I finally met Margo! She has been following me, and been my contest buddy for over five years.

I was sure I would meet her before now as she:

  1. enters almost all the same Toronto-based event contests.
  2. entered every Meet The Queen contest I ever held.
  3. occasionally invites me along as her +1 if she has an extra ticket.

I clearly remember being shocked at one contest drawing I held. There were only a handful of entries. I was sure her name would be picked. (I use the random draw feature in Woobox for my Facebook contests so all my drawings are fair.) Obviously, she didn’t win. Somehow, in the last contest I held, she was the only entrant!

As for being her plus one … timing is always terrible. I was always booked or busy on the day.

We are both busy so we picked a quiet time, mid-day and mid-week to meet.

Dundas and CarlawI was finally able to use the Dundas and Carlaw gift card I won. What a cool little place. Not only does the coffee shop have liquor license, but it is TTC themed with all types of cool signage and decor.

We ate and chatted for two hours. The conversation turned to sweepstakes and I discovered Margo’s biggest contest challenge: disorganization.

To me being organized is a biggest key to winning. It allows you to enter the most number of sweepstakes in the shortest amount of time. Plus, if you are short on time, you know which are the most important prizes for you to get in on for that day.


Be sure to follow me on Facebook for your chance to win as I hold court in my hometown and whenever I travel. If you can’t wait, enter my monthly giveaway for a custom one hour mastermind session with me.

What is your biggest contesting challenge?