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Feb. 17, 2021

Hillary Weiss | Turning Brazen Ideas into Clear Concepts that Captivate the World

Hillary Weiss | Turning Brazen Ideas into Clear Concepts that Captivate the World

We return for another episode, this time with Hillary Weiss, a creative director, coach and speaker. Hillary tells us how we can take brazen ideas and use them to captivate our audience. Learn about anti and advocate standpoints, how to be shamelessly ...

We return for another episode, this time with Hillary Weiss, a creative director, coach and speaker. Hillary tells us how we can take brazen ideas and use them to captivate our audience. Learn about anti and advocate standpoints, how to be shamelessly polarizing and much more.

 

Visit Hillary's website | https://hillaryweiss.com

 

Follow Hillary on Instagram | https://instagram.com/hcweiss

 

Follow Hillary on Twitter | https://twitter.com/hcweiss

 

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Transcript

Srini Rao: Hillary, welcome to the unmistakable creative. Thanks so much for taking the time to join us. Thank

Hillary Weiss: you so much for having me. I'm so excited to be here.

Srini Rao: Yeah, it is my pleasure to have you here. So as I was mentioning before we hit record, you are in a long line of people that Sarah Peck has referred all who have been absolutely stellar.

So no pressure at all. But the first question I want to start by asking is what social group were you a part of in high school and what impact did that end up having on the choices that you've made throughout your life and your career?

Hillary Weiss: Oh, my God. Yes. So I've actually been I was lucky and unlucky. So I grew up in suburban South Florida, and I actually went to the same school for 14 years.

So kindergarten all the way through 12th grade. And what happens when you go to the same school for 14 years is that everybody remembers like who peed their pants in pre K and who did the embarrassing thing in second grade. So I actually I wasn't I was in one of those social groups that wasn't I was not popular.

I was also not in the total reject spot. I was in this satellite group and we were friends actually for the full kind of 14 years and just orbited around doing our own thing. And what's actually been really cool is a number of the people from my high school life I'm actually still really good friends with.

Like I have a group of girls who I go travel with back when we could do that. I would travel with every year. And everyone's married and like having kids now, so it's a little different, but it's actually been an incredible source of value in my life to have those consistent friends who've known you since you were like too awkward to put a sentence together, who saw you through your emo phase, who saw you through your punk rock phase and watched you just turn into a pretty standard issue professional white woman down the line.

But I think that one of the biggest surprises from my high school's career, and I'm actually really proud of this. was in my senior superlatives in my senior year yearbook. I actually won class clown, much to my surprise, because I didn't talk to most of my class, but I did make funny comments with my English teacher.

Apparently this is what I was told. So winning class clown made me feel way more relevant than I actually was, but I'll take it. Yeah. I wonder how you, that affects the depth of the friendships you have, because I I'm putting together a tribute video for my sister, Andrew Horn has this company called tribute, which is like Hallmark 2.

Srini Rao: 0, where people just send in videos and her birthday's coming up. And yeah, My sister and I had very radically different upbringings because I moved around constantly because my dad was still building his career. He hadn't gotten his tenure track position, but she had a lot of the same friends in 6th grade and the people that I've known for 20 years were most of my close friends are the ones I went to college with.

So I don't have any of these lifelong friendships and something I've always envied about my sister's friends. And she said by the way we're an anomaly. She's this isn't all high school people. Somehow they've that group for some reason was very tight and they all have stayed very close.

Like they have a WhatsApp group, but What is it, you think, in adult life that allows people to maintain the depth of friendships like the ones you have and how do they do that if they didn't get to go to the same school for

Hillary Weiss: 14 years? That's such a great question. I think for us, it is a, for the girl gang that I hang out with that I've known forever, I think for us, there's a certain desire to maintain that connection to who we were, because in the case of a few of my friends, they have really exceptional careers.

One of my one of my dear friends, Kelly Girardi, who you can find on Instagram and TikTok is a spokesperson for the future of space flight. And then Maggie Spicer, yeah, she's amazing. She's actually worth interviewing on the show.

Srini Rao: But that was my thought. I was like,

Hillary Weiss: she's incredible.

And then another dear friend of mine is her name is Maggie Spicer. She is, she works for a power law firm in DC, international trade law. Our other friend, my other friend, Kat Cassidy, she's getting her PhD at St. Andrews in Scotland in computer science. So we all split across the world and really got deeply focused on our careers.

And then I started a business, I'm right out of college. So it was it took off for me as well. So I think a big part of it is Hey, we're out in the world, but It's sometimes maybe harder to make friends as an adult when you're so focused on your career as well. I'm really lucky that I have a bunch of friends here in New York City, but it's also partly because I had some great friends in college who also all moved up here at the same time.

So I think it's that desire to Stay connected to those people deliberately. Those people who remember who you were before you were so busy and important. But I think my siblings also don't really have a connection to people in high and from high school or grade school. I remember my sister, bless her, I have an older sister who's about four years older than me, who actually sat me down before I graduated col before I graduated high school and was like, I want you to know that you're probably never gonna talk to your high school friends again.

And I was like, she also ruined Santa Claus for me in a similar way. But she... I was like, oh no, we all love each other, we're gonna stay in touch, and certainly some people did fall off they had other interests, we got into disagreements and they faded away, but these girls, what I think is so special about it is that we all have that, we share the desire to stay connected, and I think unless everybody's in it's really hard to be one person on the other side of the phone trying to stay in touch.

But I think, and I think that it's actually natural to let some of your friendships fall away. I don't think it's a bad thing not to have friends from high school. I think it's an unusual thing that I do. But there just has to be that desire. And we're really lucky that all of us are that four point star able to keep connected across miles and years.

Yeah. We had Lydia Denworth here who wrote a book on the psychology of friendship and she was saying that basically a lot of things happen circumstantially people move away and proximity plays a big role in all this. What's changed about these friendships over the course of your life?

Oh man. So this is, what's interesting is I won't say who, because I've already dropped off their names, and I don't think they'd want me to find out. They'd want it, they'd want they'd want people to know. But a couple of my friends there were ebbs and flows in the friendship, I think. Let's say, high school, we were good friends.

College, we felt a little bit out of touch. And then after... We all reconnected enthusiastically. But I think, and I think of course in high school, there's all the disagreements about boys and all those things happen. Oh yeah. Oh God, I could tell you stories. But I think that what has, how, what has changed has been probably The amount of energy we also require from each other, which is interesting, and I think another really important thing about adult friendships, actually, is there's, especially in the digital age, a belief that you always have to be connected, always answer the text, don't ghost on the group chat, quote, unquote, people need space, like not to reply to deal with what's in their lives and have a place to come back to, like a friend group to come back to.

And some people don't like that. Some people aren't into you. If I don't respond to the group chat for a month, then I come back being like, some crazy stuff happened, some people are going to be mad but you have, there's that sort of mutual symbiosis of understanding that we have lives, we love each other, and just because we're not replying to every single text right away, doesn't mean that friendship and that love isn't there, and I think we have that unspoken agreement that's so important to maintain those kind of friendships long term.

Srini Rao: So do your high school days predate sort of social media, the digital tools that we have today? Yes and

Hillary Weiss: no. So I I graduated high school in 2007. So it was it was my junior year of high school was when Facebook was big and I was on LiveJournal and MySpace before that. That was chaos.

That was like the Wild West of the social media era. I don't know how much you remember her, how active you were. Keep in mind I'm a bit older than you. So I graduated high school 1996, which is why I asked the question. Cause I always wonder how that would impact the depth of friendships.

Srini Rao: Like I had a college experience with no Facebook and I think there are pros and cons to that. The con being that, Oh, if I met some cute girl at a party, now I could go and look her up on Facebook and actually go contact her. In college, I could never do that. It was like, Oh, that was a drunken night and I'm never going to see her again.

Hillary Weiss: Yes. I think about that a lot, actually. I was thinking about that in the context of. Is it the ability to disappear has vanished in the last 20 years. Because people can find you for a reason. Yeah, exactly! People can find

Srini Rao: you from anywhere. Yeah, that's I have no privacy anymore. I

Hillary Weiss: wasn't gonna ask, but I was curious, but I think what was interesting is I experienced the really early form of cyberbullying when I had LiveJournal in my freshman year of high school.

I had some mean girls hack into my email account and all these things. So all this crazy stuff was happening, but it was so early, it didn't really have a name. So we had to figure out how to deal with it and I think one of the crazy things about having social media in college aside from you know being able to find someone at a party that you made out with and never tried to never speak to again and then Gave it a shot and y'all realized you had nothing in common.

I think the gossip stream was so powerful in college as well because of social media and I don't know if anyone's Anyone here is going to relate to this, but when I was in college, the one of the craziest things wasn't actually necessarily social media, it was a platform called Juicy Campus, where gossip from the basically college campus life was posted forum style for everybody else to read.

Oh, yeah. And then, and it was, I think the site was shut down because That was I just remember that was so interesting to me, I was like, is this social media getting out of control? But what my familiarity with it also allowed me to build a business via social media and the internet, basically as soon as I got out of college, so I gotta give props where props are due.

Srini Rao: It's funny because that kind of thing probably wouldn't have done so well because I went to a college with 40, 000 undergrads, Berkeley just had such a massive student body. Okay, cool. So you have these friends who sound like they're movers and shakers. I wonder what impact they've had on your own thinking about success and how your own behavior has been affected by the people that you've surrounded yourself with.

Hillary Weiss: It's so interesting. I what was interesting about me when I graduated. So I graduated college in 2011. And I had a similar story from what I've heard about you when you graduated business school in 09. And it was what now? There's an economic recession, jobs aren't really available, so what do I do?

And I was the first one to, I think, jump headfirst into a kind of more unusual career from that friend group, and I had all their support. But what was interesting is that no one really believed I could do it. This group of girls, of course, did, because they know me and they know I can make anything work.

But it was interesting to know that I was inspiring them through just stepping into the fray and taking swings, because I had to. I graduated. 2011 with a communications degree from the University of Miami. There are public relations was my major. There were no public relations job worth anything really at the time.

So I had to jump into copywriting and maybe starting my business and making that work. But what was interesting is that like Kelly, for example, who's the influencer, by the way, we were a subject of a viral tick tock on her dick doc, all of our little friend groups. So I can send you a link to that if you're curious.

Yes, absolutely. Absolutely. But she. Was so her and I would talk because she was still trying to figure out her career She was trying a bunch of different things. She worked in the diamond industry for a little while she worked in she was, you know working her way towards Working in the sciences, but she actually has a film degree, which is really influenced.

Interesting. She has a book called not necessarily rocket science which is about the fact that she has a film degree and is basically a citizen scientist. And so her and I would talk and she was like I really want to do something on my own. As well. And how are you doing it? Can I? And her question was, can I get paid to just be awesome?

And I was like, actually, yeah, you technically can. You just have to figure out a way like a message that you really want to share something that you're really passionate about and step on the gas. And for her, that was aerospace. And in terms of how the rest of the group has inspired me as well through their pursuit of their careers, I think it's just been that nobody really hesitated.

It. Everybody saw what they wanted and were able to go after it, and especially in Maggie's case, who's the power lawyer, she was always going to be a lawyer, always had her sights set on what she wanted. Kat always wanted to go to St. Andrews whatever she was, whatever her focus was going to be was up in the air.

But it was really cool to have a group of women in my life who were able to see the end goal and pursue it without apology. And I think that's a really a perk of this, of our generation as well, where there are less, certainly less barriers than there would have been even, 30 years ago.

Srini Rao: Yeah. So one thing I wonder is you've mentioned your sister went to Berkeley. You've got all these friends who for them, based on some of what you've told me about them have pretty clear trajectories in terms of the steps to follow to get to where they want to go. Like becoming a lawyer is pretty obvious.

You go to law school becoming a doctor, it's Oh major in science, get good grades. So I, one, I'm curious what kind of advice your parents gave you about making your way in the world and then to. When you're a sort of the oddball person who decides to go do something where there isn't a clear path, how one what's useful about that you can draw from clear trajectories.

And then how do you combine those two things into what you do?

Hillary Weiss: Oh God. I love this question because it's complicated, so I might ask you to give it to me again. I will. If we're asking, if we're asking about what my parents thought I was out of my mind. They were like oh dear honey, we love you so much, but I don't know if this is going to work.

Because the job that I do basically didn't exist even it had only been around for maybe five years, like having this type of copywriting, the type of copywriting that I did. In the online business space, because the online business space, especially the industry I worked in I got my start in like the coaching and creative sphere.

It was so new and it was just like this budding little flower. And so I told my parents, so I graduated U Miami and I actually managed to land a job at a PR firm in Miami. And I was, I worked there for free as an intern for three months for the privilege of being paid 8 an hour. While I was working on my copywriting business and I remember I actually got fired for obvious reasons because I would sit and write really crappy pitches and then work on my business during work hours, which wasn't the most professional thing of me to do.

So I got laid off and I was still in Miami at the time and I remember calling my parents and I was like, I think I'm just going to do it. I think I'm going to go hard in the paint with my copywriting business and I'm going to make this happen. And they were like, Oh no. We're not going to help you financially, so make your way.

But then they thought I was even crazier for moving up to New York City a year later. Because it wasn't that they were they didn't believe in, it wasn't that they didn't believe in me necessarily but I think that they were just, they It had never occurred to them that it would be a possibility to pursue a career like this.

And also that I had very little experience with running a business. I was an intern a million times over, but I think they, it's often expected that you have a little agency experience or a little formal experience before you go out in the world. And I didn't have time for that. I just go, went ahead and found my way.

And the nature of my personality is very much I'm going to do what I want to do and I'm going to figure it out. It's just, it's a core component of who I am. So I think they in some ways trusted that I would figure it out. I didn't think they would thought I would be as successful as quickly as I was.

But it was the Miami getting laid off. They were like, Oh, I don't know about this. And then when I decided to move to New York a year later, they were like. Okay, why are you doing this? The taxes are so high. It's so cold. What are you going to do? By the way, you should probably just try to get a job when you're there.

So you can work on this on the side, but try to get a job at an agency. And I just refused because it wasn't going to pay me as much as I was making in my business already at that point. And I wanted to do my own thing. I enjoyed it. I enjoyed the challenge of figuring it out. And it was a time before you could throw a rock and hit a six steps to six figures business program.

It was before that wave of online courses teaching you how to make money online as a service provider. But I feel really lucky that I was there before all of that happened because it allowed me. To build up my muscle memory for trying things and experimenting and really, as you and I were talking about a couple of days ago, throwing those Hail Marys being like, I think I want to do this.

I don't know anyone who's done this, but I think these are the steps. Let me give it a shot. And 9 times out of 10, I've been really blessed to be successful in those ventures. So I think that overall. My parents disbelief in me was mostly because they just weren't sure what was gonna happen. They'd never heard of it.

It wasn't familiar to them. So I really had to make my way despite a lot of people trying to dissuade me. People who were also not just my family, but my friends too. They're like, I know some freelance writers and they're all broke. And I just don't know if you can do it. So anyway, but that's the nature of who I am as a person.

It's also the nature of my Zodiac sign. I'm a Taurus. So I will just barrel through anything like a bull in a china shop. But now I'm wondering what the second half of that question is because I've completely forgotten in

Srini Rao: my range. I think it's what are the useful parts of the linear trajectory that come into this?

Because I think the other day I was, I think I asked a question on Facebook, I said what do you think are the benefits of being raised by Indian parents? Because I said like for the longest time okay, they give you all this conventional wisdom of, oh follow this path, go to school, get a job.

But I realized outside of that, there was some really intangible skills that came from being raised by the parents I had. I think the biggest one being intrinsic motivation. It's that story that every Indian kid has. You go to school, you find out some white kid at school gets five dollars for every day.

You come home and tell your dad that. And he's that's great. You get a meal on the table and a roof over your head. So this negotiation is over. And that was invaluable. Even though it like everything that I thought was a pain in the ass about my parents when I was growing up has been incredibly invaluable later in life because they taught you work ethic, they taught you the value of education, they taught you the value of doing something without the expectation of a result.

But that being said, I think that one thing that happens when we hear a story like yours is confirmation bias kicks in, right? And I've been really pushing this idea of people not considering context when they look at the success stories of people and assuming that Hey, if I do exactly that, I'll get that result, which has been my core messages.

No, that's not true. And I think that this is something that is been detrimental in the online world where you have a lot of people basically using platitudes as life plans,

Hillary Weiss: which is never. And that honestly leads to more bad outcomes. It's people follow their passion faster to poverty than they do to profit more often.

Srini Rao: And and then that's harsh to say, but I think that we don't really talk about that because it's not what people want to hear. And I'm curious what you have to say about that, because I think that in a lot of ways, you're an outlier. I think for every single person that achieves what you do, having done what you've done, there are plenty who don't Reid Hoffman has that saying the building a startup is like jumping out of an airplane and building a parachute on the way down.

And I was like that's great. If Reid Hoffman is the investor in your business, if not, you're going to plummet to your death. There's no parachute. Yeah. Yeah. So I'm just curious what your thought is on sort of these subtle nuances that get completely overlooked. Hell, you're a copywriter.

Your job is to convince people to do things because I see this come I'll give you the example that I always come back to. Somebody says, Oh, everybody should start a podcast. I'm like, no, that's horrible advice. Not every, there's nothing that everybody should do. Yeah,

Hillary Weiss: I think that so first of all, I'm actually I retired from copywriting last year.

I'm a creative director and positioning coach at this juncture, but I was a copywriter for 10 years. And yeah, but learn a lot about persuasion in that category. But it's so funny that you talk about. Your parents as well and the way you were raised because I was raised by an old school boomer wasp family Which is similar principles to exactly what you've described actually my best friend is Indian and we relate on this a lot Where it's oh you got an a that's exactly what you're supposed to do.

Why do you think exactly? Why are you on some kind of reward good job? No, you're not getting in 20 to go see a movie with your friends. We put a roof over your head. We pay for your education. We put clothes on your back and food on the table. What more do you actually need? Get a job. And I did. I got a job from a very early age.

And I think that, and it was the millennial generations the quote unquote snowflake, the participation trophies, my parents were really against that culture and that shift in culture. So like my mom would constantly tell me the world does not care about you.

We care about you, but the world does not care about you at all. So you have to be. focused, you have to be good, you have to work hard for anything that you have and the importance of education and all these things that you've described. And what was really interesting to me actually, so when I got my start, like just reflecting on this whole journey, it's been 10 years now.

When I got my start in copywriting, I was 21, 22 years old, and I knew I was the odd one out. I was one of the youngest people in my industry. I would hide my age a lot. People would be like, how old are you? And I'd be like, I'm 20. And I was like, I was excited to turn 30 for a decade because I was like, at last people will take me seriously, but I got into the industry and I realized that I'm not the smartest.

I'm I don't know the most. I'm not the most strategic. I'm not the most experienced, but I will outwork any of anybody else. I will outwork any of my competitors. And that's what I did. And that was my ethos. Anything a client threw at me. I. I slammed all my deadlines. I would research the hell out of anything if I didn't know how to do it and also be honest with my clients about it and make it work.

And I worked and I worked and I actually, it got me really far. Like I think I had my first six figure year when I was like 25 or something in my business. But what was also happening with that amount of work was that it also totally fried me. I worked seven days a week, six days a week proudly.

I was like, I'm doing it. This is the kind of work that it takes. And then of course you hit a tipping point where you burn out and you look behind you and you're like we'll wait a minute. Maybe I don't actually have to work this hard. So rethinking that approach and that Protestant work ethic, quote unquote, has been an interesting part of my story the last few years, but I think about this so often, and I'm so glad you brought it up, because I think that if there's so much danger in telling my story and being like, I did it, you can do it too, because there's such a large range of factors that come into.

Create you as a person, as a creative, as an entrepreneur about your work ethic, about your ability to perform, about your integrity so much of how we're raised and also the resources that we come with, because I was raised with a lot of privilege and I realized this, of course in the last few years, unpacking all of that, what was, and so I was never really in a position where If everything went belly up, then I was destitute and I would have had to go to a shelter.

There was always the opportunity that if everything went belly up, I could go home. And my parents would feed me, put a roof over my head, there was always that opportunity, so while of course I don't want to totally... Take away the the story of people who are in my position because it did it take a lot of hard work and courage and testing and awkwardness and embarrassment and sudden breakthroughs?

Hell yeah, it did. But also, I think it's so important for us to recognize where we come from and what our privilege and the way we were raised has allowed us. to do and the risks it's allowed us to take. And I talked to my clients about this. So I do positioning coaching where I work with business owners to really define their position in the market so they can create their content around it, their offers, all of these really amazing things.

But I'm also really always listening to what they're coming to me with. And I refuse to tell a lot of my clients like, Oh, that's just mindset. I think that there's so much dangerous about that attitude. Because people are coming as the sum of their own experiences and the way they were raised. And also, if they lack that level of security, if there's no home to go to, if there's if they, maybe they're short on savings right now and really trying to make it work, you have to be conscientious and having that attitude that like I can do it.

You can do it too. Gary V tells you, you can't. There's just going to be so much, it's going to be so much harder than if you were to sit down and actually recognize what's going on, what's the context and then building from there. So I think it's really important as entrepreneurs and people with these stories to look at, all right, where do we come from and what allowed us to have this ability to be courageous and take these risks.

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Srini Rao: cure, or prevent any disease. Yeah I think, no doubt I'm in a similar position, son of a college professor. My parents let me live at home for eight years while I was doing this.

Oh, they want to kick me out

Hillary Weiss: after eight years. Into my late thirties, it was yeah, I think there was a point at which they were like, okay, we're, I think it was right around 2015. I remember when I moved back home a second time, my business partner at the time said, just tell them that if you don't get it together within a year, you'll start looking for a job.

Srini Rao: He's cause. They just need to hear that. He said, they'll leave you alone for a year. And I think two months later I got my book deal. So I think after that, they're like, nevermind, this is serious. But no I appreciate the candor here because I think that there is a real danger in the message of, Oh, anybody can do anything.

And then you get people spending money on these 10, 000 coaching programs, believing. A bunch of bullshit and ending up in situations they really can't get themselves out of. I think I think I put a piece yesterday on Facebook saying don't ever make a major life decision based on a peak experience.

And so often that is what ends up happening in these situations. Why

Hillary Weiss: burning man ruins lives.

Srini Rao: Trust me, the amount of stuff I have to say about new age, bullshit would piss off so many people. It's ridiculous. Let's do this. I want to shift gears and I want to start talking about what I had mentioned to you that I caught my attention on your website, which was this idea of turning brazen ideas into practical concepts that captivate the world.

Cause that just got me right away. I was like, Oh wow, there has, and I'm a weirdo who always wants mental models for things. So I'm guessing there has to be some semblance of a mental model for how that happens.

Hillary Weiss: Yep. So I, there's a couple it's. All right. There's a couple things I have to say about this.

So first of all, I think that a lot of what I do in creative direction and positioning is in my positioning work is taking entrepreneurs and creatives through the process of self reflection deep enough that they can realize not just What they do so well, but why and what sort of from their life, from their value system, from everything they have done and seen in their life, what they're bringing to the table that makes their point of view so unique, because there's that saying, right?

Your business is what you do. Your brand is who you are. So when it comes to these brazen ideas, these captivating concepts what I do, and I talk about it like an elevator, so you have in the branding world the kind of standard response. Let's say we're talking to They're running the mill business coach.

Like I help my, Oh, sorry. I hope my clients align with their values and create really cool stuff and find their voice and show up more online. And that's great. And a lot of business coaches are going to say that and they're going to talk about that. They're going to make the six figure statements, but I what I really want to do is help my clients take the elevator when I say one floor down.

So it's okay, you want to do this for help these clients find their voice and create more stuff online. But why is that? Why is it so important to you? What are you coming to the table with that you do so uniquely well that nobody else does and how do we build from that? And so when I talk about brazen ideas that turn into concepts that captivate the planet, I really help them dig under the layers to figure out what is so exceptional about them.

And part of that journey. Is not just exploring what they do for who, how, and why, but also what do they love about their industry and what do they hate about it? What are they counteracting with their work that they believe in or don't believe in? What do, what is something that a client says to them that they're like Oh God, if I never hear that advice ever again in my life, it will be way too soon.

And similarly, what are they nerding out about? So forcing them to examine what is the core idea that's informing everything that they do. And part of how we do that is, of course, we talk about these, we talk about what they do, what their specialty is and their audience and all of those typical things.

But we also talk about the framework and I actually walk them through. an exercise where it's let's say you're a copywriter and you take your clients through a series of steps, right? But what are those steps? And most importantly, why are you doing them? Because often when you're at a point where you're ready to do creative direction, rebrand positioning work, you know that there's something you do so well that no one else does, but you cannot put your finger on what it is.

And so doing that exercise of looking not only what you're doing, but the reasons why allows you to dig to find that gold nugget. Of a concept and an idea that you can then turn into a signature framework, turn into workshops, turn into programs, courses, keynotes, whatever it is. And what's incredible is that every single person has this golden thread within them.

And it's such a joy to help people dig out. It's a point of view, a perspective, a philosophy, a way of doing things that is just so powerful and unmistakable. It makes them a magnet for their perfect people.

Srini Rao: Yeah. Wow. You're speaking my language. So much of what you've said is a lot of what I've echoed in my own books.

I, there's one thing that I want to ask you about, you brought up this idea of what somebody does so exceptionally well that nobody else could do it. But then that literally was the core ethos of unmistakable, but where That came from, I think as I was talking to you, I think when we're chatting on Facebook was where I developed this thesis around this was every time I, cause even we started out interviewing bloggers about how they built their blogs and eventually that got really boring.

And I was really fortunate enough to have a mentor who said, trust me, this is about to turn into a gigantic circle jerk. He said, you need to rebrand the show and change direction which we did. And it became much more about interesting stories, which expanded the range of possibilities for who we could have as guests.

But what. Prompted that whole thing was every time I saw people online and I saw it myself and I saw a lot of other people is that they would look at what some other person had done some person who was more successful and say, Okay, this person has a map and I can copy the map and I'm going to end up with the same results.

And of course they didn't. And I remember asking Laura Belgrade about this. And I said you're Marie's copywriter. And I feel like every time I see people come out of B school So often, those businesses are so similar that you can't even tell what each person does. Another friend of mine sent me a list of 10 potential guests, many of who are clients.

I put up all their websites right next to each other in tabs and I turned them all down. I was like, I can't tell what any of these people do. And this is really confusing to me, how do you break people out of that sort of bias towards authority?

Hillary Weiss: Ooh, that's a good question.

So I think that so you and I actually, I do want to make it a point that I'd made when you were talking is I think that imitation is a really reasonable starting point, especially when you're trying something brand new. When you're going into business, of course, you're going to look at who's the most successful and see if you can mimic what they've done and follow their path.

But that's also where a lot of people get frustrated. They get bored because they're wearing an outfit that's not made for them. Right there looking at somebody's business that they've spent years building and trying to mimic that process, but they have no idea what else goes into creating that business and why they do things a certain way and why they sound a certain way.

But when it comes to breaking sort of my clients out of that and helping people see. That they have something unique to bring to the table so often, it's as simple as a matter of confidence as somebody standing in front of them, holding up the mirror and saying, Oh, my God, look at what you can do.

And this is not on your website. This is not anywhere. Why aren't you talking about this? And I talk about it again, like the elevator. One floor deeper. I think that people also get tied up in knots about what's going to make them look professional, what's going to help them fit in. We all want to belong.

We are a herd species and a tribal people. We all desire that sense of belonging. And also there's such a massive vulnerability in being like, okay, I do this really well and this is who I am and this is exactly how I want to come across. And unfortunately, or fortunately for me, I've always had a Godzilla of a personality, so I didn't really have an option.

I just came out of the womb and I was like, I'm here to go and I'm going to do it my way. But a lot of people aren't unfortunately fortunately or unfortunately born with that. But I think that you look to examples in the space and of course you want to mimic what's successful in people that you like.

But what the magic really starts happening. When you start to do that self examination, when you start to think, okay, am I doing this because Marie Forleo is doing it, or am I doing it because this is relevant to me? And there's either an awakening that happens, or the business plateaus or collapses.

So I think a big part of it is understanding and accepting if you're imitating because you're new. And then making that decision to pursue exactly what you want and exactly who you are is so huge. But then we also, of course, have that category of people who think they figured it out, and then they all sound because they're, they've decided to have sassy copy, they feel like they have more personality now.

So I think there are some... There's, you can get caught up in the superficial nature of it if you're not willing to do the deep work. So there certainly are layers to this, where you start sounding like super professional, and then you realize you can do funny cappy and funny branding, so you do that, but it's, you're imitating Laura Belgray.

And then, only then can you look around and realize, wait a minute, This isn't necessarily me. I'm exhausted trying to play this character. So how do I dive in to figure out who I really am and what I really want?

Srini Rao: Yeah I remember one of my friends when I, there was a time when there used to be this thing called blog world, I think it was in 2009.

And he told me, he said, your rebrand was basically a fuck you to the entire system. I was like, Yeah, maybe he said, you basically just turned your back on all of it. And I realized I was like, I don't want to talk about this stuff. Like I have no interest in online marketing. I'm like, yeah, it's necessary to do what we do to some degree, but it's.

Not what I want to create.

Hillary Weiss: I think that what's one, I'll tell you a funny story. So I have a, an opt in is called the statement piece framework. My business is state and peace studio. And it's really it's a content concept sort of tool where I'm forcing people to do something that I don't think a lot of entrepreneurs do right now, which is examine.

Their own thoughts, examine what they really feel about things, because I think especially in the online business world where all people know of you as a digital face, it's really easy to be like, okay, I'm going to play it safe. So everyone thinks I'm a important authority and I'm not going to rock any boats, but in the statement piece framework.

I'm forcing people to look at what I call the three statement piece scenarios, which are conversations with colleagues, conversations with clients, and conversations with yourself. And there are two categories in these conversations, which are advocate or anti, which I described earlier, where it's okay, so in a conversation with a colleague, for example, let's say you're out to dinner with your business bestie or a bottle of wine deep.

What is something that they say that if you are anti, you're like, Oh my God, if nobody ever says that to me again, it will be too soon. Can we wipe the scourge from the earth? I can't stand this trend or this brand. And then similarly if you're having an advocate conversation, it's, I'm so nerdy out about this.

I'm really excited about this breakthrough. So we have that anti those anti and advocate points of view in the tool that people can use. And what was really funny. is I had a bunch of, especially women, come to me up at conferences, replying to my emails, telling me like, hey, so I had the statement piece framework and I don't know how to tell you this, but I'm way more anti than advocate.

I feel like I have a lot of, I just, I thought about what I was mad about and I was just writing writing and it was like something unlocked in my head and I was like, yeah that's part of examining your own ideas. What you don't like is often a much more valuable point to start at than what you do or what you think is cool.

So it's been really interesting. I actually also have a workshop called Start With Nah. The best personal brand strategy you're not using. So I'm 100 percent with you there. But it's really interesting that especially as women, because we're socialized to, to appease, to be kind and to be accepting and not really rock the boat.

Watching so many of these business owners dig into and start noticing their own thoughts and realizing that they're valuable for content and are going to help them come up with more original ideas, but also seeing them examine. What don't I like, and why am I so much more excited to talk about what I'm frustrated about or don't approve of than what's generally okay in the industry.

So it's interesting to see people have that aha.

Srini Rao: Yeah. It's funny because it makes me think of two things that both who happened to be women who said to me on the show, the first was Tara McMullin, who said there's great creative potential in the things that make you angry. And Justine Musk said if you have a bold and compelling point of view, it's going to piss people off.

I think that once I was okay with that was when I realized, okay the most resonant content is inevitably going to polarize people. When I look at the stuff that has been the most popular, some people absolutely fucking hate it. And some people love it. And I literally have had my work called two things, a gift to the world and a disservice to humanity.

Nice.

Hillary Weiss: Yeah. The thing, but the thing is, people are so terrified of being able to do that. You mentioned women in particular have been socialized to be nice, be kind appeasing, whatever, but two things come from this one. The reason this is fresh on my mind is one thing that I've seen in my own readers that comes up over and over again is they think that they lack creative confidence.

Srini Rao: And I wonder how do people build the confidence to have. an opinion that pisses people off and realize that, you know what, that's just going to be part of doing this. I realize you just cannot create something that is going to be resonant with an audience if you're not willing to alienate people.

Hillary Weiss: Yeah. I think it's also the gravity of displeasing people on the internet is not what we think it is or necessarily what we let it be as well. So when we think about that creative confidence, That willingness to go and say the unpopular thing or something that you know, is going to piss people off.

I built my content strategy around that for a really long time. And I think that for a lot of my clients, I explain one, it's a reps thing. You just have to start doing it. And then you, when you realize one or two comments that disagree with you, aren't going to kill you, you have a lot more confidence to move forward.

But I think it's also a matter of. Checking in with yourself about how much conviction you have about your own ideas. If you really believe in something, if you really believe what you're saying, you should be okay with people disagreeing with you. And I think that a big part of what gets people scared about putting out polarizing content is that they're not, they're going to be ashamed.

They're going to feel that awkwardness. They're going to have that sinking feeling in the pit of their stomach. But most of the time. That's not going to kill you, A. And B, when you're really confident and believe in what you're saying, when you've taken time to develop the idea and really understand it, you're able to roll with disagreement a little more, because hopefully you've had your head in that spot where that commenter is, and you know where they're coming from.

But it's also really important when you're writing about polarizing ideas, I think to also focus on empathy as well. So I always tell my clients, if you're going to write something polarizing, You're going to talk about the other side. It's really not helpful to attack an individual. What you do is attack a system and a way of thinking, but you also acknowledge that you understand why people think that way.

And that actually helps to, first of all, address any negative feedback you might get, make you more comfortable because you've been kind and empathetic or as kind as you can be. And again, helps you hold that idea up to the light, examine it from all angles so that You believe what you're saying.

So if you get that pushback, you're ready for it. And you're comfortable accepting it.

Srini Rao: Yeah. After the whole Netflix thing, I ended up writing this medium article titled the South Asian arms race for impressive bio data. And I made it very sure to make sure that I didn't just. Paint the negative side of growing up in Indian community.

I said, look, there are a lot of positives to this as well as we talked about earlier. I made sure to highlight that because I was like, I don't want people to be like, Oh, this is just Srini pissed off about his culture. I think there's a difference between being polarizing and being an asshole.

And I think that this is something I've wondered and maybe you can answer for me. I had this guy here Stephen Goldstein, who basically worked with Oprah worked with a number of politicians. He wrote a book called the turn on how the most powerful people from Washington to wall street to Hollywood make us like them.

And one thing that I realized just in, in the wake of Netflix and having more and more of a public presence is as you become more and more known in the public eye. Your actions are no longer just a reflection on you. They're a reflection on a lot of other people. Like for me, it's investors, editors, agents.

And the thing I wonder is how do you maintain that idea of being polarizing without going over the line? Because I've seen people like, Oh, I'm just being opinionated. I'm like, no, you're not being self aware. There's a difference here. And so where's that balance between pushing it too far and being self aware enough to realize that, okay, wait a minute, this might not be appropriate for public consumption.

Hillary Weiss: Yeah, I think that's, first of all, again, a reps thing. That's a practice thing. You've got to push the envelope to figure out where the edge is, right? And I think that there's certainly some things in my past that I wrote maybe four or five years ago that I'm like, Ooh, maybe that wasn't the best idea. But I think it's really about being deeply connected to your values as well.

So for example, you're talking about The Medium article that you wrote also about the positive experience you have had growing up as a South, in a South Asian, East Asian family. And I think that what is really important there is that if you have that consistency of approaching things with empathy, of trying to say not this is wrong because I say so.

Go to hell. But you want to explain the, you want to be able to approach with empathy these ideas, to see the other side and have that self awareness. If you consistently come from that angle, most of the time you're going to be okay, but where you run into challenges, of course, is if you have people behind you, as you say, who, if you make one gaffe, if the whole house of cards collapses.

But that's also a matter of what is your brand? I often find that kind of stuff happens when something totally inconsistent with the overall brand just comes out of left field. If, for example, I don't know the politics of your following, but let's say you have an influencer who's all about female empowerment, and then you find out they're a Trump supporter and a really, Loud one at that, and really into all the things that have been going on in the last four years.

I think that's a surprise that can create huge waves. But if you are, again, coming, if you are a wellness influencer who decides to write, for example, like one of my, like my coach did, write a big book about anti diet culture and what's wrong with the wellness industry from that place of not just compassion, but about what's possible to do instead because she has that expertise and that knowledge.

I think that doesn't come quite as out of left field and that's polarizing content that can actually help people. So I think the more, the bigger and bigger you get, the more and more important it is to stay connected to your values, even if those change. Because if you're consistent with what you're polarizing about, if you're consistent with the way things and talk about things, it becomes less of a, Oh my God, I can't believe you said that.

And more of a there's Srini. Yep. That's what he does. All right. Cool. This was interesting. I like that he makes me think.

Srini Rao: Yeah. No even Netflix thing, somebody said they saw the conversation with the matchmaker and they're like, dude, you did exactly what you do. You interviewed her.

You didn't answer any of her damn question. All right. Trust me. I'm like, I understood one thing after reading the 48 laws of power. I was like, the person who asked the questions is the one who's going to control the conversation. Is that

Hillary Weiss: why you like being a podcast host so much? I actually don't like doing interviews for that reason, because I know that I talk too much and I'll say something stupid.

Srini Rao: There's always that risk.

Hillary Weiss: And if it, but if it's on brand, you're going to be okay.

Srini Rao: Yeah, I know. I definitely people will ask, but I've noticed that when I am interviewed nowadays, I tend to be extremely opinionated about the things I believe.

Hillary Weiss: Yeah. Hey, as you should be. I think also we're in a really interesting time where there's so much content.

And there's so much stuff that people are putting out and so many conversations happening at any given time. It's also possible that there's so much noise going on. People don't even have the time to get really irritated about what she said. So that's a small comfort to me too.

Srini Rao: Yeah I think people forget that it's like something that is like the talk of the town this week is going to be an afterthought by next week.

Yeah.

Hillary Weiss: And I tell this to my clients too. And it's discouraging from the outset, but it is, it's a help to me. Nobody thinks about you as much as you think about yourself.

Srini Rao: Yeah that's a good point. So as far as your clients go, what have you seen as patterns between the end differences between the ones who do really well versus the ones who don't?

Hillary Weiss: It's a commitment and a willingness to focus on one thing at a time. I have some, again I don't really have any I, I don't want to be like I have some bad clients. But I think when it comes to building a business, building a following, building a platform what's really important is consistency and focus usually on one or two things to start with.

So for example, if you really want to build a following, you either start on pick Instagram, pick LinkedIn, go with one. And then really go hard in the paint there, and then we can start doing other stuff. Where I find people get lost in the sauce is that they're like, Okay, so it's 2021, I'm gonna get on my content creation game, and we're gonna do daily LinkedIn videos, we're gonna do Instagram stories, we're gonna be on Facebook, we're gonna do TikToks, whatever that is, and then They get 10 days in and they realize they can't possibly juggle 50 things or go deep with 50 things and they get frustrated, discouraged, and they give up again and they're back to square one.

I think that there's a lot to be said for focus and most importantly, depth. Depth of exploring the ideas, depth of focus, depth of a deepening of your approach to a single platform and a sharing of a single idea. is going to be so helpful in helping you figure out what you're doing really well, what you want to talk about, and get you known for that thing so people can recognize you.

If you're trying to be an octopus juggling 12 different social media plates because you think that's where you're supposed to be, you're just going to get lost. So I think that clear focal point, but also, as I mentioned before, that conviction. So we have that positioning, we have that focus, which is built on who they are, what they value, what they do really well, what their kind of magic is.

And if you stay focused on that, you can't help but magnetize people towards you where it's, but it's easy to get distracted because there's so many things that we're supposed to do in the online space as well. Yeah. I appreciate that more than you can imagine. Cause I remember my mentor, Greg, when he sat me down to start working with me, he said, he made me make a list of all the things I was doing to make money.

Srini Rao: And then he said, okay, do you want to be doing any of this in five years? And I think there was one at the top of the list, which was the podcast. And he said, then stop doing the rest of them now. And I think that I've been working on this piece about the things that I would do differently if I started today.

And the conclusion I basically came to was don't be average at a dozen things, be extraordinary at one.

Hillary Weiss: Amen. But it's so counterintuitive because it's like the Harvard Jam study, right? The, have you heard about this? I don't think so. Oh, so this is big in the copywriting world. This is big in like the copywriting and offers like development world.

So there's this Harvard study done about it's the Harvard Jam study. So it's in a grocery store. There were two sort of setups for jam. So one had 20 different types of jam, all kinds of different labels, glorious jam options for everybody. The other display had maybe, I think, three or four types of jam available.

That's right. I do remember this. Yeah, I was like, you've got to know this. But the, so and it turns out, so when we think about value, when we don't have any experience in interacting with consumers and understanding what consumers want, it's really easy to be like, The 20 jams are the way to go.

We want to give them as many options as possible. We want to have as many options as possible to get them. This is going to be great. But in the study, people faced with the 20 jams didn't buy anything because they were overwhelmed. Whereas you looked at the three to four options on that display, people bought a ton because they were, it wasn't as complicated.

And I think our brains aren't as good as we think they are as maintaining a million things. Hey. But also having a million choices. So being in a million places, doing a million things can feel like you're widening the net and welcoming in opportunities. But in reality, you're tend to be distracting yourself most of the time and setting yourself up in some ways for failure.

Srini Rao: Wow. I feel like I could talk to you about this stuff for like hours on end. You're like a wealth of knowledge about all of this. I know you got to go and say, I want to finish my final question which I know you've heard me ask. What do you think it is that makes somebody or something unmistakable?

I

Hillary Weiss: think it is. Was encouraging conviction. I think you got to find that nugget you hold on to that you ring the gong and that could change as time goes on. Of course, you know that can evolve and shift but having that Conviction in who you are and what you do in that bravery To show up every single day as exactly who you are with exactly your skills and gifts and not tamper them.

Don't turn the volume down. Don't water yourself down. Don't mix it with anything. I think that is what makes people unmissable, unmistakable, and irresistible to the people who need to be in that energy. That's what it, that's what it means to me, I think.

Srini Rao: Amazing. I can't thank you enough for taking the time to join us and sharing your story and insights with us.

Where can people find out about you, your work and everything that you're up to?

Hillary Weiss: Oh, this is where I can use my radio voice. Okay. So you can visit, you can learn more about me on my website, hillaryweiss. com. That's H I L A R Y W E I S dot com. You can also find me on Instagram at handle H C as in Cookie H C Weiss, which are my initials.

You can find me on Twitter, talking smack at the same handle. And if you reach out to me on Facebook, I will be Hillary Weiss Presley, which is my married name, but I would love, love, love to hear what all of you think of this episode. If you want to DM me with your biggest takeaways on any of those platforms, I would love to chit chat with you and show you this has been an absolute honor, a pleasure and a privilege.

Thank you so much for having me.

Srini Rao: Absolutely. And for everybody listening, we will wrap the show with that.