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He had a dream to make it in Hollywood, but a career shift away from MTV paid off – big time! Jascha Kaykas-Wolff is now president of Lytics and has previous leadership experience at Mozilla, Yahoo, Webtrends and Microsoft. When Facebook messed up on data security, he was the one of first tech execs to pull ads from the platform. So how can you punch above your weight, move up as a marketer and LIVE your rebel brand? Jascha says some basic structure can change your world.

The Rebel Instinct Podcast episode 7: Jascha Kaykas-Wolff

He had a dream to make it in Hollywood, but a career shift away from MTV paid off – big time! Jascha Kaykas-Wolff is now president of Lytics and has previous leadership experience at Mozilla, Yahoo, Webtrends and Microsoft.
Article Outline
He had a dream to make it in Hollywood, but a career shift away from MTV paid off – big time! Jascha Kaykas-Wolff is now president of Lytics and has previous leadership experience at Mozilla, Yahoo, Webtrends and Microsoft.

On every episode of the Rebel Instinct, our team sits down with rebels from across the marketing landscape to share stories about bold moves they’ve taken as marketers. Subscribe for more.

Galen Ettlin:
Hey everybody. Galen Ettlin here with Act-On Software. Casey Munck is my VP of marketing back again after a trip to London. Welcome back, Casey. Good to have you here.

Casey Munck:
Thank you. It was jolly good time

Galen Ettlin:
Picking up the lingo too. Now our YouTube viewers can also see our guest here today is a MarTech mover and shaker Jascha Kaykas-Wolff. He’s president of Lytics with previous executive experience at Mozilla, BitTorrent, Webtrends, Microsoft, and much, much more. Jascha is also behind the podcast called This Is Your Life in Silicon Valley and is a published author. I’m not worthy Jascha. Thank you for being here.

Jascha Kaykas-Wolff:
You’re just making me sound old, but thank you. I appreciate it.

Casey Munck:
You’ve got skills. You’ve got skills. Well, welcome to our conversation. Stoked to chat with you. So you really push for creativity in the tech and the science space. Why is that important to you?

Jascha Kaykas-Wolff:
I mean, Casey, I’ve been doing this for a long time and I’ve kind of been trying to work on two things throughout my career. One has been about finding the right technology to build an infrastructure that can help a team create process. And process has always been important to me because I think process creates a foundation where you can start to introduce creativity into an organization and creativity is really the point where you can introduce messaging that can resonate with an audience that you care about. And I think the real connection point in any business is the moment where you can find repeatability and creative messaging that attaches to the audience that cares about what you build as an organization. I think that’s kind of an art and a science mix that gets lost in a lot of businesses where you forget that there’s some humanity and the things that you’re trying to build and actually some humanity and the thing that’s trying to resonate for the person that you’re trying to solve a problem for that we’ve been taught I think over and over again throughout the course of the last 15 to 20 years, that experimentation and testing is the thing that drives performance above all else.

But the reality is that there’s humanity and absolutely everything. We care about the relationships that we have, we care about the things that we’re trying to solve problems for, and if you forget that and you don’t design that into the processes that you’re trying to build in helping your organization be successful, you’re probably going to optimize yourself right off the side of a cliff. And I think you kind of have to start from that from the very beginning. Recognize that creativity is fundamentally that the kind of source input for success in any business.

Casey Munck:
Absolutely. That’s been our theme actually this year is make marketing fun again because kind of gone down the rabbit hole I think of over analyzing numbers to the point where it’s like marketing’s supposed to be a creative field, but it’s interesting that you were talking about process is sort of the foundation that can empower creativity. That’s something I really believe in too. I’d love to know a little bit more about that.

Jascha Kaykas-Wolff:
Yeah, it comes back all the way to going through school, at least for me. I’ve never really considered myself to be a wildly creative person, but what I always appreciated about school as a very young person is that the boundaries that were introduced to me helped create an environment where I had an opportunity to be creative and do it with some expectations both on time and some expectations on what the limitations were they had to work within. And the output with those kind of boundaries always resulted in something that I had an opportunity to be proud of. And so the idea that constraints bred a space where something that you could be proud of was a probability for me bore this theory that as I started to become, at least as I started to have an opportunity professionally to create processes with teams, those constraints really created the form field for teams to be more creative. You just have to have some expectations around what the output’s going to be.

Casey Munck:
It pushes you to be creative with those boundaries. I love it.

Jascha Kaykas-Wolff:
Yeah, I mean I think the greenfield opportunity is a bit of a misnomer. Professionally, you don’t really get the greenfield, you don’t really, I think even founders to an extent forget about the marketer, but the founders don’t really get the opportunity just to dream up what a problem is they’re going to try and solve for. They have some sort of constraints they have to work with and it’s either the amount of time that they have to solve a problem for the amount of funding that they have to work with, the kind of persons that they’re going to work with, they’re going to be able to help them solve the problem with, we all have constraints that we’re working with and you kind of narrow down the constraints that you have to work within depending upon the type of problems that you’re trying to solve for. And in the case of marketing, in many cases, the constraints that you have to work within are really intending to be built around trying to solve something that is intending to have a creative output. So it really is fundamentally just about creating constraints so that you can have a creative solution for it. Right. You just have to wrap around the ability to be able to tell the story around the measurements of its impact in the business.

Galen Ettlin:
You mentioned earlier work that you’re proud of through this process that you’re talking about. What sort of creative work have you done that you looked back early fondly for?

Jascha Kaykas-Wolff:
I probably will be forever most proud of happened when I spent time at Mozilla. I was spending time in Berlin quite a bit. Our European operations were based out of Berlin at the time, and I happened to be with a group of people and we were spending time at different contemporary museums around the Berlin area and I came across an exhibition, it kind of looked like almost a trailer inside of this museum. And as you walked into the trailer, this thing that looked a bit like a trailer, people that were inside of it were a bit dressed like the geniuses that were at Apple stores. And when you walked in, they would start to talk to you, but they would introduce themselves as ingeniouses. And that whole idea inside of this experience is that when they talked to you, they would start to ask you questions about what you were doing with your phones in particular, and if you understood what was happening with the data that you were sharing with whoever the manufacturer of your phone was, and they would teach you how to change the settings on your phone so that you could have better control of the way that you were sharing your data.
The exhibition itself was ultimately about how you take better control of the data that you have access to or you have the ability to share. And Mozilla, we cared quite a bit about helping people understand how to take better control over your online life overall. I was so kind of intrigued by this one particular exhibition in this one particular museum that I went and found who the particular artists were that worked on it. It happened to be a group called the Tactical Technical Collective that was based out of Berlin. It was a group of artists and ended up working with them and a group of other artists that they worked with to create a pop-up art exhibition that we ended up calling the Glass Room. And we brought in about 40 different artists, brought it to four different cities around the world to London, New York, Los Angeles, San Francisco, and a couple other cities.

Created an experience where we brought in, I think in the neighborhood of around a hundred thousand individuals in all of those different cities and helped them experience different ways that businesses were interacting with them on the internet in particular, using different artists exhibitions to help teach them ways that they probably wouldn’t believe that businesses were interacting with them and taking information from them without their knowledge. For us as a business ended up driving pretty massive awareness of the brand of Mozilla in addition to changing thousands of people or hundreds of thousands of people’s perception about a way that they could manage their online lives in particular. So both impactful but also wildly creative. And it wasn’t just me, obviously, it was a very large group of people that were responsible for being able to pull it off and a wildly creative group of artists that were able to do it. But I think back amongst the 20 or over the 20 plus years of my creative life really have never had an opportunity to do anything even remotely close to that from a creative perspective and immensely proud of that work in particular. So classroom, you can still probably do a little bit of search for the classroom in San Francisco or New York and see a lot of the press junkets from it. It was a very, very cool event.

Casey Munck:
That sounds really interesting. I’ve always had a lot of respect for that brand, how they take care of their users. So Mozilla, I mean it seems like it would be a pretty rebellious brand to work inside, but your concept is pretty unorthodox. Did it take some convincing with leadership to get that across the finish line? And if so, how did you do it effectively?

Jascha Kaykas-Wolff:
The expectation of a robo brand when you have great alignment around the management team is that the work that you do, especially on the marketing side, has to be rebellious first and foremost because you really have to find ways to punch above your weight class. And the way that you do that is to create interest that has an attachment to public culture and to the zeitgeist. When you do that as a rebel brand, you have to have an expectation that you’re going to ruffle some feathers. And as a management team, when we had agreement that we were going to operate as a rebel brand, it actually becomes quite easy to get alignment around doing work like that. You may remember a point in time where Facebook became quite embroiled in a data breach. I ended up being the first CMO to pull all of our advertising off of Facebook.

We were able to do work like that to speak about it publicly, to use that as a platform to be able to get onto national news and to kind of morning talk shows. That kind of work becomes very necessary to do in order to be able to get the kind of recognition that’s necessary as a rebel brand. So when you are a rebel brand, when you try and operate as a brand, in order to be able to get buy-in to do work like that, I think you have to do the pre-work front to get the acknowledgement as an executive team, as a management team that that’s the expectation of the kind of work that you’re doing. So the pre-work is necessary.

Casey Munck:
Oh my gosh, this is such great advice for me personally, honestly, trying to run a rebel brand over here. And so that’s great. I mean, so it sounds like the leaders at a company like Mozilla, they all get it right, but were there ever people like the finance guys or maybe the guys in engineering were like, why are we wasting our money on doing this crazy wacky thing over here that you had to get them on board? Or was it across the board rebels even in places like that?

Jascha Kaykas-Wolff:
I think, I mean your obligation, my obligation when I was in marketing, any of us that are in marketing is first and foremost to be a great business leader. I think that’s one of the first, and I think most important pieces of advice that I will give to anybody that I mentor that is a marketer. And then the second responsibility that we have is to be a functional expert in marketing. And when you operate that way as a leader, the discussion around is my CFO going to give me a hard time around what I’m spending my dollars on? Isn’t a discussion that we need to be having because when you or I come to the table, if we’re sitting in a leadership position that’s responsible for marketing, we’re not going to be coming to the table with Flouncy ideas about where we’re going to be putting our investments.

We’re going to understand the dynamics of our business, we’re going to understand the importance of where we’re making our investments in our portfolio of investments, not just in marketing. We have to as marketers understand how our business works first. And when we do that, Casey, we don’t, you and I, if we’re sitting in marketing leadership positions or anybody else that’s listening to this discussion, we don’t have those discussions around, I’m making this investment in this campaign. Let me try and discuss with you why this is a valid investment to make. We already understand the way that the business works, and we have already discussed the portfolio investments that we’re making, and it’s an afterthought of the campaigns that we’re running. And I think that gets lost because it’s very easy, it gets lost. So often we want to believe that our division that we are functionally responsible for running is the most important thing in the business.

I have to make sure that my team is performant, and if my team is not performant, I’m going to lose my job. But the reality is that we have to make sure that the business works well and marketing is one piece of that business. And if we don’t think that way, kind of doesn’t matter what we do in marketing. So I think it’s just a reorientation of the way that you have to think as a marketing leader that makes all of those discussions about getting alignment to marketing or with marketing to the rest of the business and campaigns in particular, it just changes the way that those discussions

Casey Munck:
Take conversation. Yeah, that’s really good advice. Know your stuff beyond your wheelhouse. Know what is going on all the way across the board.

Jascha Kaykas-Wolff:
I can tell you that my experience, I’ve now been helping run an organization as a president. I have day-to-day operational responsibility. I partner with our co-founder to run lytics, and I don’t have day-to-day responsibilities of any functional area. I can say now that I see how marketing can run as a functional department outside of marketing being responsible for it, and I want for our marketing organizations inside of Lytics to operate this way, I want our, and I coach our marketing leaders to think about understanding how the business works overall. I want them to understand the investment theories in our marketing teams compared to our channel teams, compared to our commercial teams, compared to our engineering teams, compared to our product teams. When our marketing leaders understand the theories of impact for all of the different departments across the organization, it makes it super rational to have discussions around what’s the portfolio investments that marketing is making and how do those relate to the rest of the business? It just makes the conversation super rational whenever we’re talking about any investments we’re making. And that’s the best kind of discussion to have when you’re a marketing leader. It makes all the conversation about whatever kind of rebellious campaigns you’re intending to run, it’s almost moot. It’s like, of course we’re aligned on our brand. Of course that’s what you’re going to do.

Galen Ettlin:
Alright, so Yasha, as a former TV news anchor myself, this jumped out to me at the bottom of your LinkedIn page. I was creeping way down there. You have some previous production experience at MTV, so we want to know what that was like. Who’d you meet? How did that experience speak to you? How’d you move from media to tech? Whatever you want to share.

Jascha Kaykas-Wolff:
Galen, you read the news. Did you like that?

Galen Ettlin:
Oh yeah. It was a dream job. It just was very hectic and crazy. So we made the shift.

Jascha Kaykas-Wolff:
Well, let me tell you, my kind of dream as a young person growing up in Oregon was to move to Los Angeles and work in film and television. I moved to Los Angeles, I went to school there and I found my way into film and television. I ended up working for a group in MTV called Bunim and Murray. Bunim and Murray is probably best known for, we’ll call it inventing reality televisions. This is in the late nineties. I worked principally on a show called Real World and had a secondary show called Road Rules and a third show that I worked on the set of called Singled Out, so I’m aging myself obviously, but Singled Out was a dating show. There were 50 guys or 50 girls on one side and then one person of the opposite gender that that group of people had the opportunity to date.

You’d ask a bunch of questions, they would whittle the group down to three people, and then you’d ask a round of questions and the last person that was standing who would win the date Real World, they would put a group of people into a house and then they would film them over the course of several months and then come up with a show and then road rules. They would put a bunch of people in an RV and send ’em across the country with basically a scavenger hunt. So I worked as a PA on all those shows and I had different jobs in each of the shows as a pa. So I would review people’s submissions to be on road rules in real world. I would be on set on singled out, and I would help people get ready to go on the show. I would ask people questions about what questions they might get when they would go on the show, and then I would say, oh, Casey, what would you answer for this question?

And Casey would give me the answer. I’d be like, that’s a pretty good answer Casey, but Galen, what would you answer? I’d be like, Galen, that was a great answer. So Casey, if you could ask this question, answer it the way that Galen did. So kind of help people prep on reality tv, so they give the best answers. I worked there for a couple of seasons and what was really interesting for me is that although this was what I believed I wanted my career to work in this space, I became very disenfranchised very quickly, and that mostly happened because I worked really hard and I thought I was trying to do everything in the way that I should be doing it, working hard, trying to be smart about the way that I worked. And I found myself in a scenario where most of the jobs that I was up for moving up to production coordinators, et cetera, ended up being given to other people.

And mostly, at least in my perspective, and maybe I’m rethinking what happened 25 plus years ago, they ended up being given to people who were the sons and the nephews and the daughters of some of the more senior people in the shows, the producers of the shows. And so it was pretty disenfranchised that it felt like it was a very nepotism driven industry. And so I ended up leaving and I found my way up into the Bay area mostly because I had friends that were in that area and I was couch surfing literally at the time and read an article in the San Jose Mercury News about a company who was built around this concept of meritocracy, where if you were smart and you worked hard, you had an opportunity to grow professionally. And it was built around the importance of the internet and the ability to find information across the internet.

And it was a company called Yahoo. And I literally wrote my diatribe who I was and what was important to me and I really didn’t know what I was going to do. And I sent this email in and I got a call a couple of days later and I went in for an interview and I got hired at Yahoo in the beginning of 98 and got a job in sales operations and rose in the ranks there very quickly. I like to believe that it was because I was smart. I think that I worked hard and a lot of it was timing and that I was lucky and I ended up finding some really amazing mentors that helped me find different and new opportunities. But a lot of it was about this kind of difference in other industries and technology. And I, again, a lot of other industries, there’s just a way that things happen.

And in technology, I do truly believe that there are opportunities that show up that don’t show up in other industries. If you work hard and you work smart and you find those lucky chances where you meet great people who can be great mentors, a lot of things can happen that really work in your favor. I owe a lot of my career to great mentors and lots of great opportunities that those mentors have given to me or at least put me in front of that I’ve been able to take advantage of. So my career path is a lot about that, about taking advantage of opportunities and being fortunate to be in those opportunities.

Galen Ettlin:
And talk about timing too with one, the rise of reality tv real world is the og and then on top of that, making the shift to Yahoo in 98, right as the internet is going to take the world by storm. So

Jascha Kaykas-Wolff:
Timing’s everything. Yeah.

Galen Ettlin:
So how are you a rebel in your non-work life?

Jascha Kaykas-Wolff:
We live up in the Sonoma area, which is north of San Francisco by about 45 minutes or so. I’ve got three kids, they’re older, one’s off in college and one’s about to go into college and one’s about to go into high school. My wife and I moved our family up here in large part because our daughters rode horses and my wife grew up with horses and she decided to start riding horses again. And about four years ago she introduced me to horses. So maybe we’ll kind of borderline that. I would call this a bit of a rep attitude, but I’ve been excited kind of in my forties now exploring a new activity that I feel like makes me maybe feel a little bit more rebellious in my older age. We recently started playing polo together, which I find to be a pretty interesting sport to play in that is a bit unconventional. So as you think about getting a little bit older and finding ways to bring some excitement back into your life, getting on a horse and riding and 25, 30 miles an hour and playing a full contact sport against another four people is a pretty interesting way to spend your weekend

Galen Ettlin:
And challenging. That’s a hard sport.

Jascha Kaykas-Wolff:
It’s a pretty interesting one.

Casey Munck:
Well now it’s time for our ‘honey, I don’t think so’ segment talking about what’s annoying you in marketing or MarTech that needs to stop now. You’ve got 60 seconds to plead your case. Galen will be counting you down. So are you ready for your ‘honey, I don’t think so’?

Jascha Kaykas-Wolff:
I’m ready. Well, this one’s pretty simple and I think it’s going to take a lot less than 60 seconds. I think this is kind of in marketing and MarTech and more generally. There is I think a very systemic problem that we have in marketing and that’s that there are a lot of very wealthy VCs and billionaires that tell us what to do. I like to call it a little bit paraphrase as billionaire adoration, there are a lot of non operators, a lot of billionaires and VCs that believe that they know what marketing is that believe that they know what tools we should be using. And I think we take that for gospel as marketers. There is nothing that’s more important than practical operational experience. You’re thinking about as a marketing leader, you’re thinking about as a marketing practitioner what the best path is to be successful. There is nothing better than actually trying and experimenting yourself.

Casey Munck:
You did it. You did it. Way to go. I am all into that. So thank you so much for your time today. We really appreciate the conversation. I have learned a lot personally, and I know it’s a lot of great information for the marketers out there being rebellious doing their thing. So thank you so much for your time and have a great rest of your day.

Jascha Kaykas-Wolff:
Nice to spend time with you both.

Galen Ettlin:
Thanks everyone for listening to the Rebel Instinct Podcast. Be sure to follow act on software for updates in upcoming episodes and remember to always act on your rebel instinct. Until next time.

Check out the next episode of the Rebel Instinct Podcast with Ben Kiker, career coach and former CMO who overcame personal struggles to succeed and help others.

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