iWIN Live Interview Edition with Steve Dadolf

Come learn more about sweepstakes as we interview someone that has won over 4 times as many trips as iWIN Tom!

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iWIN Live Interview Edition with Walt from KY

Walt and Tom chat about skilled contests. These are contests that are judged for a winner.

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iWIN Live Interview Edition

We interview a mystery guest that just won a truck!

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iWIN Live Interview with Junior Chicago Bears Reporter

The winner of the Junior Bears Reporter joins us to talk about winning and her love of the Chicago Bears!
 
 
 
 

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iWIN Live Interview with Harriet Brown

This was filmed back in 2019. One of my favorite iWIN Interviews of all time
 
 
 

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iWIN Live Interview Edition

This was recorded May 2020 — Lets you see what it is like living with a sweeper!
 
 

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iWIN Live Interview Edition

Meet two of our younger sweepers and listen to their adventures!
 

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iWIN Live Interview with a 7 time Game Show Contestant

iWIN Live with a 7 time Game Show Contestant

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96 Year old Harriet tells her winning stories!

iWIN Live interview with Harriet Brown – LIVE from Arizona 2023

Testimonials

iWIN has sweepstakes that none of the other newsletters have! They find the most winnable sweeps and help you win.

Sheila | Maryland

Thanks iWINContests for helping me win $1500!

Amy | Texas

One of our most memorable wins was a NASCAR VIP weekend at Talladega Speedway that included a personal Meet & Greet with Danica Patrick, who is one of our favorite drivers. We chatted for nearly an hour, what a sweet person.

Linda | North Carolina

I would like to thank you for all the contests you find for us. Here is a picture of myself, husband and two great friends at a Buffalo Bills game yesterday. I won four tickets from the BudLight contest you told us about. Thanks again for all you do, we...

Theresa | New York

Yes, I DO like iWIN – I find sweeps that I had not found otherwise, or that slipped my mind. I DID win a trip through iWIN that I did not see anywhere else. When sweeping friends discuss newsletters, I always remember to tell them about iWIN!

Elizabeth | California

I signed up for the iWIN newsletter and the very first week I won a Petco $100 gift card. Max was so happy! I really look forward to the newsletter every Thursday!

Donna | New York

I really enjoy receiving iWINContests Newsletters for sweepstakes information on limited or few entries. It gives the subscriber an extra edge on getting in on a quickly closing contests and the best possible to win sweepstakes. All Social media chances are listed for those who like to enter through those...

Lori | Arkansas

I can’t wait for the next issue of iWINcontests to arrive! It’s filled with unique, something for everyone, easy to read contests. The ease of receiving the newsletter by e-mail makes entering a breeze and the FB site keeps me connected with other subscribers. I highly recommend iWINcontests for everyone!...

Patty | Ohio

Tom and iWIN helped me win this lawnmower in a one day sweep!

Roger | New York

I love iWIN newsletter.  I can’t wait for each issue to arrive on Thursday evening. Tom does a great job.  Tom has been known to send out special sweepstakes notices, when he finds something that can’t wait for the newsletter.  He also offers his own contest/giveaways, they are always so much fun!

Lucy | Michigan

iWINContests helped us win a once in a life time experience that we were able to share with many friends and family.  Thanks iWIN!

Donna | Ohio

As a long time subscriber to IWinContests, I have won many great prizes because of the information shared in the newsletter.The newsletter, which is sent weekly via an email, lists sweepstakes and contests that are your best bet to enter. My most memorable win is a trip to Beijing, China. I...

Krista | Ohio

iWIN gives me the opportunity to try new social media entries that I may not have tried otherwise. Tom often tells you exactly how to enter and the sky is the limit. You can anything from a koozie to a trip to Paris! Tom also shares his wins with us...

Laura | Pennsylvania

I started entering sweepstakes about a year ago. I stick to Tom’s sweepstake principle “the more you sweep, the more chances you could win”, and guess what? I won an amazing grand prize of a Music Fest Sweepstakes a week ago estimated $8100! The following is part of the exciting...

Jack | Kentucky

Here is a picture from my biggest win. An ATV won from a texting contest on iWIN! Thank you for all you do and a great newsletter.

Beth | Washington

Thanks Iwincontests.com and #iwinroscoe for helping me win this mini Jeep ATV from Mike’s Hard Lemonade! #entry

Jen | Ohio

Love your newsletter and text group I’m here because of you at the iHeartRadio 80’s music fest.

Cathy | California

I, along with so many others am a busy person, I don’t have the time that I want to devote to entering sweepstakes. I find that iwincontests.com sends out a very well informed newsletter, that is just my style. I typically spend 2-3 hours per week entering contests, on a Thursday night...

Pam | Pennsylvania

Wonderful experiences with friends are the true prizes in life. My husband and I enjoy the annual Greenwich Wine & Food Festival but with VIP tickets costing $500 each, we traditionally only attend as general admission guests. The posting on iWin to win such tickets allowed us to enjoy it...

Lisa | Connecticut

I am in heaven right now. Just checked my emails and I was already notified that I won the Refrigerator contest. I get a refrigerator worth $1,200. This was the first voting contest I have ever won. I can’t believe I won. In this contest you could not see how...

Martha | Maryland

Thanks for helping me with $1000 from the iWIN Text Group!

Lisa | Oklahoma

Thanks iWINContests!  I just got my $1000.00 from Pepsi/Culvers arctic puzzle adventure sweepstakes.

Natasha | Minnesota

iWIN is always finding the best sweeps. Thanks for helping me win a this awesome TV!

Cam | Washington

I signed up for iWin back in July 2017 at the Annual Sweepstakes Convention in Las Vegas. I had found myself getting bored with the other newsletter I had subscribed to for a few years and thought it might be time for a change. Well in the short time I...

Diane | Ohio

iWIN Contests is a great resource because it gives you access to many sweeps that aren’t listed on other sweepstake websites. if you don’t have a lot of time to enter sweepstakes iWin is great. Some of the best sweeps will be sent straight to your email inbox weekly.

Kenny | Virginia

Some of the prizes I bought with my $500 Lowes GC win!  Thanks iWIN!

Kathy W

After listening to Tom’s talk about winning 10+ trips in a year, most due to skill and perseverance, I was excited to give it a try. Upon my return home from the Las Vegas Convention, I got to work. Since then I’ve won a few small prizes, and a 1st...

Jo H

Thanks again for posting a blogger/incredible Egg Contest. This was only listed on the website. This one required you to recreate the dish the blogger made. The best part about this one….I was the ONLY one who entered! I maybe spent 15 to 20 on ingredients and walked away with...

Ilona B

Please find the Aspen Dental and Danica Patrick photos attached. It was a great trip! Aspen Dental went all out. We had a car and driver for the day, hot passes, an air conditioned travel trailer to use with couches, TVs, food and drink. It was parked just inside of...

Teri S

ACC Championship Thank you so much for adding the Food Lion MVP Sweepstakes to your newsletter! I get to take my husband to the ACC Championship game and stay warm and dry in the Food Lion tent! We are having a blast!

Rebecca T | North Carolina

I found out about IWINContests a few weeks ago from a friend who likes to “sweep” and said Tom helped her win contests, so I joined and would you believe I won the very first time I entered a contest he “picked”. Looking forward to many more wins with iWIN.

Stephanie M

NBA Finals We won a trip to the NBA Finals in Cleveland!  Thanks iWIN!

Jess S | Kansas

Private Jet to Big Game Air  Thanks Tom for the great trip I won via iWinContests. Private jet from Bud Light and Big Game Air to a college football game.  I was able to take 3 friends to see Miami take on Virginia Tech.  What a day….once in a lifetime...

Doug P | New Jersey

Limited Edition Hot Wheels Camaro Thanks to IWinContests.com and the weekly newsletter, I was the grand prize winner of this 2018 limited edition Hot Wheels Camaro with a daily entry. I’ve been entering sweepstakes for 7 years and this is my biggest win yet! Thanks Tom for all you do!

Jan | Michigan

I received my tailgating trailer that I won,  it’s pretty fantastic! Thanks for your help!

Catherine

Thanks Iwincontests.com for posting in the newsletter, had a wonderful day on the Bud Light cruise on Chicago River and Lake Michigan!

Melissa C. | Illinois

If it wasn’t for Tom and iWIN we would have never known (OR WON!) about cute contests like this one. We love iWIN because of the personal advice we get from Tom and the winnable contests he provides. Something for everyone.

Heather S

Frank’s Red Hot Thanks Tom and iWINContests for letting me know about this contest! You make me look forward to Thursdays!

Brian | North Carolina

Super Bowl LIII Thank you again!!!!! Without your site I wouldn’t have won this amazing experience. Me and my husband are extremely excited and grateful.

Samantha

My best friend invited me to a mini sweepstakes convention in Charlotte, N.C. about three years ago. I was impressed by one session about how to enter the sweepstakes smartly and effectively, which was taught by Tom of iWincontest.com. I therefore, signed up to be a member at the conference. 

Jack L | California

If it wasn’t for iWINContests newsletter I would have never known or entered to win a trip to Spring Training in Goodyear Arizona. The trip included airfare, hotel, special meet & greet dinner with former coaches & players. We felt like special guests of the Cleveland Indians and enjoyed several...

Valerie | Florida

Thanks to Tom and iWINContests I won a VIP trip to Miami to see the Heat play. It was a simple RT to win on Twitter. We had a blast! I have had several very nice wins from sweeps in iWINContests!

MaryBeth | Massachussetts

Thanks to iWin I was alerted to a Facebook sweep Travelocity was offering that I had not seen until that day. I entered and was one of 20 winners of a $2,000 Travelocity GC. This win allowed me to surprise my Mom with a “bucket list” trip to Alaska! It...

Kerrie B

Thanks iwincontests.com and Tom for the SwissGear luggage set I won! Now this gal is hoping for a trip win…fingers crossed!

Vicki F

Hey Tom! Just wanted to let you know I won the Sheetz $50000 for July! Just had the ceremony and got my check! Thank you iWin for letting me know about this sweeps!

Annette | North Carolina

I woke up to a message from Reese’s on Twitter! This will come in handy for Christmas. I am so excited! Thank you iwincontests.com

Jenny C | Florida

$95,000 Cash in the Michelob Ultra Superior Year Contest I have been waiting a very long time to be able to share this email with you to give iWinContests.com and Tom my personal thanks! My name is Kristen, and I was the winner of the Michelob Ultra Superior Year contest, which included...

Kristen

Mercedes-Benz AMG GTR “Great news! You’ve been randomly drawn as a winner for the Drive Home in Your Very Own Mercedes-Benz AMG GTR!” OMGosh, this has been a wild experience!!! The ARV for this car is $165,000. Yes that’s right. $165K. I knew I’d win a car some day but...

Mary

View All

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iWIN Interview with Velma Green

Meet Sweeper Velma Green who recently was on the Price is Right and also has won 100K from a baseball team, among many other prizes!

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Have you ever wanted to stay in the Disney Dream Suite?

iWIN Tom interview a member, Donna, who had just that opportunity from a sweepstakes a few years back.

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Who Knows Steve Best?

This was a fun game featured at the 2025 National Sweepstakes Convention in Little Rock, AR. Steve has long been a well-known figure in the sweepstakes world, serving as both a source of motivation and inspiration. Over the years, he has attended countless conventions, hosted several himself, and become beloved by many in the hobby. In this video, you’ll hear stories about some of Steve’s favorite wins and sponsors.

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iWIN Interview Edition – with Leah

Tom interviews various iWIN Members about their sweeping win adventures, including trips, cash and prizes.

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iWIN Interview with Heather – 10K Disney Trip winner!

Heather has won a ton of great prizes, trips, cash and more. Check out her exclusive interview with iWIN Tom!

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iWIN Live – Convention Host Chat

Chat with the 2026 National Sweepstakes Convention Hosts. The Convention will be held in Scottsdale, AZ from July 9th-12th. Video includes a tour of the newly remodeled rooms and facility.

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iWIN Live – 2026 National Sweepstakes Discussion

iWIN Tom interviews the convention hosts, Paula and Karen who will be hosting the 2026 National Sweepstakes Convention in Scottsdale, AZ.

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iWIN Live – Q/A with National Sweepstakes Convention Host

Donna talks with Tom about the upcoming Las Vegas National Sweepstakes Convention which will be held Aug 1-4th.

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iWIN Interview with Jake!

Join iWIN Tom as he interviews Jake about his incredible sweepstakes journey — including winning a Super Bowl trip, an iHeart Music Festival trip, and more amazing experiences along the way. Don’t miss the stories, tips, and behind-the-scenes details from one of iWIN’s big winners!

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iWIN Interview with Karen

Join iWIN Tom as he interviews Karen about her incredible sweepstakes journey — including winning a Dodge Ram Truck, a NASCAR trip with Ally to Kansas City, and much more. Karen also shares her best insights on entering, winning, and staying focused and motivated in the sweepstakes hobby!

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iWIN Interview with Steve – PART 1 of 2

Join iWIN Tom as he sits down with legendary sweeper Steve in Part 1 of this incredible interview series! Steve shares stories from decades in the hobby, including winning hundreds of trips, meeting celebrities and athletes, attending unforgettable events, and scoring amazing prizes along the way. From sports experiences to once-in-a-lifetime moments, Steve talks about what keeps him motivated and why he still loves the sweepstakes hobby today.

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iWIN Interview with Steve – PART 2 of 2

Join iWIN Tom as he interviews legendary sweeper Steve, who has won hundreds of trips, met countless celebrities, and scored amazing prizes over the years! In Part 2, Steve shares more incredible stories from the hobby — including celebrity meet-and-greets, sports experiences, cash wins, memorabilia, and the passion that has kept him motivated for decades. A must-watch interview for anyone who loves sweepstakes, winning, and hearing unbelievable prize stories!

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iWIN Interview: Alexis

In this episode of iWIN Interviews, iWIN Tom chats with Alexis about her favorite sweepstakes wins, memorable trips, and the experiences that have made the hobby so rewarding. A fun conversation full of stories, inspiration, and winning memories!