Your business still needs your voice 📣 Jess Jensen

My belief is that your imperfection is actually your magic because it shows your humanity. It shows that you're likable and relatable. Someone's seeing what you're doing. It takes some time, but if we just go into it with a little bit of a long game in mind and know that we're investing here and it will pay off because brand building is not an overnight success. Pushing yourself to do hard things. It is both the challenge of a lifetime because you're pulling yourself out of a comfort zone that you know so well, but it reminds you how young we are and how much capability we have to grow and iterate and evolve. And for me, I kind of started to forget that.

This week's Millennial Master is Jess Jensen, founder of Copilot Communications. Jess spent more than 20 years inside some of the world's biggest companies, working through the early rise of digital and social media when most businesses were still figuring out how the internet actually worked for marketing. Over time, her work shifted into something more strategic, working with senior leaders and executives on how they show up publicly and why a company brand alone is often not enough anymore. Today, she helps founders and leaders build a professional brand that actually supports the company instead of hiding behind the logo. In this episode, we talk about why your business still needs your voice, how corporate messaging makes people tune out, and why trust around the leader takes time to build. Jess, welcome to Millennial Masters. Where are you joining us from today?

Thank you for having me. I am in Portland, Oregon.

So we're going back to America this week. So let's get straight into it, Jess, because before we get into what you do now, I'm curious to hear where did your career actually start?

Yeah. So it started, uh, at a small agency, boutique agency, under 15 people, which was actually a great first job because you learn a little bit of everything. And it was a design firm, this is early days, mm-hmm, in the 2000s. So this was when it was really about web for the most part. Social wasn't around yet. Search wasn't around yet.

There was a bit of MySpace type of stuff, but it wasn't called social media back then. Yes. Yes.

Yeah. And it wasn't available to corporations, so it was really a new little thing at that point. But I had a wonderful boss who was a mentor to me, and I got to do, again, a little bit of design, account management, client-facing work. It was a wonderful first couple of years out of college.

Mm-hmm.

I did that for about 5 years, and I more and more, as I got closer to our clients and I started to understand there was a lot more going on with the business outside of just sort of the promotion P, if you will, of the, the marketing 4 Ps, which is really what the agency largely touched. And I was curious just to learn more and be closer to things like pricing and distribution and, um, even innovation, product innovation. So, um, I decided to go back and get my MBA. I hadn't been a business major in undergrad, so I wanted to get that under my belt, and I was still fairly young in my early 20s. So, I went to business school for 2 years down in Southern California. And then from there, I kind of launched into this sort of Fortune 500 chapter where I've spent about 20 years. That wasn't intentional, but that's just sort of—

So, the MBA was your gateway to the Fortune 500 companies, you say?

I guess you could say that. I mean, you know, you can never A/B test your life. And so we'll never know, could I have gotten those jobs had I not done the MBA? I don't know. I like to believe, given how much I spent on it, that that is the truth, that it was the gateway. So therefore there was an ROI on that investment. But I, I will say my first job out of business school was at Nestlé. And at the time, Working for a consumer packaged goods company, like a Nestlé, Gillette, Procter Gamble, that whole world, that was kind of, that was like the blue chip, right? That was what every person I met with, every mentor said, go get CPG experience. You're going to have this bedrock of brand management underneath you, and then you can do whatever you want after that. So I worked with—

What was the experience moving from a small boutique agency with 15 people where you had, where you were able to dabble into all sorts of tasks? To moving in a corporate role, which are quite strictly defined in terms of responsibilities?

Yeah, it's a great question. It was hard. It was hard. I don't know that I would say it was necessarily the size of Nestlé that was the big differentiator versus the boutique agency, but it was more that, to be honest, my first job out of business school, I was a brand manager for the confections and snacks division, and specifically the Valentine's Day holiday collection. So that was my P&L, Valentine's Day. But the reason I share that is because at the heart of that job, I was really a general manager. It was like I was a mini CEO for this confections business. And I had a background at that point, really, again, in the kind of more campaigns, promotional marketing side of business, but I hadn't, other than business school, I hadn't had practical experience yet in pricing strategy, product development, supply chain, finance. I mean, that was my first chance to even manage a P&L. So, there was a lot of newness that I had to really quickly ramp up on in that Nestlé job. And I did, but, you know, in the beginning it was the first 6 months, it was bumpy for me, for sure.

And after Nestlé, you moved to another well-known brand.

I did. So after Nestlé, I moved to Adidas. That was partly because I, I wanted to return to Portland, which is where I'm from originally. And Adidas, well, as you know, they're headquartered in Herzogenaurach in southern Germany. Their North American headquarters is here in Portland. And so there was an opportunity to both come back to my hometown, but also continue to elevate in the digital marketing space. And Adidas job took me out of kind of broad brand management, which again was such great training and allowed me to, again, for the first time, really focus all of my efforts in digital. And that's when digital was really rising as a prominent component of the marketing communications mix.

That was the rise of Facebook as well. If I'm correct, you started the Facebook page for Adidas, haven't you?

I did.

Yeah.

So Adidas back then, and I should say Adidas, 'cause you're pronouncing it correctly. I'm not. So Adidas was really divided back then into kind of two big buckets. It was sort of sport on the pitch, on the court performance side. And then it was the off the pitch, off the court lifestyle side. So I was on that lifestyle side. So I worked on both like, you know, with Missy Elliott and Snoop Dogg and sort of the skateboarding culture.

Those were the days.

Yes. Yes. Yes, yes, back in '07, '08. So it was a lot of fun. It was kind of my first chance of dipping my toe in some of those sort of celebrity partnerships, kind of the beginning of influencer culture was rising. And as you said, Facebook was really the dominant platform, which had recently—

Well, there was Twitter, there was Twitter as well, yeah.

There was, but Facebook was at that time much more, and it still is today, much, much larger from a user standpoint, and it was being used—

Especially consumer side.

Yes, yes, especially consumer side. And it was being used now, again, early days by corporations, and that was still fairly novel.

Jess, what were you chasing then in those roles as you were moving up the corporate ladder? But also, I'm interested to hear, was there a point when this work stopped feeling energizing and it felt more heavy?

I wouldn't say it felt heavy. I think that things were changing so rapidly with digital marketing and social. And that again, in the 2000s, it was a really interesting and kind of rollercoaster-ish part of marketing to be in. Even after I left Adidas and I went to Microsoft, which was my first foray into the tech industry, I was performing to do a lot of what we might call now evangelism, internal evangelism, trying to convince and influence marketers that were much more seasoned and senior than I was, hey, this is a thing and it's gonna be a thing. And we, we need to invest in it, um, both from an organic standpoint, building communities and figuring out how we go about at a global level for a brand like Windows. How do we even like organize ourselves so we show up as one brand? And then also from a paid standpoint, paid media was beginning to bubble inside of social, but back then it still wasn't necessarily taken very seriously. It was less than 10% of the media mix to give you some context.

And when did you realize that you were doing well on paper, but something wasn't right? There was all this constant change and in a way you were learning on the job because none of this you could be trained during your MBA or your university course. And even now, whatever you would be taught or any book you buy is pretty much outdated by the time it reaches the shelves. So why did you decide to change track?

Well, I kept going within the tech industry for quite a while. So from Microsoft, I went on to Qualcomm.

Qualcomm was the first business-to-business or B2B That was with the rise of smartphones as well.

Yes. Yes. Right. Great, great build. So yeah, Qualcomm, for those that don't know, makes the Snapdragon system on a chip or SoC. And the Snapdragon chip is inside of just about every Android-based device on the planet and a bunch of other devices that now require chips, which almost everything does.

Tablets, few laptops.

Yeah. Yeah. Yeah, it's in automotive, it's in, you know, appliances in our house. I mean, Qualcomm's technology is hard sometimes to understand and kind of get your head wrapped around, but it is in many ways the easiest way to explain it is Qualcomm was sort of the Intel of mobile. It was the way that we really took mobile and made it, connected it to the internet, made it fast, robust, app stores, all of that, right? That all came out of a lot of the R&D that Qualcomm was behind. So, but as a marketer, especially in the social and digital space, like those are more complicated things to explain than a pair of Superstars. So it was a good challenge to move into B2B and to try to build not just the social motion, the corporate social motion globally, but then eventually an influencer program and advocacy program, the Snapdragon Insiders. And that's where I also started to work more one-on-one with our executives.

And that, in a way, gave you an idea for later on, right? Take, take me through that. Take me, take me to what you're doing today.

Yeah. So that one became kind of the, the seeds that eventually blossomed into what is today Copilot Communications, which is my company. So I launched Copilot in 2024.

Mm-hmm.

And the, the focus of the practice is really what I had been doing at Qualcomm for the last 5 to 6 years. Mm-hmm. And it was taking all of the sort of experience I had with social and digital and beginning to kind of coach and educate and just partner with our C-suite, who at the time didn't— there wasn't much development there in digital properties. They were doing a lot of the basics from a blocking and tackling the PR side, you know, press interviews, you know, keynotes and fireside chats, those good things were of course already happening for them back in '17, '18, but there really wasn't a digital footprint to complement all of that. And we saw an opportunity there and I kind of ran with it.

So when you didn't have the senior leadership role and you didn't have the job title and the company names, did you, what did you feel that you lost and what did you have to, in a way, rebuild as you started your own business? And consultancy?

Yeah. Well, I think that first of all, a lot of us through the pandemic in that 2020 through like '23 chapter, I think a lot of us did some sort of deeper thinking, reconsidering, you know, a little bit of—

Soul searching.

Soul searching. I'm sure you've heard this story many times before. Maybe it—

maybe you— Haven't we all? Like you said, we all did a little bit of that at least.

For sure. And so I think that was piece of it really. It was like this chapter where I, I was working remotely for the first time. I had never not gone into an office, so that was really new. I mean, all of us, many of us, that was the first time. And I was recognizing that the work that I really got the most sort of fortification from was working with one-on-one with these leaders. And then getting to work with my team directly. So it, I, I had done a lot of years already, put my time in on the campaign side and sort of the corporate marketing side. And it was, it was fine, but it wasn't necessarily invigorating anymore. And I think you get to a certain point too in your career and or your, your life where you kind of go, okay, you know, I've maybe got 10, 15 more years to really go after it. Professionally, how do I want to shape maybe this last 1 or 2 chapters? Do I want to just keep kind of chugging on this trajectory, or is there an opportunity to maybe take the things that I've built expertise around and I get joy from and maybe pivot a bit?

So one of the specialties that you work both in the corporate world and now with the corporate leaders, Jess, is you're working with leaders who still stay quiet and you're working on their visibility. And a lot of entrepreneurs and business founders, especially once they start growing the business and having more staff, they in a way tend to step back and let the brand name or the business and staff speak for themselves. But am I right in thinking that you believe this is a mistake? And if that's so, why? I do.

Again, I don't think it's an or, it's an and. You know, when you have a business, whether you're a business of one, you're a solopreneur, or a business of like Microsoft, 95,000 people worldwide, yes, you have to have a company brand, right? You need to have a logo and a tagline and a website and all those good things. And we need to know. You know, what you do, what you sell, what you, you know, what, how you package company. Check. In addition, um, especially if you are a small to midsize business owner or leader, mm-hmm, building out your persona, your sort of your founder story, your, your origin story is really—

shall we call it part of personal branding? Just because that's the term that's currently used today, even though it doesn't have to be that, but just for a wider understanding.

Yeah, I think so. I mean, I sometimes use the word professional branding because only because I feel like in all the conversations I've had, there is a common red thread where a lot of leaders or founders, they sort of have, there's some cognitive dissonance. They sort of grapple with, like, you know, I don't want this to be about me. I don't want this to be showy. Right? Like, it's, you know, it's the people, it's the business, it's the product, right? And so, they're reluctant in many cases because either A, they don't want to put themselves out in front to sort of be puffed up and big, right? That doesn't feel like them. And, or, or second, they just frankly don't really know what to talk about other than my company. Like, that's, that's the easy part. What else am I actually, what does thought leadership look like for So, professional branding to me is, is the term that I tend to land on because to me, you're doing it not just in service of your own personal interests, you're doing it in service ultimately of whatever this company or division is that you're representing.

Oh, if a business leader then says, I don't have anything to say, what do you hear underneath that?

I hear probably they haven't taken the time to sit down and slow down, which I get when you're running a business, there's not a lot of time to think about what they stand for. A question I'll ask often is—

And that doesn't have to be about politics, right?

No, not at all. In fact, probably it shouldn't be unless you're in a political, unless that's your company.

Or social issues either.

No, not at all. And I know we had an error.

I think that's what people get confused about. If we're gonna dig into this one a little bit, they think when you ask them, what do you stand for? They would think, who am I supporting politically or what causes I'm supporting?

Yeah. Yeah, I get that. And I know we had kind of this couple of years where there was a lot of, even at the Fortune 500 level, a lot of CEOs coming forward and, you know, talking about these issues that were so hot again from like 2020 to 2024. I don't think that you have to do that. And frankly, I don't know in many cases if it actually is serving your business. To do that. There's some, there's some edge cases, of course, but generally speaking, when I talk about what do you stand for, it's more around the idea of whether it's the kind of leader that you are. Servant leadership comes up a lot in the conversations I'm in. The aspiration for leaders to want to kind of put their people out in front, shine a light on the work and the others, and they're sort of back here, you know, cheering them on, um, or mentorship, um, or taking the time to help people that are early in their career craft a bit of a journey or a path, right? A lot of those things that are extra and maybe not traditional sort of leadership skills, those are becoming more popular, much more common today. So stuff like that would be one. Another could be, it could be nonprofits or sort of organizations that are close, near and dear to your heart. You know, you volunteer, you know, you're interested in, in with environmental causes, or it could be around equity in education, or it could be maybe it's animal welfare. And again, we are getting into social issues here, but it doesn't need to be political. It could just be, you know, I lost a grandma to Alzheimer's, so now I'm a big supporter, you know, of, of R&D and funding for Alzheimer's research. So that can get peppered in too. And then I think it's also about using your platform to highlight others. I talk about this idea of being of service to others, whether that's your employees, your partners, vendors. If you build that influence and that authority, then you have this power where you can sort of shine the light on other people and groups. And like, what a magical gift to be able to give people publicly.

What you would recommend, Jess, is that any business of any size, if they want to stand behind a cause that's not political or a social one that can be quite divisive. Then charities, animal welfare, as well as nature supporting, say tree planting seems to be quite a popular cause, planting trees and also maybe curing various diseases. Is that my correct assessment?

Well, I mean, those are great examples of if one of the editorial territories that, that leader and I often have kind of landed on for them is something that's a little bit more sort of personal. Those are examples of things that could be a personal cause they want to talk about occasionally. Again, the other territory is often around the form of leadership, the style of leadership that they hope to have or aspire to build. Another one is kind of futuristic predictions, right? Like, here I am, a leader who's been in it for 20, 25, 30 years. I probably have thoughts about where I think whatever my industry is, is going. So, talking about the industry at large, not just my company, because frankly, you know—

Or at least a sector.

Yeah, a sector, right? So, frankly, you know, again, it's always— there's always going to be a piece of that narrative platform or that strategy that's about the company, of course. But if it's all that, or even 90% that, frankly, a lot of people are going to tune out because it's just, it just becomes kind of PR noise. So how do we balance?

And that's what I wanted to come back with. Now you hear most companies supporting some sort of charity or cause. It's not something, it doesn't feel special anymore. That's why maybe some of them lean into the more divisive or political-related causes in a way than they used to stay in more neutral territory?

Yeah, yeah. I think this gets really personal and individual to the leader, but we always want to have the larger business in mind. You know, it is, again, that's part of why one of the first things that we do when we get together is we get to know them, we interview them, and then we develop this Narrative platform, which really is just another way of saying here's the 3 or so themes that you— we're gonna again and again build your brand around. And they all are germane and authentic and honest to who you are, of course. And so if a certain social cause is part of that narrative platform because it actually helps the business and is again true to that person. Great, but it doesn't have to be.

So, just which part of the advice you give to leaders, they resist at first, but then later come back for?

You know, you talked about it. I've got your, one of your great blog posts that you published. This is the 52 Founders Taught Me This Year one from a couple months ago. And you've got a great section here, section 3, about how you show up. And so in there you talk about repetition, building trust, leading with value before asking for attention, and then keeping your language simple. I couldn't agree more with those three, and they're baked into my practice as well. But to answer your question, I would use that keep language simple as maybe the one that in the beginning, especially in the tech industry, but it's easy to hide behind jargon. Yes. Yes. And I think especially again, when you're at a certain level, you've been in the industry for years and years, you almost forget that the way you're speaking is actually not layman's terms. And that certainly if your target audience is a real subset of say B2B tech software, then fine, great. Use all that jargon. They're all going to understand. But often we're talking to a broader audience when we're at that level. And it might even be that we're talking to future talent. And so I often have to work a little harder to sort of rebuild the muscle of, okay, I know you know all of this and I generally understand what you're saying, but how could we write this like we're talking to a middle school kid? You know, how do we make it simple? Because honestly, that actually shows your wisdom and your expertise even more because you're able to simplify your message.

And is that something that AI can help with nowadays?

For sure. I mean, I've, I've, I've literally done that. I've literally put in something that, you know, I read, even an article I'm reading, and I'm like, oh my gosh, this is so much language. And just been like, I want you to distill this down to a 6th grade level for me. So yeah, AI can definitely help with that. I mean, AI is a fantastic partner in crime to the work I do. But I'm sure you've had loads of conversations about this already, and I know we're all thinking about it every day. But I firmly believe that it's that combination, right? It's that combination of knowing the person and being able to sort of be that final editor to say, is this you? Does this land in the way that like a human would write it? So I, um, I'm a fan of AI as a partner for sure.

Do you use ChatGPT, Claude, Gemini?

I've used them all. I actually ran an experiment last year where I would put in the same prompts to ChatGPT, Claude, Gemini, and Perplexity. And I did that with 4 or 5 different subjects to see where I got the best result. Now, again, they're changing so rapidly that already my experiment from a year ago is old, but I tend to lean in now mostly on ChatGPT and Gemini.

Now let's talk a little bit about, uh, some of the founder life that you possibly experienced yourself, but you also know it from the leaders you've been working with because at the top, It can feel really lonely. And why do you think so many founders and leaders feel isolated, even though they're basically constantly connected to their team and possibly other peers?

Yeah. Um, I, I would surmise there's always a degree of anybody that either reports to you or their, um, you know, their livelihood is sort of reliant in part on— you're always going to be a little bit guarded with the candor in which you speak. That's human nature, right?

Yeah.

So I think when your team grows and you're, you're responsible for a bigger and bigger and bigger group of people, then that there's more people there that maybe struggle to, to be completely transparent with their thoughts and their input. I think it can be, I think a lot of people are very intimidated by sort of that C-suite, um, even if, even if you're running a company of 100 people, it's, that's intimidating, you know, whether it's because you're younger and early in your career, maybe you don't feel like you're as technical as they are. A lot of those folks have it, you know, have a, a lovely charisma about them, which makes them great as a orator and speaker and inspirational leader. But it can also, again, kind of make it harder to approach them. And then I think there's just the, there's the scarcity of time, which I know we all feel that, right? The never-ending inbox, never-ending, all the DMs, like all the things, right? It never ends.

Slack.

Yeah.

Even, even written correspondence, depending on the role, you can have even more. Yeah.

Yeah. And I think when, again, what I've seen is as you move up, there is just more and more and more that you're CC'd on and you're FYI'd on. And it's like filtering through that, you know, you could, you really have to be intentional to say, okay, I'm, I'm done with that. And now I'm going to go sort of build relationships. And it's, I think a lot of senior leaders maybe put that relationship piece kind of lower on their list. Unless there's a real pain they're trying to solve. And in my experience, the relationships are, I mean, they're everything. They're how you get new customers and clients. They're how you get referrals. They're how you build partnerships, and it's how you build trust online.

Speaking about trust online, where does LinkedIn actually help and where does it give false confidence when it comes to that?

Well, LinkedIn has changed a lot. I think, you know, we probably all feel that.

Mm-hmm.

Um, just for a few, a few statistics to kind of ground us, you know, if you look at the numbers, uh, from 2019, right? So just before the pandemic to 2025. So in that 5 to 6 year span, LinkedIn doubled in user base. So it went from about 480 million users to 1.1 billion. So that's pretty dramatic. Now, understandably, all, again, a lot of us went home, so a lot of us are spending a lot more time online. Yeah. And there was also a lot of transition with jobs and career, the great resignation, all that was was happening, but it benefited LinkedIn. It really just kind of exploded the usage of that platform. So that's one. Two, it's now become the largest writing platform on the web. So bigger than, you know, Substack or any of the other blogging platforms, like people are using it to publish longer form, short and longer form content. And I think that it's moved. I actually have a post going that just went live this morning on LinkedIn about this. I used, I used a boy band analogy. So LinkedIn, as boy bands have evolved, LinkedIn has evolved from being really a place that is my kind of my online resume, right? My digital CV, sort of set it and forget it, to tell me not what you've done, but what you think. So the publishing side or the posting side of LinkedIn has become much more robust and important. And more interesting, frankly. So that's where I spend a lot of my time with clients is, uh, this is a territory where a lot of your potential customers, clients, partners are.

Mm-hmm.

Where half the audience there, you know, makes over 6 figures in US dollars annually, which no other social platform can boast that. So you've got a lot of, um, you know, educated professional folks that have potentially money to spend, right? If you are a business owner, this is a good space spot to be, but don't just want to look at your CV, right? They want to look at, they want to see what you have to say. So say something.

Yeah, people don't usually go through that. The CV part of LinkedIn is pretty much outdated in a way. It's more for the job side of, because LinkedIn has also increased more its footprint in terms of job seekers. I would say.

Yeah, it's, and I think recruiters probably get executive recruiters and so forth, you know, talent, like the folks that—

Headhunters, et cetera. Yeah.

Yeah. But if you're a business owner, I think that you're looking, you want to maybe get a quick little, oh, where they live, where are they from? Great check. But then you want, the first thing I do is I go look at the feed and see what they've published.

So in this case, you need to be very careful what you post on there.

Yeah, for sure. But I mean, that's been the case with social, gosh, since inception. Yeah. And you can delete, I mean, you can obviously screenshot, but you can delete if you really have second guesses about something.

But once something is on the internet, even for a second, there will be a trace of it somewhere forever at one point. Jess, then what would you say that like a healthy professional network really looks like? In practice, both in real life, but also digitally around your business and brand?

Well, it's funny. I think I've always been this way, but again, the pandemic really shone a light on it. The idea that our, like, professional and our personal lives are these sort of bifurcated, separate buckets, sort of who I am at home and who I am out in the world are totally different. I get, like, if we go back way back, right, to like the '50s and '60s, like, I get that there was probably more tradition, even gendered roles, right? Like, who's home, who's working, and those felt very different. I've never been that kind of person. Like, certainly there's things that are private. We all have moments or elements we want to keep private. That's totally fine. But like, who I am at work is who I am with my friends. And What I write about on LinkedIn now, yes, it's oriented toward communications, right? Because that's the business I'm in. But I, like I was just sharing, like, I mean, I'll throw in a boy band reference because I grew up listening to boy bands, right? Like that's part of my—

Which one's your favorite?

Well, I mean, I was the era of New Kids on the Block and Backstreet Boys. So, but I mean, they've been going on since the Beatles, right? This has been, this is no new thing. So I, I say that just to illustrate, I think that the way that you nurture professional relationships is the way that you should nurture your personal— I mean, they're relationships. So it's— go ahead.

I just wanted to touch there because you're basically an advocate of showing your real self both to work as you would be in your personal life. Doesn't these boundaries sometimes cross maybe in the negative side? Such as the way you present yourself, as the way you dress, or the any other parts that would not be as professional as some would expect, especially in leadership roles?

Yeah. Yeah. Again, I think, I think it's a Venn diagram. I think there is, um, and the Venn diagram, I think, used to be almost just two circles, just barely touching at the border. And I think that's center point of the Venn diagram has gotten bigger and bigger and bigger, where this is who I am both at work and at home with my friends and with my colleagues. This is what I believe. This is what I stand for. This is what I'm interested in. But there's still the other portions of the two circles that are more relegated toward my private life and maybe how I show up professionally.

So is there something that you wish more founders and leaders would slow down and notice when it comes to that?

I think there's still an aspiration and an intention to be produced and to be perfect.

And social media has something to do with it as well.

Yeah. Yeah. I mean, we know, you know, places like Instagram sort of famously have given us all a level of envy and aspiration that we maybe never would've known about had it not existed. And that's probably not the healthiest thing. But I, my belief is that your imperfection is actually your magic because it shows your humanity. It shows that you're likable and relatable.

And how can you show more of these imperfections and likability if, um, you still have pressures from a PR point of view, communications and so forth?

Yeah, it's a, you know, it's a dance. And again, this gets to be so, it's bespoke to that leader. But it's even, you know, sharing videos that are, you know, yes, you want the lighting to be right. You want to have a sense of like, what's the point? What are you talking about? What is the gist of the video? So you're going to have some sort of outline. You know, maybe there's, maybe there's stuff behind you that are books you've read or a handprint from a kid's picture when they were 3. Allow— maybe you stumble and you just keep going, right? And you just sort of allow there to be more of who you are in the picture, um, and not feel like I gotta go redo that whole thing again. And, you know, the production value wasn't— it's like, it's actually— think about it, like, most TV spots, like traditional TV spots, are heavily, heavily produced. We know they're ads. Like, we know it. Like, we might watch it if it's interesting and compelling, but like, we know we're being sold to. I'm not saying there's not a place for that, but if we're talking about building a person's, a professional brand for an individual, I don't want to feel like I'm being sold to. So I kind of want you to be imperfect.

In this case then, why would you say that founders do too much instead of doing less when it comes to their professional and/or personal brand? You, you slightly mentioned that they still have this tendency to overproduce or be ultra-polished, especially when they feel that they're representing the business or the company.

Yeah. So you're asking where does that come from?

Is there something that they do too much and they should be removing besides the polish?

Yeah, I think that, I think that there is an assumption that if I care about this product launch, this event, this corporate partnership, everybody is going to care about it. And your employees do, right? It's, it's probably helping their stock price. So that's good. You've got those guys on your team, probably the partners and the vendors in which you bring it to life. They care. Maybe shareholders, right? If you're publicly traded, they care. But there's a lot of people who are probably following you that don't fall into one of those categories. And so, um, I think there's a tendency to talk a lot about like, look what I did, look what we did, look at how we look at this moment in time and not ground it in the why should I care. Right.

And how can they make people care?

Yeah. I mean, I think it's coming, having an audience.

I know that's a trick question, but No, no, no.

It's a good one though. I mean, having an audience-first mindset. So if I, I think this is why understanding your target audience and even developing personas, your ideal personas around, I'm hoping that I can talk to this person, this person, and this person, their pain points, their concerns, their what's keeping them up at night is this. And so if I believe that to be true and I slow down to kind of think about that, have empathy. Right? Have basically have empathy. And then I go, and I also wanna tell them about this great new product that we just launched.

Mm-hmm.

Now I'm gonna try to tie those together. Why should that person that I want to engage, follow, comment, you know, even reach out to me, why should they care? And how does it change their life? That I launched this product. So taking the time to stitch those things together can make any content, whether it's on social or somewhere else, so much more impactful because it's got that empathy piece built into it.

And is there a leader and/or business right now— they obviously don't necessarily have to be your clients whatsoever— who you think they're nailing this, that they're balancing the why as well as their business interests and they're resonating with their audience?

Yeah, there's a couple that come to mind and I'm going to, of course, lean into marketers and founders because that's a lot of who I follow. But 3 that come to mind, one is Dara Treseder. So, she's the Chief Marketing Officer at Autodesk based in the Bay Area. And I love that she does a great job of combining the professional and the personal. I would say probably is more transparent than most C-suite leaders are, but always is very, you know, also looks polished, also comes across very professional, but she's a whole human. So, that's one. Two, in the same vein, you're going to see a red thread, all three of these. Sara Blakely, so founder of Spanx, and I believe first, like, self-made female billionaire in America. Sold the company. She's got other stuff going on now, new company, Sneaks, but she is a classic, like started her career going door to door selling fax machines. I mean, she's literally built it from the ground up with very little outside funding and became very, very successful. And now just has this both business smarts, but also this kind of whimsy and playfulness and kind of, again, levity about who she is, what she wants to do next. So, I love her content. She's, she's bigger. Dara, I watch on LinkedIn and then Sarah Blakely more on Instagram. And then Frank Cooper is another one that I like. He is the CMO at Visa.

Okay.

Also in the Bay Area. And he is, but he's got this really diverse background, not dissimilar to sort of the way I went from one industry to another. He's also He's worked in finance, he worked for like Def Jam Records, like he worked for Pepsi, you know, he's got just this kind of really broad industry background, but always in, you know, different marketing roles. And he also brings this sort of culture and humility to his content. Still, you know, plugging Visa and talking about big moments in time for them, of course, where that's relevant, but also like listening and responding. He's actually responding to one of my comments, which I, I even nudged and I said, yeah, I'm sure this is his team, but thanks anyway. And then he came back a second time and said, no, no, nope, it's me. I swear. So I, whether that's accurate, I'm going to believe it is. He's trying, right? He's trying to sort of be in the mix and actually getting engagement and conversation that feeds future content. So I think Frank is one to watch too.

My follow-up question to that is then what do you make of these leaders, founders who hire consultancies and other businesses to run basically their LinkedIn, post daily inspirational, viral, follow them through their lives, et cetera, whether it's in-house or externalized, like you said, whether it was their team responding to comments and so forth. Should they ideally do it themselves, even though they wouldn't be as consistent, or should they have a more consistent approach, but then that would involve an external agency, say.

Um, well, I think there's a reality to when you're, whether you're again, a founder and running a small business of 10, 20, 100 people, or you're at a C-suite level inside of a big corporation. Again, we talked about minutes ago, your time is So yeah, that's why I asked.

Yeah. Yeah.

There's just, I mean, there's just a reality. You're in so many meetings. You have so much digital communication to get through. You have so many responsibilities and people that are looking up to you that need your advice or feedback. I just don't know if it's realistic to ask them to do all of that on their own. Now, there's a big difference though, and I'm sure we all can think of examples that maybe we just won't mention out loud. When someone has a team doing it and you can tell it's not their voice, you have to ask yourself, like, what, what's the point? What are we doing?

And this was going to be my question. If it's going to be authentic, then would it be really authentic if it's not done by the person? It's done on behalf of.

I think it's a, it's, I mean, the way that I work with my clients, It's certainly, it's a collaboration. It's a, both, both of us, I've got ideas and, you know, they've got ideas. There's, you know, these moments in time for the company that are really important, or there's something trending. I think you could weigh in on this. And we're sort of lobbying ideas back and forth. And then perhaps their team is sort of editing and kind of crafting the language around those ideas. And then it comes back again. It's kind of the bookends, right? You start together. Work gets done and you end together. And then they give a final blessing. Yes, that's, I like that tone. That's the way I would talk, or you hit it or not. And then it goes live and it, it's gonna feel a lot more, again, authentic and germane to that person. And then the other piece is that somebody needs to be in there again, who really is either them or knows their voice. Ideally it's them responding. To those comments, because that's where the real relationships are built in the comments.

Yeah. So in the same spirit, you would also work with AI to craft these posts, ideas, et cetera, and try and capture your voice and then have a final blessing or edit and get it live. If any founders who do not have the resources to have an external contributor or somebody on their own team to do that for them.

For sure. For sure. I mean, again, AI can be a really helpful writing partner or idea generator or even researcher. If you're like, I wanna write something and I wanna include 2 or 3 statistics that back up my hypothesis, you can get that very quickly and you wanna vet it, make sure it's accurate. But for sure, AI is a great partner to expedite that process. It's almost like the idea, again, if I think of AI as almost like a junior employee. I've heard this analogy from other people.

Mm-hmm.

Um, and maybe at some point it'll be a senior employee because it's moving so quickly.

Soon.

But in the same way that great ideas can come from lots of locations, it can come from me, it can come from my peers, it can come from something I read, it can come from my junior employees, right? Idea generation can come from lots of corners of the organization or the lab, and Also, the more that I train and invest in that junior employee to get them to understand our strategy, our goals, our vision, who I am, the better the output's going to be because now they're really tracking with me.

Okay, Jess, to your journey from a corporate employee to a business owner, looking back now, what do you understand now that you didn't when you were in the corporate world as an employee versus a business owner?

So much. I recognize that by pushing yourself to do hard things, new novel things, it is both the, um, the challenge of a lifetime. Because you're, you're pulling yourself out of a comfort zone that you know so well. But it reminds you how young we are and how much capability we have to grow and iterate and evolve. And for me, I kind of started to forget that. I started to forget that I still could. Learn and like radically learn, not just like 10%, like 70% learning curve. And I think that's over the last year and a half I've had this company, that's been such a gift. And I feel like this total renewed sense of, again, what is the next 10, 15 years of my career? I like, I'm so much more capable than I realized. I was.

And on the leadership side, Jess, what belief about leadership still makes people uncomfortable when you say it to them now?

What makes them uncomfortable?

Yeah.

I know I was talking to someone just yesterday who comes from a finance background and I, and I get it again, having worked closely with those teams all my life. There is still, it's been this way. This is, this is generations of brand builders. So I just happen to be the generation that grew up in digital, but there is still this instinct. If we're going to invest substantial money and/or substantial time, which are both scarce resources, I want to see an ROI. Like, how, how quickly am I going to get a return on this? And there's still conversations that I have to have to remind people again, just like relationships, just like dating, right? A brand, professional or personal brand, it takes time. And again, you talked about this in your blog post, you know, it takes repetition to build trust. And so it's, we're not, I mean, we're not, you're going to give me X amount of money and X amount of hours. And in the short term, we're probably not going to see radical change. But we have to stick with it.

In stuff that can be measured, such as our own.

You get the dopamine hits of the likes and the engagements and the comments. I mean, that's, that's what social is built on, right? The dopamine. So you get that, but like, that's, those are activity metrics. They're not business metrics. So where it's really going to start to shape, are you getting inbound for potential clients? Are you getting people renewing that were your clients from the past? Are you getting asked to get on stages or get on podcasts, right? Because someone's seeing what you're doing. It takes some time, but if we just go into it with a little bit of a long game in mind and know that we're investing here and it will pay off, that's probably the message that I have to reiterate to, to some, not all, but to some, because brand building is not an overnight success.

I think that's a perfect spot to end our chat today, Jess. Your brand will not be built overnight, whether it's your business one or your personal one, and you need to be consistent and continue iterating in order for it to finally have an ROI. Thank you so much, Jess, for joining us today and sharing some of your wisdom and lessons along the way.

Thank you for asking such great questions, Daniel. This is a joy.

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