From Accidental Entrepreneur to Agency Founder
In this episode of Client Horror Stories, Beth Trejo shares a different kind of horror story—not one involving a difficult client, but a challenging business partnership that tested her leadership, resilience, and sense of self.
Beth explains how she never intended to become an entrepreneur. While working in marketing and community development in Sioux City, Iowa, she noticed local businesses struggling with recruitment and promotion. Encouraged by friends and inspired by other young entrepreneurs around her, she launched Chatterkick, a social media agency, armed with little more than an $1,100 laptop and a willingness to learn on the fly.
The early days were anything but easy. Shortly after leaving her job to start the company, Beth discovered she was pregnant. Already raising a young child, she found herself building a business while navigating a high-risk pregnancy, hospital visits, and eventually time spent in the NICU with her newborn daughter. Despite the emotional and physical strain, she continued serving clients, hiring interns, and growing the agency through sheer determination and resourcefulness.
Building Momentum & Finding Success
As Chatterkick gained traction, Beth expanded the business and eventually bought out her original partner. The separation was amicable, allowing her to take full ownership of the company and continue scaling it independently.
Around this time, social media marketing was experiencing explosive growth. Larger organizations and investors began paying attention, and Chatterkick received multiple acquisition offers. Beth ultimately decided to sell the company—not because she wanted to walk away, but because she believed the partnership would provide the resources, infrastructure, and financial stability necessary to achieve greater growth without taking on overwhelming personal risk.
The acquiring organization was a diversified company with interests in agriculture, farming, and other traditional industries. Chatterkick represented a completely different kind of business within their portfolio. Initially, Beth saw advantages in the arrangement. The parent company could handle administrative responsibilities such as billing, HR, policies, and operational support, allowing her to focus on growth and client service. However, the reality proved more complicated.
When Cultures Collide
One of the first challenges Beth encountered was a dramatic culture mismatch.
Chatterkick was a modern, creative agency filled with young professionals who valued flexibility, collaboration, and an energetic workplace atmosphere. The acquiring company operated with a far more traditional mindset.
What appeared to be small differences at first soon revealed deeper incompatibilities. Company policies, dress code expectations, management philosophies, and workplace norms often clashed with the culture Beth had intentionally built. While Chatterkick employees worked in jeans and embraced a casual environment, the parent organization maintained much more conservative standards.
Although these tensions created frustration, they remained manageable because one key executive acted as a bridge between the two organizations. This individual understood both sides and helped shield Chatterkick from unnecessary interference, allowing the agency to preserve much of its identity.
Rapid Growth Creates New Problems
Despite cultural challenges, the company continued growing rapidly.Within a short period, Chatterkick expanded from a small team of only a few employees to roughly twenty-six people. Simultaneously, the company launched operations in Baton Rouge, Louisiana, while maintaining its headquarters in Iowa. This growth created entirely new challenges.
Beth suddenly found herself managing multiple offices, hiring salespeople, implementing systems, and developing leadership skills she had never previously needed. The business was scaling faster than its internal processes could keep up.
Compounding the difficulty was the geographical separation. Unlike today’s remote-first environment, managing distributed teams at that time required constant travel and communication hurdles. Beth often found herself participating in important meetings remotely through a laptop screen while attempting to oversee operations hundreds of miles away.
The company was expanding, but the pace of change left little room for stability.
The Turning Point: A New Leader Arrives
The true crisis emerged when the executive who had served as Chatterkick’s advocate left the organization after more than twenty years. His replacement immediately changed the dynamic. According to Beth, the new leader neither understood the business nor shared her vision for its future. More importantly, there was no trust between them.
While the previous executive understood enough about the social media and services industry to provide meaningful guidance, the new leader appeared to misunderstand the business at a fundamental level. Beth found herself repeatedly explaining basic concepts about how professional service firms operate.
The parent company began comparing Chatterkick’s growth expectations to software companies, despite the fact that the two business models were entirely different. Software companies can scale products infinitely, while service businesses rely heavily on human expertise, labor, and client relationships. For Beth, these conversations were alarming because they revealed a deeper issue: decision-makers were attempting to manage a business they did not truly understand.
A Fundamental Misunderstanding
As tensions increased, Beth spent more and more time educating stakeholders instead of building the company. She found herself defending basic operatial realities and correcting misconceptions about how the agency generated revenue, acquired clients, and delivered value.
The disconnect became increasingly frustrating. Rather than focusing on growth strategies, innovation, or client success, valuable energy was consumed by explaining why certain expectations were unrealistic. Beth began to realize that the parent company may have acquired Chatterkick because it appeared exciting and modern rather than because they genuinely understood its business model. Eventually, it became clear that the investors wanted an exit.
The Silent Battle
What followed was the most difficult chapter of the story.
The parent company began applying pressure for Beth to either repurchase the business or facilitate another sale. Instead of direct confrontation, much of the pressure came through subtle tactics designed to create urgency and anxiety. There were discussions about shutting down operations. Deadlines appeared unexpectedly. Threats were implied rather than explicitly stated.At the same time, Beth kept this struggle hidden from her employees. Her team continued showing up every day focused on serving clients and growing the company, unaware of the uncertainty unfolding behind closed doors. This created a profound emotional burden. Beth describes carrying immense fear privately while simultaneously projecting confidence and optimism publicly. She would finish a stressful negotiation call and then immediately join a team meeting, smiling as though everything was perfectly normal. That emotional balancing act became one of the hardest experiences of her career.
The Question That Changed Everything
During the chaos, Beth reached a critical moment of self-reflection. She stopped focusing on what investors wanted, what advisors wanted, or what others expected. Instead, she asked herself a simple but transformative question:
What do I actually want?
The answer wasn’t immediately obvious.
Beth recognized that she had spent much of her career prioritizing other people’s needs. As a self-described people pleaser, she excelled at customer service and relationship-building, but sometimes struggled to advocate for her own interests. After considerable reflection, she concluded that buying Chatterkick back could make sense—but only if it was treated as a sound investment rather than an emotional decision. She refused to buy back her job. She would only buy back the company if the numbers worked and if she genuinely believed she could restore its value. That shift in perspective changed everything.
Taking Back Control
Armed with clarity and confidence, Beth entered negotiations. She understood the company’s true market value and recognized that she held more leverage than the parent company realized. The business was struggling financially, and finding an outside buyer would be difficult. During a meeting at the parent company’s office, she calmly presented her case. She explained the valuation she believed was fair and outlined the terms she required. Then she did something many negotiators find difficult: She stopped talking. Beth allowed silence to do the work. Eventually, the other side agreed. The deal moved forward. After years of tension, uncertainty, and emotional exhaustion, Chatterkick was coming home.
Rebuilding & Moving Forward
The transition happened quickly. Within thirty days, Beth and her team had to rebuild critical business functions that had previously been handled by the parent organization. They established health insurance plans, recreated operational systems, implemented policies, and reorganized infrastructure. One unexpected benefit emerged during this process. A talented operations and finance professional from the parent company chose to join Chatterkick, bringing valuable expertise that complemented Beth’s strengths. Together, the team rebuilt the company from the ground up. Their collective effort transformed a moment of crisis into a new beginning. Since regaining ownership in 2018, Chatterkick has continued to grow and thrive.
The Ultimate Lesson: Trust Yourself
Although the story contains lessons about acquisitions, company culture, private equity, and negotiations, Beth believes the most important lesson was personal. The experience forced her to develop confidence in her own judgment. She learned to distinguish between decisions driven by fear and those grounded in conviction. She learned that clarity about what you want is one of the most valuable assets a leader can possess.
Ultimately, the story is not just about buying back a company. It is about reclaiming ownership of one’s vision, values, and future.As Beth reflects on the experience, the question that guided her through the crisis remains relevant today:
Do you trust yourself fully?
For entrepreneurs, leaders, and anyone facing difficult decisions, that may be the most important question of all.
