Why Reinvention Is the Leadership Skill AI Can’t Replace | Jason Miller & Susan Drumm

Most leaders are chasing their dreams when they should be chasing their talents. Today's guest breaks down the patterns leaders need to disrupt and stay relevant in the age of AI, why reinvention has to happen before a crisis forces it, and the simple practice that helps find clarity when nothing else works. I'm Susan Drumm, and this is The Enlightened Executive, where your personal evolution sparks your leadership evolution. Each week, we spotlight cutting-edge strategies to help executives and entrepreneurs grow in leadership and in life. My guest, Jason Miller, has spent his career in two worlds and refuses to pick one. He's currently head of growth marketing at v7, the leading platform for AI workflow orchestration. Before that, Jason spent 10 years at Sony building campaigns around the biggest names in music. He's a keynote speaker, a digital marketing instructor at UC Berkeley, and the bestselling author of Welcome to the Funnel: Down in Front. In his spare time, Jason is an avid photographer where his concert photography has appeared in dozens of books, magazines, and on album covers. Well, welcome to the show, Jason. I'm so excited to have you here.

Thank you for having me. I'm a big fan. I'm thrilled to be here. So thank you for the invite.

Yes. Yeah. So tell us more about the work you're doing and who it's for.

So, well, right now I work in— I work at v7, which is an orchestration layer for AI workflows. And that sounds very technical and fancy, but basically we are the trusted layer that orchestrates this new infrastructure of workflows that go across, you know, heavy document processing and places where you need absolute trust and audibility and the ability to scale that. So that's where I'm at now. But previously I worked in the music business and watched the entire music business fight digital instead of embracing it. I think we all know how that story ends. And then I shifted over to B2B marketing, a startup called Marketo many years ago. I think a lot of marketers probably remember Marketo, now Adobe, and then moved over to LinkedIn very early on and built out the team over there and then moved over here to the UK to do the same. And then, uh, went to Microsoft for a short little stint and then decided I like to be back in the startup land. So I'm a startup marketer and that's where I like to live these days.

Great, great. Well, so tell me a little bit about your point of view in what you do. What's the thing that you've come to believe that most people in your space haven't caught up to yet?

I think probably the biggest— I mean, the elephant in the room is, uh, you know, AI is, is replacing jobs before, you know, anyone can get up to the speed of what's happening next. And, and I think You know, what's interesting to me is that, of course, AI can't come out of nowhere. I know it's blowing up everywhere, but the Achilles heel of AI right now is that it doesn't understand judgment and relevance, right? And so I think if I look around at the most successful leaders or the ones that I look up to, I find that they lead with creativity, with big ideas. They're inspiring. They don't stay in their lane. They're constantly curious and they're reinventing themselves every chance they get. And they're this generalist wave across how everything fits together. So I think that's probably the biggest trend is entry-level roles. That's another thing. But for leadership, you know, taste, judgment, creativity, these are things that the leaders need to, you know, bring to the table to inspire the team, to paint the picture of what's possible. And that, I think, is what really resonates for me right now.

Yeah, I agree. I mean, I do think that the idea— certainly I've done a ton of work with AI in our— both within our company as well as creating our own AI product. Where we have all of our coaching resources and it's essentially an AI coach. And the fascinating thing about that is there's definitely a place for that to have this opportunity to bounce ideas off of and, and have the AI as a 24/7 thought partner. I also find there's a place where it doesn't fit, which is the true inspiration and motivation to get someone to make a change. Like, I'm not seeing that occur because it's too easy not to have accountability with an AI. Like, oh, I didn't do that. But when you have a live coach and you're like, okay, what is— in order for us to keep going, you need to— you said you were going to do this. What's getting in the way? And to pivot like that. So I know in my industry, I can see the real difference where AI can play and where it's beneficial and what is distinctly human, at least in the personal growth and leadership growth space. Yeah.

And to further your point there, I mean, if you think about it, AI is trained on average. Right? And I think it's automated. We've maybe leaned into it, at least in the marketing side. Maybe we leaned into it too much. Sure, it can make us more productive, but is it making us more productive at producing things that we don't need? Are we just cranking stuff out? And again, I think, you know, if you look at what it's trained on, it's trained on the average. There's so much room between just the average and the next level. And I think that comes from, you know, curiosity, constantly upskilling. Everyone always asks, what, how do I keep up? What's the secret? And there is no secret outside of being curious, not being a specialist, and just, you know, constantly pushing and reinventing yourself. Reinvention, you know, doesn't happen because of a crisis. It happens because you need to focus on reinvention before you need it, so it's there, so you're constantly adapting and ready. I'm quite comfortable where I'm at, but I am nervous for, you know, the entry-level jobs and where that goes.

Yeah, agreed. I do know that I love this term reinvention because at the core of reinvention is breaking a pattern that you're stuck in. And what we talk about a lot here is about what those patterns? Where do you need to shift? Where are you stuck in something? And, you know, in my own life, I've tried to always reinvent myself, from going to law school to going to be a consultant and not even practicing law, to having a degree in acting. And how that all came together, I would have never thought at the time how this would all come together, but I felt the pull to reinvent myself each time, or break the pattern of the mold of what most people would have done. And that very generalist background, as you mentioned, is what served me. How do you see that serving? Because that's a very different mindset than I think particularly kids today are pushed to specialize very early. For the longest time, it was all about what's your niche, what's your specialization. Tell me a little bit more about how you think about that and how we need to shift in this era of AI.

Susan, I was on, uh, I was on a stage at Turing Fest, which is an AI conference in Edinburgh, and I was on stage and I was arguing with A good panel is always, always has to have a bit of an argument, right? If everyone agrees, it's kind of boring and out there. But I was arguing, like, someone I truly respect, probably smarter than me in many ways, but it was the specialist versus the generalist. And we get this point where it's like, if you're a specialist, I think, you know, depending on what you're a specialist in, but majority of anything who is sort of one-dimensional, I think you're easily disposable in this day and age. And I think we're seeing that through the automation, anything that has to do with with data or processing, I think we've figured out you're, you're probably gonna need to, to spread out a little bit. And we have this term that I used at LinkedIn when it's 10 years ago, LinkedIn before LinkedIn, before anybody cared about LinkedIn at this point. We call it the hybrid marketer. And I think it's T-shaped marketer, whatever you wanna call it, but it's being really good, not an expert, but good at lots of different things. Lots of market, lots of different marketing disciplines, but more importantly, and this is where the leadership comes in. Is understanding how these things fit together. And more importantly, in the age of AI, what good looks like when it comes out the other end. And I think, you know, that's the taste portion. And it's subjective. Of course it is. But the more experience you have, the more times you see what good and bad looks like, the more times you fail. I'm not going to throw the fail fast because I think that's overplayed, but the more you see what works and what doesn't and you have that under your belt, I think Experience is probably the most underrated skill you can have right now in AI, and that plays into leadership and what you do with that. There's a great scene in The Avengers. I think it's the one where it's right before Endgame. I'm not a big Marvel guy, but this movie changed me, Susan. And there's this scene with— I was watching on a flight to San Francisco, and there was a scene where Loki and Thanos— and Loki says, if you're looking for someone to take you to Earth who has experience, I could be of service. And Thanos looks at him and says, if by failure you mean experience. And he says, by experience— I mean experience by experience. And the idea is, yeah, Loki destroyed Earth, failed miserably a bunch of times, but so did we all. But we still know what not to do, hopefully with our best foot forward. I think that's terribly underrated.

Well, tell me a little bit about the pattern that you had to see in yourself, which is the inner work maybe that you've done. I think every person that's doing meaningful work now has had to confront something something in themselves. What's a pattern that you used to have in the past, and how did that show up, and what had to change?

I think probably the pattern that was biggest for me, that, that still lurks here and there, is a bit of imposter syndrome, a bit of routine, right? So I think settling— I was, you know, from the Midwest. I was born in St. Louis, Missouri, in a very small, very small Midwestern town, very conservative, you know, religious. And there was really no way out of it. It was in between— we're in between New York and LA, right? So by the time the trends get to us, they're already gone. And so I think it's a matter of, of pushing yourself. And I hate to say that so vaguely, but here's the secret about reinvention or success or even thought leadership or, you know, going viral. If it were easy, like, everyone would do it. But that's— it's a grind, and it takes a lot of perseverance and determination, and you have to set goals, and you're going to be disappointed. There's a really great reel that my wife shared with me from Reese Witherspoon a couple of months ago. Did you see this? Where she talked about don't chase your dreams. So everyone tells these kids and everything. You've got to chase your dreams. And she says, chase your talent. And I thought, yeah, that's exactly, I think, the frame of mind that we need to switch back to. Because I mean, I don't want to kill any inspiration. Sure, chase your dreams, but lean into your talents. But not just one. Like you said, law school and acting and how it all pulls together. The leaders that I respect the most, they have lots of talents, and they sort of let the talents argue and fight themselves. Until they figure out what those 2 or 3 are, they can blend together. And I think if you can take a couple of passions, blend them together, I think that's what really makes you stand out and be unique. It was a struggle and it doesn't happen overnight. You have to stick with it. It's painful. You have to like really, really dive in and you have to know yourself and you have to ask the hard questions. And furthermore, the last thing I'll say about this, you have to put yourself out there. Uh, if you're an introvert, You've gotta be comfortable walking into a room and starting a conversation. These are the things I, I struggled with. I mean, I clearly like to talk now. I have a big personality, but that's the heavy metal voice. That's my metal, my music and, you know, photography and videography. That's my creative element, uh, that I bring together. So it's music, it's passion, it's, it's marketing. These three things, Axl Rose crossed with Jerry Seinfeld crossed with, you know, Seth Godin, not that I'm in anywhere near his level. But that's what inspires me, and that's what makes up me as an individual.

Yeah. So I was just gonna mention that you have— you've brought in multiple disciplines into the work that you do, right? From music and marketing. Tell me a little bit about how you created that intersection.

Well, it's, you know, when I worked in the music business, I didn't wanna lose the connection to, uh, free music and, and free concert tickets and, and access, right? So I started a blog and this is, this is part of the reinvention. I started a blog. I just started writing and started putting it out there. This got me into the B2B space because it was Joe Strummer from The Clash, I think, or no, Bill O'Brian from the Dead Kennedys who said, don't hate the media, become the media. If someone's, if you can't get the media to talk about you or get other people to talk about you, just become the media yourself. And I think that was a big trend, you know, 10 years ago, whatever, but it still plays today. Creator economy, putting yourself out there. Just literally, I started to blog and write and it grew into something. But the key has always for me been about access. Like, what can you do in your role to get access to something that's unique that no one else has? For me, it's access to concerts, it's access to photo pits, access to photograph musicians that I, that I love. You know, videography is the same thing. And that plays very nicely into the creative space around brand, around marketing, around digital, you know, media spends and advertising and It's all the creative circle kind of coming together. And it's also quite helpful that, you know, I have, I have a full BBC studio here with, with terrible lighting. Of course, we'll work on that, but I can film a keynote. I can film a reel. I can film a music video. I was doing photographs of some of our team members the other day to update their LinkedIn profiles. So there's always a way to pull together, but at the end of the day, I think it just makes you a more interesting person and what, what better way to combat AI fatigue than to have an opinion on something and be passionate about it.

Right, right. So tell me, you know, going back to, okay, the pattern in yourself and how you— what you had to shift, was there a specific moment or conversation or experience that cracked that pattern open for you? You know, not, not a gradual realization, but like the moment you saw it and you couldn't unsee it. Can you take us to that scene?

I know exactly where it was. I was at the gym. On a treadmill working in, in the music business. And, oh, it's gonna really date me, Susan. It's gonna date me. I was reading Inbound Marketing, the original Inbound Marketing book by Dharmesh, you know, and Brian from HubSpot. And I read it and I thought, there's a shift. There's a massive shift happening in marketing. I can do this. I can do this. And I dove straight in. And then to further like escalate it, I went to my first marketing conference and I saw Ann Hanley, who I'm sure you know, she's a dear friend of mine. She was so inspiring. She is about storytelling. She's about creativity. She's about being bold and taking risks. And I'm like, that's me. That's what I want to do. And at no point did I ever say, I can't wait to become a B2B marketer. But at the same time, I felt that I saw something that I thought I could do during a shift where there were new entrants coming in. And then I saw something that inspired me so much. That was Ann on stage, like being this quirky kind of outcast. And she didn't look or sound like any of the other speakers. And I thought, that's what I wanna do. This is my in. And I worked hard and I wrote for free and, you know, I spoke for free for years and years and years until I built up an audience. But I never stopped and, and I never do stop. And, and I think you gotta find something, find an entry point, and then find someone who inspires you so much and follow them and connect with them. And those are, you know, I reached out to Ann and got a guest blog on the Marketing Props and I was breakdancing. I was so excited. But it's those little things and momentum and, and once you get a little taste of feedback. On your own opinions or validation, it starts to make it easy and you start to become a bit addicted to it. So yeah, I think, uh, number one, find an entry point of something that's open, that's ready for the taking, and then find that one person or multiple people who inspire you and go get it, you know?

Yeah, yeah, I love those two points, and particularly just getting connected to like what's lighting you up today, right? And, and I think some people are in this sort of sea of, I don't know, nothing. The more you put yourself out there by and you're not going to wait and be like, I'm going to wait to be inspired. Try some things. Keep moving. We don't know how it's going to work out. I like to say it's a little bit like having a flashlight. Sometimes people want to see— you're going into a tunnel. You can't really see. You have this flashlight. You can see 3 feet in front of you. You know how to take the steps forward. And just because you can't see what's at the end of the tunnel doesn't mean that the journey isn't worth taking, right? And so I think that that's essentially what you're offering is to get out there, find that thing that inspires you, and then, hey, there's actually somebody who's doing that work and they can inspire you for you to put your own stamp on it.

Perfectly sums it up. And I think to add to that, I grew up in St. Louis. I moved all over the country. You know, I live in London now. Like, I'm living a life that I never thought would happen, and it happened because I didn't wait for opportunities. I grabbed what was in front of me. It's interesting, something that kind of frustrates me a bit, there was this trend a couple years ago about like, oh, if you want to pick my brain, you know, here's my invoice or whatever. And it's like everyone's so precious with their time, and I don't think it used to be like that. It used to be like, you know, if you find somebody online and, you know, they have some time, like they're happy to chat with you or you can interview them or something. But now I feel like everyone's like, oh, my time is precious, or you can't pick my brain And I feel like it wasn't like that when, when I was starting out. There's so much out there and it should be so easy to connect with people, but I think everyone's chasing viral fame and they forgot. You don't always have to hang out and speak to the most important person in the room. You can find, you know, inspiration and knowledge in, in, uh, places like right at your doorstep, you know?

Yes. Yes. When you were going through the shift that you mentioned of letting go of this imposter syndrome and getting inspired by something in someone. As you started to make that shift in your career, what was the hardest part of actually changing? What did you have to maybe unlearn or let go of?

I mean, it's still like to this day, it's being consistent and keeping the momentum and staying inspired because I think you see so many— well, I see so many people who start something and they're excited about it and they just kind of fades away or dies off. And if you do find that thing that you're passionate about or those one or two passions that you can combine, it keeps it interesting. So you're not just— I'm not just a B2B marketer. I'm a B2B marketer. I'm a, I'm a photographer. I'm a creative, you know, I'm a music lover. You have to have a way to pivot when you get frustrated and find that blocker, right? So if I get frustrated with music photography or whatever, I'll switch over to portrait photography or something. Or if I'm, you know, frustrated with demand gen marketing, I'll, I'll go find some inspiration. We went to the Brand Museum in London. I didn't even know there was a brand museum, but it's just having pivots but that are still connected to the overall goal. And like, you see that today too. What works on LinkedIn? It's like not about followers anymore. It's a love, completely level playing field. It's about showing up. It's about being consistent. It's about having an opinion on something, on anything, and not being afraid to share it. Not being a, there's a contrarian marketing jerk phenomenon happening right now where people are just, you know, pulling Donald Trump quotes and stuff and trying to rile people up. But you know, at the end of the day, you have to have an opinion and you have to be curious and you have to be consistent. I feel like I'm dragging this one on, but ask a question on LinkedIn. You'll get, you know, 10, 20 responses of everyone trying to outdo each other with the best response. Like I know this, if you ask it in a private community that's trusted, you'll get 10 to 20 answers of people genuinely trying to help you. And I think that's the space that I like to shift over to, but I think you have to be active and, and, you know, That authenticity piece.

Well, if there's like one framework or practice from what you do that you'd want every leader listening to practice or think about, what would that be?

I think there's a couple of things. I think one is every single day, first thing you do in the morning, don't look at your phone. Don't log in to check your HubSpot dashboard. Write down what's on your mind, how yesterday went. Write something down. That was number 1. Number 2, be comfortable on video. I know text-based, like, no, video's supposed to take off on LinkedIn, whatever. And I know that text-based posts probably outperform still, but I think moving forward, I think you have to be comfortable on video. You have to be comfortable with yourself. And I think you have to figure out a way to get your personality to amp it up a little bit. I'm on TikTok and Instagram, but I focus mostly on Instagram and LinkedIn. But if you look at the loudest people on TikTok as an example of where this is all heading, right? They're not necessarily sharing groundbreaking news. They're likable and they have big personalities. And I think if we can bring that more of that into the B2B space and into the leadership space, I think you look at like the CEO of McDonald's and the videos he does on LinkedIn, he's like, I wanna hang out with this guy. He's a cool guy. He's not stuck up. He's not buttoned up. He's just a cool guy. That's a normal guy with a, you know, insanely, uh, stressful job, I'm sure. Yeah, I think it's just being more comfortable with who you are, putting yourself out there more, writing every single day, and don't lean in too much on Claude or GPT for your writing. So I mean, that's kind of what I would say.

And so if somebody is stuck or sensing that something isn't working about how they're leading or living, and maybe they can't quite name it yet, what would you say to them? Where could they start?

This just popped in my head because my daughter was watching Happy Gilmore 2 last night. I still haven't seen it, but like, this sounds so ridiculous, Susan, but you gotta find your happy place, right? You gotta find a place where you walk into or you go to and you're just there by yourself with your own thoughts and you have to be comfortable there. And, and I promise you, things will start to enter your mind, uh, out of the blue. And, and like, for example, for me, I love antiques and old stuff, or I love a music store. If I go into like Thank God we still have music stores and bookstores here in the UK. I'll walk into a music store, I'll find an old record or a new record. I'll go to a bookstore. I mean, I'll walk out with 10 books. I think it's just, you have to put yourself out there, find your happy place. My happy place is a music store, a concert, a bookstore, anywhere that I can just grab knowledge and ideas and steal them, put my own twist on them. So what that looks like for Or what does it look like for you, Susan?

Where's it? Oh yeah. You know, I was just, as you were talking, I was thinking about, for me, it's, I love being in the forest. I love having trees around me. I feel this sense of power and majesty and calm and inspiration from trees. Like, I swear I'm a tree lover. Like, and that's why I love hiking. And it's funny that I live in the desert because there's not actually trees out there, but I still like, for me, it's just a different landscape. I'll find the tiniest little flower or interesting the way a cactus is shaped. Right. But I love going all over to do that. And so I feel like being in nature in general, but in particular being around the trees and a forest is my happy place. There's something about my energy that just gets connected there.

I think your blood pressure drops automatically, right?

Yeah. Yeah.

But you point out something interesting, like these little details, you start to notice things. I can go to the same record store, same bookstore, and I'll always find something new, even if the stock never changes, you know? So there's something about that. I would imagine that A lot of people can't answer that question. They would bypass it by saying, oh, I don't have time to, you know, do that or something.

You know, it's interesting, but that would be a good way of measuring how often are you in your happy place. Is there a way you can at least get there once a week?

Yeah, I mean, and again, it doesn't have to be a physical space. I mean, it could be, you know, I have a record player here with, you know, hundreds of records. So, uh, another happy place is sitting on my bean bag with my 1970s headphones and the with, uh, reading the album credits or whatever that— and I'll— yeah, we'll pop in my head something.

Yes, I could totally agree. Do you know, for the longest time I would do my meditations, use— right before I meditate, I had this spray of like a pine. It was like a pine essential oil, and I would spray that, and then I could go into my meditation even deeper. And I noticed the distinction between that scent and being able to do I can't get to the forest and I gotta start my work day. There was a way I could bring it to me. And maybe that's something and an idea for people to think about is not only where is your happy place, but let's say it's the beach and you don't live near the beach. Well, you only gonna have your happy place anytime you just go on vacation. Is there something about the beach you can bring to you that will have you connect back to the energy of that?

I love that. I love that. And you know, it, it does. I mean, this is one of those things that I think people might think is being fluffy, But until you try it and you're like, I need to do more of this, then, then you need to remind yourself that this works and this helps. Every time I have a problem, like the biggest problem or the biggest challenge, I can't figure something out, I will do, perform one of these things that I mentioned. And I promise you something will come into my mind. Will it be the answer? Will it be the most ridiculous thing ever? Who knows? But something will happen if I allow the moment to happen.

Awesome. Well, I really appreciate you coming on the show. Can you share a little bit about where people can learn more about you and your work?

Yeah, so v7labs.com is v7. So if you're interested in AI workflows, agents and skills and all the stuff, the infrastructure of the future, you can look us up there. Jason Miller on LinkedIn, feel free to add me there. On Instagram, I'm Jason Miller CA, as in California. If you're ever in London, this is another thing, like I am spoiled that I'm in London and I walk outside and the energy of the city is everywhere around me and I thrive off that. And I wonder one day if I wanna pull like an Ernest Hemingway and have a seaside cottage where I retire by, you know, the English seaside or something. I'm thinking, not yet, not yet. I gotta get this outta my system. But yeah, thank you. What, what a fun conversation. So thanks again. Really appreciate you having me on.

Thanks, Jason. And if you like this episode, you're not gonna wanna miss my interview with Braxton Kilgo, who helps us discover how purpose-driven leaders turn small acts of kindness into scalable impact. Let's lead the way! Hope you enjoyed today's episode, and I'd like to point you to the next important step. Hit the subscribe button and the bell to get notified when we release new content. I'll see you on the next episode of The Enlightened Executive.