How to Build a Personal Brand That Opens Doors

Doug Downs (00:08):

This is a story about how two very different people built two of the biggest personal brands in the world. Depending on your perspective, you might admire one and roll your eyes at the other. Maybe you see one as an inspiration and the other as a cautionary tale. Maybe you respect both or neither. One built an empire on empathy, storytelling, and self-improvement. The other built theirs on disruption and ambition and taking risks. One made billions by helping people feel seen the other made billions by convincing them to look beyond earth. And yet, despite their differences, despite being almost polar opposites in personality, background, and approach, both master the art of personal branding so completely that their names became more powerful than any company they ever ran. Their names Oprah Winfrey and Elon Musk. Born into poverty in Mississippi. Oprah overcame hardship through storytelling, a natural communicator.

(01:16):

She rose from local radio to national television, eventually dethroning the Phil Donahue show. But Oprah didn't just interview people. She understood them. Her authenticity built trust, and that trust became an empire. The Oprah Winfrey show, her book club, her magazine, her network. When Oprah recommended something, millions of people listened. Her brand was so strong that she outgrew any single platform even after her talk show ended. Her influence remained because Oprah was bigger than any show or company. Unlike Oprah, Musk was born into wealth, but his obsession with innovation set him apart. After co-founding PayPal, he bet his fortune on Tesla and SpaceX like Oprah. Musk didn't just run companies. He was the company. Tesla wasn't just an electric car, it was Elon's vision for the future. SpaceX wasn't just about rockets, it was about Mars. His unfiltered social media presence has made him larger than life.

(02:25):

Tesla never spent a dime on advertising. It's true. Musk's name alone fueled its rise. His tweets moved. Stock prices influenced entire industries and kept him constantly in the headlines. Even after buying Twitter, his influence wasn't tied to a single company just like Oprah. Two people opposite industries, opposite personalities, yet the same branding formula. They became bigger than their companies. They leveraged authenticity. They dominated their industries without traditional marketing, and they built empires beyond their biggest projects. Love them or hate them. You know them. That's personal branding at its highest level today on stories and strategies, personal branding. When you want to launch your career into orbit or you just want to make sure the world knows you get a brand and you get a brand, everybody gets a brand. My name is Doug Downs. My guest this week is Greg Wasserman joining today from Hollywood, California. Hey Greg, how are you?

Greg Wasserman (03:46):

I'm great, Doug. Yes, yes, yes.

Doug Downs (03:48):

And normally I would like rave about how glamorous Hollywood is, but in light of those fires. So have you been affected or is it other places like Malibu and all that? You must know people

Greg Wasserman (03:58):

That have

Doug Downs (03:59):

Been affected by the

Greg Wasserman (03:59):

Fire. I mean, everyone's been affected by the fires the city has just it's been interesting. And then I knew I was going to blank, but you connected me to who's that out in Canada that works on the fires and pr? Shout out to him. Oh, Tim Conrad. Tim Conrad. There you go. So with the fires going on, I reached out to Tim and I'm like, now I know someone that actually does this for a living.

Doug Downs (04:24):

Good power of podcasts. That was sort of through podcast discussion,

Greg Wasserman (04:29):

But it's also the power of connections,

Doug Downs (04:31):

And that's

Greg Wasserman (04:31):

Literally what we're here to talk about, right? I'll believe about is relationships. So that's the key piece.

Doug Downs (04:36):

And Greg, that's your philosophy. Your core philosophy is that life is about relationships. You never know where they may lead. You are an introduction broker. You help people and businesses turn relationships into revenue through strategic high value connections. You have a background in software as a service, digital media and podcasting. You help SaaS companies build revenue. Flywheels work with businesses to develop strategic partnerships and teach companies how to use podcasting as a growth engine. You're the person who knows a person.

Greg Wasserman (05:11):

This is true. Literally just got off the phone and the person's like, I think someone that would be able to help me and I did. And they're like, this is why we talk

Doug Downs (05:19):

Better call Wasserman. That might be a slogan. So Kate, that leads us to personal branding. So that's a form of your personal brand. You're the person that knows a person. You're the flywheel, you're the go-to. How do you define personal branding and why has personal branding become kind of mission critical in 2025?

Greg Wasserman (05:42):

I think part of it also goes to just the world we live in from a covid post covid where it's like authenticity finally became a bigger piece. We accepted the fact that we're all working from home. So that if right now your dog was to come up, you're like, this is the life I have or in my place. I'm in an apartment, someone knocks on my door and I'm in the middle of a business call. It's like, Hey, sorry, I've got to go. We kind of just accepted that. So it allowed us to truly have this vulnerable moment of like we are human. Who I show up in the office is now also who I am at home only. We're all virtual. So personal branding became a big thing because we allowed, part of it became letting the guard down. We allowed that to be seen.

(06:27):

And so for me it was an amazing thing because I'm like, that is who I've always been and now I get to be even more. But also I work in podcasting. What I love about podcasting, Doug, is you have to be vulnerable. You have to be authentic. So most of us that are in podcasting, I have to have that conversation. So if I'm not authentic, you don't want to listen. No one's going to tune into you if they're not being authentic and you're like, you're just blowing smoke or you're not giving me what I really need. Now you actually have to do that. So think this day and age is incredibly important that we have a personal brand because people are sniffing out on this doesn't smell

Doug Downs (07:08):

And

Greg Wasserman (07:08):

They move on.

Doug Downs (07:09):

And if they look just at our socials and all that, they get what we're trying to push out there. Whereas not to pull it all back to podcasting and maybe YouTube as well, but there are deeper layers. It's hard to fake yourself for 30 minutes in a podcast. At some point, the real you is going to come out

Greg Wasserman (07:27):

Or you would hope the person that's asking the question is able to pull that out. Yeah, but it's also you want to, we're in the state now where you want to work with people and trust, and it comes back to relationships. We as a human, we need connection that we crave that. I had a conversation with someone about ai. It's like the end of the day, what I do from a human connection standpoint and what I do from a broker standpoint, AI's not going to be able to do that. I've seen companies that are trying to do that, but at the end of the day, if you introduce me to Tim, that's going to be so much more than how is Tim and I ever going to get connected by an AI chat or whatever the case may be. It's all from a human connection standpoint.

Doug Downs (08:17):

So when I think of personal brands, of course Taylor Swift comes to mind, Oprah these days. I think of Donald Trump. I think he won two elections in large part based on a personal brand that he's built. I don't know if Kanye's done it quite as while his brand is out there. I'm not sure if you'd call that effective or not at the moment, depends on who you are. But that's another layer. Those are the PGA golfers of the personal branding world. They're up there. There are millions and millions and billions and billions of dollars, but there are other layers of personal branding. Who comes to mind when I say who's done it well to you?

Greg Wasserman (08:59):

Can you name, I know you're Canada, but can you name three automaker CEOs,

Doug Downs (09:07):

Automakers? I should. Oh, I should. I should know General Motors. I sorry, top of mind. I can't, but you know exactly one Howard Schultz is Howard Schultz one of

Greg Wasserman (09:18):

Them? No, that's Starbucks.

Doug Downs (09:20):

Shoot.

Greg Wasserman (09:20):

Okay, sorry. But one Elon Musk and Tesla.

Doug Downs (09:27):

Oh, for God's sakes. Absolutely. Right. So if I

Greg Wasserman (09:30):

Say, Hey, I didn't even think that he owned a car company. That's how silly that is. But just personal branding. People buy the stock price is going up or it's gone down depending on where he is now in his landscape. But the stock price is literally tied to him being out there, as you said, Donald Trump one presidency because of who he is. So it's incredibly important. I think about, and I knew I was going to blank on this, but T-Mobile is a telecom company. They have all their commercials, but the biggest outspoken person was their CEO until he stepped aside. And so the new CEO is nowhere near as out there as he was, but he was the disruptive brand. He emulated the brand. So then if we think about it from a personal standpoint, and you mentioned Taylor Swift or Elon Musk, me and who I am and an employee, it's like people don't trust companies anymore. We don't trust the news anymore.

(10:35):

So it goes back to this authenticity of who do we trust? Well, I trust you. I know you. I see the brand you're putting out there. And that's why we're having such a rise in influencers and people are like, great, I'm going to buy products from these people. I feel like I know 'em because they're authentic or realize they're just pushing a product or they're just getting paid for it. Like Kim Kardashian, Kim Kardashian literally grew our entire brand. And then it would be like, I have a hundred million people on Instagram. I don't know what a number is. It's going to cost you a million dollars to do a sponsored post. It's like, all right, well probably whatever she's selling in that regard, she's getting paid handsomely for it.

Doug Downs (11:17):

You mentioned the word influencer. So what if I'm someone who suffers huge pangs of imposter syndrome at key moments, and I'm realizing thanks to people like you that I do need to put my personal brand out there. I mean, the artwork for this podcast doesn't have my face on it, and I got to start thinking about stuff like that, and it's because I have imposter syndrome. Could I still enhance my personal brand without necessarily wanting to be an influencer? Or should I overcome my fears of what influencer really means?

Greg Wasserman (11:54):

Well, I guess that's the question. What is an influencer, someone who influenced? So we go back to just the old radio days. They were the original influencers, a radio personality talking about a brand. No one had any other ways to get media, and that's where you got it. And that started and then turned into tv. And now it's of course turned into all these other avenues that you can be an influencer. But an influencer is, I'm just being authentically me with an opinion and talking about things that matter to me. And it goes to communion relationships. You're going to vibe with what that person has to say. And so their influence continues to increase because you're like, Ooh, more people like what you have to say, the way you say it, the way you act, what you're doing, the information you're sharing. So you're just authentically yourself.

(12:48):

It's the bare minimum people will gravitate to you. That just started about it from a friend circle. Just think about it from that. Why do people I'm friends with like me, okay, that alone is you have a sphere of influence with not only your family but your friends. Now it just expands beyond that from a work standpoint. But the more you talk about who I am, what I believe in, you're going to alien me. Let's go to Joe Rogan, another example of a person he knows who he is. You ask who's Joe? Joe Rogan's audience, you can tell it's polarized. He doesn't care if someone like me isn't going to listen to Joe Rogan or someone like you. And he's like, great, I know who my people are. I'm content with knowing my people. Or you're going to have the politician. I've got to shake both hands. I got to make sure I'm careful on what I say. It's like I'm back to Trump. He doesn't care. I'm going to polarize people, but I got to bring 'em together. But at the end of the day, I can win an election because I was able to get enough people that wanted what I had to say, and then the rest of you, now you're going to have to live with it. And that is, it's a different situation from a country or country standpoint, but it's ultimately most people's philosophy.

Doug Downs (14:05):

So let me push you a bit deeper on the authenticity piece here. I got you keeping it real. Kendall Brightman from Riverside coined this phrase, so it's not mine. And we were talking about as a male, this might come across as sexist, but as a male, I can literally throw on a ball cap having a bad hair life day and go on YouTube and record a video. And I'm relatively, I'm not sure most women feel the same way. I would suggest most women feel they need to put themselves together, whether they do or don't. I think that's how they feel. And she agreed and said, I think for women, authenticity is about being authentically put together. And I love that phrase in that case had to do with how you visually present yourself. But does it apply the same way to how I just plain old present myself? Am I really dug downs or am I this put together version of dug downs? Are you really Greg Wasserman or are you some version that's face a Greg Wasserman? And is that the whole key to being authentic?

Greg Wasserman (15:15):

It's a valid, it's a good one. Kendall, part of it I think would be what is it that you want to share? Right? I've seen it plenty of times. The put together a person on Instagram also has some posts, or I'm just in my sweatpants day, right? This is just me. So there are those moments where this is the 90% version of myself that I'm showing you, but you also get to see the 10% of you know what, it's a ball cap kind of day. And that's okay. But I think it also comes down to the individual we've seen in this day and age because of, I believe Covid, okay, that if I want it, I put on this shirt, Farley Valentine's Day, and I've got plans later, but I put on this shirt so that I could be presentable for this podcast.

Doug Downs (16:18):

Your shirt is a red shirt

Greg Wasserman (16:20):

With a

Doug Downs (16:20):

V-neck. Just focus on the audio.

Greg Wasserman (16:22):

So normally I'm in a shirt and a hoodie, I'm in a t-shirt hoodie. I've got my blue ggl glasses on. But for the sake of this podcast recording, I'm different presentable. But that doesn't mean that if you want to, most of the content that I'm putting out, you're not going to see a version of that as well as a version of Greg and t-shirt and jeans, right? So it's a matter of who I want to present, but they're both me. I'm business and I'm relaxed. That is authentically me.

Doug Downs (16:58):

So what if I'm just a public relations professional? I'm a couple years out of school and an advisor somewhere. Do I need a personal brand? Do I need to start working on this? I think you're going to tell me yes. So tell me how do I go about doing that?

Greg Wasserman (17:14):

Just start. I remember during Covid, there was a community that I got introduced to, and they were all teachers, or I should say those that worked in education that want to get out of education. So administrators, teachers, whatever. And none of them had a LinkedIn profile. They had a LinkedIn. They created LinkedIn, and this was all over LinkedIn, but none of 'em were thinking about connections. I'm a teacher, why do I have to have LinkedIn in order to connect other teachers, to connect with other administrators? LinkedIn is never going to be the meeting for that. It goes back to my philosophy, life is about time and relationships.

(17:58):

If you don't have a crystal ball that you think that you're going to be an educator for the rest of your life and that's what you think of, well, you don't know if that's going to change. You don't know what's going to happen. So might as well start building that muscle, building that brand. It's the answer. I'm a few years out of college and looking to do this. Go ahead and create a profile, start filling it in. The way I would say is, at least the way I was taught is put your jobs in there and craft a story. Why did you choose this company? What did you accomplish there and why did you leave? That is a standard thing. But you see other people put in bullet points, I did this, this, this, and this, and it's more like a resume. I went down, lemme tell you a story in what I've done. Neither way can go wrong if you're just starting out, but at least put some information there. People want to work with people they know and trust. And if I go to your profile and there's literally nothing there, who is this ghost?

Doug Downs (18:58):

There is this thing I read a while back about social media and that posting a comment on Twitter or X or whatever is going to a party saying something out loud and hoping somebody says, oh yeah, I like that. And I've never lost the feeling of that, that I might say something and nobody cares, nobody gives a dang. But what you're telling me is just do it and find your rhythm. First off,

Greg Wasserman (19:23):

Consistency, but second, great. That's a great thing about engagement. I think my posts today, no one cared about it. I'm like, all right, either I wrote it wrong, I missed the mark. But at the end of the day, if you go to my profile, and since I consistently poke every day, you'll actually get an idea of who is Greg? I do not only the profile I get, but also the content I'm putting out there. So if I go to your profile and there's nothing there and there's no engagement, I say this to people, I'm like, it tells you, LinkedIn tells you Doug liked something. Doug commented on something or Doug posted something. And if there's nothing, then Doug is not only just a lurker, what is he doing here? So who is this Doug person? And I work in revenue. So for me, it's in sales.

(20:17):

So if I'm sending you an email, most people are going to go to LinkedIn going, who's this person that's reaching out to me? And if your profile has nothing in that regards and they don't have an idea of what you stand for, what you're trying to sell, whatever there may be split decision, they're already going. Like, do I want to take this call? Do I trust this person? So if you are PR person, you are trying to find a job, LinkedIn's probably your best place. Networking relationships. If I try to reach out to someone going like, Hey, I would love to get a job, and they go to your profile and there's nothing there, why do they want to take a call from you? They probably think you're trying to sell 'em on something. So optics matter in that

Doug Downs (20:58):

Regards. Great seeing you today, Greg. Really appreciate your time, man.

Greg Wasserman (21:02):

Likewise, Doug. Appreciate having me on here and talking about this.

Doug Downs (21:07):

Oh, hey, in our previous episode, Greg, our guest, Michelle Garrett, she left a question behind for you.

Michelle Garrett (21:13):

Here's my question. So as we are trying to balance our need to follow the news with our mental health, what are some of the ways that you do that? That would be my question.

Greg Wasserman (21:28):

So I don't watch the news

Doug Downs (21:30):

Good for you.

Greg Wasserman (21:32):

but the only news I do watch is CNBC. So the financial news, and that has always been something I've believed in because numbers, well, it's not just numbers, but it's like I'm investing in the market. And if you can follow what companies are doing, that is news in itself. It's like, well, what companies are talking about from tariffs that are going on right now? Well, I don't have to follow what news channels are talking about. I'm hearing about it directly from companies, which will affect you and I in our bottom line of our purchasing power, our insights to what can I actually accomplish? What should I be buying, what should I be thinking about? I don't need to go watch the news and say, Hey, the price of eggs are $12 right now because of a bird flu. I'm like, Hey, the stock is down because of the bird flu.

(22:24):

And so I'm getting the news from that way, but balancing mental health in that regards. I don't watch mainstream media. I get it from other mediums because as I tell my mother who sits there watching of a certain age, so every night, 10 o'clock news, I'm like, mom, you come to me worried every day about what you've watched. Yeah, my wife's like that. Yeah, the news literally is there to sell fear because that's what sells advertising and ratings. That is what the news does. So if you are now watching something that is going to elicit fear and anxiety, you're already an anxiety ridden lady. This is not healthy. So if you're going to come to me and say, Hey, Greg, I'm worried about this. I always tell my mom, I'm like, great. Give me one positive news story. And if you can't give me a positive news story, I don't want to hear what the worry that you have, but the news is feeding you because that is where we are. We don't trust the news anymore. We trust people. So I balance my mental health by realizing the business of the news, the business of other people's agendas. And I try my best to also get new sources beyond what I would normally consume. And that's big piece. Someone turned me onto a podcast that is very different ideology than I would follow, but I am learning so much. I'm like, great. I'm not only learning what they're talking about, but it's newsworthy without an agenda of selling advertising.

Doug Downs (24:05):

And I mean, not so much with podcasts, but conversations I've had with people where I know I disagree with them from the onset. If I'm in a genuinely open mood, I typically come out of that conversation with very genuine empathy and better understanding of why they think the way they think. I may not agree still, but it becomes way more complicated than I thought. So I agree with that. Your turn, Greg, what question would you like to leave behind for our next guest?

Greg Wasserman (24:35):

We're seeing it harder and harder as media institutions. They've evolved. Journalists are fewer. So from a PR perspective, where do you see earned media versus paid media evolving in the next few years? Appreciate it. Thanks so much

Doug Downs (24:58):

For this, Greg.

Greg Wasserman (24:59):

Likewise, Doug.

Doug Downs (25:01):

Here are the top three things I got from Greg in this episode. Number one, authenticity is non-negotiable Post covid. People expect authenticity in personal branding. If you aren't genuine, audiences are going to move on quickly. Number two, people buy into people, not companies. Trust in institutions is declining. So personal brands matter more than ever. People engage with individuals they know they like, they trust. And number three, consistency wins the game. Building a brand isn't just about posting and engaging with others through comments and conversations keeps you top of mind. If you'd like to send a message to my guest, Greg Wasserman, we've got his contact info in the show notes, stories and Strategies is a co-production of JGR Communications and Stories and Strategies podcast. If you like this episode, could I ask you to do me a favor? Go into your podcast app and leave a five star rating. And if you can, maybe a short review. Those are huge to helping podcasts grow. Thank you to our producer, Emily Page, who's a huge help every week. And lastly, do us a favor forward this episode to one friend. Thanks for listening.