent. We don't make content, right? So I'm not trying to sell you the next Batman movie or anything like that. Our job is to help create a great experience where you can get to what you care about efficiently and find more. And that I think is where the machines can help us.

Alison Dean (22:19):

Yeah, absolutely.

Scott Olechowski (22:20):

AI, machine learning, whatever we're going to call these different things. We were starting to see the recommendations that we're using are powerful because it's 20,000 items or whatever the number is going to be a year from now. It's just too much stuff and we need help. We need guidance and it feeds something that's smart that can help guide you to it. So I think that's our role over time. To me, it's a really valuable hole that needs to be plugged. Netflix does an awesome job on Netflix, right? Disney does an awesome job on Disney. They really make a good effort at trying to recommend stuff to you, but they can only do it for Netflix. They can only do it for Disney. We really need something that spans these universes that understands me. That's to me, the future and I don't think you can do that without AI and machine learning and other stuff.

Alison Dean (23:04):

I see that coming sooner than we think. The recommendations are getting much more spot-on, just because of everything talking to each other. I say a word out loud and suddenly there's an ad on my phone. I'm like, "Really? Okay." How has Plex changed with COVID and was there a correlation between the pandemic and viewership increasing?

Scott Olechowski (23:27):

A couple of things when we talk about COVID come to my mind. one is we’re a remote company, so we didn't miss a beat. If anything, we had one of our most productive years in the history of years. It was unbelievable. People started to get burned out a little bit though and I think that was generally universal. What was funny is some of our partners in the studios and other places, they were not ready. They have systems that were locked down. You couldn't access some backend system unless you were on-prem. Very, very secure. I mean, think about the content business, right? You can't have this stuff floating around willy-nilly. So they really struggled. There was like a month or two where things ground to a halt because they had to somehow change the way they were.

Scott Olechowski (24:08):

So for us, it was almost an accelerant on the development and business side. Some challenges with some external parties. Yes, there was no question. People were locked indoors and their TV became their best friends. For sure, it fueled a lot of viewing on our platform and everywhere. We were one of the few industries, I think that somehow benefited, which doesn't feel great when looking at some of the devastations out there, but it's also nice to know that like, okay, we gave people some ways to unwind and take their mind off of things and all that. In a way it brings you together, right? When you realize everyone is struggling with that. So folks in Romania and Brazil and Hawaii and Alaska, these are people on our team and we're all having this shared experience. That's fascinating, but what it really did was our folks really wanted to somehow give back.

Scott Olechowski (24:57):

So our roadmap got completely rejiggered. So one of the big features that we launched was this thing we call watch together. So the ability to let you and I, no matter where we are in the world, invite some other friends even and have a bunch of people watch a show completely in sync.

Alison Dean (25:12):

I love that.

Scott Olechowski (25:12):

Because people got separated and there were folks that were writing in like, “My girlfriend and I can't see each other. Man, we're in the middle of the Sopranos and we can't finish it." So that was actually fun to see our team rally and people work nights and weekends to get that done and get it launched and make it available to folks and the reactions to that were super great. We had a lot of schools that suddenly had a shift to remote learning, and there are actually quite a few schools around the world that use Plex for distributing media to their students. Letting teachers drop things they've filmed or made.

Scott Olechowski (25:41):

They don't want to send kids off to YouTube necessarily, or other things. So having some way to distribute content securely without entering the naked web. That is valuable. But all of a sudden what was on-prem is not remote and they needed to invite a bunch of students and do all this stuff to do it remotely. So we basically said, "Listen, if you're using it for education, we will help you." And we had a whole bunch of schools come and ping us and we helped them get their systems set up and do that. And again, this was like nights and weekend work from our team. It was like little, extra above and beyond. We decided to make the live TV part of it free while this was going on to it, just to give people a little something. So it was nice to be part of helping people cope and helping people get through a grind.

Alison Dean (26:22):

Yeah. I think that's a big deal. Were you hiring a lot in 2020 or was hiring the same and just you guys were working more hours?

Scott Olechowski (26:29):

We pumped the brakes. We honestly did not know what was going to happen. So as an executive team, the board, we said, "We're going to pump the brakes on spending and hiring and everything because we just don't know." I'm glad we did. It really brought us together as a team. This is the boat, this is the team, and we got through this. I think everyone's really proud of what we achieved.

Alison Dean (26:49):

What has surprised you the most about Plex's journey to date?

Scott Olechowski (26:53):

We started this as a hobby. The story here is I have five kids and I've obviously been doing software my whole life. I was living in Chicago and moved out to the Bay Area in California. And when my son was born in 1999, I bought one of the first digital cameras. So I started to take photos and had videos, had my MP3 collection now. I'd ripped all my CDs and had that to keep us sane while raising these kids. And then the kids always wanted to watch the same DVD again and again, and then they would use them as frisbees and weapons and stuff. I was buying the same DVDs again so I got those stored digitally. Then I had the digital media collection, but literally almost no way to consume it.

Scott Olechowski (27:32):

So I eventually ended up where somebody I knew was getting rid of these servers because they were replacing them. I was like, "I'll take one, put it behind my TV." I had a server-like fan going and had it plugged into the old TV. This was before flat screens. I had a wireless keyboard and it was running windows and like, "Oh, isn't this cool?" I get to look at our photos, listen to music and play a movie. But it was all like using windows Explorer and a mouse. My wife was just like, "Dude, no. Okay that it's on the TV and coming up the stereo, but the keyboard on the couch with a mouse and all this stuff?

Scott Olechowski (28:02):

“This is no bueno.” That was when I decided, "All right, there's gotta be a better way." So I basically went on a hunt. We found this open-source project and it fit the bill. And that led to me meeting Elon and us collaborating on this hobby and just basically put it out there in the world and people started saying, "Uh, this was pretty cool." This was before the iPhone was out. This was even before Netflix really started streaming and stuff like that.

Scott Olechowski (28:25):

But we started to see, okay, apps are going to be available on these devices. So there's going to be more and more apps. We should be one of those because one of the options was, "Well, should we built hardware?" We were like, "First of all, we're not hardware guys." That takes a lot of money and we love software, right? And we think these things are going to open up and we'll be able to get our apps on these things. Someday on X-Box, someday on a PlayStation, someday on this... and Roku started blowing up. So we were able to draft off of this expansion of what was available and what was happening. So I think my biggest surprise along the way has just been how we've been able to build a business that started as a hobby.

Scott Olechowski (29:00):

We weren't even sure when we started the business, what the business model was going to be. LG Electronics called us up one day and they're like, "Listen, we want to fly you out to Seoul, Korea, and have you present to our CTO." It was really huge. I would take some time off of work and go. I was at Cisco and by the end of the day, it's like, "Okay, we want to invest. We want to do this. We want to have this at CCS and do a demo." And we're like, "We haven't really formed a company. I'm not sure we want to." Because again, we just weren't sure what it was going to be as a business. So we took a little leap of faith and we've been taking these leaps of faith along the way and we keep on hitting some solid ground.

Scott Olechowski (29:29):

Some of that's luck, some of that's just brute force, some of that's careful planning. You know, I think our community has helped us get there, and our team. I mean, our team is willing to take those risks and push and figure things out along the way.  Knowing that version 1.0, the version that we need. It's version 1.1, 1.2, 2.0 and we just keep iterating and get there. So that's been fun. You don't know exactly what this is going to look like, but that blurry vision has always been the same. We want to solve this problem in this space and we're going to find a way to get there and do it our way.

Alison Dean (30:00):

Right. So Helen Norris, who's Chief Information Officer at Chapman University. She was recently on the podcast. She has this question for you, "Plex has a significant amount of data about your user's viewing habits. How do you address the privacy issues associated with that data?"

Scott Olechowski (30:18):

So a couple of things. We have a very clear privacy policy with GDPR in the EU. We've got a huge project to harmonize our privacy policies and codify everything. Get everything right and be very clear and upfront about it, which we had always done. We were always very, very privacy-focused, but we also weren't collecting a lot of data, eight years ago or whatever. To do the things we want to do to help people, we need to collect data. Then we need to understand how the products are being used. So in our privacy policy, we make it very clear with your personal media, we have no idea what you are watching. We don't touch that. We know that you watch something. We know that you played something on your iPhone for an hour. We have no idea what you play, but with our streaming services, we know exactly what you play. It's almost impossible not to know it because we're just giving it to you. We're serving it to you. And we make that very clear as well.

Scott Olechowski (31:03):

And we actually really do use that data to figure out recommendations. We use that data to figure out where we should invest in content. We use that data to improve the experience and all those types of things, but it is data that could be sensitive, right? You don’t necessarily want us to know what you're indulging in to be spread around the world for everyone to know. We've built our entire metric system on top of Google BigQuery. It's in their systems. We've been using it for a while. They have a good track record on security and keeping stuff private. It's hosted in the EU to comply with the EU GDPR rules and all that stuff. So thanks to one of my product managers. We have a great GDPR compliance program. We have a great privacy policy. It's very clear. It explains everything.

Scott Olechowski (31:45):

All the products comply with that. We have internal processes around what metrics are allowed and what fields we're allowed to collect from where, and this and that and what's anonymous and what's not, and is truly anonymous. And we've had a lot of people review this and nothing can get added without going through a whole peer-review process here. So I feel like we're in a really good place with that and it's that balance of understanding what's sensitive and what's private and being clear about it with, "Hey, here's some stuff that's not, but here's the good we're going to do with it." And we're not selling this data. We're not doing anything like that, but it is data we do collect and we have to treat it very carefully.

Alison Dean (32:18):

Obviously, with the work that you're doing with data and with privacy and with security, how does that tie back into the work that you did at Cisco as it relates to global threat intelligence ops that you had a hand in? And I suppose since that was some time ago, what's the same between then and now?

Scott Olechowski (32:37):

Well, it was interesting when we came in. I was working at PostX helping lead that company in the product development and business development there. That was email encryption and secure mail. That got acquired into the company called IronPort, which was a very successful anti-spam, web security, email security company that then got acquired by Cisco into the security group. I had a couple of different use of it. one was working closely with the Chases of the world, understanding their enterprise needs across all of these different divisions and different use cases and security and photography and messaging and all that stuff all the way to the Cisco use case, which was like network security. But what we found is that the threat landscape was evolving so fast and we started nation-states participating in this at a scale that just didn't exist before because the internet didn't exist like this before.

Scott Olechowski (33:22):

They started to understand that what levers and knobs they could turn to do interesting things for themselves, right? Whether it was moving money, divert money, or mess politics. All these sorts of things. So what we found was we were building all this security stuff. We understood the individual threat, "Oh, this thing is attacking that." But we didn't understand the why. Why were people trying to do this? Why was that attack important? Why did that attack shift from this to that? What happened here? So we decided that this group needed to really try to get to the underbelly and understand why these things were happening. It was fascinating because these ecosystems, they really are economies of this dark web stuff where, "Hey, here's a group of people that can sell you access to machines that are rooted, that you can run your software on.

Scott Olechowski (34:05):

Okay. Now you can run your software on that machine to infect another machine and target these people based on, "Okay, these are the CFOs of the company, or these are the controllers that have access to my banking system." The other people would make the software that could then be installed on accountants or controllers machine that then knew how to attack a couple of dozen different commercial banking systems and literally wire money off and hide the tracks when they looked at the ledgers.

Scott Olechowski (34:29):

So we would get our hands on that software and try to understand how it worked. And then understood like who are the different various players and components of this economy? Who was selling access to rooted machines? Who was selling the software? Once you could get it there, who was profiting from this? Where did it go? And then we'd find all these other things like, how do they move the money to Ukraine from here when the money got wired and they literally have a website that you would go and you'd see this thing on a telephone pole.

Scott Olechowski (34:51):

“Hey, want to earn money from home? Make 20 bucks an hour.” People will go to the website and it's this whole beautiful-looking website. It looks like a financial services company. They had a message board where people are like, "Hey, can I contribute to my 401(k)?" And these people were basically mewling money through Western Union and making money doing it. It's just really fascinating. So to me, it helped us all understand, not just what the attack was, but why. So you can start to anticipate where the real risk was. Defending against security stuff is always a resource allocation issue. You can't defend against everything all the time. So you have to pick the most important targets and understand how they're being attacked and it changes every day.

Scott Olechowski (35:31):

I think what it taught me was, (A) you can never rest. Like there's no rest. We're all connected now. Two, it's going to evolve constantly. We solved this today. It's going to be different tomorrow and ultimately, if you can understand how something can be exploited, then you have a better chance of understanding how to protect it. In the case of our users' data, that's very valuable data. You could potentially harm someone's reputation based on this, or exploit something here, and if you understand that then you understand like, who would be interested in it and what data inside there they'd be interested in and all that stuff. So I think it's helped me at least realize where to think about the biggest risks, knowing that everything's at risk.

Scott Olechowski (36:09):

If it's connected, it's probably at risk at some level, and we can do a lot of things to protect it and to monitor it, and have better security around it. I mean, the one thing that drives new people at Plex crazy is we require all sorts of different things to get into your accounts, even just to use Plex. You want to use Plex at your home, you used to be able to sign in there. Nope. Now you need to opt-in with these other secondary things and this, and you're like, "Why do I have to do this?" sorry, it's part of the deal here. So even the user experience company has to sometimes draw a line somewhere.

Alison Dean (36:37):

I can't say that that gave me peace of mind about security, but yes.

Scott Olechowski (36:41):

You're welcome.

Alison Dean (36:42):

We're just all supposed to be like, "And what are you not doing that you should be?" Yes.

Scott Olechowski (36:46):

That'd be healthily skeptical.

Alison Dean (36:48):

Always, Always, always. Okay. So in our last few minutes together, I want to talk about leadership and some of the themes with leadership that you've experienced. How has your leadership style evolved through the years?

Scott Olechowski (37:03):

That's a good question too. You got them today, Alison. I started off as my own little independent contractor doing this software development that I talked about. And now I lead a good size team. And as an innovative attributor, I'd always do my best and do a little bit more and take on a little bit more and then I would get assigned to more responsibility, and eventually, that led to managing teams. But even along that way, I always still like to keep my hands dirty. Keep my hands in the soil and still doing certain things and I still do.

Scott Olechowski (37:28):

Til the day I die, I'll still be mucking with stuff, but I think probably my biggest transition as a manager, a leader, has been to really try to empower my teams. Ultimately, we're only as good as the teams that we have, and finding that mission that gets people excited and gets them to say, "Yeah, I'm going to put in a little extra and I really care and I want to think about security because I know if we get taken down here, that's not good."

Scott Olechowski (37:50):

That extra level of concern and interest and passion around it, and my job is to help get people excited, but then empower them to get their people excited and get their peers excited. I think in the past I used to do the traditional less mature manager thing and jumped in on things and like, "Oh no, I can do this better. Or, hey, you should do it like this, blah, blah, blah." I am trying to create more space and let these amazing people and these amazing teams do their jobs and help guide or give a different perspective on things here and there and build the relationship in a way that they know I have their best interests at heart. They know I'm going to do everything I can to get them unblocked and help make them successful and I'm not going to come in and just do it for them.

Scott Olechowski (38:28):

So I feel like that's probably the biggest transition I've made is to relax a little bit, give everyone a little bit more space to do their jobs. Then it's amazing how people step up. I mean, I think that's probably the most exciting part about it is you let go a little bit and then you get this proud papa moment where you're like, "Oh man, those guys really did something amazing and they did it without me getting in the way.

Alison Dean (38:47):

Right. 100%. What do you want the people that report into you to remember you for?

Scott Olechowski (38:51):

It's this work hard play hard ethic. one of the things that we decided early on with this company was we're going to do something really hard because we know we're going to have to work really, really hard. If we achieve this mission, it's going to be really, really great, but we also have to have some fun doing it. I try to bring a little bit of levity to things, but I push. I mean, they know I'm pushing, I'm pushing, but I think they like the fact that it's never so serious. This is not a life and death business by any stretch. I think they enjoy that I have that perspective while I'm also serious about getting things done and pushing hard. So I hope that's what I get remembered for not just being a pain in the ass.

Alison Dean (39:26):

And for putting on amazing company retreats, at least approving them to occur.

Scott Olechowski (39:34):

Getting the whole company together is really, really valuable when you're remote. And we have a little bit of that work hard, play hard. We do this thing. Have you ever heard of Malort?

Alison Dean (39:42):

I think I have actually.

Scott Olechowski (39:43):

It's awful. It's the worst thing ever and it's something that for the folks that do enjoy an alcoholic beverage, we'll ask them when they joined the company to do a shot. When we get together at one of our Plex cons, people are doing shots of it and it's awful. It's funny how sometimes the greatest bonding things are the most terrible things. Terrible projects bring people together. And Malort’s crazy twist of fate brings people together. So it's been a fun little way for me to share some of my Chicago heritage with the rest of the world.

Alison Dean (40:15):

It was a terribly tasting thing, but you'll remember it for your entire life and look back on it so fondly.

Scott Olechowski (40:21):

Exactly. People do. It's funny.

Alison Dean (40:23):

It makes perfect sense. Of course, everyone's bound together by this moment they've shared. It makes perfect sense. Okay. So lastly, if you could speak to a breakthrough that you've had recently, what that looked like?

Scott Olechowski (40:35):

I have one that I'll talk about. It's not super recent, but it's one that I like to share because to me it really has been a breakthrough and it wasn't our idea necessarily. I think other big companies have figured this out and we just stole it, but I'll share it just because I think it is super important. So we were struggling with getting the right resources together to accomplish big projects on time. We'd always say, "Well, man, that's going to take six months or that's going to take nine months." And then it would end up taking a year and a half. We were just not great at estimating and I think it's typical. You got people that are excited and they're talented and everyone's like, "Well, yeah, if everything goes perfectly, we could do that in six months." Because six months is an infinite amount of time when you're developing something, right?

Scott Olechowski (41:14):

Literally, six months would be a year. You'd double it at least every time. Sometimes worse, sometimes we'd get closer. So we moved to this model where all of the work we do now, we plan in six weeks cycles. So we don't plan anything further out than six weeks. We know we're not going to finish everything in six weeks. We know the next chunk is going to happen there but we set goals and objectives. We do two things. We organized teams around objectives. So we make sure we have the right resources. We've got backend work. We've got central services work. We've got metrics work. We've got ad work. We've got client work. We've got to server work. All these different teams that work on different things and sometimes a project doesn't require three of those groups. Sometimes it requires all those groups. Sometimes it requires just one and it's always different.

Scott Olechowski (41:51):

And then on those teams, there's different capabilities and specialties and whatever. So what we'll do is we'll set the objectives for the six weeks and build the team around the objectives. Making sure they have the resources that they need to achieve what those objectives are in that timeframe. And it solves the resourcing problem and it solves the, "Oh, I have six months. I can do anything," problem. Six weeks is a tangible amount of time. We're like, "It's not even two months. It's like a month and a half, this is going to be here before I know it and I have to deliver on this. I have to commit to doing it and I have the resources to get it done." It allows you to adjust every six weeks. We have a break in between. So you get to adjust a little bit based on what you did or didn't do, what the markets doing, what other factors, what are new opportunities arise or challenges have come up.

Scott Olechowski (42:34):

It's really improved our focus. It's improved our execution. It's improved our results because of that. So to me, that was a bit of a breakthrough because we've tried everything in my career, all sorts of different stuff. And this one has stuck and I think the teams like it too, right. And then sometimes the teams change and that's fun too. You get a little variety. That's the one that I’ve been kind of sharing lately because we've had enough time to know that it really has improved things. We have the data to back that up.

Alison Dean (42:57):

And I think it's interesting with six weeks, it's like you said, it's just enough time to really get stuff done, but it also is the right amount of time where if you do have to make any pivots after that six weeks, you don't feel shocked and disappointed and in pain and crushed because suddenly it's like, no.

Scott Olechowski (43:16):

You're exactly right.

Alison Dean (43:17):

I like that. I like six weeks. I like it.

Scott Olechowski (43:19):

For us, it's been the right number. I mean, and maybe there's a different thing, but seven seems like a long time. Seven weeks? I can do anything in seven weeks.

Alison Dean (43:24):

It's psychological.

Scott Olechowski (43:25):

Yeah, psychologically. This kind of human timeframe, scale thing. And six weeks is not that much time to do anything, but it's also enough time to do meaningful things. And you like said, adjust.

Alison Dean (43:34):

Right. So on that note, thank you for tuning into The Breakthrough. Thank you to Scott.

Scott Olechowski (43:40):

Thanks so much, Alison. Thanks for having me.

Alison Dean (43:42):

Thank you. Thank you, Scott and we'll see you all next time.

Alison Dean (43:45):

Thank you for tuning into The Breakthrough brought to you by TheoremOne. Make sure to hit that subscribe button and leave us a comment. You can find us wherever you listen to podcasts and for more great content, follow us on Twitter and Instagram @breakthrupod. That's breakthrupod. I'm your host Alison Dean, until next week.

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