The cavnessHR podcast – A talk with Bobby McDonald
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Social Media links for Bobby Below!!

LinkedIn: https://www.linkedin.com/company/parlay-ideas/
Facebook: https://www.facebook.com/pages/Parlay-Ideas/
Twitter: @parlayideas
Website bobby@parlayideas.com
website www.parlayideas.com

Below is Bobby’s book recommendations:
The Manifesto of Entrepreneurial Democracies Alexandre Raab

Click on the link below to purchase the books from Amazon.
https://amzn.to/2KVkI3r

Free Resources

Parlay’s the tool for teachers in the classroom and at current, that's all we can give away. So if you
are a teacher or you know one, email me, and I'll give you my email after this and I'll give you an account for a year. We'll give away around ten or fifteen or so to the first people that email, help you get set up, chat with you a bit. Learn about how you're trying to incorporate discussions into your classroom and you get a free license for a year.

Jason: Hello, and welcome to the cavnessHR Podcast. I’m your host, Jason Cavness. Today’s podcast is brought to you by Audible. Get a free audiobook download and a 30-day free trial at www.audibletrial.com/cavnessHR. Audible has over 180,000 titles to choose from for your iPhone, Android, Kindle and MP3 player. Our guest today is Bobby McDonald. Bobby, are you ready to be great today?

Bobby: You bet.

Jason: Bobby is the Founder and CEO of Parlay Ideas. He was born and raised in Stouffville Ontario and is the middle of three boys. He comes from three generations of Irish, Scottish and Italian immigrants and entrepreneurs, most of whom came to Canada around the turn of the century. After finishing high school in Aurora Ontario, Bobby studied International Management at McGill University. While at school he spent time learning Mandarin and studying in China. Afterward, he started a clothing line, worked in various roles at CI Financial, and finally as a Solutions Engineer for an Enterprise Software company called Resolver. His current venture (and the reason he is here with us today) – Parlay – was born out of a frustration with the lack of engaging dialogue in the classroom, and a simple but powerful realization that the only way to build a better world is through meaningful conversation. Bobby, you have a colourful background, you’re doing a lot of great things. What’s keeping you busy now?

Bobby: Yeah. First of all, thanks, it's great to be here, Jason. What's keeping me busy right now is, like I said it there, is a company called Parlay Ideas. So it's an education technology company that the idea is about seven or eight years old now, the company itself is just over two years old and I've been doing it for just about a year and a half, full time now.
Jason: Bobby, on your LinkedIn, there's a quote that says, “I want to live my life taking the risk all the time.” What does this mean to you? What is the meaning of this?

Bobby: Yeah. So it's quote a by a pretty famous author who recently passed away, his name is Christopher Hitchens, and the quote is, “I want to live my life taking the risk - all the time - that I don't know anything like-enough yet. That I haven't understood enough, that I can't know enough, that I'm always hungrily operating on the margins of a potentially great harvest of future knowledge and wisdom...” In essence, what that means to me is that lifelong learning is the thing and that the road to wisdom is just this accumulation of your own understanding of your own limitations. But that there is real joy and a sense of meaning and purpose that comes from always feeling like you're on the edge of a new discovery for you personally, emotionally, intellectually, whatever it relates to, it’s just maintaining that curiosity I think is so important in life. While it can be unsettling and often is unsettling, once you sort of started to go down that path and realize the joys of that, there's no going back.

Jason: It's always amazing how many people just stop learning they have no interest in learning, they want to be in their own box, comfortable all the time. But in order for you to grow up, you have to be uncomfortable and learn more things. So many people don’t do that.

Bobby: Yeah, absolutely. I couldn't agree more. I think a big part of the reason why people don't do that is because they're not trained to do that. When they're younger, they're not necessarily encouraged to push the boundaries of their knowledge to challenge their own ideas, their peers’ ideas, their teachers’ ideas, their parents’ ideas in a healthy and respectful way. So I think that self-reflection and sort of critical evaluation of the world around you is really important and we need to teach that to young people early and then I think more people will do it as that life of self-awareness and self-reflection just becomes habitual.

Jason: Bobby, can you talk some more of the background of Parlay, why you started it and what your vision is for it?

Bobby: Yeah, absolutely. So the company started in second year university. So one of my closest friends, Mark, and I were looking around at the conversations or lack thereof that we were having at university and I was studying International Management, as you said in the beginning, and he was studying Politics, and we were looking around. It just seemed like there was no conversation happening about what was going on in the world of international politics, in the world of international business – and it's not like we were studying theoretical physics. There was plenty to talk about, all you had to do was open a newspaper or go online. So it seemed to us like there's something missing, there was a missed opportunity with respect to relating what we were learning in school to events and ideas that were shaping our world. Of course, the fundamentals are still important, but as students, the question of “why are we learning this?” kept coming up and it wasn’t just university, obviously, it's a thing in high school as well. So that was the first sort of eureka moment, so to speak, and then as time has gone on, and we've tried Parlay in many different ways. We once hired a developer from Craigslist (true story); we met him in the Starbucks inside of a Chapters. Which is a bookstore in Montreal while we were at school. We met him there once a week and he was building our first version of Parlay. We've also had Word Press sites and all this kind of stuff. So the idea has taken many different twists and turns over the years and has resurfaced and come back down, resurfacing and come back down a number of times. But as time has gone on, and I thought about sort of my life and a lot of the that matter to me. I realize that Parlay had become, in my mind, about so much more than just meaningful discussions in a class setting. It became apparent to me that the conversation was honest, open, forthright conversation where people are willing to challenge each other's ideas and willing to have their own ideas challenged and not be personally attacked by that. But to evaluate ideas rather than the person who holds those ideas. The ability to do that is sort of the bedrock of our civilization, and it seemed to be missing in our society. So Parlay, at its core, seeks to do that, and our vision is to empower a billion minds through meaningful conversations.

Jason: That’s a great goal. Bobby, is there a certain grade level, like high school, junior high, elementary level, that Parlay is best-suited for?
Bobby: So it's best suited for high school; teachers as early as grades four, five and six are using it in their classrooms and, obviously, I think that's fantastic – the sooner you can get students really owning the conversation that they're having, the better. But yeah, it has a lot of demands on critical thinking and peer feedback and that kind of stuff so high school is best. But, like I said, it's used earlier and it's a tool that you could use in law school or amongst PhDs very easily, wherever critical conversation can be had.

Jason: Bobby, how hard or how easy has it been to convince an educator to use your tool?
Bobby: So I guess there's two challenges. The first is technical and the second is conceptual. The technical challenges have certainly been there. There's teachers, especially when it comes to discussion, aren’t used to using, necessarily, technology because discussion is often just a very sort of natural and organic thing. So the technical challenges have been real and we've learned a lot about great user experience design and how to really hold people's hand through something, not because they're not capable of figuring it out, but because they don't care about your tool until they care about it. And so you really have to hold their hand through it and make it painless and fast in order for them to get to the point where they can get value out of what you've created. So we've definitely learned a lot on that front; and so there have been some technical hurdles and just the ease of onboarding and getting started and making it easy for them to derive value quickly. Conceptually, I would say most of the teachers we've been working with, so far, have been conceptually on board with what we're doing in terms of creating discussions that are more inclusive, that give everyone a voice that inspire more critical thinking, that encourage students to demonstrate inquiry, encourage peer feedback, and then generate meaningful data and metrics that show that engagement in unique ways at the class level and an individual level. Teachers, and educators in general, are very willing to adopt this kind of tool because they know that education, necessarily, must go in this direction and, ultimately, always has been going in this direction. So, conceptually, it hasn't been a super, big challenge but, like I said, the technology, you’ve got to make it easy for them early.

Jason: Yes. Bobby, on your website, there’s a part that says, “preparing students for life.” Then it goes to “… to think critically for themselves, then communicate their ideas, then listen to understand others and finally, give and receive constructive feedback.” From my point of view, really no one’s doing that – not kids, not people my age. How important is it to get people back to doing these things? What should they be doing?

Bobby: Yeah, absolutely. I think that in all aspects of life, whether you're in school, whether you are at work, whether you dealing with family members, whatever it is, I think, first and foremost, you have to learn, and listen from the other person's perspective, try to put yourself in their shoes, call it compassion, call it empathy, call whatever you want, really, really listen. And that's the first step to try to understand them. And then thinking for yourself is obviously to be aware, I would say, of your own propensity for different biases and your propensity for thinking a certain way because our minds take shortcuts because that's how we need to operate in the world. So be aware of those things and then decide for yourself what it is that you think and learning to communicate effectively, whether it's written or verbal. I think if you learn those skills, if you learn those fundamental things, and you practice them, and those become a part of the framework through which you interact with the world, then whatever it is that you do in terms of work, personal life, whatever it is, you'll be able to tackle anything. I think that's super important, especially as we go into a world that's increasingly uncertain in terms of artificial intelligence, automation all these different things, which really means anything rote, anything that doesn't require creativity or complex problem solving or critical thinking skills or the ability to communicate and empathize with humans, ultimately, that can all be automated. And so build this toolkit and you have the fundamentals down and you can apply them to anything and you can learn anything and you can do anything. And in a world where people are shifting jobs like however many times, that adaptability is probably the number one thing that you can develop.

Jason: Bobby, is Parlay a Canadian company, a North American company or where are your customers at right now?

Bobby: So we are a Canadian company, founded in Toronto, and we obviously operate out of Toronto as well. The incubator in Toronto called Ryerson DMZ and we have customers in Toronto, a lot of customers in the Greater Toronto Area. Of course, we've been spending the last year and a half really just building the tool and now we're getting out into the market. We have pilots and trial programs ongoing from schools in Korea, schools in the Middle East, schools in Switzerland and of course in the States as well. So we are making our way around the globe.

Jason: So with this business in different countries, how do the different cultures and different rules in each place play into what Parlay does?

Bobby: Yeah, absolutely. I think that sort of the one nice thing about educators, for the most part, around the world is, certainly the schools we work with which are oftentimes sort of international, independent schools, right now what we're seeing is that educators in general are people with whom these ideas that I'm talking about resonate because that’s part of the reason why they became educators, if not the major reason why they became educators. So everywhere you go, people want to learn, everywhere you go human curiosity and the desire to think critically and really explore things deeply, that's not unique to North America. So different cultures around the world are at different stages of that and approach that in different ways. But I think really a student-driven learning experience is very clearly the future; it's just going to take different people different amounts of time to get there.

Jason: Bobby, next, talk about a time you were successful in the past, what you learned from your success and what we can learn from your success.

Bobby: First, my first business, I would say. My first business was in grade eight; I spent an entire weekend one time with one of my closest friends at the time learning how to make wallets out of nothing but duct tape. We found a simple tutorial online and then we made all these different versions and we messed it up a whole bunch of times, went through ten rolls of duct tape, and then we brought a couple of them to school the next week, showed them to our friends and then before we knew it, we had half the grade or more with duct tape wallets which we would subsequently, for each student or each one of our friends, we would sort of take an order and then we would find out what they like, whether it's paint ball or hockey or whatever, and we would cut out little images and plaster them to the outside of the duct tape wallets to make them personalized. And so that was the first business – didn't make a whole lot of money at it, obviously, but it was an interesting, creative outlet and create something from nothing and sold it to people because they found it to be valuable. The lessons I learned there was don't be afraid to spend time on R and D; make people feel like what you've created is really for them, even if it is not perfectly customized, really take them into account, make them feel a sense of ownership and pride for having used or being part of a community or whatever it is. And then I would say, within that, find a way to create a healthy fear of missing out through that community and when they have pride in something that they’ve bought or created, they're going to want to share it. Give them the ability to do that as well and watch word-of-mouth be your best friend.

Jason: Great story, Bobby. Next, now talk about a time that you failed, what you learned from this failure what we can learn from this.

Bobby: Yeah, absolutely. So the first version of one of the discussion modules on Parlay is called the Live Round table. The first version of it was basically all the kids sitting at a table in a round table format, they're having a face to face discussion but on the tool, in real time, students are also rating each other as they're speaking based on four or more different criteria and those criteria have a scale so it's almost like a real time rubric and then there's comments that they can leave for their peers to see after. We thought it was a great idea; we launched it, put it in the market and it was way too much, way too fast, for the students. They were trying to leave comments and rate and understand what the points mean and the scale and listen to someone and think of something to say and so it was complete cognitive overload. And the lesson we learned on that was you have to really understand the nuances of the context where your user or customer or whatever is using your product. You have to understand what frame of mind they're in when they're using it, what are the other things that are going on in their life within that specific activity that they’re thinking about before you try to solve the problem. And you have to really meet them halfway. So a lot of times, with creators – obviously we’re no exception to this – you find that you have your hopes how you want them to behave and you try to impose your hopes for some sort of better behavior on the user and on the experience through the technology in the case of software, and you need to find a way to balance that with the reality of what the user can and will actually do. So it needs to be slightly aspirational where your hopes are there and they can get to those, but it can't be such a stretch that it's overwhelming. So we spent a lot of time building something that we had to reel back in and we learned that.

Jason: That’s great. Good thing you learned that early on the process, too. And not later on.

Bobby: Yeah, absolutely.

Jason: Bobby, next, talk about someone that’s helped you in the past and how they helped you.
Bobby: Yeah, absolutely. So in the last six months, it's been an ongoing thing; my girlfriend, Amanda, has really helped me sort of understand the difference between being reflective and self-critical and living with so much doubt that it's dysfunctional. So I think there's a real fine line to be walked between sort of living a life of doubt, which I think is healthy and important as this conversation is obviously on earth, but also having confidence in yourself and in your ability to execute. And even as a business leader, you have to take in all this advice – much of the advice that you take in is going to be conflicting – and based on all that, you have to find out what's really true to you or what makes sense to you and then act on it with confidence and formidably. So I think that's a really challenging balance to find and just, honestly, through conversations through a series of hand written letters, etc. she's really helped me sort of figure that out, which has been an immensely useful thing as I’d undergone this journey into serious entrepreneurship.

Jason: It’s always great to have someone like that on your side to support you.

Bobby: Absolutely.

Jason: Bobby, tell us something about yourself than most people don’t know. Your girlfriend knows this, most of your family knows, close friends, but most people who will see you day to day don't know this about Bobby McDonald.

Bobby: So I am intensely introverted, for lack of a better term. When I was a kid, I would rather stay in my room and work on a giant book of Mensa puzzles or play Lego than go outside and play with other people. I've become more social sort of out of necessity, and I'm getting to pretty good at it – kind of started in grade eight or nine. But it’s still hard every day. And if I'm in a place that's really social for too long or if I’m doing a pitch or presentation and there's too much engagement and it's too stimulating, I will always leave that environment feeling overwhelmed.

Jason: I'm a big time introvert, too. Me, I can't do small talk; I don't care about the weather, I don’t care if you’re doing good, just take care of business and let me leave.
Bobby: Yeah, absolutely. And there's a time and a place for pleasantries. A close friend of mine once said to me, if you can try to make every interaction that you have with another person the most authentic and real and unbelievable interaction that that person had that day. then you'll make a meaningful, lasting impact on them. And while I don't always live by that, I found that to be an interesting approach.

Jason: That’s great advice. Bobby, I understand you have a book to recommend to our listeners.

Bobby: Yeah. Actually it's funny, the friend who I just mentioned – his name is Mike – his grandfather actually wrote a book called The Manifesto of Entrepreneurial Democracies. It’s little book, it’s like 150 pages, the print is pretty big (less than 150 pages, I would say). It’s written by my friend Mike's grandfather; the author's name is Alexandre Raab – he was a Holocaust survivor, he’s a true family man, he moved to Canada and started a nursery here that became a big, big company called The White Rose. He passed away a couple years back and after he passed away, I think it was my friend Mike’s dad gave me this little book called The Manifesto of Entrepreneurial Democracies. And I just read it for the first time, finally, a couple months back and it really blew me away. If you go on Amazon, it's available; there's like zero reviews, etc., etc. But I highly recommend it.

Jason: Thank you. Bobby, I also understand you have something for our listeners today.
Bobby: Yeah. We we're talking about this earlier – Parlay’s the tool for teachers in the classroom and at current, that's all we can give away, because that's what we have. So if you are a teacher or you know one, email me, and I'll give you my email after this and I'll give you an account for a year, we'll give away around ten or fifteen or so to the first people that email, help you get set up, chat with you a bit, learn about how you're trying to incorporate discussions into your classroom and you get a free licence for a year.

Jason: Thanks, Bobby. That’s very valuable. So, Bobby, can you share your social media for either yourself or your company so people can reach out to you?

Bobby: Yeah. Personally, I'm not really on social media but definitely the company is – @ParlayIdeas is the Twitter handle Facebook as well. My email is bobby@parlayideas.com and then that website is www.parlayideas.com.

Jason: Bobby, we’ve come to the end of our talk. Can you provide any last minute words of wisdom or advice for our listeners on any subject you want to talk about?
Bobby: Yeah, I was thinking a lot about this a little while ago. Google the term “punctuated equilibrium”. It's a term from evolutionary biology that I learned in Anthropology class from second year. But Google how it applies to life and business and sort of the growth mindset more generally. It's super interesting and it's a framework of understanding how species are, in this case, individuals, evolve and grow that has given me solace and helped me understand myself a lot better.

Jason: Thank you, Bobby. Bobby, thank you for your time today, I know you're a busy person; being an entrepreneur is a 24/7 endeavour so I really appreciate your time today. To our guests, thank you for your time as well, and remember to be great every day.