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Peep is the founder of CXL, Speero, Wynter and the host of How to Win with Peep Laja podcast. 

Peep’s intro to his podcast says “I don’t do fluff, I don’t do filler, I don’t do emojis” let’s see if we can be friends  

In this episode we discuss:

  1. Is the story the strategy?  
  2. What happens when some idiot hijacks your LinkedIn posts 
  3. The lessons from the How to Win podcast  
  4. Being competitor aware but customer obsessed  
  5. How Wynter was born   
  6. The common mistakes B2B organisations make in messaging  
  7. Being an early mover in a number of markets 
  8. Why CXL was rebranded 
  9. Plans for CXL Live 

Peep Laja

Peep does a lot of thinking about B2B strategy, competing, and winning. After working in software development, marketing and sales, he became an entrepreneur in 2007. 

Peep was mainly focused on general marketing consulting (SEO, PPC, CRO, content marketing), until he specialized in conversion optimization and was recognized as the most influential name in the business back in 2016. Since has focused more on business strategy. 

Since 2011, Peep has built 3 companies: CXL, Speero, Wynter

Find Peep on Twitter, LinkedIn and How To Win podcast  

Book Recommendations

The Road Less Stupid by Keith J Cunningham

JP Castlin’s Strategy in Praxis Substack

Andi Jarvis

If you have any questions or want to talk about anything that was discussed in the show, the best place to get me is on Twitter or LinkedIn

If you don’t get the podcast emailed to you (and a monthly newsletter) you can sign up for it on the Eximo Marketing website. 

Make sure you subscribe to get the podcast every fortnight and if you enjoyed the show, please give it a 5* rating. 

Andi Jarvis, Eximo Marketing. 

Interview Transcript

This transcript has been done automagically using Happy Scribe and hasn’t been checked by a real person, so there may be some hilarious mistakes where the AI can’t work out our accents – I’m sure they’re trained on just the American accent. 

Eyup and welcome to the Strategy Sessions. My name is Andi Jarvis. I’m the host of the show and the strategy director at Eximo Marketing. Today I am joined by Peep Leja. He is the CEO of Winter and will tell us all about what Winter is and how it works. But Peep is this amazing TV where he’s grown companies. He’s been a first move in a lot of markets. He was building websites when most people saw black and white TVs. He’s done some amazing things. This episode came around via LinkedIn. Peep put a proposal that says the story is the strategy of me being a marketing strategist and being, let’s be honest, that guy who likes to pick a fight on LinkedIn. Sometimes I was like, that’s not right. That’s not what a strategy is. I’m gonna tell Peep. I’m going to tell him I think he’s wrong. So I rolled my sleeves up and up. I jumped on when I started tapping on the keyboard and started telling Peep why I thought he was wrong. I may be overplaying this a little bit. I jumped him with a different opinion and a different angle on what I thought, the story of the strategy, where it was wrong, when it was right, that sort of thing. 

But after a couple of comments backwards and forwards, I just sent Peep a LinkedIn DM, I was like, “listen, come on podcast, and we can discuss this because it’s probably a much more nuanced discussion than we’re getting talking on a LinkedIn thread anyway”. And he was like, “yeah, let’s do it” and do what he does, right? So we talk about that. The story is the strategy that’s coming up right at the top of the interview. But then we also discuss his career. And he has such an amazing career, like I said, being a first mover in so many industries. And even the story of how Winter came about, just fantastic. So dive in and have a listen. And we also talk about something right at the end that’s really close to my heart, which is events and in person events being superior to online events. Listen, that is the hill I am willing to die on, right? I will fight anyone who tells me that online event is better than an in person event. It’s just not right. It’s about meeting. It’s about people. It’s about energy. It’s about all sorts of things. It’s not just the content from the stage. 

And Peep, we are connected in the soul when it comes to this. So, right, enough of me waffling about this episode. Just tune in and carry on listening, right? So here comes Peep. Peep, how are you doing? 

I’m kicking ass, men. How are you? 

I’m top of the world. Thank you very much. And thank you for coming on the podcast, because my first interaction with you is one of those classic Internet moments. You put up a post on LinkedIn that I disagreed with and I was the guy who jumped in the comments going, pep, I disagree with what you’ve said. So thank you for coming on to tell me why I’m wrong as well. 

Pleasure is all mine. 

So let’s start with that post where I jumped in 2ft first. There was a line in the post. I think the headline of it was the story is the strategy. And I jumped in and I was like, no, that’s not right. That’s not right. So talk to us about that post and kind of what was behind it and why the story is the strategy. 

Yeah, so obviously, if we define what is a strategy, the definition is not it’s a story, right? But if we break a strategy down into components, whatever framework you want to follow, there’s always the winning aspiration part, like the shared understanding of success, like, where are we going? What are we trying to do to begin with? And so this really can be and should be a story. What are we building? And the story you decide to tell to the market really informs a lot of your product strategy decisions, marketing strategy decisions and et cetera. So let’s say let’s take a different example. So if I’m building the hotel chain, Ritz Carlton, and they’ve grown tremendously over the last 20 years, they were a no name in the it’s a big name in the luxury hotel space. So they’re telling the story of huge commitment to excellence and devotion. And of course, I’m using my own words here, I don’t know how they exactly phrase it and then how you deserve it and the very best still exists and all these things that’s the overarching story of that you deserve luxury and the very best. And so the whole company gets aligned around the story. 

I know what we are, what are we about and all that stuff. And now when we make product decisions in terms of what is a cheque in process, like to the hotel or what is like, they have this thing where every person at Ritz Carlton, let’s say it’s a gardener should be able to solve every problem. Oh, the sheets on my bed were not changed. You tell the gardener, and the gardener says, I’m very sorry, I will fix it right away. And they can, and they will. Just as an example, what it also does is, for instance, Zora, the subscription billing company they tacked onto this story of the world, is going into a subscription economy. So don’t just get customers, get subscribers. Everything is going in on a subscription model basis. And they started telling the story in like 2009 or something where nobody even believed that story. This is the overall story. And now when there are salespeople, for instance, hedge Laura and sales meetings, the subscription economy story sets the context for the features. It’s not like, oh, you can do this thing with Laura. It’s more like, do you want to join the subscription economy and play a role. 

And then, of course, there’s always that the winners in this today, pursuing this strategy of joining the subscription economy are doing this. Losers are sticking with the old ways. And so you create winners and losers. There’s a split. And if you want to join the winners, here are the things you need to implement, let’s say. And then now it’s like, oh, well, Zora enables you to do this and that and that, and so it creates context, a winning aspiration. And really it’s a leadership tool inside the company to rally everybody around the same cost. So TLDR is part of the winning aspiration? 

Yes. The Ritz Carlton, when I do presentations, I talk about them a lot. They used to I don’t know if it still is, but they used to have a brilliant mission statement, which was, we are ladies and gentlemen, serving ladies and gentlemen. Have they been? 

Exactly. And the CEO wrote an excellent book about how they did it and how every person that works for Scotland and buys into that mission. And there’s the story. And they open this new hotel in Jamaica and all these people that applied to work there had never, ever worked at a hotel before. And the first day of opening up a new hotel, they show up in the very best clothing, like going to a wedding or something, or the Queen of England is coming to for a visit, and then the CEO of Rich Carlton is like, well, hey, we have uniforms, so why are you dressed up like super fancy? Well, because we are the ladies and gentlemen here. Well, that makes sense. 

Okay. Buy in. The way they drive it through the whole organisation is fantastic. Right. It’s really good to see. And it’s one of the examples, I think, of that mission statement being used properly. And there’s so many vague and terrible mission statements. Right. That’s one of the ones that always sticks in my head and I really love it. 

Exactly. And I think the story is a better mission format for a mission statement. What are we trying to do here? We’re not trying to make the world CO2 neutral or whatever. That’s kind of a boring one liner, but rather, if you tell a story of what’s happening, what’s the change the climate, blah, blah, it’s a more impactful thing. People buy into it. 

And I think as people, as humans. And I love about the line, the stories, the strategy, that people remember stories, they remember that narrative. And some people claim, oh, look, we’ve been telling stories since caveman days. Right? And that’s why stories stick with us. I don’t know if that’s true. Right. I’m not an anthropologist, but I know people remember stories. We passed them down through generations. Oral storytelling traditions. 

Absolutely. I read a lot of books. Five years later. I forget about what the thing was. But I remember the examples. Like the stories of how somebody did something. 

The Grim brothers. You don’t remember sort of how many percentage of the three little piggies didn’t get something or whatever. You just remember the story and stories get enhanced and embellished and we remember them and it brings us to life and it presses our button. So I love it’s a way of communicating it. And I think the problem with a lot of strategy is that it sits at Csuite level in the boardroom, doesn’t drive down through the organisation like Ritz Carlton did with it, and therefore there’s a disconnect between you end up with this strategy and execution, like it’s two separate things. 

Exactly. And it’s written in this boring business jargon language and then it’s going to live on your Google Drive and never look at it, or hopefully the management is better than that. 

Yeah. But then what you do is you have another off site, you call a consultant, I come in or someone else comes in, we charge you a great fee, we come away three days later, waving a bit of paper around and go, yes, look, we’ve got another strategy. I do the same things over and over again and business as usual carries on. I am absolutely on the page. If you’ve got a story, you can tell a rallying cry or whatever you want to call it. North Star, it doesn’t matter what you call it. 


You have a story you can tell the board, you have a story you can tell the organisation, you give them a cause to get behind. 

Exactly. And when companies are confused about what should our North Star metric be, if you’re aligned around the same story, it becomes so much easier to agree on those key metrics. 

Yeah. And then you start at the top and work your way down. So this is the story and these are the things we’re working on. So you might be listening to this now, thinking, OK, well, why was Anti climbing into this post then and going, Well, I disagree with you, I disagree with you. If you’re both in complete agreement, the story is really important. So to me, where I came from, from a disagreement perspective, was we had a guest on the podcast maybe a year ago called JP Castle in who. 

I know him. 

You know JP, right. So JP’s brilliant. He was a lawyer and he’s probably more of a business consultant. 

I love his substance. It’s the best newsletter out there. 

So I’ll put a link in the show notes. If you don’t get JP’s weekly email, it is incredible. And pay for the extra bits, because that’s definitely worth having. And JP 1015 percent commission lifetime will be great. Thank you very much. If you listen. But JP wrote a piece in Marketing Week where he talked about his frustration between the law, where a legal term has a very precise definition, and marketing, where no term has a precise definition. So when I say strategy and what someone else has a strategy could well be two different things. And one of the exercises I do with my clients a lot of the time, we want you to come in and help us write a marketing strategy. The first thing we do is like, what do you mean by a marketing strategy? Because to some people, they just mean a plan, some people mean a collection of tactics, some people mean the thing I would call the strategy, and some people sit around and go, Listen, I don’t really know. Right. We just think we need a strategy. 

Yeah, totally. For sure. There are all these strategy framework, like if you want to do the playing to win, roger Martin or the Gustrategy Pass strategy, Remote or Kathleen Zone, ABCD, they all have some form of winning aspiration whatever it might be called. Right? Yeah. 

So they all have that story bit in them. And the bit I had with your post is that people are going to look at this and go, right, if we nail the story, we’ve nailed the strategy. Yes. And that almost was the bit that sort of set me go, right, I must tell Peep that he’s wrong, because it feels like there’s such a misunderstanding of what strategy is to so many people that if you feel and nailed the story, that’s it, everything else goes away. And I’m like, no. 

Right, right. That’s the challenge with social media is because I’m a frequent poster on LinkedIn, twitter is a strategic play for me. I talk about strategy often a lot, and so I assume a lot of my readers have been following me for a long time. So focusing on a single post is kind of like taking things out of context. We did you see what I wrote about two weeks ago? 

You have an audience, right? And you talk to your audience, and we do we’re talking sound bites. Not sound bites, but we’re talking in single posts, and there is a body of work there, and you’ve got a podcast as well, which has another kind of layer to the information that you share. It is an interesting point that you say with social posts that we do take them out of context. I took yours out of context. 

Right, for sure. 

It’s a funny medium for that, isn’t it, social, where every individual that stands on its own, but he’s also part of a collective yes. 

And also there’s limited space in terms of character count and also in terms of how much shit people are willing to read on social media. So obviously you’re going to have to leave stuff out. You can’t like it’s not like a 700 page textbook where, like, you define everything very carefully. I’m not optimising at all to cover every use case, every age case. Is this what I said? Correct. When this happens, in fact, in social media. If you want to be controversial or call out the haters, it’s actually good for you for your post reach, right, yeah. 

Although hopefully Facebook is on the other end of this at the moment, where they’ve been riding the storm of negativity for so long that it seems to now be affecting their active user base. But that’s probably a different discussion for a different day, isn’t it? Sort of podcast, but beyond your post as the algorithm works. I’ve engaged with a couple of your posts because I had a little disagreement and then saw the rest of your content, which introduced me to your podcast as well, which is a delight. Right. The production values are way higher than the strategy sessions and it’s a great lesson. 30 minutes. Beat the B SaaS leaders giving some great lessons. It’s called how to win. How long have you been going out the podcast then? And are you enjoying the hosting journey? 

I’ve been doing this little over a year now and I’ve been a content creator for as long as I can remember. My main medium always used to be writing. I built my first company and my name in blogosphere writing blog posts, and so now, recently it’s Twitter and LinkedIn, my main mediums, because I don’t have time to write blog list anymore. But I always wanted to do a podcast and what held me back for the longest time was I didn’t want to do yet another podcast because whatever medium it is, there’s so much of everything out there. So I wanted to have something unique and unique format, the unique perspective. When I launched the podcast, actually, I record, I had three concepts in mind and I recorded episodes for each of these different concepts and then while recording it, I felt, oh, this one actually has legs and I enjoy doing it. And the format kind of flows and these other episodes with other formats, I just discarded them. Even though I recorded them, I never used them. I’ve been having fun, so I mainly do it because I’m actually interested in the subject matter, how to grow companies, what separates winners from losers, and relationship building aspect of it. 

I found podcasting, it just felt like a natural home, right. If anyone who has ever met me alone, I love talking, right? It just felt like a natural conversational medium for me and it took me forever to write a blog and it felt painful, but I could sit and. 

Talk to people forever, so it just. 

Felt like a really natural home. And you get to meet great guests like you. 


So the podcast is called how to Win. There’s a link in the show notes if you want to go and find it, and the first thing I want to pick you up on is in your introduction, he says, I don’t do fluff, I don’t do filler, I don’t do emojis. It’s the last bit that worries me. I’m not sure if me and you can be friends now. 

Well, I actually do a little bit of emojis, but it just sounds cool. 

It’s a great introduction. But you’re then looking at is it strategy? Is it look, how do these companies that do well with over the years that you’ve been doing it, what are the kind of key themes that keep coming again and again from the companies who are winning? What are you learning? 

Yeah, so let’s start with what’s luck? And actually between you and me, I’ve recorded multiple founder CEO interviews for the show, where I did not publish the interview because the founder CEO had no clue, there was no strategy. They stumbled into success. And so their luck is a real thing. Yeah, examples are like you start a company at a time when something in the external world happen that needs your service. So, COVID happened, there was a massive boom in ecommerce. And so if you study the SMS service for ecommerce companies around 2020, you were in great luck. And so this company grew. And if you try to understand, what did you do differently? What was the strategic thinking and competitive? Nothing. We’re just here. So luck plays a role. And that actually is also how these big winning companies are winning. The inevitable component is that you need to tap into existing demand. There needs to be demand for your product. And the bigger the market, the bigger the demand, the faster you will grow. And of course, if you’re early to a market that is about to explode, like e commerce, you’re in Kuvid. 

That’s great timing. That’s great luck. Or another thing that companies like Deal and Oyster and so on, that enable you to hire full time employees all over the world and take care of the taxes, payroll, compliance. Those companies got really big, like from zero to 100 million in one, two years just because of the lack of timing, because suddenly the whole world needed it. So that is, I want to say, number one thing is like a lot of people need what you do and hopefully you’re early to the market and then there’s a lot of empty space until number two reason comes in. 

Can I jump in and talk? Because I was asked by a group of students about how lucky you have to be to do well in business. Right. And I thought about it for a little bit, and I’m back. I think the things that some people pass off as look and not look because it’s easier to put it down to look then other things. So you mentioned, like I said, the company that built Oyster, I don’t know them, but you know, they built remote working compliance, taxes, payroll, that sort. And you look at it and yeah, look, the timing is look, they launched at the right time. But I say to people who’ve done it, I’m like, well, you’ve got maybe 20 years in your career of working in this industry that wasn’t look, you decided to leave your job to build this company. That wasn’t luck, that was brave. Now, the timing element may have been luck, but there’s 20 years of work gone in to getting lucky. And was it a golfer who said, the harder work, the luckier I get, or something like that? Are we attributing things to look that are actually maybe more? 

Well, there is an element of I. 

See what you’re saying. So obviously there’s like, even if you have the best opportunity, you can squander it or squander it and execution needs to be top notch and all that stuff, for sure. Timing still matters. What you design, your business does can be a point of lock. And let me tell you a story. So, friends of mine here in Austin, they built this company called Proof, which is kind of like the social media widget. When people on your website, they say, hey, Johnny from Birmingham just bought this bag and 22 other people are looking at it like ecommerce widget, they got somewhere. And then they built like a B testing personalization tool, very late entry to the very crowded market. And that tool never went anywhere. I mean, they made some money, but it was like stuck at low revenue. And the founder is telling me, like, I don’t know, man, we’re like, we’re smart people, why aren’t we getting more luck? Why aren’t we making more money? And they went to Y Combinator and all that stuff, and then they decided to just abandon ship and build a whole new product. And then OpenAI announced GTP Three, this new thing. 

And so they immediately, like, day one, hopped on that opportunity, let’s build something in this new space. And they built a company that’s now called Jasper AI. Basically went from struggling for years to insanely successful, raking in millions, left and right type of company. Opportunity timing, you know, so you can totally be super talented, skilled, experienced by working on the wrong thing. 

Yeah. And focused in the wrong place. There’s probably a different discussion there to get into it. And I’ve seen you talk about this as well on social, about knowing when to leave something behind so you can focus on something else. As a CEO of a company, and you’ve had a few companies, we’ll talk about them probably as we go through the discussion. But how do you know when to leave something behind, when to bail out and to start something new? Because the emotional investment, the financial investment, the time investment, for sure, companies, how do you know when to leave? 

Yeah. So some cost fallacy will keep you stuck. And also the emotional labour that all the hard work you’ve put in that will hold you back. So you’ve got to be aware that these biases are affecting you. Like change. Start from awareness, but then really, it’s like you need to be honest. How much money do you think your company should be making? And you can look at benchmarks, like if it’s your year seven and you haven’t broken 1 million in revenue for, let’s say, a SAS business, dude, this is not happening. Of course there are age cases where this has happened. Like UI passed, I think, ten years for the first million, and now they’re like decor or something. So it has happened, but the odds are very bad. So I want to say, like, look at it from a purely financial perspective. How much money are you making, what’s your growth rate? So back in 2009 or whatever, I studied a SaaS company called Train Them, which was like build your own course platform, kind of like what Teachable is Today or thinkific. And we got to, I want to say maybe to like ten k, MRR. 

Revenue Level. And then the growth was like eleven k, and then the next month it was maybe twelve k, and then dropped back down to ten k. It was like zombie territory. Not quite alive, but we’re not quite dead, but not quite alive either. And so after two years, I was like, we’re still making ten K a month. I mean, I have better things to do. And as soon as I decided to kill the business, which should have done it way earlier, because for all these emotional reasons, I delayed and I started my next business, CXL, the success was instantly way better. Like, I was working on things that had more demand. It was just a better business, better timing, all that stuff. 

I think it’s that emotional investment and it’s probably the easiest person to lie to is yourself, I think. Oh yeah, sometimes they go, maybe because if I fix this or just around this corner, maybe if I change that, epiphany that, and also, let’s say failed. 

Startup founders when they’re trying to sell off their assets, like, okay, I’m going to have to abandon this, but I’m going to see try to if I can recover something right. And they try to sell after failing SaaS business, and often they don’t value the business the way business is valid. Like in SAS, it would be a multiple on your revenue based on your growth rate and whatever they say, well, I think my developers put in 1000 hours, so let’s calculate hourly. They do that kind of math. Oh, yeah, you can buy for $20 million, so you know, whatever it is. Well, your business only makes ten K a month, so I’ll buy it for 200. 

Yeah. The illusions and the delusions of it that you tell yourself about business is always a tough one, isn’t it? 

Always a tough for sure, yeah. How much sweat equity you put into something means nothing at all. 

Yeah, there’s very little value, especially if you’re trying to sell it as a fire sale. There’s definitely no value to sweat. 

Nobody cares. 

I’m going to throw another line at you from the podcast from An Sandwell. He said something along the lines of be competitor aware, but customer obsessed. And I wrote it down because I was like, I love this. Right. I often say to customers, stop copying your competitors. They don’t know what they’re doing either, right? 


So many companies are just hyper focused on what the competition doing. Forget to look at what the customers are telling. And he said, I was like, Jesus, guy, I love this. What do you make of that line? And what did you make of Anandeem Is? Brilliant. 

Yeah. Well, here’s an example of a company they pivoted at 8 million arr or thereabouts. And now they are, I think, over a hundred. Imagine the guts to change what you’re doing at around 8 million a year. This would be a dream revenue for a lot of, like, setups. But they pivoted. They abandoned the old ship and built a new one about the line. Yeah. So if you look at any business category, especially tech, like, sameness is pervasive. Like, every competitor looks like just like the next competitor. And why is it? I mean, A is because they’re all looking at the competitor. They have that feature. We also need that feature. Right. So it’s this constantly copying each other. And the thing is, if you don’t have a brand vision, like, you don’t have a strong identity story of what you’re building. You want to be customer obsessed. And then you do everything that the customers tell you. So there’s this famous story of how Tesla did focus groups with moms for their Model X, and like, hey, what do you want about a family car when you drive your kids around? And the things that they learned about what moms want from cars was identical to what Toyota found out when they’re interviewing moms for their Toyota Sienna minivan. 

So both good now they have the exact same insights. They could build the exact same car because they all want the same thing. So it’s like, yes, listen to the customer. And of course you want to be customer obsessed, but you have to have your own vision, too, otherwise you’re going to end up building the exact same thing. And I think if three startups would start today in the exact same space, but they wouldn’t be able to look at what everybody else is doing, what the competitors are doing, they would build wildly different companies, I think. 

Yeah. So, having said, I’m not an anthropologist. Right? There’s actually some anthropological evidence of what you’ve said there. So in Australia, Tasmania drifted away from the mainland over a period of time. 


Tectonic movements don’t happen quickly, but the aboriginal tribes of Tasmania became cut off from their ancestors on the mainland, which actually gave anthropologists and let’s not get into the ethics of the great white anthropologists who. Went over there and studied Aborigines, not in very ethical ways, right. But what it gave them a great case study of what happens when stuff goes off in different directions. So they effectively were the same people separated by water, but they had no interaction with each other and ended up developing. The Tasmanian Aboriginal population is really different in lots of ways to every other Aboriginal population on the island of Australia because they had no interaction with them at all. And it’s almost you take that to a business point, if you stop looking at what’s going on around your competitors, you would go off in a very different direction. Definitely end up going differently. 

Totally. I have these discussions all the time inside my team, where team, of course you want to be competitive aware, so they say, oh, like they are doing it that way. I looked at these competitors, this is the way they do it. And I often say, like, I don’t give a shit the way they do it. We have our own model here, we have our own thing going on here. You can, of course take inspiration from if there’s obviously a better idea. And the way you do things is objectively worse. Sure, you want to change course, there’s a time and place, but like, also human beings we’re made to copy as children. We mimic the parents and like, this is how we learn to walk and talk and also, like DNA. By definition, we’re the copies of people that came before us. The copying is very natural behaviour. We just get a resistant, which actually. 

Gets us nicely into winter. Because I think with winter I’m looking out my window and island here and winter has definitely come when we’ve been on this podcast, it’s gone from bright sun to annoyingly heavy rain. But Winter is in your company, WYNC, which is messaging for B to B companies. And I think I want to kind of throw this out because I think what you’re saying, there’s a lot of sameness in the industry, in products particularly, where copying features is relatively easy. So messaging is the one place that you can stand out, right? They can’t copy your story, they can’t copy your message. Well, they can, but they can’t do it as well. Is that where winter comes in? Helping companies find that space to be able to communicate better with their customers? 

Yeah. So there are two aspects to it. The purpose of a business is to create a customer. In other words, without customers, there’s no business. And the only way you do it is by sending some sort of messaging out for the customers through whatever medium it is in person, email, sales, website, it doesn’t matter. And to get more customers, you need your messaging to improve. So it’s more compelling, more clear, et cetera, et cetera. So it’s immensely powerful tool, if you want to call it that. Yet until recently, there was no way to measure how effective these are. Messaging using web analytics, we can measure every click, every scroll on our websites, but no clue how the words are working. Like what’s confusing, what’s unclear, what needs improvement, what’s actually turning people off? No clue. And so I had this very problem at my previous company, CXL, where hundreds of sales pages and I was asking myself if my ideal customer is reading this sales pitch, are they like, wow, this is amazing. Or are they like, who cares? What’s interesting? What’s boring? And so I was like, wow, how is it possible that this problem has not been solved yet? 

And so I jumped on this opportunity and yes. So with Winter, you can find out two things a what does your target customer once think? What are their pain points, challenges, priorities, desired gains? And B you learn when your ideal customer reads your sales page on your website or wherever, what do they think of it? What did they find compelling and what did they find off putting? And all these other things. 

I often refer to B to B as boring to boring, right. Not business boring to boring. Because BTB, companies love talking product features. Our product is this and the prospects sitting at their end going, I don’t give a shit. Right? So be to be boring and boring marketing. Is that one of the common problems you see, that people just blind you with features? Or is that the sort of thing that you’re helping them fix? 

Or is it yeah, I want to say that, yes, it is very feature focused. However, I don’t think it’s necessarily a bad thing because also the prospective customer does want to find out what is this tool? They do want to know the features. The biggest problem is by far is clarity. The prospect comes on the website, they read it and they still have no clue what this business does because they use like jargon and fancy buzzwords and they go into selling the benefits right away. People no, I don’t even understand what it is because they’ve completely dropped communicating their positioning, which should be the first thing you say and you’re above the fault. Like, what is this and who is it for and what does it enable you to do? 

This is a frustration for me. With SaaS products, you go on the website and it’ll say something like we revolutionised communication for B to B OG. And you’re like, but then the only other thing you can see to click on the pages start your free trial now. I’m like free trial. 

What? Yeah, exactly. 

The trial. I don’t even know what you do yet and you can try to sell to me. 

Exactly. Because that pitch was probably made originally for the VCs who were bedazzled by the big grand vision revolutionising an industry or big Tam. That’s great. But your customer is different and a lot of times. Of course. The messaging on the home page is very political internally. And a lot of times it’s the brainchild of the CMO or CEO who are very protective of their children now. But also at the same time. These people are rational actors and probably very smart people. And they would change their mind about what the home page copy needs to say if they only had data on how it lands on the intended recipient. And if they would have data that your target customers have no fucking idea what’s going on, it would change. And that’s a big thing that Winter gives, is this data on how your messaging lands and it helps create internal alignment of what we should say instead of the times. There’s a lot of infinite product wants to say this, marketing wants to say that CEO has another idea, SDRs want to use other messaging. So there’s no consistency or maybe there’s just a lot of fighting. 

Yeah. So you’re bringing the data to the argument so that you can start to make better decisions because of that. 

You’re exactly right. Yeah. 

There’s an element here though, with Winter that you are like you said, you saw a problem that couldn’t be solved. No, sorry, let me rephrase that. You saw a problem that hadn’t been solved, so you build Winter. Not even solved because you’ve solved it. So you built winter? So you were right at the beginning, right at the early days of this industry of solving that problem. Looking back through your CV, there’s maybe a couple of other things you’ve done that you were a web developer in 2002 when most people weren’t really the internet is not what it is now. Right? And there’s probably a lot of listeners of this podcast, it might not even be born in 2002 who just don’t quite understand, but it really wasn’t the same as it is now. And you also started CXL as a conversion optimization agency in 2011, which was certainly in the Stone Age of that industry as well. Do you just love getting in at the beginning, getting into the ground floor and building the sector? Is that your thing? Are you a forward thinker or do you just look for the opportunity to go in and go, this is unplowed land, I want to get in there. 

It’s a bit of luck. And at an early, young age I wasn’t conscious of this and I was just interested in computers and the web is new hot thing, that was cool and so on. So I became web developer. Conversion optimization thing was actually it came about, I was like a marketing consultant, like all purpose, I do SEO, PPC, this and that. But I realised that I need to pick a niche because all purpose, being a generalist, is a road to nowhere already. Back in 2011, it seemed like the internet is crowded and of course, little did I know. Yeah, I mean, like, in SEO, rand Fishkin was already big, and SEO maas, I guess. 

SEO, yeah. 

And so I was like, okay, so I need to, like, should I go into SEO now? That seems too crowded. Should I go into PPC? Seems too crowded. And the way I measured it was number of agencies doing it, and also how many blogs were out there and were they any good? And then I looked at CRO conversion optimization. I was like, well, very few players that I can see, and their blog posts are crap. It’s like, very mediocre. I was like, I can dominate this. And so I decided to just based on that, to just focus on zero. And sure enough, we dominated the hell out of it. Conversion Excel was the company now called CXL, and we dominated the search engine rankings with our blog posts because nobody else was really doubling down on content marketing back then. And we blogged like our life depended on it, and sure enough became the kings of that universe. Yeah. 

And CXL rebranded at some point in its lifetime to spiral spiro what was behind the rebrand, because Conversion Excel seems like a great name for it. Was there kind of internal pushing behind that? 

So things happened where we started this Conversion Excel, and then maybe three, four years after we launched, we added on a conference called Conversion Excel Live. And that’s a mouthful. Conversion Excel is already a long word, and we started noticing that people themselves started to abbreviate Conversion Excel as CXL. And then maybe five years into the agency, I personally got tired of consulting. And it’s like, well, what else can I do in this business if I don’t want to be? And I was like, the cover boy. People wanted to work with me. I was a name people knew. And then we surveyed our email list, which was pretty sizable at a time like hundred thousand people or something, and basically asking them, like, what else would you want to buy from us if we were smart enough to sell it to you? And they said, like, courses and ebooks and things like that. And so I decided to build, like, a branch of the business that we called Conversion Excel Institute. Another mouthful as a sub branch. So there’s agency and there’s content business, and the content business, I mean, year one, I think we made $250,000. 

In year two, we made a million bucks. And it’s like, wow, this is going places, right? Success is fast. Especially thinking back to my SAS company that never got past ten K a month revenue. And then fast forward, like, when we have Conversion Excel Institute and so on, it was like, this is like, too long. So we changed Conversion Excel CXL just it will be shorter to say. But then around 2024 years into the content business or the learning business, we ran into this problem where our company was doing two separate things, agency services as well as Elearning business. And it’s very hard for a company to stand for two different ideas like what are we? And some people thought we were only agency and some people knew us as only Elearning. It was confusing. And so we decided to also basically cut it in half and spin one of them out. And we decided to spin the agency, even though that was original business, into a separate brand. And the reason was that most of the email list of 100,000 something people, they would rather buy the down market product, the subscription to our content, rather than an agency, which is like 20,000 a month type of thing. 

And so hence we let the new Elearning business inherit all that. 

Got you. So there’s got a lot of thought going to it then. Great. I love the stories of rebrands as to and some of them, like you were saying about the things you learned from me, I guess some of them are like, actually we don’t like this anymore. And some of them are built around solving real problems for the business. Which is where yours is going. 

Totally. And also if I think about the long term and possible exit scenarios in the future, not that I’m fishing for it, who will want to buy a business that is both Elearning or an agency, right? Maybe nobody or very few. But there are companies that by agencies, there are companies that buy Elearning businesses. Right. So also that played a kind of a role in my decision making, like thinking ten years into the future or. 

Whatever, and you still got the live event taking place, which is coming back fairly soon after a covered break. When is that? October time it’s taking place? 

Yeah, it’s like the last week of October. October 20 526. Eleven in Austin, Texas. 

Excellent. Now that’s quite a trip to make from Belfast, Northern Ireland. So I probably won’t be coming, but you said something about how magical it is to have people coming back into events, which is something close to my heart. I did endless events on Zoom and Teams or whatever across but I’m back to conference speaking. I was out in Philadelphia recently and go to Macedonia next week. This is great, being back at events in rooms with people. There’s something about it that is just magical, isn’t it? 

Totally. I mean, you don’t travel to in person events for content because that’s going to be all on YouTube anyway. It’s silly to pay the flight and the hotel and the ticket to the event. I went to SASR a couple of weeks ago. Now, I didn’t see a single talk, maybe one over three days. That’s not what live events are about. Live events are about relationships. So chatting up with people you already know, like deepening your existing relationship and building new ones and you can’t do that online. I mean, it’s very, very hard. And of like, don’t even get decided with virtual events that they do zero for relationship building. Zero. It’s an effective medium for content, not for relationships. I’m a huge believer in relationships. I’ve built my businesses on top of relationships. That’s how I make most of my money still. 

Yeah, exactly. Virtual relationships were virtual conferences were a necessary evil during COVID. Right. There was a crush for the organisations to keep those businesses going. But even the ones I went to where I was presenting, or ones where I went to when I was just attending, the way that they tried all sorts of things to create that networking just didn’t work, did it? 

Nobody tried. 

So to be back in person is great. This show will be out before then. So if anyone is in or near Austin, Texas, what’s the website? I’ll put it in the Show Notes. 

Obviously, so people can yeah, Live. Perfect. 

We show that and hopefully get that promotion. We are coming towards the end of the the top of the hour where we wrap up and let you get back to running a business. So what I have is a couple of different questions just to wrap up with. So my first question is about books or reading or podcasts or with plug yours anyway, but where do you go? What books do you read or what recommendations would you give people to kind of stay up to date? 

Yeah, I mean, I read books based on like, what problem am I thinking about today? What I think I could use help with. So if I had to recommend one lesser known book that any business owner would benefit from a lot, it’s called Road Less Stupid by Keith Cunningham. It will blow your mind. I especially recommend the audio book. The author narrative, Roadless Stupid is so good bye. 

What was the guy’s name again? 

Sorry. Keith Cunningham. 

Keith Cunningham. 


I’ll write that down. I’ll get that in the Show notes. It sounds like a great book as well. Even just in the title, I’m like, let’s get that old. 

The TLDR is like, entrepreneurs pay a lot of stupid tax for making stupid mistakes that could be avoidable. And so this book is about basically how to run your business without paying the stupid tax. 

Yeah, that definitely feels like it’s got a window into my soul. Listen, thank you very much for your time. It’s been great to hear from you. It’s been great to chat and to find out a little bit more about what you do. And it’s been a pleasure to share some time with you. Thank you. 

Thank you, Andi