Editors’ Note

Gordon Caplan is the founder and Chief Executive Officer of Dutchess Management LLC, a strategic advisory firm dedicated to helping clients navigate complex business challenges and promoting social good through philanthropic ventures. Prior to establishing Dutchess Management, he was the Co-Chairman of Willkie Farr & Gallagher LLP from 2015 to 2019. He was the Chair of the Private Equity Practice at Willkie Farr from 2010 to 2015 and the Chair of the Venture Capital Practice from 2005 to 2010. He also served as Chairman of the Board of Connecticut Telephone from 2004 to 2006. Caplan was named a “Dealmaker of the Year” by American Lawyer in 2018 and featured in publications on M&A, private equity, corporate governance, and high-technology transactions. He has lectured on private equity and technology transactions at Columbia University Graduate School of Business, the University of Pennsylvania Law School, and Fordham Law School. Caplan received a JD from Fordham Law School, where he was an Editor of the Fordham Law Review, and a BA from Cornell University College of Arts and Sciences. He is a member of Fordham Law School’s Dean’s Planning Council, and a Board Member of Publicolor and was the Chairman of the Board of Publicolor from 2014 to 2018. He received the 2016 Louis J. Lefkowitz Public Service Award from Fordham Law School. Caplan also serves as a voice for criminal justice reform, spearheading the Prison Visitation Fund (prisonvisitationfund.org), a nonprofit dedicated to keeping families together during a loved one’s period of incarceration.

Firm Brief

Dutchess Management (dmstrategic.com) is a strategic advisory firm focused on corporate transformations and complex transactions. It is comprised of a team of dealmakers, strategists, analysts, and problem-solvers. The firm views its clients as partners and helps them unlock hidden value and elevate their success. Some of the firm’s partners include Saks Fifth Avenue, Saks Off Fifth, Veeam, Hudson’s Bay Company, Kubeshop, Spartan, Tractable, and Acronis.

Will you describe the evolution of your career?

I began my career as an attorney after graduating from Fordham Law School in 1991 and ultimately rose to serve as co-Chairman of Wilkie Farr & Gallagher, a global elite law firm with over 1,200 lawyers worldwide. I’ve been fortunate to work with great clients and people over the years, and to be involved at a high level in fields like technology, entrepreneurship, and private equity, among others. I’ve always prioritized being there for others to overcome obstacles in order to move the ball forward in meaningful ways for my clients. Now in my work with my firm, Dutchess Management, I’m able to continue prioritizing this client-focused culture alongside an extraordinary team of colleagues and associates.

What do you feel were the major factors that contributed to your early successes?

It’s always been a simple approach for me: work hard and add value for others, serving clients and causes by delivering great work and results. Not every job has the same immediate feedback that we can get as dealmakers, like seeing a happy client or a deal get done. I was a competitive kid growing up. As part of an immigrant family new to the U.S. from Canada, I always wanted to achieve more, whether in school or playing sports. When it came to my career, I didn’t have all that much of a burning direction until law school. Something clicked. Suddenly, I now had a new mechanism – a new arena – to pour my energies and ambitions into. Working hard was par for the course as a young lawyer in New York and London, and I fed off of that when I was first beginning in the late 1990s, all the way through today.

Will you highlight the work you do today with Dutchess Management?

I founded Dutchess Management in 2020 to provide specialized expertise and guidance to businesses, primarily in the entrepreneurial space. It started as a one-person operation, and we have steadily grown since. We have also built out our pro bono work, which I’m proud to say represents a significant part of our work. We do not provide legal services, instead we work through complex deals and problems on behalf of a select group of highly-successful entrepreneurs and partners.

Our core mission at Dutchess revolves around helping businesses and entrepreneurs reframe their strategies, restructure their operations, and navigate complex challenges. We specialize in working with companies in the software and technology sectors, so my deal experience has significantly shaped our ethos at Dutchess Management. As a former co-chairman of a large law firm, my work often transcended the legal component, and I found myself immersed in strategy, advising on business direction, risk management, and navigating the intricate landscapes of the corporate world. Dutchess now effectively embraces this multifaceted role in assisting our clients.

At Dutchess, we are also prepared to jump in whenever an urgent need is identified in a community or where we see a gap that’s not being filled, whether from a humanitarian or criminal justice standpoint. We’ve leveraged our expertise and networks in places like Afghanistan, where we were able to help save 800 Afghanis – primarily women judges and lawyers and their families – under threat from the Taliban. I am also very proud of our work in response to the Russian invasion of Ukraine, where our team is focusing on a number of fronts. We’ve supported efforts to forge cross-border partnerships between the Kyiv School of Economics and Ohio State University. We also supported and joined with a courageous and committed group that led a caravan of trucks delivering humanitarian supplies to the front lines for Ukrainian civilians.

During my visits to Ukraine since the outbreak of the horrifying Russian war, one of the amazing people I met was Roza Tapanova, the head of the Center for Jewish History in Ukraine (CJHU) at Babyn Yar. The CJHU is establishing an academic and cultural hub for the preservation of Ukrainian Jewish history located at Babyn Yar, a ravine outside Kyiv in which nearly 34,000 Ukrainian Jews were killed by Nazi soldiers in September 1941. The CJHU is committed to expanding the scope of academic study of Ukrainian Jewry at Babyn Yar in order to preserve and resurface centuries of Jewish history and culture across the country. Continued threats to the memory of Babyn Yar add additional urgency to the CJHU’s mission. Babyn Yar’s memorial sites were damaged following a Russian missile strike on March 1, 2022, which killed five civilians, caused a museum building to catch fire, and destroyed other memorial facilities. We have helped direct philanthropic support to organizations like these, protecting Holocaust memorial sites and communities across Ukraine.

You were one of the high-profile parents who were involved in the Varsity Blues college admissions scandal. You admitted that what you did was wrong, and were briefly incarcerated. How did this experience change you?

That experience has been the most profound turning point in my life. Facing the reality of my terrible mistake was, and remains, an arduous journey of self-examination. Not a day goes by where I don’t reflect on the decisions and mistakes I made, for myself and my family. I’m the first one to say it was wrong, stupid, inexcusable, and a decision I know I will deeply regret for the rest of my life.

My incarceration was challenging, yet brief in the grand scheme of things. Like many others in the legal field, I know our criminal justice system has been broken for far too long. I witnessed firsthand how many serve for longer than I did. Serving time afforded me the opportunity for deep introspection, to begin on my journey of understanding how I could possibly move forward and to examine what my core beliefs and values are, and how I can practice them in service of others. So I began small, even while in prison. I taught business literacy and entrepreneurship skills for those incarcerated and, ultimately, we had 35 or so prisoners – out of a total prison camp population of approximately 80 people – coming to learn what life after prison can look like if they start businesses. There are very few viable pathways for formerly incarcerated people to make a living and regain their footing once they’re out, which helps contribute to this negative cycle of recidivism in our country.

You have been committed to philanthropic causes throughout your career. How has your experience with the criminal justice system shaped the focus of your philanthropy?

Directly seeing the challenges faced by those incarcerated alongside me was sobering and eye-opening. I’ve used these moments to shape my efforts moving forward – serving others and doing good is now what I’m focusing my time, attention, and resources on. It’s both personal and professional. It’s how my partners and I have designed Dutchess Management, so that there is no distinction between our paying and pro bono clients. In line with this commitment, I have made a point to hire individuals who themselves have needed second chances – providing them with an opportunity to rebuild their lives and contribute their talents to our shared vision.

In the criminal justice system, I witnessed firsthand the emotional toll that separation has on families, the lack of support for incarcerated individuals, and the countless obstacles and limited resources available to help them rebuild their lives upon release. While there are nuances and distinctions in the case of each imprisoned individual, those who are imprisoned for petty offenses too often re-enter a world that lacks the support they need to move forward from their experience.

Following my release, I doubled down on my philanthropic work in criminal justice reform and various “upstream” social causes that help empower and guide people on the right paths. I’ve long been affiliated with groups like Publicolor, which engages thousands of kids each year in education, job training, and the arts. Through Dutchess and my own network, we helped gain clemency for people serving shockingly long sentences and worked to successfully influence legislation for more empathetic treatment of inmates during the pandemic. The list goes on, because the opportunities for improving the system are endless. The hope is to change the lives of individuals and families, and at a macro level, to combine the right mix of resources, organizations, and support networks to bring about a more compassionate and equitable approach to justice.

One of your latest philanthropic efforts is aimed at supporting those incarcerated. What was your vision for co-founding the Prison Visitation Fund, and how do you define its mission and impact?

Through the Prison Visitation Fund, we are committed to being a catalyst for change in the lives of those affected by incarceration. Our focus on family connections and social support not only contributes to the reduction of recidivism, but also instills a sense of hope and empowerment in those we serve. We believe that everyone deserves a second chance, and our work aims to create a pathway towards redemption and successful reintegration into society.

Our primary goal is to address the profound emotional and social toll that incarceration takes on both incarcerated individuals and their families. Extensive research has shown that maintaining strong family ties during incarceration significantly reduces the likelihood of reoffending. Our work offers resources that support family connections and strengthen social bonds – creating a positive impact that extends far beyond the prison walls.

What has your experience taught you about redemption and second chances?

I’m not owed anything. I’ve never felt throughout this process that I deserve a second chance or any deep sense of redemption. This has been my reality, and I’m sure it’s similar for others who need to find ways of moving forward and living with their mistakes. This feeling can make it challenging to wake up and find the motivation to continue putting in the work. Because the idea of redemption is a daily task, struggle, and opportunity, I know I’ll never be done. All I can do is move forward each day, with this sense of purpose and understanding of how I can use my situation to help others.

At the same time, I cannot overlook the profound influence of my family and closest friends who have stood by me unwaveringly throughout the highs and lows. They have been the beacon that keeps me going, reminding me that even in the face of challenges, there are reasons to continue pushing forward and improving not only myself, but also the lives of those around me.

Given the challenges you have overcome, what advice would you offer to others who may be navigating difficult times or seeking redemption in their own lives?

My advice always is to face your mistakes with honesty and humility. Embrace accountability, listen, and find ways to use these opportunities to guide whatever’s next. Surround yourself with supportive individuals, because it will become clear pretty quickly who is most important and who will be there for you. Remember that it’s a process – a long one, but one that starts and ends with deciding to move forward regardless of shame, despair, and regret.