10: Re-Thinking the Educational Marketplace with Shawn Lestage of Riipen

Welcome. This is Startups Unpacked. I'm your host, Dan Hightower, founder and angel investor. Each week, I'll chat with a startup founder to unpack what they're building and talk about their life as a founder. Without further ado, let's dive right in. I'd love to hear Sean, your journey. How did Sean become an entrepreneur?

Well, I started my first company, it was a painting company while I was doing undergrad. I did that, I ran that for a while, which is— and then I ended up shutting that down for no reason except just moved on in life. But my first real attempt at starting a company would have been during law school. I studied law in the United Kingdom. I'm from Vancouver, BC, or I'm from Prince George, small town in northern BC. But I was in Vancouver at the time living and ended up going to law school in Brighton, University of Sussex. When I arrived there, there were, I don't know, 15, 20 other Canadians. I couldn't figure out how they also arrived at the same law school as I did. It seemed bizarre. And I found out about this whole world of international student recruitment. And over the course of law school, ended up starting a company called Future Projects, which I ran for a number of years and ended up selling out to the other shareholders. And one of the co-founders in particular. And so that was 2013, I think, and sold that in about 2016 towards the end of the year. And then went to finish up sort of the legal career path, as you will. Like, it's a bit different in Canada than it would be in the United States. You do the bar exams, you just start a big period. So I did that piece at a national law firm here in Vancouver. Really wasn't interested in kind of being in that space for too long. I was doing securities due diligence for like raises and things on like pink sheet companies and things that were not overly interesting for me. I was aware of Ripe in this company that started similar times to that future project I'd started, and I actually remember seeing the crowdfunding opportunity when they were just kind of at the ideation stage and thought it seemed interesting because obviously, as it— for me, I had gone to law school and then Quickly realized, oh, this isn't a career path I'm interested in. Maybe, maybe had I received some actual experience at a law firm or understood what a lawyer does on a day-to-day basis, I might've changed course sooner and saved a ton of time and money. So I ended up applying to Ripen. And that was about 2, a little over 2 and a half years ago now. And I've been here since, helping them build, build this company. I think I was, we were about 20 people then. We're about 80 employees today.

Great. What's your role there?

Director of operations. So we have a, we've got a 6-person executive team, our 3 co-founders, Dana Stevenson, Dave Savory, Jordan L., and then myself, Emily Mashing, and Dr. Karen Bacher round out sort of our executive team. And then from there, we've got the organization, pretty rapid growth over the past couple of years.

Yeah. Before we get too deep, I'd love to, I'd love to, before we get too deep, I'd love to hear what Ryken does.

Yeah. So we're eliminating graduate underemployment. We're— that's our mission. What we've created is sort of this cloud-based marketplace that connects employers directly with university academics to create experiential learning opportunities that then becomes part of the curriculum. And so if you think about, if you think about higher education, and if, if for anyone who's listening that studied in university or college, and you remember doing a case study or a book report or whatever it might be, a group project. Rather than doing that necessarily in the abstract, you're now doing it in collaboration with an employer. So you're getting a real project that is— that matters to an employer. You're working on that, you're applying what you're learning in the classroom immediately, you're getting feedback on the academic outcomes, and you're getting professional feedback on your soft skills and on the deliverables. And so it's a 3-sided marketplace, but obviously the way Ryden's been designed is that With, with the understanding that students who are enrolled and taking classes are a very captive audience. So the completion rate is significantly higher than if you're trying to do maybe co-curricular opportunities that are outside the classroom. This sort of drives them towards and adds additional value to the academic journey.

Yeah. So you talked about— I'm going to use your words here. So, so you talked about the skills gap and then like labor, labor deficit problem. Let's dig into that. So So, you know, I went to college and after college, or I guess towards the tail end of college, it was back in right when the Great Recession was full steam. Yeah. There was some concern about finding gainful employment, and we did do a couple little projects for some large, like, Fortune 500 companies, a way to drum up potential job opportunities. But it was highly unstructured.

Yeah.

And nothing came from it. So I'd love to hear you frame up that problem and how you're solving it.

Absolutely. So when I joined Ripen, I remember reading a report from the Royal Bank of Canada. We're a Canadian-based company. At the time, we were largely just in the US or within Canada. And that report stated that in our country, which is about 35 million people, it was costing $40 billion a year to upskill new graduates to— in order to, like, who had just finished their undergraduate degree, so that they could do the jobs that they were being hired for. We just did a green paper with Emerge Education, which is a VC in London, and Jisc, which is a tech partner for the UK higher education sector, and Nick Petford, who's the Vice Chancellor of the University of Northampton. And in that paper, it's— there's there's information about the global skills gap and labor deficit, which is projected to be something in the range of $8.5 trillion annually by 2030. So like the scale of the problem is enormous in terms of students and all really workers not having the skills that the labor market needs to operate effectively. And so looking at that, obviously there's a big challenge because you start thinking about, well, why do students go to university? Why are they entering college? Why are they— what's their outcome that they're hoping for? And almost invariably, if you survey them, as has been done even at a place like Berkeley, I think something like 85% of students indicated that they're there because they want to get a better job or they want a certain career outcome. And I think on the opposite side, previous to, you know, in past years, And it's improving dramatically, but it's not the same response from the institutions. That's not the role that they see their place in society as achieving. And so you have obviously a mismatch. And then within that, you're gonna have incentives that are pulling people in misalignment. And there's a number of issues around that. And so what we're trying to do is look at how do we align people's incentives and motivations through this platform that improves student experience, provides them with a professional network, the opportunity to develop skills, the opportunity to fail in a safer context, like, and then at the end of it get validation that they can add to their resume or CV. For the educator, it improves the teaching experience. Hopefully they've got more switched-on students who are engaged and excited about what they're learning. They're applying stuff, the theory, immediately getting feedback. And for employers, they're identifying talent They're developing talent, they're improving, they're getting brand recognition, they're building out a more diverse talent funnel, which has never been more important. And they might find talent in places they're not looking, which is certainly something that happens on the Ryden platform. And the idea that like at scale, we started this platform ecosystem in 2015 with 2 institutions. We've been growing fairly rapidly. And you can see like, I think we've delivered 65,000 student experiences in the past 2 years. And as that continues to grow, you know, it's just that the momentum has been enormous in terms of seeing the growth of student experiences, the number of employers coming in. You know, when COVID hit, there was a lot of challenges. We saw certain spikes, which a lot of companies in edtech did, but you would see that we had a 1,200% or 1,100% increase in the number of employers signing up to our platform, which was just Mind-boggling.

Whoa.

It took us 3 years, I think, to get 75 institutions to try our platform. It took 6 weeks to get 75 at the start of COVID who wanted to pilot and test this and figure out ways to deliver this at scale. And so, you know, we think that we can make a dent in that huge problem, but it's, it's certainly going to take more than just our solution. There's a lot of solutions in our space that are working to address it.

I mean, that's crazy. So, so, you know, as a student, you select a university today largely based on a couple factors, one of which is like ranking. Did I go to a good school based on some trusted list?

Yeah.

Well, that could change here though, right?

Yeah. Yeah, I mean, it's, it's interesting to think about, uh, how you— like, for me, speaking personally, when I chose where I wanted to study in the UK. I applied to a number of law schools. I was accepted to a few of them, or most of them, I think. And my intention— I was going to go over there and I was going to look at a bunch of schools, and I ended up going down to a city I thought was cool, and I was— this was good, it was ranked high enough. But I didn't even consider, like, when I— and I was old enough, I should have certainly at that stage of life been considering outcomes. But I think a lot of students do that. They'll choose an institution based on reputation or perceived reputation based on exactly some, some list, some that they don't understand or haven't looked into the complicated way in which rankings are arrived at.

Yeah, and the ranking is just like, it's just supposed to be correlated with job outcome, right?

Yeah, well, it depends. Like, there's a number of different rankings, of course. There's, there's employability reputation, research reputation, research output, impact on your local community, national community, international market, research funding. Yeah, there's like that. And you can, and then, and then there's maybe like an aggregated ranking of all of them. And then there's faculty rankings and then there's degree rankings.

Oh my gosh.

So you can really, you can really, you can really frame it however you like and convince yourself you're making the best decision. But ultimately, if all the students are, are not all, but if the vast majority of students are saying, I'm going to university or college because I want a better career outcome, that's probably the ranking they should be looking at. Yeah. And then how is the institution going to facilitate that or support that journey? And I think that's kind of where we see we can add a ton of value for students, institutions. And, you know, interestingly, most of our partners, if not every one of them, has already been doing this. What we're trying to do is enable them to do it at scale. And, you know, they're— it's expensive and challenging to build these opportunities. It's— and there are varying types of opportunities within sort of the work-integrated learning, which is kind of what we call this, an experiential learning space. You know, there's placements that could run for 8 months in the middle of a degree. There's summer internships and all the rest of it. Those are extremely valuable, but they're expensive and hard to set up. They're hard to source employers, and, you know, our marketplace, we have, you know, our community of employers is roughly 10,000 with 50% of them being active in the marketplace.

Yeah.

And so it's a lot easier to source those, and then, you know, when students are looking for opportunities, they can see, oh, this is a school that's using XYZ technology, hopefully Rypen's part of that tech stack, and they can then look at, oh, what does that provide me during the course of my degree? Oh, I'm going to get to do You know, I'm going to go do my MBA at school X and school X is going to have 4 options where I'm going to graduate with a great degree and I'll have 4 job experiences. I'll have a network on my resume before leaving. So

like actual job experience. Yep. And then I guess, what's it like being a Canadian startup?

What do you mean?

Well, I don't know. I hear great things. I hear advantages all the time, but I'd like to hear your like, I

mean, it's— I don't have a frame of reference to measure, it's like to benchmark it against really. It's great. We're in Vancouver. We have our team, as I said, is we're a remote-first company. So like our, of our 80 employees, maybe 35 or so are in the Lower Mainland, British Columbia, the Vancouver region, and then kind of throughout the rest of Canada with, you know, maybe 20 employees in Toronto. But obviously similar to every other company, when COVID hit, we just immediately went fully remote, which has been fantastic and allowed us to start hiring talent in places we might not have been able to previously because we're no longer concerned about where people live. Yeah. So funny enough, we're seeing, we're actually hiring, and in part as we're focusing on the US over the past 12 months and continuing moving forward, you know, we're adding a ton of, US team members to the company and all of our investors are, not all, but our VCs are all Americans. So,

okay. Yeah. So like you, you're adding team members because you're sensing this traction, like especially all of a sudden. Yeah.

I see traction right behind you as well, by the way.

Yeah. Yeah. On the bookshelf. Do you remember thinking back that moment where you realized, oh, this is actually like, Real traction. You mentioned a certain number of customers that it took like 3 years to get, and then all of a sudden a ramp occurred. And I'm curious if that was the moment or if it was a different one.

Yeah. I mean, we've thought a lot about this internally and like, I think like that traction point, certainly we are, we are feeling a pull from customers who want to use our platform. And it's, it's interesting because it's, we have very different, like very segmented types of customer groups. We might in some instances have an institution-wide agreement where the large, you know, the decision makers and the drivers of the partnership are the very senior leaders within an institution. We'll have deans or associate deans for a particular faculty, and in some cases we'll go straight to an academic or several academics at an institution for what we call a student access model, which allows them to pilot it at a fairly reasonable cost. And, and so, but what's interesting is, is we're starting to get A significant number of referrals, and there's a lot of buzz around what we're doing. We're getting a lot of support from foundations and grants, federal, provincial, which is kind of interesting and quite exciting. Kind of going back to your earlier question about being a Canadian startup in edtech, it's very helpful. There is a significant amount of innovation in Canada in this space, and there's a lot of non-dilutive capital available. Yeah, like, you know, we've had access to a lot of it and it has really, really acted as a catalyst for the marketplace.

What are those programs? Are they just educational support programs or like employment?

Yeah, so they might fall under a few categories. There's like employment skills development, there might be something, you know, related specifically to experiential learning or changing sort of— in fact, even in Ontario, our largest province, there are recent mandates or recent legislation that is requiring work-integrated learning or experiential learning to be a part of graduating from higher ed. So if you don't have it, you can't graduate, which means every institution has to do it. And obviously, when you legislate that, there's funding that comes behind it to make it possible. And so it's created sort of this like groundswell for us to to really capitalize on it and grow this marketplace for students.

Cool. I mean, that's, that's a huge benefit right there. And then, you know, from a— what, so like from a COVID perspective, well, hold on, let me reframe the question. So it's like the initial traction you felt, what, what is behind that? What is driving the institution to feel like they need to move to a more project or outcome-based Approach?

I mean, I would be a little hesitant to speak to the specific motivations. I do think, though, that there's— there is a sector-wide recognition that university and employer collaboration is key to delivering value for every stakeholder, whether it's students, the academics, professional service staff, the regional community of employers who are already partnering university network, national, you know, enterprise global companies that are recruiting and all the rest of it. And facilitating those collaborations has been happening, obviously, for as long as universities have been around. It's just been difficult to do and not easy to scale and expensive. And so I think, you know, the idea is that as that improves, there's more value added to everyone who's participating in higher education. And so I think, yeah, that piece is driving it, something around that piece. It might be different for an institution who has, you know, for a different type of institution. So a world-class research institution might have a different take on what they think is necessary or will add the most value for them relative to sort of maybe a trade school or a community college, and they might have a different focus. And so in terms of how they're answering that. that question. But for us, the traction and the pull has been often, I think, from when people use the platform. What we're— what our core competency, what we're really great at, is making that connection. So, you know, you simply just post your course or your class into the marketplace or some piece of the syllabus, and you start getting requests from employers. And those employers might be in San Jose or Toronto or London. Or wherever. And that's an opportunity that, you know, it's just, it's very easy to use, it's simple. And then secondary to that, or not secondary, but like complementary to that, would be just the student experience. So students are getting these opportunities. I've been in a few kind of closing calls, if you will, where students are actually part of the conversation with the Vice President Academic, and they're asking the students who have been been part of the pilot, what was this like? And the feedback's been exceptional, you know, and genuine where they're saying things like, this has been the best class I took in my master of finance course or whatever it was, because it was the most relevant. It felt real. I was doing a problem that mattered, you know, and I'm getting feedback from an employer that then can add to my resume. So yeah.

I remember some projects in college, I felt like didn't matter.

Me too.

All right, so we met in On Deck Writing, which is, if you think about it, a project-based learning environment. If you consider writing a project, right? Which is this, this movement, this part of this larger disruption of the education system going in the direction of like small community-based Learning, and I feel like what you're doing is enabling institutions to participate in that movement. Because projects, I assume, in your platform aggregate some number of students to work on them. They're probably not solo acts.

Right.

Just like On Deck does, and it seems like a super cool strategy. If you're the institution, you've got to be looking at On Deck and scratching your head. and wondering, is On Deck gonna roll out like On Deck statistics or finance next and it becomes like an actual like curriculum? That could be wild or extremely disruptive. So that's pretty cool. I'm not sure if you guys see it that way.

Yeah, I do. I've been following On Deck. I mean, I came across On Deck on Twitter, was immediately intrigued by what they're doing. Because it is everything you've just described. And having done Riders with you, like, the experience of having access to the community, the network, there is certainly like, in a very short time, they have managed to deliver brand recognition somehow. And like, the FOMO experience of people who want to be a part of this community, and they want— they think it's cool. And so there's something there that's Like, for the upper echelon of higher education, those brands, I'm sure they must be aware of it, I would imagine. I think that what Raipen's doing though is— there's kind of two schools, I suppose. You could take the view that higher education can be displaced. It can be disrupted for sure and changed. I don't know that it can be displaced. I think that without— like, even if you consider COVID to be a seismic shift of how higher education landscape, which it certainly is, But if you were to take a step back and think, well, this is still not displaced, enrollment numbers aren't nearly as down as people expect that they might be. There are certainly challenges. And I think just the way that funding models are set up, legislation, and sort of the— if you think about it as like a distribution model, like they have the best distribution and access and recruiting system in the world. They have built-in reputation, built-in relationships, and a huge institutional advantage. So I don't— and I think where Riipen fits is like we just get to add value and help kind of reshape that so that the outcomes can be even better for students, for academics, and for stakeholders. And in some cases much improved, because let's like, let's be real, that in some cases the outcomes aren't where they need to be. And if they're not improved, there will be problems. And I think that that's something that's exciting to be a part of, that sort of a change. But I think that like also things like On Deck are 100% needed because you HighRed's not right for everybody, and On Deck is like a fantastic opportunity for people who are wired that way and want to go do cohort-based learning. And there's tons of other startups in that space, like in the cohort development, which are, I think, going to be pretty transformational.

Yeah, absolutely. So you've added how many team members recently?

In the past 18 months, I think we've— we were 20 employees, we're about 82 now or something in that range.

Let's talk about those growing pains. What have been the top 1 or 2 growing pains adding that many people?

Well, it was, I mean, the growth, we felt some of the growing pains just, you know, like in the company rhythm of how do you manage 350% growth in headcount, department growth. We have first-time managers, we have, and we're integrating senior team members. We are figuring out how to do proper financial reporting. Like, you know, there's just kind of the regular growing pains, I think, of any startup. And then COVID hits, and then we have to figure out business continuity and go completely remote and facilitate that. So we have a young team, some of, you know, as you might expect, or in most tech startups, you skew younger. For us, it's very young. A lot of our employees feel personally the problem that we're trying to solve, that skills gap. They feel like they wanted better outcomes from their degree. They see Riipen, it's like, oh, this is fantastic to be part of solving this problem. I'm personally feeling, and that's amazing, but they're also learning to work for the first time, learning to, you know, and that's— it fits with our ethos as an experiential learning company, but it's challenging. It's challenging to do when you're fully remote and like you're just getting to know people over Zoom, you're trying to mentor and develop talent while at the same time trying to, you know, hit your quarterly targets and do the rest of it. So— Yeah. There's certainly been some growing pains, I think. One of the things that's like, I'm really, really proud of about Riipen has been the support around mental health for our team and like the opportunities for that. Like, we've had professional psychologists come in and speak to the team. We've had, you know, we do a lot of events to support people. We have our CEO, Dana Stevenson, gave a very memorable talk at our last all-hands just about mental health and taking care of yourselves and just Just even recognizing to the team that these are unusual times, obviously, but like, this is challenging. It's okay if you take time. We don't want anyone burning out. And I think that that's something that's been exceptional.

Yeah.

Yeah.

Part of that is, you know, part of that burnout is my desk here is 20 feet from where I relax.

Yeah.

And I also, I don't know about you, I'd like to hear from you about how Since we're both in ODW and both in startups, turns out the podcast is not my day job. How do you think about things like ODW as either additional work or in a balance mechanism?

Yeah, I mean, for me, ODW is definitely not additional work. It's like, it's an incredible outlet. I wish I had more time to

Yeah,

to be a part of it. And I've missed a few fireside chats with like Austin Reef from Morning Brew. I really, I want, I was only able to attend 30 minutes of that. I wanted to be there for the whole thing. It's super intriguing by what they're doing.

Yeah.

Yeah. And just writing is therapeutic for me. I'm personally in recovery. So the writing process and what I'm personally writing about has been, it's been huge for me and my, my personal growth, my development, and Honestly, like my personal, my professional performance, my ability to contribute at Riipen has improved, as you might expect, dramatically. And ODW has been a huge part of that for me.

So. Yeah. I had a chance to, through ODW, read some of your content about your personal growth. And I don't know if you want to talk about that, but that is such a common experience for people.

I mean, yeah, the, the, I won't go too much into it, but if anyone wants to check it out, it's, I'm writing a blog about To my recovery from cocaine addiction. So I've been—I was using cocaine for ten years, and like my life was spiraling personally as a result, and decided to—I mean, the process of recovery is messy, but for me, this—I think if you can't answer the question, why did I relapse last time? You're pretty likely to relapse again. And for me, I was able to do that recently, and I think. hopefully unlock some really positive momentum. And things have kind of been working really well. And the writing through On Deck has been therapeutic, it's been transformational, it's been scary. Yeah. And I decided to just do this in public and reveal because I've always felt that, you know, in sort of this pre-stage of like deciding I want to stop doing this, I want to change, and then you start looking at other people and there's all these fantastic stories But it's people who are 25, 30 years in recovery. And for me, I look to, you know, people who've built companies, creative people, people who have been successful in media and like, and then have those things. And I always wonder like, well, what did it look like in year 1 or 2 or 3? And like, why, what impact might you have on people if you just were honest about where you're at? And I'm really—

Yeah, I mean—

And for me, it's been, it was, so it was really scary. And then I decided, you know what, I'm doing this. And so, and also like, it's the purest form of accountability ever.

Yeah.

Like, there's, it's, you just have to do it. And so I did that and I talked to my CEO right then and I told our whole leadership team and that was terrifying. And then, you know, there's just, there's just like these validation points. It's like, oh, this is the right thing. And then you start real, and then you start getting messages, or at least I've started to get messages from people. who have said, hey, this is really helping me, thank you, like, you don't know the impact you're having. And it's been a wonderful thing to know that like the little thing I'm doing matters to somebody out there and it's helping them a little bit, and that's great. Because I remember reading people who were in a similar place or doing that. And also, I just wanted— for me, I felt like, well, if I'm an executive at a VC-funded startup. Why, like, it's important for people to know that, like, this is where I'm at personally, especially with our company. It's important for people who work at Ripen, who report up to us in leadership, to know that, like, there's real people here dealing with real-life problems, and you likely are too, so it's okay. Like, let's— I really like the idea of being able to bring your whole self to work and change sort of the dynamic dichotomy between professional and personal life. I think that it's— That is such a cool concept.

Yeah, the— so you, you build in public, you see people building in public all the time. It's sort of a common phrase now in startups. They're referring to their startup, but there's also this like building in public that you're doing personally.

Yeah, yeah, I call it recovering in public.

Recovering in public, that's amazing. Yeah, and too often we just highlight the, the building, the startup in public. So the focus for you is, it's a dual focus really.

Yeah, absolutely. And like, to bring it back to Ripen, it's, I don't know that I've, I can't imagine working at a better place for this. Like the, I'm sure there are a lot of great companies that would be as supportive and as, yeah, just as supportive as Ripen has been, but My experience here has been exceptional. I love the team. I love the company. I love what we're doing. And I love working at a place that's solving a meaningful problem and that embraces— our whole team is able to come and show up as themselves. And it's created a really, really tight-knit group of us that are trying to solve something we care deeply about. And so, yeah, it's great.

I keep reading in multiple places and hearing on podcasts from really influential people that some of the best operators in startups are people who have gone through some shit.

Yeah, yeah. It's usually one of my interview questions with prospective team members is like, what have you failed spectacularly at? And I usually tell them like, I'm not looking for a prepackaged story. I wanna know actually something you failed at and like what happened.

Yeah,

yeah,

yeah. And, you know, being public, like recovering in public, is like this huge example of that, right?

Yeah,

he's a huge example of like having gone through something that at the time is like really personally hard, but it is informative for how you did— you handle work-related difficulties, right?

Yeah, I mean, it, it puts the stress of like professional life and trying to build the company into perspective. So

yeah, and doing so openly with your team is like, it enables your team and others to like see how in perspective you have things. It's like, on my spectrum of hard things, this is not one of them.

Yeah, this ranks fairly low.

Yeah, that's great. That's super cool you're doing that. Where can people You know, read that personal level content.

I am blogging about my journey if anyone's interested. Letterdrop, which is a company started by an On Deck writer, actually. It's Letterdrop, My First 365. It's M-Y-1-S-T 365. Yeah.

I'll include, I'll include a link in the newsletter.

Yeah. Great.

So switching gears a little bit. Ripen's raised, let's see, Ripen's raised, shoot, I just had the note, it's gone.

That's all right. Yeah, we've raised about $7.5 million. Our seed round was Canadian, so say about $5.75 US.

So Ripen's raised $5.7 million US dollars.

Yeah.

Were you on board when that happened?

Yeah, I joined Ripen, we were kind of a pre-seed company. And then we raised, we were, we were, as often startups are, we're looking at our runway in the face and had some trying months. And then we ended up kind of pulling through and starting to see the traction we were just talking about earlier. And then we raised our seed round last September, led by Chantal Garvey and James Kim at Reach Capital and Ryan Craig at Achieve Partners. and Jessica Hinkle at Strada. So super exciting. They're all on our board now and adding a ton of value, opening up a ton of doors for us, which is great. And Ryan is a prolific writer in Forbes and elsewhere about sort of last-mile education and the need for higher education to be transformed to provide better outcomes and all of that. So he's a big champion of what we're trying to accomplish. And yeah, they've been great.

I have a question for you as a I guess you're not technically a founder, but you were a really early employee. Is that accurate? Yeah. So I'm always interested to hear from non-founders but early team members who are along for the ride from pre-seed all the way up to current, how their job in supporting the founders during the fundraise changed. Sometimes they're like super small companies, you may not be a founder, but you are like definitely in the ball game when it comes to fundraising process. And so Other times the founder locks himself in a basement and goes out and fundraises and nobody knows what just happened. So like, I'm curious from your like non-founder perspective, how you were asked to support it early and then how that changed later on.

Good question. So a bit different because of like the legal education and background. So when we were going through a raise, I think I probably had maybe more of a role than I might've expected in supporting that aspect of it, doing a lot of the reading through the agreements, organizing things that needed to be taken care of on that end, intellectual property and that sort of stuff. But in terms of the actual conversations with VCs, fairly limited up until we had a market had been created and we were getting visits to Vancouver from VCs who wanted to meet with sort of the senior leadership team. And so that process was interesting. They— we essentially were all interviewed individually by the VCs, you know, understand our role, understand, you know, kind of our background, what we're doing on a day-to-day for the company, and, you know, ambitions and all the rest of it. And so that was an enjoyable process to be a part of. And then Yeah, I mean, nothing really more than that. Dana and Dave, so we have 3 co-founders, as I mentioned, Dana and Dave largely were driving forward the raise, kind of how you described, like from a bunker.

Yeah.

And then would kind of pop up, fire off orders, need this, this, this, and this, you know, and then my responsibility would be to go get that done, whatever it would be if we needed to documentation to be organized, you know, and that was just, that fell to me. And then once we raised, you know, helping just kind of the relationship at that point has become more of a, maybe not a dotted line, but there's been a lot more communication for our senior leadership team with our investors around certain things. So— Super. In many ways, Reach has been fantastic in making, as you described, like the earliest employees, especially those of us in senior leadership, feel like we're part of the founding team, inviting us to, in fact, with COVID even inviting us to Founders Day, which was done virtually through Reach, inviting us to networks where, you know, they have professional development talks or whatever it might be about burnout, how to do certain things, how to properly set up your SaaS reporting, whatever it might be. They've been a guide for several of us. Product ops and down the line.

So the request would come to you from the bunker and then you would have to execute. So I'm curious if you could go back and do it again, what would you have recommended that the team have prepared sooner so that there didn't need to be the scramble? Not that it was a scramble, but not

Oh no, it was a scramble.

Okay, it was a scramble.

I feel like it's always a scramble, but like at that stage, it probably— it'd be weird if it wasn't, maybe. But I do think that like, this is not new advice, but when you're setting up your company, just make sure like the paperwork matters. I know it doesn't seem like it matters, but it's really difficult, especially if If you've lost team members, that was one of the most challenging things is like if team members have left and they have incomplete paperwork around IP transfer or assignment and those sorts of things, tracking people down for that stuff is, it's a small thing, but it's time-consuming. It stalls momentum. And like, I don't think you want to be in a situation where you're the one holding up a deal and you're trying to raise millions of dollars.

You're essentially talking about data room, right? I

mean— Absolutely. Yeah. Like that needs to be organized.

Did you use Dropbox or something for it?

We used Sync, actually, sync.com. But I did find as well though, that like, we might've faced a few more hurdles in being a Canadian corporation, getting investment from US VCs.

Really?

So like the, you know, at one point we did have a US subsidiary, which we ended up winding up because it wasn't the right time for us to hit the market and so on. created a few of our own hurdles.

So— Got it.

Yeah.

What was in that first data room for that pre-seed raise?

Like just a list of documents?

Yeah, yeah. Like what— I guess what gets added, what was in there for the first raise and then what is more important to have in subsequent raises?

I mean, well, the first raise is kind of largely around documentation, employment contracts. example agreements with customers, template agreements, assignment for IP, business plans, bios on people in senior leadership, financial projections, you know, 3— looking 3 years out, rough, and like, and that's the stuff that is getting— is more important as you move towards Series A for us, obviously, is like fine-tuning our unit economics, fine-tuning our metrics, and understanding that like what the drivers are. How, you know, are we on a path to becoming, you know, hitting sort of sector benchmarks for your SaaS KPIs, whether you're ARR, your CAC, whatever, like whatever those might be that are most relevant for your business. Yeah. And like, and for us, I think at the seed stage, you certainly have to have that information, but I don't like, I don't think the due diligence from my perspective, obviously I wasn't as intimately involved as the founders, But I don't think the due diligence on that stuff is as onerous or as intrusive as it will be at Series A or beyond, of course. The expectation is that you've nailed that by that point.

Yeah, it's like these are the hypotheses, right? And

then— This is our direction of travel for us.

Yeah, yeah, yeah. And then if you can think back to the height of the fundraising activity, What percentage of your time during the day was like the scramble for, for that? Because it's, it's interesting because like all of a sudden you go from focusing on your, your goals, uh, 100% of the time to some other percentage of the time that's not 100%. And I'm curious what that percentage was for you.

Maybe 25 or 30 was like focused on that. There was support, like it wasn't— at that point, we were still in headcount rather small. And so there was, there was probably myself and Emily Mashing and Karen as well, that were very involved in supporting that with various things. And I would say 25 to 30% for all of us. But I mean, for, for Dana, especially Dana, like He was getting on planes left, right, and center pre-COVID just to go for a meeting in Washington or a meeting in New York or a meeting in San Francisco or like whatever it might be. And it just seemed like it was an email at 3 o'clock and he'd be on a plane at 6 to go. Yeah. To try and go find the money and keep things moving.

Cool. That's awesome. So you're a non-technical team member, right?

That's right.

How do you think about interfacing as a tech company? How do you think about your role and I guess your responsibility to learn or become more technical, or is that not something you're really concerned with?

It's an interesting question. I think that like my value-add to Ripen is certain— is never going to be technical, and largely like that's okay. We are— and at some point maybe Ripen will outgrow me because of that, and that's probably fine. But ultimately, like, of our founders, only Jordan is technical. Strictly speaking, you might even describe us as like a tech-enabled service at this stage.

Yeah.

And I'd say it's kind of in my wheelhouse. A lot of the value derived from using Riipen is the service delivered by our CS team to customers, to students, and, you know, the onboarding experience, the check-ins, and all of it. And like, A lot of it, there's even like course design specialists that work with academics too, and the platform as well, to reshape their syllabus or into an experiential learning opportunity that sits in our marketplace. But yeah, I've done a number of things at Riipen. I've done academic sales, industry sales, community partnerships, and strategic partnerships.

Yeah, I asked the question, it's always just so interesting to like, do non-technical team members feel pressured I don't

think so

at all. To become more technical, and I don't think it's necessary. A lot of non-technical team members or founders seem to have this, like, I don't know, intrinsic motivation to, like, fill a gap in their skill set.

Yeah, I don't— I'm pretty confident in my skill set, like, personally, and, like, I feel like I add value, and I'm like, I don't have the time nor really the interest to go become technical and be a 3 out of

10

or a 4. Like, what, I'm not sure what value I'm going to add. And like, of course, like you do learn being involved in a tech company, but you know, to add value is an entirely another thing. So.

Yeah, totally. All right. So we're coming up on time. Is there a tool that you use? Maybe it helps you go remote, like Slack or something like that. That's like, been, you know, you feel like it gives you an unfair advantage? And it could be the, you know, you mentioned earlier the team-wide mental health stuff.

No, I do think so. Like, that's the team stuff, I think, is an advantage and the culture at Riipen. The unfair advantage, I think, is our marketplace. So we, when Riipen started, this idea of experiential learning and collaborating at scale in this way wasn't something that was done. And so it felt like pushing rope. And obviously when you hit a tipping point in building network effects, you start to see a different type of traction and usage. And we're feeling that. And I think that that is our unfair advantage. It is the time to value for customers using our product when they create their first project or they publish their first course. that match happens, you know, it used to take 6 to 8 weeks, now it happens in 4 to 6 days. And, you know, our connection rate used to— our successful match rate used to be 65%. Well, now it's over 90%. And like that is our unfair advantage because it just continues to get better and better. And then when COVID hit, we saw spikes on both sides of the marketplace. And for us, it's a bit different because there are a number of companies offering really valuable solutions to us, but they're Similar, in a similar space to us, taking a different approach certainly, but not leveraging the value of a marketplace.

Right on. All right, so wrapping up here, is there anything you want listeners to know or be thinking about?

Yeah, I mean, just kind of continuing on from that, like every small, medium business, which is the 85% or so of the industry users of our platform, Our small-medium enterprises, they're going through digital transformation right now, trying to figure out what, what this looks like moving forward. Our platform gives them a very, as I was saying, a really, a really quick, really easy, and really valuable way to connect with students.

Awesome. Well, this has been super fun, and I hope we stay in touch. I'm sure we will through either this or ODW.

Absolutely. Thanks, Dan.