Jun 25, 2026 · 49 min · 11 segments
**Twilio used to read like a company built for developers and nobody else. Then it found one word that made every audience feel like they belonged to the same tribe…
Adam MorganGuestJoshHost
RossHost
Did you ultimately find kind of making the switch to brand side that it was easier to, to influence that perspective, like, from, from the brand side versus the-
I need a million dollars." Right? Like, that's, that's a little easier for me to make that move and make an impact than, you know, if you were a content writer, you know, that's, like, entry-level, obviously.
But that's why at my point, at the point in my career, it was like I either need to own an agency or I need to move, uh, over to the, the brand side.
I made the latter, and it, it was a matter of like, all right, now at a more senior level, how can I make influence, um, influence creative decisions and, and marketing decisions?
Were there other things that you found w- you were able to unlock by going to the brand side? I mean, you, you mentioned just wanting to have more control over the actual outcomes, but what, what changed when you kind of moved over to brand side?
I've made this creative maturity model, um, years ago that starts out, like, a level one is you just building your craft and your career, and you move up to level two where it's, like, managing people and your team and you're trying to get that through, and then it's like managing the company, and it moves all up to the, the industry.
And I feel like what it unlocked is it got me opportunities to just play at a different level, um, have influence in, in different ways.
You know, we're gonna talk a little bit more about this I'm sure later on of, like, creative leadership is, it's a double-edged sword because the higher you move up and the more, yeah, your role increases, the less creativity you're doing, and so a lot of people will just retreat.
Like, as part of my podcast, I did a, some research on career paths for creative people, and it was really interesting that it was like as you got to a certain point, a third of them wanted to just, like, tap out as, like, a creative director, and a third of them were like, "I'm gonna just quit bureaucracy altogether and just be a freelancer and focus on the craft again," and kind of revert back to that, versus a third that moved on to be like, "Why can't I be a CEO and, and move creativity? Why can't I be a CMO? Why can't I be a chief dis- digital officer?" You know? And so it was just interesting of, like, the mindset that happened around people feeling like the, how growth is tied to, to creativity, and there's this tendency, tendency to think that the only way that you're a true purist is if you're in the craft and designing or creating or writing stuff all the time.
I'm like, my job for maybe whatever it is until I retire, it's not about me and my craft.
It's about creating an environment or creating an industry where everyone else who follows me has a higher chance of success, and that creativity has a bigger seat at the table at the highest level of business.
And so in that charge, there's a lot of other stuff that I have to do that, um, is very different than what I did when I started out as just an individual contributor.
But I think it's just as important to further the, the, um, the charge of, of creativity for all.
Like, I really feel like that it's, it's critical because, like I said, there's so many people who aren't trained in it, and there are so many roadblocks that it's a lot to get everyone trained correctly to understand that, that creativity is a human thing 'cause I believe everyone, capital C, creativity, like, we're all creative as humans.
But not everyone's there, and so getting people to understand it and move along with it, especially business leaders, that's the leadership part of creative leadership.
Did you ultimately find kind of making the switch to brand side that it was easier to, to influence that perspective, like, from, from the brand side versus the-
I need a million dollars." Right? Like, that's, that's a little easier for me to make that move and make an impact than, you know, if you were a content writer, you know, that's, like, entry-level, obviously.
But that's why at my point, at the point in my career, it was like I either need to own an agency or I need to move, uh, over to the, the brand side.
I made the latter, and it, it was a matter of like, all right, now at a more senior level, how can I make influence, um, influence creative decisions and, and marketing decisions?
Were there other things that you found w- you were able to unlock by going to the brand side? I mean, you, you mentioned just wanting to have more control over the actual outcomes, but what, what changed when you kind of moved over to brand side?
I've made this creative maturity model, um, years ago that starts out, like, a level one is you just building your craft and your career, and you move up to level two where it's, like, managing people and your team and you're trying to get that through, and then it's like managing the company, and it moves all up to the, the industry.
And I feel like what it unlocked is it got me opportunities to just play at a different level, um, have influence in, in different ways.
You know, we're gonna talk a little bit more about this I'm sure later on of, like, creative leadership is, it's a double-edged sword because the higher you move up and the more, yeah, your role increases, the less creativity you're doing, and so a lot of people will just retreat.
Like, as part of my podcast, I did a, some research on career paths for creative people, and it was really interesting that it was like as you got to a certain point, a third of them wanted to just, like, tap out as, like, a creative director, and a third of them were like, "I'm gonna just quit bureaucracy altogether and just be a freelancer and focus on the craft again," and kind of revert back to that, versus a third that moved on to be like, "Why can't I be a CEO and, and move creativity? Why can't I be a CMO? Why can't I be a chief dis- digital officer?" You know? And so it was just interesting of, like, the mindset that happened around people feeling like the, how growth is tied to, to creativity, and there's this tendency, tendency to think that the only way that you're a true purist is if you're in the craft and designing or creating or writing stuff all the time.
I'm like, my job for maybe whatever it is until I retire, it's not about me and my craft.
It's about creating an environment or creating an industry where everyone else who follows me has a higher chance of success, and that creativity has a bigger seat at the table at the highest level of business.
And so in that charge, there's a lot of other stuff that I have to do that, um, is very different than what I did when I started out as just an individual contributor.
But I think it's just as important to further the, the, um, the charge of, of creativity for all.
Like, I really feel like that it's, it's critical because, like I said, there's so many people who aren't trained in it, and there are so many roadblocks that it's a lot to get everyone trained correctly to understand that, that creativity is a human thing 'cause I believe everyone, capital C, creativity, like, we're all creative as humans.
But not everyone's there, and so getting people to understand it and move along with it, especially business leaders, that's the leadership part of creative leadership.
The rest of this transcript — segmented and speaker-labeled, so you land on the exact moment something was said
Search every transcript — by keyword, by phrase, or by meaning, across every show Radar indexes
Trends — what is surging across podcasts, measured against its own baseline
Alerts — when a name you follow appears in a newly indexed episode
No account is needed to search Radar.