On this week’s episode of Messy in the Middle, I was fortunate enough to chat with Kendall Cherry! Kendall is the Founder & Creative Director at The Candid Collective, the authentic content and copywriting studio, helping rebellious types connect with their people and make more sales with authentic content. Here’s “Scaling While Staying Candid and Kind with Kendall Cherry!”
Here’s a little more on Kendall and her biz:
Kendall started out her professional career with a liberal arts education and communications degree. She worked in corporate communications right out of college and worked there for about 5 ½ years. There, she worked with her boss and team on employee engagement, events, and worked towards making others within the company feel seen & heard.
It was a bit of a fluke of a first job! Through a series of great promotions and opportunities, she went on to become the global head of training for IT implementation, changing the IT backend of a major company. She said she knew nothing, but was able to grow because she could communicate so well.
Something that served her really well in this environment was her no bullshit style. People would go to her to hear the truth! All the while, she felt like something was missing. She had always had dreams of entrepreneurship, but didn’t feel like someone like her couldn’t give up a 6-figure salary for a “pipe dream.”
Eventually, in 2019 she said “fuck it” and started her first business! She thought coaching was going to be the way to go. For a year after that “fuck it” moment, she built a side hustle, and it took about 6 months for her to sign her first client (2020 was looming and things were kind of a mess). Ultimately, she wanted to help people bust out of the corporate space instead of going into career coaching.
Copywriting
Now, copywriting is one of the many things Kendall and her team do for clients! Prior to starting her copywriting service, many people came into her online space because they followed her writing and storytelling. Once she started offering copywriting services, people wanted in! In the early stages of her business, she was constantly scaling up and down to figure out what worked.
As she was building a team, she was consistently weighing her own capacity for writing and the writing load itself. She came to learn that just because she could do the writing didn’t mean she had to be the one to do it. She’s always assessing the role she wants to play within her business and what that looks like.
In hiring other people, Kendall noted that she has learned how to let others have their own process and not base her hiring on a person’s process. It’s all about finding the right “who” to get it done, not the “right” process
Training Her Team
Kendall’s approach to training writers in her business is very unique. She has an apprenticeship program for freelance writers! Because she started out as a freelance writer herself, she knew the industry had a lack of mentorship.
Typically, 1 of 3 types of writers come to her interested in the program: someone who writes for a more dry market and is looking for a little more creativity, someone who is a general freelancer, or someone who is already a copywriter who wants to work with higher level clients but doesn’t yet have the client list to do so.
Through the program, Kendall and her team are able to train people using their client base. Her main goal is to give aspiring writers a great education and financial freedom. Something that she prides herself on in her teaching is leaning into how YOU sound rather than adapting to how others in the market sound. That way, you’ll definitely find the people who resonate with you.
Online Biz Culture
Between the two of us, Kendall and I had some very hot takes about online business culture. Kendall noted that she often toes the line of wanting to actually be in the online business space. One thing that she feels does not get talked about enough is the emotional burden of entrepreneurship.
As a single woman without a significant other to depend on for emotional (or financial) support, she often feels like she carries a silent burden. Without a financial crutch to lean on should she need, there are times when the pressure of solving for cash flow, paying her team, or even paying herself can feel crippling. She wishes she were able to invest more, and that there was someone like her in the online space to look to as an expander.
Diversity in the Online Biz Space
Building a diverse business is something that is very important to Kendall that she feels a lot of other online business owners miss the mark on. Recently, she noted she saw imaging from a large online business having a brainstorming round table and nearly everyone appeared to be white.
As a business with a team that is about 50% BIPOC and has a very diverse client base, it’s important to Kendall to continue to be loud about other entrepreneurs doing the work that comes with diversity. To her, the work involves putting your money (the money you’re spending and receiving) where your mouth is.
It is her dream to open a coworking space in Austin, Texas where she lives where a black female founder of a business and a trans person can sit next to each other and receive that same kind of support.
When it comes to hiring a diverse team, it shouldn’t feel prescriptive, we should be hiring talent for talent. What it comes down to is your pipeline and how you are finding your people.
Email Marketing
Kendall’s resource “What the Fuck to Send to Your Tiny Ass Email List” is one of my favorite things on the internet, for obvious reasons. In talking about email marketing, she debunked the idea that you have to have a huge email list to make money from email marketing.
What is more important than the quantity of subscribers on your list is the quality of subscribers. You need to have the right people on your list! Email marketing is all about the long game, so it’s important not to bust out of the gate with your sales pitch. Leading with a sales pitch is a sure fire way to turn people away from your list. You should lead with quality and original content to nurture your “quality” people.
Resources and Next Steps
If you’re looking to get started with your email marketing, definitely check out “What the Fuck to Send to Your Tiny Ass Email List!” You’ll really love this free guide of 52 prompts as a great starting point. Kendall is currently working on an email course to launch sometime in 2023, or you can reach out for an email strategy session with her and her team!
