The Content Engine Behind a $22m Bootstrapped SaaS Startup

The Content Engine Behind a $22m Bootstrapped SaaS Startup

Join us for a deep dive with Adam Robinson, the strategic mind behind Retention.com, as he unpacks the essentials of engaging content creation and audience connection. In this episode, Adam shares his playbook for turning everyday insights into compelling content narratives, the intricacies of maintaining authenticity in a crowded digital space, and building a loyal community in the B2B ecosystem.

February 6th 2024

February 6th 2024

Adam Robinson, CEO of Retention.com

Adam Robinson, CEO of Retention.com

Key takeaways

Key takeaways

Key takeaways

In SaaS, Brand and Community Are the Lasting Moats

Without built-in network effects, SaaS companies must differentiate through brand identity and community-building. The founder stresses that these two are the most sustainable competitive advantages. By creating content, telling authentic stories, and forming emotional connections—not just around products but broader tangential ideas—they're building a defensible position in a highly commoditized space.

Content and Audience Strategy Fueled Product Direction

What started as authentic personal storytelling on LinkedIn evolved into a full-fledged demand engine. The founder’s shift from generic eCommerce commentary (which felt inauthentic) to candid, “work-in-public” B2B insights unlocked high-performing content. These posts began generating leads, validating demand, and even shaping the company’s new B2B product strategy—audience engagement preceded product-market fit.

Media-First, Product-Second Is a Strategic Go-to-Market Play

From a reality-style video series to weekly behind-the-scenes strategy sessions and influencer-led video campaigns, the company is running a media engine that rivals traditional GTM efforts. The philosophy: by turning internal operations into immersive narratives, they capture attention, build trust, and dramatically lower customer acquisition costs. This theatrical lens guides everything from product rollout to support strategies (e.g., fully AI-powered support for virality).

Freemium and Viral Distribution as a Growth Lever

Learning from Mailchimp’s playbook, the founder is focused on building a high-utility freemium product (LinkedIn visitor-to-Slack ID) with broad appeal and viral potential. Their plan: use a free, high-value hook to grow top-of-funnel adoption, then upsell productivity-enhancing features. This lets them grow rapidly without traditional sales pressure, especially in a B2B market less constrained by privacy regulation than DTC.

Transcript

00:00:00:00 - 00:00:32:13

First of all, I'm going to make two big statements. And these days in SAS in particular, brand and community are the only moats you have. If you don't have network effects, which like a lot of SAS, doesn't have. Right. We don't have any network effect whatsoever. So my moat is going to be my brand. And if I can build a community around not even around the technology, but the idea is that we are, you know, problems tangential to the ideas that I'm talking about.

00:00:32:15 - 00:00:51:13

I know, so weird. So I'm curious about that though. Do you have is I was talking to my video team earlier and I'm like, do you just have someone, like, traveling with you and you're in the house 24 seven? How would this happen? So the most amazing thing about that whole charade, in my opinion, is the fact that it wasn't actually that invasive.

00:00:51:18 - 00:01:13:14

So dude traveled with me all. John is his name. He travel with me last year everywhere I went for work. And then Christy, who made the show, interviewed me like this on Riverside once a week for an hour about what was going on. So? So basically that went on for a year and then so he was just like, traveling with you for the entire year.

00:01:13:15 - 00:01:34:06

Yeah. Yeah, yeah. Whenever I traveled for work, he would go and I think I went on like 5 or 6 trips. And then the story happened over a year. But the episodes, the episodes are not sequential, if that makes sense. Does that make sense? Like, you guys basically piece them together? Yeah, exactly. A lot of episode four happened in February, whereas like a lot of episode three happened in May, if that makes sense.

00:01:34:08 - 00:01:53:05

So the stories were cohesive within the arc of the episode, but it was not like she needed to pull from this, like, year long trajectory. Right? The amazing thing is, it feels like I was like Gary Vee and I had this guy following me around for the Daily Vee all day, every day, but that wasn't the way it was at all.

00:01:53:07 - 00:02:12:24

And I was just so impressed with the product. I mean, like, it's sitting on YouTube as a repository. We did not do anything to promote it on YouTube in any way. So like, it didn't get any audience on YouTube because I have no audience in YouTube. I'm not a YouTuber. It's not contextualized for LinkedIn. And what I mean by that is I could put the best text post up.

00:02:13:01 - 00:02:31:12

I could put one of those eight minute episodes up, and the view time of the video will be like 5 or 6000 minutes. If I'm like, really lucky if I put the same text post up and it's me sitting here acting like I'm on a podcast, speaking into my laptop monitor with no one on the other side, it will get 40,000 minutes views.

00:02:31:13 - 00:02:55:09

Dude, it's just a weird thing about LinkedIn like that video looks like Netflix. It doesn't look like shit that like like people. I guess on LinkedIn they want like, people making hot takes yappin about, you know, bootstrap versus VC or whatever. I was so impressed with that product that I hired the girl who made it full time, and now we're, like, making two other shows for the dark side of the business.

00:02:55:09 - 00:03:15:13

And then we're doing a bunch of crazy shit on the B2B side. Yeah, no, I think this is this is timely for B2B businesses for sure are starting to take more like like media companies and like building out a media engine. This is what we're doing at at our group too. I'm just curious, though, the evolution to like getting there, because I think a lot of business owners are curious about it.

00:03:15:15 - 00:03:31:08

Like even just understanding that take that you just had where it's like, if I'm giving a hot take on a podcast, it's going to crush. But this premium content, it hasn't yet found an audience on LinkedIn. So, you know, I just started recently following you. And then, you know, we hopped on the call. Did you just start on LinkedIn?

00:03:31:08 - 00:03:53:09

When did this become a part of your strategy? One step back. We're creating a you're using it. We're creating a website identity probably for B2B companies. And it's it's it's a massive freemium offer. Right. It's a free. But by the way it's un it's unbelievable. It's like seems like the web hook broke for a second. They were like, yeah, we need this.

00:03:53:09 - 00:04:17:04

We need this back. Yeah. So like community plays a massive, in my opinion, community is it. So two things. First of all, I'm going to make two big statements these days in SAS in particular, brand and community are the only moats you have if you don't have network effects, which like a lot of SAS doesn't have. Right. We don't have any network effect whatsoever.

00:04:17:06 - 00:04:37:12

So my moat is going to be my brand. And if I can build a community around not even around the technology, but the idea is that we are, you know, problems tangential to the ideas that I'm talking about. If we can build a strong community around that. That is the other thing that is incredibly difficult to build. Right?

00:04:37:12 - 00:04:54:24

And it's super long game and like it just is. I think those are the two moats. So we're trying to come up with media to put in this community space. You were talking about LinkedIn. I think the place that you start when you go to build community is on one of these social networks, depending on who your audience is, right?

00:04:55:02 - 00:05:20:01

Yours. It would either, in my opinion, be Twitter or Twitter. LinkedIn. Mine now mine before was the same. It was probably more Twitter than LinkedIn. The reason I started on LinkedIn is a year and a half ago, I heard the argument that LinkedIn was way less competitive. So like for the amount of active people on LinkedIn, only 1 to 2% of people create content versus Twitter is like almost 5050.

00:05:20:07 - 00:05:34:03

Yeah, everyone's creating. So so it's just really a lot harder on Twitter to break through. Even though less of the audience was on LinkedIn, I was probably going to get more bang for my buck starting there in like kind of learning the game because like I was on social media, I didn't know what the fuck I was doing.

00:05:34:08 - 00:05:56:11

So yeah, I was still afraid. But basically, Tommy from triple L was like, I have an agency on the side. I'll start writing for you. I'll just, like, get you going. And I'm very glad that I did. And he got me going. And one thing that I would say is like, you know, it didn't generate a ton of leads in the DDC space, but there are a lot of DDC agencies on LinkedIn, and there's a lot of other vendors employees on LinkedIn.

00:05:56:11 - 00:06:17:03

And it like it definitely raised the profile of our brand in the ecosystem. And I think it like made it easier to hire whatever, even though it wasn't like generating like, like hard leads like it is now for, for B2B. Right? So this is a really long story. But like one of the things we're gonna put in this community space is like me doing teardowns of my top ten LinkedIn posts.

00:06:17:07 - 00:06:37:24

And I literally just told her this whole journey with LinkedIn. Right? Like started with, you know, you show up, it's like, well, what should I write about? I mean, I don't fucking write. It's like, yeah, where do you start? Yeah. And like, I knew I had seen I was my business was in a, an incredible financial position. We were 12 millionaire and we had six employees.

00:06:37:24 - 00:06:53:21

When I decided to start writing on LinkedIn because we were going to, like, scale the company and try to create awareness. I knew from the prior 60 days that when I just said that statement, people were like, what the fuck? Because like, everybody's making less than $12 million and that's more than six in place, right? Regardless whether the SAS or not.

00:06:53:23 - 00:07:13:09

So I thought I'd seen some people work in public and I'm like, man, I don't give a shit. Like, I'll share my financials. I'll yeah, I'll share everything. Yeah, yeah. And like, I knew that that was probably going to do well because our business was doing so well. Right. It's not that interesting if like, some guy who's got less than a million in revenue was like, oh, I'm working in public, it's like, great.

00:07:13:11 - 00:07:31:20

Somebody shows up and they're like, I have 12 million arrow at six people. I'm gonna tell you everything I'm doing. It's like, wow. Like, even if I'm ahead of that, I'm going to lose some of that guy, right? So that was a foundational layer. And then there, like, you know, Tommy and whoever, they're like, well, just start writing about email and like it was 60, 40 like email and 40% work in public.

00:07:31:22 - 00:07:51:06

And I just like, hated my email content because I don't care about email marketing. I've never sent a DDC email. Yeah. You feel like you're like, almost lying a little bit. It felt very inauthentic to me. So then it slowly transitioned to all work in public. But like, I didn't know what I was doing. And this is like a weird thing to try to express.

00:07:51:06 - 00:08:10:15

Like my videos, if you go back and watch videos that I was making from like September of last year, they were so bad and like such rambles and like literally like, this is a person who doesn't know what they're doing, but like this is the guys first video, right? Like that's what it is. And then this guy who was like producing the videos for me, he's like, dude, watch this YouTube video.

00:08:10:15 - 00:08:26:24

And he's like, the guy on YouTube was like, do a hook, a story, three lessons, soft CTA. That's the format. So like, I got these fucking whiteboards. And then I started just like whatever was happening to me, I try to do one a day, right? That's what I kind of wanted to do, because some guy was like, see if you can do what I do.

00:08:27:01 - 00:08:46:22

I started doing that and I'd like, write them all and record them all, all in one session. I'd like, write the topics and then you know what I mean. I got a really good system for for recording and getting it cranked out, but still none of it felt like it was working. You know, like I do a video and it would get like 22 likes and you're like, I go to trade.

00:08:46:22 - 00:09:07:22

You know, I knew that it was captivating a very small audience because I would go to trade shows and I hear people say, I literally watch every single one of your videos, like, they're awesome, right? But like, I didn't know. I was like talking about work, like balance and, you know, spirituality or something one week and then the next week I would talk about like how to fire people and like, you know, how you like hire a players and shit.

00:09:08:01 - 00:09:25:23

No idea. And then I also thought I had this whole machine that involved a lot of people, and I wasn't really I didn't feel like every post was the best that it could be. So eventually I found my current guy, and, you know, I'm a member of this group called Pavilion. It's a revenue leaders group. And this guy, Sam Jacobs grows his entire business on LinkedIn.

00:09:25:23 - 00:09:42:21

He's got a really good LinkedIn game. You may have seen him. This guy Alec Paul is his coach slash consultant. He's not a ghostwriter. He's just strategic. And he's an editor. And he makes sure headline is the best it can be. And he knows exactly how the machine works, and he can show you different templates that hit and all this shit.

00:09:42:21 - 00:10:06:11

Right. So and like he, he keeps the top like the reflection on, you know, what's happening in your life. What should we write about this week? I need another post. I'm good, but that's what it is. And then he posts it, right? Started working with him, but I was still kind of aimed at how do I, explain, you know, how can I talk about enough that is related to Shopify founders that like, we can see if this will pull leads in, right?

00:10:06:15 - 00:10:23:14

This one I think is interesting for you because, I mean, you're not an ecom operator, right? You haven't had an e-commerce store in the past. This was my whole internal conflict. But that's why it's so interesting you're going B2B and like now your audience is going to be massive and it's all going to be relevant to the this is my story.

00:10:23:14 - 00:10:42:16

With all this, I thought it was incredibly inauthentic for me to be writing about anything related to E-Com. What the fuck am I going to say that Nick Schwab and Sharma, like he's making landing pages for people every day, right? Like I'm doing nothing of the sort I am not. I cannot say a single thing to these people that they will think is valuable, right?

00:10:42:16 - 00:11:03:18

At least I felt so then, like we had a suspicion that we were going to make a product for the B2B audience like us, which you were currently using now around the middle of August. And I was just mentioning it to Alec in conversation. He's like, bro, if you actually sell something to that audience, meaning you like people like you, he's like, this is what I do.

00:11:03:18 - 00:11:23:21

He's like all my CEOs that I help sell into this audience. And he's like, we have a machine that systematically generates inbound leads. It will work, I promise. So at that point, I was like, cool, I'm going to see if I can write to these people salespeople, marketers and founders, right. And I just remember, like like it was yesterday, right?

00:11:23:21 - 00:11:42:07

Like there I had one post. So like my average post was like 30 likes or something, some shit like that. A great one would be 100, right? And then I wrote one that was like I spoke to 30 BTR leaders over the past, however many. And here's the eight things. And it was just pain that we were all feeling.

00:11:42:07 - 00:12:06:01

It was just this pipeline crisis where, you know, these Beatport medias are catching at nine ways on Sunday. People are being told not to buy in. Their fucking emails don't work anymore. Not yet. So I was like, wow, that was good. And then I sit down one night and I wrote three posts and one had done really well, and I wrote three, and I was like, I think these are going to be incredible.

00:12:06:06 - 00:12:24:09

And if they are, then I know what incredible is. And they hit and it was just like, yeah, you were like, I can now gauge, you know, what it's like. And I'm like, I'm like, if I'm right about this and I know what great is, like, I can keep this machine going forever. And I can't emphasize it enough.

00:12:24:13 - 00:12:46:14

In the 12 months up to that point, I had never felt anything close to that. Right. I thought the BTR post that did well was pretty good, but I wrote three and I was like these are going to fucking slam. And if they slam, then I know how to write, right? How long did it take you to get from point A to point B where you were like, I know it hits, I know it works.

00:12:46:19 - 00:13:03:19

Well, I mean, that was 12 months in. I got there in a very roundabout way. People could probably get there more directly, but like the reason I got there was because we the interesting thing is, one of the things that made me push forward with this B2B product is the fact that these posts hit so hard. Yeah, you were like, it's a self-fulfilling prophecy is a self-fulfilling prophecy.

00:13:03:21 - 00:13:17:11

I'm like, even if the product is like, okay, I can get so much reach on this LinkedIn thing and all these people use it, I should do it. And then we were like, I was like, my fucking business has a churn problem, you know? And like, I'm like, I'm going to avoid it in like, but that's that's commerce.

00:13:17:11 - 00:13:40:00

SAS right? Yeah. We thought that it was like because we were selling it to small people. I'm like, we're going to skip that this time. I'm going to go straight to the mid-market 30 to 50 KB. It's going to be one of those operations. But over the next three months when we were like getting beta testers on this product, my audience grew so much and the posts were just hitting so hard that I was like, if we make this free, then it was like an upsell, right?

00:13:40:00 - 00:14:08:16

If you're getting integrations right free. He's like, I was like a big freemium offer will help me disproportionately to somebody who did not have this megaphone already. It's getting real dark. It's like storming out. It's storming out there. Yeah. I'm concerned. Yeah. It's so strangely like the LinkedIn presence was like in forming the product. And it was also like informing the whole go to market strategy, like the fact that it kept going better and better and better.

00:14:08:16 - 00:14:26:13

But no, now I feel like there's like an actual. So now you have audience. You basically have red awareness top of funnel. You have like a channel to basically insert this product once it's ready. But you also think on the product side, this is going to crash because it's just it's just the superior business or you know, so I haven't used retention on the other side.

00:14:26:19 - 00:14:48:19

Right. Yeah. It's it's retention on the other side works really well for a really successful store. That's just the reality. Like if you are crushing it, it's like lighter fluid to make your fire bigger, right? If you are anything but crushing it, it's just not as obvious, you know, like it works great for some people. It doesn't for others.

00:14:48:21 - 00:15:08:24

But like, how can you argue with a free product that sends LinkedIn profiles to slack of people that were on your site? Like if you took the free thing away, then there's an argument. It's like, well, is this worth X per month? Right? I think there's there's a bit too about like when it's not a free product. You know, pricing is such an important part of the equation.

00:15:08:24 - 00:15:29:14

Like when you're figuring out product market fit and how how large your your Tam is to your point, like I'm noticing on the commerce side. Yeah, they're scrutinizing price so much like and the switching costs are just so low because they're a million of these software providers in commerce that it's like you need to have the the best product at, like the price where no one's gonna look twice.

00:15:29:16 - 00:15:52:15

I mean, that's my view. And my hope is that I'm trying to sell instead of like a price per lead. I'm trying to sell this idea that if you want to save time with integrations, pay 500 bucks. If you don't knock yourself out with a free app. Forever in my hope is that if someone actually wants to save time, then they had already found value from the free product and if they need to save time, $500 a month is a drop in the bucket.

00:15:52:17 - 00:16:11:14

Yeah, that's the hope. I like that. I think that's that's logical. So how did so okay so basically it took a year to get LinkedIn to a place where you were like, I know, I know what my audience wants to hear. I know that I'm producing this quality. And then at what point where you're like, let's go deep on, you know, basically making a reality TV show that was that was a year ago.

00:16:11:14 - 00:16:29:20

That was before my LinkedIn was hitting. That was a total yo, I don't know how else to say it, and I don't think it's repeatable either. I think it's like the girl, Christy, who produced the show that just does great work. And it was my like, I had zero creative input into that, you know? Yeah, you were like, here, I'm just filming like some.

00:16:29:20 - 00:16:48:24

Yeah. I was just like, I will, you know, she made the first couple episodes and then I even stopped watching them before she launched them because I was just like, dude, that's great, I don't care, you know what I mean? So yeah, she just, like, really does a great job. And, you know, it wasn't inexpensive. Like I think we spent like 250 on it.

00:16:48:24 - 00:17:05:09

Right. So like 18 episodes I mean that's fucking expensive when it comes down to it. I was telling myself there were five grand an episode, but it ended up being a little over ten. But, you know, and like, it's one of those things, right? It's like, what did that do for me? You know, I say that I'm not trying to get famous.

00:17:05:09 - 00:17:25:12

Meanwhile, I'm like making a fucking reality show about myself. And it was just like when I go certain places and people are like, I've watched every single episode. It's like that person is connected to everything that I am doing in a way that they could not have been any other way. Right? Like priceless. They're going to buy anything.

00:17:25:14 - 00:17:46:24

You're putting that totally. So like, I didn't feel compelled to continue doing that show just because I didn't think it was like the best use of our resources to keep that going. About me. Like we're making one about Kyle now, our partner guy, who it's called events that don't suck. So it's his journey to try to create, you know, an event motion that of events that people actually want to attend.

00:17:47:01 - 00:18:07:00

Right? Like, rather than these trade shows that we all fucking hate, and are super expensive. And then we're making another episodic show on the DC side called the Art of excellence, which basically profiles, you know, there's certain people in this ecosystem who are, like, revered by everybody else, and their stories are so crazy or they're or they're not.

00:18:07:00 - 00:18:27:06

Actually, GDC is really interesting. It kind of puts some like smaller founders on a pedestal. They're like sub $1 million Shopify stores. But yeah, you know, featured on every podcast. Like, you know, we're doing like Curtis from Portland Leather Goods, Ben from True Classic or whatever. So like these stories are just wild and they're not like they're not case studies.

00:18:27:06 - 00:18:46:13

We're not even mentioning our product or their success with it. It's literally telling the brand stories and just aligning their sort of excellent execution with our brand. And then that's the whole media product, which I think is like the ultimate show of confidence. Some people might say it's stupid, like to put so much so many resources into that.

00:18:46:15 - 00:19:07:17

But yeah, we're doing that. And then on the B2B side, one thing that I have thought that my work in public lacks on LinkedIn is really the ability to like two things. One, to get more immersed in my world. If you're just reading the LinkedIn post, like LinkedIn is like one of its faults with content creation is it's not there's no time scale.

00:19:07:17 - 00:19:23:04

You can't you can't, like, launch an episodic series and follow the episodes because it will serve you a piece of content that's from six months ago and somebody else piece of content that's from today. That's just the nature of LinkedIn. So one thing that I this is basically for me, that I'm doing it right, like I would have.

00:19:23:07 - 00:19:48:21

So, so like I run this incredibly detailed, hour long strategy and tactical call about the B2B product execution. Every Monday I'm going to record that hour long call, post the notion board online with all the key metrics, and then give like a Tldr at the beginning of it, and then do that every week for the entire year so that anybody can go back and see where we were in July, what we did and how it worked and how it didn't.

00:19:48:21 - 00:20:09:23

And like, you know, any of these businesses, 0 to 1, 1 to 10, I would have fucking died to know literally in a week to week basis what they were focused on, why they were doing, what they were doing or whatever. So that's something I'm putting effort into, like providing. It's like it's like not like stories like last year, but it's like, you know, I wanted to get more immersive into the actual company building.

00:20:10:03 - 00:20:27:22

And I think that that's going to resonate in a different way with this audience. Right. Because like, they're actually building these SAS companies. So yeah, that's what people want to hear, I think. How do you go about building like a media function and culture within retention? And like, what advice would you give to another founder who's like, I can't get my VP of sales to create?

00:20:27:23 - 00:20:54:23

Gotcha. This is what Alex says. My my coach. When other people see you doing it regularly, especially if it works, it will call them to do it as well. It has like, you know, we're getting Santosh involved. Kyle started getting involved. Diane's a little harder because she's so busy. But like when we hire like we just hired this guy Pete, because one of the things I'm trying to do with the B2B business is to make ChatGPT be the entire support org, not like 90% of it, like 100%.

00:20:55:02 - 00:21:19:13

So we like hired a guy to do that, and we're going to try to make him the chat bot influencer, you know, because like, everybody wants to hear that story of some startup that's killed with no people using fucking OpenAI. Right. Like, so we're going to basically sacrifice sales and support quality in order to just have our whole customer facing surface be chat bots only credible only only to yell about it.

00:21:19:14 - 00:21:44:18

Literally, the only reason we're doing it is because I think the story will create virality more than in more than offset what we're missing. So yeah, I mean, if you can tell from listening to me, I have now, I now think about everything I'm doing through this lens, through this theatrical. So like, what can I do? It's like, I truly believe the stuff I write about.

00:21:44:20 - 00:22:03:18

If you try to go hire a team of 20 stores and sell anything, it's not going to fucking work. Probably one person who's a talented growth marketer can do more than them. That's my guess. So it's like, what is available to you? You know, I just think the motion that will be the most successful is probably something that looks like what Joey Skin did last year.

00:22:03:20 - 00:22:24:22

Tiny internal team, massive UGC machine. Like, can I create a freemium plug product that, you know, maybe I'm giving people the free plan, a way to like post how in excruciating detail they book their first demo. Can I create this, you know, 20 LinkedIn posts a day of people saying, this is how I book to demo with retention.com, right?

00:22:24:24 - 00:22:44:07

I haven't seen anyone even attempt that yet. Definitely. On the B2B side. And it's funny, we've got Arjun on the pod next week, right? I mean, like go into more specifics about like how you're engineering these structures because on the B2B side, it's like human resource saying it's getting the right talent. Like I think that's something that that people are interested like that.

00:22:44:09 - 00:23:10:22

What I just said, I don't know how we're going to do it yet because we haven't gotten there. However, I'm going to try to start. I actually am working with this guy, Morgan Ingram, to start with ten sales influencers who are sort of known like you wouldn't call them Micro-Influencers, but they're not like big influencers. And I basically did a six month deal with him where, you know, he's going to fly these guys out to Atlanta and in a different in two per month and in a different spot, different location every week.

00:23:10:22 - 00:23:42:08

Like film them using the product and having success with it. That will turn into 3 to 5 pieces of content. And we're going to have them all agree to put a retention outcome title in their LinkedIn so that we can pay to promote it with thought leadership posts. So if he's he can do ten. And then, you know, Alec and I can also do ten, like our Performance Marketing girl and GDC side, we'll have this like massive library of content to just every day be promoting a different, different one with these like inexpensive thought leadership ads to like the audience we're trying to go after.

00:23:42:10 - 00:24:03:09

You know, I'm just trying to create the perception that we're literally everywhere. And before you started writing on LinkedIn, did you do any sort of marketing or advertising for retention to get you guys to 12? Oh, so literally to go 0 to 1, we have I'll send you a link to this. I did some Facebook ads for six months that like were hilarious.

00:24:03:11 - 00:24:24:05

So this was 20. It was early 20. It was late 2019, early 2020. And like Instagram Stories was starting to get big. Like people, you know, Snapchat, all that stuff. Like people were walking around like doing selfie videos with interesting backgrounds and trying to be amusing or whatever. So I was kind of like, what if you could do that?

00:24:24:05 - 00:24:42:22

But like, have it be answering the sales questions everybody had and they were funny enough where, you know, you could get an audience of people anticipating the ad next week, right? Do 1/62 ad per week so that my wife and I did it, these fucking selfie video ads. And, I have really low quality recordings of them on my YouTube page.

00:24:42:24 - 00:25:04:05

So you can put in the show links and yeah, like that, like Covid hit and like, people stop running ads like ad inventory got really cheap on Facebook. And it was just this amazing awareness machine that was bringing in horrible customers. But like, at the same time, the ads were paying themselves back in a day. So it was like, you know, if you want to go fast, you care about, time to pay back.

00:25:04:05 - 00:25:23:03

If you want to grow big, you need low churn basically is like the equation. So yeah, it was incredible to get them off the ground to get this off the ground. But then that stopped working because it was like they were bringing you know, Facebook is like anybody who runs Facebook ads I think would agree with this. It's like a 20% churn per month audience for like whatever you're you're selling a lot of the time.

00:25:23:03 - 00:25:48:18

So we had to stop running ads, that audience. And then eventually you're touching on churn. I want to talk about it because the first time we met, you referenced churn, how it's pretty, I guess negative in terms of how you tell you the value of retention. Yeah, it's bad on all fronts, but I want to just like kind of zoom into when you guys saw churn going up, how did you know what sort of actions did you take to either combat it.

00:25:48:18 - 00:26:06:15

So so here's what I would say. It's not that we've seen it really go up. The mistake that I made was a year and a half ago, when we thought we had found our true ideal customer profile. I thought it was going to be a lot lower at its end state than it is, so that makes sense. It's still way lower than it was two years ago.

00:26:06:16 - 00:26:27:21

I just thought we would be operating in like, you know, a klaviyo type world. I thought this was like so close to the revenue that, like, nobody would ever cancel it. And it's just as I learn, systems of record in martech tend to be the lowest churn businesses or being a super, like a non-negotiable part of the workflow.

00:26:27:21 - 00:26:46:12

You know, it just has to be there. The worst is selling leads to people because which is effectively what we're doing. We're selling intent data to small businesses. Selling intent data is an inherently high churn category. Small businesses is an inherently high churn buyer persona. So good luck with that. That doesn't mean we can't make it better. Of course we can.

00:26:46:12 - 00:27:07:09

The way that we are choosing to combat it is basically by tilting our sales going up a little bit, because we have learned that the tech works better for we're basically amplifying throughput of a store. So the more money you make, we'll make someone 100% of their been in cart flow, whether it's $5 or $500,000 a month, and we don't really charge linearly.

00:27:07:09 - 00:27:29:19

So people just tend to be more successful the bigger they are. And mid-market customers are stickier, period. Full stop than SMB like by orders of magnitude. So with that particular product, it's a lot that and then it's like the other part of it is just like being 100% certain that the product was onboarded in the right way, and that the customer actually understands what it does, which sounds easy, but it's just not.

00:27:30:00 - 00:27:52:03

Especially that last part. And yeah, I mean, but unfortunately, I don't think we're ever going to be klaviyo. It sucks. It's not like it's, you know, it's a really good business. It's just like the way companies can get really big is if more than 100% of your revenue is there the next year. And that's just not that's just not what a lot of the more recent SaaS companies in the Shopify ecosystem are experiencing.

00:27:52:09 - 00:28:12:24

Yeah, I know, I know that firsthand to I mean, it's just hard even with like a 10% churn, you basically need to replace your entire business next year. Yeah, exactly. Where are these stores coming from? Right. And like, fortunately for us, we run at a substantial EBITDA margin. But like a lot of people do not write the really dangerous position is if you're burning money for that outcome.

00:28:12:24 - 00:28:38:08

There's a couple things I want to touch on based on what you just said I want to talk about, like the privacy landscape and obviously like Shopify merchants, I think they like to think they're pretty well versed in privacy changes. I would challenge that a little bit. How does that differ on the B2B side? Because I don't even think B2B businesses even think about privacy, which is probably a really positive thing for your business, because and not to drag this out, I listened to another pod.

00:28:38:08 - 00:28:55:20

You did withdrew from post pilot, I think, and you spoke about how, you know, Klaviyo takes a totally different stance on privacy, and it actually hurts your prospects of being acquired by a business like that. And it obviously just makes it impossible, doesn't it? Yeah, it doesn't hurt it. They would just never they would just never buy it.

00:28:55:20 - 00:29:21:12

So yeah. Look, I would say the first question was so first of all, I don't think anyone has a deep understanding as a I don't think anybody really knows what these laws mean. I think and this is speaking on in terms of like the average of the people that we speak to on both sides, they all think that it is moving in an unfavorable direction, which the conclusion they jump to is, well, this will certainly be illegal soon because it's all moving that way.

00:29:21:16 - 00:29:48:17

Right? The beautiful thing is, I've spent hundreds of hours with privacy attorneys, in my personal view is that yes, it is moving that way, but it is moving that way in a way that will not affect our business, either being in compliance or not in compliance. It's not touching what we do as it relates to our business. The outcome of all these regulations is going to be more better and more cookie better acceptance with like more descriptive statements on them about what's going on.

00:29:48:18 - 00:30:09:10

They're not trying to do away with this technology. The spirit of these laws is to try to like, increase disclosure to consumers, but nobody understands that for one second. The other interesting thing for the Shopify audience, if that's who's watching this, is Cpra and CcpA doesn't even apply to people. It's under 25 million revenue. No one knows that that's that's 99.5% of Shopify.

00:30:09:12 - 00:30:33:15

Anyhow, on the B2B side, what I would say is there's this interesting kind of like bifurcation. So first of all, on the DVC side, whenever you're dealing with consumers, the privacy situation is much more sensitive. So that's great. On the B2B side, whenever you're dealing with businesses just in general, like there is no the only legislation that even touches business contact data is cpra.

00:30:33:15 - 00:30:52:04

And it's like not the same strictness as with the consumers. No, you're right, B2B companies, like they really don't give a shit about this up until a point when they do, and then they care more. So like if they've hired a chief information security officer, then this person's job is to basically create friction caring about this kind of stuff.

00:30:52:09 - 00:31:16:20

So we're focusing out of the gates on the smaller consumers anyway, with this free offer and trying to create virality and all that shit. And like people who can get the script on in a second, like, you're the perfect customer, right? This is exactly who we want to get. Like 250,000 people like this using it. At some point, we're going to start wanting to move up market, and at some point we're going to have to figure out whether that is something that is like just tricky to navigate or whether it's just like a nonstarter.

00:31:16:22 - 00:31:35:09

But the reality of it is it's like what we are doing is not, compliant in any way. It is. I would say it's gray area such that a lawyer would feel better about you not doing it than they would feel about you doing it. Right. Like that's just. But a lawyer would feel that way about anything that was risky in any way whatsoever.

00:31:35:10 - 00:32:07:02

I like this direction. I think for Shopify merchants, though, there's so much murkiness. Post 80, it's like, because you've done so much research on this particular topic, like, what's the end state of privacy? Let's just take the United States because, you know, obviously the other regions have different sort of policies, but where do you think it's headed? I mean, I definitely think it's going to get more restrictive, but I don't think it's going to become restrictive in a way that's going to cause a negative effect on people's businesses from where it is today.

00:32:07:07 - 00:32:34:04

Does that make sense? Like like I said before, I do think there will be, you know, people will have to sort of put more cookie banners on different places or whatever. I think that the fear is like greater than the future reality. You know, like anything that happens, it's it's not going to be like, for instance, Canada has a law that if you don't have like a recorded opt in date in URL in the last 18 months, you can't email these people.

00:32:34:08 - 00:33:00:06

It's like my view is that is never going to happen in the US. From what I've heard, the direct marketing agency lobbies very hard to keep. It can spin law as it is, and they reviewed it in 2019 and it doesn't feel like it's changing. The state level stuff is it's a lot faster moving. But another thing that I would say is there's no right to private action on anything related to what we're talking about.

00:33:00:06 - 00:33:18:08

Meaning like consumer data and messaging these people, that means an individual cannot sue you. It is going to be the government going after companies who are in violation of this. Where are they going to start? They're not going to start with some fucking Shopify store. And yeah, furthermore, the law doesn't even apply to people who have less than 25 million, right?

00:33:18:08 - 00:33:37:24

So like all I'm saying is like GDPR does apply to them. Right? So and that was a pain in the ass and the fear around this legislation and the lack of understanding of it is, in my opinion, much greater than the reality of the law for almost everyone who is afraid. That's the way I'm going to put it.

00:33:38:01 - 00:33:56:00

It's a good take, for, you know, I just want to switch gears to like, from your journey from zero to 12 or 0 ones, 1 to 12, 12 to where you guys are at today, you know, how have you adapted? How has your role changed? Like, how are you thinking about that as the business this year? I mean, that's such a good question.

00:33:56:00 - 00:34:15:14

So, I mean, I don't even work on the Shopify business anymore. I don't know if you knew that, like I'm 100. I mean, I could tell you're fully on B2B. This question is something I think about all the time, by the way, you know. Yeah. So I basically handed the reins off to my co-founder of the business, Diana Ross, who's very highly capable.

00:34:15:14 - 00:34:33:01

She has she's way better at some stuff than I am. I'm better at some other stuff than her. But we more or less think about things the same way almost always. So, you know, I have our executive meeting where we talk about that business. It's one hour, and then my one on one with her is one hour, and I have one on one with an who's VP product.

00:34:33:01 - 00:34:54:20

And we talks about DDC a little bit. That's it. I mean, no other time. In some cases I can be like, yeah, maybe I'm still like symbolically sort of the leader of the business, the public or whatever, but I have no role in it at all besides very big picture strategic like, you know, nudging people to like look through a different product offerings and stuff like that.

00:34:54:22 - 00:35:22:02

So my role has now become the founder CEO of a 0 to 1, you know, very public experiment where I'm trying to, like, do something I've never done and have a hugely viral plg thing with basically tons of resources, right. Which like, what's more fun than that? Right? So I'm not like last year was really hard. We hired way too many people way too quickly.

00:35:22:04 - 00:35:41:09

We had a hard downsizing and then slowly scaled back up in different parts. The organization and, I traveled a ton for the for the GDC side. You know, I had a kid a year and a half ago. So all that was happening at once and other than creating content throughout it all, kind of like nothing is the same as it was last year, you know what I mean?

00:35:41:09 - 00:35:58:00

Like, I'm not I'm not really hiring anybody. I'm not like, trying to like, grow, like I was trying to in many ways. I'm actually trying to build a brand in the same way, because our brand was at zero in January in the Shopify ecosystem. So a lot of that kind of work is the same. But I just started in a different place here.

00:35:58:00 - 00:36:16:20

Like I started trying to build this brand before we had the product, you know. But yeah, I mean, now it's like a lot of like talking to people like you who are using the product about what exactly you're doing. Like, that's so different than when you're going from 15 to 20 or whatever. Millionaire or like, there's there's none of those conversations you already know exactly what the product does.

00:36:16:20 - 00:36:38:14

You know. By the way, just on that note, two, we should have a separate conversation. But like, there's a whole analytics part of this business that I think would be incredibly interesting, the B2B side, 100 or so. Yeah. Like in terms of like the site visitors level of intent, I don't know, the level of detail on which, you know, like how many actions that they take on a particular site.

00:36:38:15 - 00:37:03:06

Like obviously you're seeing what you URLs they're on, right? Yeah. Yeah, we know that. We know the whole, the whole page of history like across multiple days, which is great. But you're only sending you're sending the last we played the last page, they ended up on our pages. Spent the most time in that. I don't know what's coming across in that webhook, but it's like LinkedIn profile URL like this.

00:37:03:06 - 00:37:19:02

And slug in the file there's two columns. One is a string of all the pages they viewed in the last session, and then the other is like the last 50 pages they looked at or something. So the interest, the latter may not be coming across in the webhook, I don't know. Yeah. We should we should talk about that.

00:37:19:02 - 00:37:46:16

I got a number of ideas on that front, but I mean, like to sum it up, though, it sounds like you basically scaled the GDC business. You went really deep on marketing last year. You developed this audience a lot of interest around, you know, you yourself as a founder, being really transparent about the business that you built and then through building that audience, you were like, hey, we could leverage our existing infrastructure on the on the GDC side to build a B2B product that has a lot more potential, and now you're launching it from scratch.

00:37:46:16 - 00:38:11:17

But really, you have a product team, you have a sales team, you marketing team. So in essence, your your job has become basically marketing and figuring out how you take this business, you know, beyond 20 million to 100 million, whatever it is. Oh yeah, very well summarized. And I kind of view my role is that it's like I kind of feel the burden to be the entire marketing engine on the B2B side and kind of most of the big picture product stuff, too.

00:38:11:19 - 00:38:29:03

You know, the main calls like, I'm not like in there, like critiquing UI or whatever, but it's like, yo, we should put a connect on LinkedIn button in slack. Let me, let me pull in something else. You said it. I think you said this in one of the episodes I watched. I watched two episodes. You said you sort of tracking week over week.

00:38:29:05 - 00:38:48:04

Gross. Yeah. And I'm assuming that influenced your decision on the GDC side to basically be like, yo, fuck this. I stopped two and a half years in. It's pretty cool to look at. I mean, we have three paying customers now because we haven't started charging people on the B2B side, but once we kind of start trying, I want to plot this side by side.

00:38:48:06 - 00:39:10:17

But yeah, we have had we had a down month in January 2021, January 2022 and April 2022 and then again this year. I mean, it kind of makes sense why it's like if you're going to cancel this, you're going to wait till after the holidays and then fucking turn it off, right. Like there's just you had you had a couple companies before retention or getting emails.

00:39:10:17 - 00:39:39:01

Were they in SaaS? Talk to me a little bit about that one. Really. It was like the one company that you could see that I had. I mean, I tried some other stuff, but like my first company was in the email newsletter space, it was called Rudely Email Marketing. Again, don't really care about email, but like somehow I was trying a bunch of different stuff and like, we found this way to basically like scrape the breadcrumbs off of this like massive constant contact machine.

00:39:39:06 - 00:40:00:18

That was that was the first email marketing company and then MailChimp came in totally crush them over, you know, a period of ten years by having this massive freemium offer, which is the reason that I want to do what I want to do right now. I just was so dumbfounded by how amazing that was. And get emails, which is no retention on comm started.

00:40:00:20 - 00:40:18:14

It was the end of a three year pursuit of trying to because like that email marketing business got the three millionaire hour and then stopped because if all you're doing is trying to scrape the bread crumbs off of someone else's table and like you're copying them and stuff like that, like it's not going to it just reaches a ceiling very quickly.

00:40:18:18 - 00:40:35:21

And there was a positive and negative that positive was it was a positive cash flow company. The negative is that, it couldn't grow in its own right because MailChimp had this free offer. Like, I remember being at my brother's house over Thanksgiving one year trying to learn about marketing because I thought that, like, marketing would help us grow.

00:40:35:23 - 00:41:05:09

And, I was watching this digital marketer.com video about marketing, and he's like, this is the statement of value card. And it's basically like blank helps blank achieve blank, right. And like there was nothing that I could say about our company that if someone knew about MailChimp, they wouldn't pick MailChimp. Like, it wasn't really any cheaper because like, the weird place you get to in SAS is like you kind of you undercut on raising your prices until, you know, and it's like, whatever.

00:41:05:11 - 00:41:28:18

And for 90% of our companies that were our customers, MailChimp would have been free. So I was like, so dumbfounded by this idea that they had set themselves up. And by the way, like they went freemium when they were 2 million, they are in constant contact was 100 million error. But they created this offer that even the publicly traded 100 millionaire our company couldn't compete with because they couldn't take the short term revenue hit.

00:41:28:20 - 00:41:47:03

Right. And then by the time that they realized there was a threat, it was too late. By the time MailChimp got to like 50 million, there are there was already this, like, virally expanding. You know, they had a great brand and a free offer, and they eventually grabbed 70% of the users in the market and created this massive machine.

00:41:47:03 - 00:42:00:13

So yeah, that was that was the predecessor. And then basically I had heard that it was possible to to get an email address from a website visitor without them filling out a form. I was like, if I could figure out how to do that, I could sell it to anybody and took me a year and a half to figure it out.

00:42:00:13 - 00:42:14:22

Started as a feature and people were using the feature and not using the rest of the app and downloading it and putting in Klaviyo or whatever. And I was like, oh, if I like spin this out, it'll be a good product. If I try to grow the email marketing app that no one wants to use, it's a pretty crappy product.

00:42:14:22 - 00:42:36:07

So I spun it out. It got traction almost immediately, as you saw in, you know, we are here today. And the amazing thing is, is this B2B product has so much more going for it than that did at that time that I was showing you like it just does, you know? So it was basically like the journey to this B2B product was really it was getting emails.

00:42:36:07 - 00:42:55:13

It was retention. You know, it's kind of all been one journey. I like doing it like this. Having positive cash flow businesses that allow you to experiment on other crazy stuff. Right. Like that's my way of doing it now, for sure. I'm just curious though at during really obviously like you're taking this stance now where you're like, hey, I'm building a unicorn in public.

00:42:55:15 - 00:43:32:17

Large ambitions like that. That is a full mindset, right? Where you're like, I'm going for scale here, and we're going to take big risks to do that. Did you have those, you know, same ambitions with Robley or you were like, hey, I'm chill with the $3 million business. Nothing I tried worked. You know, like it was a very weird emotional journey, like until I get emails, which was retention.com, I actually hadn't felt real validated as an entrepreneur because beyond that one strategy we figured out, I hadn't felt creating a product that actually would thrive on its own in the world.

00:43:32:19 - 00:43:49:13

Right? It's. Yeah. So not at all. I didn't have that. I didn't even think it applied to me. And really, what opened that door of thinking that it was possible was sharing an office with the Jasper AI guys for four years. Two years they were stuck at the same place I was with Robley. Then they started that thing.

00:43:49:13 - 00:44:10:19

And in a year, these guys from Maryland. Yeah. That's right. Yeah. And like, I just sat there on the other side of the office and watch these six guys do that. And it became very clear to me that it was not, you know, it was it was possible for me also. Right. Like and I haven't gotten there but like, I don't know, this next thing is a lot closer to that than the last thing was for sure.

00:44:10:21 - 00:44:32:12

How are those guys doing? They're basically ChatGPT is like a direct competitor. Yeah. The thing that they had and the reason that worked so well out of the gates was they had exclusive access to the long form blogging application of OpenAI's GPT three for nine months, and they had an incredible Facebook Demand Gen loop that allowed them to go 0 to 50 million in 12 months.

00:44:32:14 - 00:44:51:00

Now it is much harder for them, as you can imagine. Not the CEO anymore. I don't really, you know, talk to them a ton. You know, I don't share an office with them anymore. But yeah, that was it is not the same environment that it was. Put it that way. Adam, thank you so much. Man.

00:44:51:00 - 00:45:09:23

This was awesome. Really insightful. I think you've got a lot of wisdom, but, let's chat more. I want to tell you, you know, just my team's experience, using the B2B product. Hopefully that can be valuable. Super valuable. That's like the thing I care about more than anything right now. That's how you learn, you know, that's how you.

00:45:09:23 - 00:45:23:15

That's how you build better products. Thanks so much for joining I appreciate it. Yeah. We'll talk shit. Cool. Thanks, Lucas.


EXPLORE SIMILAR CONTENT