How Contently CEO Pearl Collings grew to $53.8M revenue and 300 customers in 2024.

good morning everyone my guest today is shane snow he's an award-winning journalist celebrated entrepreneur and the best-selling author of smart cuts he's also author of the forthcoming book dream teams as well as the co-author of the storytelling edge he co-founded the content technology company contently which helps creative people and companies tell great stories together and serves on the board of the contently foundation for investigative journalism shane are you ready to take us to the top i am ready so you know this about me most authors i you know say no to because they just want to promote a book and it's frankly very boring and i just eat them alive but you i made an exception for because you come from a sas background you come with a software background so tell us quickly about contently and then i'm gonna go why on earth do you decide to write a book this is like the most difficult thing ever instead of doing contently so contently didn't start as a sas platform it started as a marketplace kind of a newfangled talent agency to help you know laid off journalists from the new york times connect with clients turns out that the most profitable clients the most interesting clients when we launched about eight years ago ended up being brands wanting to do content marketing which was starting to become this popular thing and so as we leaned into that we by necessity had to start building project management tools to help these brands who are connecting with our marketplace and then that became the business it turned into this full-blown sort of like sales force for content marketing uh for for managing everything about your content uh program and that's turned into sort of the content operating platform that helps companies not just with content for marketing but for hr and a whole bunch of other things so that's the very quick sort of back story but we we actually had a point where we were going to have the the software portion be free and be subsidized by the uh the marketplace and we got in this big argument and and the argument was solved by uh my partners and i was deciding to do a test to start selling some features of uh of the project management tool uh for a monthly fee of a thousand dollars and when we sold 13 in the first month we said okay uh this is the the business and and here we are well what do people get for a thousand bucks a month was it like a number of words or number of articles or what uh back then when we started it was uh it was sort of workflow so you want your pr people and your lawyers to weigh in on your content you're about to publish now there's a there's a you know packages and tiers but it's everything from analytics document analytics sort of more hardcore workflow integrations and everything you could think of sales and environment tools um so it's kind of everything you'd want to do to uh to organize content in a big enterprise um so yeah depending on the size of your enterprise number of seats it very much kind of mimics that standard uh kind of marketing automation type of sas product only it's content rather than than uh email and would you say you're still kind of enterprise folk like what's the average customer pay per month is it a couple thousand uh six to ten thousand oh yeah so very much enterprise space high volume yeah yeah and that'll change at some point but that's where we are now okay good and before we move on to the book can you give me a general sense of scale so i know you raised capital how much have you raised and can you generally share team size things like that yeah uh so we've uh the company's about eight years old we've raised uh 20 million dollars in total which is about a quarter of any of our competitors um which is great for us because we're you know similar size and and have an outsized present and presence in our own content marketing staff is about 100 people um and um yeah what else did you ask how many customers how many customers are you working with now uh we have a couple hundred uh enterprise customers we have uh one group like i alluded to that will change at some point we have a group of customers that we call high-growth uh customers so smaller companies that are paying a lower average and uh i forget what the number is but that's that's a big growing category for us as well okay surprise and nor north or south of 20 million in arr uh it's about at 20 million look at that man i'm on fire this morning good guess okay so you're sitting on this rocket ship you're eight years in started as a marketplace you shift the model you're now serving 300 enterprise customers paying calls six grand a month call it 20 million ar right now why take time out of your schedule to write a book uh so a couple of reasons you know one is i think of my identity as a journalist i'm a journalist who ended up starting this company with a couple of partners i wrote about business and technology and science and so you know i i was covering companies like mine is now um and uh and so when we started this company it's in you know the field of media and content which is my industry uh so it's a natural thing to sort of fall into but as we started growing the company i realized that i had deficits in terms of uh you know how to build an innovative company and so my first book i wrote basically i interviewed people and i took a tour of history and psychology to try and understand how breakthroughs happen how innovation happens and find patterns for how we can do that so the writing the book was an outgrowth of my journalism work that was an excuse to help our company get better the second book that i co-authored is about our industry it's about using storytelling to build relationships and build companies um and this new book dream teams sort of a similar thing um it's sort of this itch that i've had for a long time as my role went from being the guy who did stuff right every founder you know ends up you know you you paint the walls and you take out the garbage and you write the code and you do everything uh my role went from that to the guy who picks people to work together and then has to help them work together better and seeing as the team grew you know things slow down as as organizations get bigger it's sort of natural people start having problems with each other and casting the right group of people to work on problems becomes really important and realizing that i can't make every decision myself i have to empower people with information to make decisions so i've became sort of obsessed with this as a new role that i have that i suck at so similarly let me take a tour of history and uh and the other thing too is part of what i was looking at is just the way the world and our society is sort of changing now because of technology communication and you know just politics is getting very strange i was concerned with the idea that we need each other to do anything great to make progress and yet we prevent progress because of each other and so i kind of wanted to take a meta look at you know human collaboration and the dynamics that help a team in business exceed the sum of their parts or slow down or destroy itself and how that same thing plays out psychologically in society and politics in art and entertainment all those sorts of things so that became the the genesis for the the book um part of what happened also i've been doing research i've been interviewing uh people and doing my sort of obsessive weekend and night thing um but i realized that i was not the right person to take our company from you know the 15 million to 100 million you have shane you have co-founders all right how many co-founders i do i have two co-founders yeah once the business guy once the tech guy i was the marketing guy um and then content guy so i realized that i was not the cmo that was going to take our company to the next step function so i hired a replacement and uh and after a month of getting her up to speed i wanted people to stop going around me um and and really for the mantle to fall on her and so i took a two-month sabbatical to kind of write for 14 hours a day and and finish this book so i i took some time off to step back and do this and then came back and and kind of became the consultant to her organization rather than the boss and so that's how i managed to do both these things well coming up we'll talk about why chrysler failed while wu tang succeeded and some other surprising factors behind mergers marriages and partnerships well also i'll talk to you i know you talk about the wright brothers a lot and what their daily arguments can teach about group problem solving so shane we'll talk about both those things but real quick just since facebook's hot right now in the news you've got sheryl sandberg to do your afterward tell us how you got her to agree to that and and why she liked the book um so i helped out cheryl and adam grant with their book launch option b which is the book that was kind of inspired by the you know the tragic untimely death of her husband um and they wrote about uh resilience and getting through hard things and and they reached out to me asking if cause i'm a linkedin influencer if i could write about a time when i had to be resilient to get through something and and promote their book through that so i wrote probably the most difficult blog post of my life about uh and you can find it pretty easily um it's uh called how i got through the worst days of my life and uh and i wrote this post and it went kind of inadvertently viral a few million people read it and so then cheryl emailed me and kind of with this uh this email oh my god uh thank you for sharing your story thank you for helping us with our lunch raising awareness for this important thing um if i can ever do the same for you let me know so i said did you write the afterward for my book about your philosophy on teamwork collaboration working together without falling apart and so she actually pulled adam in as a co-author of her book and uh and we then pulled in uh a dozen artists from around the world to illustrate uh cartoons with some of the salient quotes so the afterword of the book is uh it's kind of unique but it's a collaboration sort of a again a meta meta study and people working together but she is one of the more generous executives of huge gnarly companies that i've run into and uh and i was i was surprised and pleased by that that's great all right let's let's dive into some of the hard content in the book so give you talk about i know you talk with the wright brothers in the book tell us more about again why their arguments each day can can serve as an interesting lens for us to look at group problem solving through yeah so i love this story of these guys they're two brothers and it kind of reminds me of me and my brother i have a brother who's a year and a half younger than me couldn't be more different and we hated each other growing up and also were really good at building forts together and uh you know those things that brothers do uh so they recognized that if they were going to invent the things that they wanted to invent if they were going to solve big problems they had to have this sort of war of ideas they also recognized that they couldn't let their egos become too attached to any certain way of thinking about a problem um so what happens when we have a very strong opinion on something when we're debating you know which is a i think an important part of problem solving and innovation uh it often we reach a point where the conflict either sort of threatens to destroy the relationship or threatens to get too personal where we're no longer you know talking about ideas so they had this really clever thing that they did to kind of in the book i talk about this ideal zone of of cognitive friction so what they would do is they would be working on a problem such as you know how to propel this flying machine forward and they'd start these arguments and they'd purposely get really intense and really hot and to the point that the neighbors would sort of worry about the yelling they'd hear out the windows and uh and they'd scream and they'd argue and they'd fight and then they'd stop for lunch and they'd eat their sandwiches and then they'd go back to fighting but what their rule was is whatever side that wilbur had took in the morning he had to take the other side in the afternoon and vice versa so when they got to the point where they were going to kill each other they had to switch sides and this forced them to do a couple things that i think are really important force them to de-personalize the uh the argument so you know you want to win the argument it's no longer about winning for your sake it's about winning the idea's sake and also force them to put themselves in different perspectives which it turns out is how we can can become smarter than uh than the smartest person in our group is by combining different perspectives and heuristics and different things in our mental toolkits so kind of force them to take these sides and do this and uh my favorite sort of meta lesson from this that you probably uh read in the book is with the propeller argument in particular um they actually so everyone knows if you haven't connected the dots right brothers we're talking you know plain guys yes the airplane yeah uh they're trying to figure out how do you propel this plane forward and the result of these debates and arguments where they had to keep switching sides was they realized they needed two propellers and they had to spin in opposite directions um in order to keep the plane from spinning spinning on a sail and uh and that actually is sort of the perfect analogy for kinds of groups that can solve problems in very clever ways is that you need to combine disparate uh ways of approaching things and uh anyway so i they did a whole bunch of other stuff but i i love that they had these hacks for forcing themselves to uh to look at things in ways that that their competitors uh weren't looking at things one more example quickly here so mergers acquisitions a lot of my listeners are either buying companies selling companies their private equity firms rolling them up they know they build a pro forma for an acquisition and you know zero percent times does it actually pan out exactly as you model the pro forma so what did you learn as you studied chrysler and wu-tang in terms of why sometimes mergers acquisitions and two groups coming together work versus don't uh so the sad math is that most mergers and acquisitions don't achieve what's called synergy which is they don't add up to more than the value of the two companies beforehand so most acquisitions just don't result in any net gain in fact a huge number of acquisitions actually result in a loss which really sucks because they're a lot of work and uh you know obviously and companies merge so that they can combine the different things they have and become better which you know in theory is what we want to do and so in the book i write about uh two kind of contrasting case studies one is the worst acquisition of all time which is daimler and chrysler two massive auto companies that come together and after a few years they're worth less than any either of them had been worth before jane i have to challenge you there why did you not choose time warner and aol uh you know it's was it close it was close but it's not as bad okay um and and i think also the uh the reason for it was a little more uh it was a little more out in plain sight with daimler and chrysler than any old time warner um so what happened with it and then i contrast this with the wu-tang clan which is a smaller merger um nine kind of alpha males from the projects in staten island that came together to become the greatest rap group of all time and change music history um and uh and they had a lot of very obvious conflict at first they came together and they actually brought guns to the recording studio you know they came from different gangs they did not like each other um and they were very suspicious of each other um and and they went on to become this uh this amazing transformative uh group and uh and daimler chrysler had everything on paper for them for this merger they they had you know sort of complementing skill sets and uh but they also the the thing that people chalked up their failure to is what most mergers get shot most mergers get chalked up to which is cultural conflict um so they did all this stuff they're like there's the germans and there's the americans they have different values and different ideas and you know different etiquette so we're gonna do these you know sensitivity trainings on german dining etiquette and sexual harassment in the american workplace so we can get them to play nice and they were so timid about making sure that that you know they didn't destroy each other um that actually would happen is what when you dig deep what normally kills most mergers and most synergy emergers is they uh they didn't they actually they had what was called organizational silence they did not actually press together uh well enough they didn't you know rub their different ideas and and they didn't have that friction that actually makes for for new ideas coming out of different people so they actually stayed away from each other two ceos would go weeks without talking to each other they tried they didn't want the germans to fight with the americans so they just kept them separate and this made everything get sort of demoralized and fall apart um this is a really quick version of kind of the the lesson learned from this but you look at mergers in you know in business history and this is the thing that actually leads to mergers not doing well is people are scared of conflict so they don't speak up they don't argue they they don't combine things and emerges that do go really well are the ones where they actually make people move and and live in different offices and they host the arguments and they host the debates and they moderate these things and they let people fight and they let people quit rather than because of fighting rather than quit because they're getting ignored and with the wu-tang clan what happened is the whole point was uh the rizza who's sort of the the captain of the gang he would make the beats and you had to show up to the recording studio and battle one of the other guys and whoever had the best uh uh the best rhymes for this particular beat would win and you get to go on the record and so he'd host these battles he sort of channeled their energy away from you know wanting to you know be suspicious of each other and kill each other into uh coming back every week with newer and better material to try and beat each other and when you look at the history of innovation in music and hip-hop generally but in all sorts of fields it's uh it happens when you you don't let competition or fear of you know your different your differences uh cause you to go and go silent or you know murder each other it's when you manage to keep it in this ideal place where it's actually elevating the game itself um and so you look at research even in you know marriages uh the surefire sign that a marriage is going to fail is not arguments it's not fighting uh it's when you stop talking to each other yep communication it's so key in both those examples you gave shane listen hey we're running out of time here but um i want to ask you real quick before we wrap up with the famous five where can people grab the book if they want to get it shanesnow.com has everything of mine or it's just called dream teams you can find it there guys there you have it shane let's wrap up with the famous five number one besides any of your own what's your favorite business book my favorite business book besides any of my own um you know i always since it came out i really liked adam grant's give and take because it was i'm sure it's been mentioned a lot here but it's a fresh perspective on what it means to get ahead that you know the people at the top and the bottom of any field are the most generous and you know how can uh the most generous succeed and and not succeed and i think there's something really important to that message that we do our best work when we help each other out um and when we're generous and and that that's important and sort of being takers and trying to get ahead by stepping on other people is sort of short-sighted and then there's also the kind of the other side of it being generous with only the short term in mind is uh going to get you stepped on but being generous with the big picture in mind i think is how uh how we get ahead ourselves and together all right quick quick answer on this one number two is there a ceo you're following or studying right now ceo i'm following uh catherine minshew i think is one of my favorite ceos she's ceo of the muse yeah good one number three is there a favorite online tool you have uh that you like that you use a lot for building the company uh sumo oh yep sumo number number four shane how many hours of sleep to get every night five to six okay that's pretty good and what's your situation married single you have kiddos uh i am single single no kiddos no kids i actually was married at one point but i am single again all right and how old are you i'm 33. all right last question shane what do you wish your 20 year old self knew uh i wish my 21 now i wish my 20 year old self was more confident uh you know i i didn't do a lot of things just because i was scared that i couldn't do it and turns out that i could do it so so i would go back and tell 20 year old shane stop worrying and just be confident guys there have it from shane we're the co-founders of contently founded back about eight years ago they've scaled now to uh over a hundred folks on their team 300 customers enterprise customers that pay about six grand a month so caught around 20 million bucks an ar today growing rapidly 20 million raised he decided he wasn't the guy to take the company in the cmo role to the next level so he took a sabbatical two months went off and wrote this book called dream teams the importance of really embracing competitive stuff inside of these teams let the best idea win take the other perspectives view after lunch so you can really get in their shoes and ultimately that's what leads to the best ideas go grab it dream team shane snow thank you for taking us to the top thank you