Carolyn Wilman founded Imagination Edge Inc.* in 1994 as a small-business marketing consulting firm.  She created On-Demand and Relief Marketing services allowing small companies to obtain the experience and personalized services of a professional marketer without the financial commitment of a marketing department or adding additional full-time staff.


In 2004, after spending two years managing the back end of the business as well as being a stay-at-home mom, Carolyn took the love of her contesting hobby and combined it with her extensive marketing background.  The result was the first Internet-focused contest resource book in Canada called You Can’t Win If You Don’t Enter, released in 2006.  In conjunction with the book, she launched Contest Queen, the hub of all things contesting, the first contest resource website with links to contesting sites, groups and forums, contest management companies, contesting software, and more. The American Edition of You Can’t Win If You Don’t Enter was released in 2008.  To date, her Online Contesting System has helped others win over $1,000,000 in cash and prizes. The 2nd Edition, How To Win Cash, Cars, Trips & More! was published in 2016. The 3rd Edition: Prizes, Prizes, Everywhere! will be published in 2021.

In keeping with her objective of teaching others how to have fun, From the Contest Queen is a blog about all things contesting, sweepstaking, lucky & fun, along with her tips, tricks, news, and rants on the hobby.  Additionally, Carolyn runs seminars and webinars: How to Win Cash, Cars, Trips … & More! and Attracting Luck for hundreds of people annually.

From 2005 until 2011, Carolyn produced The Winning EDGE, a free e-newsletter that included contesting stories, tips, tricks, and links to new contests.  From 2008 until 2010, Carolyn hosted an online radio show, With The Contest Queen, interviewing the movers and shakers in the promotional industry and sweepstaking community. Both were revamped and relaunched in 2013, with The Winning EDGE being sent out bi-weekly and With The Contest Queen only broadcasting special podcasts.  (NOTE: Archives for both the newsletter and radio show can be found online.)

After being a featured speaker at numerous promotional events and U.S. sweepstaking conventions, she formed Canada’s first contesting clubs.  Once several clubs had been firmly established, Carolyn co-founded the Canadian Contestors Association, which ran the Canadian Contestors Convention in 2007. Carolyn, her volunteer team, and the convention were filmed by the CBC for a Doc Zone documentary and written about in Reader’s Digest, both released in 2008. She is currently a lead volunteer for SweepsCon 2017, to be held in Orange County, CA, in July.

In 2013 Carolyn embarked on her first U.S. Tour.  The “Secrets to Winning” Sweepstakes Tour took her through 17 states, hosting workshops in 12 cities and teaching “sweepers” How To Use RoboForm Effectively along with How to Win on Facebook, Twitter, Instagram, and Pinterest by giving away over $6000 in prizes over the course of 4 weeks.

In 2019 Carolyn decided to big up a gauntlet that was given to her in 2008. She bought the rights to all of Helene Hadsell’s work. After being out of print for over 30 years, the first book to be updated and re-published was Contesting: The Name It & Claim It Game. In Contact With Other Realms and Confessions of an 83-Year-Old Sage were re-published shortly after. Her final book, a work of fiction, A Man Called Friday, will be re-published in 2023.


In 2014 Carolyn launched a new venture, Idea Majesty, to meet the growing demands of her social media marketing services and digital online marketing plans. The services offered are drawn directly from Carolyn’s experience as both an entrepreneur and author. Her specialty is helping other small businesses reach their goals and maximize their potential by offering marketing consultation, content creation, and curation, along with community management.

Specializing in sweepstakes marketing, Carolyn has a unique perspective having ‘sat at both sides of the table,’ as both marketer and entrant, she is able to help her clients understand promotions from their customer’s perspective and avoid the types of mistakes currently occurring in contests over and over again.  She created Contest Auditing, Contest Pre-testing, and Contest Education and Strategies services allowing companies to ensure a contest is designed to meet their objectives and the promotion is operating properly, within government regulations, before public release.


Her efforts as a marketing expert landed her on the cover of Marketing Magazine in 2006; she was named by MORE Magazine as one of Canada’s Top 40 Women over 40 in 2007 and was featured in the premiere episode of High Stakes Sweepers on TLC in 2011.

Carolyn was nominated in 2006, 2008, and 2009 for the RBC Canadian Woman Entrepreneur of the Year and in 2006 for Entrepreneur of the Year with the Whitby Chamber of Commerce. You Can’t Win If You Don’t Enter was selected as the Runner-Up in the Non-Fiction Category at the 2006 DIY Book Festival and Runner-Up in the How-To Category at the 2008 DIY Book Festival. In 2008 she received both her Competent Communicator and Competent Leader designations from Toastmasters International. In 2015 Carolyn achieved her Advanced Leadership Bronze designation, and in 2016, her Advanced Communication Bronze designation.

*NOTE: Imagination Edge Inc. was officially closed in 2009.