How to Find your Co-Founders | Lindsey Goodchild, Founder of Nudge

Lindsey (Guest) 0:00 I did what, I thought, was the right approach. I went to Kijiji and I posted some ads to see if somebody would build this app and work with me. And in doing I had a bunch of responses and I thought I found somebody that would do it, and I ended up paying them half up front. And I never heard from them again, ever. That was a really low point. Intro 0:24 Welcome to the product-market fit show brought to you by Mistral, a seed stage firm based in Canada. I'm Pablo, I'm a founder turned VC. My goal is to help early-stage founders like you find product-market fit. Pablo (Host) 0:35 Today we have Lindsey, the founder of Nudge. Nudge is a digital communications platform for improving workforce performance. They're based in Toronto. They have about 70 employees and have raised over $15 million. Lindsey, it's a pleasure to have you here today. Lindsey (Guest) 0:53 Thanks for having me. Pablo (Host) 0:54 The topic of today's episode is how to find your co-founders. And that's a really interesting topic because I meet so many founders, and it's just such a big issue for early-stage founders, idea stage founders that maybe they're technical, and they need somewhat more of a business mindset, or they're more business, and they need somebody technical. And there's no clear playbook. It's not like, well, you do this, this and this, and you end up with a co-founder. It's a really tricky one. And yet, you have to find a way to solve it. I'm really, really interested in hearing your story of how you did it because I do think people by kind of hearing a story and the examples will really be able to get the sort of things they might be able to do to also find a great couple of Why to join accelerators Pablo (Host) 1:44 co-founders. Maybe just to start it off, Lindsey, if we could start really at the beginning. Was it always the plan? I'm going to find a co-founder. Is that how and why you're joining, DMZ, MaRS, et cetera? Lindsey (Guest) 1:54 Yes, at the time I joined the DMZ and MaRS, I really wanted to become a part of the community and better learn about entrepreneurship. And as I did, and really started to understand the potential of what it was I was doing, I recognized that I couldn't do it alone, in order to build a meaningful business. And also just to have some of the core skill sets that a business like this would require, I wasn't going to be able to do it all myself. I didn't have the money to hire a large team, or even a small team. I couldn't hire anybody. I had no money. As I started to get more involved in the community, I recognized more of the opportunity and the more I understood the opportunity, the more I realized having the right people at the table with me to build this thing from the ground up was going to be essential. Pablo (Host) 2:38 Okay. And to be clear, were you still part-time? I'm curious, when did you make that flip over to “okay, I'm all in on this?” Lindsey (Guest) 2:44 I was working on this in the evenings and the weekends for probably the first year. I was also at a really exciting time in my consulting career. I just won a very big project that I was a big lead on, and I brought a bunch of industry experts to the table. So, it was a difficult decision for me because I had just gone to school for six years to get this kind of job, and then I was finally making some serious tracks and then this other opportunity came. But at the end of the day, it was just, the problem just continued to surface in all of my work. And I knew I needed to take a stab at solving it. Steps to take when looking for a co-founder Pablo (Host) 3:26 Got it. So, you're getting to DMZ you get into MaRS, and what exactly are you doing to meet people and to potentially find someone that could be a co-founder? Lindsey (Guest) 3:41 Well, back then, I mean, a little different than the world we live in right now, but there were a lot of seminars on building your business plan, building up your business, different, marketing tactics, sales tactics. I was just so hungry to learn all of it. I was showing up to all of these different sessions. Tried sticking around afterwards and then networking, and trying to meet other people, meeting other entrepreneurs who are at varying stages in getting their stories and understanding how it all went for them. Through that, I ended up meeting a mentor who really understood what I was trying to do and said, "All right, look, let me help you." He'd built a number of businesses and helped me map out a plan to getting this thing built and coming to fruition. He helped me, get networked with a number of different development agencies in Toronto. I went and did that tour and kind of understand the scope of the costs. I was having conversations around, maybe I raise a bit of angel money to help out with this first round of building. I also, I did a lot of startup weekends. That was a really cool way to go and be with a whole bunch of different people, but, build a business, essentially, over the course of the weekend. I loved that you get all different backgrounds and all different skill sets coming together, and it's a good chance to try people on for size to see how you work together. I did quite a few of those and that taught me a lot. Not only about, finding the right partners and the skill sets, but also about building a business and a lot of the early validation and so on. Pablo (Host) 5:11 And I know you met, and we'll get to how you actually met your first co-founder through the agency roadshow and working with agencies. With these events, you would network afterwards. Did you try, if you met someone interesting, take them out for coffee and try and just like get deeper or start working with them on the side? What sort of things did you try through it all? Lindsey (Guest) 5:32 Absolutely. I met quite a few people that I met for coffee afterwards. I did find, I ended up meeting a lot more founders with ideas than technical co-founders. That also might've just been because that was more similar to my own scenario, but I think spending those times grabbing a coffee, getting to understand people, they connect you with somebody else who would connect you with somebody else. There is a lot of power to that, and it does take time, and it does take effort to nurture those relationships. But for me, I was really keen, as I mentioned, to learn from people that were at various stages. Through that, I ended up meeting a mentor and then a different mentor, and that mentor ended up introducing me to another one of my co-founders. I have two co-founders, found them two different ways. It was a lot of heavy lifting, but it's so important, I think, to go through that process of meeting a lot of people and understanding how different people think about building businesses. Because picking a co-founder or finding the right co-founder is really, it's one of the most... it is the most important decision you're making in building a business. Pablo (Host) 6:47 Back Using agencies before having a co-founder Pablo (Host) 6:48 to it. So, you start, one of the mentors starts introducing you to agencies. You don't have much of a budget, but you start talking to agencies to at least understand what it would take. So, walk me through that, what happens after that? Lindsey (Guest) 7:04 Meeting a lot of these different agencies was a really important part of the process because I was able to start to understand the true scope and breadth of what it is I was trying to build. It also gave me a much better understanding and appreciation for how much time, money, and effort it was going to be to get this thing off the ground. But it was a really important part of the process, I think, to just really flush out a bunch of elements of the ideas. And it did help me understand, for me to go into this, I was going to have to find a way to bring...sell this thing ahead of time and get some customers to pay up front for it, or bring in some capital or find an early investor. I did a bit of both. I was able to really find alignment with one of the agencies around what I was trying to build, the opportunity. And they became one of my first investors. And at the same time, I was out there still trying to pre-sell the product. Those two things came together to give us the confidence to move forward. The Working Group ended up becoming the first investor and helped me build out the MVP of the product. Pablo (Host) 8:11 And so, you start working with them and in parallel, you still don't know where co-founder's going to come from. So, you're still going to all these networking events and still using different strategies to try to meet people and find a potential co-founder? Lindsey (Guest) 8:24 Absolutely. So, I'm moving forward with them. I decided to move forward with the agency because I hadn't yet found a technical co-founder, and I was under a bit of a time pressure because I had taken some upfront payment from some customers. So, I knew I just needed to keep pushing forward. And I thought, I'll continue to go down this path. And I was applying to accelerators, I was applying to all kinds of different support networks to hopefully find a co-founder. I remember doing co-founder dating, one of these rapid fire things where you meet like 20 people, and you talk for five minutes and see if there's any magic. But Serendipity is key Lindsey (Guest) 9:06 as that was happening, I was already engaged with TWG and starting to build the project. And I recall in some of those meetings, there was one of the members of the team that was on the build team, who was Dessy, was just really engaging in those conversations from me, asking really thought-provoking questions, helping me understand the landscape in which I was getting into building this technology and her and I just had a really good rapport in these meetings. And afterwards, I remember after one meeting, I was like, "Hey, do you want to grab a beer after and just talk a little bit about that? I have some more questions. I'd love to pick your brain on some stuff." And so that started to become this regular frequency. I would go and have the big meeting with a bunch of the folks involved in the project from TWG and Dessy would always be on that team, and then her and I afterwards would always go and grab a beer and kind of talk about things. And in those sessions I realized, I loved the way that she thought about building scalable technology to make a difference in the world. And I think she saw the opportunity with Nudge to bring a lot of her own entrepreneurial dreams to life because she's always wanted to be an entrepreneur. She had a game plan, I fell into it by accident, but it was really interesting to meet somebody who had thought about it from a totally different angle. And eventually, I had to ask her if she was interested in being my business partner, which was kind of weird because we were friends at this point and I realized if she says no, I wonder if this is going to make things really weird for us. But she had told TWG when she started working there that she was always interested in going off and building her own thing. So, she was at Eloqua and was building the big thing for a while, and then she went to TWG, so she could build a lot of smaller things and just really get that broad experience. And so, it was, I did have my moment of serendipity in this whole thing because, her and I got together and really found some great alignment and had totally complimentary skill sets. Pablo (Host) 11:04 And one of the questions I have is, obviously at some point you decided to ask Dessy to become a co-founder or if she wanted to join How to know you've found your co-founder Pablo (Host) 11:13 you at Nudge. But how early on did you think to yourself, I want Dessy on my team? At some point you're just kind of meeting her, you're going for beers. When did you cross that line and why? Lindsey (Guest) 11:24 Probably after our second meeting of beer and poutines. We had already had a number of meetings together and had been working together for a while through the working group relationship, but I felt like we really clicked as friends, as colleagues, and I had such an admiration for her brain. She's absolutely brilliant. The way she thinks is just remarkable. And so, between that and the overall vision alignment around what we wanted to do in the world, I felt coming out of the second or third meeting, this, this is the one for me. I hope she feels the same way. It feels a lot like I'm talking about dating, but it's kind of the same. You really are committing a good part of your life to spend with somebody to solve some of the hardest stuff that you could possibly imagine. So, do want to have that chemistry. And I feel like the nerves and asking her if she wanted to be my partner were normal, and obviously, it worked out really well. We've been together for a number of years now as business partners to be clear, we're both married to other people. Pablo (Host) 12:41 I appreciate that. So, the other question I have around this co-founder you've been looking for a long time. Did you have a very clear idea - you needed to be someone technical - but did you have a clear idea of anything else that you were looking for in a co-founder? Lindsey (Guest) 12:56 I did when I met my third co-founder, that kind of hit me like a bolt of lightning, in terms of, I realized in that meeting, what my co-founding team was missing, which was a tried and true entrepreneur that's done this many times before and is always thinking bigger and how to push the envelope and how to scale and how to get all the right pieces and partnerships in a shorter amount of time happening. And, Dessy and I had been working together for maybe a year and... maybe less than a year. We'd raised a little bit of money, and we had our first MVP together. And my mentor had introduced me to Jordan, who had just come back from six months in Asia because he was taking a bit of a sabbatical after selling his last company. And I sat down with him, and he just started grilling me with questions on the business and have I thought of this and have I thought of that? Or what about this? And what about that? And I loved the way he was testing my thinking and pushing my thinking and adding, to our thinking in just in a matter of an hour. The first coffee meeting was just... I still remember so, so clearly, and coming out of that, I was just like, man, it would be so great to have that perspective in this business every day. So, we started working. We asked him if you would be interested in helping us out with a couple of projects. So, we kind of tried each other on for size and said, "Hey, come work with us almost as a consultant on a couple of things." And he did. And then the three of us realized, here I am, coming to the table with a good understanding of the problem, having really understood it, but not a lot of background in business and technology. I come across Dessy, who is an absolute technical wiz, and then Jordan, who is an entrepreneur who just loves to make things big and bold and go fast. And so, I think the three of us really recognized early on that we could do something special together because we were all bringing something different to the table. Pablo (Host) 14:56 Back to Dessy, once you asked her to join, and she's interested, How to split founder equity Pablo (Host) 15:02 another big question that comes up here is... I would say number one, probably the equity split, like that's probably the next big thing. Do you say, "Let's just do it down the middle, or you were there for six months, you came up with the idea you should have more," how did that kind of negotiation go, and how would you recommend to founders that they should think about that? Lindsey (Guest) 15:21 Yeah. I read a lot of logs about that when I was trying to sort that out. I think at the end of the day, the equity split doesn't really matter as much as having the right people at the table. Because it's not really the size of the piece of the pie, it's how big the pie is. With that said, I think equity really speaks to how much risk each person is taking. So, for me to quit my job, which I eventually did, and raise a bit of capital and secure some first customers and have an idea and a vision, I put a bunch of the work in. So by the time that Dessy joined and then by the time Jordan joined...by the time Dessy joined, there was a bit of validation that had already gone on and then, her and I were working together, and we got an MVP and a bit of capital in, and then Jordan joined. The equity split kind of reflects the risk taken by each person along the way. Co-Founder vs Technical Hire Pablo (Host) 16:13 One question I have is, [inaudible] the effect of what it felt like before and after Dessy. You were just you, and then all of a sudden, you had another person in there who is a technical co-founder. And I'm asking this from the lens of, there's some founders who would, let's say business founder, or even technical one doesn't matter, but let's think business founder who might say to themselves, "Well, what if I could just get enough traction, raise some money, especially in this environment where raising money is better than it used to be, let's say, and then just hire a technical person." How do you think about that versus really getting a technical co-founder versus in terms of what it feels like to work on the business Lindsey (Guest) 16:51 For me, having co-founders to share the highs and share the lows and share the weight... Building a company is hard. And so, I feel really grateful to be spending this time in this journey with two people I really trust and really want to do this with. It is hard and it is lonely. I feel, personally, for myself, I would have a really hard time doing this on my own. There are amazing single co-founders that do it. It is possible. But, I think it depends on kind of the type of person you are and what you want. But for me, I wanted to share in the highs and the lows with people, and it has made all the difference in how I feel in this journey. Even in the early days, when I was just a lone founder, you're in it alone. Whether you're trying to prepare for a pitch or you're trying to handle some tricky thing, it's really you. You're just kind of bouncing your ideas off yourself, maybe a mentor or two, but it's different when you have somebody who's fully in it the same way as you, thinking about problems in the business or thinking about challenges and is so truly invested in solving them. You have complete alignment on that, that you really do have a true partner in crime. I'm always of the mindset two minds are better than one, and three is even better. That's really worked for us, but I have a lot of respect for single founders that can find their way through, on their own. I don't know how they do it, but I think it's pretty badass. Pablo (Host) 18:26 Awesome. So, that's really helpful. Fast-forward a little bit, it's you, and Dessy raising money, you get some customers, are you still looking for a third co-founder when Jordan gets presented to you? Lindsey (Guest) 18:39 We were not looking for another co-founder, but it was one of those light bulb moments, aha moments where in that first discussion with Jordan, it became so clear to me what we were missing from our leadership team, just tiny team really at that time. Because of his experience in being a repeat entrepreneur and just his out-of-the-box thinking and his tried and true playbooks and just the entire spirit that he brought to that conversation opened my eyes to what else it was that I was missing or just didn't know. It was of one of those things where you could feel how it could be really powerful, very early on, but at the same time we've ever worked together, we've not done anything together other than have this one or two amazing coffees. Having the chance to bring him into the fold under the guise of a consultant and help us chip away at a couple of big things really gave us a chance to see what kind of damage we could do as the three of us. And it became really compelling to see just how much we could get done and how our various skill sets really complimented each other, and we could just get further, faster together. Pablo (Host) 19:53 And did you think about, once you decide, yeah, we want to bring them on full time, it's going to be great, just making him COO, and then you have him on the executive versus making co-founder? How did you think about that? I know it's partially just the title, but it's not also. How did you think of that? Lindsey (Guest) 20:09 It became really obvious that he was a co-founder just in terms of the way we were dealing with pivoting the business and some product-market fit and just the effort in, and just the businesses, partly his business. He was an owner. We were at a point in the journey of the company where we were still really early. He really brought a dynamic to the team and a dynamic to what we were trying to do. That really is part of our founding story. So, it was the most natural thing for him to be co-founder, and he is our COO now, he's kind of fit all of the places in the business that he's needed to be because he's very, very skilled across many different things. Ultimately, I think co-founders means sharing the business. If this business is your baby, there's three parents. Pablo (Host) 21:06 Got it. That's really helpful. Now you got the three co-founders, that's all solved, things are going well. Maybe one question to end it all on is, at this point you've raised a series B you're more in scale mode, but when did you - this is the product-market fit show, so What PMF Feels Like Pablo (Host) 21:21 I just have to ask - when did you feel like you had product-market fit, and what are some of the indications? Lindsey (Guest) 21:30 It is such a big topic, and it always evolves, right? Even when you have it, the market is still moving, so you're constantly evolving. For us, the whole reason I started this business was because of a problem I found when I was consulting and had conceived of the solution and is this going to work? So, we finally launched it, and it did, and it worked really well. And when we started to see the traction, not only from the customer side, but from the user side, just wild, viral uptake on the user side, really great adoption, really great engagement, we really knew we were onto something. But we had a couple of moments early on where an employee would go to another organization and ask the organization, where's Nudge, and why don't we have that? And that kind of worked its way up the chain and got us some of our customers. And so, some of that word of notes and advocacy was a really big sign to us that was showing there's a need for this, people are using it. But not only are they using it, they're loving it at an employee level, but also at the buyer level. Even just earlier this week, one of our customers posted this amazing thing on LinkedIn about the impact that Nudge just had on their frontline team. And I think when people are so happy and proud to use your software, and they're willing to share that with the world, you know you're really on the right track. Recap Pablo (Host) 22:57 Perfect. All right, Lindsey, we'll end it there. Just to recap, you started off with an idea, with a problem really that you wanted to solve, and you were alone with, as you said, no or not much business experience, no technical experience, and you figured out a way to find a great technical co-founder, an amazing experience founder as a third co-founder and built Nudge into what it is today. As we said, 70 employees, many, many customers and scaling really fast. And so appreciate you sharing that story with us today. I'm sure founders listening will learn a lot from it. Thanks a lot. Lindsey (Guest) 23:34 Yeah, my pleasure and good luck. Don't compromise. Pablo (Host) 23:38 Thank you so much for listening all the way through. It's been a pleasure having you here. Make sure to subscribe so, you don't miss the next episode.