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New experiment: I’ll pay your rent or mortgage for a month

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I’ll make this quick.

For one of you, I’ll send you a check for your next month’s rent or mortgage payment — free.

No catches, no tricks. One of you will get a check for up to $2,001, free, directly from me.

Here’s why:

June month is BIG WINS Month at IWT.

Instead of so-called “expert” advice about how you should create your own detergent and de-activate the lightbulb in your oven to save energy (1.21 gigawats??), I’ve spent the last 8 years of this site focusing you on the Big Wins in life: negotiation, earning more, spending extravagantly on the things you love (while cutting mercilessly on the things you don’t), and finding your Dream Job.

So rather than guiltily struggling to save $3 on your daily coffee, then descending into a limitless pit of anguish and despair when your limited willpower cannot overcome your caffeine addiction, you can do a few things really well…and not worry about the rest.

For most of us, our rent/mortgage is our biggest single expenditure. Think about it: What would your biggest win be? How would optimizing that change your life?

Would it be negotiating $10,000 salary increase, like many of my readers have? Or earning $2,000/month on the side? Or automating your finances so you spend less than 1 hour/month on money?

When you think about this, it becomes clear that saving $2 and $3 here and there becomes largely irrelevant to living a rich life.

I’ve got a lot of great material on Big Wins coming your way this month. But first, I want to kick things off by giving one of you a Big Win…directly from me.

I’ll pick a winner on Mon Jun 18 and you’ll receive a check by the first week of July.

For one of you, let me pay your rent/mortgage. Here’s the link to sign up (free):


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  1. My wife is a teacher and is going back to school to get her Masters degree. This would be a big help!

  2. Thanks for the chance to win, Everyone needs help with rent/mortgage. This extra money will be a good 1 year anniversary gift for me and my wife.

  3. My big win? When I’m in the position to build my own home, and am able to support my mother thus allowing her to retire – that would be my big win. How to get there? Well, working on it!

  4. My biggest win would be getting a new job, which I’m already in the process of doing. I’ve found a job that I’m more than qualified for that would be paying a lot more than I’m making now.

    I’m taking in a lot of Ramit’s advice, as well as other advice from lifehacker and such. Tweaking my resume to the position to include keywords from the job listing. Researching the company to learn about their culture and jargon. Also putting together a portfolio for the first time in my life if I get the interview.

    Also checking out a few other job listings I’m interested in.

  5. Nathanael Ligon Link to this comment

    I posted this to my facebook and told my friends to click it to have a shot at winning $2,001 in about ten seconds of basically no work. I mentioned that their email address wouldn’t be spammed or sold, and I also asked them to hit ‘like’ if they went through with it – my guess is the vast majority of them will not click. This amazes me.

  6. My biggest win would be finding a job for which I qualify after 20 years out of the job market..not easy for someone in their late 50s in this job market. (Dream big, right?) Thanks for the chance of winning a month of mortgage money in the meantime.

  7. A BIG win for me would be to pay my mortgage off before I retire. Or in other words, retire worry free and that before I’m too old to appreciate it.

  8. Biggest win would be to completely pay off all of my credit cards and my student loans.

  9. Biggest win for me would be to start contributing more to my retirement fund. I’m contributing the bare minimum right now, and I really need to get on the ball. Thanks for the giveaway!

  10. dj pomegranate Link to this comment

    I want to pay off every last cent of my student loans as soon as possible. That would definitely be my biggest win.