The Ups and Downs of Entrepreneurship

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Welcome to the Business Gay podcast, where we talk about all things business, marketing, and entrepreneurship. I’m your host, Calan Breckon, and on today’s episode, I have Entrepreneur Ryder Damen. Ryder is a creative technologist, content creator, and the CTO of Cashe, a brand new Toronto startup in the fashion resale space. Ryder is bullish on taking big risks and reaching for delusional goals. So let’s get a little delulu with Ryder and being an entrepreneur, shall we?

Hey, Ryder. How’s it going? Welcome to the podcast.

[00:01:19] Ryder Damen: Thank you. Great to be here. Doing well. How are you?

[00:01:22] Calan Breckon: Good. I’m really excited to dive into entrepreneurship with you, so let’s just get right to it. How long have you been an entrepreneur for?

[00:01:30] Ryder Damen: Oh, my gosh, not very long, actually. Um, I think I’m one of maybe the newer entrepreneurs you might have had on the podcast. Uh, seven months, officially. Uh, yeah. Not very long. No, no, no, no. Um, but the thing is, I’ve kind of been dabbling in it for quite some time. Um, both my parents were entrepreneurs. I’ve worked in startups continuously, and then when I was doing startups, I was always, always doing, like, a side hustle type of thing, and it was just, uh, it was always drew me back in, you know? Like, every time I was working a full time job, I kind of felt like I was missing out on, like, the potential of. Of being in entrepreneurship and everything.

[00:02:13] Calan Breckon: Yeah.

[00:02:14] Ryder Damen: Yeah.

[00:02:15] Calan Breckon: Cool. So you’re a brand new entrepreneur, but you’ve been around it for a while. You’ve worked at startups. What’s your background? Let’s fill people in a little bit about your background so that they know what you were doing in those other kind of ventures that you were part of.

[00:02:29] Ryder Damen: Oh, my gosh. Yeah. Okay. My backgrounds are, like, really, really varied.

[00:02:33] Calan Breckon: So let’s go the technical route. Like the technical kind of like coding and that kind of stuff.

[00:02:38] Ryder Damen: Sure, sure. Okay. So my educational background, nothing to do with it. If you want to know what that is, you can look on my LinkedIn. But technical, I kind of started in code, in actually, like, graphic design and front end stuff. I started dabbling, and through there, I kind of worked my way into full stack engineering and then into backend. And then I really found my home in infrastructure, cloud infrastructure, specifically. It was like a kind of beauty to the simplicity of it, and it’s often regarded as, like, the hard stuff or the scary stuff. And I kind of liked that challenge. So that’s what I was doing. I was helping do big cloud migrations. I was helping companies power their AWS accounts, their GCP accounts before I left my career and made the jump into full entrepreneurship.

[00:03:26] Calan Breckon: Okay, so you were already playing well in the field and understood a lot of the technical stuff about being an entrepreneur before you actually took the jump into entrepreneurship. But how’s the jump been since you jumped into entrepreneurship?

[00:03:39] Ryder Damen: Oh, my gosh, it’s crazy. I thought I knew what it would involve, but it is nuts. Like, just absolutely bonkers.

[00:03:48] Calan Breckon: So why do you think it’s important? Because I’ve heard you say this before. Why do you think it’s important that entrepreneurs need to be a little bit delusional?

[00:03:56] Ryder Damen: Oh, I love, I love, I love this question. It’s. I don’t know. Because you have to in order to make it work, right. It’s like, the way I think about it is, like, you have to be a little bit delusional to be able to leave your job and to be able to think, like, yes, I can do this. Like, yes, I can jump into this and start a business, and I can make it work. And. And you have to be delusional to stay in it when the going gets tough, because it gets tough immediately. And we were talking about this just before. It’s like, every day is a rollercoaster. Like, ups and downs. And, like, Monday you feel like, oh, my gosh, I have the greatest product in the world and I’m doing the best thing. And, like, Tuesday, I’m like, what am I doing with my life? Like, what’s happening here? And in order to stay on that roller coaster, I think you. You have to be delusional because, like, a non delusional person isn’t going to choose, like, these huge stresses to their life, you know?

[00:04:54] Calan Breckon: Yeah, 100%.

[00:04:56] Ryder Damen: Yeah. And then I also think, like, entrepreneurship is constant nos and constant rejections.

Yesterday we got denied from startup incubator that we wanted to be a part of. And it’s just like, no after no after no. But the important thing is no is really, really a part of the journey. And you kind of have to be delusional to make it work and be like, yeah, no, well, it’s fine, yeah, we’ll just move on to the next thing. Like, being Dululo is the salulu.

[00:05:31] Calan Breckon: I 100% agree. Like, to be an entrepreneur, you really do have to be delusional. And, like, it’s that, it’s that delusional belief of, like, well, I have to make it, I’m going to make it. And that’s just the way it’s going to be. And that’s how most big entrepreneurs had to think. Because if you think about it reasonably and rationally, it is not good odds out there. Most people do fail, and you have to, like, really believe in yourself and really believe in your capabilities and the work that you do. Uh, I I’m grateful that I got into entrepreneurship at an older age because I had done a lot of the work of, like, who I was as a person that I don’t think if I had done that work, I would have been as strong as an entrepreneur as I am today.

Um, but, but making sure that you learn some of those lessons before I got in really helped me on my journey. I want to ask, did you prepare yourself, like financially or any other things before you actually made the jump? Cause that’s important. But some people are just like, ah, I quit my job for sure.

[00:06:34] Ryder Damen: Um, yeah, I am also an older entrepreneur. And it’s like, it’s tough because you get to a point in your life where you, you work your way up through your career and, like, you’re scale of living starts to scale with your income and all of that. So you get used to a certain amount of things. And it gets tough because I think in my early twenties I could make life work on no money, and now it’s just so expensive just to be alive. But yes, I did prepare, so I knew that I wanted to make this jump. So I had spent maybe the last three or four years kind of saving for a Runway. And honestly, it was like Runway or house for me, because in Canada we have a housing crisis, so you have to save up a considerable amount to be able to afford, unfortunately. So I was kind of in between, like, okay, do I, do I buy a house? Do I put a down payment down on a house and kind of, I don’t know, keep my full time job and do this for a considerable amount of time and then delay the entrepreneurial thing, or do I take the jump, use the money as an entrepreneurial Runway and do that. And I, fortunately, after, like, a little bit of therapy, to be honest, I decided to do the entrepreneurial thing and kind of take the jump because ultimately it’s like, what I want my life to be towards. Like, I want to take the risk. I want to, I want to do the cool things. And I’m still fortunate enough that I don’t have any major, um, financial responsibilities. It’s like, no kids or anything like that.

[00:08:16] Calan Breckon: So, um, yeah, yeah, that’s definitely, that’s definitely a factor. I, I believe the same. I was, like, thinking of, like, okay, do I go in this way or do I do what I really want to do? And my heart is, you know, desiring to do. And the thought process is also like, well, when I’m successful as an entrepreneur, because you never say if. It’s always when. Then, like, getting a house is going to be that much easier because I will have created this amazing company and, like, I will be in kinderg, like that, that version of being people, I’d have the money to buy a house. So then it’s like, okay, well, buying the house isn’t going to lead to my entrepreneurship in the same way that entrepreneurship would lead to the house.

[00:08:57] Ryder Damen: Yes. No, absolutely. And I like what you said about the not if, but when. There was a podcast I was listening to, and I can’t remember the name of it a couple months ago, but it said, you should always add yet into a sentence, like, I haven’t raised my seed round yet.

[00:09:14] Calan Breckon: Yes.

[00:09:15] Ryder Damen: Changes your frame of mind. It’s excellent.

[00:09:18] Calan Breckon: Yes. Because we are currently raising our pre seed round. We haven’t raised much yet, but it is on its way. And lots of good things are coming.

[00:09:28] Ryder Damen: Exactly.

[00:09:29] Calan Breckon: We touched on your technical. So your technical background. There’s different types of entrepreneurs out there. There’s, you know, but technical is one of those ones that, like, you need to have on your team or you need to be, especially if you’re going to start, like, from the bottom, absolute from the beginner and create something. So as a technical co founder, what’s important for you when working with other founders and what do they need to know about the technical side of things?

[00:09:57] Ryder Damen: Yeah, this one’s a bit of a tough one. Um, so it kind of, it kind of depends. Like, for me, um, Cashe only has two co founders, myself and Devin. Uh, I’m the technical co founder. Devin is the business co founder, essentially, that side of things. So even though she’s not technical, Devin’s able to suggest like a ton of ideas and different perspectives that I may not have had. So what I like to do is like, sometimes sit down and kind of walk Devin through at a high level, like how the code is working, like what it’s doing here, because she’s able to suggest, even though she’s not technical and has, I don’t think, any idea what the code is doing.

Like, some new perspectives. Like the other day, she was like, well, why can’t we search the Internet for this particular product? And I was like, oh, I didn’t even think that was a possibility. And then we did some googling. We realized that Bing has a search API and we can gather some data through that. And that was something that kind of slipped over my mind because I’ve been entrenched in years of doing it a certain way. And I remember when I first joined tech, from my non technical background, I didn’t study as a software engineer. I used to use that as kind of like my edge to be able to get in and be like, well, I don’t come from tech. I look at things traditionally, but since I’ve been in the industry for kind of some time, I’ve lost that edge. So I think it’s important. I don’t think you can exist in a silo of just your technical stuff and then your business co founder, because you are both, at least for a software, you’re both building a product, and you need to involve both business and technical in order to be the product. You both need to be talking to users. I can go away and I can build a feature, but it might not be a feature that I want.

I don’t know if there’s an easy way to answer this question. Is all of it making sense?

[00:12:01] Calan Breckon: Yes. Yeah, it’s all making sense. I want to dive a little bit deeper. And maybe what you think as, because I’m not technical. Like I’d say I’m technical educated, but I’m not technical. I’m well versed in a lot of the technical, but I couldn’t code or do those things myself as like the business entrepreneur side. What do you think business entrepreneurs or the other side of the co founders coin need to know about the technical? Maybe things like how fast things can be done or specifics that it’s like that’s not possible, kind of things that you’ve experienced in that realm.

[00:12:41] Ryder Damen: Interesting. Okay.

One thing I tell Devin, my co founder, all the time, is that anything is possible.

Technically. It just depends on how badly you want it. Like, yes, this feature may be possible, but it’s going to take us a year to build it because, like, it’s brand new technology. And often things that are seen as quite simple, like going out and searching the Internet for something, is actually quite difficult or quite expensive. Thing is, like, anything is possible through technology. We can do really lots and lots and lots of things, and the product can do, like, quite a few more things. It’s more, do we want to do it? Do we want to spend the time and do we need to prioritize it? So I think communicating those things with your non technical co founder is, like, Paramount, because they don’t understand the engineering effort, or they may not understand the engineering effort that’s required to build what, in their mind might be a simple feature for the product, but it actually is difficult. And then on the other side of things, they’re there to check you too. In the case that Devin did with me with the search thing where I was like, no, it’s, it’s really, really difficult. We can’t do it. And after a bit of googling, I was like, oh, we can build this in, like, I don’t know, four or five days.

[00:13:54] Calan Breckon: Okay, so it’s, it’s, it sounds like it’s. Communication is the key.

[00:13:58] Ryder Damen: It is, yeah.

Everything is communication.

[00:14:02] Calan Breckon: Right?

[00:14:02] Ryder Damen: Like, everything comes down to, like, good communication.

[00:14:05] Calan Breckon: Yeah.

Which is why co founders. Yeah, which is why co founders is like a marriage. Like, you really have to know that you’re in it with this person, and you need to, like, you’ll learn, you’ll learn their strengths and weaknesses and all that, but it really is like getting into business once with somebody. He’s almost more committal than a marriage.

[00:14:26] Ryder Damen: Yes. And that’s kind of how I approached it, because Devin and I met through Antler, which is a global vc, but they run incubator programs to introduce co founders to each other. And when I was selecting a co founder, I kind of didn’t even talk about, like, what our business interests were or anything. We just kind of saw if we vibed on, like, a level, and someone asked me this, they’re like, someone told me this in my cohort. They were like, it needs to be someone you kind of want to travel the world with, because, like, if you can do that and you can tolerate each other in, like, the hostile environment and all of that, then, like, you can tolerate each other at your worst, like, when things are going horribly, because they will, they will go horribly and they will go horribly very quickly and very often. So having that and having a partner who you can exist and work with at a base level and have good communication with, like you said, it’s like a marriage. It’s very important.

[00:15:23] Calan Breckon: Yeah. Having that base level understanding of like, okay, communication is number one. It’s key. Keeping that line open, checking in with each other, seeing what’s reasonable and what’s possible, and not like, making demands and being pushy. I hear these are horror stories. We’ve all heard these horror stories of like, these big companies that got really big, like Uber and other things where their founders were just crazy people. And I never want to work with anybody like that in my career.

[00:15:55] Ryder Damen: Yeah, it’s.

[00:15:59] Calan Breckon: Yeah, yeah, no, it’s important.

[00:16:01] Ryder Damen: That speaks for itself.

[00:16:02] Calan Breckon: Yeah, yeah. So you mentioned Antlerez. You’ve done fundraising and antlers part of that.

What’s your best advice for other founders looking to raise capital and how maybe tell a little bit of the story of how you did it, for sure.

[00:16:19] Ryder Damen: So Antler is a little bit different. It’s not the traditional route of raising capital where you go and you pitch. Antler is a day zero investor. So Devin and I were actually in different cohorts, but we were introduced. I was on the cohort that followed hers, but she was brought back to pitch and that’s how we meth.

But antler works. It’s kind of, it’s a ten week incubator. You go in either with an idea, without an idea. Some people had preformed teams and all of that. And over the ten weeks you work rapidly and you meet other people and you test ideas and then you invalidate them. Like Monday you think of a new idea, by Tuesday it’s dead in the water, and Wednesday you have a new one and by Friday it’s dead again. It’s, it’s, it’s exhausting, but it’s super, super productive. And at the end of the ten weeks, you have the opportunity to pitch the investment committee, which is antlers fund, and theyll decide if theyre going to invest pre seed funding in you or not. So fortunately, Devin and I received the investment. Were super grateful to be an antler portfolio company. Its really cool.

But we didnt go out and pitch VC’s in the way that you might do it when you’re raising capital. It’s something that we will need to be doing quite soon, actually, when we feel comfortable that we’re ready to raise our next round.

So I don’t know if I’m the best person to provide advice on how to raise capital, especially because I’m the technical co founder, and yes, I’m a part of that process, but it is the CEO who is selling the company, who’s raising and all that. However, I can pass on some advice that I’ve gotten from casual interactions, meeting with other founders who are much, much, much more successful than me. And that is, don’t raise until you have to. They’ve all told me the same thing, and they’re like, a lot of people raise because they think it’s like a badge of honor or they think it’s the only capital available. It’s only venture capital available, but there’s often other ways to do things. So of course there’s bootstrapping. There’s non dilutive capital that a lot of people in Canada don’t take advantage of. And honestly, we need to give it a second pass as well to take a look at it, because we’ve only given it a glance, but all of them have told me the same thing. Don’t raise until you have to. If you need the money, sure, raise it. If it can help you move faster, raise, but don’t raise another round because it’s going to get you a nice crunch.

[00:18:52] Calan Breckon: Base article, no? Yeah. That should never be the base foundation. My belief is, I mean, currently in the current ecosystem, like, raising is nowhere near as easy. It was as easy as it was a couple of years ago, just because things are kind of looking like they’re going in a downward direction, which is natural. It’s part of the ecosystem we have in a capitalistic system. But in that, it means that if you’re going to survive as a company, you need to get really scrappy and bootstrappy. And we’ve been bootstrappy since beginning. And so the more you can be and have the bootstrap mentality of doing more with less, it’s going to work out for you in the long run, because maybe you just need that little bit of seed money and you don’t need to do a full series a round that, that can really take you quite far. And then when you do get to eventually get to that a round, you’re going to be valued at such a higher valuation that it’s going to make it like a better experience. And you’re not going to have to dilute yourself as much as if you were just like, well, I want to raise now because we want more money now. It’s like, just because you’re going speedy doesn’t mean you’re actually providing a good service or doing something well. It’s building that foundational piece and really building out such a strong foundation and structure to your company. I think of it like a pyramid. Like the pyramids have been around for so long because they built solid foundations and upwards. And so that’s how I think about building companies as well. And raising funds isn’t necessarily the best way to do that, especially if you’re working with VC’s and I and VC’s jobs are to capitalize for their clients. And so of course they’re going to push you to go faster. And that pressure sometimes can be good, but sometimes could also be negative.

[00:20:37] Ryder Damen: Yes. Yeah. It might not be in the best value of or the best interest of the businesses, or the best interest is you as the founder as well, right?

[00:20:46] Calan Breckon: Yeah, exactly. So you’ve mentioned Cashe kind of in the conversation, so let’s dive in deeper with that. So tell us about Cashe and what you’re working on to achieve with it, for sure.

[00:20:56] Ryder Damen: So Cashe is a consumer app. We’re b, two c, which is, I guess, maybe a little bit unusual. You see a lot of b, two b businesses, but I believe you’re also b, two c. So, yeah, high five.

[00:21:08] Calan Breckon: We’re b, two b and b, two c and b, two b to B C, half.

[00:21:12] Ryder Damen: High five. Yeah, we’re good.

So Cashe is a consumer app. Our goal is to make reselling clothes as easy as it is to buy them. So the way that we do that is we’re a web app right now. We’re hoping to become a mobile app very soon. But you sign up, you sign up with your email, and we’re able to go through your email and extract any purchase receipts that you may have made. So you go to Aritzia, you go to Zara, you go to H and M, Uniqlo, whatever, you buy something, you get a purchase receipt in your email. From that, we’re able to pull out all the products in that email and automatically import them into your closet with all the original product details, photos, sizing, description, everything. Like make it nice and very pretty. You’ve got then a virtual closet where you’re able to take advantage of the styling options. You’re able to put clothes together and different outfits, make packing lists for a trip, share with friends, seek inspiration from others, have followers, get people to follow you, is something we’re introducing pretty soon, but then most importantly, when it’s time for you to part with an item. You click one button and you’re able to post it to any of the existing marketplaces.

When we were talking to users, we found that there’s virtual closet apps and there are resale apps and there’s not really that many links between them. And furthermore, there’s tons and tons and tons of friction. So a lot of people don’t want to use the virtual closet apps because you have to take a photo of every item in your closet and then import it and then manually. Like the name of this is this and the name of this is this.

Our bet is that if we automate all of these things and we reduce this friction, we can enable more people to sell. Because most people want to sell. They like the extra money. They want to be able to trade in the things that are just sitting there and go on a trip to Europe. But it’s effort. I mean, no one likes to do any extra work, right. No one has time for it. So that’s kind of what Cashe is overall.

[00:23:10] Calan Breckon: Okay, nice. And it also adds to kind of the eco friendly, like, you know, recycle or upcycling of clothing instead of this constant consumer economy. It’s like, how about you consume but on a conscious basis?

[00:23:24] Ryder Damen: Absolutely, yeah. Circular economy. Sustainability is super, super important to us, but we don’t really want to scream sustainability with our brand. We just, we want to be a thing that fits in and makes a better contribution. And that was important to me when selecting a business, when, when deciding what I was going to work on was something big, data, something machine learning. AI was really important to me, but also something that was going to do an impact, like make it hopefully a genuine impact on the world.

[00:23:56] Calan Breckon: Yeah. Make a difference.

[00:23:58] Ryder Damen: Yeah. As opposed to, I don’t know, some b two b SaaS.

[00:24:01] Calan Breckon: Yeah, I don’t know. Right. So I’m really interested in this idea, like how Antler worked and how you became an entrepreneur. It was less of, I know a person, we have an idea, we want to work together and build this thing. It was like, I want to be an entrepreneur. Im going to go in this program and then through that program discover what that thing is going to be.

[00:24:22] Ryder Damen: Kind of, yeah, more or less. Antler is kind of open in the sense that you can come in with no idea. I came in with no real idea. I had a couple that I was playing around with, but theyre more just projects and less venture backed businesses or venture backable businesses.

But some people came in with entirely established companies and went through the program and kind of made some connections there. I think one of the most valuable things about Antler, beyond obviously, the investment and the advice that we got from the team and all of that was like the Kickstarter, the bootstrapping of my entrepreneurial network. It’s how we met. It’s how I met so many other people here because I was involved in entrepreneurship in university, but university was like ten years ago, so I’ve since kind of fallen out. And no one who I knew besides a couple of my old buddies who are still running their company, love them.

No one who I knew are still involved in the entrepreneurial world. So antler was able to very, very rapidly kind of kickstart that network and introduce me to what I now know is actually a small community because the Toronto entrepreneurship community is quite small, but was able to introduce me to a bunch, a bunch of different people and kind of get that network started. And that was. That was really helpful.

[00:25:48] Calan Breckon: Yeah, that’s definitely what accelerator programs are really great for. I know that I found a lot of entrepreneur support through the CGLCC. The Canadian LGBTQ+ Chamber of Commerce has been really great for queer entrepreneurship, and then also StartOut down in the states has been fantastic. They are, in the US, the first, and I think only queer specific LGBTQ accelerator program. And so through them and their connections, we also found our mentor, who’s been amazing to work with and he’s really helped us on our business and our journey.

And so there’s a couple of really great programs specific to, like, the LGBT community out there that work really well. But then the traditional ecosystem also is fantastic to build and find, but it can be hard finding and hunting for the right one that’s going to be right for you.

How did you find Antler? How did you actually come to that decision that this is the one that I should go with?

[00:26:52] Ryder Damen: Honestly, it was timing.

I don’t think I really put much thought into it beyond timing and location. It was.

Antler had reached out to me previously a couple of years ago, so they were kind of on my mind and I knew I was ready to make the jump. And I kind of wanted to settle in Toronto temporarily because I have a network of friends here and people I could rely on, and I knew that if I were going to make it through a ten week incubator program, I was going to need support from some friends. So that was honestly kind of the main drivers of my decision, but, yeah, nice. That was about it.

[00:27:35] Calan Breckon: Awesome. Well, this has been an enlightening conversation about how there’s the ups and the downs of entrepreneurship and learning about what you’re working on and what you’re building with Cashe. I want to thank you so much for being on the show today, Ryder.

[00:27:49] Ryder Damen: Thank you. Yeah, it’s been a pleasure.

[00:27:52] Calan Breckon: All right, you have a fantastic day.

[00:27:54] Ryder Damen: You as well. I’ll talk to you later.

[00:27:56] Calan Breckon: Thanks again for tuning in today. Don’t forget to hit that subscribe button. And if you really enjoyed today’s episode, I would love a star rating from you. The business Gay podcast is written, produced, and edited by me, Calan Breckon. That’s it for today. Peace, love, rainbows.