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 March 5, 2019 with the most current information available.

Date Event Location
March 2019 Outperform Podcast
March 26, 2019
3:30 PM
Nichols College
“Learning to Lead” Keynote speaker
129 Center Rd
Dudley, MA
March 27, 2019
2:00–4:00 PM
Middlesex Community College
MILES Keynote Speaker
Bedford, MA
March 28, 2019
11:15 AM
University of Massachusetts Boston
Curriculum Talk
UMass Boston, Boston, MA
April 8, 2019
10:30 AM
The University of Alabama Tuscaloosa, AL
April 11, 2019
11:30 AM
Regis College
Spring ‘19 Signature Event Speaker
Regis College, Weston, MA
April 11, 2019
3:30 PM
Gathering of Titans
Guest Speaker
Dedham, MA
April 16, 2019
6:00 PM
Merrimack College
Curriculum Talk
Andover, MA
April 18, 2019
8:30 AM
University of Massachusetts Amherst
Isenberg School of Management
UMass Amherst, Amherst, MA
April 22, 2019
6:00 PM
Salem State
Agganis Forum Keynote Speaker
Salem, MA
April 24, 2019
4:30 PM
Entrepreneurs Organization & Young Presidents Organization
Guest Speaker
Trade Center 128
Woburn, MA
April 25, 2019
7:00 PM
Colby College
Entrepreneurship Exp Keynote Speaker
Waterville, ME
April 30, 2019
10:00 AM
Lowell Catholic High School
All-school guest speaker
Lowell, MA
May 2019 Humans 2.0 Podcast
May 8, 2019
5:00 PM
The Boston Foundation
Meet Author Bill Cummings
75 Arlington Street
Boston, MA
May 14, 2019
5:30 PM
Developing Leaders Guest Speaker
Boston, MA
May 17, 2019
11:30 AM
Friday Forum
Guest Speaker
May 22, 2019
8:00 AM
Business for Breakfast
Guest Speaker
TradeCenter 128, Suite 1930
Woburn, MA
December 4, 2019 Association of Fundraising Professionals
Annual Conference Keynote Speaker
Copley Marriott

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