Episode #49 – The Performance Marketing Spotlight with Sean Ryan

Marshall Nyman [00:00:02]:
Hello and welcome to the Performance Marketing Spotlight. I’m your host, Marshall Nyman, founder and CEO of Naimon Co. Each episode I will be bringing you someone with deep experience in the performance marketing space where they share their career journey and insights about the industry. Today I have Sean Ryan from Rotary Digital. Welcome to the podcast.

Sean Ryan [00:00:21]:
Nice to be here, Marshall.

Marshall Nyman [00:00:23]:
Of course. Excited to have you on today. And let’s jump right into it. Can you briefly introduce yourself to the audience?

Sean Ryan [00:00:28]:
Yeah. Like you mentioned, I own Rotary Digital. I’m a lifelong ad salesman. I often joke that I think my goal in life is to one day be a full time artist that eats at Whole Foods. So I’m sort of slowly getting myself there. Currently, I spend my time running this newsletter company, which we’ll talk a lot more in detail. And other than that, I paint on the side. I’ve got three kids and I’m currently sitting here in Ithaca, New York, of all places.

Sean Ryan [00:00:57]:
I’m from Philly and I’m sitting in Ithaca so that I can be here for my son’s final season of soccer.

Marshall Nyman [00:01:03]:
Amazing. Yeah, sounds like a lot of fun stuff.

Sean Ryan [00:01:06]:
Yep.

Marshall Nyman [00:01:06]:
How’d you get your start in marketing, man?

Sean Ryan [00:01:08]:
I. Well, I mean, I’ve been a lifelong ad salesman. I was, we, I know we talked about this before we started, but things have changed so much. But I. I came out of college and I was essentially, I was teaching tennis full time. And then I didn’t want to have to do that for my next 20, 25 years because I knew my body would break down. So I got introduced to media sales and started working for a local magazine in Philadelphia called 7 Arts. Of all things, it was a local arts magazine.

Sean Ryan [00:01:35]:
And then through a combination of things, I was lucky enough to land my first job in New York at Ladies Home Journal, one of the five, or one of the seven sisters, as they used to say. Biggest magazines in the women’s space used to be that back then, out of those seven magazines, they reached one in every three women across the country. So, yeah, that’s where I started. And things have changed a tremendous amount since then. But it’s kind of interesting that as much as things have changed, a lot has stayed the same.

Marshall Nyman [00:02:00]:
So tell us a bit about your career journey before you ended up starting Rotary.

Sean Ryan [00:02:03]:
Yeah, like I said, I was in sales. I started in print sales. You know, I started before we were doing anything like this, where you were typing out letters and mailing them off to people to get them to be interested in what you were selling. We God, for years you know, the big thing for us was face to face meetings you had to have. I worked for so many places where you were required to have 15 face to face meetings with agencies or brands every week. That was, that was, that was all you did. And so you spent most of your time on the phone and pounding the pavement just trying to get sales calls and you know, knocking on agency doors and sitting in agency lobbies and you know, just doing anything you could to get these face to face meetings to move your business. So that’s really obviously changed a lot.

Sean Ryan [00:02:47]:
It’s still amazingly, one of the most valuable things we can do now is face to face meetings. It’s just become increasingly harder as you know, Marshall probably as well as I do and, but it’s still something that we, I, I strive to do. I strive to, to do that as much as I can. So yeah, through that worked in print and then my first job in digital ad sales came with People magazine. Used to be back in the day that when you wanted to read any of the timing publications online, you had to go through AOL behind the AOL paywall back in the dial up days. And so we were one of the first magazines at Time Inc. To decide to bring the website outside of the AOL paywall and make it its own direct website that complemented the magazine. So I was probably salesperson number one for people.com when it became a Time Inc.

Sean Ryan [00:03:37]:
Property. And so I learned literally what an impression was at that point. I learned what a display ad unit was and that was an amazing experience for me. And then basically through that I worked through a variety of digital shops along the way. And then it one point I basically decided to become a consultant so that I could not be on the train every day to New York like I was for the past 18 years. And I decided to become a gun for hire where People would basically hire me commission only as a seller. And then I worked for a ton of companies through there. That led me to Cool Material, which was a men’s site based in Philadelphia.

Sean Ryan [00:04:12]:
I started working with that owner and I know we’ll talk about this a bit later, but you know, that was really sort of the jumping off point for starting Rotary and getting into the newsletter business.

Marshall Nyman [00:04:20]:
So what, what else led you to start Rotary? What was the onus behind it?

Sean Ryan [00:04:24]:
So while I was consultant and I was mentioning that I was like 100% only commission seller, cool Material was this great site, you know, years before that for me to generate any business, I had to call on agencies and respond to RFPs. And mind you, like, when I won a piece of business, it would be for, you know, three, four, $500,000. It was great, but it’s a really hard process. You were battling with tons of other publishers and a lot of the times you put together these incredible programs for brands and no offense to the brands, but after they were done, it wasn’t that they would automatically come back to work with you again. So you would do all that work for months and then ultimately, ultimately the next time it came around, they wouldn’t work with you. So the process of RFPs was really difficult. When I started working for cool material, I really started. I just sort of took them on in the side.

Sean Ryan [00:05:08]:
And what was so great about it is that it went back to come when I started where I would get on the phone with brands and I would be like, okay, we have an ad for 2000 hours, we’ll drive a thousand clicks for you. And they would just say yes. I was able in the beginning to have 20. I would re. I would reach out to 20, 25 clients a day and I was closing one or two deals a day and they were only for 1,000 to $2,000. But it was so great. It was very, very tangible, right? You spend this much money, I generate this many clicks for you. And it became this like really fun way to work with brands.

Sean Ryan [00:05:35]:
Not to mention that cool material was really geared towards someone like me, kind of an affluent guy that, you know, with all the gadgets and fun stuff. So I was calling on great brands and what happened was they only had two ad units. So fourth quarter would come and right around this time, I think it was the same time you started your company, Marshall. It’s like 2016 where direct to consumer companies were huge. There were so many of them and they all wanted to run during the fourth quarter. And what happened was I only had two ad units, so I was telling everybody no. And I was like, well, this sucks. I’m a commission only seller and I don’t have anywhere to run these guys.

Sean Ryan [00:06:05]:
So I started talking to some brands and I asked them where else they ran. And I think the brand that I talked to at that time, believe it or not, was Dollar Shave Club. And I talked to somebody there and they said, well, sometimes we use newsletters. And I was like, email newsletters? I was like, does anybody really read them or, you know, buy those? Because when I worked at People in Rolling Stone and all the stops I had along the way, we would sell these huge packages and we would just give them the newsletters for free. So it wasn’t even, it didn’t even occur to me that that could be a valuable vehicle. But we were like, okay. And so my, the founder of Cool Material, who’s my current partner, Tim, he and I decided, all right, we’re going to launch a newsletter that targeted basically the same kind of guy that read Cool Material. And the idea was, well, why don’t we go out and find content that we like on the Internet and we’ll just assume a few hundred thousand other guys would like the same thing.

Sean Ryan [00:06:48]:
So we just went on the web and found interesting stories, nothing related to politics and nothing negative. And we just put together this good looking email. And this is funny, but really how the company. And so that’s how we started it. And the big driver at the time was there was a platform that’s still around today called Dojo. And what it was was a sweepstakes platform. I see you nodding your head, Marshall. And so basically we would work with all of these publishers and we would say, we would all get together, you know, I would work with GQ and Esquire and all these different big brands and we would say, okay, everybody has to commit to driving 5,000 entries to a sweepstakes where someone could win an Apple iPhone.

Sean Ryan [00:07:23]:
And we would be six or seven of us, and we would all drive 5,000 entries and we would all get 35,000 emails at the end. And the assumption was that you would not keep them. Right? You think those 35,000 people only wanted to be there to win the phone. But we found that 60 to 70% of them stayed on to get elevator. And it became this like huge driver for us. I mean, from, from that point for the next few years, we use that to instantly drive elevator to like a 400, 500,000 subscriber business. And we did it for our next email called Shift and we even did it for our email blazer. And so that was a huge, huge reason that we were able to start back then and succeed.

Sean Ryan [00:08:00]:
And I think that would be really difficult today. But that’s why I started it. It was a way for me to have another sor performance based ad unit for brands and give them a, a very measurable way to sort of, you know, measure success. Right. So again, anytime they ran with us, we charged them a flat rate, we got estimated clicks for them, and then we were able to figure out pretty much even on our end that if any of them got something better than a $2 cost per click value, they would run with us again. And it was just a much simpler, easier way to, to work with brands at that time. And it became really fun. Right.

Sean Ryan [00:08:29]:
I, I started a company with a great guy, Tim, and we basically built it around the idea that we would just find stuff on the Internet we liked and we assumed other people would.

Marshall Nyman [00:08:36]:
Too, tell us a bit more about Rotary and what the core business is.

Sean Ryan [00:08:39]:
So the core business is, you know, building a very vibrant community of about one and a half million affluent men. We were very intentional when we started it that we wanted it to be very specific to men. No offense to anybody else, but we knew that the more targeted it was, the easier it was for us to get interest from brands. And you know, to be honest, you know, that’s how cool material was. Cool material was for affluent men. And I just always thought that we could be a niche business for, for, for affluent men. And I always thought that if the business was more broader, if it was men and women, that it became more of a scale play and we couldn’t be a scale play. And there were a thousand other ways to buy scale across men and women.

Sean Ryan [00:09:15]:
So we just really hyper focused in on affluent men. And the idea was to create a very engaging newsletter that would be a. We always say it’s kind of a welcome reprieve for your inbox. You get all kinds of emails in your inbox that you don’t like. This is the thing that you looked forward to getting every day. And the idea was simple. We would run a single ad unit in each of the newsletters. We have four of them now.

Sean Ryan [00:09:34]:
We would give you 100% share voice and we would, we would create the ad for you and we would basically forecast how many clicks you get and you would be able to tell us on your end how those converted. So it’s a very simple business, which is great when brands are happy. I will say that when brands can’t figure out how performance is doing, we don’t really have much insight into that. So that makes it a little challenging when things aren’t going well. But you know, 80% of our brands have been running with us, a lot of them from the very beginning. So, you know, we’ve continued to have a really long sort of strong history with a lot of great brands and it continues that way now. So yeah, that was why we started it. And it’s been just really, really fun.

Sean Ryan [00:10:09]:
It’s changed a lot over the last seven, eight years, but it’s really been the same. We’ve just really been hyper focused on Creating a really vibrant community of guys that would be really valuable for brands in whatever form that is.

Marshall Nyman [00:10:18]:
Why are newsletters so important?

Sean Ryan [00:10:20]:
Well, you know, I’m a homer, right, as they say when it talks about newsletters. But it’s because it’s a direct relationship with a reader. It’s a lean in experience, right. You know, when you’re on a website and you’re being given, you know, display ad units and pop ups and even, even pre roll and videos, it’s, it’s a, you know, something that you haven’t basically, you know, subscribed to. And so for a newsletter like you’ve made a decision to subscribe to, to not only a, an experience but a community. And so by doing that you, you are more of a lean in valuable user. And as a result of that, you know, if you are around long enough, you tend to become someone that’s very lo community and everything that that newsletter offers. So you know, we take a lot of great pride in working with some really talented editors to create a really strong community for, for all of our readers so that they feel like they’re in the know on something.

Sean Ryan [00:11:10]:
And so when we bring them articles they assume, hey, if that article is brought to us by Rotary, then it must be good. And they feel the same way about brands. If we recommend a brand to them, the assumption is, well, if Rotary was willing to share it with us, it’s got to be a good brand. And so it makes that reader extremely valuable for any brand because it’s someone that’s really opted in and has, you know, is willing to sort of engage with anything that we offer them and.

Marshall Nyman [00:11:33]:
Helps brands move away from the reliance on Google. You recently stared the shades at Affiliate Summit Ease with our senior director Michelle. The session was titled Swapping Search to Subscribers. Tell us a little bit about that session.

Sean Ryan [00:11:45]:
That was a great panel. Michelle did a great job by the way. She was awesome. And really the idea was to really help marketers understand the value of email and subscribers in the age of as we’re seeing what’s going on with search, right? Search is really going through a huge change right now. It’s not a great source for brands. It only is going to get worse with the, you know, basically you know, where AI sits and where Google has basically a AI generated answer at the top of their search related pages. So it’s really making it very difficult for publishers and marketers to leverage search for success. So we really were there to sort of help them understand the value of the newslet and A lot of what we, I said to you earlier is really true for them.

Sean Ryan [00:12:31]:
This idea that we have a very engaged direct community that you can access and that your brand will be seen in a very positive light because we’re recommending it. So we spent a lot of time talking about that. And the second thing we talked about, which I shared with you a little earlier, is getting brands to understand that newsletters don’t necessarily have to be the end of the funnel. Right. Most brands come to us understandably, and they say, okay, I’m spending X amount of dollars with you and then I expect to see X amount of return on that single ad unit that runs for that day. And what we’re trying to work with them and help them understand is that we can be a very valuable solution for them earlier in the funnel. The idea that if I have a newsletter that drives 2,000 visitors to your site, it’s not necessarily just about the sales, which I know are important, but it’s a way for you to retarget 2,000 people that have made a decision to find out more about your brand and again, likely will give a much more positive view of your brand because it was recommended by us. So, so we spend a lot of time talking about reframing newsletters, not as just an end of stage solution, which they are, but they can be an earlier stage solution for you in terms of remarketing efforts and targeting these people to basically convert later in the in the process.

Marshall Nyman [00:13:37]:
Any upcoming conferences you’re planning on attending?

Sean Ryan [00:13:39]:
Yeah, I’m going to attend. Affiliate Summit east was so great. I got to meet so many unbelievable people and it was a really welcome community. I mean, understandably. Right. I’m coming in as a kind of a paid placement, which is not necessarily the norm. It’s something like that. But people were really, really interested in engaging with me and learning.

Sean Ryan [00:13:55]:
So I’m going to go to Affiliate Summit West. I’m very excited about that. The second one, I just got back from something called Beanstalk, which was a commerce event. It allowed me to meet some tremendous people in the, in the brand and e commerce space and just really build some great relationships in Brooklyn. And then the last one is there’s an Amazon event in October in New York that I think I’m going to go to. And that event will give me an opportunity to hopefully have similar conversations with brands that only work on Amazon in the same way that I was trying to engage with brands that only worked in the affiliate space and just sort of educate them on the value that we can bring to help drive sales on Amazon, which is something that’s become easier to do now than before. So those are the big ones, probably that Amazon one and definitely affiliate Summit West. I’m really looking forward to that.

Marshall Nyman [00:14:37]:
What excites you most about performance marketing right now?

Sean Ryan [00:14:40]:
I just think it’s become, it just, you know, as more and more confusion goes into the, in our space and trying to understand where value is, like it’s very easy to understand our value, right? It’s very easy to understand that when you market or, you know, when you advertise with us, you know, we can show very tangible results. You know, those may not be exactly the ones you need, but we can prove that our ads are working. We can prove that we’re driving specific users to your, your landing pages or your product or your solution. And I just think that that’s something that’s never going to lose its importance. And so for us, you know, our big focus is we spent a lot of time thinking that we would be more valuable at scale and now we realize we’re more valuable just creating more ways to make the current community of one readers we have even more valuable. So you’ll see a lot of new things that we’re doing in the newsletters where we’re collecting first party data almost on a daily basis. Just really interesting things that we’re learning about our readers that can be valuable to marketers. We ask them questions not only so, so we’re not only asking them to read articles we recommend, but we’re asking questions.

Sean Ryan [00:15:42]:
We’re asking them to give us information about themselves and, and, and again, just giving them experiences that feel really unique to each of our newsletters and makes them more loyal and makes them more loyal for, you know, brands as well.

Marshall Nyman [00:15:53]:
How do you see AI affecting the newsletter space?

Sean Ryan [00:15:56]:
AI is killing the newsletter space. I would rather see attrition kill the newsletter space, to be honest. But that’s a separate conversation. AI makes it really easy for newsletters to launch. But you know, we’re someone that as a company really, really focuses and zeroes in on the fact that we’re very much a human company. The things that we provide you are human curated. The ads that we create for you are human developed. The, the experiences that we give our readers are from humans.

Sean Ryan [00:16:25]:
And so for us, I understand that it makes it very easy right now to spin up a newsletter. I’m not sure that it’s so easy in our space, like the consumer affluent men’s space, to spin up a newsletter to the scale that we can or that we have today, it’s way harder. But for us, AI is a huge disruptor. I mean, we use AI in certain elements for what we do, you know, gathering information or research. But at the end of the day, as AI becomes more, you know, ubiquitous and, and relevant, you know, we’re really trying to lean into the idea that when you sign up for one of our newsletters, it’s a very sort of one to one human curated experience and hopefully that’s something that we can continue to do moving forward. But, but to answer your question, AI is, is allowing people to just spin up newsletters at an alarmingly fast rate. And at the end of the day it will be up to the market to sort of how many are too many? And it’ll be up to, you know, it’s basically up to the marketers themselves to decide that there’s too many as well. So I think at some point there’s going to be attrition.

Sean Ryan [00:17:29]:
There kind of has to be. I also think the last thing not to go too overboard on this question is that, you know, this ability to sort of spin up and leverage AI is great, but it’s also increased, I think a lot of, you know, not great partners and not, you know, funny ways of growing audience and funny ways of getting emails and funny ways of getting people to sign up for your newsletters. And I think that that’s going to kind of rear its ugly head at some point where you’re going to soon find out that there’s a lot of fraud in the space. And so hopefully that’s something that will be cleaned up as well.

Marshall Nyman [00:17:58]:
Any predictions on the future of performance marketing?

Sean Ryan [00:18:02]:
No, I just think it’s going to continue to be, to, to be really, really relevant. I think at the end of the day, what we do for brands is we provide a direct way for them to generate revenue. And I think that as things change in our industry, as the noise increases, as, you know, more solutions come along, you know, you, we as a company and companies like us need to really, really be able to clear, clearly communicate to brands, you know, our ability to drive valuable users to their, to their products. And I think that that’s always going to have a really important home in this space. And I think that that’s something that we just need to continue to make sure that we educate brands on the value of that. As confusion kind of increases overall in.

Marshall Nyman [00:18:48]:
The space, what are some major challenges the industry is trying to tackle?

Sean Ryan [00:18:52]:
I think in our space it’s that there’s, you know, again, you know, I said this to someone the other day, back when I started there, you know, there was this ability that if I was calling on a brand when I worked for a large publisher, I sort of earned my right to be in the lobby waiting to meet with that decision maker, right? And so unless you were sort of the size and stature of a brand like ours, whether that was, you know, Ladies Home Journal or People of Rolling Stone, you weren’t. You weren’t able to get a seat at the table. The challenge now is, you know, I’m a brand. I’m a publisher that has one and a half million subscribers. But a lot of my outreach for brands comes through email, unfortunately. I try not to be that way. But what’s happened now is that because it’s so easy to spin up newsletters now, someone that has 5,000 subscribers doesn’t really understand that their value is not nearly as valuable as ours, yet they still have the same ability to be in the lobby of that same agency. So it’s just become.

Sean Ryan [00:19:48]:
It’s becoming dangerous where it becomes harder and harder for us to educate decision makers that we are a brand that’s been around for a long time and have the scale that they need. And it’s becoming a situation for people like you, Marshall, and people and agency people, where there’s just too many people trying to get your attention. And when that happens, you start to tune out, and it becomes harder and harder for us to get attention with the people that really we should be having conversations with. So that’s the thing that kind of keeps me up at night.

Marshall Nyman [00:20:14]:
Like, what’s been your favorite part of working in the performance marketing industry?

Sean Ryan [00:20:18]:
Like I said, my ability to show brands that I brought them value. My, you know, hearing from brands that they’ve seen a huge lift when they run with us. Even, you know, publishers, right, Publishers that work with us, they’ll come to us and say, like, my God, you know, you feature one of our articles. We saw a huge spike in traffic. I think that stuff’s really neat. Separately, you know, I’m really proud of the fact that I have a company of six to seven really great people, including, you know, my founder and everybody that works with us. And I love the idea that I was able to build a company and create a. Create a job for five to six people and, and help them, you know, support their families and.

Sean Ryan [00:20:53]:
And build a life. And I think that that’s something that’s just amazing. You know, people like us and you, Marshall, you do the same thing. It’s, it’s a great feeling to know that you can hire really good people and help them get their life going and help them build it and, and be part of that. So I think that’s probably the thing I’m most proudest of, stuff.

Marshall Nyman [00:21:07]:
I agree. That’s absolutely a very rewarding part of what we do. Well, a big thank you to Sean Ryan for joining the podcast this week. Some great insights into his background and how you could work with Rotary. What’s the best way for listeners to connect with you?

Sean Ryan [00:21:20]:
Yeah, please reach out. My email is scanrotary digital.net Love to hear from you separately. You can follow me on LinkedIn. I know there’s a lot of Sean Ryan’s out there, but if you look up Sean Ryan accelerator, that’ll be me. And you’ll see obviously the company Rotary. So please, you know, reach out to me on LinkedIn or reach out to me directly. I’d love to hear from you again.

Marshall Nyman [00:21:40]:
Thank you to Ryan for joining the podcast this week and to our producer, Leon Sonkin. If you’ve enjoyed this content, please give us a like and follow. Thank you for listening in. I’m Marshall Nyman, host of the Performance Marketing Spotlight and founder of C&CEO of Naimo and co. Signing off. Thank you and have a great day.

Sean Ryan [00:21:57]:
All right, to you.

Marshall Nyman [00:21:59]:
It.