The REWORK podcast

A podcast about a better way to work and run your business. We bring you stories and unconventional wisdom from Basecamp’s co-founders and other business owners.


The Email That Changed My Life

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Basecamp probably wouldn’t exist today if not for an email that David Heinemeier Hansson sent Jason Fried in 2001. That correspondence was the beginning of a partnership that produced Basecamp, several books, and most recently HEY, the company’s new email service. This episode is our love letter to email. Hear from David and Jason, as well as other artists, writers, and founders about the emails that changed their lives.

The Full Transcript:

[00:00:00] Broken By Design by Clip Art plays.

Shaun: [00:00:02] Welcome to Rework, a podcast by Basecamp about the better way to work and run your business. I’m Shaun Hildner.

Wailin: [00:00:07] And I’m Wailin Wong. We’ve spent the last seven weeks talking about HEY, Basecamp’s new email service. We’ve gone behind the scenes of how the product was conceived, designed, branded, and launched. Now we’ve come to the end of this arc and we have one last episode for you, our love letter to email.

Shaun: [00:00:24] Over the last few months we’ve collected stories about life-changing emails. Emails that changed the course of someone’s career, marked a personal milestone, or captured a significant moment in time.

Wailin: [00:00:34] I think a lot of us have emails like this in our archives. For me, seven years ago when I was working at a different job, I got an email from Basecamp’s CEO Jason Fried with the subject line, “Tell me more about what you want to write.” I wouldn’t be here doing this podcast today if it hadn’t been for that email and what followed.

Shaun: [00:00:54] That’s awesome. I once got an email from a Nigerian prince and now I’m a billionaire.

Wailin: [00:00:59] Uh, congrats.

Shaun: [00:01:01] Thank you. Basecamp, the company, also wouldn’t exist today without email. We’re going to start things off with co-founders Jason Fried and David Heinemeier Hansson who met when David sent an email to Jason. At the time, the company was a web design firm called 37 Signals. Also, we should note, that neither of these guys saved that damn, life-changing email.

David: [00:01:26] I was sitting in Copenhagen, Denmark, seven time zones away from Chicago. I was just a fan of the company. I think, was it ’99 that the manifest went up with the 37 ideas about how to do web design differently. A web design company that did not have any design, as I considered design at the time, graphics, on their website. It was just a bunch of text links that put out philosophy and positions on where they saw themselves and they saw the industry, and I thought it was deeply fascinating. So I started following Signal v. Noise, which was a blog that was also founded in ’99. And it was on that blog that Jason posted the request for, hey, is there anyone there that can help me?

Jason: [00:02:06] Back in, was it 2001?

David: [00:02:08] Yep.

Jason: [00:02:09] I was learning how to program in PHP and I was basically following a book, so I wasn’t really learning. I was copying from a book. I was trying to build this book organizing software, which I’d built in FileMaker Pro years and years before but I wanted to make a software as a service version, a web-based version, which was really early, in 2001. And so I started learning how to code in PHP and I kind of got far enough. I got as far as the examples would let me get in the book and then I had another idea, like, well, how do I do this? I think it was pagination was kind of something I stumbled over. And I couldn’t figure out how to get it right.

[00:02:44] And so, I posted something on our blog about it. Can anyone out there help me? Because I don’t know anyone else who knows this stuff. And David responded via email and was really thoughtful and helpful.

David: [00:02:53] I was just like, hey, I’ve gotten two years out of reading this blog. It’s been very inspiring to me in a bunch of ways, and influential. I can give something back to that.

Jason: [00:03:03] Sometimes if you think of the prototypical IT person, it’s very condescending. Well, this is how you do it, how could you not have known that? That kind of thing. It was not that way at all. It was very thoughtful and helpful. We went back and forth a few times, and eventually, I’m like. You know what? I should just hire you to finish this thing for me because I’ve botched it already. And after he saw my code, he was like, yeah, you should really hire me to do this because you botched it.

David: [00:03:25] I think for about six months, we just worked over email and perhaps a little bit of IM, which at the time, maybe was AOL Messenger?

Jason: [00:03:34] AOL Instant Messenger, yeah.

David: [00:03:37] Anyway, we used these tools and predominantly we used emails for a lot of it, for six months, before I even talked to Jason on the phone. Clearly our entire amazing journey that we’ve been on ever since was born out of an email. So it’s it fitting that here we are 20 years later, launching an email product.

[00:03:53] Email is kind of like one way of sending considered thought and we absolutely still share a lot of considered thought, where someone will… one of us will write something up, multiple paragraphs, just for that other person to consider asynchronously on their own time. I mean, we also do a bunch of other stuff, but that core, which is really for me, the appeal of email, is that you’re not thinking a line at a time, as you do in chat. You’re really sitting down and you’re thinking your argument through. Usually we do this when it’s sort of a bigger argument or something, when we think, like, okay, here’s a debate coming. Let’s seed the debate and let’s set the premise for what we’re talking about so we write it up long form and that might as well go in an email. It may go into Basecamp, as most of our internal communication does. But just that idea that writing long form is a great way to communicate and email is one way of distributing those thoughts. Yeah, very key.

Saya: [00:04:53] My name is Saya Hillman and I have been running a company, Mac & Cheese Productions based out of Chicago since 2004. The very first event that I started throwing are called Minglers, and they were born out of me being dissatisfied with “getting out there.” I think we’ve always been told, “You have to get out there to meet people.” Whether that’s for professional reasons and networking, or personal reasons and whether you’re trying to date, or just speak with friends. I love this idea of meeting a bunch of new people in a group setting who are all there for the same reason of wanting to meet other people from day one of the Minglers, I’ve always hosted them out of my live-workspace. They usually range from 15-30 people on a Friday or Saturday night for a few hours. And the cherry on top is you made a new friend. You met someone you want to date. You got a client. You know, you’re going to collaborate with someone. So those are the Minglers, and my longest running event.

[00:05:58] So, November-ish, 2009, I had just sent out a note to my email list that I had just added a December 2009 Mingler, and if anybody was interested, here’s how to sign up. I don’t know what was going on in December 2009, but this was actually one of my largest Minglers. It was so big that I don’t allow this number anymore, just because it can get a little unwieldy, but there were actually more than 40 people at this particular Mingler. I got a deluge of sign-ups and one of them happened to be from this guy, Pete, who I had never met before.

[00:06:31] Towards the end of the evening, he was one of the few stragglers, probably about one in the morning, and he came up to me and mentioned that when he first moved to the city he and a friend had gone around to all of the barbecue restaurants in Chicago. When I heard this, I was like, oh my gosh, who is this person? Then he left along with all the other guests and he sent me a very nice, short, sweet, grammatically correct, good spelling, thank you email, the next day. I feel like a lot of guys in my world are not the types of people who are going to send thank yous after something like that. So that stuck out to me.

[00:07:13] So this is December 20th, 2009. “Hi Saya! I definitely want to say thanks again for a great evening. I had a wonderful time, and once more, I get a second type of pleasure just knowing that there are folks like you out there valuing people and human connection as you do and working to make events like this happen. The world is a better place because you’re in it. Happy holidays, and I hope to see you soon. Take care, Pete.”

[00:07:35] And I responded to him, “Thanks Pete, that’s very kind of you to say. Great to meet you, let’s grab barbecue some time.” And then a few weeks later, so this is January 2010, I think, I read a review about a new barbecue restaurant that had just opened and I just sent him the link and said, “This looks cool, should check it out.”

[00:07:57] That then started a 27 email thread that was titled barbecue. That’s when we actually made plans to go and actually get said barbecue. Again, I’m thinking at this point, this is just a fun nice new friend to hang out with. Because when I meet someone, girl or guy, whoever, that seems fun and interesting, I always say this. We should hang out. You seem awesome.

[00:08:21] We got married in 2013. I love that I still have all these emails from back then and it was a wonderful trip down memory lane to read all of those and to see, like, oh, is this where I started falling in love with him? When did he start falling in love with me? And all of… and yeah, it was really fun.

[00:08:38] So email, besides email being wonderful for just communication purposes, it’s also, it’s a really cool diary or journal of relationships with people.

Rick: [00:08:49] My name is Rick Cosgrove. I am the executive creative director at Agency EA here in Chicago, a brand experience agency. This was around April 2018. We had just executed a pretty massive RFP response for Samsung. That project was for something called the Samsung Developer’s Conference. It’s bringing about 3,000+ developers all to the same place. We flew out to California to do the pitch in person. The team from HQ flew in from Korea. I would say over half of our room was native Korean speaking. Some spoke better English than others, but ultimately everybody was really interested in what we had to present, and was very friendly and open. They did tell us that we would be finding out within, I think it was a week or something like that. So I got a text and it had to be, like, I think it was 4:45 or 5:15 in the morning, and it was from Lauren, our business development team, and she’s like, guys, I don’t know if you saw the email. I’m trying to translate. The subject line was: “A Decision Has Been Made” and then you open the email and it’s all in Korean. It’s Samsung. It’s Samsung! Did we get it? She’s frantically trying to take this screenshot and put it into a Google Translate image system on her phone and trying to figure out what it says. And ultimately, she’s like, okay, it says we need to log into the portal. And we’re like, okay, get in the portal, Lauren!

[00:10:28] We’re all in a group chat at like 5 in the morning. Okay, Lauren, get in the portal! She’s like, oh shoot, guys, I left my username and password at the office. So we’re now all just like sitting in frantic anticipation before the sun rises and Lauren’s getting over to the office as fast as possible. And finally she gets to the office, she logs in and it lets us know that we won the job. We told them the whole story, and they were cracking up. They definitely forgot about the time difference, because part of it might have even been automated where once they put the decision into the system, the system is going to send out an automated email to all parties who participated in the bid at the same time. And in that case they’re running on their normal business hours in Korea, not thinking about globally what time that information’s getting to us.

[00:11:24] It was smooth from that part on and we became pros at our 7pm central / 9am KST time calls that we had with them biweekly. Ultimately, we’ve really grown some really great friendships with that group of people.

Julie: [00:11:40] My name’s Julie Wernau and I’m a reporter. So I had just had a few months out from ending a 15-year relationship. Like anyone who goes through that kind of breakup, I was trying to figure out who I was. This was like a big part of my identity. Found myself sort of trying on a lot of things and a lot of people. But wasn’t really feeling like I had any direction or goal in my life and it started to feel like what if I just live this way forever?

[00:12:20] And so I started thinking about people in my life who I felt had these lives that they just managed to live with such direction and purpose. And instead of doing what I usually do, which is think, well, I’m just not like that, aren’t they lucky that they’re like that. I thought, what if they could tell me how they do that?

[00:12:41] And so, I sat down and I just started writing. And the subject of the email, I remember, was “You inspire me.” One of these people was my childhood best friend. We’d known each other since we were little kids. Another one was my own brother. Some of them didn’t know each other and if they had met would probably not really like each other. These are people who have strong personalities, strong opinions. I really laid it out on the table. I said, I’m in this place in my life where I’m having fun and I’m finding my way, but I really feel like my life lacks any meaning or purpose or direction and I don’t really want to waste any more time. Please tell me the things that have inspired you. I think I wrote it all in one go and walked away, and then said, do I really want to send this? And are these the right people to send it to? And should I put them in the BCC line, or should they all know who each other are?

[00:13:42] And then finally, I just sent it. No BCC. I went to sleep and then hoped that when I woke up in the morning, there might be some emails in my inbox. Which, as you can imagine, when you write to a group of very motivated individuals, they’re all morning people, of course. So I did.

[00:14:08] It was just incredible, the response I got. I mean, it really was life-changing. First of all, the responses made me realize that at a certain core level, there wasn’t something so different about all of these people that I didn’t have inside of me. And so, each of them wrote me these stories telling me about times in their lives that they were stuck within maybe their field, or stuck in their relationships, or they were trying to figure out whether they wanted to be a mother or what it means to not be a mother. One of the most inspiring things was to find that there, even though a lot of these people were writing me individually, there were themes. The thing that really changed my life was across the board, people had something they called either commandments or principles or guideposts that they had created for themselves. From then on, any time they needed to make a major decision in their life, they went back to that set of commandments or guide posts and consulted with it.

[00:15:14] And what was kind of neat to me about that was they weren’t consulting with some TED talk. They were consulting with themselves. And so after I read through all of these responses, I sat down and I did exactly that. I created a list of guiding principles for my life and I still have that document and I still go into that document when I need to make a major decision in my life. And what’s really amazing is that generally speaking, those goals and values and guiding principles remain the same for me, even years later.

[00:15:57] There’s something really comforting in having something so stable about yourself that you go back to. Even when things become unstable again. And then, as it turned out, very shortly after that, I would use those guiding principles to make a decision to leave Chicago, move to New York, take this big job, and the rest of my life sort of has set out from that point.

Mike: [00:16:26] My name is Mike McGee. I am the director of special projects at It was Spring of 2011, my friend, Neal Sáles-Griffin and I wanted to learn how to build web applications and build tech startups and there was no in-person accelerated program for beginners. And so we were coming up with this coding bootcamp idea. We were also considering joining President Obama’s re-election campaign. The President Obama re-election opportunity was obviously amazing, incredible. Neal and I were in Grant Park in 2008 when President Obama won the election. Where Neal and I were living was just a few blocks away from the Obama family residence so we, during May of that year, had to decide between, do we go forward with this idea to build a beginner-focused tech school, coding bootcamp, or do we join the President’s re-election campaign in downtown Chicago. And we’re like, we’ve got to pick one.

[00:17:43] So that was the backdrop, and all throughout May, we were going back and forth with venture capitalists and the software development industry here in Chicago. By mid-May, we were like, okay, we’re going to go fully into this coding bootcamp. We’re focusing on a problem that we want to solve. We have money to be able to build it the right way. That’s enough for us to be crazy to turn down this offer.

[00:18:12] So the particular email was on May 18th, 2011. We both got offers from the Director of Human Resources for the campaign. I believe her name was Sheena Patton. The signature page was a standard one. There’s two lines, put your signature if you approve. Put your signature if you decline. Neal sent his in with no issues. I sent mine in a little after his, that afternoon. And Sheena emailed me back saying, hey, your signature is a little bit off of the line. It wasn’t… it was a previewed PDF document, so I don’t know if the way my signature was on there as if I made a mistake. Like I put my signature on the decline side, but I meant to put it on the approve. Which is of course, yeah, is a very natural thing. Like, why would someone decline the opportunity to work for the President, it’s pretty stupid. So then I had to go back and say, nope, I meant decline. Thank you for the opportunity, yes. I am declining this offer. And so, resend the email. She sends it back, like, all right, understood. Good luck. And then I follow up with like, thanks, dot dot dot… I’ll need it.

[00:19:32] That particular email, of just really officially declining the opportunity to work for the President, when, again, three years before we were in Grant Park to witness history, because we were crazy enough to think that we could build this tech school. Neal and I being crazy enough to believe that we could turn down the President… not him directly. If he would have called, we probably would have a different story here. I don’t think I would have been able to turn down Barack Obama. So it was a pretty wild time that I don’t want to relive, in person. But it’s fun to talk about on a podcast where I can cherry pick memories.

Nate: [00:20:12] My name is Nate Otto and I’m a Chicago-based artist and muralist. I left my full-time job in 2012, shortly after getting married. And at this point I’ve done a good 50 murals. Everything I get comes in randomly, for the most part. I don’t do any real direct marketing. I usually don’t get productive results when I reach out to companies or individuals directly because art directors like to make their own decisions. They like to be the one that discovers somebody, I found. I cast a wide net and whoever happens to come in, comes in.

[00:20:46] And usually, that’s in the form of email. I call them magic emails. Sometimes I get several in a week, sometimes several months will go by without getting any, but I’ve gotten random emails from companies big and small. It could be just a company that never crossed my mind before. Like, last year, for example, I got an email from Goose Island one day that led to a whole bunch of stuff that I did throughout the year. The subject line was: “Artist collaboration.” This was last year, 2019. They wanted me to be the first person that decorated a hundred tap handles that all went together, but then they also got distributed to different bars. It’s for a beer called Born + Raised.

[00:21:29] And then, ultimately, they wound up using the image of all 100 of those tap handles together and they put that on a CTA train as an advertisement, which they put my name really big, which was great. And then later on in the year, they hired me for a mural at one of their restaurants. So that just came about because I got an email one day.

[00:21:51] I know that things fall apart all the time. Last year, I probably got contacted by 15 or 20 jobs that didn’t wind up happening. Whether just the job didn’t happen or my quote missed the mark, or something. A number of things can happen to make an opportunity not actually happen. So I’ve learned from experience to basically not count my eggs and not tell anybody or name a company until I’ve actually been paid by them.

[00:22:20] My favorite is when they say how much they’re going to pay me in the first email. There have been a couple times where I’ve just jumped up. Like, I opened the email, and was just like yes. So I jumped up like a… Warby Parker sent a magic email a couple years ago. So when you get one of those emails from an art director, from a big company and they say I’m going to pay you X amount to do this, it’s pretty much right there. That’s the whole thing. And that can be a big chunk of my income for the year.

[00:22:47] If you know my name, Nate Otto, you can probably find my email. You can probably find my Instagram, you can find my website. And that’s all you need to go on. And that’s basically how my business works. Just random emails. Magic emails from random places.

[00:23:00] I’m extremely fortunate in that I basically just get to live my dream every day by making art. Liz: [00:23:08] I’m Liz Fosslien. I’m the co-author and illustrator of a book called No Hard Feelings: The Secret Power of Embracing Emotions at Work.

[00:23:18] I had just kind of taken the plunge from more traditional career path into tech and started working at this startup. Really loved it, had a great friend group. And then, as all startups do, it kind of changed over the next few years. And I then, at the end, was just like, completely emotionally burnt out. And then I decided to leave that job. And I had no idea what I wanted to do next. Should I go to business school? Should I just… what should I do with the wide world in front of me? I definitely felt a lot of pressure to still be like, this was part of the plan, this is great, it’s just one more step in my journey. When in fact what I was feeling was like, oh my God, what am I going to do. I’m not employed. I’ve no idea where to go after this. What are my skills? Who am I?

[00:24:02] And so, I’d met someone at the startup who left maybe a year before I did. She was always very open about her emotions and just pushing people to find a path that’s meaningful for them. So this is what I wrote her. “I feel really lost. I know it was the right decision to leave, and I’m doing everything positive. I’m running. I’m cooking healthy food. I’m taking time to figure out what’s next, meeting with friends, asking them about their careers, and I still have no idea what I want to do next. I just simply want to be done with this period of my life where there’s so much uncertainty. Have you ever had this happen? How long until it stopped? I thought I would ask. It would be simply nice to know it gets better, you’ll figure something out.”

[00:24:46] And then she sent me the most amazing, inspirational email I’ve ever received that I still look back on when I’m just feeling kind of burnt out. She’d written a lot about how, growing up, we’re taught that there’s sort of a career path and a ladder, and that success is sitting at a desk at an office at 11 AM and feeling like you’re part of this company in a tall building on a tall floor, wearing a suit. That doesn’t have to be what you do. If you’re a creative, if at 11 AM, you’re just wandering around trying to think of ideas, or let’s say that you worked really hard in the morning and you need to take a few days off, or a few hours off in the middle of the day. All of that is okay, and different people’s work flows, different people’s versions of success, careers, all of that. It’s much more flexible than we’re taught. You should always just think like, what do I find meaningful, how do I want to spend my day. And then if you can achieve that, then that is success no matter what it looks like.

[00:25:44] And she wrote, “The worst thing we do is bravely step out of the mold but then stupidly use someone else’s rubric to judge our lives every day. If you’re going to forge your own path, then do so without judgment. It is a beautiful thing to want something for yourself that originates from you.”

[00:26:01] These are the two sentences that I actually have saved on my computer to reference again. Now I work in a creative field, I’m at a startup again. Everything’s great, but everyone has bad days and so these are the sentences that I look at. And she talked how she had gone through similar periods in her life and just from the outside I just thought she was so successful and so great at her job. And so to see that someone else that, again, externally, who seemed so put together and great at what she did had gone through similar periods.

[00:26:29] It just allowed me to feel more like, okay, I have savings. I’m in this privileged position of being able to actually take a month of not doing something if I don’t want to do anything, and that that’s also a totally fine part of life. That it doesn’t always have to be like, working working, get the next thing, keep going, pushing, pushing, have a side project, have this, have that. I think instilled in me the power of responding to someone and comforting them, even if you’re not close. And how meaningful it can be just to reply to the email that someone sent you. Obviously taking, kind of a limb, and being vulnerable. I think this was the only email I sent out during that time where I was pretty open about how down I was feeling, and to get such a vulnerable response back. I’ve always sort of remembered that act of kindness.

[00:27:16] Broken By Design by Clip Art plays.

Shaun: [00:27:21] Rework is produced by Wailin Wong and me, Shaun Hildner. Music for the show is by Clip Art.

Wailin: [00:27:26] I will put contact information and social media handles for the folks in this episode in our show notes, which you can find at We are going on hiatus for the rest of August and playing some reruns while we get ready to come back in September.

Shaun: [00:27:40] So stay safe, stay healthy and we’ll see you in a month.

[00:27:45] Broken By Design by Clip Art plays.