Dec. 7, 2021

Best of 2021: Hillary Weiss | Turning Brazen Ideas into Clear Concepts that Captivate the World

Best of 2021: 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.

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

Hillary Weiss: Thank you so much for having me. I'm so excited for you.

Srini: 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.

Srini: 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. Oh, my

Hillary Weiss: 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.

Hillary Weiss: 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 hoopy. And pre-K and who did the embarrassing thing and second grade? So I actually, I wasn't one of those social groups that wasn't, I was not popular.

Hillary Weiss: I was also not in the total reject spot. I was in the 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 I have a group.

Hillary Weiss: Do 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 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 done.

Hillary Weiss: 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 super-low it is in my senior year yearbook. I actually won class clown much to my surprise cause I didn't talk to most of my class, but I did make funny comments with my English teacher.

Hillary Weiss: Apparently this is what I was told. So winning class clown made me feel way more relevant than I actually was.

Srini: Yeah. So I wonder, how you, that affects the depth of the friendships you have, because I, I'm putting together a tribute video from my sister. Andrew Horn has this company called tribute, which is like hallmark 2.0 where people just send in videos and her birthday is coming up and.

Srini: Yeah, my sister and I had very radically different upbringings because I moved around constantly. Cause my dad was still building this career. He hadn't gotten his tenure track position, but she had a lot of the same friends in sixth 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.

Srini: 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 like 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.

Srini: Like they have a WhatsApp group. 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 14 years? It's such

Hillary Weiss: a great question. I think for us, it is a, for the girl gang, but I hang out with that I've known forever.

Hillary Weiss: 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 Gerardi who you can find on Instagram and Tik TOK is a spokesperson for the future of space.

Hillary Weiss: And then Maggie Speiser. Yeah, she's amazing. She's actually worth interviewing on the show. She's incredible. And then another dear friend of mine is her name is Nancy Spicer. She is, she works for a powerful law firm in DC, international trade law. Our other friend, my other friend, Kat Cassidy.

Hillary Weiss: She's getting her PhD at St. Andrews in Scotland and computers. So we all split across the world and really got deeply focused on our careers. And, I started a business, I 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.

Hillary Weiss: 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.

Hillary Weiss: 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 end, from high school or grade school. Like I remember my sister bless her. I have an older sister.

Hillary Weiss: Who's about four years older than me who actually sat me down before I graduated college, before I graduated high school. It was like, I want you to know that you're probably never going to talk to your high school friends again. I was like, she also ruined Santa Claus for me in a similar way. But. I was like, oh, now we all love each other.

Hillary Weiss: We're going to 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.

Hillary Weiss: 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 that there 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.

Srini: Yeah. When Lydia denworth here, who wrote a book on a 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 of this. What's changed about these friendships over the course of your life.

Srini: Oh

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

Hillary Weiss: We felt a little bit out of touch. And then. We all reconnected enthusiastically. But I think, and I think of course in high school, there's all the disagreements about boys and all of those things happened. Oh yeah. Oh God, John. I could tell you stories. But I think that what has changed has been probably.

Hillary Weiss: The amount of energy. We also require from each other, which is interesting. I think another really important thing about adult friendships actually is there's, especially in the digital age of belief that you always have to be connected. Always answer the tax don't ghost on the group chat quote, unquote, but need space, like not to re a reply to deal with what's in their lives and have a place to come back to a friend group to come back to it.

Hillary Weiss: Some people don't like that. Some people aren't in. If I don't respond to the group chat for a month, when I come back being like some crazy stuff happens, some people are going to be met. But you ha there's that sort of mutual symbiosis of understanding that we have lives and we love each other.

Hillary Weiss: And just because we're not replying to every single text right away doesn't mean that, that friendship and that love isn't there. And I think we had that unspoken agreement. That's so important to maintain those kinds of friendships. Yeah.

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

Srini: Yes

Hillary Weiss: and no. So I I graduated high school in 2007, so it was it was June, my junior year of high school was when Facebook was big and I was on live journal and MySpace before. That was chaos. That was like the wild west of social media era. I don't know how much you remember,

Srini: A bit older than you.

Srini: So I graduated high school 1996, which is why I asked the question because I always wonder how that would impact, the depth of friendships, 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 few curl at a party, Now I could go and look her up on Facebook and actually go contact her and college.

Srini: 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 isn't, the ability to disappear has vanished in the last 20 years because people find, sadly people can find you the Netflix.

Srini: I have no privacy anymore.

Hillary Weiss: I wasn't going to ask, but I was curious, but I think what was interesting is I experienced like the really early form of cyber bullying when I had live journal and like my freshman year of high school, like I had bet some mean girls hack into my email account at all of these things.

Hillary Weiss: 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, being able to find someone at a party that you made out with, and I've tried to never speak to again and then gave it a shot and y'all realize you had nothing in common.

Hillary Weiss: I think the gossip stream was so powerful in college as well because of social media. And I don't know if. 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.

Hillary Weiss: Oh yeah. And then, and it was, I think the site was shut down. At obvious reasons. But that was so I just remember that was so interesting to me. I was like, is this social media getting out of control? But what my familiarity read that also allowed me to build a business via social media and the internet, basically, as soon as I had gotten out of college.

Hillary Weiss: So I gotta give props where perhaps, or do you

Srini: will. It's funny because that kind of thing probably wouldn't have done so well. Cause I went to a college with 40,000 undergrads. Berkeley just had such a massive student body. There's no way. Wow. Okay, cool. So you have these friends who sound like they're, movers and shakers.

Srini: 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: 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 oh nine, 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 that I think jumped head first into a kind of more unusual career from that friend group. And I had all their stuff. But what was interesting is that no one really believed I could do it.

Hillary Weiss: 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 public relations was my major.

Hillary Weiss: There were no public relations job worth anything really. So I had to jump into copywriting and 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 talk on her desktop, all of our little friend groups.

Hillary Weiss: So I can send you a link to that if you're curious. 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 working her way towards.

Hillary Weiss: Working in the sciences, but she actually has a film degree, which has 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.

Hillary Weiss: And how are you doing it? Can I, and her question was, can I get paid to just be off. And I was like, actually, yeah, you technically, can you just have to figure out a way of 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.

Hillary Weiss: 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 has. Everybody saw what they wanted and were able to go after it. And especially in Maggie's case use the power of lawyers. She was always going to be a lawyer, always had her sights set on what she wanted.

Hillary Weiss: Cat always wanted to go to St. Andrew's whatever she was, whatever 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.

Hillary Weiss: As well with our less, certainly less barriers. And there would have been even, 30 years.

Srini: Yeah. One thing I wonder is, you've mentioned you have a sister who 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.

Srini: 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 want, I'm curious, what kind of advice your parents gave you about making your way in the world? And then. When you're the odd ball person who decides to go do something where there isn't a clear path, how one, what's useful about how you know that you can draw from, clear trajectories.

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

Hillary Weiss: I love this caution cause it's complicated. So I might ask you to give it to me again. If we're asking me about my parents thought I was out of my mind, like they were like, oh dear honey, we love you so much.

Hillary Weiss: 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. 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.

Hillary Weiss: 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 actually got fired for obvious reasons because I would sit and write really crappy pitches and then work on my business during, at work hours, which wasn't, the most professional thing of means to do.

Hillary Weiss: So I got And I was still in Miami at the time. And I remember calling my parents. 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. Oh, no. We're not going to help you financially so your way. But then they thought I was even crazier for moving up to New York city a year later.

Hillary Weiss: Because he wasn't that they were, they didn't believe in it wasn't, they didn't believe in me necessarily. But I think that they were just, they had never. 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.

Hillary Weiss: 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 went ahead and found my way and the nature of my personality is very much like I'm going to do what I want to do, and I'm going to figure.

Hillary Weiss: But 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 led 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, Okay, why are you doing this?

Hillary Weiss: 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, try to get a job in an agency. And I just refused, but because I, it wasn't going to pay me as much as I was making in my business already at that time.

Hillary Weiss: 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.

Hillary Weiss: But I'm 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. A couple of days ago, throwing those hail Mary is being like, I think I want to do this.

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

Hillary Weiss: 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. So anyway, but that's the nature of who I am as a person.

Hillary Weiss: It's also the nature of my Zodiac sign. I'm a tourist. So I will just barrel through anything like a bull in a China shop, but now I'm rendering what the second half of that question is because I've completely forgotten in my range.

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

Srini: Because I think the. You 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.

Srini: But I. Outside of that. There was some really intangible skills that came from being raised by the parents. I had like 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 a $5 for every day.

Srini: 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 invalid. 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.

Srini: 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 this confirmation bias kicks in. 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.

Srini: 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.

Srini: 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: 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 am 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.

Srini: And I was like that's great. If Reed Hoffman is the investor in your business, if not, you're going to plumb it to your there's. No parachute. 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.

Srini: 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 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's first of all, I'm actually, I retired from copywriting last year.

Hillary Weiss: I'm a creative director and positioning coach at this juncture. But I was a copywriter for 10 years and yeah, 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.

Hillary Weiss: 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, why are you on some kind of reward? Good job. Knowing 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.

Hillary Weiss: We put clothes on your back and food on the table. What more do you actually need? Get a job? And I did, I had a job from a very early age. And I think that, and it was a. The millennial generations, the quote, unquote snowflake, the participation trophies. My parents were really against that culture and that shift in culture.

Hillary Weiss: 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 of these things that you've described.

Hillary Weiss: And what was really interesting to me actually. 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.

Hillary Weiss: People 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 serious. But I got into the industry and I realized that I'm not the smartest. 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.

Hillary Weiss: I will outwork any of my competitors and that's what I did. And that was kinda my ethos. Anything a client threw at me. 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 that I worked.

Hillary Weiss: 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.

Hillary Weiss: And then of course you hit a tipping point where you burn out and you look behind you and your. We'll wait a minute. Maybe I don't actually have to work this hard. So really thinking of that approach and that like 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 there's so much danger in telling my story and being like, I did it.

Hillary Weiss: You can do it too, because there's such a large range of factors that come in. 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. Cause 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 when.

Hillary Weiss: If everything went belly up, then I was destitute and I would've had to go to a shelter. There was always the opportunity that if everything went belly up, I could go home and my bands would feed me, put a roof over my head. There was always that opportunity. So while of course I don't want to totally.

Hillary Weiss: Take away the the story of people who are in my position. Cause 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.

Hillary Weiss: 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. 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.

Hillary Weiss: 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 in. 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.

Hillary Weiss: And having that attitude that like I can do it. You can do it too. Gary V tells you. 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 where do we come from and what allowed us to have this ability to be courageous and take these risks.

Hillary Weiss: So I love that you brought that up. Can you imagine getting paid to do what you actually love doing? Tell us what those things are, and we'll tell you how you can do them in the army. Go on, get paid for doing what you love. Search, do what you love.

Srini: Yeah. I think no doubt. I'm in a similar position to son of a colored professor. My parents let me live at home for eight years while I was doing this

Srini: well into my late thirties, it was ridiculous. 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. Got it together within a year, you'll start looking for a job he's cause they just need to hear that.

Srini: 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 were like, nevermind, was this 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.

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

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

Hillary Weiss: Why burning man ruined.

Srini: 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.

Srini: 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 actually happens.

Hillary Weiss: So I there's a couple it's all right.

Hillary Weiss: There's a couple of 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 my positioning work. 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 that 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 same.

Hillary Weiss: 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 about. The run of the mill business coach, like I'd help my, oh, sorry.

Hillary Weiss: I help 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 gonna say that, and they're gonna 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.

Hillary Weiss: When I say like one floor. So it's okay, you want to do this for, help these clients find their voice and great more stuff online, but why is that? Why is it so important to you? What are you coming to the table with? You do so uniquely well that nobody else does. And how do we build from that?

Hillary Weiss: And so when I talk about brazen ideas, Turn into concepts that captivate the planet. I really helped 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 why should they love about their industry and what do they hate about it?

Hillary Weiss: What are they counteracting with their work that they believe in, or don't believe in? What do, what is the something that a client says to them that they're like, oh God, 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.

Hillary Weiss: And part of how we do that is of course, we talk about the, 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 walked them through an exercise where it's let's say you're a copy of. And you take your clients through a series of steps, but what are those steps and most important? 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 at what you're doing, but the reasons why allows you to dig to find that golden.

Hillary Weiss: Of a concept and an idea that you can then turn into a signature frameworks, turned 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.

Hillary Weiss: It makes them a magnet for their perfect.

Srini: 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've, there's one thing that I want to ask you about your, you brought up this idea of what somebody does, so exceptionally well that nobody else could do it.

Srini: But then, that literally was the core ethos of unmistakable, but. That came from, I think as I was talking to you, I think when we were chatting on Facebook was where I developed this thesis around. This was every time I, because even we started out interviewing bloggers about how they built their blogs.

Srini: 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. Jerky 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.

Srini: But. Prompted that whole thing was every time I saw people online and I saw it in 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.

Srini: And of course they didn't. And I remember asking Laura Belgray about this. And I said, you're Murray's copywriter. And I feel like every time I see people come out of. 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 whom are clients.

Srini: And I put up all their websites right next to each other, in tabs. And I turned them all down and 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.

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

Hillary Weiss: 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 core mimic what they've done and follow their path.

Hillary Weiss: 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. They're 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.

Hillary Weiss: 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.

Hillary Weiss: 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.

Hillary Weiss: 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.

Hillary Weiss: I just came out of the womb and I was like, I'm here going, I'm gonna do it my way. But a lot of people aren't, unfortunately, fortunately or unfortunately born. But I think that. You look to examples in the space and of course you want to mimic what's successful and 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's doing it, or am I doing it because this is relevant to me.

Hillary Weiss: 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 with you're imitating because during. 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 sounded like, because they're, they've decided to have sassy copy.

Hillary Weiss: They feel like they have more personality now. So I think there are. 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 copy and funny branding.

Hillary Weiss: 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 whatever. Yeah.

Srini: 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, you're a free brand, was basically a fuck you to the entire system.

Srini: I was like, yeah, maybe he said, you basically 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 and I'm like, yeah, it's necessary to do what we do to some degree. Not what I want to create.

Hillary Weiss: Yep. And I think that what's one, I'll tell you a funny story.

Hillary Weiss: So I have a, an opt-in is called the statement piece framework my businesses statement piece 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.

Hillary Weiss: Because I think especially in the online business world, 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.

Hillary Weiss: 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 best to your bottle of wine deep. What is something. That they say that if you are anti you're like, oh my God.

Hillary Weiss: If nobody ever says that to me again, it will be too soon. Can we wipe the skirt 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 nerding out about this, I'm really excited about this breakthrough. And so we have that anti, those Anton advocate points of view in the tool that people can use.

Hillary Weiss: And what was really funny is I had a bunch of, especially. 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 address. I thought about what I was mad about and I was just writing writing, and it was like something unlocked in my head.

Hillary Weiss: Yeah, that's part of examining your own ideas once you don't like is often a much more valuable point to start at then once you do or what you think is cool. So it's been really interesting. I actually also have a workshop called start with. The best personal brand strategy. You're not using some a hundred percent with you there, but it's really interesting, 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.

Hillary Weiss: 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 then what's generally okay. In the industry. So it's interesting to see people have that.

Srini: 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.

Srini: And Justine Musk said, if you have a bold and compelling point of view, it's going to piss people off. And I think that once I was okay with. That was when I realized I was gay, 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.

Srini: And some people love it. And like I literally have had to my work called two things, a gift to the world and a disservice to humanity.

Hillary Weiss: Yeah,

Srini: 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.

Srini: 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. 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.

Srini: Like I, I realized you just cannot create something that is going to be resonant with an audience. If you're not willing to alienate.

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, that willingness to go and say, the unpopular thing or something that you know is going to piss people off.

Hillary Weiss: I built my content strategy around that for a really long time. And I think that for a lot of my clients, explain one, it's a rep. 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 forward.

Hillary Weiss: 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. And I think that a big part of what gets people scared about putting out polarizing content is that they're knocking, they're going to be ashamed.

Hillary Weiss: 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.

Hillary Weiss: Yeah. You're able to roll with disagreement a little more because hopefully you've had your head in that spot where that comment or is, and you know where they're coming from. But it's also really important when you're writing it up. Polarizing ideas, I think, to also focus on empathy as well.

Hillary Weiss: So I always tell my clients, if you're going to write something polarizing, if 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. But 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.

Hillary Weiss: 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 with.

Srini: Yeah after the whole Netflix thing, I ended up writing this medium article titled the south Asian arms race for impressive bio data.

Srini: And I made very sure to make sure that I didn't just put, 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, Shreeny pissed off about his culture.

Srini: I think there's a difference between being polarizing and being an asshole. Yeah. I think that this is something I've wondered in and, maybe you can answer it for me. I had this guy here, Stephen Goldstein, who basically worked with, Oprah. He worked with number of politicians.

Srini: 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 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.

Srini: 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, 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.

Srini: 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 health.

Hillary Weiss: Yeah, I think that's, first of all, again, a rep thing, that's a practice thing. You got to push the envelope to figure out where the edge is.

Hillary Weiss: And I think that there are 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 south Deanna, Southeast east Asian family.

Hillary Weiss: 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 like this is wrong, because I say. 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.

Hillary Weiss: 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? Like I often find that kind of stuff happens when something totally inconsistent with the overall brand just comes out of left field.

Hillary Weiss: 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. Loud one at that and really into, all the things have been going on in the last four years. I think that's a surprise that can create huge waves.

Hillary Weiss: But if you are again coming, if you are a wellness influencer who decides to write, for example, like one of my, like my. 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 in that knowledge, I think that doesn't come quite as out of left field and that's polarizing content that can actually help people.

Hillary Weiss: 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. 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.

Hillary Weiss: I can't believe he said that. And more about, there's Shreeny yep. That's what he does. All right. Cool. This was interesting.

Srini: Yeah no. Even, the Netflix thing that somebody said, they saw a conversation with a matchmaker and they're like, dude, you did exactly what you do. You interviewed her, you didn't answer any of her damn questions.

Srini: I'm like, 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.

Hillary Weiss: Being a podcast has so much.

Srini: I actually don't like doing interviews for that reason because I know I talk too much and I'll say something stupid.

Srini: There's always.

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

Srini: Yeah. No, I definitely, people will ask, but I've noticed that when I am interviewed nowadays, I tend to be extremely opinionated about the things they

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

Hillary Weiss: And there's so much stuff that people are putting out in 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 candid about what she said. So that's a small comfort to meet them.

Srini: 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.

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

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

Hillary Weiss: Oh, it's a commitment and a willingness to focus on one thing. 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.

Hillary Weiss: So for example, if you really want to build a following, you either start on pick Instagram, picked LinkedIn, go with. And then really go hard in the pain 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 going to get on my content creation game and we're going to do daily LinkedIn videos.

Hillary Weiss: We're going to do Instagram stories. We're going to be on Facebook. We're going to do tic-tacs, whatever that is. And then they get 10 days in and they realize they can't possibly do. 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.

Hillary Weiss: I think that there's a lot to be said for focus and most importantly. 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 gets you known for that thing.

Hillary Weiss: 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.

Hillary Weiss: 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.

Srini: Yeah. I appreciate that more than you can have, because I remember my mentor, Greg, when he sat me down to start working with me, he has said he made me make a list of all the things I was doing to make money. And then he said, okay, do you want to be doing any of this in five years? And I had things that were one at the top of the list, which was the podcast he says and stopped doing the rest of them now.

Srini: And 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.

Hillary Weiss: Amen, but it's so counterintuitive because it's like the Harvard jam study, right? The, have you heard about this?

Hillary Weiss: 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 good. The Harvard James study. So it's in a grocery. 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.

Hillary Weiss: The other display had maybe I think three or four types of jam available. That's right. I do remember this. I was like, you gotta know this. But the and it turns out, so when we think about value, when we don't have any experience in interacting with consumers or sitting what consumers want, it's really easy to.

Hillary Weiss: The 20 jams or 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 face with the 20 jams didn't buy anything because they were overwhelmed. Whereas you looked at the three to four options on that.

Hillary Weiss: 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. As maintaining a million things, eh, but also having a million choices. So beating in a million places, doing a million things can feel like you're widening the net and welcoming and opportunities.

Hillary Weiss: But in reality, you're tend to be distracting yourself most of the time and setting yourself up in some ways.

Srini: Wow. I feel like I could talk to you about this stuff for like hours on end. You're like, oh I know you got to go and say, I want to finish my final question, which I know you've heard me ask.

Srini: What do you think it is that makes somebody or something unmistakable?

Hillary Weiss: I think. Was it courage and conviction. I think you got to find that nugget, you hold on to that you, you ring the gong and that can change as time goes on. Of course, 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 guests and not tampering.

Hillary Weiss: 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. So the people who need to be in that energy. So that's what it means to me.

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

Srini: Where can people find out about you, your work and everything

Hillary Weiss: that you're up to? I can use my radio voice. Okay. So you can visit, you can learn more about me on my website, Hilary That's H I L a R Y w E I S You can also find me on Instagram at handle H C. Cookie HC Weiss, which are my initials.

Hillary Weiss: 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 chitchat with you and show you this has been an absolute honor, a pleasure and a privilege.

Hillary Weiss: Thank you so much for having

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

Hillary WeissProfile Photo

Hillary Weiss

Hillary Weiss is a creative director, positioning coach, and founder of Statement Piece Studio @ She’s also the co-host of the cult-favorite Youtube marketing talk show Hillary and Margo Yell at Websites (#HAMYAW), and has had her work featured on Business Insider, The Next Web, The Observer, and more. Since 2011, she’s helped thousands of brands all over the world get seen and heard (and make serious cash) through her 1-1 client work, writing, coaching, and videos. Nowadays, she’s on a mission to help more small businesses define their “statement piece”, a.k.a. the bold point of view that makes them radically relevant to their perfect people.