Hey Reader,

This is part 2 of my origin story as an entrepreneur and how I became a Solo CEO, teaching others how to navigate that journey. If you haven’t read part 1, go here to read all about where that call to entrepreneurship came from in the first place.

It wasn’t just my first client that came surprisingly easily. Over the next 6 months, my business grew rapidly. I’m not saying it was all easy or that I knew what I was doing (it wasn’t, and I didn’t), but pretty quickly, I was earning 2.5x my previous corporate salary, and I was drowning in work.

So, I took everyone’s advice and hired my first employee.

I decided to hire a bright, hard-working passionate woman that I knew personally. She had almost no experience in marketing, but I knew I could train her to greatness.

Don’t get me wrong. My new hire, Tanya, was truly smart as a whip, but I was drowning in client work, had no repeatable processes, and had built a business that relied on my active involvement in every aspect of client delivery, which left no time for training and no systems or defined processes for me to even teach her.

Still, though, we limped along and continued to grow.

Tanya helped where she coul,d and I kept getting better at moving quickly and keeping the ever-increasing balls I was juggling in the air.

A few months later, I made a change.

Through my We-Work office, I had become friends with a pair of entrepreneurial brothers. They focused on the same target market, early-stage B2B SaaS, and had a complementary business—outsourced sales development and deal closing. Plus, they were hilarious.

The older brother especially became a super close friend and an ally, referring business to each other and serving as mutual sounding boards and supporters.

A Proposal

Eventually, the brothers came to me with a proposal. They wanted to combine our businesses and join forces so we could grow faster. And they wanted me to be the CEO.

Throughout 2018, I had been working to build my personal brand on LinkedIn and in our industry, recording video content, speaking at events, and networking my ass off. They knew that with my growing reputation online and with key strategic connections in tech, I was in a killer position to grow our business.

It didn’t take me very long to get excited about the opportunity and agree to move forward. We jumped right in.

At that point, in terms of revenue, our businesses were about the same size, each bringing in roughly $30k a month. So they proposed combining them under a new brand with each of us getting a 1/3 split.

I knew that wasn’t quite fair. I was bringing in half the revenue (and clients), and had a bigger, better established personal brand, so I should be getting at least a 50% share. But I felt so good about the partnership and these friends of mine that I shrugged it off, sure that it would all work out in the end.

Narrator: it would not.

The New Company

We launched the new brand and I quickly got to work. Within about 6 months, I’d brought in a bunch of new business, scaling us to $98k in MRR despite losing a few of their initial clients along the way.

We continued to build out our team, and things looked really freaking good.

So good that when a mutual mentor of ours reached out about a VP of Customer Success, he knew wanted to leave corporate and start her own thing, he asked if I’d take a meeting with her and give her some advice.

We had an amazing conversation, and soon, we were negotiating to add her to the business as a full partner.

I’m honestly not totally sure how it all played over the next few weeks, but things moved quickly.

The younger brother and I were having some challenges. He would make unilateral and expensive decisions (like giving his entire team a raise) without discussing it.

And then, when I wanted to invest in my team’s growth, he’d veto it…despite my ability to prove that my team’s work was more profitable and floating the whole company.

But suddenly, I could sense a rift in our little team.

The other 3 came to me explaining their dissatisfaction in my leadership style, insisting that I step back from the CEO role and allow all decisions to be made by committee. At first, I agreed. I didn’t want to crater the business. I trusted these 3 and thought they must be right.

• Maybe I was difficult to work with.
• Maybe I didn’t deserve to be the team’s CEO.
• Maybe the business suffered under my leadership.

But the more reflected on it, the more I realized that it just didn’t feel right to me. I still wanted to be friends, partners, and allies. But I also wanted to be in charge of how my business operated.

So we had another meeting and I proposed that my team go back to being its own business. A Better Jones would split off, keep our clients, and remain strategic partners of the other three.

• We all agreed.
• We hugged it out.
• And we swore we’d remain friends.

Fewer than 24 hours later, they removed my access from my email and all company tools, materials, and documents. And then, they quickly began calling my clients to tell them that I had been the marketing leader in name only, and the younger brother had actually been developing the strategy and running the team.

​

Oh shit!

I won’t go into all the details. Partly because legally I can’t, but mostly because it got ugly.

I spent the end of March and the beginning of April 2019 battling constant panic attacks, trying to protect my team, keep my clients, prepare for litigation, and still deliver on big projects for my clients.

I kept every client. Every team member. And every dollar of revenue.

But still, it royally sucked. Truly…I think that month took 5 years off my life. It was harder to deal with than my divorce.

Survival

I felt like I only had one choice. I needed to do everything I could to keep my business afloat. So I just worked my freaking ass off to do that.

At no point did I ask myself—is this what I want?

Over the next 9 months, I grew my business all over again. New clients, new team members, new projects.

By early 2020, we’d hit $50k in MRR with our scrappy little team of 4.

But the wheels were starting to fall off. As we’d grown, we’d had to shift the types of clients we served and projects we took on. Instead of working closely with founders on innovative demand-generation strategies, we were doing more low-level execution.

• Writing blog posts
• Creating content campaigns
• Hosting lead generating webinars

My passion for the work was waning. My teams' skills were getting tested. And the clients we worked with were a lot more likely to get pissed off and show it.

Then, in February, as I walked out of a coffee meeting with a prospect to meet up with my boyfriend (now husband), Andy, I told him I felt…off.

I couldn’t put my finger on it, but I felt sort of woozy. Not like myself.

The next morning, when I woke up, I remember looking at the light in the ceiling above my bed and realizing that I could focus on it. It would quickly move to the right and then circle back if I looked at it. While my head pounded in the background.

I went to urgent care. And they quickly sent me to another office for a CT Scan to check for a brain tumor. It wasn’t a brain tumor, but a viral ear infection. They gave me a prescription of valium to help lessen the symptoms and told me to rest.

I laughed. “Rest? I’ve got no time for that,” I thought and went to the office.

This Is Burnout

At that point, I already had a long history of strange health issues — Hashimoto’s (auto-immune thyroid), chronic Lyme disease, and reactivated Epstein Barr Virus (the virus that gives you mono).

So, I did what I always do. I booked an appointment with my naturopath to see what she suggested.

A week later, as I sat in her office, my head still swimming and my eyes still struggling to focus, she asked me, “Why now?”

I looked at her, confused. “What do you mean why now? It’s an ear infection.”

“Kasey, this is stress. Why now? What’s going on?”

And without thinking or missing a beat, I immediately burst into tears and exclaimed, “I hate my job!”

That night, I remember sitting in bed, with my journal on my lap, thinking about my business.

I reflected on where I was and how I’d gotten there, realizing that I’d built a business doing all the things I hated about marketing—ongoing execution, little tactical outputs, managing my own young and inexperienced team, and working with bigger, better-funded startups and their marketing teams.

And had gotten away from everything I had loved about my work—big picture strategy and innovation and working directly with founders.

And I asked myself. “What if I did something else? What would I do?”

I wasn’t even sure if that was possible. But I knew I needed to try.

Less than a month later, the United States fully shut down because of COVID. I could have used it as a catalyst to transform my business, but I’m not sure I was ready yet. Turns out change is really freaking hard.

Thanks for reading my story. Or this part of it, anyway.

In the next issue of my Origin Story, I’ll be sharing how the most terrifying experience of my life became one of its greatest blessings, how I rode the feast-or-famine rollercoaster, and what I did to hit the reset button on my entrepreneurship.

In love and growth,
Kasey

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Ready to evolve from solopreneur to Solo CEO?

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