Unconventional Investment Strategies: One Man’s $100,000 Gamble (and the Gigantic Return)

by Nate St. Pierre on July 12, 2012

I was at a conference this weekend where something incredible happened – something I’ve never seen before. In fact, I doubt it’s ever been done before.

For the whole story, read on. If you’re in a hurry, you can jump right to the main point.

I wasn’t supposed to attend Chris Guillebeau’s second annual World Domination Summit in Portland last week. Normally, this wouldn’t bother me, because I don’t like conferences anyway. In the past three years that I’ve been doing my “Change the World” projects, I’ve probably gone to about a dozen conferences, but I can tell you that apart from SXSW last year, I’ve never gone to a conference unless I had agreed to be a speaker. That’s how much I dislike them.

But it’s a different story with WDS. (Oh, and if you don’t know who Chris G. is, he’s just this guy who travels, writes, gives back, and connects with people. You can find him at www.chrisguillebeau.com.)

Chris surrounds himself with a “small army of remarkable people,” as he calls it, and I’ve always been impressed with the caliber of people associated with him. Over the years that I’ve grown in my own work, Chris has gone from role model, to peer, to friend.

And I guess along the way I’ve found myself included as a part of his small army as well. Many of my close friends and respected peers were going to WDS last year, and I had a feeling it was going to be really good, so I seriously considered going. Unfortunately, some big life changes prevented me from getting out there, so I watched from afar and noted that it was pretty much what everyone thought it would be: awesome. My numbers may be off here, but I think he sold out all 500 slots in an hour, with 800 people on the waiting list.

I told myself that I would try to get out there this year instead, but when the time came, I had just gone through a really tough few months, and I simply couldn’t afford the ticket. This time I think he sold out all 1,000 slots in 20 minutes, with 1,500 people on the waiting list. That was seven months ago, and I resigned myself to not attending yet again.

And then just six weeks ago Chris came through Milwaukee on his $100 Startup book tour. I went out and braved the crowd to go see and support him (a tough thing for me to do, but I’m glad I did), and after it was over I waited around for the line to die down so I could go up and say hi after all was said and done. We chatted for a few minutes, and he asked me what I’ve been up to since I wrapped up my Love Drop project in February.

I told him the few things I was doing for work and income at the moment, and he seemed a bit disappointed. He said, “But where’s Nate? Where’s the big idea? Where’s the project I want to be part of?” I told him that I did in fact have something on my mind, but I hadn’t been sure about dedicating the time to build it yet – it wasn’t philanthropy based, but more of a fun thing. He said he’d like to see it, and I told him I’d think about building it.

Then he asked me if I was coming to WDS the next month. I told him sorry, no, I’d wanted to this year but just couldn’t afford it, and besides, it’s been sold out forever. He responded “What, is that all? Get on a plane and get out to Portland – don’t worry about the money or the space, I’ll take care of it. It’s my conference, and I want you out there hanging out with us.”

I gratefully accepted his offer, and what’s more, I told him I would have my latest project live by the time I arrived. So I spent the next four weeks building Mixup (the web), and showed up in Portland with a brand-new project to get people involved in.

The conference itself was incredible – inspiring and engaging speakers, people who have done and are doing big things in their areas of expertise. But best of all was the chance to connect with 1,000 people like me . . . people who are all changing the world in their own way. Every one of the attendees had a story, and every one was interesting.

I got to chat with Scott Harrison, the founder of charity: water. I ran into my friend Willo, who always makes me talk to people, and then amazing things happen. I stepped out of my comfort zone to say hello to a stranger while standing in line, and she turned out to be one of the most interesting people I met. Not only that, but I was able to connect her to my friend Kat, and pay forward a bit of all the blessing she’s been to me.

When you’re at a conference populated with a small army of remarkable people, every interaction has the potential to be something big. It’s a great place to be.

For a detailed summary of the experience, check out this article from Sarah Peck (who I’ve known online for years, but finally got the chance to meet in real life). For more real-time chatter about the conference, and to see everyone writing about their experiences, search for #WDS on Twitter (or just click here).

But as good as 99% of the conference was, it paled in comparison to what happened in the last 10 minutes, just before we were dismissed.

The last keynote speaker had just ended, and Chris took the stage for the final farewell. He’s a very low-key, soft-spoken guy, never very excitable, and even on stage, just speaks in a conversational tone (which is how I do it as well, and probably a big reason I like him so much).

He said he wanted to end the conference with two more stories. The first one was an old story, concerning a master who left town to travel, and entrusted three of his servants with different sums of money. Upon his return, the story illustrates the return on the master’s investments from each of the servants.

Chris said he’s always had questions about that man: Why did he leave the money with the servants? Was he hoping to make more back? Did he just want to see what they would do with it? Was he investing in them? Did he trust them?

The second story, he said, is a new one. It’s the story of the 1,000 remarkable people gathered here today, and what we’re going to do as we go back out into the world. He told us that in the past year since the first conference, he’d been approached by many sponsors wanting to be a part of WDS, but he had politely declined them all, because he wanted to focus on all of our stories, and not the paid-for ones. He wanted to keep running the conference as a not-for-profit.

He did, however, get an interesting email from one of the attendees of the first conference, who said they wanted to support WDS financially. Chris politely declined sponsorship, as usual, but the person said that they didn’t want to sponsor, they just wanted to help WDS continue to make an impact.

Then Chris looked out over all of us seated in the theater and said, “I started thinking about everyone coming here this weekend, and realized that this person’s offer amounted to around $100 for everyone here. So here’s what’s going to happen. I’m going to dismiss you in a moment, and as you leave, you’re going to receive an envelope with two things in it: a $100 bill, and a note. It’s very simple. The note says:

Thanks for making #WDS2012 a fantastic experience. We’d love to see how you can put these funds to good use. Start a project, surprise someone, or do something entirely different – it’s up to you.

Please consider this envelope our investment in you. Now go out and do something remarkable with it . . . and change the world. Thank you all for coming.”

(Photo credit: Sarah Peck)

Simple, understated, elegant, and powerful. $100,000 is a lot of money to invest anywhere, much less in a group of people, most of whom you don’t even know. It’s a huge risk if it’s not framed correctly. But Chris did frame it correctly at WDS. The themes for the entire weekend were personal growth, connection to the people of this world, investment in ourselves and others, and the concept of valuable work. We had been absorbing inspirational stories about people going out into the world and doing exactly that with their lives, but stories themselves are of little value unless we all act on what we’ve learned.

And Chris gave us no excuse not to act.

The real power of what he did last weekend wasn’t in the giving away of a large sum of money; it was in the power of an idea – the idea that we are all connected and all responsible and, more importantly, all capable of doing incredible things to change this world for the better.

This week, 1,000 remarkable people are thinking very deliberately about what actions they are going to take to make this happen. Hundreds of articles have already been written on the topic. Hundreds of thousands of people have already seen what happened at a little theater in Portland on Sunday. The ripples from that one simple act are going to expand throughout the next year to touch the hearts, minds and lives of millions of people. And that is worth so much more than $100,000.

I didn’t take an envelope, because my ticket to the conference was already a generous extra gift from Chris. But I’m going to use $100 of my own money, and I already know what I’m going to do with it, and how I’m going to touch a life, in fitting with the themes I was immersed in during WDS.

I’m honored to call Chris a friend, I’m proud to be a part of his small army, and I’m blessed to be able to do what I do.


Due to popular demand, Chris just released video of the last 15 minutes of the conference, where he talks about the investment. Enjoy!

(Image source: Chris Guillebeau)

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