Picture rolling spare coins across a gas station counter just to make it home with enough left over for groceries. Now picture that same person, twenty years later, sitting at the helm of a company that decides which multimillion-dollar debt portfolios are worth the risk. That’s not a redemption arc Hollywood writes — it’s a Tuesday in the life of Craig Geisler.
The debt acquisition industry doesn’t get much love. People hear “debt buyer” and picture vultures circling, squeezing every last dollar out of people who are already underwater. Craig built his entire company on proving that story wrong. Cherrywood Enterprises runs on an idea most of the industry treats as a liability: empathy is good business. Most people want to pay what they owe — life just got in the way. Treat them like humans instead of line items, and the numbers actually improve.
That belief didn’t come from a business school case study. It came from 2007, when the mortgage market collapsed and Craig had two daughters to feed and no Plan B. He didn’t pivot into debt buying because it sounded glamorous. He did it because failure stopped being an option the moment it became personal. Every deal he’s closed since, every portfolio his underwriters have picked apart line by line, carries a piece of that lesson: never again.
Today, as Cherrywood marks its place among the well-known M&A Leaders , Craig’s path looks less like a straight line and more like a series of calculated bets — on commercial equipment portfolios nobody else wanted to touch, on a “team first” mentality in an industry obsessed with profit first, on the idea that reputation outlasts every quarter’s earnings.
Inspired by his work and the unconventional road that built it, we sat down with him to learn how a guy who once counted coins for gas ended up writing the rules other dealmakers now follow.
Below are the excerpts from the interview:
Craig, your career took an unexpected turn after the 2007 mortgage market collapse. Looking back, how did that period of uncertainty ultimately become the foundation for your success today?
I didn’t have a Plan B. I had to figure it out because I had my 2 girls and I. I was rolling coins to get gas and buy groceries. It was at that point I told myself I was never going to allow myself to struggle again. So, when I started working as a debt buyer, I made sure I was consistently one of the top performers. I had great training to understand the industry very quickly. It was just maintaining that “can-do” attitude and making sure I never allowed myself to be in that position again. When you start your own business, you must have the mentality that you will never allow yourself to fail again. You always have that thought in the back of your head that if you don’t persevere, you know what that could lead to. Laziness can never be a possibility when you own your own business.
You entered the debt purchasing industry with only a short period of formal training and eventually launched your own company. What gave you the confidence to take that leap?
I worked for 3 different debt buyers, who are no longer in the industry, and I learned something from each company. It allowed me to see the positives for each company, what they did right, and to also see the negatives and what they didn’t do so well. I just knew that I could create a company and focus on what they did right and how I could be better. The biggest takeaway I had was to put client focus, first. If you don’t have a clientele, you don’t have a business! So, we focus not just on taking care of our existing clients, but attracting future clients, as well. Our goal is to give every client that winning experience, so they come back to do business with us again and again.
In your experience, what are some of the biggest misconceptions people have about debt acquisition as a business?
That the collection industry is all about sucking funds away from people any way possible and that people in the industry are bad people. In fact, the industry helps people more than hurting them. When the debt is created, it goes on most debtors’ credit report. It negatively affects your score. However, once you start making payments OR just pay off the balance, it helps increase your credit score. We are not here to take every dollar you have, but we are here to help you to find financial freedom! We work with debtors using an empathic approach. We know most debtors WANT to pay their bills, but something happened that they couldn’t. We work to find solutions to get them back on track.
Whether acquiring a company or purchasing a debt portfolio, success often depends on assessing risk correctly. How do you personally approach high-stakes decisions when the outcome is uncertain?
It certainly isn’t easy and I cannot take all the credit myself. We have an amazing team of underwriters who review all the files we purchase. They analyse everything from geographic location, dates the account was opened, charged off, and when the debtor last paid. They look at language that allows for attorney’s fees, court costs, and hiccups like arbitration language. Based on all the data, that’s where we assess what we need to pay for the files. We always try to find a little bit extra to give to the lenders to make our pricing more aggressive than our competitors. We want to win every file we review but we also know that isn’t always possible. What it really comes down to is what price can we pay that allows us to make money but also that gives an incentive for the lenders to want to do business with us over and over again.
Can you share an example of a deal or acquisition opportunity that fundamentally changed your perspective on risk and reward?
It was 2018 and we just started looking at commercial equipment portfolios. We had never purchased commercial files, so we had to do a lot of due diligence and talk to companies who had purchased it in the past to get their feedback. It wound up being one of the best decisions I could have made. Now, the commercial equipment space makes up approximately 73% of our acquisition portfolio and has produced solid numbers with our attorney network. It was a new venture for us that proved to be a great move for the business.
When you founded Cherrywood Enterprises in 2012, what gap in the market were you hoping to address?
I don’t know if it was essentially a “gap in the market”, but more so I saw the mistakes that my previous employers were making, and I thought I could do it better with a more client friendly approach. Without your clients, you simply don’t have a business. So, the first step in creating Cherrywood Enterprises was establishing the 6 pillars of success: trustworthiness, respect, responsibility, fairness, caring, and citizenship, for our business. These are the foundations of our business. Then, when working with our attorneys, we put a big emphasis on having empathy towards the debtors. As I have said before, I believe everyone has the intention to pay their debt on time, but sometimes, “life” happens. If you start with an empathetic approach, it disarms the debtor from thinking we are only interested in taking all of their money. We want to work with each one of our clients and trying to be fair on all sides. Lastly, it’s leading with purpose. I always use a “team first” mentality. Many business owners use a profit first mindset and that doesn’t always translate to longevity. Your team is the backbone to your business, so why not treat them, as such? So, using all of these strategies, I think puts us in a good position to be the best in the industry, gives us a good name in the industry, and sets us up for success for the long term. That’s a win-win we can all get behind!
The financial services industry is being reshaped by data analytics, automation, and AI. How do you see these technologies influencing debt acquisition and portfolio management in the future?
It already IS shaping the industry. From collections, to marketing, to portfolio analysis, AI is here whether we like it or not. Debt collection is already using AI for collections calls and responses. Many use AI to create a marketing plan, delivering it, and using the metrics to see who is seeing your marketing material, what makes your audience respond, and what is the best way to market your business and to whom. Lastly, AI is used to evaluate debt portfolios using metrics like city, state, zip, first and last name, and the likelihood of a debtor paying and what would be an ideal amount for a payment plan based on the median income in their area. It really has become a powerful tool in the industry and it’s only going to become more prevalent in the years to come.
When people look back on your career, what do you hope they remember most: the deals you completed, the company you built, or the impact you had on others?
All of the above. Everyone wants to be remembered in a certain way. Early in my life, I wanted to be rich and powerful. Looking back on that mindset, it was a very naïve way of thinking. Now that I am in my 50’s, I want to be remembered for the good things I did and how I strive to give back. Remembering back to a time when I had to roll coins to put gas in my car. When my weekends were all about staying in and working to get to the next level. Now, with a little success under my belt, I want to help people to achieve success. We give to great organizations like St. Jude and the Wounded Warrior Project, to help those in need. Both are great organizations. Here in Orlando, we give to the Salvation Army, as well. We belong to the East Orlando Chamber of Commerce, and we started doing a Friends In Business Dinner once a month to help promote local business and create a fun and interactive way to help local businesses market themselves. I love helping people and finding ways to help great people achieve great things. So, that is what I would like to be remembered for…in addition to being a good father, grandfather, friend, son, brother, and all-around human being.
What advice would you give aspiring entrepreneurs who are trying to identify opportunities in industries they know little about today?
First, I would suggest they research opportunities. Nowadays, there is so many great ways to research different career opportunities. So, my best advice is to “research”! Read about the different industries, books, YouTube, Google, and even Chat GPT! Then find businesses who are in your field of interest and reach out to them to pick their brain. Ask about what they did to achieve success, challenges they faced and how they overcame them, and tips to help get started. Then the next step is marketing. Your goal is to introduce yourself and your company to as many people as possible. Then, as you start getting business, ask for referrals! Referrals from people who have done business with you is a great way to get introduced to more people to do business with! Lastly, and MOST importantly, always thank people for their business. People forget to say thank you nowadays, but when the job is done, what do you think people remember the most? That is the best advice I could give to aspiring entrepreneurs.
Finally, what does being recognized among the “M&A Leaders of the Year” mean to you personally, considering the unconventional path that brought you here?
Any time that I am recognized, I am humbled. I never see myself in any way other than a normal guy who came from a blue collar background, who worked hard, built solid relationships along the way, and never forgot where I came from. My Dad once told me, we share the same last name, so never do anything that will tarnish that. Reputation is everything. I never forgot that. He was so right. So, it means that I followed my father’s advice to the tee. I did things right. I made good choices, and I have helped, and will continue to help, as many people as I can along the way. I will continue to work hard and I hope that anyone who reads this is inspired to do something great with your life and career. Sometimes you have to take calculated risks. As Michael Jordan once said, you miss 100% of the shots that you don’t take.
