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Kenny Smith

Managing Director, Crystal Financial

40 Under 40 Category: Business Development


Kenny Smith is a managing director at Crystal Financial, responsible for sourcing and structuring new transactions from a nationwide network of private equity firms, commercial banks, and other intermediaries. Kenny joined Crystal in 2011 as a member of its underwriting and portfolio management team. Prior to joining Crystal, Kenny held roles at JMH Capital, Breakaway Ventures, and BDC Capital. He received his B.A. from Harvard University and his M.B.A from the F.W. Olin Graduate School of Business at Babson College. He currently serves on the Board of Directors of the Secured Finance Network’s New England Chapter. Kenny lives in the suburbs of Boston with his wife, Karianne, and their sons, Kenny and Patrick.

What effect has the COVID-19 crisis had on your professional life? 

As awful as this crisis has been, there have been some silver linings to our new working environment. Like many of us, I’m working entirely from home. While that has its challenges, it is really nice to have so much extra time with my wife and two sons. The workdays are incredibly busy, but being able to sit with my family for most meals during the week is a nice change of pace and it gives good real-time perspective as to why we work so hard. The other positive I’ve experienced around this change in work environment is a sense of camaraderie with colleagues and counterparts alike, around dealing with the work-from-home challenges. With so many folks dealing with connectivity issues, children entering Zoom calls, or dogs barking in the background, I’ve found people to be a lot more collegial, even in difficult conversations. The sense that we are all in the same boat, dealing with similar issues, seems to have created a sense of understanding with everybody.

What is the best professional advice you have been given and how have you implemented it?

The best advice I’ve been given was by my parents and that was to have integrity in all that you do, and to “be your word.” While this wasn’t meant to be advice specific to a career in secured lending, I think incorporating that into my role has been very important. We deal with complex financings, in hypercompetitive environments, on short timeframes. It is really important that everyone in these processes understands exactly where we stand, what we can do, and what we can’t. In addition to simply being the right thing to do, I believe being clear and candid creates a level of trust that not only makes the transactions go more smoothly, but also leads to repeat business. 

How do you define a good leader?

I believe the best leaders, be it in families, teams, businesses, or other organizations, are those who take on their role with a tremendous work ethic and a strong sense of humility. Effective leaders need to demonstrate a deep level of caring about the members of their organization. Leading by example by being willing to work as hard as any other member of the group is one way to demonstrate that level of care. Being humble is another. A willingness to give credit to others, to take opinions from others, and to empower others to go out and perform their roles decisively, shows humility in a leader. Demonstrating that level of trust in the members of the organization is empowering and creates a sense ownership for everyone. Any organization that is comprised of people who feel valued, and who are being tasked with going out and executing their role well, is going to see positive results. 

I also think the best leaders are those who are willing to follow other good leaders. If someone is better suited to lead or handle a situation, a good leader will recognize that and allow them to do so.

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