Episode #55 – The Performance Marketing Spotlight with Craig Swerdloff

Marshall Nyman [00:00:02]:
Hello and welcome to the Performance Marketing Spotlight. I’m your host, Marshall Nyman, founder and CEO of Nymo and CO Company. Each episode I bring you someone with deep experience in the performance marketing space where they share their career journey and insights about the industry. Today I have Craig Swerdloff from Wellput. Welcome to the podcast, Craig.

Craig Swerdloff [00:00:21]:
Thanks, Marshall. You said my name perfectly. Great job.

Marshall Nyman [00:00:24]:
Well, that’s a good start. Excited to have you on today. And let’s get right to it. Can you introduce yourself to the audience, tell us who you are when you’re not working. Maybe some fun facts you can share about yourself.

Craig Swerdloff [00:00:34]:
Oh, man. Yeah. I’m Craig Swerdloff. I am living in Massachusetts currently. From New York originally, which makes it tough. I’m a Jets fan living in Massachusetts. As you can imagine, that’s quite hard. What am I doing when I’m not working? Well, so I do a number of things.

Craig Swerdloff [00:00:52]:
I play pickleball, which is taking up a lot of my time. Recently. I ran a half marathon trail race this past weekend. Didn’t train much for it and you can imagine the result was probably pretty predictable. But yeah, I’ve got two kids in college and a dog and a wife and yeah, having a good time.

Marshall Nyman [00:01:13]:
Well, we definitely won’t talk about the jets because there’s nothing too exciting there to bring us.

Craig Swerdloff [00:01:18]:
Let’s move right on from that.

Marshall Nyman [00:01:20]:
So how did you get your start in marketing?

Craig Swerdloff [00:01:23]:
Actually, I’ve been involved in the online advertising industry since the mid-90s and it happened by sort of happenstance. I was a senior at University of Vermont and this was in 95 and I needed one more credit to graduate. And my professor at the time said, hey, I know a guy who’s got a coffee shop down in downtown Burlington and he needs somebody, a marketing intern. And I said, great, sign me up. Well, it turned out that this coffee shop was the first Internet cafe in the state of Vermont. It was called Cafe no, no. I went down there and I was blown away. This guy had 566 dial up Internet, which was much, much faster than what we had at the UVM tech lab.

Craig Swerdloff [00:02:16]:
17 inch monitors. And we were teaching classes on how to use the Internet. We were building websites for companies and yeah, so that was my first sort of entrance to online advertising, marketing, the Internet really in general. And so when I left Vermont, I graduated that spring. I came home to New York and I asked my father if he knew anybody who could get me a job. And he said, well, I know a guy who owns a building in downtown New York. And I think he has something to do with the Internet. So it turned out this friend of his owned the first building in Manhattan that had high speed Internet connection.

Craig Swerdloff [00:02:58]:
And it was actually called the original Silicon Alley building. And so I called this guy up and I said, hey, how do I find out which companies are in your building? And he said, you go to my website? Of course. And so I did. I went to his website and contacted every company until somebody hired me. And that company was called Click Now. And it was an Internet advertising network. So they would represent websites for ad sales. And we had different verticals like golf and sports and finance.

Craig Swerdloff [00:03:25]:
And we built that business really quickly and eventually sold it to 24.7Media. And I was at 24.7Media from that acquisition until 2002. I survived the dot com bubble burst in 2000, 2001, we grew that company. 24.7 had thousands of employees in 50 plus countries. So it was quite a wild ride for me. So anyway, that was my first entrance into the world of online advertising and marketing.

Marshall Nyman [00:03:55]:
And then the world of online advertising really kind of pushed you into the world of newsletters and email marketing. I know you were mentioning earlier that you’ve been inspired by Morning Brew, the hustle, the skim. So what shifted from the more traditional side of media onto the newsletter side?

Craig Swerdloff [00:04:14]:
Yeah, 247 in the late 90s, started acquiring companies. And as a sales manager, we were expected to sell every product in their portfolio. And a couple of their products were actually email products. So they had early esp, the technology to send email. But they also owned an email list brokerage business which essentially meant you would rent somebody’s email list to send your message to their customers. And at the time I was living in Atlanta and one of my big clients was Bell South. And they loved email list rental. It drove so much performance for them.

Craig Swerdloff [00:04:55]:
So I soon started realizing that I could make a lot of money selling email. And really that was the first advertising product in the email channel that became a core part of my business. And eventually when I got laid off at 247 in 2002, I started my own email list brokerage company. Anyway, long story short, from there, 2002, for the next, I don’t know, 23 years, I’ve been really focused on the email channel and advertising specifically. And so we’ve tried every different ad format and email channel. I was on the board at live intent for 10 years. I chaired the IAB email committee for two years when I saw what Morning Brew and Daily Candy and the Skim and the Hustle were doing with sort of newsletter first publishing. They had websites, but they were really just there to drive people to sign up for their newsletter.

Craig Swerdloff [00:05:47]:
They were engaging their audience in the newsletter, and they were monetizing their newsletter through integrated sponsorships. That’s kind of when it hit me. I was like, that’s the perfect advertising format for the email channel. And so we have two co founders. We’ve started several businesses together. We’ve had some success. We sold our last two companies, but at the time we were running a business called Traverse Data, and we decided that we were going to pivot into email newsletter sponsorships. We sold traverse data to DMS in 2022, and we’ve been full time on well Put ever since.

Marshall Nyman [00:06:22]:
Amazing. Well, I got my start in email marketing on the affiliate side with list Brokering. So I definitely know that space very well. And it’s very fun, very complex, and always keeps you on your toes. Every day is a new day.

Craig Swerdloff [00:06:37]:
I knew we were cut from the same cloth, Marshall.

Marshall Nyman [00:06:42]:
So tell us a little bit about Wellput and what led you to create it.

Craig Swerdloff [00:06:47]:
Yeah, I think the biggest thing is that buying and selling newsletter sponsorships really kind of felt like it was stuck in the early 2000s. To me, everything was manual. Reaching out, finding the right newsletters, negotiating, collaborating on, creative tracking. It’s just incredibly high friction and it’s hard to test. And for publishers, they’re out there selling newsletter sponsorships to brands. But if you’re a small newsletter with 50,000 subscribers, it’s really hard to get in front of the brands that you want to talk to that your audience will find appealing. And so we just saw a need in the market for a marketplace to make it much more efficient and lower risk for brands to test newsletters, identify high performers and optimize their campaigns for performance. And also for newsletter publishers to fill unsold sponsorship inventory in their newsletters.

Craig Swerdloff [00:07:54]:
And very importantly, with brands of their choosing. There’s been programmatic advertising solutions for publishers in the market for a long time, including Live Intent. But brands have little or no say in terms of which sponsors or which advertisers show up in their newsletter. And so when we started well Put, we really focused on giving publishers control and choice, so they have the final say on which sponsors they want to accept into their newsletter. And that’s been a big change for us.

Marshall Nyman [00:08:29]:
How did you come up with the name? Well put.

Craig Swerdloff [00:08:31]:
I mean, you’ve been through naming companies in the past. It is hard work. Originally, I think we were calling the Company Email Advertising Solutions was our first name and we looked at a lot of different names. It’s really hard to find website, domains, URLs, trademark protection. There’s all sorts of issues that we had to go through in order to find the name. The name that I liked the most was actually bespoke, because everything’s so custom, it’s a sponsorship, it’s not a programmatic ad. But my friend Tink Taylor, who is from the uk, said, absolutely not. You cannot use that name.

Craig Swerdloff [00:09:15]:
Because he felt like nobody in the US knew what the word bespoke meant. And so that was the sort of turning point that led us to choose well Put. I’ve since come to find that everybody in the US knows what bespoke means. And, yeah, Tink was wrong. I guess he just assumed that all Americans are stupid and wouldn’t know what it means. But regardless, we wound up with well Put. And I couldn’t be happier. I think it’s a great name, these sponsorships, they’re well put, they’re well placed inside of the newsletter.

Craig Swerdloff [00:09:44]:
They’re native. They’re natively integrated into the content in a way that’s not disruptive, that flows with the reader’s experience. And so that was the genesis of the name.

Marshall Nyman [00:09:56]:
We use a lot of pressure with coming up with a name, and it’s one of those things, once you have a name, it’s hard to change it. So you really feel like you gotta start on the right foot with that one.

Craig Swerdloff [00:10:05]:
You really do. Our last company or two companies ago, we called it leadspend. And that was because originally the company was going to do scoring of leads using the email address as an identifier, as a predictor of quality of the lead, because people don’t give their primary email address unless they’re truly interested in something. But we pivoted and went into email validation technology. And the word, the name Leadspan had nothing to do with what we wound up doing. And so we tried to change, but everywhere we would go, affiliate some at different conferences, people knew the name Leadspend and it just stopped. And so we never did change it. We sold that company to Experian 2013.

Marshall Nyman [00:10:51]:
Fun fact, the actual original name, Anaima, was Caveman Consulting. And I hated that name so much. So I was so glad that we came up with something different. But most people don’t even know that it’s so easy.

Craig Swerdloff [00:11:04]:
Even a caveman can do it.

Marshall Nyman [00:11:06]:
Exactly what makes well Put unique?

Craig Swerdloff [00:11:10]:
Well, I think there are a lot.

Marshall Nyman [00:11:12]:
Of.

Craig Swerdloff [00:11:14]:
Platforms that brands can use to buy newsletter sponsorships, but they’re really sort of one off and still manual. So there’s companies like Paved and Buy Sell Ads. Linkbee is another where you can go in and you can find relevant newsletters. You can pick the ones you want to work with. You can execute a buy or a campaign with those newsletters and you test and you hope it works. And if it works great, then you buy it again. What we have found is that that process of testing newsletters one by one can be very slow, but also very risky. Most newsletters won’t come close to hitting an advertiser’s performance goal at unoptimized pricing, at the pricing that the publisher is asking the brand to pay to sponsor their newsletter.

Craig Swerdloff [00:12:21]:
You wind up testing a bunch of newsletters and very little works. And by the way, you’ve now blown through a significant amount of budget testing. What we’ve done is we’ve made well put for brands. It’s very easy and also low risk to test lots of targeted newsletters. So we’re limiting the spend per newsletter during testing to just a tiny fraction of the advertiser’s budget. And we do that on purpose because we know that most of them won’t work and we want the advertiser to continue to have budget left to then focus on the things that are working. And then we dynamically optimize the CPC rates with those newsletters that are working to hit the advertiser’s performance goal. And that is very unique.

Craig Swerdloff [00:13:06]:
There’s nobody else who’s doing dynamic optimization of pricing to hit an advertiser’s performance goal with newsletter sponsorships today. So that is probably the thing that from an advertiser’s perspective makes Waltpet very.

Marshall Nyman [00:13:18]:
Unique and reduces a lot of their risk. What are things brands should consider before getting started in the newsletter space as.

Craig Swerdloff [00:13:24]:
Far as like other channels or like.

Marshall Nyman [00:13:28]:
Do they need assets, a budget? Like if somebody’s ready to test newsletters, like what do they need?

Craig Swerdloff [00:13:33]:
They definitely need a budget, right? Nothing’s free. They have to be willing to take on some risk, right? There’s, there’s testing that needs to happen in order to find what works. And so whenever you’re testing a new channel as a brand, you have to allocate budget for that. You shouldn’t expect it to hit your goal right out of the gate. As far as assets, they don’t need much. I mean, we can repurpose whatever they’re using across other channels like meta to make it work for newsletter sponsorships, typically from an asset perspective, you need long form text copy that really explains your value proposition or your story to the audience in a way that you think they’ll find compelling. And the goal is to get them to come to your website and then from there move them down, funnel from intent consideration to conversion. And then the other thing they probably need is some form of tracking.

Craig Swerdloff [00:14:30]:
So either through an affiliate platform or an analytics tool. But they need the ability to track how the traffic that we’re sending them converts and performs on their site. But those are probably the two big things that they need.

Marshall Nyman [00:14:46]:
And as far as, like a timeframe, I know you said it’s a lot of testing in the beginning. How long does it take for a brand to kind of figure out what partners are working and they can start to see this scale up?

Craig Swerdloff [00:14:58]:
We know within a month or two whether or not the campaign’s gonna work, right? If we go out and we start testing 10 to 20 newsletters within the first month, and nothing works, nothing’s viable, then we know right away that that campaign isn’t gonna perform. So the risk for an advertiser is pretty limited. Right. We know pretty quickly what winds up happening is if we run a campaign month one, we’re testing 10 to 20 newsletters, we would expect to find several newsletters that can hit the advertiser’s performance goal at optimized pricing. And so we’ll make the campaign available to those newsletters at optimized pricing that we expect them to take based on what we’ve seen them pick up historically. But it may take a month or so to get those newsletters to run the campaign again, because they’re working with wellput to fill whatever unsold inventory they have. And so it does take, you know, three months is what we typically ask for, which is enough time for us to prove that we can find newsletters that will hit their performance goal and that we can optimize the pricing to hit their performance goal.

Marshall Nyman [00:16:10]:
On average, what’s the benefit for publishers to work with? Well put.

Craig Swerdloff [00:16:14]:
Yeah, I mean, look, if you’re 100% sold out on sponsorship, inventory, as a publisher, then good for you. There’s no reason to work with well put. What publishers get from well put is the ability to fill any unsold inventory they have with brands of their choosing. So they come to our platform, they sign up, and then they can log in and see dozens of campaigns that have been curated to them based on what we know about their audience and their content. And if they find something they like, Then they can reserve it and they can choose from different creative templates, the one that most closely matches their style and copy and paste it, put it into their newsletter and get paid for the clicks they generate. It’s also beneficial if you’re a publisher. Diversity of sponsors is important. And so rather than running the same sponsor over and over, if you want diversity, well put has a fairly significant pool of advertiser demand that they can choose from to rotate sponsors into their newsletter as needed?

Marshall Nyman [00:17:16]:
Well, nothing’s hotter than AI right now. How are you leveraging AI into your product?

Craig Swerdloff [00:17:22]:
Yeah, well, we could talk about how. I think AI is a lot of hype, at least presently, but we do use AI. I use it every day. But from a product perspective, we’re integrating AI into the targeting process of WellFit. So historically, when an advertiser told us who their target audience was, we would match them up with appropriate newsletters based on sort of manual curation process, using what the newsletter publishers told us their audience is and their content, what their content’s about. That process is very time consuming, but also really inefficient and inaccurate. And so we’re using AI to look at the archives of newsletters and understand really what the newsletter is about and who their likely audience is. And also to make better decisions around which newsletters are truly relevant for a brand and their audience.

Craig Swerdloff [00:18:23]:
And so that is, it’s having a big impact on performance.

Marshall Nyman [00:18:28]:
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Marshall Nyman [00:19:05]:
And I’m guessing you’ll be there, Craig.

Craig Swerdloff [00:19:08]:
I will. Although I wish I had waited to buy my ticket. I could have used the 20% off.

Marshall Nyman [00:19:14]:
There’s always next time.

Craig Swerdloff [00:19:15]:
I guess they. They split the difference on the timing this year, Right. Last year it was early February, right? And historically it’s like the first week in January. So I think everybody complained last year it was too late. And previously they complained it was too early, so they split the difference.

Marshall Nyman [00:19:30]:
I think for this year it’s driven by the Super Bowl. I know it’s going to be in Vegas again, so I think they’re having it a little bit earlier so it doesn’t go up against the super bowl. And I think CES is a couple.

Craig Swerdloff [00:19:41]:
Days before, so that’ll be perfect because then if my jets are in the super bowl this year, I’ll be able to stay in Vegas for the whole time.

Marshall Nyman [00:19:48]:
I think you and I are going to be in the same boat, competing for the number one spot. I’m going to be rooting for the Dolphins to lose to the jets in the next couple weeks, so we can have a worse record than you. Any other conferences you’re planning on attending next year?

Craig Swerdloff [00:20:05]:
Yeah, we we’ll be at all the major performance marketing conferences, Impact, DJ Rakuten and others. I don’t know if PI Live is happening again this year in the US And I know we were there last year. We’re also looking at expanding into other conferences. So E commerce is a big category for us. So we’re likely to be attending some E commerce and shopping conferences this year. Etail, shop.org, et cetera.

Marshall Nyman [00:20:39]:
So tracking can be a big challenge. How are you tracking campaigns and how do you think we can improve tracking in general?

Craig Swerdloff [00:20:45]:
Yeah, tracking is, I think, the biggest challenge. It faces the affiliate marketing industry or performance marketing industry overall. So we integrate with clients with whatever technology they use from a tracking perspective. So often it’s an affiliate platform or a tracking platform. So whether it’s Impact or CJ or Rakuten or Partner Stack or Drawing Blanks, but there are lots of others out there. And then occasionally they also will use some form of analytics platform, whether it’s Google Analytics or another. And so they’re coming to us with some form of tracking already in place and we’re integrating with them to track through whatever platform they use. Occasionally we use a pixel.

Craig Swerdloff [00:21:37]:
We can also use a postback. So lots of different options from a tracking perspective. But here’s the sort of cold reality of tracking. It’s just wildly inaccurate. I think we were at CJ earlier this year and one of the bits of data that I got from CJ was that I think it’s 30% of consumers don’t enable cookie tracking when they come to a landing page. And so right out of the gate, if you’re a publisher and you’re driving traffic to an affiliate’s website, potentially 30% of the conversions that you’re driving are not being tracked and attributed to you successfully. So that’s a big miss both from for the publisher, but also for the affiliate. Knowing who’s driving or where conversions are coming from and giving people appropriate credit for those conversions is important because it allows you to pay more to those affiliates that are performing well.

Craig Swerdloff [00:22:40]:
But if you don’t know, you can’t do that, you can’t attribute those conversions and that’s a big miss.

Marshall Nyman [00:22:46]:
Email hasn’t changed drastically over the last few decades. Any predictions on what the future of email marketing may look like?

Craig Swerdloff [00:22:53]:
Well, email marketing is kind of a. It’s a broad term. Right. It includes advertising, but it also includes customer relationship management. Right. The actual sending of email to my customers. I’ll focus specifically on the advertising piece of it because that’s really where I earn my living. But yeah, I mean, I think it’s definitely harder for advertising to get into the inbox.

Craig Swerdloff [00:23:23]:
We’ve seen a shift away from dedicated email in the performance marketing space over the last really, it’s really over the last decade, but I think it’s been accelerated over the last few years. It’s really, really getting hard to get into the inbox with a dedicated email ad. And so I think publishers historically who made their money in that space are shifting towards more content based strategies. Right. So newsletter first and then integrated sponsorships into those newsletters is a more sustainable model. But still, I do think that the inbox is changing significantly. I use a tool called Fixer. Other people use Superhuman.

Craig Swerdloff [00:24:12]:
These tools are utilizing AI and machine learning to get better at filtering out the things that we don’t want that we’re not interested in. And I think that we’re just in the first inning of that. Even though email has been around for 30 something years, actually I guess it’s 50 years now. We’re still in the first inning of what the inbox in the future looks like. And I suspect that if you’re, if you’re not sending email that people really want to read and engage with in the future, you’re not going to get into their inboxes.

Marshall Nyman [00:24:50]:
It just keeps getting harder and harder to get into those inboxes. The ISPs keep making it more and more challenging. And so I think that’s going to always be a big thing in the space is how you can actually get in front of the customer, not just send them an email, but send them an email they’re actually going to be able to read.

Craig Swerdloff [00:25:08]:
Yeah, I suspect we’ll have an agent in the future that Just tells us like, you know, if anything there, if there’s anything in our inbox that we need to be aware of or that we need to respond to or there’s anything that’s relevant to, you know, what we’re doing today or what we need this week, I suspect that there’s going to be an agent that makes that really, really efficient and easy. And we’re not going to be going through our inbox and, you know, marking emails as read and moving them to a folder and, you know, responding with it with a, with a basic draft to people’s emails. So I suspect that the inbox experience is going to get much, much better and more efficient for people over the coming years.

Marshall Nyman [00:25:49]:
It’s due for a major shift. Absolutely. You know, as I was saying, it hasn’t changed too much over the last few decades, so it seems like it’s due for some major shift and I’m sure AI is going to be a big part of that.

Craig Swerdloff [00:26:02]:
Yeah, we have a client actually called Khaki, which is pretty cool to start up and they are rethink the inbox entirely. They want it to be almost more like a, like a magazine, like an entertainment portal that just shows you all the content that you need and it’s categorized and really easy to access and read and use. So I’m actually really excited. I still think I’m. It’s kind of interesting to me that even though this channel email is 50 years old, there’s still a ton of innovation happening. And there are a lot of companies like Wellput, like Aki, Beehive and others that are raising lots and lots of money. Letterhead, I think, announced last week that they raised $34 million. Email company substack raised a billion dollars earlier this year, Beehive raised $30 million.

Craig Swerdloff [00:26:59]:
So there’s just a lot of innovation still happening in email channel. Exciting.

Marshall Nyman [00:27:04]:
And I think with a lot of the changes that we’ve seen recently with Google and some of the social networks, we’re seeing a lot of content creators actually lean into newsletters and make that a bigger part of what they were doing. I think the biggest thing with email is that you have a person’s information where you connect someone via social. You don’t really have a direct relationship with them. Something could change there where you own the email list. That’s a valuable thing. So I think that’s like a big shift that we’re seeing on the content creator side is they’re leaning very, very heavily into newsletters right now.

Craig Swerdloff [00:27:40]:
Absolutely. Yeah. Look at the success of Substack and Beehive and Kit and some of these other platforms that enable writers to build huge audiences and manage and monetize those audiences. It’s amazing to me.

Marshall Nyman [00:28:01]:
Yeah, everybody was focused on building their blogs on Google and then Google deprioritized, you know, how everybody was ranking. And so now this seems like a good place for everybody to be where, you know, you’re not relying on rankings. You know, you just have your user base and you send them that message and it seems like almost like a cleaner line of communication.

Craig Swerdloff [00:28:20]:
Yeah, definitely.

Marshall Nyman [00:28:21]:
What has been your favorite part of working in the performance marketing industry?

Craig Swerdloff [00:28:25]:
Well, I was going to say the people, but you told me that everybody says that, so I’m going to come up with a different answer. What I love is the, you know, the measurability, the accountability and also, you know, when something worked, you know, it worked right away and, you know, to see something performing and hitting an advertiser’s goal or a publisher’s goal. When I get emails from publishers that they love. Well put. And the service we’re providing them, that boost of serotonin. Serotonin, right. That’s what we’re talking about. That boost of serotonin.

Craig Swerdloff [00:29:04]:
That’s fantastic. Makes my day a lot brighter. And when I see an advertiser’s campaign hitting their performance goal and scaling across the newsletter channel. Yeah, I mean that’s, I think why we all go into business is, you know, we like to solve problems and make people happy.

Marshall Nyman [00:29:25]:
I think all marketers like when something works, we test a lot of things, but when something actually works and you know, you found something, I think there’s, yeah, no bigger serotonin boost than that. So probably a good place for us to wrap. Big thank you to Craig for joining the podcast this week. Some really great insights into his background and how you can take advantage of newsletter marketing with. Well put. What’s the best way for listeners to connect with you?

Craig Swerdloff [00:29:49]:
Thanks, Marshall. LinkedIn is probably where I’m most active and of course, via email.

Marshall Nyman [00:29:56]:
Perfect. Well, again, thank you to Craig for joining our sponsor affiliate SummitWest 2026 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 and CEO of Nymo and CO Co signing off. Thank you and have a great day.