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Kendall Cherry of The Candid Collective: “Bring others along with you”

Bring others along with you. Change is only as strong as the community you bring with you. Don’t forget that for change to really take place, it requires people, hands, hearts, to make it a reality. And I’m not talking vanity metrics like Instagram followers, but advocates and people who understand your visions and will tell […]

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Bring others along with you.

Change is only as strong as the community you bring with you. Don’t forget that for change to really take place, it requires people, hands, hearts, to make it a reality. And I’m not talking vanity metrics like Instagram followers, but advocates and people who understand your visions and will tell their story alongside yours.

Sometimes, the story means more than the money.

For the longest time, I tried to tell this wonky version of my own story in order to try and make more sales and land more clients. But it wasn’t until I sort of let go of that completely, and just started sharing my candid thoughts on what was happening in my life, that things really started to take off. It took leaning in to my story to really make our business run. It’s a very different approach than the typical sales and marketing strategies other people tend to use, that’s for sure.


As part of our series about young people who are making an important social impact, I had the pleasure of interviewing Kendall Cherry, founder and creative director of The Candid Collective, an online and in-person community for entrepreneurs to come as you are, regardless of gender, age, race, revenue, or years in business. She’s on a mission to create a world that’s more candid and kind, and is based in Austin, Texas.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit. Can you tell us about how you grew up?

I come from a blue collar family — my dad was a firefighter and my mom was a preschool teacher. I didn’t come from one of those households where my parent’s were entrepreneurs, and our experience was that we were able to afford things because my parents were trading time for money.

My dad would work overtime a lot at the fire station, and would take up little side jobs at the fire department, teaching at the fire academy and drawing maps for the stations to use. We were your pretty typical middle class American family, and I definitely never thought I would have started my own business at that time.

I always thought I was supposed to do the typical career path: go to college, get a job, climb the ladder for 40 years, retire. I was the first person in my family to go white collar, so I remember it was like this BIG thing. But when I really got into it and I started to understand what that looks like, I realized that wasn’t what I wanted. I spent a little over 5 years in corporate America before I started my business and took a different path.

Is there a particular book or organization that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I still remember reading Savage Inequalities by Jonathan Kozol, on the bus to get to my classes in college. The main argument is about how the American education system has failed so many because of the difference in quality of education between rich and poor communities in the United States. It totally rocked my world. I remember this one day in particular, I was standing and reading, hand on the handle strap, looking out the bus window and just thinking “I’ve got to help however I can.”

There’s so much work to be done in this area, but I think this book really solidified for me that it shouldn’t matter what zip code you were born into, what your family structure looked like. Education is a basic human right, but that it doesn’t always look like a college education. I think good ideas can come from anywhere, and I want to build a space for those ideas to be built into businesses that change the world. No matter what your background is.

You are currently leading an organization that is helping to make a positive social impact. Can you tell us a little about what you and your organization are trying to create in our world today?

In it’s highest form, The Candid Collective is here to create a world that’s more candid and kind. But to do that, we are a community for entrepreneurs from any social background. We believe that there is a seat at our table for everyone, regardless of age, gender, race, revenue, or years in business.

There are so many things that hold people back from entrepreneurship, and so I wanted to create a hub for people to tinker with their business ideas — a place where you can learn from anyone. Where old dogs can learn old tricks, and where new dogs can learn old tricks.

Can you tell us the backstory about what originally inspired you to feel passionate about this cause and to do something about it?

A lot of the early inspiration for The Candid Collective comes from my own story. I was this liberal arts major who’d truly gotten a lucky break. My first job out of college was in the C-Suite, helping to facilitate employee engagement programs for our department. It was this unicorn of a job opportunity, and I really did have the perfect corporate life.

But I was so unhappy. The more years that I spent there, the less I felt like myself. I’d started toying with the idea of starting a business, but that wasn’t something that girls like me did. And so when I finally decided to start out on my entrepreneurial journey, there was no place I could go, no community that existed, for corporate dropouts turned entrepreneurs.

I was constantly being told that I was “crazy for leaving your corporate salary,” or that this was just going to be an expensive hobby. And I realized, that for people who choose a different path like I did, there really isn’t a safe space where they can go and leave the negativity at the door. It’s a totally different experience when you’ve got years of corporate conditioning to leave behind when you start your own business, so I decided to build the community myself.

Can you share the most interesting story that happened to you since you began leading your company or organization?

I think when I first started, I thought i needed to be the Instagram goddess or queen of social media marketing, but I realized that isn’t who I am or what I want to do. I just wanted to create a platform to share my story, and for other people to share theirs, too. I definitely leaned more into our podcast called The Candid Kendall Podcast than some of my early coaches and mentors advised. But it always felt like the right move for me.

What I’ve found in being authentic to myself and my own experience is that ˆstorytelling is what I do best, and also how I can help the most people. At the end of the day, The Candid Collective is really a community where every story matters.

Can you tell us a story about a particular individual who was impacted or helped by your cause?

I’ve got to brag about one of my clients, Tiffany Hsiang (@workingwithtiff on Instagram), who’s one of the most talented and thoughtful designers I’ve seen in the online space. When we first started working together, she was super shy and scared to talk on video and share her story on social media. But the more I started asking questions and exploring why she is the way she is, we sort of uncovered this hidden talent of hers.

She has this incredible way of explaining WHY big brands make the design decisions they do, but puts it into layman’s terms. She isn’t a snobby designer, but really takes her clients through the process and explains things in a way that’s easy to understand. She’s started teaching (with video!) through her Instagram channel, and it’s like watching a flower bloom. It’s just incredible to get to witness someone grow in confidence and tell their story. It’s my favorite thing about what I do.

How do you define “Making A Difference”? Can you explain what you mean or give an example?

To me, I think “Making a Difference” is helping people find exactly who they are. I think there are so many things that influence us and teach us that we can’t go after our daydreams. There’s just so much pressure to be something you’re not. I think the core of making a difference is reminding people that they are allowed to have preferences, to say “no,” and stand up for themselves. Life’s too short to be something you’re not.

Many young people would not know what steps to take to start to create the change they want to see. But you did. What are some of the steps you took to get your project started? Can you share the top 5 things you need to know to become a changemaker? Please tell us a story or example for each.

  1. You need unshakeable courage.

A lot of the time, being a changemaker means going against the grain and doing something where you are alone in your thoughts or thinking. You’ve got to know that what you’re doing is worth it, but most of the time we never actually know if there’s a payoff. It takes an insane amount of courage to be able to push forward, even when you can’t see every single step on the path to get there yet.

2. Bring others along with you.

Change is only as strong as the community you bring with you. Don’t forget that for change to really take place, it requires people, hands, hearts, to make it a reality. And I’m not talking vanity metrics like Instagram followers, but advocates and people who understand your visions and will tell their story alongside yours.

3. Sometimes, the story means more than the money.

For the longest time, I tried to tell this wonky version of my own story in order to try and make more sales and land more clients. But it wasn’t until I sort of let go of that completely, and just started sharing my candid thoughts on what was happening in my life, that things really started to take off. It took leaning in to my story to really make our business run. It’s a very different approach than the typical sales and marketing strategies other people tend to use, that’s for sure.

4. Think big, then dream even bigger.

I think to be a changemaker, you have to be willing to get really altruistic with the work and what you do. For The Candid Collective, we aren’t focusing on a certain market or location. For us, when we say we see a world that’s “candid and kind,” it would be easy to limit it to just women, or just people who live in Austin, Texas. But our movement is so much bigger than that. When I first envisioned The Candid Collective, I had to force myself to go beyond the small impact I thought I was capable of, and dream even bigger.

5. Use a wide lens when analyzing your current success.

There are a LOT of ups and downs when it comes to entrepreneurship. I think sometimes we get stuck in looking at how the day or week went, maybe sometimes even the month. When really, I think we need to take a wider look. What success happened this last quarter? Where am I at in comparison to last year? That’s where you can really start to see compounded growth.

What are the values that drive your work?

Collaboration is huge for me. I think that a lot of times people expect consultants or coaches to just sort of “tell me what you know.” But I think the learning process is a lot more two-sided than that. I’ve noticed that among my clients and even my friends that collaboration is a huge, unspoken part of our dynamic.

Many people struggle to find what their purpose is and how to stay true to what they believe in. What are some tools or daily practices that have helped you to stay grounded and centred in who you are, your purpose, and focused on achieving your vision?

I read for 30 minutes, every single morning, with a cup of coffee (and if I’m really on top of things, 30 minutes before I go to bed). It’s how I’ve tricked my brain into learning when it’s time to “turn on” and “turn off,” almost like the bookends of my day. Some of my best ideas happen while I’m reading in the morning, so I’ve really started to lean in to that time more.

In my work, I aim to challenge us all right now to take back our human story and co-create a vision for a world that works for all. I believe youth should have agency over their own future. Can you please share your vision for a world you want to see? I’d love to have you describe what it looks like and feels like. As you know, the more we can imagine it, the better we can manifest it!

I picture this world where a 40 year old veteran who’s looking to reintegrate back into society can be seated at a table next to a college drop out next to a single, late 20s, black female founder — the common thread among them is that they’ve chosen entrepreneurship. I want to see a world where there are educational resources available so that people who have their own vision, and idea for the future, can have a place they can actually GO to work on it.

And where those ideas (and people) aren’t discriminated against. Instead, there’s this communal collective of people who are looking to use their business ideas to improve the world.

We are powerful co-creators and our minds and intentions create our reality. If you had limitless resources at your disposal, what specific steps would take to bring your vision to fruition?

I would offer paid apprenticeships at my company (and at our co-working space, because it’s already built, because unlimited resources). I want to give people actual, tangible business experience before they go off and try entrepreneurship on their own. And offer scholarships to anyone who can’t afford our services or education outright. To me, that’s walking the walk.

I’d also like to bring events to our offerings, for people visiting Austin or even our local community. Where, if you’re a solo traveler, you’ve got somewhere to hangout, but also, if you live locally, you can swing by, too. I think the community aspect, just somewhere you can show up and come as you are, is the key to our success. I’d build in a LOT of events (virtual an in-person) that would make that come to life.

I see a world driven by the power of love, not fear. Where human beings treat each other with humanity. Where compassion, kindness and generosity of spirit are characteristics we teach in schools and strive to embody in all we do. What changes would you like to see in the educational system? Can you explain or give an example?

I would want to see more available space for students to tinker with ideas, to actively fail and try again, without moving on to the next unit or grade level. I think one of the biggest challenges with entrepreneurship has been deconditioning myself from this very linear, deadline driven learning cycle that I’m used to.

In the educational system today, you have 1–3 ideas, choose one, build it, move on. There’s no such thing as prototyping, or sticking with something, integrating feedback, and trying it again. I think that’s been the hardest part of starting a business, and I wish the educational space were set up more for that kind of learning.

If you could tell other young people one thing about why they should consider making a positive impact on our environment or society, like you, what would you tell them?

I think everyone has something they can do to impact the world around them, even if it feels incredible small. A lot of times, we like to think that we can only make a difference if it looks like impacting people by the thousands. I truly believe it’s okay to think smaller when it comes to impact. We need people who can go deep on an issue, just as much as we need people who can go wide and help the thousands. Don’t underestimate the power of helping one person or project in a REALLY BIG way.

Is there a person in the world with whom you would like to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them. 🙂

If I could meet Jenna Rainey, that would make my business soul so happy. I’ve followed her for years when I first learned how to paint with watercolors, but have stuck around as I’ve started a business. She is totally approachable, and doesn’t follow a lot of the flashy trends you can see in the online coaching space. I’d love to learn more about how she navigates it all.

How can our readers further follow your work online?

You can find us online at The Candid Collective or check out The Candid Kendall Podcast on Apple Podcasts or Spotify.

This was very meaningful, thank you so much. We wish you only continued success on your great work!


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