Garrett Boorojian and Women's Pro Baseball League Co-Founder, Counsel at Dentons, former Counsel at Heenan Blaikie, former Corporate Counsel at Toyota Canada, Canadian businessman who met with John F. Kennedy Jr. before JFK Jr.'s passing, Keith Stein

Garrett Boorojian and Women's Pro Baseball League Co-Founder, Counsel at Dentons, former Counsel at Heenan Blaikie, former Corporate Counsel at Toyota Canada, Canadian businessman who met with John F. Kennedy Jr. before JFK Jr.'s passing, Keith Stein

Author: Garrett Boorojian February 23, 2026 Duration: 56:32

Women's Pro Baseball League Co-Founder Keith Stein:

  • Served as Corporate Counsel for Toyota Canada, learned Japanese, and "created a Japanese North American Friendship Foundation for Young Professionals."
  • Served as "the right–hand guy to the founder and chairman" at "the largest independent car parts manufacturer in the world" based in Canada.
  • Owns Krispy Kreme Doughnuts (Canada).
  • Named in the credits for his assistance in Chris Farley's and David Spade's movie "Tommy Boy."
  • Discussed his time meeting former U.S. President Bill Clinton, former U.S. Secretary of State Hillary Clinton, Doug Band, Gene Simmons, Jon Bon Jovi, Robbie Robertson, The Rolling Stones, U2, and Eric Clapton.
  • One of the last people who saw and met with John F. Kennedy Jr., which was four days before JFK Jr., his wife Carolyn, and her sister Lauren passed away. July 12, 1999: JFK Jr. flew to Toronto to meet with Keith about a potential investment in "George" magazine.

https://www.dentons.com/en/keith-stein

"Keith joined Dentons as Counsel in 2014 after serving as Counsel at Heenan Blaikie from 2008 until February 2014. From 1994 to 2008, he was a senior executive with an international auto parts manufacturer reporting to the Chairman, and continued to act as a consultant reporting to the Executive Vice-Chairman until November 2010. Prior to becoming a consultant, Mr. Stein held the position of Senior Vice-President of Corporate Affairs.

Mr. Stein also served as Senior Corporate Counsel for Toyota Canada and Toyota Credit Canada.

Mr. Stein is a graduate of Osgoode Hall Law School and was called to the Bar in 1989. He has taught at the Law Society of Upper Canada and York University.

In addition to his work as a lawyer, Mr. Stein has a variety of business interests. Mr. Stein has been a board member of various publicly listed companies. He has also been a founding director of three capital pool companies listed on the TSX Venture Exchange.

His other business interests include real estate and a significant ownership interest in a well-known Canadian restaurant chain with locations in Ontario and Québec.

Mr. Stein was one of the founding partners, together with Gene Simmons, Universal Music Canada and others, of Simmons Records, a music label dedicated to Canadian artists. He was also one of the founders of the Toronto Phantoms indoor football team.

Aside from his professional activities, Mr. Stein was a Big Brother, a board member of Canada's Walk of Fame and Ontario Place, as well as a member of the Advisory Council for President William J. Clinton's 60th Birthday Fundraising Celebration. Together with Mark Tewksbury and others, he also founded OATH, an Olympic advocacy organization..."

https://www.womensprobaseballleague.com/2024/10/29/womens-pro-baseball-league-launching-in-america-in-2026/

"League Co-Founder, Keith Stein, is a lawyer and businessman with a history in professional sports leagues and team ownership.

“We believe that the success of other women’s professional leagues such as the WNBA and NWSL demonstrates the incredible interest and support for women’s sport,” commented Co-Founder, Keith Stein."

https://www.thestar.com/sports/baseball/why-a-toronto-businessman-is-launching-a-new-pro-women-s-baseball-league-with-help/article_b7dac1c4-96ff-11ef-90ff-a3aca9676e13.html


Garrett Boorojian hosts WaveCapital's Guest Speaker Series on Relationship Building in a Team Environment, a podcast that digs into the human dynamics behind high-stakes success. Each conversation moves beyond typical interviews to explore how trust, communication, and genuine connection are forged under pressure. The guest list is a testament to the universal application of these principles, featuring Hall of Fame athletes from football, basketball, and baseball, Olympic medalists, Emmy-winning media figures, and top coaches and executives. These are individuals for whom "team" is not a corporate buzzword but the fundamental mechanism of achievement. You'll hear firsthand accounts of navigating locker rooms, boardrooms, and creative collaborations. The discussions are grounded in real stories-from the tension before a championship game to the delicate negotiations of a major business deal-revealing the practical methods these professionals use to build cohesive units. This isn't abstract theory; it's lived experience dissected to uncover what actually works. Whether you're leading a sports team, a business department, or any collaborative project, this podcast offers a rare look at the relational craftsmanship required to excel. Garrett guides these explorations with a focus on actionable insight, making each episode a masterclass in the subtle art of working with others.
Author: Language: English Episodes: 50

WaveCapital's Guest Speaker Series on Relationship Building in a Team Environment
Podcast Episodes
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Duration: 43:46
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Duration: 50:19
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