Dave, you know when to zig and when to zag,” proclaimed the baseball coach in admiration.

A high schooler at the time, David Iannarone didn’t exactly know what the man meant. Now the President of CWCapital Asset Management, he has since come to understand that zigging and zagging pertain to a kind of intuitive reflexivity lent by perceptive self-observation and reflection. It means swift and well-executed reaction based on the careful, calculated, thoughtful pre-consideration that allows one to learn a subject inside and out. The youngest of three siblings, he grew up a listener and observer, honing his ability to pick up on subtle facts and cues. Over the years, Dave has approached the path of his life in much the same way he had once approached the path of a baseball, using his reflections and objectives to determine when to zig and when to zag.

This is not to say that he always knew what he wanted to do in life. Rather, he developed a general idea of the realm he wanted to head towards and trusted his innate reflexivity to keep him aimed in the right direction. Thus, although he wasn’t certain whether he ultimately wanted to be a lawyer, Dave decided to pursue a law degree after graduating from college. When he attained his JD from Villanova and noted that he was more interested in transactional law as opposed to litigation, he took a position with the finance group at Kaye Scholer, LLP, a premier law firm in New York City. True to his natural form, he constantly reviewed and reflected upon his current position in the context of future goals. “In the back of my mind, I was always trying to build my resume towards more of a business focus,” he recalls. After three years at Kaye Scholer, he had learned the ins and outs of running a transaction from beginning to end.

With the running theme of business orientation in the back of his mind, he then took a position with Citibank. Enjoying a constant stream of new learning experiences and analytical demands, Dave remembers the first six months of his employment as a thrilling time. The influx of opportunity, however, was promptly cut off with the thrift crisis and real estate debacle that came with the 1980s’ denouement. “I was always told it was a cradle-to-grave type of job, and frankly the grave part scared me,” Dave laughs now.

With Citibank entering a period of relative isolationism, he was afforded new perspective on his position. “It was what I thought I was looking for—pretty controlled, pretty orderly. But in the end it was pretty boring as well,” he concedes. Identifying the personal need for a challenge, he made a zig and focused his energies on earning his advanced law degree at New York University. With the heightened business focus of the LLM, he had the opportunity to learn about disclosures, verbiage, shareholder voting procedure, director appointment procedure, and the rules of directorship. With its fundamental focus in business law, the program figured ideally into his grand plan.

Growing restless of New York City, however, Dave felt it was time to zag and found himself answering an advertisement in the Wall Street Journal for a position with the Resolution Trust Corporations (RTC) in Washington, DC. After transferring his LLM program from NYU to Georgetown and hopping a train south, he suddenly found himself leading a brand new life teeming with fascinating people and work. Heading up the national program for residential securitization, he introduced the policies and procedures for assembling loans from banks and selling them to Fannie Mae and Freddie Mac. Noting that tax law drives so much of the business landscape, he ultimately earned his LLM with a focus in Securities and Tax.

Ever introspective and self-aware, however, Dave eventually came to feel that his duties at the RTC were no longer stretching his capacities. It was around this time that a headhunter happened to mention a job opening at CRIIMI MAE Inc. that entailed a smorgasbord of varying duties, promising extensive experience in public and commercial real estate finance company happenings. The job was perfect for Dave, and he worked there quite contentedly until the company filed for bankruptcy. Despite entertaining notions of starting his own entrepreneurial venture, he eventually succumbed to the advice that seeing CRIIMI through the bankruptcy process would afford him a tremendous learning experience; thus, he stayed on and served as chief restructuring officer.

Once CRIIMI had successfully navigated through bankruptcy and Dave had fulfilled his subsequent two-year contract of employment, he departed to assume the role of Director of Capital Markets with Allied Capital Corporation in 2003. The opportunity diverged somewhat from the commercial real estate finance sector he was used to, and he enjoyed the challenge of applying his seasoned expertise to a new sector. “You get smarter as you get older, and the one thing you learn to do is trust your instincts a little more,” he explains now. He declined other job offers to remain with Allied until switching over to the CWCapital Asset Management (CWCAM) platform in July of 2005.

CWCAM manages distressed assets, a far more complex and fascinating process than first meets the eye. The field has evolved and merged over the past twenty years to demand dual expertise in both commercial real estate and finance—true Renaissance individuals capable of understanding the subtle yet comprehensive nuance and analytics behind property valuation and loan processes. This is further compounded by the necessary consideration of the investors behind the loans, the broader real estate lending market trends at work, and the legal component underpinning the enterprise.

“The most fascinating part about it is you’re not sitting in your office or cubicle working through these ideas, numbers, and conclusions,” Dave explains. “You’ve got to interface with people, negotiating and fighting for the best deal for the lender.” This implies the importance not only of impeccable industry knowledge, but of iron negotiation skills as well.

In his first three years with CWCAM, Dave and his team’s primary goal was establishing a premier commercial mortgage loan shop. With his hallmark trait of reflection, Dave sensed that the spoilage of commercial loans was imminent, so his efforts took on a proactive and preparatory vision. Training, systems, and processes became key considerations for the business, as well as the art of swift and efficient decision-making. Each asset manager was equipped with optimal levels of support, with junior employees aiding senior associates and gaining the knowledge to become associate asset managers themselves in the future. “When commercial loans went bad, people were surprised by our preparedness,” Dave remembers. “This was not by accident, but by design.” Because of his vision and foresight, CWCAM was prepared to staff up and scale to manage more assets, growing from 65 employees in 2008 to over 140 employees now, securing their renown as a premier special servicing platform.

Beyond this foresight, CWCAM is rendered so unique amidst this developing and fast-paced atmosphere by its capacity to offer high-powered staff with deep industry experience. “We’re diverse,” says Dave. “We have the real estate guys and the workout guys, and we have very strong technology. Within this, our true value lies in our attitude and how we work together to develop a level of knowledge that is unparalleled.”

In reviewing his journey to this point, perhaps the most pronounced and compelling aspect of Dave’s story has been the compounding nature of self-knowledge. Unsure of the exact path for him, he was able to find it through observing his skills and passions and then working toward them until a clear goal solidified. The journey in turn granted him further self-knowledge, as he was able to monitor his own responses to new situations and obstacles. While working at Allied, for example, he was asked whether his skills were more transactional or operational oriented. Though at the time he believed he was more transactional, he has since reclassified himself an operations guy. “I like creating a goal and helping everyone grow in the same direction to get to that goal,” he explains. Allowing this kind of organic growth of the self instead of trying to force one’s skills into a predetermined mold guarantees a much more natural and steadfast success. “Really, you need to learn who you are and then pick things that you’re good at,” he emphasizes.

Thus, one cannot expect to land in the perfect professional situation immediately upon entering the workforce. While navigating along the path to your ultimate goal, Dave reiterates the importance of continuous evaluation of situation and self in order to stay on track. “When participating in your first jobs, ask yourself if you’re learning,” he encourages. “Then, look at those jobs and ask what parts you liked.” He also emphasizes the importance of learning as many skills as you can, even those that seem repetitive, boring, or obtuse. “People often feel that they want to take on more responsibility in a new job, but your boss doesn’t want to give you the hard tasks if you aren’t demonstrating that you can do the easy tasks,” Dave reminds us.

Just as he is continually drawing on a plethora of sources to inform his reflections, Dave’s journey of personal and professional evolution is far from over. “I see the future as bigger and better,” he says, referring to CWCAM’s prospects. In his own development and in his advice to others, he remains acutely aware of the continuous opportunity to excel and strives to never drop the ball. “People don’t seem to realize that we’re always getting graded,” he remarks. “Develop the network around you just as much as the network above you, because your co-workers will all move elsewhere in the professional world and will maintain lasting impressions of you.” Dave holds that such impressions are derived from one’s quality of work, quantity of work, and the attitude employed while doing that work, so he monitors these facets constantly to ensure lasting success. It’s all part of the art of zigging and zagging: discovering yourself and carving out your own road toward professional achievement and personal fulfillment.