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Updated: August 22, 2022 / 40 Under Forty, Class of 2022

40 Under Forty 2022: Tom Cunningham

Photo | Erika Sidor Tom Cunningham
Photo | Erika Sidor 40 Under Forty 2022 winners Billie Kenyon, Tom Cunningham, Matt Majikas, and Liz Estabrooks pose at Polar Beverages in Worcester (special thanks to Chris Crowley)
Tom Cunningham, 37
  • Title Managing director
  • Company Cunningham & Associates, LLC, in Worcester
  • Residence Holden
  • Birthplace Framingham
  • Colleges UMass Dartmouth, University of Phoenix
Click here to read about the other 40 Under Forty, Class of 2022
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Not only has Cunningham’s business grown 750% during his time as managing director, but Cunningham himself plays an essential role in supporting Central Mass. small businesses with taxes and financial services.

As an expert in tax resolution and an enrolled agent, Cunningham helps small business owners gain financial stability. During COVID-19, he helped businesses make the most of employee retention tax credits, accessing more than $1 billion in government aid. He is a leader in management strategy and operational systems, and he is able to mentor other business owners in these fields.

Outside of his work, Cunningham volunteers at a number of organizations in the region, including the Worcester Public Library and the Boys & Girls Club of Worcester. He is the president of C&A Cares, a nonprofit organization aimed at encouraging other Cunningham & Associates employees to volunteer their time. He started the Alex Roper Scholarship for the Trades, which supports people entering the trades in Worcester County. 

What four people would you take on a 10-year, deep-space mission? Neil Armstrong, Neil deGrasse Tyson, Vince Neil, and Tom Brady

What Central Mass. historical figure do you most admire? Robbert Goddard, a true pioneer of innovation

Who is most responsible for the person you are today? My dad. He’s my role model, mentor, and golf coach.

When do you want to retire? Never

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