New Book Profiles My Award Booking Service and Shows You How to Become Independent as Well

Link: The $100 Startup on Amazon for $15.64 and eligible for free Amazon Prime 2-day shipping.

Chris Guillebreau is one of the people I admire most. Oh, sure, there are Nobel Peace Prize winners (not all of them), successful major corporate CEOs, and celebrities (very few of them). But Chris has managed to find a niche for himself that I truly admire. He has figured out what he has good at, taking his understanding of specific things, breaking it down, and communicating it clearly enough that non-experts will pay him for the translation he provides. He evangelizes his ability to do this, and helps others to do it to, and those folks will pay him for the expertise. He gives away much of his content free, builds his personal brand, and that serves as the real marketing behind his efforts.

There are some folks in the frequent flyer community who don’t much like him, one of his services is his “Travel Hacking Cartel” where he explains how to get large amounts of miles quickly and inexpensively, and then how to use those miles to travel the world for free or inexpensively. The critique is generally that the information is available for free for those who look, but to me that misses the point. The value Chris creates is in the translation, the explanation, and in reaching people with it who wouldn’t even know where to begin or know what they were looking for in the first place. And he does give away much of his knowledge for free. That said, I really don’t like the term “travel hacking” to describe what it is that we do, and that I write about on my own blog.

But I look up to Chris and try to emulate him because he’s given himself real financial and lifestyle freedom by doing the most genuine thing any person can do, offering themselves up to the world as a service. And he’s a shining, ‘everyman’ example of being able to do that at a low cost and reach large numbers of people.

When Dan Pink wrote Free Agent Nation I thought he was onto something but was overselling the idea, in reality I think he was just early. We aren’t all free agents or consultants just yet, but the world is changing to allow many of us to be if we want and many of us probably will be in the future.

One of the best pieces of advice I ever received — that I did not take and act on — was from a former partner of Sir John Templeton (the mutual fund king). He suggested saving and investing 50% of every raise. Since you never had the money before, you don’t feel any loss. You still reward yourself along the way spending half of every increase you get. But each step along the way is a major milestone for saving, and saving early (through compounding returns) is the best way to become financially independent. I didn’t do it, nobody does, but I’m still working hard on the idea.

I used to ‘just’ have a full-time job. Sure, I had this blog too, but it didn’t make any money, there weren’t even any banner ads on the site until late 2004 or early 2005. When Randy Petersen put up ‘BlogAds’ here they were sold at, I think, $40 a week. I told Randy to keep it, to cover hosting costs, noting at the time that it wouldn’t be enough for either of us to pay for the weddings we were planning. It wasn’t until probably four years ago, eight years into blogging, that I even saw a dime from it. Advertising on the blog isn’t something I figure will be around forever, I may run out of interesting things to say. I’ve always written for myself, what I find interesting, and hope that others do as well. But it’s created a personal brand, and it’s taken something I love and become a (modest) income stream.

Two and a half years ago I also started consulting on frequent flyer award bookings. I knew the ins and outs of the programs, I was answering emails all the time, but I never imagined anyone would pay for something that they could figure out for free on their own, right? And paying for it meant cutting into the savings to, undermining the value proposition of the ‘free’ award. Just as I hated fuel surcharges, I was skeptical of consulting fees. But I’ve had the opportunity to help many hundreds of people redeeming hundreds of millions of miles. It’s grown beyond my wildest dreams and through my award booking service I’ve even taken on a partner — one of the few people I’d ever trust who could do award tickets with the same skill and alacrity that I bring to the table. (I do by the way consider Lucky at PointsPros and Matthew of Live and Let’s Fly to be excellent as well.)

It’s this story that Chris includes in a very small way in his new book, The $100 Startup. He takes 50 case studies of small entrepreneurs who got started without upfront cash, talks to them about what they learned along the way, and the mistakes they made. I suspect that thousands of people will see themselves in at least a couple of the stories, and be inspired and then motivated to try it on their own as well. Because as a side project, and without startup cash, there’s nothing to lose. Which is what finally got me into the game, and I hope will help me make up for not taking the advice to save half my raises.

Even though I haven’t ‘broken free’ from 9 to 5 work, I’m still much more independent because having multiple income streams means I don’t worry as much what happens next, and as long as I keep my ‘real job’ and have these other things on the side I can build the cushion that someone much more temperamentally conservative like me wants.

The book has great lessons on figuring out what you have to offer, on marketing it, testing and tweaking to improve performance, and even franchising. A friend of mine recently commented that he didn’t want to build a business that would make some money when he worked hard, he wanted to build something that would keep generating returns while he sat on the beach. That’s the dream, right?

First time I’ve seen something like this, though I imagine other books have done similar things before, it actually has a video trailer which is really cool.

It looks like Chris’ book tour will be in the DC area at the end of the week so I hope to make it out and offer my congratulations in person.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. “Oh, sure, there are Nobel Peace Prize winners (not all of them), successful major corporate CEOs, and celebrities (very few of them).”
    One step forward (and two steps back). The more you try to show us your enlightened perspective (the more you betray your biases).

  2. @Dax I genuinely have no idea what you’re talking about. I would certainly qualify “successful major corporate CEOs” as well, by the way, I probably do not admire even a particularly high percentage of those if that’s what you mean?

  3. If you had asked me 12 years ago if this was likely or even possible, I’d have said no. But 11 years ago I taught myself basic HTML and made a 6-page website. Start-up cost: almost zero (a few bucks for the URL and hosting). It now has hundreds of pages and gets nearly a million visitors a month. I make an excellent living from it. I’ve also started other sites with almost no start-up cost.

    The thing that frustrates me is, I’ve tried to get close friends and family, some of whom could really use the money and/or a change of career, to follow in my footsteps. I know they could do what I’ve done. But they won’t. They prefer collecting a salary. You have to have a tolerance of risk and a willingness to work your butt off to succeed as an entrepreneur.

  4. Wonderful post Gary. It came from down deep and I appreciate all you have done and the road you have traveled. I told you at the FTU that my son and his family also live in DC. He is a professor at GW. Years ago, when he told me he thought he wanted to go into academia, he was concerned that money would be an issue. I told him that I knew doctors and lawyers and money is ALWAYS an issue, but that nowadays, both partner work and they figure it out. Serendipitously, I found a book called, “Do What You Love And The Money Will Follow”. Yes, you may never leave the full-time job and I can only hope you enjoy it, but you have developed such a fine reputation and you help so many people. I really appreciate your post and I hope you continue to go from strength to strength!

    Steve

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