Craig Geisler: Leading the Debt Collection Industry with Fairness

Craig Geisler | Cherrywood Enterprises LLC: Leading the Debt Collection Industry | The Enterprise World

The debt collection business is not a modern phenomenon. People have continued to collect debt since ancient times, albeit with methods less sophisticated and evolved than today. While many still consider debt collection a business practice led by greed and fear, lawmakers around the globe are working to change such negative notions by introducing regulations and ensuring debtor safety and fair treatment.

In an industry riddled with years of negative connotations, one company that plays by the rules and stands out is- Cherrywood Enterprises, LLC. Leading the company at the top, Craig Geisler (CEO and President) has positioned it where Lenders and attorneys love working with it. 

A Small Beginning

After beginning as a small debt buyer, Craig Geisler is proud of Cherrywood Enterprises for reaching this high ground of success. At the time, the company used to buy accounts from other debt buyers due to a lack of understanding regarding the steps needed to purchase files directly from lenders. 

For the first couple of years, profits were marginal. However, with each transaction, Craig Geisler got more and more clarity about what was required to become a prominent name in the industry. In 2014, Cherrywood figured out the information necessary to give to other lenders, banks, credit unions, auto lenders, and commercial lenders for an opportunity to underwrite their files and determine pricing.

Once the company’s vision was clear, it all started to snowball for Cherrywood. It got better at its craft, identifying not just lenders it wanted to work with but also onboarding the attorneys to work its files on a much larger state level.

Cherrywood hit a milestone in 2018, shifting its focus to the commercial side. The company increased its buying power by 200%. From focusing on 90% consumers and 10% commercial files, the numbers changed to 60% commercial and 40% consumer files.

During the pandemic, when many businesses took a hit, Cherrywood’s numbers didn’t falter. Not just that, Cherrywood became fully equipped to buy good debt portfolios at a fair price while utilizing some of the best industry attorneys. The pricing given to lenders was based on six pillars of character and fairness and is one of the reasons why lenders love working with the company.

“We aren’t all about greed!”

Craig Geisler

Product Expertise

Cherrywood specializes in buying charged-off debt portfolios from banks, credit unions, auto lenders, and commercial lenders. They purchase charged-off credit card files, consumer loan files, auto deficiency files, and commercial loans and leases.


Technology plays a vital role in Cherrywood Enterprises and its rise to success. From utilizing Microsoft Excel Spreadsheets to identify crucial information on debt portfolios to reviewing backup documents and organizing data, technology is ingrained in Cherrywood at various levels.

“We couldn’t be as successful as we have become without Technology”

Craig Geisler

Staying Ahead of the Curve

As is the case with other industries, it is crucial for Cherrywood to be better than its competitors and stay ahead of the curve. To move even further than the competition, Craig Geisler says the company needs to identify the industry trends before they become trends.

In 2018, Craig wrote a few articles on commercial debt and how he felt it was the next big trend based on the new CFPB guidelines. Sure enough, it became a big hit within the debt collection industry.

The company must thoroughly understand the judicial state laws to follow collection and litigation guidelines. Doing so helps Cherrywood identify new states for its future business expansion and also gives an idea about what states it should avoid based on potential legal pitfalls. Moreover, Cherrywood must study which state will provide a better rate of return on its investment dollars and why.

Cherrywood strategically picks the states they litigate in. Moreover, when meeting with potential new attorneys in the new states, the company thoroughly understands the judicial process, court costs, how the state serves a debtor, and the processes it can utilize after the judgment has been awarded. If a business lacks a strategic approach, it risks shooting itself in the foot once the legal process begins.

Initial Challenges

At the inception, it was all about funding and gaining the knowledge required to work directly with lenders. When building a new company, there is always a “get-to-know-you” process and a lot of skepticism. Potential sellers want to know that you are not a fly-by night that might hurt their reputation in their respective communities once they sell their files to you. After gaining people’s trust, you must follow through and keep your promises.

Spark Leading to Growth

The direction Cherrywood wanted to take became clearer once it gained the necessary knowledge and funding. It was also the point when the company experienced significant growth. Being able to give references from companies it has worked with previously helped Cherrywood tremendously. When one creditor calls another creditor to vouch for and verify your work, the path toward working with new companies becomes a lot easier.

Humble Approach Paying Dividends

There are a few reasons for the company’s continuous success. One of them is having great people within the company who understand that everyone is working toward one common goal, and another is the lack of ego.

Many companies do great things for a while with an egomaniac running things. However, most do not achieve the long-standing success that Cherrywood has managed to achieve. One factor for the lack of success of these companies is that they get full of themselves. Naturally, such companies get served a big piece of humble pie.

On the other hand, Cherrywood always tries to keep the ego in check and realizes success breeds success, not ego. The company always puts its clients first. Without the clients, it wouldn’t have a business.

“It’s all about our people staying humble and staying ahead of the curve in the industry. The rest will work itself out.”

Craig Geisler

Challenging the Traditional Methods

Most companies become complacent after they reach a certain threshold and gain experience. These companies wait for the businesses to come to them because that is what they are used to. Craig Geisler believes in the old Aerosmith saying, “If you always do what you’ve always done, you will always get what you always got.”

What that means is Craig, although impatient by nature, knows that sometimes you need to change some processes to achieve better results, and to not get stuck in one way of thinking. To communicate clearly, he ensures a dialogue between himself, the company, and its clients. To stay on top of future business, he makes sure that clients know the exact requirements of Cherrywood. As a part of the “stay humble” mantra, Cherrywood always thanks its clients for their business. Moreover, the company also sends its clients a “Thank You” gift at the end of every year.

A Better Tomorrow

Cherrywood is always striving to do better than yesterday. The company is always trying new yet innovative marketing tools to keep its name out there. The company founded Cameo uses celebrity endorsements, as it makes a 30-second video from a celebrity that will endorse your company. Despite this simple approach, the overall response to Cameo was positive, and lenders loved this innovation.

Minimizing Risks

Craig is not a big risk-taker. While it may sound simplistic, Cherrywood Enterprises’ decision-making and risk-taking revolve around one basic principle: If it could hurt the business name or its reputation negatively, he finds it is best to avoid that step altogether. It takes years to build a good reputation, but only a few seconds to destroy it and that is a risk Craig Geisler does NOT want to take to make a few bucks.

Growing up, his father always told Craig: We share the same last name. When doing business with people, ensure you don’t tarnish the family name by bad or questionable decisions. Craig Geisler has taken this advice to heart and it influences every decision he takes.

One of the pivotal points in Cherrywood’s success is Craig’s leadership, which has effectively mitigated risks, enabling lenders to trust and feel good about their association with the company.

“I just want to make my parents proud of the company I have built. I would like to think they are.”

Craig Geisler

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