Are You an Underdog? We want to hear from you!

In this episode of REWORK, host Kimberly Rhodes sits down with 37signals founders Jason Fried and David Heinemeier Hansson to hear about the company’s fondness for underdogs – small businesses that are scrappy, do more with less, and use creativity over big budgets.

If this sounds like you, we’d love to hear from you and just might have you on an episode of REWORK to share your story. Plus, the lucky winner will get one year of Basecamp Pro Unlimited on us! Here’s what you need to know:

How to Enter: To participate, share your underdog story by commenting on the official contest post on LinkedIn or Twitter (X). Your entry should include a single photo of your team in action and a description of your underdog story, with a maximum of 500 words.

To complete your entry, you must either:

• Share your story on your own LinkedIn or Twitter profile using the hashtag #UnderdogChallenge and tag the official @37signals account in your post, or
• Fill out the form on Basecamp’s official “Underdog Challenge” contest page at basecamp.com/underdogchallenge.

See the official contest rules for more details.

Transcript

Kimberly (00:00): Welcome to REWORK ,a podcast by 37signals about the better way to work and run your business. I’m your host, Kimberly Rhodes, and I’m joined by the co-founders of 37signals, Jason Fried and David Heinemeier Hansson. And soon we might be joined by you. We are running a contest to bring an underdog onto the podcast to chat with us. But before I talk about that and how you can sign up, let’s talk about underdogs in general. Jason, I know you’ve written a little bit about this on why 37signals loves an underdog. Tell me about it.

Jason (00:28): Well, the whole idea of underdogs appeals to me because they’re scrappy. Uh, they’re up against the world. Uh, they’re typically up against bigger competitors, which is pretty much like every company’s kind of an underdog for a while. And, uh, and anyone who’s starting something new is really an underdog in many ways, unless you’re doing something brand new, no one’s done before. And, uh, I think we’d just like to champion that. That’s where we came from. That’s who we still are. We’ve been around for a long time, but, you know, if you’re looking at our competitors or the competitive space that we’re in, companies we’re up against in a sense have, you know, hundreds of employees and tens of millions or hundreds of millions of dollars in the bank from VCs and, and we’re self-funded and we’re, you know, relatively small business. So those are our people.

(01:11): We’re those people. And, and we just like to support those who are, um, figuring out how to make it go with with with less. That’s just always also been a common theme for us. Less software, simpler products. And I think on the company side, having a simpler company, a smaller company, a company with less is actually a really big advantage, so we wanna highlight that. Because also I would say people in that position often feel like they don’t have what they need. If they only had more, they could do more. And I don’t think that’s usually the case. The more you have, oftentimes the slower you go and more frustrating things end up being So, um, viva underdogs.

David (01:49): What I really like about the underdog framing is it takes something that’s perhaps more objective. You’re a small company and then it turns that into an advantage because as Jason said, there’s so many small companies who look at being small as a disadvantage. And in fact, we think it’s a huge advantage. When I look at where we are today, the number of employees we have or what we can do, I don’t go, oh, I wish we were a thousand people. Oh, I wish we’d raised a hundred million dollars in VC. And I think our aggressive defense of smaller companies under the umbrella of underdog is actually exactly what’s resonating so well when it comes to things like this podcast, when it comes to the original book REWORK. When we get, uh, people writing us about REWORK the most, uh, enthusiastic readers are usually the ones who could identify themselves in the things we’re talking about.

(02:47): And that means identifying themselves as underdogs. Oftentimes they just don’t even have the word for it. They think of themselves as a small company, and that gives them all this baggage of, oh, I wish I had blah, blah, blah. And here we come out and say like, no, actually this is great. Embrace your constraints. Do more with less. All of these things, you can move so much faster, it’s because you’re an underdog. The other thing I think I love about underdog is there’s a sense of adversarial nature in it and embracing that. Like we were an underdog when we started with four people going up against, again, VC-backed companies. We were also an underdog when we were going up against freaking Apple when they were trying to kick us out of the App Store. And I think there’s just some sense of broad identification here that, um, underdog is a state of mind.

(03:36): And it’s funny, if you look at founder-led companies that do grow large, they try to hold onto that. Um, Amazon is perhaps the ultimate examples of not being an underdog. They’re literally the 800,000 pound gorilla in e-commerce. But Jeff Bezos for, for the longest time, this is day one. Day one, is a way of trying to infuse underdog ethos into even a huge company, it’s just so much harder. When you really actually, literally are an underdog, when you are a small company, it’s so much easier to embrace. You just need to have that little pivot of your, uh, identification, of your framing and then embracing and going like, this is great. So that’s what we’re here to do on this podcast, and in general, to give underdogs this self-confidence that not only is it okay, it’s amazing. It is awesome. You are in the best time of your life, the best time of your entrepreneurial journey, as long as you can keep that underdog ethos to it. Um, I also just think it’s more fun. Again, one of those parallels to a company that’s now 800,000 pound gorilla. Steve Jobs was really fond of talking about the pirates versus the Navy, right? I think that was the pitch to the original CEO he hired who then kicked him out of the company was, do you wanna join the Navy or do you wanna be a pirate? Implying here that you wanna be a pirate, right? Pirate is just another word for underdog.

Kimberly (05:04): And our new marketing campaign is all centered around the underdog. So I’ll link to that new ad in our show notes. And I feel like it’s interesting, even thinking about sports, it’s like everyone loves that comeback story, that underdog story. The person who came from behind now that we’re seeing like Olympic things kind of, um, spin up. It seems like the underdog story is where it’s at.

Jason (05:23): Well, people can identify with it because everyone’s been there. Most people are still there. Uh, and and every new thing you’re there. If you wanna learn guitar like you’re the underdog already, like, you know all the things you have to do. You’re a new parent, you’re like, I don’t know how to do this. Like, what?You know. So this, this is a recurring theme in people’s lives. Um, people can identify with it and you wanna pull for people who are in that position. 'cause you know how hard it is. And, um, uh, I, I think, you know, business is the obvious place for us since we’re a business to pull for that. Um, but you know, originally we were talking about, uh, just kind of doing campaigns, sort of being for the small business. This is sort of how this whole underdog thing happened because we’ve we’re, we are a small business.

(06:03): We’ve always been for the small business. We, we we’re for the Fortune 5 million as we like to say. But it still felt like it wasn’t quite landing on what it, what we’re really about, which is, um, the scrappiness. Like you can be a small fully-formed business that’s well served in a small area and you’re not really an underdog. You’re just kind of actually the, the leader in a space or, but to actually be at, uh, at what feels like a disadvantage, which of course, like David said, is an advantage, but what feels like a disadvantage when you’re small, uh, that’s where you really, I think that’s kind of, that’s the area where I think you can actually do the most with the energy that you have and sort of, uh, fight angry in a sense. Uh, to some degree. I, we know we don’t like to talk about words of war and business. 'cause business is not war. But there is this sense of a fight and, and you’re, you’re battling against something or someone. That’s just a fun place to be in anything, you know? And, um, uh, that’s what we felt like was really what really embodied the spirit we were going after.

David (07:06): Another way of framing this as we’ve done in the past is what do we do here? What do we make, we make tools to arm the rebels. And that is again, another phrasing of we make tools for underdogs. So when we think of, um, who are we making Basecamp for? Who are we making HEY for? We’re not envisioning, um, what, uh, features do we need to add? So to we can land that huge enterprise account where it needs to go through whatever, six months of a sales cycle and all this other stuff. No, we’re speaking directly to the underdogs. Someone who is, um, looking for a tool for again, smaller company going up against something, trying to get some advantage, right? Like how do we give these underdogs an advantage so that when they do go up against the big enterprise competitor, they’re moving faster, they’re moving smarter, they’re doing more.

(07:57): Um, that really fires me up. There’s sort of a, an allegiance, a band of brothers kind of vibe going on when you both identify as an underdog and you’re also, this is who we’re serving. 'Cause you could also think like, hey, I’m an underdog. I just supply whatever things to huge companies. And that’s how I do. That’s great. Awesome. Good for you. We identify as underdogs serving other underdogs. And I think that’s really kind of, when Jason picked that term, I was like, yes, that clicks. That’s, that’s it. That sort of just falls into place. And I think with marketing, a lot of it is to try to figure that out. Who exactly are we selling to? What identifies that group and what connects us to that group? Why are we a better vendor for underdogs than someone else? Well 'cause we’re in the same shoes as you are. Because we’re trying to do the same things because we’re up against the same things, because we’ve seen the same things because we’re dealing with the same constraints.

(08:53): And all of these matters of it, trying to fuse that connection, not just for a customer to be able to identify us and go like, hey, I wanna buy from 37signals. I wanna buy Basecamp because this is tools made for underdogs by underdogs, but also for us to motivate us in the work that we do. That, why do we keep on pushing this? Why are we still going strong 20 years in trying to, to build these tools? It’s because it’s more than just making a nice piece of software and selling it to whoever. It’s because we have a connection to who we’re selling to and we want to genuinely help them. This is so much of what this podcast and everything we publish and everything we do is about, right? How can we help the underdogs get the advantage? Um, or even not even just advantage some bearings in this world. Figure out where to go next. Feel, get some self-confidence. So much of what we talk about is things that a lot of underdogs say no, but they’re afraid of, am I doing it right? Um, no one else seems to believe this. Well, here we are proudly and sometimes brashly affirming the magic that’s already in your fingers.

Kimberly (10:02): Well, we are celebrating the underdog. We are one of you and we are gonna bring someone on the podcast to tell us their underdog story. So if you’re scrappy doing more with less, we’d love to hear from you. To enter the contest, look for our announcement on the 37signals LinkedIn and comment with a picture of your team and your underdog story. We’ll be selecting one person to join us for a special episode of REWORK, and you’ll also receive a one year free subscription of Basecamp Pro Unlimited on us. You can check out all the details at basecamp.com/underdogchallenge. The deadline to enter is September 15th.