Building Brands That Move - Jason John

0:00Hey, welcome to the CMO Whisper Show. I'm your host, Steve Olensky. Part marketing practitioner, part ad agency veteran, part journalist. I was a writer for Forbes for 10 years. I've had so many insightful conversations over the years with business leaders, to athletes, to celebrities, to, of course, CMOs. The only difference now is instead of sharing those insights through written form, I'm doing it this way. My guest this week is Jason John, a seasoned marketing leader and entrepreneur who spent his career at the crossroads of culture and digital innovation. Jason has worn a CMO hat at 1-800-Flowers and Publishers Clearinghouse and held senior marketing roles at some of the most iconic names in retail, including J.Crew and Martha Stewart, where he drove large-scale digital transformation and customer growth.

0:53He was also at Guilt Group during the heyday of flash sales, helping fuel triple-digit growth in one of the first scaled e-commerce apps. And because that wasn't enough, Jason recently launched True North Group, a venture that brings together brands, athletes, and communities through premium live experiences and cause-driven partnerships. Known for blending data, creativity, and cultural insight, Jason is passionate about harnessing AI, performance marketing, and purpose-driven storytelling to build movements, not just campaigns. Jason, my brother, welcome to the show. Awesome. That was amazing, Steve.

1:28Thank you. You are very welcome. I have a burgeoning career to just record intros for people. You're doing a great job at it. You know, just when you go on stage, plug, play the Steve-O intro. OK, so I got to start. And this is this is this is not just the professional side, but the personal side about what was it like literally with Martha Stewart and Mickey Drexler and J. Crew and take us into those those those rooms. Yeah, definitely. The early days and, you know, from a young kid from upstate New York, a small town, having his first job in New York City, be with none other than Martha Stewart.

2:06You know, it was pretty crazy. It's probably more crazy now that I reflect on it than at the time. And Martha Stewart's Omni Media, you know, that was in, you know, very high growth mode when I first joined. So just coming off the IPO and launching a lot of different businesses from the book club to obviously the magazines to Martha's Flowers, getting into all different verticals. Kmart was a very big partnership for them and had a really big deal. And she was everywhere in the Kmart stores. So it was an exciting time to be there. I have some definitely some interesting stories to go along with that.

2:46Some I can share, some I can't on the air. You know, I remember one time, you know, very early on, it was in our New York, one of our New York City offices. I was running late and I was trying to catch an elevator and I ran up to it and I just stuck my hand in there and the elevator closed on my arm. and I might have said something explicit at that point. And the elevator door opened up and of course Martha was standing in there but she was so nice. She just smiled and said, believe me, I've been there. So she was much kinder than people made her out to be, obviously for made for TV movies. It was always great to create more of a villain character but she was really intelligent, very driven and awesome to work with for sure.

3:25How about Mickey at J.Crew? What was that like? Yeah, definitely. Yeah, so Mickey was another very very driven uh visionary obviously very passionate in in the merchandise space i had the fortunate time to work with them and j crew because you know when he joined j crew it was it was not doing very well it was more of a catalog company at the time yes they had retail stores but it was really a mid-tier direct mail based brand um so mickey really got in there maybe a couple months before I joined the organization. I remember the interview with Mickey too. Mickey was sitting at this really long table when I interviewed.

4:03And again, I'm still relatively young and new in my career, so very intimidated to be in that atmosphere and even speaking to Mickey after obviously the fame and success that he had in the 80s with Gap and Gap Group. So I remember he asked me maybe two questions. The second question was, what do you like about what we're doing so far? And at the time i was uh engaged and i really liked that they were launching these bridesmaid dresses um that were affordable and you could wear multiple times because the friends we were at i would hear the complaints all the time oh we spent all this money on a dress and we were never able to wear it again uh so i said mickey i love that concept of making it affordable and and where any and he slammed his hand on the table goes i love that that's great i love the way you think you're hired literally hired me right there.

4:49I was done. That was the end of the interview. And I was now working at J.Crew. But that's, you know what that's like? And I don't mean to interrupt you because I want to hear more, but that is right out of the Bible and playbook of the classic book, Good to Great. Yeah, exactly. Right. The right leader, when you meet someone and it's just, nope, you're not leaving. I'm not losing you. Yeah, exactly. It was great. And, you know, he taught me a lot of things as well. I had, And when I first joined, I was in this cubicle, and I was the first cubicle right outside of where Mickey sat. And again, Mickey didn't sit in an office.

5:22It was a big open area. So it was fortunate and unfortunate that I was the first one there, and I just could hear every conversation that was going on. And obviously, he was very passionate when he spoke. And I did get to pick up, even though I had work to do, I had to block it out sometimes. You know, we didn't have big like my daughters now have these giant, you know, headphones that you can't communicate with them if you try. You know, at the time, you just had to rough it and kind of block it out on your own. And, you know, he taught a lot, taught me a lot about organizations and keeping them more flat.

5:56And basically, you know, if you if you want to have more of a say in what the output is and the end product to the consumer, you can't have 15 layers in your organization before your ideas and concepts get there. So he was very passionate, you know, about keeping that hierarchy at a minimum. And I think that stuck with me from a leadership trait. But, you know, he was very open and transparent. He would go to stores, you know, patch in live. So we had this live intercom. And again, back in the day, we're here in the office five days a week. You know, we had this intercom throughout the office, which at that point was a great thing because he would be at a store.

6:30He'd be talking to a store manager, just asking, hey, what are the customers saying about, you know, what they're seeing in the store today or our new fall offerings? And, you know, the store manager would jump on and just say, here's what here's the feedback we're getting. Just so we're all in touch with the product, all in touch with what the consumer is thinking and saying in real time. You know, we didn't have to launch research projects for four months to figure it out. Like Mickey was going from store to store, patching in store managers so we could all hear what was going on. I just thought that level of transparency and sort of passion about the product was something that really stuck with me.

7:02Wow. So that was great. Now, on the flip side, the bad side was, you know, when he needed to talk to you about something, he would yell at you through the intercom to come down to the office. So you felt like you were 10 years old and the principal was calling again. But, you know, pros and cons with everything. But it was really a great experience. I can commiserate, my friend. And it's part of the, you know, coming up the ranks, if you will. So you went through highs and lows, man, right? You're with the Martha Stewart, but then that downturn, right? Yeah, you guys, yeah, you might have seen some Netflix specials on that.

7:31Yeah, I was there during that time period. And it was crazy because I said, you know, the company itself was really fun to work at at the time because they were doing so many cool things. You know, launching even the everyday magazine, you know, trying to get a little bit more in touch with an everyday need of the consumer for recipes and things of that nature to launching new businesses like Martha's Flowers. So when that issue happened, you know, the company definitely took a turn. and again that was a really good life lesson like there's nothing guaranteed in life um and you know a lot of things external to the business can impact the business so whether you're investing in businesses or uh you're working at a company that was a very harsh lesson to learn as a as a young person um you know to see that the business go from great to to in trouble um and obviously that was resurrected and all's well, you know, that ends well.

8:29But, you know, at the time it was a really rough situation. There was a lot of people very upset. We had to unfortunately cut a lot of positions and, you know, the company went into a different direction, you know, for the next year or so. But it was good for me from a live and learn and, you know, always understand that there's external factors that could impact a business and deal with that. And then the polar opposite was J.Crew's IPO. Yeah, that was the polar opposite. That was the high. So that was great. That was two and a half years of a lot of work, you know, building the data. When I first joined, you know, it was that classic, you know, did we start an email program?

9:06Yeah, we started it. And, you know, so-and-so has it on their computer. They have a file, I think. You have a file on someone's computer. Okay, not a good place to be. So how do we get this together? You know, they had databases, you know, in a lot of different places. The store database didn't talk to the catalog database. So, you know, getting that fundamental data story, you know, sounds easy and it's easy to talk about in hindsight, but it's a lot of work to build all of that. especially tying in the POS systems with a new online channel with an older school direct mail, mainframe AS400 type of backend.

9:49So it was an interesting time to build that. Launched really the websites, launched J.Crew Factory, had this little unknown brand that Mickey had bought for a few bucks called Madewell. And again, it was just a brand that he owned at the time. He A lot of the conversations in those days, I remember vividly is just talking about what Madewell could be and just coming up with that vision. So it was an amazing adventure around, you know, just those fundamental building blocks of data and how important it is to grow a business and a brand to, hey, what's the vision of the brand and the storytelling?

10:25How does that all come together? How does J.Crew go from a mid-level catalog brand to a luxury retail brand? and just building all the backend systems that drive that as well as all the storytelling that sits on top of it. So sort of bottoms up, top down, and to your point culminated in the IPO, which was a very good feeling to be a part of. Yeah, so it was great. It was a great two and a half, three years. And then you were also part of Guild Group, right? So for those not familiar, in the late, I guess, 2000s, 2010s, it really was a cultural movement. And that's not hyperbole, right? I know you may not be able to be, can say it objectively because you were in the middle.

11:01So I can say it from the outside looking in. And before we get into, you know, what made it such a phenomenon and what lessons you learned, for those not familiar with Guilt Group, how do you describe what it was? Yeah, so it was in the flash sale heyday. So when flash sales became popular, and unlike my parents who thought that meant we sold cameras, you know, flash sales were sales that lasted for a very minimum time with a low amount of inventory. So you had to get on when it started. So at Gil Group, it started at noon, Easter, and we had luxury items. And those luxury items were heavily discounted, which you don't get to see very often, especially in sort of a luxury environment.

11:41So they were heavily discounted luxury goods that went on sale at 12 noon. And there was a very limited quantity. So you either you were able to get in and buy it and get out or you didn't. And consumers felt like that. So so any post order surveys that we have, consumers felt like they won. So it was one of the first real gamifications of e-commerce, you know, probably since eBay. I think eBay was probably, you know, one of the first to gamify sort of that bidding and winning shopping experience. But guilt really took it to another level with sort of the flash sale concept. And that's really what you had suggested tied into from a cultural perspective.

12:17It was great. Making luxury accessible and then also gamifying it to make people feel like they won something. amazing what what are some lessons that marketers even can apply today from from that yeah i think you know maybe yeah yeah definitely you know something we can probably you know speak to even with the rise of ai uh you know as well as just you know i hear a lot about storytelling you know people people overuse that word you know especially in this past couple years i hear it all the time about storytelling and brand storytelling well the story doesn't mean anything if it doesn't resonate in the culture.

12:51Right. And I think, I think guilt really taught me that if, if, if you can become part of the culture and what's happening or a cultural movement that's happening, that story resonates really well. You know, you can think about the worst movie you've ever seen that had a story. It just didn't resonate. You just did not like it. So it's not about, just about storytelling. I mean, storytelling, again, not to, not to mean it or to belittle it too much but um without cultural resonance the story doesn't mean much so so that's kind of what i learned at guilt um and then you know kevin ryan is is uh you know i'd be remiss not to mention kevin kevin is is uh iconic as far as bringing silicon alley to new york and a ton of startups uh you know business insider and and you know zola and so many uh that are attached to kevin to me kevin ryan is almost like kevin bacon like you can almost find all of these uh Great D2C internet companies and content internet companies that get back to Kevin at some point, either worked with Kevin or for Kevin.

13:50So he's an amazing entrepreneur. And he really brought forward a concept that I think is used more today is really the fail fast concept. He wanted to get things out there. A lot of different ideas, a lot of different concepts. At Gilt, we had Jet Setter and Gilt City. So we had several other brands under Gilt. And it was just push things out there. if it's not resonating, move on. Don't spend your time two years trying to figure something out. If you're not getting some immediate momentum, it doesn't have to be the perfect thing, but just enough to give you some concept pretty quickly that this thing has some potential.

14:25Sure, there might be a lot of nuances, tweaks, changes you need to make to make it really successful, but if you're not seeing anything from an immediate momentum standpoint, then just kill it and move on. So I think that was probably the biggest lesson. Because Kevin is a serial entrepreneur. Like he just didn't, you know, didn't have time to struggle for years to make something work. Right. So so he brought that down into the company and to me as a leader within the organization, being able to translate that for my team and just learn that was was a great life lesson for me. Publishers Clearinghouse.

14:57What what drew you there? Yeah. I mean, obviously a lot sexier than guilt, you know, and it was, you know, it's an iconic brand. And, you know, some of these brands that, you know, I went from guilt group that didn't exist. Right. The brand didn't really exist when I joined. It was it was around, but nobody knew about it. So it was really brand building. J.Crew was more of a turnaround story. But Publishers Clearinghouse, again, it's one of those brands that's been around since the 60s. And but nobody really knows under the covers what it is. It's like an enigma. It's like, OK, well, I know they they gave away big checks.

15:32Right. That's all I heard, too. They still give away big checks. It's like, yeah, certainly do. But, you know, ultimately in Publishers Clearinghouse, you know, sweepstakes is a lead generation tool. So you start to get millions and millions of people giving their first party data and signing up, you know, to win those sweepstakes. So unlike the Powerball, which just happened, what, a couple of weeks ago with the, you know, billion dollars and people are spending two bucks a ticket, you can register for free and sign up for the sweepstakes for free. So the quid pro quo on that was, hey, you give us some information.

16:06And, you know, based on that, we're going to try and sell you some stuff and we'll try and show you some other things. And then, you know, you get your sweepstakes entry for free. So they're sitting on a huge amount of household data in the U.S. And I just thought that was an amazing opportunity to figure out how to evolve that brand into the modern world and the digital era. So transforming that from a direct mail sweepstakes company into a media and entertainment company. And what do I mean by that? So we purchased, you know, we bought a couple of game companies, launched, you know, much greater attention, PCH games, launched many apps out there.

16:46Games like Spider, Spider Solitaire or Minute Mahjong, you know, those games, maybe an older customer will be playing and maybe playing from like my dad from 4.30 to 5.30 in the morning because no other human being is up that early for no apparent reason. So as he's playing that, you know, then we have our media side of the business, which is now showing advertising, targeted advertising, or our personalized algorithm that's showing merchandise. So there's a commerce component, too, where, you know, we can show personalized items, bullet blenders, that sort of thing, you know, at a discount and saying, hey, if you're interested in this, but again, all personalized recommendations.

17:22So under the covers, there's a lot of complex data personalization capabilities, layering on gaming, layering media on top of that. And it was really good for me to stretch my skills. When I talk to younger marketers, I kind of talk about checking boxes as they go in their career. And these boxes could be, you know, did you do performance marketing? Did you do brand marketing? You know, for me, it was also industry. It was also, you know, did you work in gaming? and guilt had a look gamification as i mentioned before but pch was launching a game you know more in the game division i worked in media but only as a buyer i didn't really work on the on the platform side so that gave me an opportunity to kind of look under the covers and see how this media business works behind the scenes right and not just as a buyer but as a seller so you know for me it starts to round out uh you know who i am professionally and take on things that i didn't know before which is always uh you know the more boxes you check across this giant matrix of things you could be learning and doing, you know, the better equipped you are in the future.

18:24So it was really helpful for me, a publisher. Got it. All right, let's get into True North. Yes. First question is, what inspired that? I think there was a couple of things. One was, you know, with the rise of AI, you know, it kind of went back a little bit post-pandemic where the need for people to have human interaction, you know, really, really swung on the pendulum, right? So after being, you know, going through the pandemic and not having that human interaction, There was certainly a huge need afterwards to boost that. I think AI is going to be a sustained boost for people to really need more human interaction and authentic conversation.

19:03You know, if you think about, for me, you know, I just watched a video about, you know, Bigfoot was talking to me about his day and going through the woods, you know. It seemed pretty damn realistic to me, you know. So it was like one of those things where it's like, OK, well, how are people really going to get to understand the real conversations from fake conversations or try to get some sort of guidance as they move forward? And I think live experiences is the place where they're going to see that. So I was very inspired to do that. And and then secondly, you know, having purpose and supporting purpose led organizations, you know, nonprofits, organizations that are trying to do good.

19:44Like it's not just about making money and capitalism all the time. So how do I, how do I help partner with an organization that's going to be able to bring that forward? So I think, you know, true North kind of combined those two things, you know, the live experiences and purpose led organization. So that was the inspiration. Where, where's the athletes come in? Why, why that? Why, you know, with athletes. Yeah. Cause I think, you know, sports, sports is, is one of those things again, with that live entertainment piece is just going to continue to grow in popularity. But then also it's not and it's not just athletes, but creators and creators, again, maybe a little bit overused word, but it comes in all shapes and sizes and creators.

20:24You know, they start with authentic conversations and storytelling that resonates culturally. Right. So bring it back. Like that's it's what a creator is trying to do is saying, here's who I am and put forth some sort of product, whether that's content or videos or whatever merchandise and say, this is what I authentically believe in. And can I find pockets of culture that resonate with this? So I think that's, you know, a component where getting those creators and athletes involved, they're going to have to have their storytelling and their authenticity in many different areas. They just, you know, from on the field to off the field now, you know, what are you passionate about?

21:02What charitable organizations are you passionate about? What, you know, is there certain merchandises, you know, from anywhere from, you know, baseball hats to sneakers to whatever it is, you know, you need a platform to express that creativity. And again, that goes from podcasters and amazing people like yourself to, you know, a professional athlete that's, you know, coming off the field and trying to do a second career, you know, after the field. So I think that's where, you know, we can help and resonate and be that platform from a creative perspective. There's a ton of similar, I mean, I've written back to my Forbes days about the lines between sports and business and marketing and also leadership, which is what I want to get into with you next.

21:43And you've worked with a lot of different leaders, right? And my first question is, how would you say all those leaders have shaped your own style? Good and bad, right? Because, you know, you take the good with the bad. Yeah, definitely. And, you know, we touched a little bit on, but it's completely different styles, which is great. And I think you learn from everybody. you learn what to do and what not to do, right? Even parents, you know, you learn what to do and what not to do when you're a parent. You know, and the same with the leaders that I've experienced through my career, certain things that I really enjoyed, certain things I did not.

22:15You know, I also grew up in a military household. My dad was in the military. So a lot of the leadership styles, especially early in my career, were sort of shaped in that linear, progressive style, you know, sort of the climbing the ladder, putting in your dues, very regimented, very specific, you know, certain work ethic, you know, being in the office 24-7, being available. You know, the work-life balance piece didn't quite mean as much in those days. But as the world's gone through a lot of changes and other generations coming up, I just don't know if that same leadership style holds water.

22:55So as I continue to learn every day and shape my leadership style, you know, my two daughters have helped me quite a bit, believe it or not, being teenagers and just trying to be more open and in touch with younger generations, how they think, how they work, how they act, you know, and then modifying. I think a mistake a lot of leaders make is just not modifying their style and making everybody change around them. It works in some cases and maybe in certain things, but in other ways, I think you're just getting out of touch. And all of a sudden, the corner office is looked at as a negative, and you're not really inspiring your teams anymore.

23:37And to me, you have to inspire first and foremost. You have to lead by example. I mean, those are things that are core that I take with me. But you also have to empower. And I think empowering, you know, a younger generation and to be leaders themselves versus dictating, I think is super important because we're losing mentorship. We're losing creating leaders of generations coming up because I just don't think it's in our DNA to do it. I was going to have to stop you there. Why is that? Because I very firmly believe and I mentor people all the time, as you know. And I know it's a big topic for you.

24:15But where's the disconnect? Why did that happen? Is it AI? Is it easy to just blame digital? Yeah, no, I don't think AI is the issue. I just think it's completely different styles and completely different mindsets as generations advance and move on. And I think it's the style and leadership tactics of a lot of older generation is in stark difference to what the expectation is from a Gen Z generation. And there's not a lot of leaders that are willing to adopt, learn, and evolve. You know, it's just like an artist, you know, like you see artists that can evolve and they have staying power and they're here for decades putting on new music.

24:56But there are others that fade in and fade out. And some of it is about evolution and can you evolve and stay relevant? And again, it kind of goes back to our culture conversation. Can you stay relevant? Because there's the internal culture and business culture and marketing culture. And can you be a leader of that culture or do you not? And you choose not to lean in and not evolve. And I think that's the killer right there. It's just the lack of evolving. It's a very similar, again, sports world overlap. I was talking to a friend of mine the other day about how the best in sports, not players necessarily, but coaches, the ones who last are the ones who adapt.

25:32Because the game changes, literally. And it's no different. Yeah, exactly. Yeah, you see some of the coaches, and I love that analogy, you know, that gets spotlight. You know, they have such a great player relationship. And again, it doesn't mean they coddle two players, right? It just means they understand. And understanding also knows when to be strict. It knows, you know, when you need to have a heavier hand in the dictatorship part of it. And then you also know when to ease up and not have that. You know, so it's really great to see, you know, great leaders evolve like that and their skill sets.