Bootstrapping & Messaging: Peep Laja on growing CXL & Wynter

October 2, 2023

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Episode Summary

In 2011, Peep Laja founded CXL, a conversion optimization agency that eventually rebranded as Speero, before CXL was spun off as a marketing training company.

After serving as CXL's CEO for 12 years, Peep founded Wynter — a platform that lets you test your B2B messaging with your target audience — and has grown it to over $2M in annual revenue.

Peep Laja is an expert at bootstrapping companies.

He started by turning his in-house marketing experience into a consultancy…

He took that consultancy and scaled it into an agency…

He used the profits from his agency to bootstrap an e-learning business…

And then he took the profits from his elearning business to bootstrap a SaaS company.

In today’s episode, Peep and I discuss:

  • The founding stories behind his three companies
  • Advice for company positioning and messaging
  • Why he moves upmarket as fast as possible
  • Wynter’s growth and marketing strategy

Links and References


Founding & Evolving CXL

Alex Kracov: So let's start with your decision to create CXL. I believe CXL was initially a blog around conversion optimization. Can you talk about the origin story?

Peep Laja: I had just shut down a startup that failed. I had a bootstrap startup that I tried to grow for two years. I ran out of ideas how to change its luck. Basically, it was a zombie company. Not quite dead but not quite alive either. So I killed it. It's like, okay. How do I make money? I was like, okay, I was already earning income as a marketing consultant. So I built a blog to build an audience. That was my intention: to build an audience, email list. So I would create, let's say, a lead gen funnel for my services. Then it started working quite fast. This was 2011. LinkedIn was nothing. So it was all about blogging. I blogged like my life depended on it. Even one year, I developed a significant audience. Significant enough so I could hire a designer, a developer, and a project manager. I started a little agency.

Alex Kracov: Was that always your intention, to start an agency? Did you start the blog with the intention, okay, I'm going to build an audience, and I'm going to spin this off into an agency?

Peep Laja: Yeah, exactly. As I said, I was already like a freelance marketing consultant. I was good at my craft. I didn't want to do the deadlines and stuff. So I needed a project manager, and you always need design and development. And so I thought, okay, I'm going to just be the face. Then these guys will do the behind-the-scenes work, and it will be easy. I mean, nothing is ever easy. The easy part didn't work out. The agency did.

Alex Kracov: And so what does a conversion optimization agency actually look like? I assume you're helping people craft their landing pages and get button copyright and messaging. I don't know. What are the day-to-day projects usually look like?

Peep Laja: Of course, what the agency is today, today it's called Speero. It's still around. It's doing great. Today, Speero is very different from what it was when I started it. When I started it, the premise was like, hey, we'll make your website convert better. Basically, we took your WordPress website, changed the design, changed the copy, changed some UX flows, made it easier, lowered friction to take action and tried to increase motivation to take action. It was project-based. We were targeting SMBs because that was our audience. We're very cheap. I think we were charging, just for optimizations, $400 a month. Redesigns were like maybe $3,000, $4000. Like peanuts, nothing. Today it's like 20k-a-month deals.

Over time, we went up market. Because what we learned is that big companies, small companies, the amount of work that goes in is the same. Except if you increase their sales by 5%, a small company that makes a million dollars a year, they're like, "Dude, you rip me off. F*ck you." A big company that makes 100 million a year is like, "Oh, my god. 5%? Woohoo. Ferraris." So they're very happy with you, and they're not negotiating over the fees. So over time, we went up market. And of course, our own understanding about what business we are in changed. It went from increasing just a conversion rate metric to building experimentation programs in large enterprises.

Alex Kracov: Yeah, the ICP point you make there is so interesting and important. It's something I'm thinking a lot about at Dock. Because we have a lot of really small businesses sign up to use it, but they demand a lot of support and stuff. When you share pricing with them, they're like, "Oh, my God. This is so expensive." But then you go talk to mid-market enterprise companies, they don't even blink at the cost. It's the same work, right? Even more work.

Peep Laja: Exactly. And in SMBs, typically, the boss is the founder who often considers any company's cost be their own money. It's like, they treat it as it's their personal money. They feel like you're robbing them. Worse, if it's a mid-market company, it's virtual money, right? It's like line item in a spreadsheet. There's no emotional attachment, so it's easier to spend.

Alex Kracov: Yeah, way less personal. That's a really interesting way to put it. I do feel like that. Even as I spend my own money at Dock, it's like each dollar is just a little less of my runway and a little less of my future. It better go to someplace worthwhile.

Peep Laja: So anybody who was in services businesses especially, my advice is always just do not work with small businesses. Go up market as fast as you can. Of course, as fast as you can is not like two months. It will take years. It will take years. But start making progress that way. Also, if you have never worked with large businesses, there's a learning curve how to pitch them, how to service them, what they need, what they want, how they think. It's very different.

Alex Kracov: Yeah, when you get to start dealing with procurement, and I got to do site too and all that fun stuff. Running agency is a pretty hard business, right? You always either have too many people and not enough clients, or too many clients and not enough people. How did you sort of think about building this agency side of the business and that constant problem?

Peep Laja: Yeah, it is a low-margin business. 20% is excellent margin in services. The best of the best have 30%. 10% is fairly typical. I'm not a spreadsheet very analytical type of guy. I'm more like a big picture. Let's sell and market hard. So I kind of winged it which is, I think, how a lot of entrepreneurs tend to do it. Well, it depends on your strengths. I'm not a spreadsheet guy. So it was like, the revenue was going up. I was like, yeah, this is working. Let's do more of them. Let's do more of this. For us, what was working was just content marketing. We were getting more leads. Or, if we can't take on more clients because we have no - essentially, we're still selling time no matter how you charge for it. We need to hire more people.

Today, of course, the agency, which is now 12 years old, is much more mature about this stuff. But still, these constraints happen. We know that in our pipeline, we have, let's say, seven hot deals. Do I appropriately service them? We don't have enough people, so we need to start hiring now in advance even though we haven't maybe signed these contracts yet. Maybe they will fall through in the last minute, and then we have over hired. It's tricky.

Alex Kracov: Then eventually, you build an e-learning business on top of the agency. Then, as you said, the agency is now Speero and still alive and kicking and doing really well. I think the e-learning is still called CXL, right?

Peep Laja: Right.

Alex Kracov: And so why did you decide to go build an e-learning business on top of the agency?

Peep Laja: So why build another business on top? I had two reasons. One was a personal reason, and one was just obvious business reason. The obvious business reason was that as our blog, which was a lead gen mechanism, grew more popular - getting 300,000 visits a month, email list of more than 100,000 people. This is around 2016 - most people in our email list, email list of 100,000 people, 99 point something percent of people would never be able to afford us. Because back then, we were already like 15k a month retainers. So it's like, okay. So we have all this audience that we're just not monetizing.

And so we ran a survey, essentially asking them, what else would you want to buy from us if we were smart enough to sell it to you? Essentially, they say courses, ebooks, things like that. Basically, teach them to do what we would do for them. I ran a pilot. I ran a coaching program. So I didn't pre-create content because that's a lot of work. It was like live Zoom classes. I mean, before the Zoom class, I prep what I'm going to show. It was a screen share. Of course, I knew my shit. So it was easy. So I was just figuring out. I'm going to teach you this and this. Around maybe two cohorts of this, I made half a million bucks. I was like, okay, there's a business here. People are ready to pay money. I think I charged $2,000 per person for a 12-week program. That was like, okay, there are people who are ready to pay for it. They're not just saying they're actually paying for it. So that's it.

The second reason was that I just personally got tired of being a consultant. I was the founder of the agency. I was the face. I was the lead consultant. Most customers requested to work with me, in particular. I think being a consultant comes with an expiry date. I got tired of explaining the same shit over and over and over and over again. So I was looking for, what else can I do if I'm not a consultant anymore? Then this e-learning opportunity just came about validated it. It was like, okay, this is it.

Alex Kracov: Did it require a cash investment at all? Did you use the agency cash flow to fund it? I guess you kind of ran that test. You got some money, and then that started kicking it off. But I guess it's just creating content online, so it's just packaging in a different way. How did you think about the finances?

Peep Laja: Yeah, so the agency was profitable. We were making a couple of $100,000 of profit every year. I don't remember the exact amounts, but we had some hundreds of thousands of dollars in the bank account just sitting there. I had read about many agencies who were like, "Oh, yeah, one day, we'll be the SaaS company like Basecamp." But 99% of them never get to it. Why? Because they're always busy with plan work. It's like, okay, I identified the necessary ingredients to start a side business, Basically, it's that you need top leadership attention. So basically, the founder starts pushing the new initiative in a higher, brand-new set of people to work on this new initiative. So nobody is like, "I do four hours of client work and four hours of this new stuff." It doesn't work. Split attention.

And so we had budgeted that we have about maybe - I think we had nine months of runway to get to break even. So I hired, I think, five people, if I remember correctly, plus myself as the founding team of this e-learning thing. It took us five months to build the platform, initial content and all that stuff. Then we launched. The results were underwhelming. It was very low revenue. I think it was like, we made less than $10,000 a month, $8,000 a month. Our expenses were higher. Every month, we lost money. But we were also agile with customer research and looking at who's churning and who's not churning, and what's the difference between these two groups? We learned that the smaller the business, the faster they churned. The bigger the business, the better the retention. I was like, okay, so we need to go for bigger businesses. So we increased our prices, changed our messaging - we're for bigger businesses, not the one-man companies - and also changed some other stuff. One month before running out of money, we got to break even.

Alex Kracov: It's a great story. And so I imagine it's like a marketing team or somebody at the big company is buying the e-learning for their team, right? A CMO is like, "Hey, my team needs to get better at this topic area." Is that generally kind of who you sold to?

Peep Laja: You're exactly right. Marketing leader is actually the number one buyer. It was marketing agency. A marketing agency is people-heavy. And to cut down on costs, you usually hire young people. It costs less. Young people don't know that much. So, of course, it is a great way to upskill them fast, basically. So it was a good match with that audience.

Alex Kracov: How did you scale the content over time? Because I assume you weren't the one just making all of these videos, or maybe I assume you did the bulk of the ones at the beginning. But then, how did you sort of recruit other people to create videos? What does that creator side look like?

Peep Laja: In the beginning, it was just me. I only know so much. So after a while, I was like, well, I have nothing else to teach. We sold subscription access. Common reason for canceling was, "I already went through all the content." That's a problem. That's a problem. It should be like Netflix. You can never watch everything, right? It's like, okay, it needs to scale beyond me.

I knew other experts in the business. Because if you're a consultant, you go to conferences. You meet everybody. And so, one by one, I started recruiting my personal industry friends. At first, we did revenue share. I forget the exact percentages, but we'll give you a significant cut. Maybe 40% of your core sales. Then we overpaid a lot. Some of these early instructors made a lot of money. Then we learned, okay, we're paying too much. How about we change to a fixed-fee model? And so we did. So we started approaching people. "Hey, we pay you this much money. Would you produce a course with us?" They said yes. I'm like, whoa. It's working.

And so for the first two years, I think we just ran through my personal Rolodex until all my friends had been instructors. Then after that, it was like, okay, we just go by topic. Let's say, it's a LinkedIn ads course we want to produce. Who is the best in the world at LinkedIn ads? Build a shortlist of some 5 to 10 people, and just approach them. Hey, are you interested in this much money?

Alex Kracov: I assume there's a great flywheel there, too. Because each person you recruit, they probably promote their own course on their social media and stuff, and then bring in their audience to come check out the course. Was that how it worked?

Peep Laja: Well, actually, this was our hypothesis, but it proved not to be the case. In fact, what often happened was that they taught the course with us. They had to put in the work to build a curriculum, and they just re-record the same curriculum on their own and put it on their website. It's kind of competing with us. These days, I think the policy is actually not to work with consultants anymore, but in-house people. Because in-house people, they're usually employees, not entrepreneurs. Whereas consultants are typically entrepreneurs. And so they're not going to go and build their own course to sell as a side hustle. Whereas the agency people, absolutely, they will.

Founding Wynter

Alex Kracov: It's a really interesting dynamic. There are so many courses that so many people do on things on LinkedIn now. It's pretty crazy what it started too. Alright. Let's switch gears and start talking about Wynter. So you spent the last three years working on Wynter. Can you talk about the founding story of Wynter and how you come up with the idea?

Peep Laja: Yeah, as I said, in the beginning, I had a failed SaaS business in my past. It was like an itch. I always thought that doing a SaaS business will be fun. But it always seemed like every business had already been done a thousand times, and I had no original ideas for what to do. Then one day, as we were, again, launching a new course at CXL - I was writing the sales copy for the pitch - I wasn't sure if it's good. I was like, I wonder if my ideal customer reads this, are they interested? Are they turned off? What's good? What's not good? There's got to be a tool out there that will tell me. I can put it in front of my ICPs, and they will tell me what's good about it. I found nothing. All I found was other people with the exact same problem. Then I was like, woohoo. Is there an unsolved problem I just stumbled upon? That was kind of the genesis of it.

Once learning that it truly isn't an unsolved problem, you want to validate whether it really is a problem. You want to validate the problem, and then you want to validate your idea for a solution. Because also, even though I knew what the problem is, how to solve this was not obvious. We had many conflicting different hypotheses, ideas. We thought Amazon Mechanical Turk. If you know how it works, basically, you can give people tasks, and you pay them money per response. And so we built the first feedback model using Amazon Mechanical Turk on consumer panels. Then we built prototypes, basic Figma prototypes. Then we did 30 interviews. I shouted on LinkedIn and Twitter, "Hey, who is writing copy but unsure if it's any good? Raise your hand. I want to talk to you." We landed about 30 interviews. Basically probed, investigated. They used to have a problem with validating how good their copy is. It seemed that, yes, it has legs. Then we showed them our prototypes. We got their feedback, how they want it to work. Will the solution work for them? And identified quickly solid trends of themes of how people would want it to work. Then we got to work. I hired one single developer and started building it, the first iteration.

Alex Kracov: Then how has the idea evolved from those initial customer development interviews? You mentioned this idea of panels, right? Because my understanding of Wynter, there's a group of people who actually go look at the messaging or in your ICP. Can you paint a picture of what the platform actually does?

Peep Laja: Totally. Well, building the whole system probably took a year before we opened anything to the public. It was like a year of building, iterating, which we deleted everything and rewrote everything from scratch once again. Because the first developer we hired was actually incompetent. We only found out later. Yeah, and so it was all based on Amazon Mechanical Turk audiences, that we could pre-survey them about like, hey, do you like to drink coffee, do fitness? Are you into crypto, or are you a sales marketer? This way, we filtered out who are the fitness people, and who are women, and who like to travel. And so we had all these consumer audiences. Travel companies wanted the travel people, and fitness companies wanted the fitness people.

We went to market May of 2020. Our first iteration, we called it Copytesting. Even though the signup interest was high, I think we got more than 1,000 users within a week of signing up. Signing up is free. The stickiness. Then from free to paid conversion was very low. We had more customer interviews. Then our hypothesis was that our buyers are copywriters and b2c or e-commerce product managers. We have product marketing managers. Basically, people responsible for the product pages on e-commerce. What we learned was that copywriters hated us. Because they had been getting away with writing whatever copy they wanted since the beginning of times, and there was no criticism besides your opinion. So they wanted to keep it that way. Second was, e-commerce product page owners, they never thought about the copy. The copy that they wrote and put out there, it never changes. They never tweak it. They make zero changes. And I'm generalizing here, obviously. So your average e-commerce site never changes a single word on the product. That was a problem. And so our hypotheses about who the target audience were wrong.

Then immediately, we started getting questions. "Hey, I'm targeting finance managers. Do you have them?" Or, "I'm targeting b2b SaaS marketers. I'm targeting cybersecurity people." We're like, "No. But do you want moms between ages of 20 and 40? We have those." Then we tried to do like, "Instead of Amazon Mechanical Turk, can we use another? Like a panel company to source as b2b audiences?" There are a lot of them out there lose seats. It's a saturated market, commoditized. We discovered that it's full of fraud. One customer required a market and b2b marketing audience. It was like, SEO for organic traffic was our customer. So b2b marketing leaders were looking at the copy and writing feedback. The feedback they wrote was, what does organic food have to do with traffic on the street? Meaning, these ideas of organic traffic, they didn't even know what it is. I mean, these were no b2b marketer.

Alex Kracov: That's not a real marketer.

Peep Laja: No, no, no. Then it turned out that this panel fraud is just rampant in all these panel companies. It's like 17-year-old dudes from India signing up and saying, "Yes, I'm a SaaS CMO." And nobody checks. Nobody verifies. So it's like self-reported identities. Then I was like, okay, everybody sucks. Can we do it on our own? Can we do our own b2b audience panels?

We ran some first experiments, recruiting first people from our own newsletter, verifying who they are on LinkedIn and all that stuff, and ran very small-scale tests. "Hey, you, dude, who wanted finance manager. Now we have 10 finance managers. You want them?" Then we did the test. Suddenly, our average customer happiness went from 3 to 10. I was like, whoa, holy sh*t. Now they like it. Because always, all results that they got from us were like, you know. And so this b2b audience, the feedback was extremely high quality. Then we did more validation, more small-scale tests. Everything was no code. We use type form and web flow. We didn't write a single line of code to test any of this. We have identified a model that works. Now, it's just how can we scale it and grow it and do it on a larger scale? And so we rebranded our company from Copytesting to Wynter focused on b2b. That was three years ago.

Alex Kracov: It's such an amazing story of going through the idea maze and trying to figure out, okay, what's the product, what's the audience, who am I building for? All of that. You landed on a solution. That makes a ton of sense to me as a b2b marketer, where it's like I've spent so much time staring at website, coffee, and wondering whether it's the right message or not. My team joke is like, I change our homepage all the time. Because it's like, one feeling I have, one conversation. I had prepared for this interview. I literally updated our homepage copy.

Peep Laja: I'm the same way, man. I'm exactly the same way.

B2B Website Messaging

Alex Kracov: And it's so hard to figure out what is right. Then the problem with b2b, too, is like there's no - it doesn't have enough traffic to actually run a B test. And so it's like this more Meta thing of like, how am I explaining the overall company? Then sale is going up. Will I explain it in this way? Because I think of it as the messaging also connects back to the product itself, and what are we actually offering to people and all that. And so yeah, I don't know.

Peep Laja: Yeah, I also find that when you're building a business, you have two things. You have: can you come up with a value proposition that people want? If you can deliver this, here's money. Then it's like building the actual product. I find that the value proposition side, finding what the market is ready to pay for, is the hardest piece. Because it's rare to come up with an offer that people are like, "Yes, take my money." And if you find one of those, then the rest of your business is figuring out how to actually deliver on it. That's your mouth and the secret sauce and all that stuff. But it starts with the value prop. The value prop, of course, it relies on your original insight, and ideas, and experience, and all that stuff. But it's also the words. How do you communicate? If you communicate it this way, will they want it? So the words are extremely powerful and important.

Alex Kracov: One thing I always go back and forth on is like, do I communicate the what? What does this product actually do? For Dock, it's a customer workspace that helps you with sales order forms and organizing content, versus the why, which is like, we'll close more deals. We'll help you accelerate time to value - the outcome-based messaging. I know the outcome-based messaging is how you actually win a deal, right? You're solving a real customer pain point. But it just feels so vague sometimes. Every other website has it, so that's a hard balance. I don't know how to put that.

Peep Laja: Yeah, because people, when they're shopping, they're not shopping for an outcome. They're shopping for a specific what. What is it? Because they have an idea that the what solves their pain or whatever, desired gain. So, yes, on the website, you balance both. But the what, what is it you think is more important? Because when they land to your website, ideally, it's not their first contact with you. They've seen you on LinkedIn. They've seen your ads, or they saw you speak at a conference. So ideally, the why, the narrative, the story, they're already familiar with it. They've been exposed to it somehow. Maybe they joined your newsletter and got a weekly newsletter. They followed you on LinkedIn, and then they see you every week talking about something, a bigger narrative. Then they get to the website. Then they already know the why now. And so it's like they only need to connect the dots. The sent needs to be there. Oh, this is what I saw on LinkedIn. It's reflected here in a short, concise way.

Alex Kracov: Yeah, it makes sense. And if you go with the why, the outcome in the why can be the same for many different companies, right? Every sales tool is probably going to help you close deals faster, impress your customers and whatever it is.

Peep Laja: Exactly. Anytime I see this match testing data all the time, where people are just making the scale. Yeah, increase the velocity of your deals and close deals faster. They're like, okay, yeah. But how do you do it? They want the specifics. So many companies omit the specifics. There's no get a demo, and then we'll tell you. Now, they're not going to get a demo. Time is precious. People don't want to get demos. And so you need a lot of like, this is how exactly we do it, the screenshots and interactive demos and all that stuff.

Alex Kracov: The other tricky thing I think about too is how your messaging evolve depending on the stage of company. Because at a seed stage company, you probably have one product, one core use case. It's easier to describe the what. Versus SAP, to use an extreme example, they have 1,000 whats. They have 1,000 things. And so they have to be super broad. Or even Lattice, a much more reasonable example. And so you look at these bigger grown-up companies. It's like, they're actually the worst ones to get messaging from because it's so obscure. People already understand the what.

Peep Laja: Yeah, exactly.

Alex Kracov: I don't know. It's hard to balance.

Peep Laja: If you go to, I haven't been there for a long time. But I bet they're not saying what they are and who's the ICP. It's probably some brand-

Alex Kracov: It's Dreamforce or something, right? Yeah, maybe promoting a conference of some shape.

Peep Laja: But every big tool like that started as a point solution. Sure, there have been companies that have tried to start as a platform. Most of these have failed because it was just trying to be too many things to too many people at once. It's hard for a company to stand for more than one idea. Unless you do it slowly, over time, you expand. But there's a hope. Somehow, Salesforce was just cloud-based CRM, right? That's it. It was a very simple idea at first.

Same with us with Wynter. My vision for where it will go has always been up here. It has been so tempting to already talk about the future that I'm seeing. We're going to be this great. Even though, the product is here right now. So I intentionally positioned us from the get go as a point solution for b2b message testing, even though the vision is much, much bigger. Only now, three years being in the market, we are now starting to reposition ourselves to go from being a point solution to a slightly bigger platform. Because we've developed more use cases. Even the type of buyer is different. So typically, we sold to product marketing. But now we have use cases that are more suitable for demand gen, even sales.

Alex Kracov: And as you expand those use cases over time, and whether it applies to Wynter or other companies, how do you think about the relationship between the homepage positioning and messaging versus all of the product and solution pages? Because you can get away with slightly different messaging. That's the reason why you create those other pages. How do you think about that web of website messaging?

Peep Laja: Yeah, you still need a concise and compelling way to sum it up. There needs to be unifying thread. Which is why in terms of positioning, you need to pick a frame of market category, frame of reference. So basically, what category of product you are. It's tempting to also say things that, basically, you don't fit into any existing bucket. And so you coin your own terminology, which is good because you're different. But it's bad because people don't get it.

For instance, for us, I've considered like, should we call ourselves a buyer intelligence platform? Yeah, that seems like nicely grouped together. But if you put it in front of somebody, what the f*ck is buyer intelligence? It sounds like such jargon buzzword garbage.

Alex Kracov: Gong, right?

Peep Laja: I mean, I think any intelligence category actually sounds pretty stupid, except business intelligence which has been around for 30 years or something. But all this revenue intelligence, no. But of course, a category name is like a logo. You fill it with meaning over time. Nike swoosh wasn't an amazing logo from the get go, right? It was just a thing. Now there's a meaning behind it. They have filled it over time. Also, I'm not too hung up on the category name like Gong and Revenue Intelligence. Well, now it has a meaning. At first, when I first saw it, I was like, this is f*cking stupid. But now it's not so stupid anymore because now it's a real thing, right? It's Gong. So I'm not too worried about what to actually call anything. Because it's to be expected that it sounds stupid at first.

Alex Kracov: Yeah, so much of marketing advice is go create a category. Go create a category like that Blue Ocean Strategy book or whatever, or a playbook. Those are all great concepts and ideas, but I found it so much easier to go reinvent an existing category. Take an existing line on it and take an existing workflow that somebody has, and explain how you're going to do it better and a more modern way. That's like what we did at Lattice for performance management. That's what we're doing now at Dock. It's just a much easier path as a marketer and I think business builder.

Peep Laja: Well, context dependent. So I think some categories is just so saturated, that if you're yet another marketing automation email marketing tool, I think it's very hard to stand out. Because you go to G2, there's like 500 of them. The thing in that case, you would benefit from being something different. Of course, you do need to bring actual innovation too. It cannot be that you do the same, but you just call yourself something else. That doesn't work. Blue Ocean is a little different, of course. Because Blue Ocean is that you remove some essentials that everybody has, and then you dramatically cut costs because of that. Then you lean in on something else. The book has a lot of examples how you can do that. We're not going to go into it right now.

And also, category creation, there's conflicting opinions there. Some people say a category is like CRM. There's a lot of tools that all CRMs category, or it's a form of radical differentiation. Meaning, that you can be the only one doing what you are. You're a unique type of product. Because right now, Wynter, for instance, is b2b message testing tool. It's the only one in the whole world. Really, we're the only ones in our category. Is it a category? Well, not by Gartner. But it was like, what type of a tool is it? What category of a tool is it? Man, it's a category. B2B message testing.

Alex Kracov: Yeah, one day you'll be on the Gartner Magic Quadrant leading it all, right?

Peep Laja: Yeah.

Wynter's Growth Strategy

Alex Kracov: Let's switch gears and talk about Wynter's growth strategy. How do you think about getting Wynter into the consideration set for b2b buyers?

Peep Laja: Many different ways. So you use what you have. I don't have a lot of money. So I was like, okay, I got to be clever. Also, my skill set used in previous companies has always been leading with content. We didn't have a lot of SEO backlinks. And so ranking for competitive terms was not really a viable strategy to make money next month, maybe three years from now. So I haven't focused really on blog and SEO that much. We do have it. So we leaned heavily in on LinkedIn and Twitter. Also, me, as a founder, I leaned in that, okay, people resonate better with individuals compared to company names. So I'm going to have to become an influential person. Influencer marketing really works especially if you're the influencer.

In 2019, when we first started toying with the idea of building this company, around then I made this decision, okay, I need to go all in with LinkedIn and then build an audience. I had some name recognition already before, but it was in a different industry - conversion optimization. In this new world, it's product marketing dimension. Nobody knew who I was. So basically, it was building it from scratch. So that was one. So posting every day, making myself right. That was one big part of it. And of course, I'm pushing a narrative. Sometimes I'm writing about whatever the f*ck. But mostly, I'm building a story of why ICP research and messaging and why it's so important. I find 365 ways to say the same thing. That's one.

So the way I think about marketing is like, there are two buckets. One, create awareness that you exist. New startup is the hardest part. Because most of the market doesn't know you exist. And so differentiation plays a huge role there. Also, it has been extremely beneficial for us to be the only tool that does what we do, the only one. So we get a lot of word of mouth in Slack groups or LinkedIn discussions. Somebody says, "Hey, how can you test my messaging?" We get 100% of that word of mouth. So it's been really useful to be differentiated.

Then stay at top-of-mind part. So if they want to find out about us, how are we building mental availability, so they will think about us in buying situations? And so this is just posting daily on LinkedIn and Twitter, sending a weekly email newsletter, throwing multiple online virtual events a month, workshops. The type of webinars, we call them different things. But essentially, it's webinars. We tried to do multiple per month, high-quality stuff, weekly newsletter I mentioned, and then product-led content. So I do this show. Maybe you've seen this. I call it, do you even resonate post on social. I tried to make it entertaining but I'm also screen sharing my product, which has been very effective for us. This idea, I got from Ahrefs for their blog. The way they write blog posts is like they write an article about a problem, SEO problem, that people have. Then they show how to solve that problem using their tool. So that was the original inspiration. Those are the main things we do. That's 90% of our marketing, I want to say.

Alex Kracov: Then one other part of your marketing that I've noticed was, you invested in some of these, I guess, social commercials. The Wynter best man speech and the proposal ads are hilarious and amazing. You did such a good job explaining your value prop. Can you talk a little bit about this?

Peep Laja: Yeah, absolutely. So this comes back to the first bucket - make people aware that we exist. And if you do brand advertising, the brand advertising really needs to answer three questions: what is it? What's it called? When should I use it? In marketing literature, they call it category entry points, category entry point marketing. From neuro marketing, it's known that the most effective way to communicate an idea is contrast. I was fat, and now I'm skinny. I was poor, and now I'm rich. Contrast. So I wanted contrast, and I wanted these: what is it? What's it's called? When do I use it? So that was the idea. We need video ads that have contrast - before and after, bad messaging, good messaging.

But producing video ads, high-quality video ads, about 30 seconds long is very expensive, especially for startups. So if you go to such a video production agency, small startups need to be scrappy. I have a friend who's like a C-list celebrity. Not even a celebrity, an actor in Hollywood. I said, "Hey, do you know anybody in Hollywood who is looking for a side gig and wants to make commercials?" He's like, "Yeah, I know a guy." He's a struggling musician dude. Put me in touch with him. Basically, I found that Hollywood is full of these extremely talented people - script writers, actors, you name it, directors - that are looking for their big break. 99% never make it. They're working in Starbucks and whatever. But they all want to build their resume, their portfolio. So I found all these people, these actors and the filmmakers basically put together a crew and produced these ads for $10,000. 10 ads for $10,000. So it's $1,000 per video. Extremely scrappy. Then yeah, we use these as retargeting. So once they come to our site, we follow them around with that. Build mental availability. Train them to think about Wynter.

Alex Kracov: That's an amazing story. Because yeah, ads or commercials can be so expensive. I think when I tried to do this stuff at Lattice, 50k was the minimum. Probably 100k. It gets crazy when you go work with the agencies. It's a good story. The ads are fantastic. They're super high quality. They do a great job managing, explaining the message and the value prop of Wynter. It's really, really well done.

Peep Laja: Yeah, we rented an Airbnb. Basically, everything was shot in that Airbnb - front yard, backyard, different rooms.

Alex Kracov: Very cool. Then how do you think about events as part of your strategy? I know you have the Wynter Games and then spring. I've seen you post a lot on Twitter I think about how connections are maybe even more important than the content.

Peep Laja: That's right.

Alex Kracov: How do you think about events?

Peep Laja: Virtual events are just so easy to put on. Everybody should put on virtual events. You don't want to do your regular webinar stuff. You want to have a more interesting spin on it. So Wynter Games is like, if a lot of companies do online conferences once a year, why can't you do one every month, every week? That was the premise. We started doing every month a virtual conference, 20 speakers. It was like all-day marathon, eight hours. I was always the moderator, so it was extremely tiring actually to listen, to actually pay attention so you can ask good questions.

Since then, we've cut down the amount of speakers and how long each talk is to four speakers. Because what we also found out was, for every virtual event, it doesn't matter who the speakers are, what the topics are. You have the most viewers, speaker one. Then it just declines slowly. Even if you have the most famous person as the closing keynote, it will have the least amount of viewers. It's just guaranteed. But the amount of registrants, whether you have 30 speakers or 4, is the same. There really was no point doing longer events. It's not called a webinar. So it's a more interesting value proposition people pay more attention. So that's the Wynter Game stuff.

We also started doing real-world physical conferences. We've done one last year. Actually, last spring was the first conference. We called it Spring. Why do a conference? Well, first of all, at CXL, we're still doing this conversion optimization conference called CXL Live. So we have a lot of conference, organization experience. What I know is that conferences make you seem bigger than you are. As a smaller startup, credibility is the name of the game. As you want to go more upmarket, get bigger budgets, bigger companies to pay attention to you, and some individuals are risking their reputation on buying you, you need to seem more credible.

A conference is still - well, not only conference. In-person conference still seems more credible, because the barrier to entry is higher. Not everybody can pull it off. So you must be a big conference if you're putting on a conference. In reality, it doesn't need to be expensive. It doesn't need to be complicated. It can be varied. This particular conference, I organized single handedly. Because I had a small team. They've never done a conference. For me, it's easy. Because really, what you need is pick a date, book a venue, make sure there's food and drink, invite some people to speak. That's it. Alright. If I could do this all in one day, it will take me two days to organize this conference. Selling tickets is harder, but you can mitigate risks by just avoiding hotels and conference centers because those guys know how to charge money.

I rented out a brewery. They just said, "Hey, typically, in this day, we do this much revenue. So this is the food and beverage minimum," which was I think 30k or something. "If you hit this, everything else is free." So I was like, sweet. In order to hit this minimum even, I made it all you can drink and eat, including beer. Unlimited. And we still didn't hit.

Alex Kracov: I love the story. They're like, I don't know, appearing bigger than you are. That is such a good thing for all startups to take away from this conversation. It's a lesson I kept applying again and again at Lattice. You can invest into a little bit more into design or conferences and just do things that big companies do. Then you feel like a big company, right? Everyone's always surprised how small you actually are.

Peep Laja: Yeah, exactly. Don't go and buy a booth at Sasser, because that's just a ridiculous expense. But you can do similar things, but just be smart about how you organize things. You can throw dinners around big conferences and paying for food that are not that expensive.

Alex Kracov: Something I was curious about was, does Wynter have a sales team? Or is it all product-led growth and people just signing up and paying in the end?

Peep Laja: I have a salesperson who was a closer. But the leads are inbound. So everything is coming in inbound.

I used to be the closer. But then, I often spent most of my days doing demos. It was like, okay, I can't do anything else anymore. I hired a guy. But I didn't want a rookie AE. I couldn't afford the best AE in the world. They wouldn't want to work for a small startup either. So what I did was, I hired a fractional VP of sales. Fractional marketing people, I'm very skeptical about my experiences. Not stellar. But sales, you close it, or you don't close it. It's very measurable, right? If you do a fractional VP of sales, you get somebody in who has 15, 20 years of sales closing experience, follow-up experience. They'll close way better than your 26-year-olds. Way better. I still use a fractional VP of sales as my closer. So that's been working out great.

Running a Bootstrap Business

Alex Kracov: Super interesting. I'd love to end today's conversation talking about, I guess, how do you run a bootstrap business? Because you've done this a few times now. It's a complicated formula. You're managing cash flow. You still need to grow. This is something that everyone is facing, especially today in today's market. How do you think about managing growth, but then also being profitable as you grow Wynter and excel in all these different businesses?

Peep Laja: Yeah, so as you said, Wynter is not my first business. So the first startup capital was my own money. I was my own VC - using the profits of my other company, CXL, to hire people, to fund the development of the MVP, all that stuff. That cost was, I want to say, around 500,000, at least, of my own money putting into fund the first thing. Then I thought I'm going to raise VC money. But the VCs didn't. They're like, message us this new idea also. So it wasn't obvious for them. Our biggest attempt: can these be a venture scale, a.k.a. 1 billion plus business? They didn't see it. So I was unable to raise money. In retrospect, I'm very happy I wasn't able to raise money.

What I did instead was, I did a small angel round. Any angel round, I basically reach out to people that I knew or assumed that have some money. Because there are laws about asking some people to invest in a business. The rules are: that you need to have intimate knowledge that they make at least 250k a year. I'm guessing. But basically, you raised $500,000 something from small checks. Some people put $1,000, some $5k, $10k. I think highest check was $50k. All in all, I think it's 200 different people. I used the AngelList RUV as the instrument. So they're all a single entity on my SPV and my cap table.

That money, again, paid for some salaries. Because the higher the team, the bigger than we could afford cash flow-wise. So I hired in advance just to make faster progress, which is also why it would raise VC money, right? To hire people. Last year, financially, we took a loss because I hired all these people I couldn't afford. But the angel money paid for it. This year, a third year in business, we broke even in March. We've been breakeven or slightly ramen profitable ever since. We're a team of, I think, 16 people today. First year in business, we did $450,000 in revenue. Last year, we did 1.2 mil. So it was almost 3x growth. This year, we're on par to do 2.4. So 2x again.

Alex Kracov: Very cool. Then how do you think about investing into the growth? Is it just, you're looking at the goals in the future and then trying to just be really careful to not go over a certain amount of spend each month? I guess it's just a simple spreadsheet.

Peep Laja: Yeah, basically, I'm checking my bank account balance every single day or every other day to make sure. Your number one job as a CEO is to not run out of money. Do not run out of money. Easiest thing is to hire yourself out of business. You just hire too many people or too expensive people. I'm careful about that. Once we start making more money, because always the idea is, it's not about cutting costs - unless it's unavoidable - but it's mainly about, how can we make more money? That's what I spend most of my day, thinking about how can we make more money? How does the product need to change? How does marketing need to change? The whole thing.

And if you read strategy books - I'm a big fan of strategy books - they talk about identifying the crux. The crux is, if you set your business strategy, it's not about, "Oh, I want to make $10 million," and then your strategy flows from a goal. No, your strategy flows from identifying the problem. You need to identify the right most important problem and really answering the question. What would be the one problem that I could solve that would make everything else much easier? And so that basically tells you what to prioritize, where to put the most manpower, human's attention. Because change in priorities also needs to come with change in resource allocation. Otherwise, it's just talk. And so how I'm investing is, as soon as I can afford another person, I know exactly where we need to invest. I'm putting all the money back into hiring. Ad budgets, I'm not increasing that much. I think we're spending $10,000 a month, or something like this, or maybe a little less.

Alex Kracov: Yeah, that's the nice part about organic growth, too. A lot of growth can come from your audience and all the different things that you're putting out in social. Thank you so much for the wonderful conversation today. If people want to use Wynter, if people want to follow up with you, where's the best place for them to find you?

Peep Laja: Yeah, LinkedIn. Check me out.

Alex Kracov: Right on. Thank you so much.

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