Executive Director – Schulich School of Business
Chris Carder

"There's ethics and values, but there is no box."

- Chris Carder

Chris outlines what he looks for in a start-up

Talk Takeaways

Chris Carder distills creative fearlessness and shares personal stories on the hustles he took to grow his startup. Understand his process as an investor and his unique approach in overcoming entrepreneurial challenges.

About

Chris Carder is a Serial Entrepreneur with more than 20 years experience in the Digital/Technology Sector and a sought-after Startup Advisor, Investor and Advisory Board Member.

Chris serves as Executive Director of the Office of Innovation and Entrepreneurship with the Schulich School of Business and also Special Advisor on Entrepreneurship and Innovation to the Office of the President at York University.

Chris is the past President & Co-Founder of ThinData (Canada’s largest email marketing services provider) – acquired by TC Media (Transcontinental) in 2018.

His volunteer work in the non-profit sector includes serving as Chairman of theInternational White Ribbon Campaign and he has been recognized as the Canadian New Media Awards Volunteer (and Employer) of the Year.

The full #OPNAskAnAngel talk

Jeffery:
Well, Chris, I’m super excited and so glad that we were able to connect and chat today, and we jump right into things. So welcome to Ask an Angel, brought to you by OPN. And we’re excited to talk with Chris Carder because, Chris, I’ve been an avid fan and follower and working and collaborating with you for — it feels like at least 20 years now from my lob laws days and you’ve you’ve done a significant amount of change, growth in the startup world, and you continue to plow forward. And I was always excited because to talk with you because most of the people that I’ve talked to in the start up world they’re probably known that maybe five years or whatnot. But you come in and from a total different angle. And I’ve actually seen you in action in your startups and in your business and now going through to what you have and participating with you on some of your events. So it’s exciting for me to get to dive into a few of the things that you have done. But the way we like to start is perhaps you can give us a bit of a background on yourself what you’ve done in the past, some of the startups from the data all the way up to where you are today. And the things that you’re working on now and then one thing about you that nobody would know,

Chris:
Nobody would know… Interesting. Okay, so first off, the very first startup goes all the way back to 1995. And that’s when I created an online sports magazine. I was a journalist, journalism student and working journalist. Um, and, uh, I, you know, found very quickly that the newspaper business in the magazine business was gonna be a tough one to find employment in on an active basis. That trend was true and beginning even back then. So my brain wave was well, if I create my own publication, then I own it, and I can employ myself. And that was really the beginning of being an entrepreneur and having a startup. I created that with a very close friend of mine, and we built it. And it was this online sports magazine. We sold it within the first — I say 2.5 years we sold it. It became the website for the fan 590 sports radio station. From there we kept the team. We kept some of the technical assets we had created for that, and we created a Web development company. And from there we built that up until we suddenly saw a need where our clients all started showing up, asking if we could recommend an email marketing platform. And we thought, This sounds like recurring revenue. This sounds like something that kind of prints money while we sleep versus project chasing in the web business. Andwe set out and with a couple of turns of good fortune, built what became the largest email marketing platform in Canada, and we grew that to about 60 plus people at the time of selling it, and it was acquired by a big public communications company. And then we stayed around for a couple years and worked on transitioning it and throwing it up to 114 people and then after that, left to continue and look for other journeys and other adventures.

Jeffery:
Amazing. And then you kind of shifted into another start up, and then you moved your way into Schulich, um, what do you what do you do now? Actually, how’s that looking?

Chris:
Yeah, we’ll jump in that a second. I just realized I forgot to tell you the one fun fact that nobody knows about me. So I’m going to have to tell a lot of stories. I’m very open with my life. So I’m gonna have to go with one Very few people know about me, which is that I’ve actually, um, been, uh, at one point in my life, was flown to Fox Sports in Los Angeles by Fox for the opportunity to pitch a television show on professional wrestling. And I’ll tell you, man, like I’ve been pitched a lot of things in my life. I’ve sat at a table and asked a company for, you know, $20 million with a straight face and and a sincere heart. But I’ve never been so nervous as I was pulling up to those gates at the Fox Studios and going to pitch a television show. Now, Schulich on the other hand, So my time now I’m at Schulich, where I originally started out a few years back as an entrepreneur in residence and then started to build out the Schulich startup program as it’s become today. And that itself is an interesting story. Because I was, I decided this was my next great passion, working with young people, helping them on their companies and on their career journeys in the innovation and tech sector. And, um, I there was no startup program at the school, and so I thought this would be a cool job if I were to have it. So I worked for eight months for free building the startup program, and my plan was that eventually the dean and the senior leaders at the school would take note of what I was doing and and then they noticed. And then they came down. You know, I was sitting in the cafe, building it with the students and some of the alumni, and they came down and said, Hey, we’d love to talk to you about taking this to another level, another level, And then that eventually led to me, becoming what is now the uh, the executive director of the Office of Innovation and Entrepreneurship at the school. And we have many, many programs, both in the start up space and for innovators who are looking to work with founders and venture capitalists throughout the ecosystem.

Jeffery:
Brilliant. I love it. Um, and, uh, we kind of fit in the same realm on the things that we do there. And it’s fascinating that, um where you guys where you have made that pivot and changed into the Schulich. One thing I love, the fact is that you did it for free, and then you found a way to obviously built in, show some value and that converted the school into believing into your direction, which is awesome. And then it became obviously more than a passion. It became a value add for both sides. And now you’re helping a lot of startups globally, um, become where they want to go. And I think that’s a phenomenal, uh, growth chart. And one of the things that I can say that I learned from you over the years was your stories. Um, it was the directions and myself. I love telling stories, but they’re usually not so much geared around me. But of course, everybody else. So I’ve shared your a couple of your stories many times. Um, and what I kind of wanted to focus a little bit on our talk was more about the hustle because most of the interviews we do they’re really domain focused on somebody that maybe is supporting in finance legal, like all these different aspects that really make up a great investor. And one thing that we, uh, talked about sales. But we’ve never really talked about what sales really mean and what the hustle means to grow a startup. And if there’s anything that I learned from you over the years was really about being strategic on how you execute on that hustle. And I’m wondering if that’s somewhere where we can kind of touch base on start from some of the things that you did back in the thin data days on how you opened up doors and how you got people interested in your business, just like you said on the print side in the magazine side, or being flown to Fox and ended up or you’re pitching $20 million. These just weren’t fluke opportunities that you really strategically found ways to make sure that you were able to execute on them, and I kind of want to dive into that? Because that’s where I find that the excitement is where entrepreneurs can really learn something about not only what it takes to be an entrepreneur, but what you need to do to be an entrepreneur, to be successful and close deals. Um, so maybe we can start by. I remember this story you told me once and you said that, uh, you had heard that there was going to be a client going to be having dinner or a drink at this restaurant, and you structured it. So you were sitting at the bar with this person, and you were able to eventually build rapport and have this that happened to have a conversation with them and then that turned into a lot of great things in the future and becoming a client. So I’m not that I want to steal your story from that. But I would remember it to a t because it would to me was strategic. And it was, how do I get an outcome that’s going to benefit where I’m going? So maybe you can talk a little bit about that and then share some stories that kind of dive into it And what got you interested in taking that approach?

Chris:
yeah, I think that, you know, a quick nod to my my roots again in journalism Is that the one thing that I took away, or maybe two things I took away from journalism school and from working as a journalist is one. If you want to get the story, you’ve got to do things differently than other people and to you got to be fearless. So you’ve got to be willing to walk up to people, find ways to get to people you know, like that would never. The stories that we were taught were stories about journalists who got stories that nobody else did, found ways to get people to open up and meet people that nobody else did. So once I found myself as an entrepreneur, then I started applying a lot of those same principles and the term that I’ve kind of, like, coined for myself. I don’t know if it’s used by other people publicly, but I like to use the expression creative fearlessness. Um and so it’s It’s the kind of the art of being fearless, but not in a reckless kind of rampant, totally spontaneous way, like actually having a a plan as to how to apply strategically and creatively with a lot of ingenuity, fearlessness in the process. And so there’s been times when I have, like, you know, found myself in positions where you know, or put myself in positions where I can just collide with people in just that right moment or other times when, um, something was unfolding and I and I took advantage of the opportunity to give a couple of quick stories like, um, there was one time when we were pitching like a massive client, big bank and, um, they came in for for a pitch. Let’s say it was like, three o’clock in the afternoon at our office and when they came in the office, um, you know, by, uh, by happenstance will say for the moment they sat down in the lobby and they sat down and they met like a client from thin data. Real client, wonderful long term client. Uh, and they sat down and I knew they were there. But I didn’t come to the lobby immediately to pick them up and take into the boardroom I let them hang out with the person. The other client who was in the lobby. So the big bank, they were thinking of being a client. But this person was a client. They had a nice conversation, and the person from the current client roster talked to them all about what it was like to be a client and why they enjoyed working with us and all the great things we had done for them. And, uh then as I came into the lobby, picked up the bank and took them to the boardroom. That client walked out the door and gave me a wink because we had actually orchestrated a live reference check before the pitch started. So the bank walked into the boardroom preset that these guys are cool. The clients are there and love them, right? And they thought the pitch started when I opened my mouth in the boardroom. But the pitch actually started 10, 15 minutes before sitting in the lobby with a client who had agreed to come and sit there and wait to hang out with them and tell them a story. It’s a true story. It was from the heart and obviously the client meant because they showed up in the middle of the business afternoon to sit in the lobby and and be part of the pitch. So that is that as an example? When I told that story, very few people have ever said, Oh, yeah, I’ve done that one before or I’ve heard that one before. That’s a pretty kind of unique way to approach it. In fact, why that client was so who sat in the lobby and helped with the pitch was kind of, like, so excited by the idea and in on it was because when I won over that client, um, I had actually gone to a big industry conference where that client had a booth, right? And so the client, um, was in the middle of an RFP with 20 companies, hadn’t hired us or worked with us before. They had met with us the previous week, and I’d heard that they were going to have a booth at this trade show. So I went down to the trade show. I grabbed myself like, you know, these days would be an iPad, but back then it was a clipboard and a pen and a paper, and I stood in the crowd just far enough away from them that they couldn’t really see or hear what I was doing. But they saw and recognized that it was there, and I started interviewing people in the crowd and taking this whole survey as people were going by. And then eventually, after like half a day, the guy came over from the booth who was in charge of the RFP, and he was like, “Hey, Chris, what are you doing here? What’s going on?”, and I said, Well, I mean, this project is really important to me. Um, you have a very tight timeline. So I figured I’d start gathering some customer intelligence immediately so we can better craft the plan. And then I said, But I’m really busy right now working for you, so we’ll have to talk later. And I just walked away. And then he waited. He saw me there. I stayed the whole weekend interviewing people. And then at the end of the weekend, he walked over to me as he was closing up his booth and he said, Chris, come in, tomorrow morning, we’ll we’ll sign the contract so he sent away everybody else who was in the RFP. Nobody else got to bid. Sure, and we just went to negotiate the contract together and we took it over this. The other part of why I kind of think that way and operate that way is because the very first thing I ever pitched I lost. And when I asked the company why we lost, they said, because you didn’t come in and pitch in person and I said, Well, it didn’t say in the RFP we could pitch in person and the person said It didn’t say you couldn’t pitch in person, just never asked. So that was the moment where I was like, I’m never going to get out, competed, outhustled, Have someone be more creative, wiggle around the edges of how to get an audience or how to connect with someone again. I didn’t like losing the first time, and so after that I started applying these kind of like different approaches and and creative fearlessness techniques.

Jeffery:
That’s a brilliant story. I actually had hair popping up on my hands there or whatever in my arms since that was so exciting. I love that and it’s interesting because my mind was running a lot of things that I’m going to say that because of learning these stories. But and I don’t know if it fits around the type of individual, you obviously have a very competitive nature. You learn from your previous mistake to ensure that the next one was going to be success because you don’t want to set yourself up to go in and fail. You’re like, If I don’t have an edge, why am I going in to do this? And I think a lot of startups have to realize that there has to be an edge there. And it’s interesting when I teach classes at Seneca and other places, I came up with this game, so just like you, I was driving the class one day and I was like, I got to come up with something that’s fascinating. It’s gonna get people interested. So I thought about this, and I’m like looking around and things, and all I had was a stack of paper, which are my notes that I’m taking for us. But I handed out a piece of paper to everybody and I said, Okay, you’re going to get into groups of four. So everybody broken into four groups, and I said, take this piece of paper and here’s the rules is the only rules you have. Uh, you cannot tear the paper, but you need to fold the piece of paper up and as many times as you possibly can. That’s all the rules we have. Okay, Done. So everybody went. I got 15 minutes. At the end of 15 minutes, the groups would all say, Oh, you have to stand up and present. So one person presents and they tell you this scenario and what they did, so they have to share the results. So everybody stand up and say, Hey, I followed the piece of paper, uh, 65 times and then the next, and they would say, Well, how did you do it? And then you explain how I folded this way and I did this. But no one asks any questions. And but I only gave two rules, so eventually at the end, everybody would share. Maybe the top was 100. And then that person would say at the end, I would say, if I gave you guys five more minutes Do you think you could break all the records that were obtained already in this room? Everybody’s like, Yeah, of course I could crush that, and I would observe everybody. And I would share back some anecdotal stuff because they were all doing this. And then they would do the five minutes and they come back, and sometimes they would be at 300 or 400 because they learned from everybody. But very few people actually questioned what a fold was. What do you mean by fold? And so this I did this project on and off throughout the classes, and people would want to know what the winner was. So at the end of the five minutes and they did their next presentation, you would see the gap of change, and then I would bring up the thing I’d say, Hey, Louisa, I saw you looking around. I saw you going over that group shoulder. She’s like, Oh, no, I didn’t do it. I was not doing that. And I was like, No, no, no, you were This is good. What do you mean? I said I never told you. Couldn’t look at what other people were doing, you were actually observing what your competition was doing. So you’re learning something from the group, and she’s like, oh, man, I wanted to get up and go talk to everybody I’m like you should have There wasn’t a rule that said no, Um and then they would say one girl would say, Hey, what is the fold? And then she gave me a criteria what a fold was, and she’s like, Well, so if that’s the case, scrambled the ball up and she’s like, I win. So that was in another class, and I almost cried. I was like, Oh my God, that’s so genius. That’s brilliant because she thought again, further outside the box. And what I love about what you’ve designed here or the way you attack something, is that we all put ourselves into a box, and then we don’t think anywhere outside of it because we’re afraid if we try something different, we’re not going to get looked at or we’re going to get avoided. And what you’ve created is the excitement of that person gave you that contract because they saw that you were willing to spend three days of your time interviewing even if you weren’t getting any data out of it, you were so interested in compelled to win that that person had to say yes because they knew that you would have spent the next six months making the best product that they could ever use and that’s brilliant.

Chris:
Yeah, and I always I would say to my students, There’s like, you know, there’s ethics, there’s ethics and values, but there is no box, right? So just like now, like I’ve told you, there’s no rules on this assignment or like related to how you pitch or what you do, can this Can I do this? Can I do this? Can I do this? And then you’ll have, like, the most creative people, just like think about ways to win everybody over that no one would have expected. Right? And people like show up in the pitch. You have to be because you know you’d be very careful about how far you go and how you distract from your core messages. But people showed up in the pitch and, like had like three customers planted in the crowd. Prospective customers for this business concept that are real potential purchasers. And then they have them stand up in the student crowd, one after another, no one recognizes who they were, what they were there for. And then they say, like three sentences on why they would buy the product and then sit back down. There’s things things like this that are that are that are completely different. So that kind of like like, you know, kind of like hacks to to whether it’s pitching or presenting or winning business. Another example. That is how we applied that to very creative ways in terms of how we met people, people often come to me. Students will come in and say or startups will come to me and say like I really need a mentor and I wish that I could get the attention of this person and have them work with me. Say like Okay, well, I can tell them a quick, quick story or two, so I’ll give you one or two ideas or examples of creative fearlessness there. So when we had no network and we’re just trying to meet anybody who could be a business person of note, who would want to you know buy the platform, and I’m going to give this credit to one of one of my staff having seen these different ways that we thought and worked. One of the staff then came up with an idea and said, like her name was Sandy Wong and she was an account manager and she came up because I have this idea. If we want to meet rich and powerful people who are business leaders, why don’t we start volunteering at charity fundraisers all over Toronto? And when we go to the charity, fundraisers will take jobs that will allow us to be in close interaction with the senior executives entrepreneurs and then we’ll introduce ourselves and I was like, It sounds crazy. I love it. Let’s go do it. So the first one we went to was the Toronto Symphony Orchestra ball, and she signed us up to walk VIPs down the red carpet, and we went there that night, and we all had kind of targets and goals as to who he wanted to meet, and some of us met them and some of us didn’t. She met on a stand Mirvish, and she walked them down the red carpet. And of course, we’re like, you’re young, ambitious young people and these successful people say, are you in school? What are you up to? She said. I worked for this company. This is what we do. And by the way, if you ever want to talk to us and her pitch was, um, if you work with us within a couple of years we’ll eliminate all your advertising money, you have to pay in the newspapers. That was it, honestly, didn’t understand email. He’d understand the Internet, I don’t think. But he understood the possibility of making the newspaper bill go away. Right? And they became our biggest client for the first three years, right? But that was by going and volunteering like that. Another time, one of our team members who you would probably remember Wayne Kerrigan, came back and he was, Yeah, he was out about. And Wayne was like meeting. He was at an event. He came back. He said, Hey, Chris, there’s this guy I just saw Speak. He’s the smartest person I’ve ever heard in my life. You know, talk about business and strategy. We need him as a mentor and, uh, but he’s gonna be really hard to get to. Everyone’s gonna want time with it. But he’s working on a big charity project right now during the SARS recovery, to get tourism, to come back and business travel, to come back to Toronto after SARS, um, after that respiratory and was kind of like shut down the city for a while. So and Wayne said, like I think we should work and volunteer on his charity and donate our technology to the cause. And so that’s what we did. And it took six months or seven months of showing up and having him see the value of what we were contributing. But after that, I asked him one day after a charity meeting, organizing meeting that we went to. I asked him if I could have, you know, 15 minutes of his time to talk to him about raising money and how to make that happen. And this is back, you know, you know, to to date myself for a moment. This is pre accelerators and all of the incubators, and this stuff is not around it. Also raising money. Not as ever easy, but really not as easy as it as it is comparatively speaking to today. So he said, Yeah. Come with me for a minute. Yeah, I thought we’re gonna go to his office and sit down and maybe at 15 minutes, and he gave me some brilliant pieces of advice in 15 minutes. Instead, he opens up his calendar, you know, some. Okay, Uh, four weeks from now. Saturday, October the 18th. Um, you come to my house. Here’s the address. You got five hours. We’ll go through the whole business together. We’ll map everything out. Now. This guy was David PICO who was the head of the Boston Consulting Group in Canada. I sat for what turned into seven hours at the kitchen table of the head of the Boston Consulting Group to map out what was the trajectory of where the company was going. He even sitting at his kitchen table, he even named the acquirer of the company. And it came true in a sense that it was the company he named. It was their largest publicly funded competitor that eventually bought the company. Like every and the biggest decisions, we made three biggest decisions we made were based on that conversation at the kitchen table. But meeting him if I just said like, Hey, can you hang out with me? Hey, can you help me? I never would have got through. But again, just a different way of looking at the opportunity or the obstacle and figuring how to get there in a creative fashion.

Jeffery:
It sounds like a lot of the ways that you’re connecting with people, and the key is connecting in all of these stories that you found a way to personalize it and to get someone to believe in you as a person before they believe in you is your business versus taking the approach that, hey, everybody is going to buy my product or by my business because, hey, it’s a business and I’m doing really well so people are gonna buy it. But because it’s early on, yes, maybe in time, branding and all that stuff will help work and that give you that value. But when you’re really early-stage, you really have to get people to believe in and buy into you, which is you as a person. And then the rest of those things they’re going to support as they get to learn the way you work ethically, the way you hustle and all of these other things. Those are the pieces that are going to drive you to those home office meetings and being able to open up Pandora’s box and get that valuable insight or that valuable help that you’re looking for. Is that kind of sound more accurate?

Chris:
Yeah, that’s that’s that There really is more of the approach in terms of how how we’ve how I’ve looked at it. And that’s the part of the journey for me that I relish and enjoy being part of the most. Um, you know, And although we did take the company up to the point, where there was 100 and 14 people, I was honestly, never really at my happy and happiest in those times. I was happiest when we had nothing right, which is again, why I got attracted to the Schulich opportunity because there was a whole blank slate in terms of what to create. And the budget that I had to start out with was a dollar. So you know. But that was fun like then then my mind starts going to like what if we did this? What if we did this? What if we What if we actually turned it into something and we only had a buck for the first couple of years to create it? Then what would we then what would we do? So, yeah, I enjoy I enjoy that side of things connecting with people, finding contacts, breaking through, um, key moments, even in negotiations. So you know, I can give you like, uh, another example where I was sitting down. Remember back when Krispy Kreme, the doughnut company, came to Toronto Canada for the first time. And there are only very few locations and people would line up around the block and they wanted to get in. I was trying to get more brands for the platform to work with, and it was earlier before we had our big, big accounts. So Krispy Kreme. I was all over that I had, like, six or seven meetings with them had negotiated the contract. Everything all done came to the last meeting and the vice president, who was a young guy. It was his first executive gig, walked into the meeting, it was in the Krispy Kreme doughnut, their first location, and he walked and sat down the table and looked like he just like, you know, as they say, like seeing a ghost or he was just, like, really shook And he said, I just got off the phone with the headquarters and in the States and they’ve told me I can’t proceed with the contract because I’m not allowed to spend money on anything that is marketing. We only do word of mouth, and that’s how the whole history of the business was built. So I can’t do this. And even though it’s like a tech platform, I’m not allowed to engage in that kind of activity in terms of spending money. It’s like a corporate principle in terms of what we do and don’t spend money on. And in that moment, you know, I was like, I spent all this time and then but it only took me like, two seconds, and I asked the students in my classes what sentence came out of my mouth next, and I give them a chance to guess, and all kinds of gueses has come out. Only one student ever guessed the sentence that came out of my mouth like exactly, perfectly like to the letter and what came out of my mouth next was I’ll do it for donuts and then he was just the guy was shocked and he was like, What do you mean? What do you mean you’ll do it for donuts? I said, Well, if you only do word of mouth and everything you do is giving away donuts, then I’ll do the contract for donuts. You know, he was 20 $30,000 deal. I was. I’ll do it for, like, 20-30 $30,000 with the Donuts. And so here’s the way it’ll work every time I go speak somewhere, if I’ve got an audience of 2, 300 people, you will ship 2 to 300 boxes of those donuts and nobody wants to line up. Right now, it’s their hot commodity. So then what I would do is they would ship all the donuts to the speaking event, and I would have my team tape our business cards for all the business development people on top of the box. And then at the beginning of the 1st 10 minutes while he was speaking, they would hand them out through the aisles with the business card taped to the box. Man, I made so much money off of $20,000 worth of like doughnut deals, like more than I ever would have made if I took the money

Jeffery:
Right.

Chris:
like hands down, hands down. So I just like that kind of like, you know, obstacle. Okay, like, how do we get around the obstacle and and how do we find, like, you know, what is your point? Like connecting with the person, right? But also, you can probably see from a lot of these, you know, stories there’s like it’s like as you said, it’s like demonstrating the value, bringing something that the other person like makes them like, you know, sit up and really and really pay attention in the process. And I think that that’s like, you know, when the companies that I’ve coached or, you know, invested in I tried to bring that same mentality and approach to it and people will call me up for both for these investment opportunities, how I would approach things. There’s a phrase now within the community, um, within at least the Schulich startup community that people will and the students will use, which is like, What would Chris Carder do right? And that’s almost like, You know, I’d love to get that one day on like a T shirt. I don’t know. I can’t wear that T shirt myself around and I don’t want a T shirt, but I think it’s kind of fun. What would Chris Carder do? And sometimes people call me up for job opportunities as well to one person called me up and they were pitching like a top founder in the in the community that everybody knows for a job. And there were five finalists and they’ve got to the final five people. And it was a Friday night at five o’clock. The decision was being made at noon on Monday and the guy called up and he was like, I got to get this job and I ask myself, What would Chris Carder do? But I couldn’t figure it out, so I thought I’d just phone you. What would Chris Carder do? So it was a business development in partnerships, uh, job and remember this is like Friday at five o’clock, and I said, Oh, I can guarantee you the job 1000% by Sunday at midnight. Um, everyone else goes away. No one else gets a final consideration the job. But you have to spend the weekend to do exactly what I tell you to do. And and the guy was Okay, what is it? It’s very simple. Business development partnerships job got the weekend. It’s got to get him a client by Sunday at midnight. And it’s like, But I’m not working for the company yet. I said there is no box, right? There is no box like it doesn’t matter where in the company and like, free your mind of like we don’t need a car. We don’t actually need a contract. We need an email from one person to agree to take out meeting. And then when we get that email, you’re gonna flip it to the founder of the company and right? Exactly what I say. Don’t change it. Don’t freestyle just right. Exactly This dear so and so, so excited to work for your firm. I could not wait until Tuesday to get started. Please see below. Hired a Sunday right, Sunday midnight. He had the job everyone else had got sent home, right? So it doesn’t matter what it is in life, whether it’s a job opportunity or an investor or a client opportunity or whatever it is, um, there are ways to show that you can think differently and stand out in the crowd.

Jeffery:
Well, you’re taking the opportunity. And instead of reacting the way most people would when it becomes a negative or something that they can’t figure out, Well, how do I move forward with you telling me no, you converted that into a solution that drove and continue to keep that personal relationship moving forward. So with the Krispy Kreme donuts, you knew that there is a high value of interest for these doughnuts. People were lining up for days around the corner that if you converted that into a generator for you as a next step, you could still keep them. As a client, you could still talk about Krispy Kreme. As a client, you’ve got $30,000 worth of donuts, and now you have to use a way to deploy them. Have you ever seen the, uh series called Billions.

Chris:
No

Jeffery:
Billions is a Netflix are sorry crave show, and it’s about billionaires and its stock trading and asset trading. But at the end of it all, the U. S attorney, the one that runs the whole show, ends up getting fired. So he has to start his own job and his wife, who is a mental coach. She’s trying to coach him, that he knows this stuff and that he’s a hustler and you can figure this out. So he’s at the point where he’s got to make connections and someone needs to have in the show. They need to have a gun permit New York, and they’re like the rarest thing you can get. And she’s like, you can do this so he ends up going around building favors to get this for someone to get this for someone to get this for something to get that done, to execute, to build his brand. And really, what you’re doing is you’re taking that same mentality is that you’re trying to find a way with what you’ve got right in front of you. You’ve got someone that’s hot on the iron and they want to execute. They want to work with you. But the problem is that there are in a box and you have to either fit in that box or go outside the box and come up with a fantastic solution that keeps them as a customer and keeps that warm lead now into a closed deal. And that’s how you approach everything, which I think, hopefully. And today the audience will just get a huge amount of value from how you look at every situation versus looking at a no as a no, you’re looking at that. No is “wait a second, you were a little too quick on the wait I can’t do this” But since we’ve been dancing for the last hour or the last 10 years, or whatever it might be, I’ve got a better solution for you. And this is how we can work that forward.

Chris:
And I think if there’s like if there’s like, almost like a metaphor or a visualization that they can use for a problem, I would say it’s actually go back to your childhood and playing with Lego, right? It’s it’s that any problem or any situation if you just continue to stare at it as the as the thing that it is individually, then it’s very hard to work with. But if you actually just like, you know, take the pieces all apart and look at them. I have, like, have $20,000. I have $20,000 for the donuts. I have someone who wants to get this done. I have people who are high-end executives who don’t like sitting in line. I have places. I go, I meet with all those people. I like to have dramatic introductions, and people remember me so that I can win business. Okay, there’s the answer, right? Like it’s like you have to, like, pull all the pieces apart in your mind and just kind of see them in front of you and then reconstruct them and put them back together and re-offer them to the world

Jeffery:
And go quickly at it like you’re doing this in real time. They don’t have time for you to pull out a sheet of paper and start drawing an architect in this. Wait, Wait. I know you got to go. But I got an idea here, but you’ve got to really hone in on that skill, which is I can’t lose the opportunity I have right now. And I got to figure out a way to make it work and with one thing you can find something else that’s gonna bring the value. Um, and I have a million stories in my head running like crazy that I want to share. But I think what what I think the end result here is that when a startup is working with either finding a mentor or finding sales or get generating their first investor lead, they need to put time into understanding all the aspects of that relationship that they’re building and utilize it as best as they can without being forced, without it being demanded. But bringing value back to both parties so that they can feel that they gotta win out of it and that there’s a success that can come out or, you know, maybe not today, but in six months or whatever that might be, but find ways to create solutions. You don’t always have to take cash. You’ve got to find ways to build a better value for you and for that person that you’re engaging in.

Chris:
Yeah, 100% And when? When you’re looking at all these things, I think I always say to the students that there is like there’s something If they want to understand the startup community, and they want to understand entrepreneurs, and they wanna understand, you know, leaders, Um, the thing that separates all those people and that they look for when they’re engaging with other people is proactivity, right? So it’s like taking the game back to people. It’s not sitting back in any of those scenarios. It’s not like sitting back and hoping that something will shift in the situation or sitting back and hoping that suddenly, like you’ll just happen to rise to the top of the five people. It’s actually like being proactive and taking it forward and seeing what can be done to shift things, shift things up. We would do it in the middle of business development. So, like 1 strategy and again, another phrase that I think I personally coined. But maybe out there floating in the universe from other people like me, is the concept of a proactive reference check. Okay, so most people view a reference check is something that you added the list of, like, at the end of your business proposal or you wait. So, like what? You know, Level one is they’ll probably ask for references, and I’ve got a list of them when they ask. Right? And Level two is, I’ve got a list of references, and I really, well, you know, groomed and prepared those people for when the time comes, Level three might be I’m going to include the references right in my proposal as testimonials and actually have the client heard. So what would be level for of the reference check level for the reference check is the proactive reference check and get ready for this one, cause you’re gonna love this one. I would have my clients phone that leads when we were in the middle of an RFP or a pitch, and I would have four or five clients phone the person that we were pitching on their own. And either get them, catch them live, and they would they love this so they would call 456 times that they had to to catch the person alive, or they would leave elaborate voicemails. Okay, and I would have all manners of executives calling on our behalf. And eventually the person who’s like on the other end is like, what kind of like a client called does this guy running that, like people who are like presidents and entrepreneurs and, like national politicians and like celebrities are picking up the phone on their own time and calling and leaving impassioned like, you know, stories as to why they need to hire us, right and would shock people like every just shocked the system every time that that was happening, right? I mean, I remember one time after we did it, someone said to us and one of the one of our more famous pitches, someone said to us like, You know, how did you get a guy with a like a multi $100 million company to make that phone call for you? And I said, I said, My friend, you’re asking the wrong question. The right question is, when’s it your turn, right? And then he just laughed. You burst out laughing and said, Okay, fair enough. Fair enough. I went in, right, you know, because that was like the client now Why did the client why did the clients do that? Well, we took exceptional care of them, and they love the product. But like they also, we understood that as a startup, the early stage clients also have a vested interest in making sure that more clients continue to show up because they want you to see they want you to grow. They wanted to be stable. They want their bet. They made to be the right bet on a young company, right? So, yeah, these are just some of the different, like, you know, ways or things that we can deal with and like. That’s the big reason. Jeffrey, Why? I really enjoy working at actual like in Schulich and York University and working with all the students because, you know, more than having, like, you know, solving the problems through my own business or solving the problems through, like a portfolio of companies that I’m like invested in. The students have these questions like, you know, 100 times a day. So it’s like this, you know, incredible just lab of problems and scenarios and and and situations. And as I’m teaching people how to think like this for their businesses, but also for their careers and in life. It’s just incredible to see the impact that makes in boosting them on their trajectory. And, uh, and they really I can watch that I can watch as they as they go off on their on their mission. And, you know, I view it as like at the end of, like, a 10 year, a 10 year run doing this. Then they’ll be, like, you know, 1000 people out there, you know, or more. You know, maybe 1000 maybe 5000. Who knows how many people through all these conversations and sessions that will have done that will really get this core thing. And more than me saying, you know, tweak an item on your you know, projection Or, you know, uh, here’s a twist in terms of how you can view the product, which I enjoy doing, I know giving them this. This kind of talent and insight and way of viewing things is going to serve them well, no matter what they do in life, and help them over and over again to keep finding ways past obstacles.

Jeffery:
I love it obviously, uh, from the beginning to the end. Super insightful. Um, we’re going to shift over, and we’re gonna have a phase two because we are going to keep this conversation going because there’s so many more things that I do want to dive into, but we’re gonna We’re gonna shift over to the rapid fire questions just so that we can move through a little bit quicker for you. But I promise you, we will have for phase two maybe a phase three conversation if you’re up for it. But I do appreciate it. Chris, That was awesome. All right, so for the the, uh, rapid fire questions we’ll start with how did you get started in investing in startups? What was the impetus that drove you into this?

Chris:
The 1st company that invested in after selling our core business was a former employee who came and asked me to invest in their company and their approach to how they resigned of all things and the sincerity, and in the commitment that they showed to continuing to support the company passed their resignation. Um, made me believe in this person 1,000,000% and so they were the first person who ever showed up and asked me to invest.

Jeffery:
Awesome. And your favorite part of investing

Chris:
My favorite part of investing is getting the opportunity to be, um, uh to be working and and applying the things we’ve talked about today and teaching those things and then get to see it translated into success. And, hey, it doesn’t always translate into success. Sometimes it’s not, you know, not taken to heart or there’s other factors. But when it has and I and I get to see kind of some of my philosophies carried out and I have a stake in the game and something that comes out of that on the other side, it just adds an element of, uh, you know, just, uh, energy to be participating in that way.

Jeffery:
Okay, How many? How many companies do you invest in per year?

Chris:
Myself? I’m very, very selective, usually only one per year that I do, sometimes to one or two. And as of late, I’ve spent more time investing in Schulich alumni or student entrepreneurs.

Jeffery:
Awesome. I don’t love it. Any verticals you like to focus on

Chris:
The ones that I’m, like, enjoy the most are business to business, uh, software, you know, as a service solutions. I’m particularly, you know, uh, you know, adept in anything that’s in the marketing automation type space. Just because that’s where I’ve spent a lot of my life. But I have participated in all sorts of different, different things over time.

Jeffery:
Okay. Do you have any due diligence requirements that you look for to make before you make a commitment?

Chris:
My approach is, and I don’t think this is similar or super unique, but I really like to spend time with the companies that I’m invested in. So the best ones have been ones that have come after I’ve been serving as an advisor, a coach, not in exchange for anything, but just to build the relationship. Um, see how the person likes or doesn’t take advice. Um, do they make a promise and keep the promise? And, um, those have been the ones that have been not only the most, you know, successful, but also I enjoy working on the most because I know that even if they get a little rough for a little challenging. I’m going to still continue to enjoy putting my heart and my energy behind the person I think my — Besides that the staff person that I mentioned who has done very well and I love working with If there were early stage like, you know, um, you know, Mulligan’s that I would like over it would be for moving too fast, as opposed to really getting to know somebody by watching them, and participating alongside them in the business, and spending enough time.

Jeffery:
Okay, well, that’s good. Kind of wraps up. The next one is, What next question to? So do you lead rounds?

Chris:
No, um, I’ve you know, it’s rare that I would lead around. It’s more natural for me that I would say, Here’s my check that is waiting for you. You can tell people that it’s there and you can count on it, but you need to go find someone who’s at this next level. So I’ve often been the first let’s call the first contingent money that someone can go around and say, Well, I have him and here’s I’ll even sign a letter that says, Here’s the commitment that once you raise, you know, have commitments at a certain level that will go in alongside people. But I tend not to raise because they tend not to lead because between everything I have going on in school and my four Children, I don’t have time to, like put that level of diligence into leading the way for a group of people.

Jeffery:
I love that and a molding and diverse on that one, because I remember sitting with you at a restaurant and you had pitch to me and said If there was one thing I could do that would have changed the way my business ran is that if I had a pool of money sitting on the side and the whole company knew the money was there to protect us, and you could earn all that money at the end of the year, if you grew the business to this size, would you be more successful? And could you accomplish beating the odds going outside the box so that you could get that pile of money? And I remember you saying that and I’ve paddled out in my head all the time because I totally believe that the biggest factor of anything that prevents a startup from crushing it is cash flow and cash. And if they just had something on the sideline of those dollars sitting there knowing that they had them, how much risk would they put in so that they could crush it? So at the end of the year, they could get those dollars back? And, uh, I think that that’s powerful and you do it by giving them that early stage investment by saying I’m your first money in. Now go raise your money and I think that that would give so much energy and mental change to that startup. So I love it. Sorry I had to divert because that story has been in my head a long time. Okay, so do you reinvest and you take board seats?

Chris:
I do reinvest and I have taken board seats, but it’s not a mandatory thing for me. I look sincerely at the collection of people that are around the table and everyone’s relative levels of commitment. Often, though the founder has sought me out to be on the board because they know my reputation is I am. And I hope we all are, Um, but I But I have a demonstrated commitment of being founder first. So, you know, we we won deal that I invested in and alongside a friend of mine out there in the world. Uh, Derek Zito, who you would know as well, of course. And, um, Derek has a lot of the same philosophies as myself. And we were in a deal, and the founder came forward, and one of the two founders came forward and and just sincerely communicated like a life moment with his family and that he needed to go back to not being an entrepreneur because what that would mean in terms of the stability of his family and those things. And and when Derek and I looked at each other and we knew it was cool, sell it for now, not like this is like a terrible thing, but like, sell it for 12 when we know you could probably like, hang on and murder yourself for the next four years and sell it for 50 and you might wind up with no family at the end of it, and we don’t want that so good. 12 for 12. So people know that that’s like my approach. And when I’m at the table with the other board members or with once venture capital gets involved, that will always like my first question. No matter what is the incentive for me financially is always to the founder is tell me what you want. Tell me what you’re feeling. Tell me what this means to you. And then after I listened to them and give them all my advice on that, then in turn, what would you know? What I think or if it’s compelling to me? I learned that lesson because I had a really great one of my very first investors within data the first time I had an offer to sell the company, and I was just thought it was very important, like it was very earnest and young and I was like, I have to go tell him because we have this opportunity to sell the company because someone you know put this forward and had a lunch with me and and so I went to, uh to talk with him and he looked at me and he said, Okay, thanks for letting me know, uh, their plan than we do. And I said, Well, no, we have a far better plan and here’s why. And he said, Okay, would you have more fun working for them than working for yourself? And I said, No, I love working for myself and he said, Okay, thanks for letting me know. Okay, so let’s talk more about the business. He never even asked what the amount was. He literally never asked, and he just went back to talking about the company. So I had that very like, early example of my life, and he and the people around him continued to back me up in those moments like that. And so I’ve tried to bring that when I am in a board seat, try to bring that philosophy to the table is like, you know, I will never pursue the return of my ex thousands of dollars over whether the founder is gonna be happier. So that’s I think, more why I wind up hanging around the board and the founder wanted me there because I will always like to point out to them to that, even though what you’re about to do might ultimately make me more money. I’m not sure to be happy with taking that deal, because here’s what you’re, you know, unlocking into your life in that moment. So let’s just think about that, you know? And there’s just there’s lots of people who can just, uh, they’re better faster. But always just try and, like, bring the balance of what their life is gonna look like or how they’re going to, like, you know, how they’re gonna enjoy it based on what happens.

Jeffery:
Love it, you’re humanizing it, and you’re bringing a strong value of ethics into the whole principle of not only just investing but working with the startups and helping them so awesome. Awesome. The next question I have before we have three quick personal questions is, uh and you kind of answered it now. So I was fighting with myself. Should I ask it? But you may have a better story, and since I love getting stories out of you, maybe this will be, uh, when you’ll share. But it’s, um I was like, for that heartfelt story of a startup that you work with, um where she or he basically went from catastrophe or went from amazing to catastrophe or just something along the lines of just were able to overcome what it took to be an entrepreneur, just to share kind of that bigger that it takes to be, uh, to go through this because it may be, You know, people think that it’s an easy go, but there’s always look for that one tough story that someone really went through to really solve the problem. And it would blow your lid off that you couldn’t believe what they had to do.

Chris:
Yeah, I know there’s a couple that are like that in particular and, you know, I’ve been I’m going to say that I’ve been really impressed with how a number of the companies I’ve invested in have handled the whole pandemic right. And, you know, back, back when I faced a couple of like, you know, whether they were economic crisis is or like, you know, political crisis that kind of shook the world up and shook the markets up, and I was lucky enough to have a mentor or two who kind of guided me through that and I’ve been really impressed just with how in general there’s a resiliency within the philosophies of the startup space and that the founders feel right now that have allowed them to collectively share information, moved together and get past things. But have a number of companies, you know, without without naming them in particular, that have had their whole business model shook, Um, as a result of what happened with the pandemic and physical environment changing or ride shared changing, or like all these types of things and what people will touch or not touch. And, like, there’s a whole bunch of of just, you know, general shifts out there that I don’t think may or may not have back to normal. And, you know, I remember one conversation during the pandemic where um, the the founder, one of the founders Schulich founder, called me up and said, Hey, Chris, want to have a conversation with you because, you know, a lot of a lot of our mentors or advisors are telling us that, um, what we should do is we should fire three people on picking number of the year, but fire three people so that we can keep the rest of the staff at 100% salary. And but in our gut, we feel like that’s not what we’ve built, and that’s not the culture we built. And what we feel like we want to do is go to the company, be very transparent. Tell them that we as founders, are cutting our salaries by half and that we’d like the rest of the team to cut by like 25%. But if they do that, then here’s the exact date by which we can manage through with no other cuts. But we don’t know how to have that conversation. And our, some of our investors are telling, telling us, No, you can’t trust people with that conversation. They’re gonna all burn you kind of thing. And I was like, No, no, no, no, no, Like so let’s role play that conversation and this is what I would say. This is what I would do and how I would like, you know, introduce it. And they did that. And not only did the team carry through and everything hold together in the culture stay, they’re back to their next kind of like evolution and doing well again. So I think I’m proud of people who didn’t, like, you know, a number of people that I’ve worked with who didn’t take some of the immediate pandemic advice, which was like, coming out where people were just, like, screaming out of the gate, cut everybody slash everything, burned everything backwards, and that some people chose to go a different path. Now, I know some people had to do that, and I’m not criticizing people who were, like, legitimately forced in that situation. But I’m always proud of people who find a different way around that when we face that I had many conversations with, you know, my spouse at the time, and I would say, like we have a choice. We’re going to, like, you know, go another four months without getting paid. This is my life is gonna look like or we got a fire, Fred. Sorry, Fred, if you’re out there listening right now, But the good news is Fred never got fired. So, um and we’d always decide, Like, as a family and as founders and we decide. No, we’re not firing Fred. We’ll go another four months without getting paid. So I see that when I see people in the pandemic who are operating like that, that made me really happy. And I’m really glad to see some of those companies really succeeding as well, too.

Jeffery:
Awesome story. And I agree you have to again find a better solution. You don’t have to take the first thing that’s in front of you because everybody says it’s the right way to jump off the cliff, find another way and make it work for you and your employees and your team because they’re the ones that make you the success of the business that you are. So you got to find ways to adapt and adjust properly. I love that. Okay, three personal questions and then we can scoot because I know you’ve got a household of family members that need some French. So, uh, all right, So 1st, 1st question. Favorite sports team

Chris:
Toronto Maple Leafs. I actually camped out, um, for two days as a teenager in front of Maple Leaf Gardens to be the first the first person in Toronto with my friends whoever beat the scalpers in line to the tickets at the Maple Leaf Gardens back before Ticketmaster was deployed. So I am, like, hardcore. Used to travel on the bus to New market to see the new market Saints watched Tai Domi before he was a leaf up there. Yeah, I’m a leaf fan.

Jeffery:
Amazing. I saw them play when I was a kid, too. And, uh, the name that comes to mind when I was a kid. I don’t remember. His name was Val James. He was one of the first black hockey players. Tough guy. He’s actually got a book that he came up with and his experience in —

Chris:
I bought it for my son at Christmas. He’s reading it. Yeah,

Jeffery:
That’s awesome. Yeah, I was trying to him when I was a kid

Chris:
Yeah

Jeffery:
All right, Cool. Uh, your favorite movie. And what character would you play in the movie or would play you?

Chris:
Well, I Okay, so my favorite movie is the Unforgiven with Clint Eastwood. And I would definitely have to play, uh, Clint Eastwood’s character. And the reason why I love that movie so much is because it’s got this, uh, this concept of the core in it that you need to look at again. All the possibilities of who you are, what you’re capable of, and channeling all of that to protect the people around you. And, you know, whatever you know and what and what and what you love. So I I’ve always loved that moment where he realizes that, you know, for just a little while he’s got to go back to being a bad man in order to straighten out some ridiculous things that have been done in that town. And, yeah, I always love that, and I’ll always love. I always will always gravitate towards characters that are a merged combination like my favorite. You know, my favorite sci fi character is going to be Darth Vader. My favorite comic book character is Magneto. It’s like I want someone who’s playing the edges on both sides of the situation, light and dark at the same time.

Jeffery:
That’s awesome. I’m going to watch that movie, and I came up with these questions because I never at the beginning, I wasn’t personalizing it enough and getting to really understand the human side, and I was listening to one of the startups you work with, and in their podcast, they would ask, um What? What name? The name of the movie that depicts your life. So I kind of thought, Well, I want to know more about the character because the character to me to find so you really think you are and who you actually are, And then I can watch the movie, and this is where I get a lot more understanding of the person. So now —

Chris:
Don’t be Don’t be afraid of me after you watch them.

Jeffery:
But know that I love Unforgiven. It was a great movie, but I haven’t seen it so on. So this is going to be a great way to kind of catch that back up. But I can totally see that with, uh, with the Clint Eastwood characters. So I guess you’ll be walking around with a six string and, uh, pumping off lines with your little tiny cigars, I guess. But —

Chris:
that final, that final showdown, maybe it’s like the unbeatable odds that I like. Maybe it’s the fact that he walks in alone into that saloon with, like, 30 laws. And he walks out.

Jeffery:
Yep. I love it. Well, Chris, I thank you very much for your time today. I know, we went a little bit over my apologies. If you need any help with the French, I can. I’m in for free. I do speak French to help hold the family.

Chris:
I might call you later.

Jeffery:
I appreciate you jumping into this, and I really hope we can do a number two because I think there’s still so many more stories and things that we can pull out and share with the audience. Um, and the way we like to end the show is I like to leave you with the last word. Anything that you want to share to investors or to start up entrepreneurs. I leave it to you to share that. But again, thank you very much for your time today.

Chris:
Yeah, I’ll just say in parting. Just the Lego blocks. There is no box. And if you want to trigger your thinking and you’ve watched this episode when you face your next challenging moment, ask yourself, What would Chris Carder do? Thanks, Jeffrey.

Jeffery:
Alright, man. Have a fantastic day. And thanks again for all your time. Well, it was awesome. And I’m a big fan of Chris Carder. He has done a lot of great things in the environment. But of course, when you look at just the stories and things that he’s done with his own startups, it’s for me. It really resonates a lot, and I love his tactics. And, man, the juices were flowing with stories, and I’m glad that he was able to share a lot of those. There’s a lot of things that he talked about too. Pitching the wrestling and the T V show for Fox just on how he built value and made sure that, you know, you thought outside the box and instead of always being baked inside so big kudos to, uh, to Chris and the success and love what they’re doing at Schulich and thank you again for joining us and have a great day.

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