I’m giving away two round-trip tickets anywhere in the USA

If you’re wondering, yes, I’m giving away 2 round-trip tickets anywhere in the USA. The link is right here. But as some background... Because I’m a huge weirdo, I have a 19-page document where my assistant stores every preference I have. For example, with travel, here’s a direct excerpt from the doc: FREQUENT FLYER #s: (Ramit ...

I’m giving away $1,001

When I was in high school, I got a consulting gig doing phone sales for a web hosting company. I remember the first time I got paid and realized I could actually live an awesome lifestyle. Of course, like most high-school students, I was stupid. I earned thousands of dollars, spent it all (I don’t even remember on what), ...

Win “Dinner for Two” for a year

Two months ago, I ran a giveaway for two plane tickets anywhere in the US. Robyn won! She’s planning to fly to her coin-collecting grandfather to Philadelphia to see how coins are made. Last month, I gave away $1,001 on Amazon. Meghan won! She’s using her prize to buy the "most luxurious, highest quality bedding she can ...

Win a $1,001 shopping spree

When I was in college, I had a scholarship that let me buy any books I wanted. I would walk into the bookstore, see literally any book I wanted, and buy it. There was a credit with the store so I wouldn’t even take out my credit card. So I had books about psychology, decision-making, cons, deception, seduction, risk, ...

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Announcing the “Rich Life Giveaway”

Last year, I hosted a bunch of giveaways as an experiment: I was trying to find out if they worked to get more attention for IWT and to change IWT readers’ behavior. As usual, some of it worked, some of it didn’t. Can you guess which one was the most/least popular contest of last year? $1,001 cash ...

The best hotel I ever stayed at

I always told my friends that when I made it, I was bringing all of them with me. So after I launched Dream Job in January 2012, and I took a 3-week vacation to SE Asia (Vietnam, Cambodia, and Thailand), I had a new theme for my vacation: “My villa is your villa.” I told my friends to fly into ...

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