The Leap: On Rejection and Leaning into Strengths with Kelly Bennett

Welcome to The Leap! For this IG Live series, Wethos CEO Rachel Renock sits down with entrepreneurs who took the leap toward working independently or starting their own project.

In this episode, Rachel sat down with Kelly Bennett, the founder and creative director of With Kelly Bennett. Based in New York City, Kelly has been building lifestyle brands since 2009. Kelly's written an award-winning lifestyle blog, was a creative director and partner of an award-winning vegan restaurant, and was previously a marketing director of an experimental city blog for creatives in downtown Las Vegas.

In 2021, Kelly decided to share their decade of experience and took the leap to launch an incubator for creatives who are building emerging lifestyle brands. Kelly also hosts a weekly podcast called Creative Direction with Kelly Bennett, answering questions from creatives who are building lifestyle brands. 

Watch the full interview here, listen on Spotify, or read below to learn more about Kelly’s path to being a creative director, handling rejection and self-doubt as a creative, and what led Kelly to launch an incubator for creatives.

Note: The following interview has been edited for clarity and length.

RR: Kelly, thank you for being here. I’d love to hear a little bit more about your journey to start on your own and how that business has evolved over time.

KB: Right from the beginning, you can tell I definitely did not take a linear path to becoming an entrepreneur. Even before 2009, I studied marketing and international business, and I literally traveled around the world trying to figure out how the hell to put all of my ideas and passions and skill set into a career. I knew I always wanted to build brands. I knew that I wanted to feel creative. I knew I wanted to work for myself. I knew I wanted to make some sort of impact in my own way. But I had no freaking idea how to put that all together.

Through college, that was my chance to get in and start testing and experimenting. And that was a whole thing because I got rejected from every college I applied to except for one community college that let everybody in. I just studied, studied, studied, and tried everything. 

And what I was honing in on was creative direction. That was like this really cool balance of business and creativity. In 2009, I graduated college and I was working for an ad agency and the conversation was, "Okay, brands are going to start coming online." At that time, it was Twitter. And, I was like, "Well, this is really cool." Because I always wanted to build this ecosystem of building the brands that really cared about people and wanted to align with people's ethics, morals, values. I also was really passionate about connecting consumers to those brands.

So that's when I got into social media and my first client right out of the gate was this international company, a huge hotel company in Las Vegas — I was living in Vegas at the time — and I got them on Twitter.

It was like one of the first really big international companies that went on Twitter. I literally met the marketing director at a mixer and she was like, "Do you think social media is going to be a thing?" And I'm like, "It's for sure going to be a thing." And she's like, "All right. I'm going to hire you to do it." I went home and I Googled how to start a brand on Twitter and I figured it out and it was really cool and that was the moment that I was like, "I got it. This is what I want to do, but I want to apply it to lifestyle brands." So, that was 2009. In 2022, I'm still doing it and just refining my process.

RR: Thank you so much for sharing that. I really appreciate the way that you are open about all the rejection that you faced. I'd love to talk a little bit more about how you overcome rejection — particularly in those moments where it just feels totally overwhelming or maybe hopeless. How do you move through those?

KB: I got to say, I was raised by Italian New Yorkers who really instilled this thing in me of like fuck it. Like, just do it and just keep going. Don't listen to [rejection]. 

But what I do now is get grounded with myself and start listening to myself again because when you start getting in the loop with rejection, sometimes that's when the self doubt comes in and then that's when you're like, "What the hell am I really doing with my life?"

[Rejection] can be a real whirlwind because when you're a creative, an entrepreneur, a small business owner, there's a lot on you. You're always thinking about the future, so it really could trip up your anxiety. For myself, I like to get grounded. I live in New York City, so I just take really long walks and I allow myself to listen to myself again. It's those little rituals that I have that just help me chill out a little bit — close up the laptop, get the hell off of social media, journal. Taking that breather, taking a shower, those things are really, really helpful so you can just hear yourself again.

RR: In terms of just staying a little bit more on this topic and being discouraged, I know that you mentioned a guidance counselor in high school sort of discouraging you from even applying to college. It's not easy to get rejected. It's not easy to be discouraged. And, it's particularly hard when it's coming from an authority figure when you're younger.

There are a lot of younger folks out there who I know are just starting their freelance businesses or maybe they're hustling on the side in college or even in high school. How do you find encouragement when you're faced with authority figures like that telling you it's never going to happen?

KB: Take note of who you're listening to. I am very, very intentional — even when I was younger — of who I surround myself with and who I allow myself to listen to. You know, there's times where it's really important to take pause when someone's like, "Hey, this isn't a good idea."

But in this context, as far as someone telling you it's not possible, I would also look at what their experiences were. Are they where you want to be? Probably not. It's really important to be really mindful of who you're listening to and that's why I'm so fricking passionate about re-releasing my new podcast and having my incubator and having a text community where people literally text me questions that I could help answer. I'm so passionate about that because I want to make sure that people have that support because I know for the longest time, I didn't and I just kind of had to figure it out. So I would say be really mindful of who you listen to.

RR: On your website you mention your own comprehensive disabilities, which I think is really important and it's something that a lot of creatives ask me about, managing my ADHD. My understanding is that you have dyslexia. I wanted to help everybody kind of understand what your disability is, how it does or doesn't interfere with your work, and any advice to other business owners who might be trying to manage similar disabilities.

KB: My workaround with that is leaning into what I am good at. If you put me in front of a room with a microphone or in a video or anywhere that I could just talk, I'm cool. If you needed me to write an essay about this topic, I would never hand it in. I've just learned how to really lean into my strengths and be okay that I can't do it all. I'm really honest with it now. 

I remember in the beginning when I had my blog, I used to send out email blasts because email marketing was like the really cool, hot thing. I used to write long emails and I would get emails back saying like, "Please stop writing these emails. Your writing is so bad." Which was fair. It wasn't good and I really have problems stringing together a sentence. But that was also a moment that I'm like, okay, let me make YouTube videos and make micro content, and that's how I became a content creator.

I always like to encourage creatives [to] lean into what you're good at. For people who are really great at writing, fantastic, have a written blog. Or, if you're really good at just talking but you don't want to be on camera, have a podcast. We have so many options right now and I think the pressure now versus then is doing everything. It's really important to be self-aware of what you like and what you feel creative in, because that's how you'll show up and be consistent.

RR: Your incubator looks really helpful. What led you to that? What topics do you cover in the program? What do you see people struggling with the most?

KB: In the tech space, there are a lot of incubators and accelerators. But if you're a creative, say, a maker or an artist — anything where you’re a team of one — there really isn't that much support. 

And I was like, "You know what? Let me just start my own [incubator].” It was really me going with that same spirit of fuck it, I'm going to make something that I feel like is really needed. I launched it last year and it went off. Like, it sold out.

What I cover is for creatives who are building lifestyle brands, either a personal brand, a consumer brand, product or service. It's for someone who's in the beginning stages, maybe like up to five years — I like to think of it as an emerging lifestyle brand. It takes you through the whole thing for yourself, the business side of your creativity, really understanding what is your craft? What's your method? How do you put the pieces together? What is unique about what you bring to the table? What's unique about what you bring to your industry? And really owning that. The coolest thing I hear from people is just feeling more confident in the space that they take up in their industry and in their own life.

We talk about the business side of your creativity, the intention behind the brand, brand identity, storytelling, your products, your product mix, understanding the systems of how your brand works, having that structure so you could sustainably build your business because especially if you're a team of one and a creative, having that structure is so fricking important.

RR: How do you think about personally defining success? What do you recommend for folks in terms of actually quantifying and measuring milestones or success?

KB: For myself, I'm a big, big, big, big passionate person when it comes to journaling. If you're a pen to paper person, turn off social media or whatever noise and allow yourself to just write down what you really want.

I also like to set quarterly goals — more than that to me feels a little too much. I like to think about what I want to do for the year and then break it up into four parts. For the creatives I work with, that really resonates too.

I do a lot of going in and then taking a step back to see the big picture, and having that as a curated experience during certain times is really helpful in the creative process. But again, going back to listening to yourself, I think that's the number one thing [when] defining success.