From Founding to Funding, an Entrepreneurial Journey

Jonathan Wold:
Welcome to another episode of do the Woo. I’m one of your co hosts, Jonathan Wold. And with me as well is your other co host, Tammie Lister. How are you, Tammie?

Tammie Lister:
I’m good, thank you. How are you?

Jonathan Wold:
I’m great. And we have a special guest with us today. Happy to welcome Marieke van de Rakt. She is the co founder of Progress Planner. She’s a partner and owner in Amelia Capital and she’s a teacher as well.

Marieke van de Rakt:
Thank you. It’s lovely to be here. Yes. I am a teacher. I recently started teaching at a local university here in the Netherlands. So it’s applied sciences. So in Dutch we call it. So it’s, I don’t know, but then it’s marketing. So I’m teaching them online marketing, which is great fun. Yeah.

Jonathan Wold:
So before we go any further, I want to hear a bit more about the teaching. Like, what was your, like you’ve done all these things, you’ve had quite the storied career to this point. What was the impetus, like, what motivated you to go into teaching?

Marieke van de Rakt:
I had been a teacher before, but I think it’s been since my third son was born. So he’s 13. So 13 years ago I was a teacher, but then I taught criminology. I still can do that.

Jonathan Wold:
Oh, interesting. Okay.

Marieke van de Rakt:
Something different. And then I thought, okay, but I have so much experience in online marketing, it would make more sense to do something with that. But the teaching part is just something I really enjoy. So sometimes the whole online marketing world is, well, it is fulfilling. But I don’t often, often I don’t feel like I really help somebody do something and the teaching helps me give me a sense of fulfillment or it’s just fun. And next to that, I’m also now involved in local politics, very local politics, which is the same reason just to do something well outside of the online marketing world.

Jonathan Wold:
Yeah, that’s cool. I like that. So, and you probably answered that’s. You touched on one of the first questions that I had. As you look Back over your journey. You started out, like, in technology. You became a founder. You’ve done a lot of things in the space, and now you have this role of an investor and a teacher. What are some of the. The key. Some of the key experiences that, like, shaped your journey along the way. Clearly, teaching is an. Is one of those. Like, I’m sure that your interest in teaching probably had an influence on the work you did, but what are your. Like, what are some of the things that have shaped you?

Marieke van de Rakt:
Well, so I am. I’m a criminologist. I have a PhD in criminology, and I was married to this guy who started this business, and I was always helping him. And then that grew, like. Yeah, that just grew out of what we thought it would ever be.

Jonathan Wold:
Yeah.

Marieke van de Rakt:
So I. I often said before we sold yo’s, that it was all lucky that we just started at the right time. And that’s true. We did start at the right time. But now, looking back and also looking at other investments, I also see now we also made some good decisions and we made some smart moves, and there was more than just luck in what we did. I. In everything we did at a juice, but also what we do in Amelia. I like to help people to do stuff. So I think the whole SEO analysis that we built also helps people to do SEO. So before I joined Yoast, Yoast, the person, the husband, he built most of the technical stuff. And when I came along, we built the bullets and the readability analysis and all the thing that people can work with. So I don’t know, it was a lot of things happening at the same time that just drove me into a direction that there were all decisions that we made consciously, but that’s just not true.

Jonathan Wold:
Yeah, right. Right. Here’s what I’m curious about, because you mentioned the local politics. So on the one hand, you’re working in this product that is very. It’s global in nature, in a global ecosystem. Right. And then you have this interest, like, you’re teaching locally, and also this interest in local politics, which is really. I see that as a. You care about that. That local level. Right. I’ve heard it described as, like, thinking globally, like, acting locally. Right?

Marieke van de Rakt:
Yeah.

Jonathan Wold:
How does that. Like, can you say a bit more like, how does that philosophy, like, influence how you’re making decisions and investing? Like, you’ve got this broad context that you could draw from. And a lot of. There’s a lot of people who would just tend to say, well, you just think and invest and do everything global, but you have this local lens like can you tell us a bit more about that?

Marieke van de Rakt:
Yeah, I think both are important. So I’m living here in the Netherlands and I take my walks here. So where you’re living locally matters? I think so we’re now this Thursday I have to do a speech in the local politics about the yard of our castle, which isn’t important, but it is important. It’s not important for the whole world, but it is important for the people that live here. So I think that both of these things are important. So at Yoast and we still think like that, like we would like to improve the web, which is a really big thing, often too big for me to grasp. But those are things that we think about. I think it keeps you grounded to do both, that you’re able to think like really big if you’re also able to think really small. Because both of these things matter.

Tammie Lister:
Yeah, that makes a lot of sense to me. I love that kind of try. It’s really hard paying attention to both at the same time. I think that kind of zooming in and out and I think that kind of leads me on to you’ve found yourself in this kind of investment space. It’s not luck, however, it’s a lot of skill and a lot of opportunity potentially. But also seeing those opportunities, I will reflect that back and I think that’s something that we’re probably going to of discover in our conversations. But one of the questions that always comes up when people investment. Well, there’s many but is what as when you. So you’re now investing in people, but what are your non negotiable kind of criteria for really looking at invest people to invest or products to invest in? What are like do you have a checklist? Do you have things.

Marieke van de Rakt:
And now I have a checklist. Oh, what’s on the check? And I don’t know what to look for. So it depends. You can look either at a product and then you’ll get like the KPIs of you have to have a low churn and a high retention and you’ll look at the MMR of a product. All the boring things, those are important. But I think looking at a founder, I’ve learned that you need to have someone that wants to work with us. So there are a lot of people out there that just want to have funding. We. And that’s cool as well. But I don’t think that we necessarily like that because then it’s just then I think then you can just as easily leave your money at the bank because they’ll catch your profits. So. But if it’s a person that wants to work with us and wants to listen, and it’s not like you have to do everything we say, but it won’t make any sense if people just won’t want your opinion. So there has to be some sort of self reflection and an openness to work together. And that’s when I think it works. And we have some investment. Not in the WordPress space though, but outside of the WordPress space where people just do their own things. And I get annoyed by that. Not if it’s all going well, then I’ll just say okay. But if they’re. If it’s not going well and they don’t listen, that’s. Yeah, that’s bad. Then you don’t have anything to add there.

Tammie Lister:
Yeah, that’s a hard situation. You mentioned outside the WordPress. I’d love to kind of spin us out a little bit. It feels like the first couple of months of a year is always talking about the future of not just of the year, but of the next like 10, 20 years. But I really, particularly when you’re thinking about investment, you’re generally thinking about the future. You’re looking quite far forward because as you mentioned, there’s not a bank. Well, you’re not a cash machine. That’s what you’re not doing. So how do you see the future of open source evolving, particularly in terms of business models and really how an investment. And with that kind of that global local kind of angle as well. I think that’s really an interesting kind of lenses to apply to this.

Marieke van de Rakt:
Well, I think we’re. It’s hard. So open source is not often understood by investors because they think, well, but everybody can just take your code away and then you don’t have a product anymore. So that’s what I also experienced when we wanted to sell Yoast, that there was this group of investors that was just not interested because it was open source and they didn’t understand the whole freemium model. So I think the open source space has a lot of opportunities because so many investors don’t see the value in it. But at the same time it’s also a difficult ecosystem to invest in. Well, because there’s a lot going on, which doesn’t always help also I think so at least for Europe, there are laws coming up that could potentially make things more difficult. So all these things offer both threats and opportunities, I think. But for most investors, open source remains like, I don’t know, scary.

Jonathan Wold:
I Find the journey that you’re on from a founder to an investor quite interesting because I think it gives you a lot of perspective. Some of it’s going to be really helpful, some perhaps not so much as a founder yourself to. You’re going to have your own biases and things that you learned and experiences that are going to affect like how you’re assessing opportunities. But I think from my point of view, there’s no question like you going to have that experience. And now that you’ve been investing for some time, you also have what you’ve learned from observing founders who are like trying things in the space, right, the mistakes or perhaps maybe they didn’t listen to you, but they did something and it worked anyway. And that can be interesting as well. I want to bring this to the E commerce space for a moment of which and I think WooCommerce is such a great example of this because it’s such a big ecosystem and there’s not really a. There’s not one right way to like do things in the space. From your experience in talking to founders and observing like, are there any common patterns or mistakes in particular? Because I think those are helpful to start from that you’re noticing that founders make in. In this sort of e commerce space.

Marieke van de Rakt:
So what I see happen most, we want to make a course out of that because we see it not everywhere. Founders, if they have a product and they want to sell it, and usually in our case it’ll be a digital product, but it doesn’t matter any product if they want to sell it, they want to tell their customers all about that product, everything about that product. And that’s usually too much because a founder is so proud of what he’s built that if you just like take a piece out of it which solves a problem, he’ll say, or she’ll say, or they’ll. They’ll say no. It also does this and this and this. And you end up with very generic product descriptions because it does everything. But that doesn’t usually resonate with a customer because a customer wants to solve a problem. And so I see all these product owners trying to sell their product while they should be selling the solution to the problem that a customer has. And this is a conversation we often have with product owners and also with ourselves because we did the same thing with Progress Planner all over. You build something, you’re proud of it, you’re going to describe it into its fullest and end up with something that’s unreadable.

Jonathan Wold:
And yeah, why do you Think we do that.

Marieke van de Rakt:
I think because you’re just proud of what you built.

Jonathan Wold:
Okay.

Marieke van de Rakt:
I think for a developer who only thinks about their products and usually doesn’t think as much about the person, which makes sense. Right. If you’re just building something, then it’s even harder to think about who’s going to use this and what are they searching for when they search for their problem. Because often people aren’t even aware of their problems. So then you’ll have to market it even differently. So. But that’s our common thing that we see doing and we have, we, we invested in a clothing brand and in the natural skin care.

Jonathan Wold:
Right. I think that’s important to point out is that you guys have a range of investments too. It’s not just in tech like you’ve been, which I think is great because there’s things that are similar and things that are very different.

Marieke van de Rakt:
They all do this.

Jonathan Wold:
Okay.

Marieke van de Rakt:
They all do. They all want to be like, don’t forget anything about what we do. And then it become so big that people don’t understand it anymore.

Jonathan Wold:
Yeah, that’s helpful.

Jonathan Wold:
That’S changing like always and especially lately in technology for E commerce in particular, as you look at the landscape and like the investments that you’ve made and opportunities that you’ve passed on and looked at broadly, what are, I guess what are you personally excited about? Like what are the areas of innovation that you find interesting when you look at like the E commerce landscape?

Marieke van de Rakt:
Oh, that’s a hard question. I don’t particularly like AI. I do understand that it’s an important thing that’s come up.

Jonathan Wold:
Do you have any thoughts on why of that? Because I think that’s interesting. Like what is it about it that you don’t like?

Marieke van de Rakt:
Yeah, I don’t know, I’m just old fashioned. I think I do use it a lot. Well, what I don’t like, I Think that’s because I’m in the SEO space, that so many people use it to write preppy texts. If you look at Jatit, that’s the reason that. Because I also use it, but not to write preppy texts. You should use it to write something better, not something worse.

Jonathan Wold:
Yeah.

Marieke van de Rakt:
So maybe that’s one of the reasons.

Jonathan Wold:
Yep.

Marieke van de Rakt:
And AI shortcuts. AI is much more than ChatGPT, of course. So I see a lot of. I think that will. That’ll be something that will help us, well, improve websites as well. I’m just still thinking, what’s the next big thing in.

Jonathan Wold:
Well, and I would say it this way, it’s like, I’m more interested in like, what do you personally find interesting about the e commerce space? And to your point, it could be like, maybe it’s not going to be like, oh, the next AI thing applied to E commerce, like that stuff’s going to figure out, but like, maybe what led you to invest in like, clothing, for instance?

Marieke van de Rakt:
Well, multiple things. I wouldn’t do it again because I’ve learned that fashion is really bad for the environment, even if you do it correctly. And it’s still bad and I’m still proud of the brand because it is amazing woman behind it. So it’s okay. But we’re not going to do that again. I just. She does everything the way you should do it and it’s still bad for the environment. I think what I’m excited about, I think the whole world of online selling perhaps is changing because what I noticed is it’s harder to promote your products on social because these platforms are all. People are moving away from some platforms, platforms are changing. I find it much harder to get traction on socials than it used to be. It’s so crowded. And the same goes, I think, for trying to rank high in Google. And my children don’t use Google anymore. They use YouTube and TikTok and Snapchat. So that’s. I think that’s scary but also exciting because, well, we need to find new ways to find customers. But that’s really something that has changed. When we started Yoast, it’s not easy, but it was much easier to get traction online.

Tammie Lister:
Yeah, one of the things I think there is that change can be both good and bad. And one of the things in looking back at what you’ve done, you’ve really been instrumental and I’m going to give this to you. You mentioned a teacher, but you’re also a leader and you’ve been instrumental in creating some pathways for underrepresented groups in tech. What that must come from something personal. What personal drove you to. And it feels like a commitment to do that. Almost like a personal thing of like a drive to do that. Where does that come from?

Marieke van de Rakt:
So I got pregnant during my PhD. Was not supposed to happen. But he’s 18 now and he’s doing wonderfully. Yes.

Tammie Lister:
Happy accident. That’s great.

Marieke van de Rakt:
His name is really surprised in Greek. But that just led to that I was not able to follow a scientific career anymore. Not because they said I couldn’t do that, but there just weren’t any positions. And that had to do with the fact that I got pregnant and other people didn’t and wasn’t that clear? Because it’s never that clear. But it did make me change my path and I did find a path. But then I got pregnant with a girl and I was like, no, but she has to have the exact same, well, opportunities that I, that my son will have. So I think that the birth of my daughter was important, but also the things that I, I went to, went through when getting pregnant in university. Yeah.

Tammie Lister:
I guess going back we kind of had the inspiration of investors and I guess that’s also one of the things I don’t know personally for me. I look back at the next wave of people and you’re saying that like your daughter. I look back at this. What really. When you look at aspiring individuals who are looking for leadership and that’s kind of the biggest thing in open source and tech and we can try and paint it as fluffy and lovely as we can, but we have to do on realities. Right? Like otherwise we’re setting people up for stumbles and gray’s knees. Right. Like we have, we have to be true to people. What strategies and ways of just being would you recommend for anyone from underrepresented group who is looking to be in there? How do they even start and how do they strategize to do that? Big question.

Marieke van de Rakt:
Yes, really hard. I think it’s good to realize that most people are scared and you have to do it anyway. I now notice that people don’t believe that I’m scared. But I remember just before this podcast, I’m not nervous for podcasts anymore. But I used to be so nervous that it just me being throw. Throwing up before. And then if you watch that podcast because it was a video thing, you won’t see it. So it’s a lot of people fake it till they make it. And I think that’s something that people should realize that people Appear to be, I don’t know, confident on the outside, but actually aren’t. And you just need to show up and try again. If it doesn’t work.

Jonathan Wold:
Yeah, I want to take this a different direction for a moment and then come back. So, progress planner, for those who don’t know, can you give us the short, like, what is it? What are you guys trying to solve sort of in the space with it?

Marieke van de Rakt:
We’ve changed this a little bit. So the idea that came to me because I am a notorious procrastinator, so I always put things off and I thought, well, a lot of things you have to do on your website are also things that people would say, oh, I’ll do that later. So the idea behind the plugin is we’re going to help you to remember, oh, but I should do this kind of stuff. And we’re currently building in all kinds of things that help you, or you should do this and you should do this, this. And so we’re building all kinds of features that help you to set up the settings of also of different plugins. So most use plugins in WordPress to make sure that those settings are set correctly, to make sure that everything that you need to build a good website is taken care of. So that’s the idea behind it. So there’s a lot of gamification. You can earn badges if you join now. The badges are really easy to.

Jonathan Wold:
Right.

Marieke van de Rakt:
To earn now because we have to tweak that a little bit. So sometimes we have some little bugs, but I like that because now I have my March badge already, I think, which is good.

Jonathan Wold:
So first off, I can’t resist what changed in positioning because you’ve been at this for some time. So, like, how is that evolving?

Marieke van de Rakt:
We started with the whole gamification and trying to keep people on board and we got feedback. So we ask for a lot of feedback because that’s the way improve your product. And people said, yeah, but I don’t know what to do. And we gave them too big of tasks. So saying write a blog post, people would say, I don’t want to. Now we have small tasks as well that’ll just help you to make sure that your settings are correctly. Oh, you have an uncategorized post or a category without a name, you should make sure to add that. So little things, we call them Rafi’s recommendations. Rafi is the little rooster. He’s also my son. Okay. And. And he’ll. He’ll tell you what to do and then you’ll earn points. So I think the proposition didn’t really change, but we help. We are helping people more also on what they should do instead, instead of just telling them, do something.

Jonathan Wold:
All right, so this is interesting to me. When you talked about AI, like, you said you didn’t like it, but the truth is that it’s like, often how people use it as a shortcut for just, like, throwing stuff out there, right? Like, you’re making use of it and you’re building tools over here where you’re trying to, like, I would describe this as like, you’re trying to unlock people for, like, help them make progress with something. Right. And to recognize that you can plan for it. Like, you can reduce the friction. And especially if you’re drawing from your own experience with procrastinating, at least for me, I find that it’s often rooted in motivation, which is often tied to just being unclear on what to actually do next. Right. Like, oh, it’s only 15 minutes. Yeah, I could do that. Why did I put this off for so long? Because I thought it was a big, scary task. So I’m curious, and this may be at the. Like, from your own experience, I guess, where do you see, how do you think about the role that technology is best suited to play in, like, working with us as humans? Because, like, it feels like you’re. You have your own experience, and it’s also affecting the investments that you’re making and creating tools like that. Like, how do you personally think about that? Like, role of technology?

Marieke van de Rakt:
I think technology should help you, and that’s how I use technology. And that’s also how we use how Progress Planner is positioned, in my view. So there are a lot of things that you can do automatically, and then there are some things that you really have to do yourself. And perhaps you can use a tool, but you still have to do some things yourself. But we’re going to make them as easy as possible. So that’s what we do. At Progress Planner, I like to think that the human being, the person, is in charge of the AI, but that’s only if you can use it properly. So I now, as a teacher, see students using AI today. They had to do a presentation. They didn’t understand what they were talking about. And I didn’t call them out because I felt bad, but they were talking about lead generation. And they don’t know what lead generation is yet because I haven’t told them that’s in the next course. So there. And I was like, should I now ask them explain it to me? But that would Be so rough. But that’s how a lot of people use AI just randomly or use technology. And I think we should help people to be in charge of technology, which means that people should be educated or helped on how to write good prompts or how to use a tool properly or make a tool so usable that it’s intuitive.

Jonathan Wold:
So I’m curious, my last question on this. So you express the frustration with someone who goes and like, just like write an article for me and then just drops it in there, right. I think some folks could argue like, well, I’m using the tool, it can do this type of thing for me. So how do you distinguish what you do yourself versus, like have assisted? And I don’t think there’s a right or wrong. But I’m curious for your thoughts on this. Like, how do you make that distinction?

Marieke van de Rakt:
I only use AI if I could have come up with if I know what is, if I can see whether or not it’s correct. So if my knowledge is as big as what the AI writes about, you shouldn’t use it if you don’t understand what the thing is saying. Because then you also can’t really distinguish between is this correct or not? You wouldn’t know because you’re not an expert. I use it as a brainstorming tool because it comes up with crazy things that I hadn’t thought of and also as a list maker. So if I make a new lesson or create a new lesson and I write, I want to tell all about, I don’t know, social media, I will ask it and it will come up with like this list of things. And often there’ll be like two or three which I would have forgotten about if I had to make that list myself. And I know that they exist, but it’s just hard in my brain to come up with that. So I think if you are in control and you know about the things the AI writes about, then that’s okay, then you’re in charge.

Tammie Lister:
I think I recognize that a little bit in myself from someone who’s also done academic. I think it helps you with like the mind mapping, the knowledge connecting that go back to like the old school techniques, like we used to have to go the hard path with doing things like that, particularly an academic. And I really, I think that’s the psychology kind of connection as well. Right. Like trying to make sense of all these random pieces of information we normally like to finish with a couple of questions. I really want to go back to that yourself, where you had your daughter and what advice Would you now being you, now give her your you.

Marieke van de Rakt:
Well, I think up until she was 10, I don’t think she felt any difference from her brothers. And then puberty hit in and that. So that’s a big thing. And society also kicked in. So the influence from outside the outside world became better, bigger than my influence. And so I now see a girl for which I think, oh, and she’s going to do great things. But I still see what society does with women or with girls and that’s different from boys. And I don’t know, it frustrates me that they are in fact now different and it’s totally allowed to be different. But also different in sense of how much confidence she has. If you compare that with her three brothers. Because she has three brothers and I don’t know, I just help her every day and try to be a really good role model in.

Tammie Lister:
Where does your confidence come from? Like, I know we’re going kind of a little bit here, but I just like to. Because it feels like you went on a journey and you identifying through other people and that’s awesome. But you have this confidence in you exuding it. And I’m going to reflect that back at you. And I assume you’re getting that from other people and the people you are curating here. But where does that come from?

Marieke van de Rakt:
I don’t. And I don’t feel confident at all. You.

Tammie Lister:
Are you doing the swan?

Marieke van de Rakt:
Well, I know how to. I know how to present myself. So that’s. So I’m grateful for that and I learned that, but I don’t feel it. I mean, I’m sorry, but I think.

Tammie Lister:
That’S also part of it. Confidence when you don’t. When overconfidence or bravado is when you overly feel it, if that makes sense. Right. I think there’s something about humility and confidence going together is the perfection.

Marieke van de Rakt:
I think you’re right. I always sometimes say to people, no, I don’t say to people because I don’t dare them. But I often say a lot of people, oh, they should doubt themselves a little bit more.

Tammie Lister:
Yes, I, I often also have a reflection that maybe a few people should have a couple more scabs on their knees. That’s what I also think about.

Marieke van de Rakt:
I like the fact that you keep thinking about, okay, what could I have done differently? Or is this, what could I have done to prevent this? So I, I don’t see myself as confident, but I do know that I come across that way. So I’m grateful for that.

Tammie Lister:
Great. Keep rocking My last question, if you could create any product today, doesn’t matter what product teams you have, anything, what would you create? Could be physical, could be digital.

Marieke van de Rakt:
I would love to create something that would celebrate diversity more, but then it’s hard to make money out of that. And it’s also a very scary thing because I’ve done some things in that and if you promote them, you’ll get a lot of backlash as well. So that’s been the reason that I’ve not done that. But that would be something I really would enjoy doing. So I’ll keep thinking about that.

Tammie Lister:
Thank you.

Jonathan Wold:
Well, Marika, thank you for taking the time to join us. If anyone wants to connect with you, learn more about what you’re working on, what’s the best way for them to get in touch?

Marieke van de Rakt:
I’m out of social. I am on Twitter or at least I logged in today again. Okay. But I’m not my channel socials. I’m on the post that is Slack. So you can reach out to me there Progress planner and you can email me@marikerika.com I have that domain.

Jonathan Wold:
Nice. Well, excellent. Well, thank you for sharing your thoughts and your insights. It’s been, it’s inspiring to watch the progress that you’ve made, no pun intended, with our progress planner there and looking forward to seeing what you continue to do and really appreciate the work that you’ve been doing in the space in particular to to help people continue to do better with the doing so. Thank you Mar.

Marieke van de Rakt:
Thank you.