Shane Snow, Co-Founder, Contently
Shane Snow’s Hero’s Journey
How Contently co-founder Shane Snow built a content empire, only to dive back into freelance writing.
Small-town Idaho isn’t exactly a hotbed of entrepreneurship.
That didn’t hold back Shane Snow.
As “one of the few really nerdy people” to grow up in his tiny Idaho town, Snow first forayed into the world of internet startups as a teenager. Those early experiences laid the foundation for a lifelong fascination with entrepreneurship—one that led to the 2010 founding of content marketing behemoth Contently.
Not only is Contently the only unified content marketing platform for the world’s biggest enterprise brands, but it’s also a tremendous source of income for creative freelancers. By Snow’s best estimates, Contently has paid out more than $46 million (and counting) to freelancers around the globe.
Providing work to freelancers is a cause near and dear to Snow’s heart, as he began his own career as a freelance journalist. Now, even as Contently continues to grow, Snow has made the unusual decision to return to his roots as a writer.
He’s taken a step back from the company he’s devoted the last eight years of his life to. Now founder-at-large of Contently, Snow has set his sights again on writing. He’s the author of Smartcuts: The Breakthrough Power of Lateral Thinking, co-author of The Storytelling Edge, and author of the new book Dream Teams: Working Together Without Falling Apart.
“This job that I’m doing now…it’s some sort of weird cross between freelancing and unemployment,” Snow says. “That cycle of going from on my own to this huge journey with hundreds of employees and all these users to back to being on my own. … I’m kind of back to where I started, but having learned a lot. It’s almost like a hero’s journey of some sort.”
Here’s how Shane Snow made it up and over the entrepreneurial hump to rediscover himself on the other side.
A Tale of Two Passions
From a young age, Snow has pursued two primary passions: journalism and entrepreneurship.
As a teenager in a small town, Snow put together a greeting card site in the early days of the internet. He made enough money in high school that his parents took notice—but not in a good way. They made him shut down the website over concerns about legality, and because they wanted Snow to learn the value of hard work instead of getting rich quick.
So Snow took a job at the local gas company, and his parents’ plans quickly backfired. A short stint of digging trenches, spray painting gas meters, and “doing this awful manual labor” merely strengthened Snow’s interest in entrepreneurship.
“I kind of vowed to myself that I would never do that again, and I would never let anybody else tell me what to do for my job again,” Snow says.
So he paid his way through college, studying journalism, by returning to the world of ecommerce. After graduating, he started writing about tech startups for the likes of Wired and Fast Company.
That experience reinvigorated Snow’s entrepreneurial drive. “I’m learning all this great stuff from all of these companies that are changing the world; maybe this journalism thing is teaching me stuff that could actually help me do better at my next startup,” he says.
At the same time, Snow noticed many of us his friends from journalism school were struggling as freelancers—not because they weren’t talented writers, but because they didn’t know how to build websites for their portfolios, handle their taxes, and all the other little details that Snow was accustomed to on account of his experience with ecommerce.
“I realized there was this whole group of people who were way better writers than me, way better journalists, who were doing way worse than me because they didn’t know how to do that entrepreneurship hustle thing that I’d been doing with all my little startups,” Snow says.
That realization inspired the beginnings of Contently. It occurred to Snow that if he could build a platform that would make it easier for journalists to market their craft and manage their careers, then he could collect those people and broker work for them much like a talent agency.
In those early days, it was important to Snow that Contently only work with clients who would pay freelancers well. He quickly discovered those organizations were less likely to be struggling newspapers and more likely to be major enterprise brands such as Pepsi or American Express.
Snow and his co-founders leaned into that realization. They started building tools to help brands manage and do more with content, and soon they found themselves on the cutting edge of content marketing software.
“Suddenly, I found myself with a couple of partners at the head of this company that was dealing with every major brand in America and 100,000 hungry journalists and photographers and videographers around the world who’d built portfolios and were asking for work,” Snow says. “So it’s sort of a crazy thing that happened. … It was a rabbit hole that took us a very different place than I imagined.”
Reflecting on Team Building
After seven years at the helm of Contently, Snow realized his job no longer involved the tasks he loved the most, or was best equipped to handle. “As we grew, we got to a point where I realized that I was not the right person to take our organization to the next level,” he says. “And I was kind of getting a little tired.”
So in 2017, he hired a Chief Marketing Officer and gave her the reins of his department while he went on a two-month sabbatical. He returned in an advisory role for the rest of the year, then stepped aside into the role of founder-at-large in early 2018.
As founder-at-large, Snow checks in with his team every week or two, handles some press activity, speaks at conferences, and so on. “But I’m mostly kind of a figurehead at this point and much more capable people are running it,” he says. “My job now is writing.”
It’s a full-circle moment for Snow, who seems content to be reunited with his “first career love.” Most recently, he’s devoted his writing to Dream Teams, his soon-to-be-published book about teamwork. In the process, he’s gained a chance to reflect on his own team-building experiences at the helm of Contently.
“There’s a few things that I started noticing when my job became more about team building and team management,” he says. “And some of the things were sort of counterintuitive.”
For instance, Snow challenges the idea that shared values among team members are of primary importance, although he’s a big proponent of having a shared sense of purpose. He says that disagreement is the seed of innovation, provided managers are capable of balancing conflicts in a healthy way. (For more of Snow’s team-building insights, check out the sidebar.)
Snow backs up his book’s claims, not only with his own anecdotal experience, but also with thorough research into some of the world’s most effective teams, from pirates to the Wright brothers. In the process, Snow has found himself back in his element: telling stories.
“One of the most important things that we can do as leaders, as founders, as team members is to share our personal story of what we care about and why we’re doing what we’re doing,” Snow says
It’s fitting that a journalist and the founder of a company that facilitates storytelling would feel this way, but there’s plenty of brain science to back up Snow’s claims. Research affirms the importance of storytelling as a tool for building relationships and inspiring care within organizations, families, and nations.
“Humans are built for stories; that’s what we do all day long,” Snow says. “So use that. But do it about things you care about, and you’ll be amazed at how much that affects how you work with people.”
Shane Snow’s Counterintuitive Take on Team Building
Shared values aren’t all they’re cracked up to be.
“Yes, having strong shared values is really good for unity, it’s really good for morale, and it’s good for being able to make hard decisions together,” Snow says. “However, having really strong shared values has a downside, which is that it has the potential to squash things that are helpful to innovation.”
Snow points to the example of a group of people in a rowboat that’s heading toward a waterfall. Ideally, any person in the boat should feel free to point out the upcoming risk. But if pointing out the waterfall would violate the group’s shared values in some way, people might be less willing to speak up—and that puts the whole boat in danger.
As Contently grew, Snow noticed that hiring a team made up of very different people caused more problems than if he’d hired more like-minded folks—but it also inspired more creative ideas. “I found two heads are not better than one,” he says, “unless those heads think differently.”
“It turns out that the best thing you can do to unify a group of people (especially a group of people who are very different from each other) is not a shared list of values but a shared purpose,” Snow says.
That purpose should become the guidepost for how the team makes decisions. Each choice should come back to the central question: Will this advance us toward whatever we believe to be an important purpose? “It allows you to have more flexibility on the strategy of getting there, while still having that guiding principle,” Snow says.
- The two realizations Snow had that sparked the idea for Contently
- How Snow transitioned out of his role as founder and returned back to his former love of journalism
- Snow’s counterintuitive advice on team building and how it relates to innovation
- One of the most important things we can do as leaders and team members to build relationships
Full Transcript of Podcast with Shane Snow
Nathan: The first question that I ask everyone that comes on is how did you get your job?
Shane: How did I get my job? This job that I’m doing right now?
Shane: So this one, it’s some sort of weird cross between freelancing and unemployment. What I’m doing right now is I’m founder-at-large at the company I started eight years ago. So I started Contently, a content marketing company in 2010. And then the first of this year, so after seven and a half years, I transitioned out.
So I pop in every week or two to say hi to people. I do some press stuff. But I’m mostly kind of a figurehead at this point, and much more capable when people are running it. So sort of unemployed. And I am back to journalism, which is my first career love in that. How I got that job is I started asking people questions and then writing the answers, and questioning those answers, and writing more answers.
And so it’s one of those jobs that I think anyone can do if they put their mind to it. Getting paid, on the other hand, that’s the tough part of the job.
Nathan: So, man, Contently is massive. Like we, at Foundr, work with a lot of writers and it’s pretty much every time, we say, “Can we get your portfolio that you want to show or any pieces, or show us, you know, some work that you’ve produced that you’re really, really proud of?” and they always link us to Contently.
So like how did that…
Shane: Oh, I’m so glad to hear that.
Nathan: how did that all come about, man? Like, you know, I’m really curious. Like, so you started off as a freelancer. Like, is Contently your first kind of startup? Like, where did it all start? You’re a journal at heart. So like, how did it all start, man?
Shane: So I grew up in Idaho, a small town, and I was one of the few really nerdy people that grew up in this town. One of the other ones is actually my co-founder at Contently. So growing up, being really interested in computers and science, and engineering, and taking things apart, and I basically started my first little internet startup when I was a teenager.
It was like a greeting card site, like send your friend, you know, a webpage with dancing smiley faces on their birthday, like that kind of thing. And so I made some decent money doing that in high school. It was during the early days of the internet, where ad prices were insane. So I made some money to the point that it worried my parents.
And they actually made me…I was 16 years old. They made me shut the website down because they were worried. They didn’t quite understand the internet. They were worried that I was doing something illegal, some sort of computer hacking. And they also were worried that I would not learn the value of hard work if I just got rich really young doing this internet stuff.
And I was furious. I was so mad at my parents. And we had these fights. It’s actually…I love my parents, and we have a great relationship now. But it’s almost a little bit of a sore subject still if it comes up. They don’t listen to podcasts, so it’s fine. But no, I love them.
And I’m actually grateful for this experience. Because we had all these fights, you know, and I said, “Well, you’re not paying for my college. How am I going to pay for college?” And they said, “You’ll figure it out.” And they made me get a job at the gas company, where I literally was spray painting gas meters and digging trenches, doing this awful manual labor. And so I kind of vowed to myself that I would never do that again, and that I would never let anyone tell me what to do for my job again.
So when I went to college, I decided I was going to start that internet thing back up. And so I built a bunch of websites to pull myself through school, selling things in e-commerce and doing some advertising stuff, and just anything I could do, and that’s how I survived during school.
And at a certain point, I decided that, you know, the thing that I always loved doing as a passion my whole life was reading and writing. And so I decided, “Hey, I want to write about startups.I want to write about technology. I want to write about science and people that are inventing things and making businesses out of them.” So I went to journalism school to get trained to do that, and how I paid for journalism school was these website, little kind of mini-startups that I was building, selling things, literally, like rototillers on the internet and saddles because I was from Idaho.
You can sell…You know, people buy saddles for their horses on the internet. Who knew? So I sold a lot of those. So I was doing that sort of thing and making enough money to scrape by. And then, as I got out of journalism school, I was writing for magazines like WIRED and Fast Company, writing about businesses doing stuff in science and tech.
And I got really inspired and decided, “Hey, I want to do this again. I’m learning all this great stuff from all of these companies that are, you know, changing the world. Maybe this journalism thing is actually teaching me stuff that can help me do better at my next startup.” So I was thinking about that and then, basically, what happened is I had a bunch of friends from journalism school start reaching out to me because they were all freelancers.
And I was good at freelancing because I’d been kind of doing that entrepreneurship/freelance thing, you know, my whole school experience, and they knew that. And they knew I was good at, you know, websites and things. And so I had people reaching out to me saying, “Hey, how do you build a website so that you can show off your portfolio to clients? And how do you do your taxes once you do freelance work? And, you know, how do you do internet marketing?”
And so I realized that there’s this whole group of people who are way better writers than me, way better journalists that were doing way worse than me because they didn’t know how to do that entrepreneurship hustle thing that I’d been doing with all my little startups. And so that kind of was the thing that led to the idea for Contently, which originally was, “If we can build a little website or a little platform that helps journalists do all the little things that have nothing to do with the craft…if we can build that, get them all to come, help them build a portfolio so they can market themselves, showcase their work, make a blog to teach them how to manage their freelance careers, then we collect enough of these people, and we can start brokering work for them like a talent agency and take a little cut.”
So that was the original idea. And then what happened is the kinds of clients… We said, “We’re only going to work with clients that are going to pay good prices. We’re not going to do this sweatshop labor thing.We only want good prices for people that have training.” And it turned out very quickly, we realized that the kinds of companies that were willing to pay really good prices were not newspapers that were sort of struggling. It was brands like Pepsi and American Express that wanted to write really high-quality blogs or do social media stuff, or what’s become known as content marketing.
And a lot of them wanted to do like research papers and reports, and things that, actually, the skill set of a journalist is really good at. And so we leaned into that and then, basically, over the next several years, started building tools to help those brands do things with that content. So you hire some reporters to shoot some video or to write some articles for your website or your blog, or whatever, but you also need to manage that process.
And you need to know, “Is this working? Am I building an audience?” and kind of a billion other things. And so we just built software for that. And so, suddenly, I found myself as a freelance journalist with this sort of one-man-show background of building little tech things on the internet. Suddenly, I found myself with a couple of partners at the head of this company that was dealing with, you know, like every major brand, you know, in America and like 100,000 hungry journalists and photographers and videographers around the world who had built portfolios and were asking for work.
So it’s sort of a crazy thing that happened. And then, you know, suddenly, we’re a software company that makes… it’s sort of like Salesforce for content marketing is kind of the best analogy, which is just so different than what I thought would happen. So I kind of, you know, followed, I guess, the problems that the people we cared about were facing and just kept building stuff and doing stuff.
But it was a rabbit hole that took us to a very different place than I imagined.
Nathan: Yeah. Wow. And like, is Contently like still basically where you spend the majority of your time now? Are you working on other projects or…
Shane: Yeah. So at the start of 2017, I hired a CMO to… I realized a few things. One, I realized that my job had gone from the guy who builds stuff, you know, and makes decisions and all of that, and hustles, the stuff that I was good at, and the guy who writes things, which was what I love, I went from that guy to the guy who finds other people to do those things and then helps them to not fight, basically.
And so, you know, I spent a few years agonizing over how to become a good leader and a good team-builder and all of that. And then as we grew, we got to a point where I realized that I was not the right person to take our organization to the next level. You know, we grew it to something like $15 million in annual recurring revenue in U.S.
dollars, you know, in software. And then, who knows how much money is, you know…I think the last data I saw was something like $46 million a year being paid to freelancers, which is awesome. We’re not taking that money, but freelancers are getting it. Yeah. So I built it to pretty big. But growing from that to 10 times that size, I was like, “I am not capable of this.”
And I was kind of getting a little tired, and I have creative ADD. So start of 2017, I hired a CMO and, basically, gave her the reigns. And I went on a two-month sabbatical so that I could kind of clear my head and let her have a chance to kind of assume the mantle of the leadership of my department, you know, about 40 people.
Instead of going around her and going to me, they now had only her to go to. And then I came back, and I basically was an advisor to her for the rest of the year while she ran the department and, you know, built, you know, a team of VPs under her. And then, at the end of the year, I stepped aside and, basically, yeah, I’m founder-at-large.
So like, I speak at conferences on behalf of the company, you know, I go to the big, important events, and I’m there for people. But my job now is writing. And so I’ve been working on a book about teamwork based on the things that I have been learning, and so I’m publishing that this year. And then, you know, I’m kind of digesting all the lessons that I’ve learned in this last little bit, and then helping kind of push the company along in little ways.
Yeah. And I mean, that whole kind of cycle of going from, you know, just on my own, this huge journey, this company with hundreds of employees and all these users to back to being on my own, and I still am attached to the company, but I’m kind of back where I started. But having learned a lot, it’s almost like a hero’s journey of some sort, and you go to sort of the bottom of the pit, and then during that startup process.
And so, you know, the company, it’s still going. It’s doing great. It’ll, you know, have an outcome of some sort. You know, someone will buy us, or we’ll go public at some point and pay our investors back. But now, it’s kind of like being a parent and your kid is at college and, you know, you’re there for them when they call and need advice. But you’re just kind of seeing what happens. So it’s a strange place to be in.
Nathan: Yeah. I see. And, yeah, so you’ve basically gone full circle.
Nathan: Awesome. And so talk to me like around…so you’re just about to launch your new book, Dream Teams. So talk to me about the whole premise of the book and how it came about. So along the way you’ve learned like, how to scale a company through just amazing people. And, yeah, dude, tell me?
Shane: So there’s a few things that I started noticing when my job became more about team-building and team management. And some of the things were sort of counterintuitive that, you know, the more different people were who we hired…We kind of had this nice ragtag group of misfits, you know, at a certain point, and there were more problems because of that, but also much more clever ideas.
And I started looking around at examples of amazing teams, you know, in other tech companies, other startups. And then I, you know, started looking at history of what makes the difference between amazing teams and normal teams, and, you know, incredible groups that beat the odds, and kind of found that this ragtag-group-of-misfits thing is a theme.
And I sort of dove into that. And there’s a paradox, basically, that I found, which…and some of this will sound obvious once you hear it, but it’s extremely important. It’s that two heads are not better than one, unless those heads think differently. So if you have a whole group of people that all think the same or similarly, they’re only going to be as smart as the smartest person in that group.
But if you have a group of people who think differently than each other, they have the potential to find solutions and to see things that no individual member could. But the problem is a group of people that think differently is also more liable to have problems with each other, to have miscommunication, to have conflict, maybe even have competing motivations. And so there’s this sort of weird balance that you kind of see that you kind of want to get, which is stoking this what psychologists call “cognitive friction”between different people and kind of keeping your team in this zone where there’s all these possibilities because your ideas are doing battle.
But, you know, making sure that it’s the right ideas that are doing battle and making sure that that battle doesn’t, you know, turn into a war. And so that was really interesting, and I started noticing lessons like that. And basically, what the book is about is it’s my adventure into understanding incredible teams, and the psychology and the subtle interactions that lead to them, but through the lens of really fun stories and history about like pirate gangs, you know, and buddy cops and things like that.
But there’s a lot of things…it basically follows…I tried to go into common wisdom about teamwork and collaboration that it turns out either is wrong because of new science is showing that it’s wrong, or it’s wrong because we just have gotten it wrong. And so that’s the idea is that, you know, there’s common wisdom that we have that makes for okay teams.
But the most incredible teams out there and in history do a lot of things that go against that common wisdom. So it was nice to be able to workshop these ideas while I was, you know, building my team. And a lot of them, you know, very much are a product of that collaboration process. But it’s also a little bit outside of just this sort of, you know, tech business that I was building because it really gets at this sort of fundamental thing about humans, whether we’re building a tech company, or we’re running a liquor store or a coffee shop, or whether it’s a family, you know, two parents trying to work together to work things out, or whether it’s communities or, you know, our nations pointing weapons at each other, there’s this similar kind of dynamic at play of, “We can be stronger and smarter and better together because we don’t see things the same. But that’s also the source of kind of all our problems.”
Anyways, so that’s what it ended up being about. I’m totally rambling at this point. But it’s all connected.
Nathan: All right, fine. Keep going, man.
Shane: It’s all connected, which I like.
Nathan: Yeah. Amazing. So, you know, one thing that I’ve been learning over my journey around, you know, scaling a company is, once you kind of find product-market fit, I think, you know, one of the most important things you can do to take your company to the next level is obviously, like, building a team.
But really, just finding the most incredible people that have essentially done what, you know, like, you need like a function done, or whether they know how to do it and they’ve done it before. And if you can build like this dream team or like Avengers, like an Avenger team of these incredible people, you can just watch like…You know, because you can only do so much as a founder.
Or your founding team like, you know, your group of co-founders, you can only do so much. And that’s something that I’ve been quite obsessed with is just hiring and finding really, really great people. So I’d love to delve more…
Shane: It’s surprisingly hard, right?
Nathan: Oh, it is…
Shane: It’s harder than you imagine.
Nathan: Dude, it is so hard, especially when you’re in Melbourne. But it is possible. It is possible. I am finding some absolute superstars to join us, and we’re building like this team of Avengers, like A-players. Like, it’s amazing, right? But one thing I’m curious around, where you said around, you know, you’ve found that you don’t want everyone to think the same, and you want people to, I guess, think differently or have different approaches to things, different thought processes, different experiences that they’ll bring to the table.
Like, one thing that I’ve learned, and I don’t know if this is contradictory, I’d love to hear your thoughts, is around, like, when it comes to your values. Like, your values are really, really important and key to shape the people that you want to welcome into your company, because your values set your culture and then your belief system as a company.
And basically, your values, they’re an extension of yourself or your co-founders, around your own personal beliefs, right? And that, you know, if you use that as the premise or kind of your rulebook of the kind of people that you want to join your company, don’t you tend to find people that are similar to you because you want them to think the same as you in that sense?
You know what I mean?
Shane: It’s an excellent question. This is one of those really tricky paradoxes that I found in researching this book, and it’s something that makes the difference between good teams and, like, impossibly amazing teams. And so, yes, having strong shared values is really good for unity, it’s really good for morale, and it’s good for being able to make hard decisions together.
However, having really strong shared values has a downside, which is that it has the potential to squash things that can be helpful to innovation. That it turns out, the research shows that companies that have really strict emphasis on shared values, on core values, tend to get disrupted more easily.
And, you know, the sort of cheesy analogy is, if you’re in a rowboat and your team is rowing down a river, if someone sees a waterfall, you want them to be able to point it out. But if the person who sees the waterfall can’t point it out because it, for whatever reason, goes against some, you know, way of doing things that has been specified, then that puts the whole boat in danger.
So there’s sort of some trickiness around it. A lot of times, when we talk about values at companies, we’re talking about wish-list behaviors, so we wish that people would behave this way in a given situation. And that’s very different than the kinds of values that are a little bit more sort of noble and universal. So, you know, 60% of Fortune 500 companies in America have integrity as a value.
Turns out that any company that doesn’t believe in integrity, that doesn’t practice integrity is going to have problems. Right? They’re not going to be a great company, and people are not going to want to work for them. So it’s almost like, “Why do you need to say that one?” But, you know, if you say it because it helps people feel good, then great. But, you know, when we start to get more specific about values like, “The customer is always right,” that could be great.
And that could really be a good focus, you know, for a lot of people, until a customer does something that could ruin your business. And you need to have the room for people to say, “I don’t think the customer is right,” or you put things in danger. And so there’s a way that the values thing can actually sort of metastasize and escalate in a way that makes people feel not included because, you know, they are different and they believe different things, or makes people feel like they can’t speak up.
So I think the thing… And you said something that I think is important, and it’s in this question. It’s all about the distinction. It’s about not conflating things. And you said something, “strong beliefs.” It turns out that the best thing you can do to unify a group of people, especially a group of people who are very different from each other, is not a shared list of values, but a shared purpose.
A really strong, overriding shared purpose that that becomes kind of the guidepost for how we make decisions, “Is this decision going to lead us to get to this thing that we believe is an important purpose?” So it allows you to be more flexible on the strategy of how you get there, while still having that kind of guiding principle. So my favorite example of this, actually, of getting this really right is Google.
So Google’s, their mantra internally was almost cheeky, almost making fun of kind of a long list of corporate values that are sort of the same. And I’m not saying that having values is bad. I’m just saying to be careful, right? But Google is this great example.
They said, “You know what? Our only value here is, ‘Don’t be evil.'” And it’s sort of like, “No, duh. Don’t be evil.” But that was like, “Okay.” Everyone gets it. It’s a reminder. That’s a nice and important reminder.” But then what they did is everyone at the company, for years and years, could recite the purpose of the company, which was to organize the world’s information.
And, gosh, if you care about organizing the world’s information, if you get how important that is, that’s incredibly inspiring, and it will help you to make good decisions. And then, when you look at situations, you can look at them on a much more custom, case-by-case basis, “We have this problem to solve. What are the ways that we can potentially solve it?”
You know, and Google also looks for people with certain skills, certain attributes, certain tendencies. That’s all fine. But they’re flexible about all of it because they know and they…you know, I think as the bigger it gets and things change and all that, I don’t quite know about the modern Google versus the first, you know, 10 years of Google. But they knew that they were going to need all of the different kinds of people with all the different kinds of lenses on problem-solving, but they were also going to need them to be unified.
So that’s a long answer. But in Dream Teams, Chapter 6 is all about that question and that paradox. It’s about the idea of, “You need to build an army to do something really important. How do you get those people to work together, even if they’re different?And how do you deal with this ‘all values are not equal’ kind of question?”
Nathan: I see. And, you know, for most people in our audience, they would be just starting to build out their team or just starting to hire, or just starting to scale up. So, you know, when it comes to building an amazing team, like, what are your thoughts on, I guess, remote versus local or versus a hybrid, a combination of remote and local?
What are your thoughts, feedback? What’s your feelings there?
Shane: You know, it’s interesting because I’ve been thinking about this. You know, when I start another venture at some point, you know, I want to design the way that I built, you know, the team structure and the collaboration process very deliberately from the beginning. That it’s easier to do things right from the beginning than to kind of fix them later.
And, you know, the principle that I really love when working with people, especially as a team leader but I think in general, is this idea of freedom in exchange for accountability. So let people work how they want, as long as they are accountable for getting things done. And that’s kind of hard to manage.
As a leader, you have to be very vigilant. But what it does, it’s a nice contract you can have with people. Netflix is famous for having a culture where they do this. They say, “Work where you want. Work how you want. You know, your approach to taking things on is up to you and be whoever you want to be. But you’ve got to deliver, or we’re going to get rid of you, and we’re going to find someone who can deliver.”
So, you know, with this great freedom is this great responsibility, you know, to push the team forward. So I really like that. And so to me, I think the question around remote or in-office or hybrid is going to revolve around my ability to manage people and to keep them accountable.
If I can pull that off with a remote or with a hybrid structure, then I say, “Yeah.” Because I think you’ll end up being able… The pool of people that you can work with becomes bigger, right? You can get those truly incredible people and their different specialties wherever they live in the world, and you can provide more of that flexibility.
The thing is, is you can’t be very hands-off in terms of paying attention to their output and what they’re doing. You need to be really involved, I think, in terms of making sure you don’t go days or weeks without seeing what they’re doing. Because you want to trust people, but, you know, you’re going to need, in the beginning, to work together enough that you can build that trust between each other.
And then you’re going to need to check in every once in a while, to make sure that people are okay and to make sure that, you know, something hasn’t happened where, you know, they’re not working, basically. But I think if you can get to the point where you trust people, then remote is great. I mean, it provides so much flexibility. So I think the mistake is to be so rigid that, you know, you miss out on the opportunities to work with amazing people.
And that might just, you know, have a… It’s like at Contently. When we started having people, employees who had kids or who were having kids, we realized that it was important to let people work from home and stay with their kids. And, you know, one of our employees, I remember, every Friday she worked from home so that she could always have one day at home with the kids.
And having an environment where you can do that, so you can retain the talent that you want to retain, that’s good. And so, I guess, you know, if you have a completely remote team and you just can’t manage them, you don’t know what people are up to and you can’t keep them accountable in exchange for that flexibility, then that’s worse than having an in-office team.
And having a hybrid team where people who are remote feel like they’re not part of the team, they feel bad like they don’t get, you know, the attention that other people do, or where people in the office are bitter because some people get to work from, you know, the beach, that’s not good either. So I think how you manage it, you know, and your ability to do that is the answer to that question, not which one is optimal, I think.
Nathan: I love what you said, “freedom in exchange for accountability.” So like as an example, one thing that we do at Foundr is, you know, we do quarterly strategy days. And, you know, we set the scene and the vision for the year and our goals. And then we have, like, what we do, I’m not sure if you heard of it, like a traffic light reporting system, so everyone, each has their own goals that they’re accountable for, and then we just check in once a week.
Yeah. That, you know, I’m the same as you. I don’t really mind that much as long as, yeah, we, you know… You quickly find out if that person isn’t doing what they say they’re going to do, right?
Shane: Yeah. What’s the traffic light thing? Is it like red, green, yellow? How is that?
Nathan: Yeah, red, green, yellow. So like, it’s like a KPI dashboard. So we all have our goals. Like, so our Content team has goals around, you know, keywords and traffic that those keywords are being driven, and then also you need visitors. And then, you know, our Product team might have goals around shipping a certain amount of product. Or, you know, our Marketing team might have goals around, you know, conversion rates for certain email or marketing funnels.
And, yeah. And then we just check in once a week and we’re either in the green, if we’re on track for that goal for the quarter, or we’re in red where we’re not on track, or we’re, you know, in the middle, orange or yellow. Yeah. It builds a really strong, winning culture. I didn’t come up with this concept.
One of my mentors, Mitch Harper, taught me this. But then, also, it’s a framework from a book called Scaling Up by Verne Harnish.
Shane: I know. I know that book. I haven’t read it. You know, it’s similar to something that I did for a long time with my team, which I forget where this comes from, but it’s PPPs. So every Friday, I would add a calendar invite for 15 minutes on everyone in my team’s calendar as a recurring thing that said, “Send Shane your PPPs,” and it was progress, plans, and problems.
So progress was, “What did you finish this week?” Plans are, “What are you doing next week?” And then, problems is, “What are problems that need my attention? If it doesn’t need my attention, then I trust that you got it.” And what was nice about it is there was this, like, level of accountability and on a weekly, not on a daily, because day to day things, you know, happen.
But it gave me an opportunity to see what was going on with everything, and then I would always follow up, you know, and it generated conversations. And whether you were out of town and you sent me this, or whether you were in the office and you sent me this, I’d follow up and we’d talk about it if we need to, and then I could spend a lot of my…Instead of doing these one-on-ones where you’re like, “What have you done lately?”
I could do one-on-ones where I take people to coffee and see how they’re doing, from a personal standpoint, offer, you know, kind of my emotional support. And then, you know, kind of build that trust and rapport so that during the weekend and with these PPPs, I could then push them to go further, you know, than they maybe think that they can go. But because we have this trust and because I’m getting this accountability from them, I don’t think it was the perfect process, but I like that kind of idea of there is a formal accountability.
But it’s also coupled with this knowing that you care and showing that you care by giving people, you know, freedom and not, you know, breathing down their neck, you know, minute after minute. I like that.
Nathan: Yeah. Yeah. I think, it goes without saying, like, when it comes to building a dream team, people can’t be micromanaged. Yeah?
Shane: Yeah. Yeah. There is kind of this entrepreneurial nature to, you know, a lot of dream teams. The individuals on them, often tend or we know of a plurality of them or a majority of them often tend to be ingenuitive and good at figuring things out on their own.
And then, when you combine that with this sort of sense of shared consciousness where you know, “If I bring this thing to this person, they’re going to kind of do X, Y, or Z.They’re going to figure out the problem in this direction.” Or, you know, you see this in amazing sports teams that they can, you know, throw the ball or pass the puck without looking, and they know that their teammate is going to be there.
Being able to combine that, you know, with that other stuff, with, you know, kind of the resourcefulness, that is often kind of… And a through-line, no matter, you know, what skills people have and what different perspectives people bring, they often tend to have those kinds of things, the ability to read each other and trust each other, and an ingenuity, sort of entrepreneurship factor.
Nathan: So like, knowing that that person has your back, or the whole team has each other’s back, incredibly powerful.
Shane: Super powerful. Yeah. It’s…
Nathan: What if the… Please go on. Sorry.
Shane: I was going to say, I think a really powerful combination is knowing your team has your back and also being able to have conflict. So knowing that you have complete personal support, emotional support from your team, they’ll do anything for you, you feel safe, but that you can then also debate and fight and argue.
Or it doesn’t have to be a fight, but you can really have a battle of ideas while feeling safe. That’s an awesome combination.
Nathan: Yeah. Healthy conflict is good conflict. Yeah. I agree. Now, I’m curious, how do you cultivate this? How do you cultivate a team like this? So let’s say you’re hiring and you’re trying to find people with the experience.
Like I said, like, you know, which I think is key, you’ve got to find someone that’s done it before if possible, and just has experience doing the thing that you need to do, and to build out your vision and what you’re building at your company. When you start to build out this team, how do you cultivate this?
Shane: Yeah. I mean, there’s a few things. I think being deliberate about the hiring is really key. I would also say, if you’re trying to solve novel problems or you’re trying to break new ground, you want people who have experience, but who are also flexible thinkers, or you want to put them together with people who can kind of provoke them to think a little differently.
You want to have some descent. You want to have some provocation. There’s the, you know, the whole thing with the A-Team, like, the looks, the brains, and the wild card? You know, having a wild card in the room sometimes is really helpful. Or maybe that can be you, right, as the founder. But someone who’s pushing people when everyone’s like, “Yeah. Yeah.
Great. Let’s do that,” like, “You know what you’re doing. Let’s do it.” Having someone who can be like, “Well, what if,” or, “I don’t think so,” having that kind of element is really helpful. But how do you create the environment with that kind of healthy friction? It’s tough. But part of that is the combination of who you put together and who you include.
And part of that is, as the leader, you can actually stoke that. One of my favorite things, one of my favorite stories in history…I’ve kind of been telling this story a lot lately in live audiences. Hopefully, not on air much. But it’s, in the book, there’s a story of the Wright Brothers.
And they had this process where, when they were trying to solve a problem, they’d actually start these debates and they would escalate kind of the tension in the debate, like they would get to the point where they were yelling at each other. And they were brothers, so they could kind of do that without, you know, freaking out too much at work. But they’d have these really healthy debates, and then what they would do is their rule was, at lunch, they had to switch sides.
So they’d eat their sandwiches, and then Orville had to debate Wilbur’s side, and Wilbur had to debate Orville’s side. And it was really cool because it kind of forced them to let go of their ego in this equation. But it also allowed them to really kind of amp up, you know, the war of ideas. And you could actually do this, you know, as a leader, and I do this all the time.
When someone is arguing a case for something or, you know, everyone is kind of, you know, making a case for something, assign people to take the other side. And sometimes they’ll take the other side in kind of a weak way, in like a, “Oh, yeah. I guess, we should play devil’s advocate. I don’t really believe this, but you could say this,”and actually push them to really argue the other side.
And we all kind of have it in us to do this. So that’s one thing that is sort of a really…and you can even do this with yourself, when you’re brainstorming ideas. After you’re done brainstorming ideas, then force yourself to brainstorm, “What’s wrong with this? Or what are the ideas that would kill this plan? And, you know, what’s the other side of this, or whatever?”
You can do that with yourself. It’s like a nice, little hack for getting yourself to think a little bit differently because you have it in you. And other things that you can do is you can invite people into the room to participate who, you know, don’t belong, basically, and this can have two benefits as long as everyone participates. One benefit is just having someone who’s different in the room often gets people to think a little bit outside of their normal way of thinking.
My favorite example of this is, you’re planning the redecoration of a hotel, so you’re all sitting around, you know, the conference table. You’re talking about how you’re going to remodel, or whatever. And halfway through the meeting, if someone comes in, in a wheelchair, everyone in that room is going to suddenly think differently about the project. The same thing happens when… There’s these great studies of, you know, they had American democrats, they gave them a murder mystery to kind of try and solve, and then they had to go and debate someone of what they thought the answer to the murder mystery was.
And when they were told they’d debate other democrats, you know, they did okay. They did however they would do. But when they were told they would debate republicans, even though it was a murder mystery, not about politics, they would actually have better arguments. They would think a little bit harder, a little bit differently. It turns out that when you’re collaborating or debating with someone who’s not quite like you, you pull out more stops.
So there’s things like that that you can kind of do. You can also, if you’re, you know, a leader and you’re trying to come up with ideas together with your team, you can start…instead of just saying, “Every idea is a good idea, and let’s brainstorm,” that tends to not actually produce very good results. But if you start off with a couple really extreme ideas, then that gives people kind of implicit permission to go a little bit beyond what would normally be safe to say in the room.
So there’s this study that I really love, you know, I discovered, where they did these kinds of exercises, where they had people sit around a table to brainstorm ideas for something. The one I remember in particular is a mobile finance app for managing your finances and your budgets, and they wanted people to brainstorm features for this app. And when they just asked people to brainstorm features, they’d come with okay ideas.
But when they started it off by saying, “We’d like you to brainstorm features for the app and, you know, here’s an example. You could actually have like a wristwatch that gives you reminders on the app. And if you ever fail, you know, to complete the reminders, then it has a little razor blade underneath it, and it’ll cut you on your wrist.” And it’s like, “Holy shit, no one would ever do that.” Like, “That’s a terrible idea. It’s a terrible feature. It wouldn’t work.It’s, like, too crazy and extreme.”
But when they’d start the brainstorm session off with that sort of thing, people would actually propose better ideas than they would otherwise. And it’s kind of because like, “Well, if we can throw out, you know, the cut-the-wrist idea, then maybe this thing that I have in my head that, you know, is a little bit risky for me to say in this group setting is not so risky.” So there’s lots of little sort of hacks you can do to kind of stoke that cognitive friction inside of your team.
There’s a whole bunch of stuff in the book, and I have stuff on my website around that too. But generally, the idea as the leader is you want to look for opportunities where you can get different brains to mesh together. And then you want to kind of provide guardrails so that if it gets personal, you tell people to switch sides or, you know, you intervene and bring it back to being about ideas. And, you know, it’s a different kind of leadership, but I think it’s a more innovative kind of leadership.
Nathan: Yeah. Amazing, man. And look, dude, we have to work towards wrapping up. This conversation went so fast. I could talk to you all day about this stuff. Because I’m really obsessed with team-building as well, and I’m deep within just HR and just trying to find the best possible people to join us. But look, just a couple of final questions.
The first is, where’s the best place people can find out more about yourself and your work, and also more about Dream Teams? And then, lastly, just anything that you’d like to finish off with. I know we didn’t even get to touch on content marketing and the power of it, and you’re obviously quite masterful at that.
But just any final kind of words? Because, yeah, man, we have to work towards wrapping up.
Shane: Well, you can find me at, it’s just my name, shanesnow.com, and that has links to everything from Contently to my books. And, you know on the content marketing theme, I would say, one of the most important things that we can do as leaders, as founders, as team members, is to share our personal story of what we care about and why we’re doing what we’re doing, and to identify the emotions that we have for that.
So, you know, that thing about Google and the purpose, or whatever? You know, clearly the founders had a story that they shared with their people about why they cared about this and how it made them feel. There’s something really powerful about that, of getting people to also care enough to support you or to join you or, you know, to submit their resume, or, you know, to be on your side.
And also, if you’re working with people who, you know, you’re uncomfortable with or you haven’t quite gotten to that place where you can click, sharing your story, and, you know, not like getting too personal, necessarily.
It don’t have to be personal. But talking about who you are and why you care about the things you’re doing is incredibly powerful. And it sounds simple. There’s actually a lot of brain science that backs this up that, you know, we tell stories and that, in our brains, makes us care and it builds relationships. You know, and humans are built for stories.
That’s what we do all day long. So use that. But do it about things that you care about, and you’ll be amazed at how much that affects how you work with people.
Nathan: Amazing. Well, look, thank you so much for your time, Shane. It’s an absolute pleasure to connect. I really appreciate your time, and this was an awesome interview. Thank you so much.
Shane: It’s my pleasure. Thank you.