Following his graduation from the University of Minnesota-Twin Cities, Mackay became an envelope salesperson for Quality Park Envelope Company. He also joined Minneapolis’ Oak Ridge Country Club, where he played golf with area businessmen. In 1984, Mackay and other Twin Cities business leaders purchased thousands of
Minnesota Twins tickets to block owner
Calvin Griffith from selling the team to outside investors and relocating it. In 1985, the Mackay Envelope Company introduced the Photopak, an envelope that holds processed photo prints, and became an industry leader for this product. The company created the MackayMitchell Photopak division, privately owned by Harvey Mackay and Scott Mitchell, and today is the largest North American supplier of photo envelopes. In 2002, MackayMitchell Photopak purchased the photopackaging division of Mailwell Envelope. MackayMitchell Envelope Company employs 500 employees, produces 25 million envelopes a day with sales of $100 million. In 1988, Mackay wrote his first book,
Swim with the Sharks without Being Eaten Alive (
William Morrow and Company). It was on the
New York Times bestsellers list for 54 weeks and has sold over 5 million copies. Mackay began his public speaking career following the release of
Swim with the Sharks. Mackay's second book,
Beware the Naked Man Who Offers You His Shirt, was published in 1990 (Ballantine Books) and reprinted in August 1996. It reached number one on the
New York Times bestsellers list on February 25, 1990. The New York Times listed both books in its top 15 most motivational books of all time in August 1996. In 1993, Toastmasters International named Mackay one of its top five speakers in the world. His third book,
Dig Your Well Before You’re Thirsty, was published in April 1997 and was a
New York Times bestseller for five months. The following year, in December 1998, Ballantine Books published
Pushing the Envelope, his fourth
New York Times bestseller. In 2000, Mackay sold Mackay Envelope Company to a management group. He remains an equal partner and chairman of the company. Later that year, Ballantine Books released Mackay's fifth
New York Times bestseller,
We Got Fired! . . . And It’s the Best Thing that Ever Happened to Us. It was Mackay's third book to reach number one on that list. Portfolio Penguin released his next book,
Use Your Head to Get Your Foot in the Door, his sixth
New York Times bestseller, in February 2010.
The Mackay MBA of Selling in the Real World, his seventh
New York Times bestseller, was released in November 2011 by Portfolio Penguin. Mackay's business thoughts have appeared in
Forbes, the
Harvard Business Review, Inc. magazine,
Reader's Digest, Success magazine, and the
Wall Street Journal, among other publications. He started writing a weekly column for
United Feature Syndicate in 1993, which is published in major newspapers across the country.
Andrews McMeel is now syndicating his column. He has appeared on various national shows, including
Larry King Live,
The Oprah Winfrey Show,
Good Morning America,
Fox and Friends, and
The Today Show, among others. ==Civic experience==