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8 Emails that Changed the Author’s Life

I’ve explained many times that I’m an introvert. I get my energy from and can accomplish a lot when I spend time alone. Many of you have self-identified as introverts also.

This is not a deficiency! Actually, it’s something to be quite proud of. There are many benefits to being an introvert, one being that we’re incredibly self-reliant.

However, being an introvert doesn’t excuse you from participating in society. It’s still important to meet people and build connections. It’s important to push yourself to get to know people who inspire you, make friends with them, and spend time with them.

But how do you make these connections when going out to networking events and parties is just not your style?

Everyone bashes email these days as an old and out-of-date medium, but as an introvert who can sometimes be painfully shy, I’ve found it to be an incredibly useful tool for starting and building relationships I would not have been able to build another way.

Last month, I wrote about how one simple email I drafted back in college lead to a coffee date with a Fortune 500 CEO. In that article, I went on to explain some of the best practices for making connections via email with people you admire and respect, and then challenged you to send a few emails of your own to get the ball rolling on your own relationship-building campaign.

Funny enough, this challenge lead to a paid position on the Riskology.co team (our very first team member!) for one reader who chose to send me an email. I’ll share her story in the future—it’s a fun one.

Stories of the World’s Best Emails

While I was putting together the story of my coffee date with a CEO, it dawned on me I actually have lots of friends with similar stories. I’m hardly the only one who’s ever sent an email to someone they admired and found something valuable from the exchange.

So, I decided to—you guessed it—send an email to some of my friends asking for their stories. I can’t believe what I got back.

I collected nearly 20 great stories. Some of them made me laugh. Others made me think. Some were so awkward they made me cringe a bit. But in the end, each writer accomplished what they set out to do: expand life by taking a risk and emailing someone they wanted to get to know better.

It’s my pleasure to share a few of the best ones.

How Two Strangers Achieved World Domination

Over the last few years, I’ve had the pleasure of making two close friends and partners in Chris Guillebeau and J.D. Roth.

Even though they both live right here in Portland, my relationship with both started via email. Back in 2008, I wrote J.D. because I was a big fan of his site, Get Rich Slowly, and invited him out to dinner. He said yes, and being the gentleman he is, even paid for the meal despite my protests!

The next year, I sent a simple email to Chris thanking him for the manifesto he’d just published called 279 Days to Overnight Success. It really changed how I looked at starting big projects.

Long story short, that simple email spiraled (over the course of several years) into some really great partnerships.

But I’m not just friends with Chris and J.D. separately. Chris and J.D. are also good friends themselves, and we all work together on The World Domination Summit.

Funny enough, Chris and J.D.’s friendship also started with an email between strangers. I asked Chris to share his story of getting to know J.D., and here’s what he said:

chris-guillebeauYears ago, I wanted to be a writer, and I decided the best way to begin was through blogging. I had the idea to create a community of like-minded people oriented around unconventional ideas. In the early days, I paid close attention to what other people had done to cultivate community and grow their own careers. J.D. Roth was #1 on this list. I loved what he had done with Get Rich Slowly, and I was glad he responded when I reached out by email.

J.D. answered all my questions without hesitation, even personal questions about things like money and stress. As I continued to grow my blog and began publishing books, I asked myself many times along the way: “What would J.D. do?” (I’m still working on the line of bracelets.)

Five years later, J.D. and I have spent a lot of time together. We rode an Amtrak train together from Chicago to Portland. Then he came to Norway with me for my final country, a weekend we called the End of the World. We’ve produced three annual events for thousands of people.

I’m glad I sent that initial email.

To realize that one little email helped get the ball rolling for the empire Chris has built today is pretty exciting. Of course, that email was followed by years of hard work and dedication, but obviously Chris is pretty grateful to have met J.D.

Now, the best part of this story is that J.D. feels the same way. Building connections is not about trying to get something from someone. It’s about collaborating and finding ways to give of yourself in a way that benefits both sides of the relationship.

I told J.D. about my email project and asked him if he had anything to contribute. I’m pretty excited about what he came back with:

jd-rothI don’t have a good example of how sending an email changed my life, but I do have several examples of how answering them had an impact on my world.

I used to ignore emails from people wanting to buy my blog, for instance. After a couple of years of this, I made a change. I started responding to folks who said they were interested in buying me out. The first guy was crazy. But the second guy? The second guy had the weight of a publicly-traded corporation behind him, a corporation that gave me an offer that made my jaw drop. So, yeah, responding to that email was a good idea.

I could name several other examples like that, but perhaps my favorite story is this. In 2008, I received an email from a blog reader. He was going to be in Portland the following week, and he wanted to know if I’d have lunch with him. “Sure,” I said. “Let’s do it.” I met this reader and his wife at a local Thai place. We had a great conversation. I was impressed with his story and his drive. Over the next year, this reader published a guest post or two at Get Rich Slowly. He stayed at my house one night when he got stranded in Portland. We talked about blogging and about marketing and about travel.

Eventually this guy —whose name is Chris Guillebeau—moved to Portland. Over time, our friendship grew. I joined Chris for a train ride from Chicago to Portland. On that trip, he shared a crazy idea. “I want to create a conference and hold it in Portland. I want you to be on the planning team,” he told me. So, for the past three years I’ve helped to organize and stage WDS, which has grown into a grand party for 3000 people. Over that time, Chris and I have continued to support each other. Who knows what he future holds? And all of it because he sent a simple email and I answered it.

This is a rare look into both sides of how a massively successful friendship developed from a plain ol’ email. I’m grateful to have these two guys in my life and be able to share this story with you.

Writing for a Major Newspaper and Becoming Friends with the Biggest Name in Your Industry

For the last two years, I’ve been in a “mastermind” with two guys named James Clear and Scott Dinsmore. Once a month, we call each other up, share any big wins or setbacks we had, and help each other brainstorm strategies for moving forward in our businesses.

In more than three years of working for myself full-time, I can say I’ve gotten many things wrong. Forming a mastermind with these guys is one thing I got right.

And the three of us initially got to know each other how? Yep, via email. Both Scott and James emailed me in 2010 after the initial success of Riskology.co. James was just starting a blog and Scott was trying to breathe life into a project that had limped along for a while.

Since starting our mastermind, I’ve watched them both go on to grow their businesses to a size many multiples of my own. A humbling experience! But I couldn’t be happier to surround myself with two of the smartest people I’ve ever met.

Naturally, they’re a perfect fit for this email project. I asked James for a story, and he came back with the time an email lead to becoming a guest author for The US News and World Report:

james-clearI wanted to write for US News & World Report.

I found out that the editor had a book that had launched a few months before, so I emailed her to ask if there was a way that I could help promote the book. This was three months after I had starting writing online, so I had no audience and essentially no way of making sales, but she appreciated the offer.

Three months later — after I had landed a position writing for American Express — I sent the US News Editor another email and asked if I could write for them. Here’s what I said…



It’s been a while since we’ve talked, so I figured I would break the silence! 🙂 [Tyler: It’s a lot easier and more successful to open with something like this once you’ve already established a connection and proven yourself useful like James did.]

Things have been going great on my site — growth is up, products are on the market, and life is good. That said, I’m always on the lookout for new collaboration opportunities. I just started writing for American Express on their OPEN Forum site and that got me thinking that it might be fun to write for US News as well.

I’m not sure how this process works, but I figured you would be a great person to ask. I wasn’t thinking too much of a long-term gig (unless it’s paid or something of the sort), but I would love to do a guest post or two for US News. How would that process work?




The shocker? She replied, “It is nice to hear from you and I’m so glad things are going so well. We would welcome a guest post or two from you.”

A few weeks later, my first article was live on US News. I went on to write more than a dozen articles for them and grow my audience by thousands because of it.

The big lesson here is easily to ask. If you never ask, the answer is always no.

The second lesson, which is just as important, is to help people as often as you can. Even if you have nothing to provide like I did in the beginning, reach out and offer. Nobody was ever offended by someone offering to help them. Get the conversation started however you can.

I asked Scott to share a story, as well, and he came back with one about becoming friends with one of the world’s most successful bloggers (name removed as a courtesy):

scott-dinsmoreI think that for me, getting to know _______ would be a good example.

He hosted a blogging dinner in San Francisco. I was brand new to the space and was very nervous about the event but really wanted to meet him. I’d just recently discovered the world of blogging and felt a bit out of place. But I figured I’d show up anyway and see what happened. Since I couldn’t offer anything of value related to web business or writing, I decided I’d share a list of vegetarian/vegan spots in SF that my wife and I loved – as a way of thanking him for what he’d taught me. I know he was a vegan and thought it’d be something I’d appreciate if I were new to town. I also offered to take him on a fun trail run in SF as I knew he was a bit of a runner. We only got to chat for a few minutes at the event. But we got out on a run a few days later and then started to make it a routine thing. A couple years later, he’s become a very close friend in SF.

When trying to contact someone you feel is out of your league (or anyone for that matter), I believe the key is to think of how you can offer unique value to them and show that you really care about helping. That will usually be on a topic related to your expertise, not theirs, but that’s very relevant to their life. Just try to be helpful and make their world a little better. That leads to some pretty interesting connections.

Now, do you see why I’m so lucky to know these guys? They’re fearless (or at least seem so) when it comes to making connections with people who inspire them. They’re confident in themselves, and they know what they have to offer.

James and Scott both reinforced an important point about making connections—especially via email: the most important thing you can do is find something valuable to offer. Building connections is not about getting something from a stranger; it’s about finding something to give and being happy to do it.

The 15-Year-Old with a Video Game Contract

Here’s another fun story from my friend, Danny Iny, one of the smartest business minds I’ve ever met. Danny actually used the telephone to make his connection, but the medium is far less important than the lesson behind it: having confidence in yourself and what you have to offer others is one of the biggest factors in getting what you want.

Danny, at 15 years old with no previous programming experience, called up the CEO of a video game company and got himself hired to write a game. Unbelievable, right? Here’s the story in Danny’s words:

danny-inySo this story starts when I was 15 years old; I had just dropped out of school to start my first business, which I figured would be about building websites, because I knew some HTML. (Yeah, these days I’d know better…) 😉

Except that it didn’t go very well, because I didn’t know anything about web design, or about business, so pretty soon I was looking for another opportunity. Well, one day, I was hanging out with a friend, and his seven-year-old-sister was in the room, playing some education game. My friend pointed at the screen and said “I’ll bet you could build something like that.”

I replied, “You’re right, I bet I could.”

(No idea why, though—I didn’t know anything about programming, or game design, or anything.)

So I found the box that the game came in, called up the company, and said that I wanted to meet with the person in charge to discuss a possible joint venture, and I got a meeting with the CEO.

It didn’t even occur to me at the time that this was a big deal, and I don’t for the life of me remember what I said, but it couldn’t have been anything special. I just asked for the meeting, and I got it.

So the meeting time comes around, and I walk into this guy’s office—15 years old, not knowing anything—but still completely confident for some reason—and I proposed a joint venture. I told him that I could build games that he could sell. I explained to him that I’d “conferred with a psychologist” (my mom has a degree in psychology), and reached the conclusion that the best way for kids to learn is if they’re having fun, and the learning happens in the background, rather than just doing math exercises on the screen.

Now, what he could have said was “No kidding, I’ve been doing this for 10 years, now get out of my office,” but instead he opened a drawer, pulled out a document, blew a cloud of dust off of it, and put it on the table. He explained that this was a script for a game that he had written many years ago, so how about if I built it, and they’ll sell it?

I said sure, I’d be happy to.

So we started talking specifics, and he asked me how I was going to build it.

I had no idea, but I had a friend who knew Visual Basic, and I figured that maybe he could teach me, so I told him, “I’ll build it in Visual Basic.”

He said, “Isn’t that like reinventing the wheel? Why not build it in Director?”

I put my hand on the desk, and said, “Look, if we’re going to work together, then of course I’ll have to adapt my business practices, so no problem, I’ll build it in Director.” [Tyler: This is why I like email! You don’t have to think on your feet like this!]

We shook hands, I went home, and opened up Google, which was brand new at the time, and typed in “What is Director?”

I ended up working on a number of game projects with this company, and I’m incredibly grateful that they gave me this early opportunity. The really crazy thing is that none of that would have happened if I hadn’t made that call that, honestly, I might not have had any business making.

So the takeaway here is that you should make the call anyway. Hearing someone say “no” will sting for a few minutes or hours, but on the off-chance that they say “yes,” it can change the course of your career.

You Don’t Have to Get Anything to Find Success

I want to finish this piece with two more fun examples. By now, I hope you’re thoroughly convinced that big things can come from very small actions when they’re done with care and intention.

My friend, Chase, is one of the most funny and charismatic guys you could ever hope to meet. I asked him to share a story, and boy did he deliver:

chase-reevesMine wasn’t actually an email; it was a tweet.

I’m a big fan of a guy called Merlin Mann, whose writing and thoughts about doing good work have meant a lot to me over the years.

He had this book he was writing with a really great subtitle: “cut the bullshit, do the hard stuff, start making things you love.”

I loved that sentiment so much that I wanted it as a desktop for my computer. So I made it.

And, once I made it, I wanted Merlin to see it. I mean, this is the internet age, right? So I sent him a tweet…. and waited. Nada. No response. No dice.

But I didn’t give up there (Did I mention how much I really like Merlin?). So, I was also following his wife on twitter (it’s getting kinda creepy, isn’t it? my bad). So I sent it to her… maybe there’s a back door into Merlin’s heart. [Tyler: Sometimes, the spouse is the gatekeeper for a busy person.]

Shortly after my tweet to her, he saw it. This was amazing to me. He retweeted it! Wow, that’s a good sign, right? Not the best part, though.

The best part — this part is the BEST — he commented on the post and told me what he thought… and it was good.

This was a big deal for me. At the time I didn’t really see myself as a designer… I was more of a marketer guy. But this, this was something I designed and that one of my heroes really dug (Read his comment! And then my super lame response). It was probably the beginning of me taking my design skills a little more seriously.

So, thanks Merlin. First time creepy follow-tweeter, long time fan.

See? It’s not even about the medium. I like emails, but when you approach someone with authenticity, it doesn’t really matter how you do it. In this case, it all started with a tweet.

Finally, I asked my Internet pal, Caleb Wojcik—friend and business partner of Chase from above—the same question: “Can you tell me about a time when you sent an email to someone “out of your league” and it changed your life for the better?”

Here’s what he shared:

caleb-wojcikHaving gone through business school and hearing “it’s not what you know, it’s who you know” hundreds of times, when I started blogging I wanted to give the whole networking thing an honest try. So before I went to Chris Guillebeau’s first book tour stop near me, I specifically bought a domain name for two reasons. First, I could tell it to him when he signed my book, and second, I’d have something non-cubicle-related to talk about with people I sat next to. [Tyler: That’s smart!]

After the event I emailed him this:

“Thanks for coming to Seattle to speak last night. It was great to hear your message and to see so many other non-conformists there. I met some interesting people and I look forward to any other time you come up to Seattle for a meet-up if just to meet more cool people. I much enjoyed your book and will pass it on to others to read it and be challenged. You are an inspiration to all of us who have dreams.”

He replied, “Hey thanks, Caleb From Seattle. It was a lot of fun last night… so glad you were a part of it. All the best and I’ll look forward to seeing you again sometime. – cg”

It was then I realized how Chris grew such a large following online. One on one connections, specifically in person during book tours and conferences, and simply just caring about people.

He has continued to be a major inspiration and help to me in more ways that he could ever know. He is how I first heard of Corbett Barr and Think Traffic which I now work for, he was one of my first podcast interviews, I’ve met some of my closest friends at his conference, and more.

So, thank you Chris, for being the final push I needed to start my blog and for the continued support over the past few years.

I wanted to close with Caleb’s story because there’s an important lesson in it:

Caleb didn’t ask for or need anything from Chris to get something from sending the email he did. It was just a gratitude email. Caleb was grateful for the work Chris did, so he took a second and put in the effort to let him know.

Caleb went on to get even more from Chris’s work in the future, never needing anything specific from him.

 The Intersection of Success and Effort

So much of success in life comes from just putting in a little more effort than the average person. And that’s the beauty of the 5-Email Challenge. Simply doing it adds value to your life regardless of whether you receive a response.

It demonstrates that getting what you really want from life is more about putting in a little effort and proving to yourself that you can step outside your comfort zone than it is even about making connections.

The connections you do make, of course, never hurt. But even if you get zero replies (you won’t), you still get something incredibly valuable out of the process.

Finally: A Little Tongue Lashing from Seth Godin

When you decide to take a risk, the results are not always what you expect or hope for. What can I say? That’s life!

As I was making my rounds, asking for stories to share with you, I decided to step out of my comfort zone a bit and ask Seth Godin, one of my favorite authors of all time, to share a personal story. Here’s his reply:

seth-godinI hope you have the guts to include this:

I think this is a lousy, lousy idea. Sending an email you have no business sending takes zero guts. It’s spam, plain and simple. People who send unsolicited stuff over the transom and pretend they are being brave are merely being selfish.

Putting yourself on the line requires more than chutzpah.

If you care, you’ll be generous first, brave second and truly respectful of people’s time third.

Wow; sobering. I thought I’d done a pretty good job of explaining how much I respected Seth and enjoyed sharing his work, and was pretty surprised to get a response like that.

When I saw it, the only thing I could think was: “Oh my God, Seth Godin hates me and all of my ideas. I’m going to cry.” I think I sat and sulked the rest of the day.

But after letting it sink in, I realized Seth actually contributed something incredibly useful: he reminded me—yet again—that building a great relationship is not about figuring out what you can get from someone (especially someone you don’t even know). To be a truly Smart Riskologist means putting yourself on the line by offering yourself without asking anything in return. Great relationships are built by giving, not by trying to game any system to see what you can get.

(Sidenote: Seth, if you ever read this, I promised I’d include this. I hope I did justice to your intention.)

As you go about your life trying to make connections with the people you admire, never forget that. Give fully. Give honestly.

Yours in risk-taking,
Founder, Riskology.co

P.S. If you read this and thought, “Umm, where are all the examples from women?,” I thought the same thing! I asked a number of my female colleagues to contribute, but none of them came through by press time. The show must go on!