September 22, 2011

How to enter sweepstakes and win! Sweepstakes 101

Winning prizes through sweepstakes and contests is very simple and if someone is going to win – it might as well be you! We post current sweepstakes here and we want you to win – so if you’re new to sweepstakes, read this tutorial to get up to speed and start sweeping!

The sole purpose of sweepstakes is to generate buzz about a company and acquire new customers. A lot of times sweepstakes will be sponsored by a company. They are paying for the sweepstakes prize and in return they get buzz about their brand, they get new customers to their Website or Facebook page and they acquire new customer contact information – emails, addresses, etc. That’s the reality of it.


Online – This is probably the most common and easiest type of sweepstakes to enter. You complete a basic form with demographic information (name, address, email, birthdate, etc.) and hit submit. It’s that easy! This is how I won my trip to New York!

Mail-in – These types of sweeps aren’t as common, but they are good to enter because your chances are generally better because people don’t go through the hassle of mailing in an entry. Most online sweepstakes have a mail in option (either as an additional entry or as your main entry) and you just need to read through the Sweepstakes rules to get the instructions for mail-in options.

Instant win games – These are online sweeps that you enter with the option of instantly winning! It’s computer generated and completely random. A lot of times the instant win game will be part of a larger sweepstakes, so even if you don’t win instantly you can be entered to win the larger prize as part of the main sweepstakes.


Never pay to enter a sweepstakes, or claim winnings – You should NEVER pay to enter a sweepstakes and NEVER pay to claim your winnings. Even sweepstakes that require a proof of purchase are required by law to have an option available that does not require a purchase. For example, they might allow you to mail in a self-addressed stamped envelope and request an entry into a sweepstakes. But you should never have to pay to enter a sweepstakes or pay to CLAIM YOUR WINNINGS. Ever.

Night owls have the advantage – I’m not sure how I feel about this one, being a morning person, but I understand the best time of day to enter instant win contests is between 11 p.m. and 3 a.m. (when fewer people are entering).

Be consistent – Although it only takes one entry to win, if it’s a sweeps that allows a daily entry, return to enter regularly (either daily or several times of week) for daily entry contests. Every time you enter you are increasing your odds of winning. If you have a lot of contests you want to enter and know that you don’t have time to enter them all daily, choose some favorites to focus on and enter those every day.

Know the rules – Every sweepstakes has RULES, it’s required by law. Look for a link that says “sweepstakes rules” – although it looks like a lot of mumbo-jumbo legal-eeze (and a lot of it is) you can see a.) who is eligible to enter b.) how often you can enter c.) any additional requirements or options for entering.  By reading the rules, you won’t re-enter a one time entry contest and disqualify yourself from the contest. It will also keep you from entering contests that aren’t a good fit for you.


Win it? Record it. Keep good records of your winnings and their value.  I keep a spreadsheet listing what I won, when I won it, what kind of contest was it (Facebook, daily entry, one time entry, etc.) and the value of the prize. Check with your accountant, but you should pay taxes on any winnings (no matter how small). Report your winnings on your tax return. The government considers prizes as extra income.

Make it easy – use Roboform! Roboform is a program that saves all your information and automatically fills out forms for you! It’s super easy to use and can save you a TON of time, on sweepstakes and even when you request coupons or FREE samples. It can keep track of your passwords, have multiple users (so you can enter for family members) and it’s super secure. It costs anywhere from $9.95-$19.95 and I think worth every penny.

If your email starts getting clutter with e-newsletters from companies because of sweepstakes you can unsubscribe after you’ve entered. That’s what I do – if I don’t find useful content in their e-newsletters I’ll unsubscribe after the fact. But then again you can find out about future sweepstakes by staying subscribed, so your call.


Don’t enter a one–time entry contest more than once.  It happens sometimes, but once it happens, don’t plan on winning that prize, you’ve just disqualified yourself.

NEVER enter a contest that asks you to pay. Contests that ask for money are a scam.

Don’t give up! It takes patience and perseverance to win at sweepstakes regularly.  Winning tends to come in spurts with lots of dry spells where you aren’t winning anything.  If you keep entering consistently, eventually you should start winning again.

Don’t forget to check your email and mail! Contests will contact winners via email and require a little more information from you before confirming your winning status. Or they also may send you an affidavit via the USPS (which usually needs to be signed and notarized).  If you fail to respond to these in a timely manner you will be forfeiting your prize and they’ll move on to another winner. Be cautious when responding to emails – make sure it’s for a sweepstakes you entered and never send credit card or payment information.

Don’t just enter to enter. This is my personal rule:  I don’t enter any contest with a prize that I don’t like.  I will enter a contest if the prize is something I can use, I can give to someone else or is useful in some way to me.  If it doesn’t fit that criteria, I skip it and leave for the people who would love to win it. By being selective about the sweepstakes you select you won’t get burned out.


  1. Set up an email specifically for entering sweepstakes.  It helps you spot emails that you need to respond to in a timely manner and it keeps your family (or personal email) from becoming too cluttered. Use a FREE email like
  2. Use a simple spreadsheet (or notebook) to keep track of your winnings.
  3. Enter sweepstakes daily (or at least on a regular basis). Don’t feel pressure or get obsessed – just enter when it works for you. It only takes one entry to win!
  4. Be intentional about the info you share. A lot of forms won’t require all fields be completed. If you don’t want to disclose your income (and it’s not required) don’t. And if you ever feel like you are sharing too much – don’t, no sweepstakes win is worth that.
  5. Read the rules. Every sweepstakes is required to have one.
  6. Report your winnings on your taxes. It’s required by law and no one wants to get audited by the IRS for failing to report earnings.
  7. Consider entering contests that give back. I like to enter contests that support the schools in my area or my community. Sometimes there’s a prize for me, but a lot of times it’s a prize for the school or community.
  8. Be patient! It may take weeks or even a few months before the sweepstakes you are entering now will be notifying winners. When I won my trip to New York, I entered in March or April of 2010, didn’t find out until September 2010 and didn’t get my trip until July 2011! But totally worth the wait.

ONE LAST THING . . .Once you start winning, enjoy your prizes!  You’ve earned them. And PLEASE let me know if you win, email me thehive (at) (remove spaces) or contact me here and let me know what you win. I’d love to have a picture, too – I want to start a winner’s circle page with wins!

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