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Nick Rybak explores how modern B2B companies grow through marketing strategies, website innovation, and content that converts. Every two weeks, we talk to marketing leaders and founders about what’s working and what’s not.
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Nick Rybak (00:00)
Most people would say it’s crazy to build project management software today. There are ClickUp, Asana, Monday.com, and a lot of other companies that have raised hundreds of millions of dollars and have entire teams just for A/B testing their onboarding flows. And yet, Davidson Wicker did it anyway. He’s the founder of Ravetree, a project management and collaboration tool built for agencies and professional services companies.
But here’s the twist. Ravetree didn’t raise any capital. They bootstrapped from day one. So they have a small team, no venture capital, and no crazy burn rate. And still, somehow, they have managed to win real B2B customers in one of the most competitive SaaS categories on the planet. Today, we are going to talk about how he did it, how to survive and grow in a market full of giants, and what channels actually work when you don’t have a marketing department of 20.
And why staying small might actually be your unfair advantage. So let’s jump in.
Nick Rybak (01:04)
Davidson, thank you for making it. I love a good founder story, but yours starts with physics, not software. So tell me, how does someone with a background in physics end up running a project management platform?
Davidson (01:19)
Yeah, that’s a good question. Well, I don’t know how to answer that. I got my degrees in physics, but I never really intended to be a physicist. I was just interested in it and knew that I was going to do other things. I did teach for a couple of years, and that was really just because I graduated and was like, “Well, I’ve got to find a job.” So I did that for a couple of years. But then I went and started doing software, and I worked mostly at product companies, like Ravetree, where we just built one thing. But the last job that I had was at a software agency. And I saw it was very different: billable hours, that kind of thing. The company had built an internal tool to try to manage everything, and it was awful. It didn’t work. The developers there worked on it when we had free time between projects. And I’ve seen this before at other companies; I’ve heard people talk about similar things where they try to build an internal tool, and it never works. So, I said, “You know what? I can do this.” I saw the challenges and the problems. So that’s kind of what led me down this path of building Ravetree. So yeah, that’s the origin story.
Nick Rybak (02:45)
So you built that for yourself first, or let’s say, for the company that you worked for? And did you think that you could sell that to other companies that might have the same problem?
Davidson (02:59)
Well, to clarify, I didn’t build it for the company that I worked at. I built it after I left the company; I decided I wanted to build something that could address the needs of agencies in general. I knew agencies of any kind had a lot of common issues and pain points, so that’s kind of where it started.
As for customers, did I know who the customers would be? I thought I knew, and I was pretty close to being right with my assumptions, but as with any startup, you think you know who you’re going to sell to, and it usually ends up being a little bit different, at the very least. So I was fairly close, but I had a lot of conversations with companies, especially in my area, to see if this was something they would be interested in. I showed them the prototype.
Nick Rybak (04:05)
Thank you for clarifying that. Did you have a specific problem you were trying to solve with that software?
Davidson (04:15)
Well, at the time, this was back in 2016 or so, maybe even 2015, the software that was available then wasn’t like today. You didn’t have all those big names. Some of these companies had technically started, but they weren’t big names like Monday, ClickUp, Asana, et cetera.
So there was no one who was the clear winner, and it wasn’t as saturated as it is now. So yeah, it was definitely different back then.
Nick Rybak (04:55)
Yeah, that’s a really crowded space. I would say in terms of software for B2B companies, maybe a CRM would be more competitive than project management software, but that’s definitely top-tier competition. Have you considered the level of competition back then? Was there any big player in the space at that time?
Davidson (05:17)
Not really. There was Jira. So coming from software, we were using Jira. Although they’ve obviously evolved over the years to try to be more compatible with agencies, I didn’t like it. It’s a powerful tool, but I thought it was very clunky. I mean, I would say that was kind of the big one.
You know, now we don’t compete with Jira. No one ever comes to us and says, “Hey, we’re looking at Ravetree or Jira.” That’s happened maybe once out of the thousands of demos that I’ve given, but that’s not our competitor today. The companies that are coming to us are coming from tools like ClickUp, Asana, and Monday. They’re using them and they realize, “Well, there’s got to be something better suited for an agency setting, for companies that are doing billable hours.” So yeah, today there’s definitely a handful, for sure, but back then it was probably mostly Jira.
Nick Rybak (06:33)
Got it. How did you define your niche and differentiate Ravetree early on? You mentioned that you intended to build software for agencies who sell hours. Did you have any specific ICP or buyer persona, something like that?
Davidson (06:54)
Yeah. I mean, we definitely do now. It tends to be agency owners, you know, between their thirties and fifties. That’s kind of the range. I can narrow it down more than that, but yeah. Although we have customers all over the world, they are in English-speaking countries, as we’re not fully internationalized right now. So, we’ve got customers in Australia, the UK, South Africa, all over the place.
But it tends to be English-speaking agency owners between their late twenties to mid-fifties. That’s the typical buyer. And more specifically, it’s usually the founder or an operations director at the company, a COO, maybe a director of project management. It depends on the size of the company, but we’re typically dealing with SMBs. We’re not dealing with enterprise, so it is common for us to be dealing directly with the founder of the company.
Nick Rybak (07:59)
Yeah, that’s quite relatable because I remember the days when I chose ClickUp for project management software. I would say that project management software is the kind of tool that you choose once and you don’t really want to change along the way, only if it is letting you down somehow or it’s not keeping up with the progress of competitors. But in other cases, that’s so hard to replace. I mean, it requires so much effort, time, and so on. And I think it’s just not worth it.
Davidson (08:45)
Yeah, well, I mean, there’s definitely a little bit of pain in making a transition, but people do it for a reason. They might have a specific pain point that is really bothersome and that affects them every day. For us, there are kind of three people that we’re targeting within a company. There’s the owner, they just want their dashboard. They want a metric, a number. That’s all they want to see. Then you have managers, and they want all the bells and whistles. And then you have the doers at the company who just want something as simple as possible. They don’t really care about the bigger picture necessarily. They’re there to do their job, which might be design or software or whatever.
So yeah, that’s kind of how we see things distributed. But it can be painful. We make it as easy as possible, and I think it’s easier when we can demonstrate to them that if they’re currently using a handful of different tools, and usually it’s at least two, they can consolidate into one with Ravetree. That alone is going to solve enough of the pain they already have that the time and effort to transition is worth it. And it really doesn’t take as long as you might think to transition.
Nick Rybak (10:04)
That’s interesting. Alright. So you started Ravetree when ClickUp never existed and maybe Monday.com as well. But then your market became crowded, some companies raised hundreds of millions in investments, and you didn’t. Was that intentional, or did you just not want to, or not know how to? Can you tell us a bit more about that?
Davidson (10:42)
Yeah, absolutely. So, first of all, one of the reasons someone might decide to start a company is because they want to work for themselves. And that was very much a motivating factor for me, not the only one, but one for sure. So I knew that I did not want to go out and get investments. I knew that I wanted to bootstrap, and there are obviously pros and cons to doing it both ways. With that being said, early on when I was starting, even though I said, “Yeah, I’m not going to take money,” things got challenging in the beginning. And I said, “Well, let me go out and meet these investors and talk to some people just to see what that looks like.”
And we met with a lot of people, and we actually had one deal where we had the term sheet, the lawyers had everything drafted up. We were about to sign it. And I decided not to. This was really because we had a disagreement on the terms, and the investors wouldn’t budge. And I said, “Okay, well, we’re out.” So we walked away. And honestly, that was the best decision I ever made because I feel that if we had gone down that path, I would have been miserable. You know, I just… really, dealing with investors is a job unto itself. And it was a job I didn’t care to have. I didn’t want to deal with investors. I wanted to deal with customers and the product. And we’ve been bootstrapped the entire time.
Nick Rybak (12:18)
That’s quite popular in the bootstrap community, to weigh those types of conversations and the pressure as well. Because when you raise money, you owe them. It’s not free. It’s not a gift. You have to earn that back for investors somehow in the future. And yeah, that can be a certain level of pressure.
Davidson (12:35)
Yeah, absolutely. One other point about that is when you take money, the focus shifts. We were always very product-focused and customer-focused. And if you take investments, it 100% shifts to sales. You can’t get backed by VCs and then have them say, “Yeah, we’re okay with having outstanding customer support and putting funds into that,” or really focusing a ton on the product. It’s really mostly about sales. Marketing is a side effect, but it’s very sales-driven. It’s just a different approach. I always wanted to have a great product, but also a product that had great customer support. If you talk to our customers, they’ll tell you that’s definitely something that they appreciate about Ravetree.
Nick Rybak (13:45)
You’ve been bootstrapped all the way, as you said. You haven’t raised any capital, but you must have had some tough moments where you thought, “Maybe we should raise some funds and build a bigger company so it’s more sustainable, easier to maintain,” and so on. Have you had any moments like that?
Davidson (14:19)
I have not. No, I haven’t. Early on, when I was saying, “Well, let me just see what this investor thing is all about,” it was more just me being curious and wanting to see what that path would look like. It wasn’t so much like, “Crap, we have to do this or we’re going to go out of business.” It wasn’t that kind of a scenario. But ever since then, I have not once looked back. We have investors who reach out almost every day. I get emails and phone calls from investors of different types, taking an interest in Ravetree. I just delete all the emails. I don’t respond. We’re just not interested in that right now. Will we be in the future? I don’t know, maybe. But my thoughts now are that we’re thriving and we want to continue to do what we’re doing. We don’t really need venture capital money. Of course, taking money can allow you to grow more quickly, but we’re fine with where we are right now. So I don’t think it’s something that we’re looking at exploring, maybe ever, but certainly not anytime soon.
Nick Rybak (15:39)
And what do you think is the main advantage of staying independent?
Davidson (15:46)
Yeah. Well, there’s a lot. You don’t have to deal with investors. I think that’s a big one. It’s just another thing you have to manage, all the relationships around that. For me, I don’t want to deal with that. But yeah, just being able to stay focused on the product and customer support, those are things that we can do that would be put on the back burner, or at least it seems to be the case with a lot of companies that take VC money. Their customer support isn’t usually great, or there at all. We have conversations every week with prospects who are coming from all the big names you’ve heard of, and they’re like, “Yeah, the customer support is terrible. They don’t listen to us,” or, “They said they were going to fix something or build something years ago, and it still hasn’t happened.” And so for us, that’s a big opportunity, because we listen. We’re going to build that feature if they ask and if it’s something that we think fits into our development pipeline. Because we know who our target market is, we know what they want.
Nick Rybak (17:01)
Yeah, I think that’s quite important. Especially if you have some bugs, people at least want to feel that you know about them and you’re taking care of them, so they just need to wait. Alright. So that was about the early days of Ravetree. But then, when the market was already crowded, you were in a situation where every SaaS founder would think mostly about one thing: how to actually get customers, especially when you can’t outspend Monday.com and ClickUp on ads. So how did that work for you?
Davidson (17:50)
Yeah, it was definitely a challenge, and I’ve tried just about everything. I can tell you what worked for us and what didn’t. So initially, we thought, “Well, let’s just pay to be on all those lists that you see, like ‘Top 10 Project Management Software’.” There are dozens of them. It’s pay-to-play. If someone is number one on the list, it’s not because they’re the best; it’s because they pay the most. That’s really what it’s all about.
Early on, some of those lists did work. It cost a lot of money, but they were somewhat effective. That has completely changed now. Not that long ago, we had taken a break from that approach, and we said, “Well, let’s try it again.” It just didn’t work at all. There are probably a lot of reasons for that. One is that maybe it’s just more competitive now. It could be there’s just more noise and people aren’t paying attention. But those were highly ineffective for us.
We tried email marketing; I think email marketing is the worst, it doesn’t work at all. We tried cold calling. I spent times where I was just on the phone all day long and committed to it, saying, “I’m going to try this for a certain amount of time.” And I found that, personally, I don’t think that works. I think you’ll get people that’ll disagree, and I think it depends on your infrastructure, if you’ve got the team to support it. But at the end of the day, what has worked for us is word of mouth, believe it or not, and also SEO, which is something I regrettably neglected early on. I kind of took the mindset that, “Well, I can put tons of time and effort into SEO, and maybe I’ll move from being on the 80th search result page to the 50th, and that doesn’t mean anything.” But in hindsight, that was the wrong attitude. Since I’ve been focusing on it, and honestly, with the help from your team, we’ve seen a lot of success with it. I’ve really focused on the blog and writing content that we think is useful to our customer base.
So yeah, for us, it’s really SEO and word of mouth. That’s worked quite well, and there’s no direct cost to do those things. So that’s what’s working for us now.
Nick Rybak (20:29)
I think word of mouth works every time when your project or service is good enough that you’re not shy to promote it to your coworkers and friends. But with SEO, you raised quite an interesting topic. As I understand, you ended up trying it and you made some progress, being not in the 80th position, but somewhere in between. How did that affect your traffic? Do people really open five pages of Google search results to find a solution?
Davidson (21:15)
Five? Probably not in 99.9% of cases, but there’s always going to be someone who wants to dig deep, and they might go that far in the results. But yeah, even page five… most people would say even page two doesn’t matter. But we’ve actually been fairly consistent in being on the first search result page organically for a handful of terms, like “best project management software for agencies.” We’ve got pages that you can see. It varies from day to day; you could search for it and then search for it again later, and you might be on page two, but we’ve worked hard to be on that first page for a handful of keywords that are relevant to our target market.
Nick Rybak (22:10)
And how does that work in 2025 with AI overviews? Did that work out well for you?
Davidson (22:21)
Yeah, I think it’s been a mixed bag. People are still trying to figure out how those AI searches work. We’ve appeared in the searches. Many times when I search, we’re in it. Other times we’re not. It doesn’t seem to be very consistent, although you’ll always see Monday.com and ClickUp in there. Sometimes we’re in there, sometimes we’re not. You’ll notice that on Google, on the right-hand side, they’ll list what supposedly are the sources that they use for their AI results. Sometimes our blog articles will show up there. Sometimes it’ll be the first one. So we’re in there, I wouldn’t say consistently, but we are appearing in those AI search results. And obviously, it’s something that we’re thinking about every day and looking at ways to ensure that we’re always there.
Nick Rybak (23:16)
Got it. Have you ever tried anything like G2 or some kind of listings where people compare software before purchasing?
Davidson (23:31)
Yeah, we have. And honestly, my take on it is it’s a waste of money. G2 is very much pay-to-play. They’ve got some things where you can pay, like a starter package. I don’t know what they call it, but it didn’t move the needle at all. They’ve got another option where you pay a fairly significant amount of money to have an enhanced profile. I don’t think those things work, to be honest. I mean, that’s just my opinion.
We did Capterra, and that’s one where it used to work quite well back in 2019. But we have not gotten any good results since then. We tried it not that long ago, and it was really just a complete waste of money, to be honest.
Nick Rybak (24:25)
What do you think could be the reason for that?
Davidson (24:28)
Well, I think it’s noise. There’s so much out there, people are just like, “Don’t want to see it.” They’re not. And the other reason is this: I think with AI search, you don’t necessarily need to click into those sites to get the info. It’s just going to be presented to you. AI will extract the information for you without you needing to actually go there.
That opens up all kinds of questions, like what’s the future for those kinds of businesses. But I think a lot of people are still paying to be on these lists because they believe that it helps with their ranking in AI search. And it probably does. But I don’t know that people are actually clicking into it. We also found that we were getting tons of what had to be fake clicks. I can’t prove that a click is fake, but just random email addresses in the middle of the night and then nothing during the day. It was really quite frustrating when we decided to re-engage with a lot of these platforms. After taking a break from around COVID up until, say, 2024, we didn’t really utilize those avenues. But then we said, “Well, let’s try it again,” and it was just a profound disappointment.
Nick Rybak (25:55)
Yeah, I think there can be so many reasons for that. It’s hard to know for sure. But if it works, it works. If it doesn’t, it doesn’t, right?
Davidson (26:07)
Yeah, I mean, I think if you’re Monday and you can put in 10 million a month into ensuring you’re always the number one spot on G2 or Capterra or whatever, then at some level you could say it works. But they’re publicly traded; they’ve got the funds to do it. It was not cost-effective at all. It was just a complete waste of money.
Nick Rybak (26:33)
Yeah, I think this kind of thing is also an attempt to be top of mind always, because if you’re number one on Google and G2 and so on, it helps to win in the long run. But of course, for a small bootstrap company, throwing away thousands of dollars every month without seeing any traction is not the way you want to build your company.
Davidson (27:06)
Exactly. And you know, I don’t want to name names of companies, but there are some of our competitors that I know are successful, and you never see them on any of those lists. So they have different ways of marketing themselves. They’re not trying to be the Walmart of project management, like Monday, ClickUp, and Asana are doing. That’s sort of the way that I see it.
Nick Rybak (27:34)
Have you tried paid ads or something where you pay directly for clicks?
Davidson (27:40)
We have. We tried it several times. I’m not an expert on paid ads, maybe I should be, but when we tried it, and we worked with some other people in the past, it just sucked up a lot of money and we had very bad results. I think if you put more money into it, more effort, maybe a strategy that combines multiple things, perhaps it could be effective. But a lot of what I’m telling you as far as my opinions on marketing, obviously take it with a grain of salt because we’re a bootstrapped startup. We don’t want to put money into any marketing. We want to get it all for free. So we’re looking at things that cost very little money to no money at all to help us move the needle. So that’s why I have these opinions about some of these platforms.
Nick Rybak (28:44)
Can you recommend any marketing channels that can be a good fit for a bootstrap-sized company where you get almost free clients?
Davidson (28:57)
Well, not really. I mean, I don’t have a better answer than that. I think focusing on SEO and word of mouth. Really, if you’re starting out, for us and probably for every startup, find those first 10 customers. That’s the magic number. Get 10 customers that love your product, and that will act as references for other potential customers. Because early on, what would happen a lot is I’d have a demo, and then towards the end of the demo, they’d say, “Yeah, I like this. Okay. So, I haven’t heard of you guys. How long have you been around?” And it’s like, “Well, we’ve been around for, let’s say, a year,” whatever it was at that time. And they’d say, “Well, can you send us some references?” And obviously that’s really hard when you don’t have customers and it’s your first one. But once you have 10 and they love the product, you can start asking if they wouldn’t mind being a reference, and that helps a lot. So yeah, get those first ten customers, even if you have to go and just show up at their office if it’s a local company and beg for them to take a demo. Demonstrate to them how your product can help solve their problems and then get them on board. From there, it becomes easier, but it’s hard to get those first ten.
Nick Rybak (30:20)
Yeah, I agree with that point. Collecting testimonials from your clients starting from day one is essential for any business. Alright. I’ve asked you about how you get clients when the competition is so hard to deal with. There are probably some good sides to that. Do you think there are any advantages to being a small, bootstrapped B2B SaaS company rather than being a huge, publicly-traded company?
Davidson (31:08)
Yeah, absolutely. So first is customer support. And then the second is building the product and knowing what customers want. Really focusing on every single demo, every customer interaction that comes in from support. I read all the chats that come in, whether I was directly involved with it or not. I want to know what customers are saying, what they’re asking for, how they’re feeling.
And I think once you get to a certain size, inevitably it’s harder to do that. It’s harder to really know the pulse of your customer base. And for us, we know exactly what they want. We know exactly what they don’t want, what they like, what they don’t like. I mean, we know. And that’s helped us build our product so that we now have, in my opinion, without a doubt, the absolute best work management software for client service businesses. If you’re doing billable projects, we do it by far better than anyone else. And it’s because we’ve spent the time having those conversations, so we know what they want.
Nick Rybak (32:21)
Yeah, I love that. I love this obsession with the customer experience. Speaking of 2025 and your marketing in general, you’ve tried a lot of different marketing channels. Are you still testing some new ones or just doubling down on what already works for you?
Davidson (32:46)
Yeah, so we’re kind of doubling down right now. Of course, your company helped us update our blog, which we were very happy with. And we’re putting a lot of effort into writing content and promoting that content. So we’re doing a lot of social where we’re sharing blog articles, we’re doing a lot of videos, and just things like that. So that’s kind of what we’re really focusing on right now.
Nick Rybak (33:14)
If a founder came to you today saying that they want to build a B2B SaaS in a super crowded market, not one of your future competitors, but let’s say in CRM, what would you tell them?
Davidson (33:30)
Yeah. Well, first of all, why are they wanting to get into a really crowded market? And just to clarify with Ravetree, we’re in a crowded market, but when we started, it wasn’t as crowded. So it’s not like we just suddenly said, “Let’s jump into this crowded market.” It just happened to evolve into one. It’s tough being in a crowded market. Obviously, the traditional advice is to really focus on a narrow target market and make sure you’re addressing specific pain points for a specific type of client instead of trying to be generic. I mean, with CRM, I feel like there are more CRMs than project management tools. They’re just kind of a dime a dozen; they’re everywhere. And a lot of CRMs are being integrated into project management tools, like with Ravetree and others. You also see them integrated into marketing automation, with HubSpot being the primary example.
But yeah, as for a new founder wanting to jump into a crowded space, they would have to have something that really differentiates them from everything else. It might be some new technology, but there has to be something. It can’t just be, “Hey, I think this would be fun.” That’s not enough to move the needle. So if they don’t have anything that’s unique or any other really great reason, I would discourage it. And it does seem like, especially in project management, there are a lot of products, even now. You still see new products coming out almost every week, and they’re just kind of clones of everything else. They don’t really seem to be solving a problem. They’re just saying, “We’re project management.” Okay, so what is different about what you’re doing?
I would say, if I were starting a business today, I probably would not be in this space because it’s already so saturated. So yeah, it’s tough being in a crowded space for sure.
Nick Rybak (35:45)
Got it. That’s actually solid advice. If you don’t know exactly why you want to be in that specific market, if you have nothing unique and proprietary to offer, you probably should rethink that.
Davidson (36:06)
Agreed, yeah, 100%.
Nick Rybak (36:10)
Alright, so let’s end on a hot take. What’s one opinion you have about B2B or SaaS marketing that you think most people would disagree with?
Davidson (36:20)
Email marketing does not work.
Nick Rybak (36:23)
You mean cold outreach?
Davidson (36:26)
Yeah, cold outreach doesn’t work at all. I can give you a quick story on that. There are all these AI platforms that came out, like, “We can send out all your emails using AI.” I spent a lot of time doing a deep dive on this, doing it the right way, setting up all the domains and the DMARC and all the technical stuff you have to do to get it set up correctly. I had lots of different email addresses. I only sent a certain amount each day, under the limits that everyone was recommending, and had them highly targeted. And no one read any of them. I got zero responses. I sent out… I don’t want to tell you how many were sent, but a lot. And I think, in a way, a lot of these AI email tools are going to kill themselves.
Because on one hand, oh, it’s great that AI can do all this stuff and automate it. But at the end of the day, it makes it more noisy for the recipient, and they’re just going to ignore it. And that’s what’s happened. So I think there’s no future for them. I think email marketing, in my opinion, is a complete waste of time.
Nick Rybak (37:43)
Yeah, I think a lot of people would disagree, and a lot would agree with that. And on the opposite side, is there something that most people think doesn’t work, but you think it does?
Davidson (38:02)
Well, I don’t know if it’s something that most people would say doesn’t work, but I know just from recent experience with SEO, and by recent, I mean maybe within the last year or two, just really focusing on that. I think most people probably would agree that SEO is something that works, but that’s what’s worked well for us. So yeah, I think that’s the best one that I’ve got. And of course, word of mouth, but that’s sort of a different ball game.
Nick Rybak (38:33)
Yeah, Davidson, I love this. You’ve built something real in a space where most people would have given up before writing the first line of code or getting the first customer. So thanks for joining me. And to everyone listening, check out Ravetree to see what the bootstrapped alternative to ClickUp and Asana looks like when it’s built with purpose and good customer support. Thank you for being here.
Davidson (39:03)
Yeah, Nick, thank you so much. It was great talking with you today.
Nick Rybak (39:08)
Yeah, thank you. So if you enjoyed this episode, follow me on LinkedIn, follow Davidson as well, and subscribe to the B2B Marketing Flywheel podcast for more stories from founders and B2B marketers. Thank you for your attention.