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Three Days of Learning & Community: Last Weekend at Pioneer Nation

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Last weekend I worked with a small and dedicated team to produce our second-ever Pioneer Nation, a gathering of independent entrepreneurs.

For the first time in any big event we’ve done, we took everyone onsite for the entire experience. The event was held at The Resort at the Mountain, a scenic setting near Mount Hood, an hour’s drive from Portland.

Events are a ton of work, but they can also be hugely rewarding. Once again I felt honored and inspired to be surrounded by great people.

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Pioneer Nation Returns in October: Here’s How You Can Join Us!

Last year we debuted an all-new event to serve independent entrepreneurs and anyone who felt underserved by existing business conferences. We called it Pioneer Nation—and the first gathering was a tremendous success.

We'll be returning in October (just two months from now!) for our second edition. If you'd like to hang out in a mountain resort an hour from Portland, Oregon and learn new skills for taking your business to another level, you can join us.

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One Log Cabin and 800 Yoga Mats: Some Unconventional Tax Deductions from My Life in 2014


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My tax return is complicated for a lot of reasons. First, I run several different businesses which all have their own set of accounting. WDS, our annual gathering, has its own legal structure, including a foundation that is completely separate from all my other projects. Last year we started an all-new event that also has its own legal structure.

So yeah, it’s complicated. It takes about 20 hours just to prepare all the info for my accountant, and as with most tax-prep tasks, it’s not usually a fun process. But I do enjoy seeing some of the charges on my statements from the previous year. They remind me of the crazy life I have, and the many fun experiences that I'm fortunate to participate in.

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How to Book Airfare on Short Notice

It’s a common myth, yet at first glance it doesn’t make sense: booking plane tickets on short notice should be cheap. If there are empty seats, why wouldn’t the airline discount them as the flight approaches? But as you may have discovered if you’ve ever tried to jet off on a whim somewhere, you’re inclined…

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Something New! If You Work for Yourself, Join Us On the Oregon Trail

Greetings, friends and readers!.

As discussed recently, lots of big things are in the works. I'll be heading out for my Annual Review trip soon ... we're building out the business ... next year I'll have a new book and a new tour ... but first things first..

Next March, we're hosting an all-new event focused on independent work. It's not something that everyone will care for, but we know it will help a lot of folks..

Read on if you'd like, or help us out by sending it to someone who might be interested ...

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