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Entering Contests with Photos

Carolyn — Mon, 03 Aug 2026 12:00:20 +0000

KEEP YOUR PHONE CHARGED AND READY Summer is the perfect time to start building your contest photo library! While you're enjoying the sunny weather, family vacations, and outdoor activities, you can capture images that will serve you well for contests throughout the entire year. From back-to-school moments in August to Halloween decorations in October, Thanksgiving [...]

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WIN Your Spot at my Sweepstakes Masterclass!

Carolyn — Sun, 02 Aug 2026 12:00:39 +0000

Every month, I give away 25 spots to a sweepstakes masterclass so contestors can overcome their giveaway hurdles and master the art of winning! In the past, I have taught others how to: organize their sweepstakes, enter on Facebook, find X/Twitter contests, tag friends on Instagram, create TikToks set up RoboForm, source local giveaways. The [...]

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Is Your Smartwatch Helping You Win Sweepstakes?

Carolyn — Wed, 29 Jul 2026 12:00:06 +0000

Sometimes I do things automatically and don't realize they aren't common knowledge. That happened during my recent Sweepstakes Q&A livestream. My smartwatch kept going off while I was live. Even though I had put my phone on silent, my watch was still letting me know whenever someone posted in one of my sweepstakes groups. Afterward, [...]

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Another Sweeper’s Convention Experience

Carolyn — Tue, 21 Jul 2026 12:00:34 +0000

You may know Tom Cavalli, as he is both a sweeper and the owner of iWinContests. He created a video with his take on all of our shenanigans and fun in Scottsdale, AZ, at the 37th Annual National Sweepstakes Convention. As people frequently ask me what happens at a convention. I believe it's a good idea [...]

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The 37th Annual National Sweepstakes Convention — Part 2

Carolyn — Tue, 14 Jul 2026 12:00:05 +0000

There were too many adventures for one blog post. This is Part 2 of my winning adventures in Scottsdale, Arizona, at the Annual National Sweepstakes Convention. (Read Part 1.) Day 5 — Saturday, July 11th Today was the big luncheon banquet, and it didn't start until 11:00 AM, so we got to relax in the [...]

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The 37th Annual National Sweepstakes Convention — Part 1

Carolyn — Sat, 11 Jul 2026 12:00:12 +0000

The 37th Annual National Sweepstakes Convention was held in Scottsdale, Arizona, for the fourth time. It was first hosted here in 2006, the second convention I ever attended. It was also here in 2021 and 2023. Day 1 — Tuesday, July 7th I have learned that I always like to arrive early and leave late, [...]

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The Sweepstakes World Has Changed—And So Must You

Carolyn — Fri, 03 Jul 2026 12:00:32 +0000

When I started sweepstaking in 2001, I never imagined how different this hobby would look today. Back then, we had radio call-ins (remember frantically dialing when you heard your cue to call?), in-person giveaways at the mall, those trusty mail-in entries, and a handful of basic online sweepstakes that were basically digital versions of paper [...]

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Master Winning Sweepstakes With Me for FREE!

Carolyn — Thu, 02 Jul 2026 12:00:04 +0000

Every month, I give away 25 spots to a sweepstakes masterclass so contestors can overcome their giveaway hurdles and master the art of winning! In the past, I have taught others how to: organize their sweepstakes, enter on Facebook, find X contests, tag friends on Instagram, create TikToks set up RoboForm, find local giveaways. The [...]

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What Really Happens at a Sweepstakes Convention?

Carolyn — Tue, 23 Jun 2026 12:00:39 +0000

One of the biggest surprises I had when I started writing You Can't Win If You Don't Enter was discovering that sweepers don't just connect online. They also gather in person. READ: Yes, There Are Sweepstakes Conventions! Back in 2004, while researching my first book, I stumbled across the Annual National Sweepstakes Convention. At the [...]

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Voting Contests

Carolyn — Tue, 16 Jun 2026 12:00:47 +0000

As I worked on Prizes, Prizes, Everywhere!, I got to the part where I talk about voting contests. It reminded me of how many times I skimmed the rules vs. read them, and how that got me into contest trouble. As I repeat often, my number one tip is: ALWAYS READ THE RULES [& FOLLOW [...]

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