We are a small team that excels at our expertise

An agile and fast-moving team that helps our clients excel across investments, acquisitions, mergers, private equity, venture capital and all imaginable business scenarios.
portrait Gordon Caplanportrait Gordon Caplan

Gordon Caplan

Chief Executive Officer
Gordon R. 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 LLC, Mr. Caplan was the Co-Chairman of Willkie Farr & Gallagher LLP from 2015 to 2019. He led the private equity practice and built one of the largest private equity practices in the world. Mr. Caplan was the Chair of the Private Equity Practice at Willkie Farr & Gallagher LLP 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.

Mr. 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.

Mr. Caplan received a JD from Fordham Law School in 1991, where he was an Editor of the Fordham Law Review in 1990, and a BA from Cornell University College of Arts and Sciences in 1988. Mr. Caplan is a member of Fordham's 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.

Gordon also serves as a voice for criminal justice reform, spearheading the Prison Visitation Fund (prisonvisitationfund.org), a non-profit dedicated to keeping families together during a loved one’s period of incarceration.
photo Anna White

Anna White

Chief Operating Officer
Anna has over 25 years of experience including operations management, human resources management, leadership and professional experience.  Prior to joining Dutchess, Anna worked as the Private Equity Practice Coordinator at Willkie Farr & Gallagher.   Anna worked at Willkie Farr & Gallagher from 2002 through 2020.
photo Joon Park

Joon Park

Joon has over 30 years of experience in managing finance and operations at technology enterprises. Joon ran Finance for AGENCY.COM’s (formerly NASDAQ: ACOM) European division until 2003 and has been investing in and working with startups ever since. An avid student of the history of the internet, Joon spends a lot of time reading and thinking about emerging technology trends like cloud/mobile computing, AGI, and blockchain/web3.
photo Bill Baroni

Bill Baroni

Bill Baroni is an attorney, law professor, former college board Chairman, former State Senator, and was the co-head of the Port Authority of New York and New Jersey, where he oversaw New York and New Jersey's transportation infrastructure and the rebuilding of the World Trade Center. Bill brings more than 20 years of governmental and non-profit experience to Dutchess, where he is involved in identifying solutions to some of the most complex problems that face our diverse clientele.
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Blair Flicker

Blair Flicker joined Dutchess Management in January 2024.  Prior to joining Dutchess, Blair was a Managing Director and General Counsel at Insight Partners.  He worked at Insight from 2001 through 2023 and managed all legal activities of the firm. Prior to joining Insight, Blair worked at Johnson & Johnson in New Brunswick, NJ for nine years, and before that was an associate at the law firm of Skadden, Arps, Slate, Meagher & Flom. Blair received a BA in Economics from Tufts University, a JD from Columbia Law School, and an MBA from Columbia Business School.
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photo Gerard Mattia

Gerard Mattia

Gerard has over 30 years of experience in financial services, having served in several C-Suite roles in both the US and UK. Gerard was most recently Chief Risk Officer for HSBC North America, Inc., and before that, was Chief Financial Officer of HSBC Holdings’ global investment bank from 2010 to 2019. Gerard brings extensive experience across finance and risk disciplines to Dutchess, helping clients develop strategies to address evolving market developments and regulatory requirements, solve complex issues, assess and execute against business opportunities and drive efficiencies.
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photo Lucky Yona

Lucky Yona

Vice President
Lucky is a keen technologist and analyst with a background in financial services, entrepreneurship, and analytics. At Dutchess, Lucky works on market research, implementing processes and tools, and strategic support for Dutchess and our clients. He graduated from Yale with a B.A. in Economics.
photo Aditya Singhal

Aditya Singhal

Senior Associate
Aditya joined Dutchess in 2022 with a background in engineering and business. Here, he explores investment opportunities, financial modeling, and go-to-market & growth strategies. He holds a Masters in Business Management from the Ross School of Business.

Demola Ladokun

Senior Associate
Demola is an investment analyst currently serving as a Senior Associate at Dutchess. He has a strong financial risk management and data analytics background. He is well known for combining analytical expertise with strategic thinking to drive business success for our clients while being a collaborative problem solver with a passion for continuous learning and knowledge sharing.
Prior to Dutchess, he worked as a Financial Risk consultant within the Risk Advisory division at KPMG, where he made a solid impact on some of the leading financial institutions in Africa.
Demola obtained his master’s in Engineering Management from Dartmouth College and holds a BSc in Industrial Engineering from the University of Ibadan.
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photo Isaac Harris

Isaac Harris

Isaac joined Dutchess in 2022 with a background in legal research, entrepreneurship, and policy analysis. At Dutchess, he explores new markets and opportunities for the firm and its clients. He holds a B.A. in Legal History from Stanford University.
photo Michael Tuvshinsaikhan

Michael Tuvshinsaikhan

Michael joined the Dutchess team in 2022 with a background in economics and legal research. At Dutchess, Michael handles investment research and client relations along with exploring new opportunities and solutions for the firm as a whole. He holds a B.A. in Economics and Philosophy from the University of Chicago.

Naoise Mooney

Manager of Operations
Naoise joined Dutchess in 2022 with abackground in financial administration, sales and marketing.  Naoise isthe manager of operations, where she assists with the coordination andexecution of various tasks within the company to ensure the smooth operation ofour day-to-day activities. Naoise holds a B.A. in Modern Irish and WorldReligions and Theology from Trinity College Dublin, Ireland.
photo Vlad Tobar

Vlad Tobar

HR & Accounting Coordinator
Vlad has background in entrepreneurship, and management. He graduated from LIU Brooklyn with a B.A. in Business Management.