Host an Event with Bill Cummings

Bill has been delighted to spread his messages of entrepreneurship and philanthropy through numerous speaking engagements. If you would like to invite Bill to speak to your group, please read the information below, and contact us to discuss the possibilities.

Event Format

Many business associations, law firms, investment companies, senior centers, nonprofits, and area colleges have hosted events with Bill and received tremendous positive feedback. To ensure an engaging and interactive experience, most programs are structured as either a Q&A or an interview followed by questions from the audience. Bill is always pleased to remain after the speaking portion to sign books for attendees.

Event Parameters

We do not charge speaking fees, but have created just a couple of requirements for host organizations in order to maximize Bill’s limited time:

  • Ensure a minimum of 200 attendees. Some smaller groups have seen this as an opportunity to collaborate with other local organizations on a larger joint event.
  • Purchase a minimum of 200 books at the discounted rate of $260 per case of 26. (All proceeds go to Cummings Foundation.) Host organizations may provide the books to attendees at no cost or sell them at the retail price and retain the $6.95 per book profit.

To Inquire About Booking an Event

Please contact Cindy Canavan at or 781-569-2344 with three or four possible dates and times to discuss as options.

Thank you for supporting Cummings Foundation in this way, as it helps spread the important message of philanthropy—and 100 percent of the book’s proceeds go to charity.


I have heard countless comments and compliments from alumni, faculty, staff and students about how inspiring your story is and the work that you have accomplished.

Bentley University Alumni Event

I’ve received nothing but positive feedback from those in attendance and the crowd seemed very happy.

Babson College

It was probably the most interesting and most genuine ‘morning program’ I’ve been to in my 22 years of attending them (not just at McLane—across the board).

Attendee at McLane Middleton Law Firm event.

It was a real blessing to have you on campus, and I’ve already heard so much good feedback. We’ll hope for the chance to have you back on campus to speak to our students again.

D. Michael Lindsay, President, Gordon College

In a one-hour session at Boston College, Bill inspired and challenged students from across disciplines with personal anecdotes that illustrate his entrepreneurial-spirit, frugality, and persistence… qualities that led him and his company to excellence. His business and philanthropic pursuits are an inspiration to students. His is a remarkable story and he conveys it in a comfortable and accessible manner.

Neil McCullagh, Executive Director, Corcoran Center for Real Estate and Urban Action, Carroll School of Management, Boston College

To purchase Starting Small, use the dropdown menu here.

Bill Cummings’ Upcoming Personal Appearances

Last updated May 23, 2019 with the most current information available.

Date Event Location
May 2019 Humans 2.0 Podcast
June 12, 2019
6:30 PM
Summer Soirèe for the Shattuck—Gala 2019
Keynote Speaker
Venezia Restaurant
20 Ericsson St., Boston
June 27, 2019 Forbes 400 Summit on Philanthropy
Featured Speaker
New York City
November 20, 2019
12:00 PM
Metro South Chamber of Commerce
Annual Conference Keynote Speaker
Brockton, MA
December 4, 2019 Association of Fundraising Professionals
Annual Conference Keynote Speaker
Copley Marriott
December 11, 2019 New England Real Estate Journal Hilton—Woburn
January 28, 2020
11:45 AM
En Ka
Guest Speaker
Church of the Epiphany
Winchester, MA

Prior Appearances

Date Event Location
May 22, 2019 Business for Breakfast
Guest Speaker
Woburn, MA
May 17, 2019 Friday Forum
Guest Speaker
May 14, 2019 NAIOP
Developing Leaders Guest Speaker
Boston, MA
May 8, 2019 The Boston Foundation
Meet Author Bill Cummings
Boston, MA
April 30, 2019 Lowell Catholic High School
All-school guest speaker
Lowell, MA
April 25, 2019 Colby College
Entrepreneurship Exp Keynote Speaker
Waterville, ME
April 24, 2019 Entrepreneurs Organization & Young Presidents Organization
Guest Speaker
Woburn, MA
April 22, 2019 Salem State
Agganis Forum Keynote Speaker
Salem, MA
April 18, 2019 University of Massachusetts Amherst
Isenberg School of Management
Amherst, MA
April 16, 2019 Merrimack College
Curriculum Talk
Andover, MA

Date Event Location
April 16, 2019 Elevate Podcast
April 11, 2019 Regis College
Spring ‘19 Signature Event Speaker
Weston, MA
April 11, 2019 Gathering of Titans
Guest Speaker
Dedham, MA
April 8, 2019 The University of Alabama Tuscaloosa, AL
March 28, 2019 University of Massachusetts Boston
Curriculum Talk
Boston, MA
March 27, 2019 Middlesex Community College
MILES Keynote Speaker
Bedford, MA
March 26, 2019 Nichols College
“Learning to Lead” Keynote speaker
Dudley, MA
March 2, 2019 Saïd Business School
Entrepreneurship Forum Speaker
University of Oxford, England
February 20, 2019 Breakfast Group
Guest Speaker
Boston, MA
February 2019 Boston Now Podcast with Kim Carrigan
February 5, 2019 Northeast Arc/DECA Partners
Black Box Theatre Presentation
Peabody, MA
February 5, 2019 Wentworth Institute of Technology
Curriculum Book Talk
Boston, MA
February 4, 2019 Winning Business Radio
Guest Interview
January 31, 2019 Cathedral High School
Leadership Series Speaker
Boston, MA
January 23, 2019 Agahozo-Shalom Youth Village
Guest Speaker
Rubona, Rwanda
January 22, 2019 University of Rwanda
Leadership Talk
Kigali, Rwanda
November 28, 2018 Suffolk University
Book Talk
Boston, MA
November 28, 2018 University of Massachusetts Lowell
Business School Event
Moloney Hall
November 20, 2018 Porter Square Books Cambridge, Book Talk Cambridge, MA
November 15, 2018 Entrepreneurship for All Summit, Keynote Speaker Lowell, MA
November 8, 2018 UTEC/Si Se Puede
Lawrence MA
October 27, 2018 Asian Task Force Against Domestic Violence
“Community Heroes” Keynote Speaker
October 25, 2018 Bloomberg Radio
Baystate Business
106.1FM/1330 & 1450AM
October 24, 2018 Bentley Executive Club
Entrepreneurs Among Us
Waltham, MA
October 23, 2018

Boy Scouts of America
Hall of Fame Speaker

Milton, MA
October 22, 2018 Salem State
Strategic Entrepreneurship
Salem, MA
October 22, 2018 Beverly Education Foundation
Public Event
Beverly, MA
October 19, 2018

Tufts University
Founders Workshop Keynote Speaker

Medford, MA
October 17, 2018 Endicott College Business and Entrepreneurship Guest Speaker Beverly, MA
October 15, 2018 The Carroll Center for the Blind
“Never Limit Your VISION and PASSION
Newton, MA
October 15, 2018 Boston College
Corcorcan Center for Real Estate and Urban Action
and the Shea Center for Entrepreneurship
Chestnut Hill, MA
October 12, 2018 “Chronicle” Feature WCVB Channel 5
October 10, 2018 Westford Business Association
Distinguished Speaker
Westford, MA
October 10, 2018 Friends of Chevalier Theatre
Arts Across Medford Guest Speaker
Medford, MA
October 8, 2018 Gordon College
Entrepreneurship Campus Event
Wenham, MA
October 2, 2018 Mass Maritime Academy
Distinguished Speaker
Buzzards Bay, MA
September 20, 2018 The Jenks Center
"Bill Cummings Presents: Starting Small and Making It Big"
Winchester, MA
September 18, 2018 Medford Public Library
"Starting Small and Making It Big"
Medford, MA
Sept 12, 2018 Fidelity Associates' Inspiration Luncheon Speaker Seaport, Boston
Sept 11, 2018 Emmanuel College
Distinguished Speaker at Academic Convocation
September 6, 2018 BEAT (Biomedical Entrepreneurs at Tufts)
Entrepreneurs Among Us: Bill Cummings
Tufts University
August 22, 2018 New Horizons at Choate Book Talk Woburn, MA
August 8, 2018 Junior Achievement JA Summer Institute Speaker Cambridge, MA
July 18, 2018 Pingree School
Guest speaker
July 10, 2018 McLane Middleton Law Firm
Guest Speaker at Community Forum
Woburn, MA
June 28, 2018 Cummings Center
Meet Founder and Author Bill Cummings
Beverly, MA
June 27, 2018 New Horizons at Marlborough
Book Talk
New Horizons at Marlborough
June 26, 2018 Dimock President's Council Reception
Conversation hosted by WBUR's GM Charlie Kravetz
June 20, 2018 Merrill Lynch
After Hours Event
June 20, 2018 Bentley University Alumni Summit Keynote Speaker:
"An Afternoon Focus On Entrepreneurship"
LaCava Center
June 13, 2018 The Philanthropy Connection
Distinguished Speaker
June 12, 2018 Woburn Historical Society
"Transforming Woburn into the 21st Century"
Woburn, MA
June 6, 2018 Medford High School Graduation
Commencement Speaker
Medford, MA
May 31, 2018 The Giving Pledge  
May 24, 2018 Woburn Business Association
Lunch & Learn Series
Woburn, MA
May 18, 2018 Associated Industries of Massachusetts
Vision Award
The Westin Boston Waterfront
May 14, 2018 Anna Maria College
Bill and Joyce Cummings accepting honorary degrees
Worcester, MA
May 1, 2018 WBZ AM 1030 Radio news coverage

WBZ AM 1030

April 25, 2018 Babson College: Cutler Center Thought Leadership Series:
Babson College - Olin Hall
April 24, 2018 "Greater Boston" with host Jim Braude WGBH Channel 2 broadcast
April 20, 2018 WBZ-TV Channel 4 News feature WBZ-TV Channel 4 broadcast
April 17, 2018 "Nightside with Dan Rea" on WBZ AM 1030 Radio WBZ AM 1030 Radio podcast
April 6, 2018 "Off the Shelf" with host Veronica Andrews

Danvers Community Access TV broadcast

April 4, 2018 NECN Business with Brian Burnell

New England Cable News

April 4, 2018 and
April 5, 2018
Tufts Entrepreneurship Leadership Program Awards Ceremony Tufts University
March 10, 2018 Author Event at Book Ends bookstore Winchester, MA

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