We were lucky to catch up with Ashleigh Henry recently and have shared our conversation below.

Ashleigh , thanks for taking the time to share your stories with us today Folks often look at a successful business and imagine it was an overnight success, but from what we’ve seen this is often far from the truth. We’d love to hear your scaling up story – walk us through how you grew over time – what were some of the big things you had to do to grow and what was that scaling up journey like?

I’m truly enlivened by this topic because you’re absolutely correct — the media glosses over the messy middle with ease. It’s not the sexiest part to talk about and it surely holds the reins of resiliency or fragility. The middle is where entrepreneurs can either create an everlasting and timeless brand that purposefully changes the world by shifting society forward or not… because they’re not able to push through for reasons that only they know. Neither is right or wrong, but I definitely wish this question was a regular question instead of an outlier!

I started this brand 3 years ago and it started with me, myself, and I. I left a multi-million dollar startup during the pandemic when I realized, after letting go of seven of my team members in one day without prior knowledge that it was going to happen, that I could either build someone else’s brand or build my own. I knew, after being the Marketing Strategist for that company (moonlighting as Social Media Marketing Strategist, Employee Engagement Strategist, Coordinator, In-Person Events Rep, and Copywriter after we let go of seven team members), that I had plenty of grit, capability, strength, resiliency, and knowledge to enter into the world of entrepreneurship… again. The Cheetah Company is my third company — the first being a photography business for a decade, the second being a product business — and it’s been my favorite brand to create thus far because it combines so many of my loves and passions, but it’s also shifted and changed 100+ modern businesswomen around the globe through our female-led team.

The beginning of this brand is similar to many others: a bit of a waltz between hustle and burnout. I created a machine that needed a lot of me all of the time. I started The Cheetah Company (originally penned under my name) and I was running it from a personal brand aspect, while it was quickly scaling into a social media and lead generation agency for modern businesswomen. Once we hit our first few multi-five figure revenue months, I knew it was time to hire or I was going to have fire myself from this intense job I was creating for myself. We brought on a few contractors and quickly grew, at one point, to ten contractors.

When I realized what I was building and how it was feeling, I knew I had to give myself a runway to get out of it. The agency was incredible and we achieved incredible results for our clients. From sold-out in-person events post-pandemic that ranged from 20 people to 300,000 people, bringing in revenue alongside our clients from $200-400k… to our clients landing their first clients and beginning their timeless brands… I knew we were well-equipped to help modern businesswomen, but the container and the experience wasn’t quite right.

We pivoted, slowly and sustainably, into consulting, coaching, and education to illuminate how we could serve, while sunsetting our agency model.

I share the overview above because the full picture is needed here, but the ways we scaled and the strategies we used are so simple it hurts.

We cared about people and their problems more than anything else. As the CEO, I acted as the face and brought a personal brand aspect to the company, while creating relationships high and low, from first degree to third degree connections through my network while expanding our impact by delving into my network’s network’s network.

We kept an old-fashioned-roladex-style approach to marry a traditional and timeless approach with a modern twist. The modern twist occurred on social media, leveraging grassroots pr, and actively serving through educational value on the web, via our email list, through social media, and in speaking engagements across the nation. The approach was simple: a spreadsheet with the last connection date with the person on that line, their name, their digital presence (web, social, email), notes about their customer-journey, overall notes about them (leveraging something we teach called the FORD theory, to connect with people about their families, occupations, recreations, and dreams which is something I learned on the sales floor as a pre-selling agent for brands like Harley-Davidson, BMW, Suzuki, Kawasaki, Volkswagen, and others), and with notes about what we’re interested in serving them with (from our service suite that ranged from agency work to consulting and self-paced education). We leveraged that lead list like it was our little black book, consistently making connections, building everlasting relationships, and passionately serving each person to later welcome them into our services from connection to client.

When you focus on building an everlasting, timeless, and purpose-driven brand that invites others to join you in a mission to shift society forward… those folks come to you with ease. Though we were extremely proactive in the beginning — and still are — with building everlasting relationships, it’s our purpose and my personal story as a founder that regularly acts as a catalyst for clients to come into our cheetahlicious circle. We actively promote our desire to help women around the world resiliently rise in their power after walking through trauma and I regularly share my personal story of being a survivor of domestic violence and sexual assault to rally-call to women around the world to join us to shift their businesses forward while we support causes that matter to help other survivors.

Ashleigh , before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Before stepping into entrepreneurship I worked in higher education, corporate, startups, boutique management, events and hospitality. I was a busy bee, starting my first job at 15, and learning how to market and sell with service in-mind on the sales floor of a well-known shoe store with a microphone in-hand running urgency marketing to help our clientele in-store to purchase quickly and swiftly. While in high school and college for my journalism degree, I started exploring different jobs at a time — kind of foregoing the social life in college — to just experiment and see what I enjoyed the most.

After working with prestigious brands like Harley-Davidson, BMW, Suzuki, Kawasaki, and Volkswagen as a pre-selling agent, I realized I had a love for service, communication, marketing, sales, and… storytelling. Sales to me is like painting a story of opportunity for a customer to see a life they can experience post-problem. I was the editor of my college newspaper and creative literary magazine and learning those two modalities at once allowed for me to see the vibrancy of the creative world, while having margins and pragmatic measures to meet in the newspaper world.

I honestly thought I would pursue being an investigator journalist post-college, but marketing won my heart and I pursued it in every position I had after college.

From there, I realized how much I enjoyed all of the above and slowly started stepping towards the vision and creation of The Cheetah Company (starting first with freelancing before taking the leap and creating a runway to take a risk to create the company during the pandemic).

From creating a social media and lead generation agency that was thriving to shifting our business model to consulting, coaching, and education… it’s been such a blessing to see it all come to fruition to serve 100+ modern businesswomen around the globe with our brand!

The Cheetah Company’s mission is to holistically harmonize lives and businesses together, for the modern businesswomen to no longer have to choose between creating a life or a brand she loves… but having the freedom to do both in a harmonious way, without the suffering experience of trying to “balance” it all. We promote harmony over balance, always. Many of our clients joke that we’re both their business advisors and life advisors because we’re regularly asking them about their lives outside of work, if they’re actively creating holistic harmony throughout their life (from relationships to spirituality to health and wealth!)

We help women resiliently rise in their power to boldly create timeless and everlasting brands that outlive them. It’s our greatest honor to do this work! I’m most proud of the women that are bold enough to work with us; there’s a magnet between us and our absolute clients that are meant to be with us. We actively push them to build brands bigger than themselves and it’s work that’s not for the faint of heart. .

Can you share one of your favorite marketing or sales stories?

LOVE this question!

As aforementioned, I share my personal story with domestic violence and sexual assault throughout our brand when it feels right, when there’s a purpose to, and it acts as a through-thread to our mission (to help women resiliently rise in their power while having holistic harmony between their life and business to ensure that burnout stays far away from their lives!)

In 2022, I took a big risk on July 13th.

July 13th is the annual reminder of when I was sexually assaulted by a trusted individual from my college.

I had sketched an idea for a campaign called “Shine the Light” to share my personal story of resiliency and create awareness and purpose to that story. Shifting the narrative from this being something that defines me, to something that defines my movement in the world to create everlasting brands that dedicate and devote their time, energy, and dollars to movements that matter.

I asked our world-wide community to donate to the Ocala Domestic Violence and Sexual Assault Center in Ocala, Florida, after I shared my story… line by line via our social media presence.

We asked for donations to the center and our consulting firm then “donated” a consulting resource back, customized to each individual, to accelerate their business growth.

Over 30 women around the world — from America to Finland to England to South America — donated to the center.

I was nervous that morning. Like shaking in my boots kind of nervous because I wanted to ensure that my personal story didn’t act as shock-value marketing, but instead society-shifting marketing to actively create a catalyst from story to donation.

It’s one of my favorite things we’ve ever done and we have upcoming initiatives that will continue this mission!

Can you share a story from your journey that illustrates your resilience?

Absolutely.

In 2021, we were sustainably shifting our business model from agency to consulting, coaching, and edu. Our first edu product was two weeks from launch.

I received a call from my family that a family member had passed.

And then I received four more of those calls.

In the span of a handful of weeks, while shifting our business model, while managing a roster of 20+ clients with a national team of 10… I was losing family members left and right.

One of our most needed contractors was struggling in her personal life and had to leave her work during the midst of that launch… leaving our team with a ton of marketing assets to create a week out from launching our first edu product.

I was a mess, but I knew that the rest of the team was watching me to see how I would react to every problem.

I chose resiliency. I envisioned how I wanted our first product launch to go, I leaned into my mindset coaches (who all had a hand in trauma work and grief), leaned into my family quietly offline, and actively processed my grief while holding space for my joy, the possibility of this product launch, and I just marveled at human hope and what it can do even in tumultuous times.

We created the assets in record time.

We launched the product and welcomed in 30 members during that first launch.

We continued to shift the business model.

I grieved in the background, especially since it was still a time when funerals weren’t actively occurring.

We served our clientele & new members well.

And… I resiliently rose into my personal power to hold grief and joy all at once… an internal waltz between the two.

Contact Info:

• Website: www.thecheetahcompany.com
• Instagram: https://www.instagram.com/thecheetahcompany/
• Facebook: https://www.facebook.com/thecheetahcompany
• Linkedin: https://www.linkedin.com/in/ashleighchenry/
• Other: www.thecheetahcompany.com/blog

Image Credits
Corry Frazier Photography