In this interview, we delve into the remarkable story of how Craig Geisler, the President and CEO of Cherrywood Enterprises, LLC, embarked on his path to success in the debt purchasing industry. Join us as Craig shares his experiences, notable accomplishments, leadership style, and the values that have guided him along the way. Discover what sets Cherrywood Enterprises apart from other companies, how Craig navigated the challenges of a fluctuating market, and his aspirations for the future. Get ready to be inspired by Craig’s journey as a CEO and his relentless pursuit of excellence in the field of debt purchasing.
Introduction and Career Path
Craig Geisler is the President and CEO of Cherrywood Enterprises, a debt purchasing company. Craig’s journey into this industry began somewhat unexpectedly. After working in the mortgage space for nine years, the collapse of the Florida market in 2007 left him uncertain about his next steps. Fortunately, a company in the debt purchasing industry discovered Craig’s resume online and provided him with two weeks of training. Craig excelled in the field and soon launched his own company in 2012. Reflecting on this period, Craig acknowledges that he was very fortunate to have found his niche and has never looked back since.
Continuous Growth and Development
In Craig’s view, continuous growth is essential for staying ahead in the industry. Craig believes that stagnation leads to a loss of competitive edge, as someone with a better approach will inevitably come along. To maintain their position, Cherrywood Enterprises attends conferences, stays updated on trends and changes in state and federal laws, and strives to anticipate future trends. By setting trends rather than following them, Craig ensures that Cherrywood Enterprises remains a leader in the industry.
Vision and Differentiation
Craig’s goal is always to be the best in the business. His vision involves being the first to enter new markets, understanding the laws and costs associated with those markets, and setting Cherrywood Enterprises up for success. Craig emphasizes that knowledge is power in the debt purchasing industry, and the more one understands, the more successful they can be. Cherrywood Enterprises is also exploring new marketing strategies, especially with the rise of AI, to enhance their already robust marketing plans and differentiate themselves from competitors.
Fostering Innovation and Adapting to Challenges
Craig is a firm believer in the importance of adaptability in leadership. He recognizes that he does not have all the answers, but he does have a great team. Collaboration and feedback are key components of Craig’s approach. For instance, when a marketing email was not yielding the desired results, Craig’s VP of Marketing suggested a more concise approach. This change made a significant difference. Craig credits his team’s ideas and feedback for helping Cherrywood Enterprises overcome challenges and achieve success.
Resilience in the Face of Adversity
Resilience is a crucial quality in Craig’s leadership style. He emphasizes the importance of pausing, thinking, and being patient when faced with setbacks. In the debt purchasing industry, challenges often arise during negotiations with lending institutions. Craig believes that maintaining composure and engaging in calm, thoughtful discussions helps both parties reach a solution that works for everyone. This approach has allowed Cherrywood Enterprises to turn potential setbacks into opportunities for growth.
Empowering Leadership within the Team
Craig believes that leadership potential exists within everyone, depending on the situation. As the head of the organization, it is Craig’s responsibility to recognize these traits and utilize them appropriately. When challenges arise, Craig engages his team in discussions to gather feedback and identify the best solutions. By empowering his team to contribute ideas without fear of negative feedback, Craig fosters a collaborative environment where everyone feels valued and capable of taking on leadership roles.
Mentorship and Leadership Development
Craig’s approach to leadership has been shaped by his own experiences with mentorship. Early in his career, Craig worked for a news publication where the CEO saw potential in him and promoted him to VP of Investor Relations. This mentorship provided Craig with invaluable knowledge, confidence, and leadership capabilities. The experience taught Craig the importance of organization, accountability, and effective communication, ultimately preparing him to run his own company. Craig remains grateful for this mentorship and strives to mentor others in a similar way.
Addressing National Challenges
While Craig does not claim to tackle global challenges, he is keenly aware of national issues that impact the debt purchasing industry. Rising interest rates, for example, put stress on lending institutions and borrowers alike, leading to an increase in charged-off loans. Cherrywood Enterprises steps in to purchase these portfolios, providing lenders with an immediate revenue stream to offset their losses. Craig’s ability to navigate these challenges has been instrumental in the company’s success.
The Impact of Emerging Technologies
Craig identifies artificial intelligence (AI) as a game-changer for the debt purchasing industry. AI has the potential to revolutionize collections, marketing, risk assessment, and portfolio pricing. As the industry continues to explore the best ways to utilize AI, Craig believes that its impact will only grow. Cherrywood Enterprises is committed to staying at the forefront of these technological advancements to maintain their competitive edge.
Risk-Taking and Decision-Making
Risk-taking is inherent in Craig’s approach to leadership, particularly in an industry focused on charged-off loans. However, Craig emphasizes the importance of calculated risk. When evaluating portfolios for purchase, Cherrywood Enterprises carefully analyses all aspects to ensure a balance between risk and profitability. While Craig is eager to pursue new deals, he understands the necessity of walking away when the pricing does not make sense. Trusting his team’s expertise in underwriting allows Craig to make informed decisions that support the company’s growth.
Crisis Management
Craig credits his ability to manage crises to a mindset of patience and composure. Early in his career, he learned the importance of not responding in frustration or anger, as this approach often led to lost business. Today, Craig takes time to think through challenges and responds in a way that reflects his professionalism. By maintaining this approach, Cherrywood Enterprises has successfully navigated crises and preserved client relationships.
Prioritizing Employee Well-Being
For Craig, the well-being and satisfaction of his employees are paramount. He views his employees as an extension of his family and believes in creating a balance between work and personal life. Financial health is also a priority, and Craig ensures that his employees are compensated fairly for their hard work. By fostering a positive work culture where employees feel valued and motivated, Craig has created an environment where everyone can excel.
Continuous Personal Development
Craig is a firm believer in the importance of self-reflection and continuous personal development. He views mistakes as opportunities for growth and encourages his team to learn from their experiences. Craig is also an avid reader and a fan of personal development content on YouTube, particularly the teachings of Tony Robbins. By continually seeking growth and development, Craig sets an example for his team and maintains his own leadership effectiveness.
Significant Achievements and Milestones
Craig’s career has been marked by rapid promotions and significant achievements. In nearly every job, Craig was promoted within 90 days of starting. When he founded Cherrywood Enterprises in 2012, he had to earn the trust of his clientele and deliver on his promises. Craig’s commitment to loyalty and customer satisfaction has set his company apart from the competition. Recently, Cherrywood Enterprises was recognized as one of the fastest-growing companies in the industry—a testament to Craig’s leadership and the dedication of his team.
In conclusion, Craig Geisler’s journey from navigating the collapse of the Florida mortgage market to becoming the President and CEO of Cherrywood Enterprises is a testament to his resilience, adaptability, and unwavering commitment to excellence. His strategic vision, dedication to continuous growth, and ability to lead with empathy have not only propelled Cherrywood Enterprises to the forefront of the debt purchasing industry but also set a powerful example of leadership in challenging times. Craig’s story is a compelling reminder that with the right mindset and a strong team, even the most daunting challenges can be transformed into opportunities for success.
