Josh Polsinelli's Relationship-Centered Approach to Acquisitions

How Josh Polsinelli’s Relationship-Centered Approach Led Him to Liberty Labels

Apr 11, 2025

Josh Polsinelli first encountered the world of acquisitions during an entrepreneurship class at UC Berkeley's Haas School of Business. "The idea of small business ownership and entrepreneurship stuck with me," Polsinelli recalls. He continued his interest and stayed alert of mergers and acquisitions throughout the years. However, with the second half of business school to finish and a young family taking shape, the timing wasn't ideal to pursue this interest. After being introduced to several small business owners, something clicked for Polsinelli and he decided to act on his entrepreneurial ambitions. These early connections provided the inspiration he needed to eventually make the leap from corporate life to business ownership.

Polsinelli's search for a small business acquisition began in 2022, starting off with an "all in" mentality. He described his approach as similar to transitioning from a couch potato to marathon training. However, leaving the corporate tech world to buy a small business proved to be more challenging than he had anticipated. "I had a lot to learn," he admitted, noting that he spoke with individuals involved in every aspect of the acquisition process to gain valuable insights.

Fortunately, he surrounded himself with a supportive community eager to share their knowledge with someone who was "humble and curious." Additionally, he found that podcasts, books, and social media played significant roles in his learning process.

Clear Goals and Objectives 

Crafting clear goals, objectives, and ideas of what you’re looking for in an acquisition is key to identifying early in your search. As PolsinelliPolisinelli pointed out, “Defining that criteria early on so that when you go out and have these conversations, they can be productive.” Set up conversations with people in your network, business bankers, representatives, brokers, and other business owners to help gain as much insight as possible. For Polsinelli, location was a key factor for his first acquisition. “I wanted to find something in the Kansas City area and had a good sense of the size of the business I was interested in.” However, he was more flexible regarding the type of business.

Conversations with other business owners proved essential to Polsinelli's search process. "The more of those conversations you have, particularly visiting businesses and talking with owners to understand their day-to-day operations, the better," Polsinelli explained. "Ask yourself: Can you see yourself in their shoes running that business? These discussions help you refine your criteria as you move forward in your search."

Polsinelli's search for a business became his full-time commitment, though balancing this with family responsibilities meant his time was precious. "While business brokers can connect you with motivated sellers who are ready to exit, I found the most promising opportunities came through networking and selectively reviewing broker-listed local businesses," said Polsinelli.

After conducting his own extensive search, Polsinelli was ready to commit to his first acquisition. He recommends looking at as many potential acquisition targets as possible. This isn't just a passing suggestion… It was a strategy he lived by, analyzing over 225 businesses before finding the right acquisition. Ultimately, his persistent and methodical search led him to Liberty Labels, a company based in Fort Scott, Kansas, that aligned with his vision and goals.

Polsinelli recognized that acquiring Liberty Labels was a smart move for him. The company was one of the few small businesses that experienced steady growth during COVID-19. Additionally, its long-term employees were highly valuable to the operation, and the business was able to function effectively with minimal involvement from the owner on a day-to-day basis.

The closing process was relatively smooth, as the owner was already interested in retiring and had previous experience with mergers and acquisitions, which helped navigate the process. There was a tense moment regarding a minor issue, but Polsinelli emphasized the importance of building trust with the owner in those situations: “That's when you cash in those trust chips and utilize them.”

Making the Transition

Establishing a successful transition was a priority for both Polsinelli and the previous owner. On his first day of ownership, Polsinelli was introduced to all the employees at Liberty Labels. He took the time to learn about their roles and how the team worked together. “It’s essential to understand what the employees do. I need to know the team, as I’ll rely on them,” Polsinelli remarked. The previous owner was also keen on ensuring that Liberty Labels thrived and that his employees flourished, so making a positive first impression was crucial for Polsinelli.

During the first six months, Polsinelli made only minor changes. "My role was to come in, be a sponge, and learn as much as I could while also gaining the trust of the team," Polsinelli recalls. One of the most significant changes he implemented was incorporating new accounting software and updating the inventory process, which streamlined the workflow from two days to a half day. Additionally, he introduced celebrating birthdays with favorite desserts and bringing in lunch for work anniversaries. Building relationships in those first few months was crucial for Polsinelli, particularly because strengthening connections was important to the previous owner, with whom he remained in communication.

By the one year mark, Polsinelli learned how to keep his head down and keep his feelings under control. "I think it's important to keep your emotions in check and try not to overreact to anything. I've learned there will be cycles - times when there's heavier order volume, activity, and quoting work, followed by periods when things slow down a bit. I think understanding these business rhythms just takes time."

Enhanced business development strategies have yielded significant results for Liberty Labels, securing six new clients during Polsinelli’s first year of ownership. He also implemented several strategic improvements that strengthened Liberty Labels’ professional image, including redesigned invoices, a modernized website, and branded merchandise for the team. Additionally, targeted SEO campaigns have increased online visibility, directly contributing to sales growth.

Over the next 3-5 years, Polsinelli plans to expand Liberty Labels through targeted investments in advanced technology and equipment. This growth initiative will not only broaden his customer base to include new market segments but also create enhanced career development opportunities for his team members. 

Polsinelli's story illustrates how diligent research, relationship building, and patience can facilitate a successful transition from corporate life to entrepreneurship. 

For more information on Liberty Labels visit their website or LinkedIn page.