The Shane Snow Hypothesis: A Leader’s Role Is to Be the Facilitator of Great Debates

Shane Snow is the co-founder of Contently and the author of three books including his latest, Dream Teams: Working Together Without Falling Apart. In this episode of the Product Science Podcast, we discuss how the best teams aren’t just dominated by one person’s ideas or process—they’re smarter than the sum of their parts.

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Questions We Explore in This Episode

The Shane Snow Hypothesis: A Leader’s Role Is to Be the Facilitator of Great DebatesHow did Shane’s experience starting businesses online in high school inform his startup? What is the story behind Contently? How did business shift and pivot as it developed, and what did they look at to make those decisions? What were their initial hypotheses, and what did they learn? How did they navigate a new industry? What is a key failure they made along the way?

How did Shane’s journey with Contently lead him to write Dream Teams? How do you resolve internal debates in your organization with data? How do you keep conversations focused on the realities of the market and avoid getting too personal? What does Shane mean when he says a leader should be the facilitator of great debates? How do business leaders create a great environment and culture?

How do you get your team to be smarter than the sum of its parts? What does Shane mean when he says that Contently had a “no cowboys” policy? How did they use rituals to bring their teams together? How does camaraderie make it safe to disagree? What other things did Contently do to foster the culture they wanted? What would Shane do differently?

What lessons did Shane learn about building diversity into the DNA of a business? How would he hire differently? How do you get more specific about cognitive diversity? How do you identify it when you’re hiring? How do you look past a resume to understand someone’s thinking? How does Contently use remote workers to find the best person for a job?

How did it build on ideas from his earlier book, Smartcuts? How do you push your thinking to be different? What can we learn from the story of Embrace? What would it look like if you had to do your same product process but ten times cheaper? What if you had to make your product ten times more profitable?

Quotes From This Episode

Our process was like the scientific method. We had hypotheses about how the world was changing so we created the startup with the goal of testing these hypotheses to see if a business was there. - Shane Snow Click To Tweet As a leader, my role is to be the facilitator of great debates. Put people with different perspectives together and get them to open up. Reward people for pushing the ball forward, not for being right. - Shane Snow Click To Tweet We don't want culture fit, we want culture add. We're bringing you in, we're hiring you because we want you to contribute something that we don't already have and being really clear about that and celebrating that. - Shane Snow Click To Tweet Make the hard decisions with compassion. There are other people whose jobs and lives are on the line that you have to make this hard decision for, but it's okay to make a little less profit if you take care of people. - Shane Snow Click To Tweet


Holly Hester-Reilly: Hi and welcome to the Product Science Podcast where we’re helping startup founders and product leaders build high-growth products, teams, and companies through real conversations with people who have tried it and aren’t afraid to share lessons learned from their failures along the way. I’m your host, Holly Hester-Reilly, Founder and CEO of H2R Product Science.
Holly: In this week’s episode, I caught up with Shane Snow, an award-winning journalist and entrepreneur and the best-selling author of the book, Smartcuts, The Storytelling Edge, and Dream Teams. I reached out to him myself after reading Dream Teams. I thought it was fantastic, so I had him on the show to talk about culture, teams, startups, and all sorts of things. Here’s our conversation.
Holly: This week on the Product Science Podcast, I’m excited to introduce Shane Snow. Shane is the author of Dream Teams: Working Together Without Falling Apart, which I read last year and just loved so much that I had to reach out and ask him if he would come and talk to me on the podcast. Shane is also a founder, so I think he’ll have a lot of interesting things to share. Shane, do you want to give us sort of your short background for people to hear how you describe yourself?
Shane Snow: Sure. Yeah, and thank you for having me on. How I usually describe myself is, if I have time, I tell them I’m from Idaho and my dad’s an engineer and my mom was an educator. I grew up really loving books and really loving taking things apart and understanding how they work. That has kind of been the running theme in my career as I’ve done startups and I’ve had a career as a journalist and I’ve most recently, in the last decade, been running a company for most of that decade and written three books along the way to take apart the world in a couple of areas and reassemble it in order to learn how to do business better. It’s kind of applying science and sort of an engineering mindset to innovation, to teamwork, to business challenges. Now, after all of that, I am going around and working with businesses to help make their businesses better based on these things that I’ve learned from these two treks.
Holly: Awesome. That gives us a good overview. Before we go in some back and forth conversation, I’d love to hear a little bit more about what were the companies that you helped build and how you ended up deciding to take that step.
Shane: In high school, a couple of friends of mine and I all started internet businesses. It was the late 90s, we were teenagers, and somehow it was surprisingly easy to make money on the internet. I have a greeting card site, like a send happy birthday cards to your friends kind of thing and early internet days, I was able to make quite a bit of money from that just with advertising. Ad rates were incredible back then, so that was my first business. Then, in college, I did a lot of programming and I was sort of a freelance programmer, built a bunch of websites for people. Then, I built some eCommerce websites of my own. I’m from Idaho, like I said, so one of my sites was literally selling saddles, like horse saddles online and some people will buy a saddle from the internet. Who knew? I had a bunch of little things like that and kind of a series of escalatingly ambitious projects and eventually I decided to go to journalism school, so that I could write about business and technology and science.
Shane: Then, from that experience, I ended up deciding to co-found a company called Contently, which initially was about helping freelance journalists to get work, so kind of like a talent exchange. Almost like that newfangled talent agency on the internet to help freelancers who used to work for the New York Times, but now have been laid off. That sort of thing. That turned into a software company that makes content marketing tools. I kind of fell into what became a pretty big company. We raised I think $19 million in total from investors over a few rounds. There’s hundreds of employees, hundreds of thousands of users, and we have hundreds of Fortune 1000 paying customers. It turned into this big thing and that was the product of a lot of learning and iteration and teamwork. I had mostly done smaller things in terms of my entrepreneurial career and then this, Contently, metastasized into something quite big. That kind of inspired me or nudged me to spend time digging into how to be a more innovative company and how to build and run a successful team. That ended up being what I ended up writing about in my books.
Holly: Awesome. Well, we love to talk about building high-growth products in high-growth companies. I think a lot of times the stories that I hear and the people that I talk to have something similar to yours where maybe there’s quite some time of smaller companies before one of them hits it, metastasized, as you said. I’d love to hear a little bit more about what that journey was like. You mentioned in there that you started as sort of a talent agency on the web for freelancers, but it became something much more, which includes tools for content marketing for large enterprises. How did that come to be? What were sort of the signals that you got from the market and how did you make that strategic decision to go in the direction that it went in?
Shane: A lot of what we did, our process was something like the scientific method where we had some hypotheses about how the world was changing and so we initially created the startup as a way… well, with the goal of testing these hypotheses to see if there was a business there. Basically, we repeated that process as we learned about what was happening. Essentially, in the beginning, our hypothesis was that there are more and more businesses that are trying to do content as a form of marketing. Instead of just paying for advertisements, some banner ads, writing a blog, creating YouTube videos to try and educate people on your company or your market or whatever, become thought leaders. Our hypothesis was that that was a growing field of the internet, a growing field of marketing. The other hypothesis was that businesses would have a hard time. If your business is selling a certain product, you’re probably not full of expertise and talent at telling stories and at running content.
Shane: Then, on the other side of that, a lot of my friends and colleagues were journalists and editors and video producers who were out looking for work, so our other hypothesis was, well, hey, if we can gather up some of these talented folks, then businesses might come to us and pay us money in order to access them, so that they can make content [inaudible 00:07:59]. There’s kind of three assumptions, three hypotheses there and in the first little bit, we validated that there are a lot of these people who are freelancers, and they are looking for work, and they’re willing to work with someone else and give a cut of the work if you get them work. Kind of like an agent would normally for, you know, like literary agent or something, and we validated that a lot of companies had a very hard time finding content talent and were willing to pay good money for it.
Shane: After we validated that, basically, the question was well what kind of business is there here? Initially, it really was just introduce people, editor and writer, here’s a client, client, here’s an editor and writer, our work is done. We’ll take 15% please. Initially, it was that and then what we found is that businesses need a lot more help than that if they’re doing content, especially if you’re selling soda, or you’re selling insurance or B2B software, you need more than just an introduction to a writer and an editor, you also want to know what you should be creating and where you should be putting it and if it’s working, if it’s driving results. Then, you might actually be a pretty big company, and you have a lot of people that want to create a lot of content, and they want to see what’s performed the best.
Shane: That, basically, led us to ask the question, well, if we build tools, you know, a kind of workflow for these other content marketing activities, will businesses pay for them and if they pay for them, what will it take for them to continue using these tools? It’s sort of what you would hear in a lean startup or am iterative product kind of conversation. That is the journey that we went down, but there’s kind of at any point, because it was sort of an emerging industry, there’s a lot of noise and a lot of hype and predictions. Not necessarily as much clear-cut demand or a lot of people don’t know what they’re doing in general in this industry because it’s an emerging one. There were a lot of leaps we had to take where it’s like we can’t really know if this hypothesis is true, so we’ve got to place a bet and try something and hope it doesn’t cost us too much money before we figure it out.
Holly: Do you have any stories of one of those that can help people, can help us sort of hear the color of what that was like?
Shane: Yeah. We started building analytics, for example, so there’s a lot of analytics software out there, but we said, “People who are doing content marketing, there’s specific metrics that they want to measure, and you can’t really get that with Google analytics.” We started building analytics and that is a big investment. It takes a lot of really smart people and it takes time. What we found is that for a lot of the stuff that we were trying to build, folks like Google Analytics were also just working on those kinds of things, too. Just because it didn’t exist, didn’t mean that we were going to build them faster than Google was, but we didn’t know what Google was up to.
Shane: Google ended up developing Google Analytics a little bit better and there were some things that we were working on that we never released because we were like, well, everyone can get Google for free, so we may as well integrate into Google Analytics, like send our data that we collect over there, so you can manage it in one place, or it will allow you to manage your marketing analytics from wherever you want and we’ll supply it.
Shane: Then, what we did find though is that there are certain types of analytics that no one had really been working on and in particular what we call document analytics, which is basically if you send someone a PDF or a slideshow, normally you send it over email. You never know, did they read it, did they send it to someone else, did they print it, what page did they get to? We ended up acquiring a little product that does that and that’s something that became part of our product suite that the data can also be sent to Googly Analytics, but no one was working on that. That ended up being a good investment, especially for in content marketing where a lot of people are making reports and salesperson sends a report and they want to know, did the person read it, what page did they get stuck on, all of that.
Shane: That’s an example that really sticks out to me of good investment and sort of failed investment, but we didn’t go down the wrong path for too long. Sort of knowing when to give up and just partner with someone else rather than keep building your product that’s the same as someone else. That was kind of the lesson that we learned basically.
Holly: Yeah, that’s a good lesson and one that a lot of us learn one way or another, but I think some people find… I’ve been in companies where it’s been really hard to make that case once we’ve invested in building something and then, a competitor or a Goliath like Google comes out and says, you realize that they’re building something like that, too. I’m curious if you have any stories around what the team dynamics and conversation were like around that and how you were able to quickly move on?
Shane: Yeah. In a startup, everything feels kind of like an emergency because you’re sort of on borrowed time a lot of times. Some of those were really hard decisions, and I think in looking back on it, a lot of the drama around these kinds of decision makes sense when you look at… when you do some perspective taking. You look at the point of view of the head of product, you look at the point of view of the engineers that were working on things, you look at the point of view of the CEO, you look at the point of view of the investors. You really think about like the personalities of these people and what they’ve been working on for so long, what they’ve been asked to do, sacrifice what they’ve made, and how all that can lead anyone to succumb to the sunk cost fallacy. Right? That while we’ve been working on this for so long, so we should continue working on it. I think it’s easy to, at the time, to sort of judge people like, well you’re not thinking clearly because it’s a sunk cost, it’s already in the past. We shouldn’t make our decisions based on that, but you put yourself in other people’s shoes, and you’re like, no, you want very badly for this to work because it’s taken so much time and effort. Some people have an easier time letting go of things than others.
Shane: That was kind of the main, in my recollection, the main hardship is just giving up and giving up on that sunk cost thing. I think the debate culture that we’ve had at the company has been really interesting because I think a lot of decisions that we made that were good and historically, that were hard decisions, but good decision to make, were the product of everyone feeling like they can speak up and debate, and they can express strong opinions and that their position is still safe inside the company. Also, that a lot of those debates were solved by experiments and by data, so it’s a more scientific process rather than whoever cares the most or who’s the most persuasive or whatever, wins, which is how a lot of debates in business get resolved. I think that culture has helped us. I’d say that in looking back, also, when we have had more challenges, it’s been because the debate culture has gone too far. When people want to be right so bad that they don’t consider all the information, or they don’t seek other information, or it gets personal because you’re debating so long, those kinds of things.
Shane: I wrote about this a lot in my book. Those kinds of things are so easy to happen, and I think it’s human nature. I don’t think it’s something you can really fault anyone for, but I’ve realized, as a leader, my role in many ways is to be the facilitator of great debates. Putting people with different perspectives together, getting them to really open up with their points of view, but also moderating and mediating the situation, so that it’s always about ideas, it’s not personal, we seek data, we’re all on the same team, you reward people for pushing the ball forward, not for being right. All those kinds of things have been a big lesson. I’m sort of rambling at this point based on your question, but that’s kind of how I see the unfolding of these things going better when that is how I see my job.
Holly: Yeah. No, I mean, I actually loved that, the things that you were saying there really themes that I’ve noticed as well and want to hear you talk more about. I think, so one of the things that really stood out to me and one of the reasons why I wanted to talk to you is because I’ve always felt that the best things I’ve worked on had the good fortune of being in a great environment. That great environment, I’ve come to learn that that great environment didn’t just happen, that people put effort in to making it that kind of place, so I kind of want to hear more. It sounds like you’re very focused on creating a place where people can feel safe to disagree and can look for truth together and can find facts over ego. Tell us a little more about that. How did… especially with a growing startup where, like you said, things can always feel like they’re all emergencies, how did you do that?
Shane: Yeah. It’s a big question and I would say that like anyone, any entrepreneur I think would tell you were I to go back, I would do a lot of things differently, but because of the way we did things, I learned a lot of things. It’s all valuable. I think that when the main principle that I think is sort of the animating principle of I think good products, good innovation, and good teamwork is understanding that a team is only going to be as smart as its smartest or most powerful person unless you do a certain set of things. You look at a lot of groundbreaking companies and products and you’ll see that they’re often led by some genius who calls all the shots. It may even be kind of abrasive, but it doesn’t matter because they’re so smart. Apple is an example that people use all the time. That works if the person in charge is really a genius and doesn’t make too many mistakes. Right?
Shane: I think in reality, most of the time, a team of people should be smarter than its smartest person and it should be smarter than its most powerful person, so you want to create an environment where that can actually be realized. When you start a company that you’re the founder, you have extra sway and extra power and all that and it’s easy to turn into kind of a hero complex. What we wanted to do from the beginning is kind of have this no cowboys’ policy. You’re not allowed to stay up all night saving the company by yourself and really, we wanted it to be the kind of place where we realize that we’re going to make the best decisions, we’re going to be smarter than any of us can be on our own if we work together in the right ways. Then, the question is, what’s the set of conditions required to do that? Then, how do you… In my book I use this analogy of like a zone of optimal tension. How do you cultivate an environment where there’s enough tension between viewpoints, between ideas, where you can… debate is the word I keep coming back to, you can debate, you cannot see everything eye-to-eye, while also not having things boil over?
Shane: The not having things boil over part, that’s where a lot of when people talk about building a culture, that’s where a lot of that comes in is creating rituals that are no matter how much of a rag tag group of soldiers we are, there’s some things that we do in common and those should be things that don’t step on anyone’s personal values or aren’t exclusionary in any way. The things like what we used to do every Friday, the whole company would go to lunch, and then, once the company was too big, it was every department would go to lunch. We’d order food and then, while we waited for the food, we’d go around the table and everyone would say one thing they’re excited about and one thing they’re worried about. It would start with the leaders and it could kind of be funny, you could talk about your personal life, you could talk about work, didn’t matter. We’d do this ritual every time and people opened up and they were vulnerable. It’s valuable for that, but it was also this tradition that we had that was like, this is our thing. It, like I said, it allowed you to be whoever you want, it didn’t exclude anyone, and it didn’t also sort of make anyone feel like they couldn’t be themselves because the whole point of it was to express yourself.
Shane: We created a lot of little rituals like that, things that we do every week, things that we do every time the whole company met, ways that kind of bonded us together, like family traditions. That makes you feel like you’re all on the same side, which makes it a little bit more safe to disagree on things because you have that camaraderie. We also, we were very deliberate and explicit in reinforcing that. What we don’t want is culture fit, we want culture add. We’re bringing you in, we’re hiring you because we want you to contribute something that we don’t already have and being really clear about that and celebrating that, rather than what a lot of companies think they need to do in order to have a good, unified team, which is getting people who have similar personalities and who get along real well because they have shared interests and all that. That actually, we decided is a distraction from what you really want, which is people who are going to contribute new things, new ways of thinking.
Shane: Then, another thing that we did to kind of reinforce this culture and those two ideas is our whole company is about helping people tell stories, you know businesses doing content, they’re being storytellers. Our writers and editors and video shooters are all telling stories, so we tried to create a culture where we share our stories. If you’re new to the company, you get up in front of everyone, you tell your story or you share something unique about yourself. We do this training to get people to present their work and their ideas in the forms of stories.
Shane: Doing that kind of helps knit the group together and makes it, once again, a little bit easier to have conflict without the conflict feeling personal because you have empathy for each other because you feel safe around each other because you know each other and you know someone’s story. When you do know someone story, it’s a lot harder to dehumanize them and treat them crappy. Then, you can have the debates without them turning into ways of trying to foil each other. It actually ends up being more about exploring options together. Those were the kinds of things that we did along the way.
Shane: Like I said, I do a lot of things differently now because we’ve learned along the way. In the beginning, we made some accidental good decisions and a lot of naïve decisions, but that’s the underlying ideas. The team has to be smarter than the boss.
Holly: That is fantastic. What are some of the things that you would do differently this time that you learned from, and why did what happen surprise you such that you would do it differently next time?
Shane: I think primarily it’s the reason we hired people. You’ll hear a lot of founders; you probably have heard a lot of founders and leaders of companies talk about how the hardest thing is people management and hiring people and firing people are some of the most difficult things you can do when you’re running a business. I think there’s a lot of the things that we did well in terms of the rituals and the inclusiveness and all of that, but I think in our choosiness of who we work with, in the early days I think we were a little bit misguided on what we thought of when we thought of diversity, and the reasons for hiring a group of people who are all different. I would just make some better decisions there. Like, it felt a little bit more like, oh, we have to do this, or we’ll get in trouble. We need to hire more women or we need to hire more people from different backgrounds because we don’t have that, because that’s bad, rather than framing it as we are missing some very crucial perspectives, so we’re going to not be a very innovative company before long if we keep hiring people who are all just like us.
Shane: Also, it’s not just about adding someone to the team who’s not like you. You have to take all of the little micro-opportunities to empower them. Otherwise, you’re just going to get people who feel uncomfortable or who don’t feel like they can speak up. Then, I think, actually starting out building our company with that in mind, we would have been a lot more careful of the early hires. Instead of hiring 20 people who were all kind of from the same sort of tech background, same educational background, making sure that the first person you hire, from then on, are all coming from the different types of backgrounds that will ultimately make this place kind of more cosmopolitan rather than trying to inject that later. I don’t know if that makes sense, but it’s basically like the earlier you start thinking about cognitive diversity and demographic diversity, the easier it is as you go along. That’s one half of it. The second half of it is it doesn’t matter if you have the most cosmopolitan gang of people in the world if they all have to think how the boss says they have to think or if people don’t feel like they can speak up because of all the little things that you’re doing or not doing, then you’re not going to get any benefit out of it and you’ll have people who feel like they would be more valuable somewhere else.
Holly: Yeah. I love that you brought in the terms cognitive diversity as well as demographic diversity. As you were talking about the beginning part, I was wondering if that was part of what you were getting at about I think I see anyway, sometimes teams who are in the early stages of trying to be aware of whether they are diverse and inclusive, overemphasizing demographic diversity, but not necessarily looking for cognitive diversity. I’m curious what those mean to you and is there a way you can tell when you’re doing it right? I mean, how do you even look for cognitive diversity? What does it mean to look for that?
Shane: Yeah. I like to use adjectives, attach adjectives whenever I use the word diversity just because it’s one of those words that immediately people think of it as a euphemism for… well, in America, it’s used as a euphemism for race or gender. It kind of can distract from the point, which is I think there’s really two things afoot in businesses if we’re just focusing on American business, but I think it’s sort of anywhere. There’s the pragmatic case for you want people who think differently because that’s how the group is going to be better than the smartest person in the group.
Shane: Then, there’s the sort of moral case in a place like America where you have historical injustice, and you want to give people an opportunity who haven’t had an opportunity because that makes the whole system better, and it’s the right thing to do. With those two things afoot, a lot of times, because of the way that the diversity is used as a euphemism for race and gender, is that’s all people focus on. Then, that leads to all sorts of weird kind of things happening, including the hiring of people who fit your category of diversity, but then not empowering them because you’re missing the point.
Shane: Really, what cognitive diversity is about is that what’s inside your head is what allows you to contribute the most to a group of people, and it’s what’s inside your head is the perspectives you bring, how you see the world, how you encode the world, if that’s different, that’s incredibly valuable. There’s a lot of science that backs up this idea. There’s actually mathematically proofs that show that people with different ways of encoding the world in their own heads, when you put them together, that increases the chance that that group of people will come up with creative solutions that no one could come up with. That’s really what it’s about and basically, your perspectives, your heuristics, the way that you see and predict the world, that all is driven by your life experiences. Your brain has formed in the ways that its formed because you learned things, because you’ve navigated the world, you’ve been educated, you’ve been through experiences and those experiences, all your experiences in your life are very much a function of who you are.
Shane: That’s where the things like race and gender and geographic backgrounds and your generation you grew up in and how many languages you speak, all those things very much do affect the life experiences you have, and the education you have, and the way you’ve learned to navigate and see the world, so that they’re all tied together. I think it is important to acknowledge that demographic diversity needs to be sought after because it’s going to bring with it the potential for different ways of thinking and what you want out of people with different ways of thinking, not just a representative from an identity group who then also gets put in this weird position of if they are ever wrong about anything, they’re representing their whole identity group. That actually leads to kind of not the same incentives for a team. You might hold back or you might fight for your ideas in different ways if it feels like really what you’re doing is representing a group rather than bringing different ways of thinking to the table if that makes sense. That’s where those things come together.
Shane: In terms of your question of how do you identify cognitive diversity, I think a lot of times when we’re auditioning people for a team, or we’re hiring people, we do this really dumb thing, which is we look at checklists of accomplishments, and we look at a resume, and we look at what people have done, and we try and find the people who have the top marks in whatever categories we decide. What isn’t on a resume and what’s not really buried in the “right answers” to a job interview is someone’s unique life journey that could lead them to see situations differently than the people you already have. I think in hiring or in just working with people in general, this is another place where storytelling is really interesting. If you get to know someone’s story, part of them, the interview process is asking people about questions that will lead them to hopefully share some of their story.
Shane: One of my favorites, for example, is what’s a time in your life when you changed your mind about something that was really hard? It’s pretty rare that someone answers that question in a way that doesn’t reveal a little bit about who they are and what they’ve been through. Another one that I really like is what’s something that you know how to do or that you know about that most people don’t and could you explain it to me and how you learned it. A lot of times people say, well, I know how to play cricket or whatever. That’s interesting. Well, how’d you learn that? Sometimes, it will be more exoteric than that, but I remember a guy I interviewed for a product job, and he used to be a piano tuner. That’s not something that necessarily will go on a resume, but it’s an interesting thing to know that hey, here’s someone who has training in a set of heuristics, and a set of life experiences that is pretty different than anyone here and maybe there’s something about being a piano tuner that could cause his brain to see and process things a little bit differently.
Shane: Getting at that I think is super fascinating, and it’s interesting anyway. It’s more entertaining than just reading resumes and asking the basic questions, but those are the kinds of things that I think are important because you really do want to work with people who can push you and who can help you see what you can’t see and vice versa. The other benefit of that is if that’s kind of how you’re auditioning process for joining a team is, people immediately walk in on day one after you’ve hired them knowing that you’re expecting them to bring what’s unique about them to the party. That just sets you off on a good path from the beginning.
Holly: Yeah. I really love that because it made me think. One of the things that really gets me fired up is the way that most people are hiring in startups today and that there’s so often… I’ll work with people who are looking for their next gig, and I’ll see the talent and the potential and the perspective that they bring to it and that they’re thinking in the right way, but they just face rejection after rejection because people are just looking for the list of accomplishments. If they haven’t had that chance yet, then they don’t have that accomplishment, and it just drives me crazy.
Shane: Yeah. I think that’s also why experience… I mean, there’s some chicken and egg there certainly in any job that you’re trying to get, but it’s experience in building, like we’re talking about products, experience in building products, developing products, working on products, those stories of what you’ve worked on to me are so much more valuable than where you went to school. I mean, I don’t really care what college you went to unless it’s the same college as everyone else on my team went to, in which case I do care because I don’t really want that, but I’d rather hear about the projects you’ve worked on, the problems you’ve solved, what you’ve learned from that, than I would about your GPA. I do think that that’s a pretty rare attitude to take.
Holly: Yeah. I think so, too, but at the end of the day, the questions that you’re asking is about their stories and what their stories tell about what they’re going to add to them team. I think you’ve built a great business, so can tell that something must be working here. Right?
Shane: Well, thanks. At every stage… One thing that’s interesting is every stage you kind of run into this thing of needing to reevaluate the status of your team. Right? Have we now been growing together in this ship for so long that we actually need some more perspectives? We’ve kind of converged on some similar ways of seeing this business and this industry and also, is the makeup of the team right now actually bringing out the best in each other?
Shane: That kind of reanalysis over and over again is something that’s important, but I’d say, when you say something must be going right, I laugh because you’re right when you zoom out and you look at it. When you’re zoomed in, and you’re focusing on the day to day market, for me it’s constantly this kind of like, uh, we could be doing better, oh, we need to reevaluate this, and I think that’s the process itself. It’s funny because that’s literally on my mind right now as some of the re-composition of the way that, you know, of who we’re including in our problem-solving process for the challenges we have now versus two years ago and eight years ago.
Holly: Yeah. Well, that constant rejiggering is a big part of being in a company that’s learning and growing and not just stagnant.
Shane: Mm-hmm (affirmative).
Holly: How many years old is the company now?
Shane: It’s about nine years old.
Holly: Wow, that’s solid, congratulations.
Shane: Yeah. It’s not going away, that’s an accomplishment.
Holly: Yeah. No, the company’s here, it’s real, it’s going, and how many people work at the company now?
Shane: I don’t know what the last count is. It’s somewhere between one and 200. I mean, so we have about a hundred in the New York office, but then we have offices in Minnesota, London, and California. I don’t actually know the last count because we also have, we have an enormous fleet of contract editors that are somewhere between freelance and full-time. I don’t know who counts. Then, we have this user base of about a hundred thousand creative people waiting for work. At any point in time, 10% of them or something like that, are actually working on this day, so there’s a lot of people in the whole org, but in terms of full-time, it’s in the hundreds. I’m not sure exactly.
Holly: Yeah. It’s important to mention when you’ve got the type of company like yours where you’re connecting workers who may be choosing to work less than full-time and then how you count it and all that. It gets complicated.
Shane: I am very proud of, if there’s anything I’m most proud of actually, it’s how many people we’ve been able to help put food on the table either as freelancers or employees. That feels so good in business to make something that not only people want to pay money for, but it actually pays for people to live their lives and to raise their families, that’s pretty awesome.
Holly: It sure is. Especially if, hopefully, you’ve got people who are drawn to working for… I don’t know if you call it working for Contently or working for the client, but working in your ecosystem because that’s the kind of work style and work life that they want. That, for me, is a huge passion as well as finding, you know, we don’t all have to be nine to five office workers.
Shane: Yeah. That was one of the, in the very early days, one of the theories that we had is that in the future, maybe even the future is now, finding the best person to contribute to your job or your team doesn’t need to mean that they live in your city or on your block or whatever. That’s pretty liberating, but also allows us potentially to do better work today than we could have yesterday because we can now access more people and that’s part of what we wanted to help companies do.
Holly: Yeah. That’s awesome. What are your other books, by the way? I know I’ve seen some of them, but are they of interest to people building products and companies?
Shane: My first book for sure I would say, it’s called Smartcuts and it’s about innovation. In particular, it’s about what psychologists call lateral thinking. It’s about approaching problems from different angles, and I kind of lay out basically the question of how do you think differently if, A, you don’t think different than you think, you think a certain way or how do you think differently given that you think a certain way and also given that everyone else is trying to figure out the new way to think differently, so that they can pass you up. That book was about basically ways to get yourself into seeing things differently and that kind of ended up being a good entrée to Dream Teams, which is about how a group can think differently together.
Shane: Yeah, Smartcuts is very much about innovation. I talk about different ways to grow a company or a career path. It’s kind of almost like a, it would be called growth hacking today. It’s sort of like what’s the mindset behind that and then also, how and when to use emerging technologies and emerging techniques versus best practices even when you’re working on something or when’s the optimal time to jump into something. It mostly just sort of frameworks for thinking about that, so it’s a little bit nerdier of a read than my latest, but for product people, I think it’s pretty useful, especially for anyone that’s kind of working on their own and not in as much of a team structure.
Holly: Do you have any sort of a quick glimpse of a technique someone can use to push their thinking to be different?
Shane: Sure. One of my favorite chapters is when I analyze this trend of radical simplicity and looking back to da Vinci and then Picasso and then Apple Computer. This company that I really like that’s still around called Embrace who’s started by this woman who sort of abandoned this really awesome career track in consulting to start making products for mothers of premature babies in the third world. Basically, like how do you keep a baby alive if you can’t even afford more than a dollar a day to live on if your baby is born premature or with terrible health problems? She started this company to basically help in these developing countries with neonatal care and basically, the challenge that they were faced with is make all of these things, like an incubator, to keep a baby alive if it’s born too early. How do you make an incubator 100 times cheaper than the current incubator that you can get in a hospital?
Shane: I explored stories like that and basically, the conclusion for… There’s a whole bunch of things that they learned that you can read about, but the conclusion is that one of the most interesting questions you can ask yourself as a product person or someone who’s looking at a process, a service process or whatever it might be, is what if we had to do this a hundred times cheaper or maybe make it more like 10 times cheaper, 50 times cheaper, but pick a number that’s so extreme that you can’t just make your current process or your current product more efficient. That you have to fundamentally reinvent the product or the process by boiling it down to first principles.
Shane: You have to kind of strip away everything but the essentials and actually reframe what is it that we’re trying to accomplish. In the case of the incubator, how do you make an incubator a hundred times cheaper than the incubator in a standard American hospital? It’s actually by deciding that the challenge is not to make an incubator, it’s to keep a baby 98 degrees for three months. Can you do that for a hundred times cheaper? That’s a lot of what the book ends up leading to is if you want sort of quick and dirty help in thinking differently, there’s certain questions you can ask yourself that force you to walk through a different scenario that you just can’t solve the problem by doing the same thing a little more efficient or by coming in on Sundays and working a little harder. That’s one of them that I really liked is what if you had to do this for a hundred times cheaper or 10 times cheaper.
Shane: The flip side of that is Google’s famous for its 10X thinking, saying what if we had to make it 10 times better? Actually, asking yourself that question, what if we had to make this as our product 10 times more profitable or 10 times more awesome, what would that mean? Actually, not just putting that out there as sort of an abstract hypothetical, but drilling into what would we have to do in order to make this happen? It requires you to project certain truths or assumptions or you have to say, well, we have to have an infinite amount of money in order to do this, but what if we did? Then, what would we do? Going through those scenarios where you strip away the different constraints that you currently have on your product can often lead you to ideas that maybe doesn’t make it a hundred times cheaper or 10 times better, but makes it significantly better because you’ve now reinvented something by reframing the problem. Those are the kinds of things that come out of that book.
Holly: Yeah. I had unknowingly used some of those in the past, so that’s, I’m sure, very helpful. I’d love to check out the other parts in the book as well. I always like to end by asking people if they have any particular advice for startup leaders, startup founders or product leaders. What is sort of the one message you would want them to take and start applying?
Shane: I mean, this goes in line with kind of what we’ve been talking about, but one of the things that I am really grateful for from my parents, one of the lessons that stuck with me my whole life and career is this idea that people are more important than stuff. The story that I like to tell is my mom was a wonderful person and a terrible driver. She was always backing the car into gas pumps and putting the van into a ditch and she was always wrecking the car. Like, these very sort of minor fender benders that scrape up the car, whatever, and I just remember ever time this happened, which was like once a year, my dad would always say the same thing to us kids, “First thing we do is to find out if Mom’s okay and if Mom’s okay, then we figure out the rest. It will be okay because people are more important than stuff.” I think in business it’s easy to fall into the, well, we’re running a business here, so business is business and sorry if there’s casualties.
Shane: I think that you can both run a business while having compassion and putting people first. Sometimes the hard decisions you need to make, sometimes you need to let people go, sometimes you need to tell people disappointing news, but I think always doing those sorts of things with that in mind, that people are more important. Making the hard decisions with compassion, making the hard decisions because there are other people whose jobs and lives are on the line that you have to make this hard decision for, but keeping in mind that sometimes it’s okay to make a little less profit if you take care of people and that I think that that will always come back around. That will pay itself back in the long run, just like growing up in a family that acts that way pays off in the long run in that you have really healthy relationships.
Shane: I think that’s the lesson and it very much applies to this idea of teamwork. People are more important than the product you’re building because people are going to build the next version of the product that you would never have thought of, so act accordingly.
Holly: Yes. Amen to that. If people want to find out more, how can they find you?
Shane: Just my name, All of my contact info and all my stuff is there.
Holly: All right. Great. Well, thank you so much, Shane. I’ve really enjoyed this conversation and I’m thrilled to talk to another “people are more important than stuff” believer.
Shane: Thank you. It was my pleasure.
Holly: The Product Science Podcast is brought to you by H2R Product Science. We teach startup founders and product leaders how to use the product science method to discover the strongest product opportunities and lay the foundations for high-growth products, teams, and businesses. Learn more at Enjoying this episode, don’t forget to subscribe, so you don’t miss next week’s episode. I also encourage you to visit us at to sign up for more information and resources from me and our guests. If you love the show, a rating and review would be greatly appreciated. Thank you.