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I paid out big time this year

Ramit Sethi

Everyone deserves to live a Rich Life.

To have the freedom, flexibility, and financial resources they need to do work they love, buy what they want, and have unforgettable experiences — not just once in a lifetime, but as often as they want.

Over the past 11 years I’ve taught millions of readers in countries all over the world how to create their own Rich Life. Some have landed their Dream Jobs. Some have negotiated big jumps in their salaries. And some have turned their ideas into successful online businesses.

And some — like our 5 recent contest winners below — have been lucky enough to get a taste of what it means to live a Rich Life by winning one of our extravagant “Rich Life giveaways”.

#1 – “Ultimate 20-for-30 Entrepreneur Jumpstartgiveaway – Chris H.

This may be the best giveaway we’ve ever done.

I gave a student twenty fully-paid-for, 30-minute coaching sessions with a hand-selected group of world-class entrepreneurs, authors and business strategists — so he could jump-start his online business with hands-on help from the best of the best.

A conservative estimate on this is that if you had to pay to work with all of these people out of your own pocket, which you can’t do by the way, it would run you upwards of $30,000.

I can’t even imagine what access like this would have meant to me when I was first starting out. At the very least it would have saved me many years, many mistakes and a crazy amount of money. I love being in the position to give this gift to our winner, Chris. And I can’t wait to hear about all of the breakthroughs he makes on the calls. (If you want to find out what Chris is learning, he’s going to be documenting his experience here.)

Congrats, Chris!

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#2 – “Instant Vacation” giveaway – Jessica Boyd

A lot of our readers dream of starting their own online business so they can get paid well and work from anywhere in the world. That’s why last summer I decided to give away an “Instant Vacation” worth a total of $7600 to show one lucky reader what owning an online business could be like.

The purse:

  • A $2,500 flight voucher
  • $1,000 cash
  • Macbook Pro ($2,500)
  • iPhone 6 ($850)
  • Bose QuietComfort 20i Noise-cancelling headphones ($300)
  • Minaal carry-on bag ($300)
  • Kindle ($100)
  • Field Notes notebook ($50)
  • Total value: $7,600

Here’s what the winner, Jessica Boyd, had to say about winning:

“I’ve used the vouchers to book my first trip to New Orleans at the end of October and Turks & Caicos in December! I think I’ll be able to squeeze a third trip in there as well if I get lucky. 🙂 Very, very excited!

I can’t explain enough how perfectly timed each of these prizes were — especially the new Mac. As a freelance graphic designer and marketing consultant, it’s saving my life! (My old 2009 Mac was on the super duper fritz from undergrad, law school, and business school. There’s no telling how long it was going to hold out!) The BOSE headphones are making my workouts full out concerts! One of the best things to happen all year!”

And here she is getting excited in real time.

Yes, living a Rich Life is all it’s cracked up to be.

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#3 – “Best Pitch” contest – Jacqueline du Plessis

Earlier this year I put out a challenge to IWT readers: pitch me on a solution to make my life/business easier. I showed people the difference between good pitches and bad pitches and then waited while the entries flooded in.

And this pitch was the clear winner.

Jacqueline offered to show me the time of my life in Cape Town, South Africa. And she went above and beyond what everyone else did. If you want to see what you need to do to get a busy person’s attention (something I talk about in depth in this post), study her pitch with a fine tooth comb.

“Winning the IWT contest allowed me to keep building a Rich Life, by giving me some “fun money” to play with and experiment with in building a team for my online business.”

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#4 – “Cruise for 10” giveaway – Sarah Steele

I used to daydream about winning the lottery and inviting my friends to join me on an unforgettable month-long vacation.

I don’t have to dream about it anymore.

Left: Me in SE Asia with a large, smelly animal. | Right: Loved flying my parents in to NYC for the holidays

These days I’m able to take extraordinary trips with friends while I continue to earn money. I can pay for my parents to travel wherever they want (to see me of course). And I recently got to send 10 people I don’t even know on a cruise.

Sarah was just about to have her 3rd child when she won, so plans are still in the works, but her family is ready to book their tickets.

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#5 – “$10,000 for My 10 Year Anniversary” – Michelle Schroeder

In hindsight, I’m not sure why I used this picture for this contest

IWT turned 10 last year and I thought what better way to celebrate and thank my readers than to give someone a chance to create their own Rich Life.

Up until that point I’d given away trips, rent payments, gym memberships, and even a lifetime subscription to Netflix. This time I wanted to let the winner choose how they’d spend $10,000.

Michelle Schroeder, a personal finance blogger, was the lucky winner. She used the money to travel around North America in style.

To your Rich Life,


P.S. We’ve added a ton of new videos on how to build an online business and live a Rich Life to our Zero to Launch channel. Check them out here.

Live Your Rich Life Now

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