March 26

Using Brazen Ideas to Captivate the World

A talk with Creative director, Hillary Weiss

In this interview, Hillary Weiss shares how we can take brazen ideas and use them to captivate our audience.

Hillary is a creative director, positioning coach, and founder of Statement Piece Studio @ She’s also the co-host of the cult-favourite YouTube marketing talk show Hillary and Margo Yell at Websites and has had her work featured on Business Insider, The Next Web, The Observer, and more.

Since 2011, she’s helped countless brands all over the world get seen and heard earn thousands of dollars through her 1-1 client work, writing, coaching, and videos. Today, 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.

Let’s dive right in!

What social group were you a part of in high school? How did that impact the choices you made throughout your life?

Hillary grew up in Suburban South Florida, where she attended the same school for 14 years, from kindergarten to 12th grade. The downside to this is everyone remembers those embarrassing moments from your childhood, like who peed in their pants. Now, Hillary wasn’t part of the “popular” group but also not part of the “rejects;” she was in a “satellite” group of friends that have been together through those 14 years, that orbited around doing their own thing.

In fact, Hillary is still good friends with several people from her high school life. She even has a group of girls who she would travel with every year (before COVID-19). She states that it’s been an incredible source of value in her life, to have those friends who’ve been there since the beginning and seen you through all the phases in your life up till the person you are today.

Once she graduated college in 2011, she was the first (from the friend group) to jump into an unusual career. Now although she had their support, people aside from them didn’t believe in Hillary’s ability to make it successfully. Interestingly, she was the one who inspired them to drive their passion into a successful career. Now they all had their own goals, but to Hillary, it was inspiring to watch them pursue them with drive and conviction.

“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.”

How do you maintain that depth of your friendships later in life?

For them (Hillary and the “girl gang”) there’s a certain desire to maintain the connection to who they were. Many of them, now, have exceptional careers and are split across the world focusing on their professional lives, like Hillary herself started a business right after college, and that took off from there. She believes that a big part of their lasting friendship is because of their driven focus on their careers and lakh of time to make new friends.

“It’s that desire to stay connected to those people who remember who you were before you were so busy and important.”

Now, this doesn’t mean they all stayed together since high school, there were some disagreements along the way and a few of them decided to go their own way. But with the current group, what Hillary believes is so special is their mutual desire to stay connected. That being said, she states it’s natural for friends to fall apart, but to stay together for such a long time there has to be that desire to be connected across miles and years.

Another important factor that goes into maintaining these long-term/distance friendships is the amount of energy they require from each other. Especially when it comes to the digital age and adult friendships, the belief of always staying in-touch – don’t ghost on the group text – can tire out friendships. It’s important to realize people need space, to deal with what’s in their lives, and have a place and friend group to come back to.

With Hillary’s group, they have a mutual symbiosis of understanding that they each have their own lives, and they love each other even though they don’t reply to each and every text right away.

What influence did your parents have on your career?

Hillary was raised in an old-school family, where there are a lot of similarities with the Indian parental culture. To elaborate Hillary quotes an example –

“oh you got an A, that’s exactly what you’re supposed to do, why do you want some kind of reward?

No, you’re not getting $20 to go see a movie with your friends, we put a roof over your head, pay for your education, put clothes on your back, and food on the table. What more do you actually need?

Get a job.”

And that’s exactly what Hillary did. She started working at a very young age. Growing up. Her mother said, “We care about you, but the world does not, so you have to be focused, and work hard for anything you have.” Today, she’s grateful her parents raised her the way she is. When she first started in the copyright industry, she was one of the youngest there, and would often hide her age.

“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 anybody else, any of my competitors. And that’s what I did.”

That was Hillary’s ethos; anything her clients threw at her she’d try to hit. She slammed all her deadlines, and if she didn’t know anything she would research every detail while also being honest with her clients about it. Hillary would make it work, and it got her really far. In fact, she had her first 6 figure year when she was 25!

Even though this work ethic, where Hillary worked 6-7 days a week proudly, she did hit a point of burnout but soon found a more sustainable work ethic. But having that initial drive is what pushed her through. Now that being said she does recognize that she was raised quite privileged and if this path didn’t work out, she could still fall back on her parents until she could stand on her own two feet again.

Now, Hilary states that it’s important to recognize where you come from, and how that’s allowed us to take the risks we take. This is the same approach she takes with her clients, she does positioning coaching to define their position in the market so they can create their content and brand around it. But she also always listens to what they come in with, she refuses to ever use the phrase – “that’s just a mindset.” There’s a real danger with the mindset that “you can do anything”, people can end up spending thousands of dollars to believe in a path that leads to situations they can’t get out of.

“Don’t ever make a major life decision based on a peak experience.”

It’s important to recognize context and build from there because people are coming as a sum of their experiences and they may lack that level of security could do more damage than help.

“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?”

What advice did your parents give on your career?

In the beginning, the job that Hillary does basically didn’t exist at the time, so when her parents found out they were concerned. Her niche, copywriting in the online business space, was relatively new having only been around for 5 years (at the time).

When she graduated from Miami, Hillary was able to get a PR internship in the city, while she was working on her copywriting business. During that time she would give in to mediocre work while spending most of her energy during work hours on growing her business, which eventually led to Hillary being fired. She can still remember calling her parents to let them know she was going all-in on her copywriting business.

While they didn’t stop her, they didn’t exactly have complete faith in her vision and wouldn’t support her financially. However, they were even more shocked when she decided to move to New York a year later, and prompted her to get a real job while working on business at the side. And of course, Hillary referred, she loved what she was doing and wouldn’t get a position that paid her as much as she was making at the time.

Now one of Hillary’s core personality traits is pursuing what she wants and figuring the details along the way, because of that they trusted Hillary to eventually figure it out, but never thought she’d be that successful that quick. This was before there was a huge library of free available courses, so Hillary developed that muscle memory for trying and experimenting her way through things, and she’s grateful for that.

What is the mental model behind: Using Brazen Ideas to Captivate the World?

A lot of what Hillary does in creative direction and positioning is taking entrepreneurs and creatives through the process of self-reflection deep enough so they can realize not just what they do so well but why. What they are bringing from their life experiences to the table makes them so unique. To explain Hillary uses an old quote:

“Your business is what you do, your brand is who you are.”

When it comes to using brazen ideas and using them to captivate our audience, Hillary uses the metaphor of an elevator:

You have in the branding world a standard response on what they do – help clients align with their values and create really cool content, find their voice, and show up online.

But Hillary uses the elevator metaphor to take her clients one floor down – find the why behind the goal and building from that. She helps people dig under the layers to find what is so exceptional about them, and part of that journey is the speciality, audience, and other foundational information, but she also talks about the framework. To do this, Hillary walks them through an exercise; let’s say you’re a copywriter and you take your client through a series of steps, what are they, and why are you doing them?

Hillary explains that often when you’re ready to take a creative direction, rebrand, and positioning, you know there’s something you do well, but you can’t put your finger on it. Therefore, that exercise helps you find that gold nugget of a concept or idea that you can turn into a framework, workshops, programs, etc.

“Every single person has this golden thread within them, and it’s such a joy to help people dig it out. It’s a point of view, a perspective, a philosophy, a way of doing things that is so powerful and unmistakable it makes them a magnet for their perfect people.”

Common factors between Hillary’s more successful clients

When it comes to building a business, building a following, and a platform, Hillary explains that what’s really important is consistency and focus, usually on one or two things to start with. For example, if you want to build a following between Instagram and LinkedIn, pick one and go hard on that platform, before moving to the next.

“Don’t be average at a dozen things, be extraordinary at one.”

What Hillary finds clients get lost in the process is when they focus on multiple points at once, before they get overwhelmed, ultimately burnout and backout discouraged and back to square one. There’s a lot to be said for focus and most importantly depth, depth of exploring ideas, focus, and deepening your approach to a single platform and sharing of a single idea, is going to help figure out your point of value and recognition.

“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 going to get lost.”

Having a clear focal point, conviction, and position that’s built on who you are, what you value, and do really well, you can’t help but attract people towards you.

How do you break people out of their bias towards authority?

Hillary states that imitation (looking at the most successful person and following their pathing) is a really good starting point, especially when you’re trying something brand new. But this is also where a lot of people get frustrated and bored because, as Hillary explains it, they are wearing an outfit that was not made for them.

When it comes to breaking her clients out of that cycle and making people see that they have something unique to the table, Hilary explains that often it is as simple as a matter of confidence. Going back to the elevator metaphor, this is going a step lower; Hillary believes that people get tied up in knots about the norms and sense of belonging, but it’s that process of self-examination where either the awakening happens or the business plateaus collapses. A big part of it is understanding and accepting when you’re imitating because you’re new, then making that decision to pursue exactly what you want and who you are.

On another note, some people believe they found the key. To this Hillary states that it’s easy to get caught up in the superficial nature of it if you are not willing to do the deep work.

Hillary has an opt-in known as the ‘Statement Piece Framework’ it’s a concept tool, where she’s almost forcing people to do something she believes many entrepreneurs don’t do today – examine their own thoughts. She explains that in the online world where all people know of you is a digital face, it’s easy to play it safe and show a side of authority. But with the framework, Hillary is forcing people to look at the 3 statement piece scenarios:

  1. Conversations with colleagues
  2. Conversations with clients
  3. Conversations with yourself

There are 2 categories in these conversations: advocate and anti. For example, in a conversation with a college, you have two responses:

  • “If nobody says that to me again, it will be too soon”
  • “I’m so excited about this breakthrough”

The first is an anti conversation, and the second is an advocate conversation. These points of view while you examine your ideas, what you don’t like is a much more valuable point to start at, than what you do or think is cool. To Hillary, it’s interesting to watch business owners dig into and notice their own thoughts and realizing their valuable for content and come up with original ideas; but also seeing examine what they don’t like, and figure out why they’re more excited to write about what they don’t approve of.

Hillary explains that the gravity of displeasing people on the internet is not what we think it is, or what we let it be. When we think about the creative confidence, that willingness to go and say the unpopular thing (a content strategy that Hillary has used for a long time), it’s about 2 things:

  1. You just have to start, and when you realize that one or two comments aren’t going to kill you, you have a lot more confidence to move forward.
  2. Check-in with yourself, how much conviction do you have on your own ideas?

Hillary believes when you’re confident in what you’re saying, you’ve taken time to develop the idea and really understand it, you can roll with disagreement a little more. But it’s also important. that if you are going to write something polarising ideas to also focus on empathy as well – if you’re going to talk about the other side it’s not helpful to attack an individual, instead of attack the system or the way of thinking, but also acknowledge that you understand why people think that way. She explains that it helps address any negative feedback you get and makes you more comfortable.

How do you maintain the idea of polarising without going over the line?

Hillary explains that this is a rep situation, you’ve got to push the line to know where it is. However, she states that it’s also really about being deeply connected to your values. If you have that consistency of approaching things with empathy and trying to explain your side while acknowledging the other side. If you come from that angle of self-awareness, Hillary says that most of the time you’re going to be okay.

Where you run into challenges, is when something inconsistent about your brand comes into the picture. For example, let’s say an influencer is all about female empowerment, and you find out they are a vocal trump supporter, that’s a surprise that can create huge waves. But if you are a wellness influencer who decides to write a book about anti-diet culture, from a place of not only compassion but also what to do instead; Hillary states that that approach is polarizing content that can actually help people.

“The bigger and bigger you get the more important it is to stay connected to your values, even if those change.”

Hillary’s Thoughts on Being Unmistakable

Hillary believes that it comes down to 2 things: Courage and conviction. You’ve got to find that nugget and hold on to it. Of course, that can evolve and shift, but having that conviction in who you are and what you do, along with that bravery to show up as you with your values without turning the volume down, is what makes people unmissable, unmistakable, and irresistible to the people that need to be in that energy.

Connect with Hillary:

Website –

Instagram – @hcweiss

Twitter – @hcweiss


You may also like