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Evan Wilkoff Talks About Overcoming Failure and Motivating a Team for Outstanding Results

jean pierre fumey



Evan Wilkoff BW

Meet Evan Wilkoff, an accomplished financial services professional and consultant with a wealth of experience in the field of asset-backed and structured finance. Throughout his career, Evan has demonstrated strong leadership skills and a talent for building profitable businesses and platforms. From 2010 to 2021, he served as the Executive Vice President of Ascentium Capital LLC, where he spearheaded the company’s capital markets and treasury activities.

During his time at Ascentium Capital, Evan Wilkoff designed and implemented a highly successful funding strategy, which included a robust asset-backed security issuance program, multiple credit facilities from renowned money-center banks, and various syndication sources. While at Ascentium Capital, the origination volume exceeded $2 billion in less than five years and reached an impressive $8 billion in a decade.

One of Evan’s major accomplishments at Ascentium was overseeing the asset-backed securities issuance program, which saw $3.4 billion issued across 12 transactions. Additionally, he successfully managed portfolio sales totaling $1.4 billion, generating significant gains of over 5% and involving 57 purchasers. Evan’s expertise also extended to establishing and managing an offshore reinsurance company, which proved highly profitable for Ascentium through net underwriting profits from their automatic insurance product.

Evan’s ability to identify promising opportunities and nurture successful business platforms is evident through his contributions at Ascentium. He played a crucial role in the creation of three business platforms, including truck finance, a direct-to-end-user call center, and a micro-ticket point-of-sale equipment finance division. By leveraging his skills and industry knowledge, Evan played a key part in acquiring, launching, and/or integrating these platforms into Ascentium’s operations, contributing to the company’s overall success.

Prior to his tenure at Ascentium Capital, Evan Wilkoff had achieved success in several progressively responsible roles in corporate finance. As the Director of Commercial Asset Finance at Wells Fargo Securities, he tripled annual revenues within his division. In addition, he excelled as the Vice President and Treasurer of CoActiv Capital Partners, Inc., LLC, where he managed bank relationships, negotiated senior warehouse lines, and developed a syndication strategy.

Evan is also the co-founder of Cavalier Funding, LLC, where he built a full-service specialty finance company from scratch. During this venture, he developed a proprietary pricing model that effectively maximized profits while minimizing risk.

Evan Wilkoff’s academic background includes a Bachelor of Science degree in Systems Engineering from The University of Virginia, which provided him with a strong foundation to excel in the complex field of finance.

Recently, we had the privilege of speaking with Evan Wilkoff to gain insights into his secrets to productivity and the invaluable lessons he has learned throughout his career.  He was gracious to share his insights and experience with our audience.

What is the one thing you do over and over and recommend everyone else do? 

To consistently improve and grow both personally and professionally, one habit I have found to be immensely valuable is traveling, connecting with individuals on a deeper level, and networking. This is because traveling not only exposes you to diverse cultures but also expands your perspective and understanding of the world.

Connecting with people on a personal level is crucial because it allows you to build genuine relationships, which in turn can lead to new opportunities and collaborations. Networking is a key component of this, as it enables you to meet individuals from all walks of life and industries, providing a rich tapestry of potential connections and ideas. By making a habit of regularly engaging in these activities, one can continually learn, grow, and create new opportunities for themselves and others.

What is one failure you had, and how did you overcome it? 

One of my biggest failures was when I started my own business with a partner after months of planning. However, after setting up shop, we realized that the phones weren’t ringing and we were not generating any business. We had to quickly pivot our business plan and start generating leads to keep the company afloat.

It was challenging, but we slowly grew the company over the next few years. Ultimately, we decided to sell the company and take on senior positions within another organization, which proved to be a valuable learning experience. This failure taught me the importance of being adaptable and nimble and that success often comes from being able to pivot quickly in the face of unexpected challenges.

What qualities and skills do you look for when hiring new talent? 

When hiring new talent, I look for individuals who possess a strong blend of communication skills, analytical proficiency, and the ability to adapt to new challenges and changes easily.

Effective communication is a key factor in any successful business, and I believe it’s a skill that’s often undervalued in the workplace. In addition, I look for candidates with strong analytical skills, particularly in spreadsheet analysis, as this skill set is often critical to making informed decisions that drive business growth.

Finally, flexibility is essential in today’s ever-changing business environment, and I seek out individuals who are open to new experiences and able to pivot when necessary to achieve our goals.

How do you motivate your team for outstanding results? 

As a seasoned leader, I strongly believe in fostering a culture of autonomy and trust within my team. Instead of micromanaging, I prioritize empowering my employees to work through challenges independently – and not be afraid to ask for help.  I also recognize the importance of regular oversight and reporting to ensure everyone is on track.

However, I also understand that work should not always feel like a chore. In order to keep my team motivated and engaged, I make it a point to incorporate fun and levity into our work environment. By creating a positive work culture, I have found that my team is more likely to be motivated and invested in their work.

Additionally, I recognize the importance of a proper reward and compensation structure. By providing my team with appropriate incentives, I am able to motivate them to strive for outstanding results.

How do you handle difficult clients, customers, or coworkers? 

Dealing with challenging clients, customers, or coworkers is always a delicate situation. While it’s not my strongest skill set, I’ve learned to handle these situations with patience, empathy, and a solution-oriented approach.

I try to understand their perspective, identify their concerns, and find a mutually beneficial solution. If needed, I involve other team members or escalate the issue as appropriate, but always with a focus on maintaining a positive and productive relationship.

Jean-Pierre is a polyglot communication specialist, freelance journalist, and writer for with over two decades of experience in media and public relations. He creates engaging content, manages communication campaigns, and attends conferences to stay up-to-date with the latest trends. He brings his wealth of experience and expertise to provide insightful analysis and engaging content for's audience.

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