Subscribe
Share
Share
Embed
The podcast where relentless curiosity meets leadership transformation.
Hosted by Tyler Chisholm—entrepreneur, CEO, and lifelong learner—Curious as Hell is the go-to podcast for leaders, innovators, and trailblazers who believe that asking the right questions can unlock new possibilities in business and life.
In each episode, Tyler sits down with top executives, entrepreneurs, and thought leaders to explore how curiosity fuels innovation, builds stronger teams, and drives personal growth. Whether it's uncovering the leadership strategies behind top-performing companies, unpacking the mindset shifts that foster resilience, or challenging conventional wisdom, Curious as Hell delivers actionable insights that help you lead with confidence and creativity.
If you're a growth-minded leader looking for fresh perspectives, practical strategies, and inspiring conversations that push boundaries, then you're in the right place.
Hello and welcome to Curious as Hell, a podcast about leading and growing in today's world. I'm your host Tyler Chisholm and I'm excited as I always am to be here with my guest today, Bobby Rissette. How you doing, Bobby?
I'm great, Tyler. Thank you.
Thanks so much for coming on, fitting me into what is surely a busy schedule. You've had a lot on the go. So for our audience, a little bit of history. Bobby and I first met in, I think it was June 2020, in the very early days of a company that you have grown and you've evolved and you've exited, Virtual Gurus. So why don't we give the audience, if they don't know you, which most people that will listen do, give us a little bit of the story. Give us the cold notes. I know it's a big journey, especially where you've landed in last six months, because that's when things have really changed for you.
Wow, was 2020 is so long ago. So yeah, I'm Bobby, founder of Virtual Grooves. So about eight years ago, I actually started Virtual Grooves because nobody would give me a job. I mean, you know, they call me a trifecta, right? Like, and we've talked about this before, but a queer woman, but an indigenous woman and in tech. So.
Lifetimes.
That's the kind of hits a lot of angles for different way that people weren't ready to support in 2016. And so I was out looking for work constantly. Nobody would hire me. And I started seeing on Kijiji like, know, freelancer, virtual assistant needed this and that. So I started sourcing myself out and virtual gurus was born in a way of being able to provide myself work because nobody else would give me the opportunity. I'm happy I took that that gamble and went for it.
but who would have thought what it would have exploded to. And then on the side of Virtual Grooves, which I have now since exited, and we can get into more of that, I am the chair of the Queer Tech organization. Queer Tech is a organization where we are creating and creating and building the next generation of queers in tech.
Is it a Montreal, I think? Yeah. I grew up Montreal. Whenever I see the word Montreal, catches my attention.
Yeah, that's amazing. It's great organization to be a part of. I am also the chair of the Indigenous Prosperity Foundation. So what we are doing is the same. We built a Launchpad with DMZ in Toronto. And Launchpad is where we are helping and giving resources to the next generation of Indigenous aspiring founders or people who want to get into business. We're giving microgrants to get them through so we're not taking equity.
and helping people kind of explode and get them all.
So, it's giving them the money they need to get it going. What would constitute, I'm just my curiosity, how much is a micro grant?
Well, right now we're giving anywhere from five to 25. That said, we're pretty new. are still raising money ourselves. But we also have launched a financial literacy game. It's an actual board game. And it's a financial literacy game because most people that are in the indigenous communities, myself included, when I first started Virtual Grooves, I had no financial literacy. I didn't even know what like EBITDA meant. So we created a board game.
And that's live right now. And it's out there. We go into communities and teach people how to play it. And it's showing youth financial literacy when it comes to starting businesses, to saving money, to everything. And on top of that, we built up the Walk Together program. So we're going into the communities and walking together with them to show them that it doesn't matter where you live and who you are, you can still start a business and be somebody.
I love it. And I love if I'm listening to all these things, you're putting yourself in the middle. Like you build the platform to allow people marginalized often who weren't able to get access to work to get access to work. Everything is a platform. It's a game. I love that trend when I look back and as I've to know you and I see the things, you're always in the middle of bringing some group to another group or bridging the gap for people.
Right, because it's needed, it's needed out there. And I mean, if there's a few things that I'm passionate about, it's obviously business, it's obviously scale, it's a building, it's indigenous, anything to do with my indigeneity and anything to do with my queerness. So it's why not just put it all together and help everything.
Well, the easiest way to show up is by being you, right? Yeah. Yeah. If I spend time trying to be someone else, it sucks up too much of my energy. So let's talk a little bit. Let's dive into season one of the show is the risk of certainty. And I met so many leaders that are like, what do mean the risk of certainty? And I think about the early days and I listened to our first episode this morning. You are so clear. You were so concise. You're like, this is what we're doing. This is how we're doing it. There was a high degree of certainty. And I'm curious now as you look back.
Yeah.
what was the balance and how did you draw that balance between staying curious and staying open to what was an evolving business, but portraying that air of I know exactly what's going on because with investors, with customers, they want that confidence. Let's talk a little bit about like the early days even till now how that's evolved and how did you juggle and balance those two things in that journey?
You know, in the early days, you think that the way you're visioning it, everything is the way it's going to go. And you're kind of stuck in this like tunnel vision of this is where it's going to go. But you don't realize that along the way as different things are happening, that it's actually not going that way. It's actually going this way. It's gearing hard to the right and you are going straight still thinking it's going that way, but it's not. And
you kind of become into this because you're just so focused on it really, but you become kind of, you're not seeing it, which way it's really actually going. And one of the things for me was trying to recognize that at very, like at the early stages, trying to recognize that as opposed to having people from the outside, like my advisors at the time or mentors telling me, whoa, hey, or employees.
And at the time I had realized though that I was so stubborn that this is where it was. And it was totally going this way.
risk of certainty was a real thing for you in the early days.
Yeah, but I was like, this is where it's going. And it wasn't. And, you know, at the same time, though, if I think about it, I think that's part of the way of learning. Because, I mean, you don't know until you're in it and then you have to learn it when you're in it. You're curious and you got to figure it out as you're going through. And I didn't know a lot of that until it was almost too late. So I would say that a lot of those things were they ended up being mistakes for me. But.
What makes it all better for me is the fact is I was able to fix those mistakes at the time and learn from that mistake and move on and get it back on this.
Before it goes too far too. So if you think about curiosity even as a concept, would you say you're more curious now having gone through those experiences than maybe you were in early founder? Founder Bobby five, six years ago?
Yeah, I would say more curious now to the point that I'm so excited to start my next venture or next ventures. Because I think now once a builder, always a builder. But I want to now do that. And I'm to be able to apply a lot of that where before it was really about learning that way and learning how do you stay curious in it and really get continue that drive forward without, let's say, the stubbornness or the, you know.
I'm kind of an inexperienced founder that thinks this, but this is really what it is.
What's the balance though? Because you need a little bit of that. I almost call it like blind ignorance. Yeah. Which with a little brute force because getting through those initial stage of taking something from an idea from your kitchen table, which I know you did and bootstrapping it, to actually getting people to go, I think there's something going on here. I'm going actually give you 170 nos. I think you have heard no a lot. Where's that balance do you think if there's a founder listening right now of like, you got to be a little bit stubborn, but you still have to at least keep half an ear open. How do you manage that?
To be honest, once you start opening up, how my mom will say, expand your horizons. And once you start opening up your minds a little bit and opening up your curiosity, I guess I would say, and really driving forward in a way of you're not afraid of what that outcome's gonna be, you're just kind of figuring it out, right? Once you kind of open up a little bit more, you start taking a little bit more risks. They might be a little bit more calculated risks or they might not be calculated, but the more that you go through, you start getting a little bit more...
kind of, I guess, understanding the errors that could happen. For me, the moment I started realizing that I wanted to be a risk taker, and I was so new and nascent to being a founder. Like, I didn't even have a grade 11, you know? And it was like, I had no idea what I was doing. I just needed to figure it out as I went. And then as I started figuring it out as I went, it's almost like, you you're getting on a bike and you're learning to ride it. You start kind of getting your training wheels taken off and you're going.
I started being able to take more risks and understanding that, you know, it was okay for things to go off the path, but it was okay for me and it was up to me to bring them back on. You know, and I started learning that kind of the hard way. And I think as you go further in, you start really learning that.
Was there a moment when you actually decided I'm going to be Bobby the risk taker? Like, was that a, like you made it sound like it was very much probably through conversations and a little bit of self discovery. You woke up one day and said, if I want to build, I need to take risks.
Yeah, it probably was the pivotal point of my growth and Virtual Grooves' growth that made me realize that this has somewhere to go. This has the ability to go somewhere big. And it's only going to grow as much as I grow. And if I don't grow and learn and try to learn and pivot through things, try to expand my horizons, then the company wasn't. Yeah, she's watching this. She's going be proud.
hear your mom's voice going.
I bet you.
Yes. I really knew that the point really for me was honestly when I started going through those 170 nos. A lot of the 170 nos were, you're not scalable. You have no experience. You have this, maybe let's not talk about your queerness. Let's not talk about you being indigenous. Let's, stuff like that.
I started getting to a point where I was going to let it beat me down and let me make a decision, which would have been to throw in the towel early and give up because that's what people were telling me to do. And I realized that I can't. There was a light bulb moment that went on and it was like, you can't, you have to be a risk taker. You have to stand up. You have to talk about your identity. You have to be yourself because
All of that before that was me trying to be somebody I wasn't. And then the moment I started being myself, talking about who I am, being all over the media, talking to things, being on podcasts, being vulnerable, the moment I started doing that was the moment things opened up for me and was the moment it just went, and I couldn't keep up.
What was the moment when you made that? Because I appreciate that. And we read that, oh, when you're yourself, people gravitate towards you. And my business partner always jokes, you we wait to have trust to be vulnerable. But the second we're vulnerable, it immediately creates trust. yet everyone's going to be listening. Oh, yeah, that's great. That's for you guys. That's something you've experienced. you know, you're on the journey. Was it a coach? it a vision quest? Did you go for a walk in nature? Like, I'm curious how you went from like, falling in line with you should fit a certain mold that wasn't working for you to actually making because it sounds pretty
fluid now, but I'm imagining at the time, that was a lot of soul searching.
It was. You know what the moment was, and this wouldn't have anything to do with the mentor or me putting myself through Harvard or any of that kind of stuff, like going and figuring it out. It had to do with somebody that worked in my platform, which was the whole reason behind me building the company in the first place, right, was to help underserved founders. I was on a radio show and I was talking about why I built it. And one of the questions was something about why did you build this and why now?
And when I explained how I was a queer, Indigenous woman in tech that nobody believed in, and I've been struggling my entire life to prove myself, and I said that on the radio. And it aired that day and then the next day, and the next day, a young, beautiful trans woman showed up at my office at the time and was actually on their way to do something not so good, because they couldn't be themselves at their job.
at the time. They were forced to wear suits and that's not who they were. And they heard my story and they cranked the wheel, stopped, Googled where I was, came to my address and showed up and was just like, you kind of saved my life because you're vulnerable. You told me this. And all I kept thinking of, she can do this, then I can do it. And it was that that turns the whole thing for me where I decided I was going to tell my story and tell my truths and be who I am.
Because at the end of the day, if I can just inspire one person a day, then I'm inspiring a nation. And that's the whole number one thing I went for.
Great story. I love that. I love that they didn't just message you or text you. They physically came to you. How big was your team at that point?
Basically came inside my office. Three.
That's even better. And all three of us. So thank you for, again, why I love chatting with you because you're so honest and you just show up. which is the whole point of the story. But now building a culture that also has that same level of authenticity. And as leaders sometimes we're like, well, I'm gonna act a certain way, but you know, or I want you to act a certain way, but I'm not gonna show up like that. Did it have the same impact on your team? Did that leading by example is the best way, not the only way?
You
It did. In the early days, I would say no, because I didn't know what our story was then fully. I didn't know how to talk it out as much. Like I didn't even really do a lot of media things or podcasts at the time. And once I started talking about it, then it really attracted the right employees for me. I would say this last three years, the employees that worked at Virtual Grooves were the best Virtual Grooves has ever had. Because these employees,
were there not because they wanted a paycheck. mean, let's be real, we're a startup that is VC backed. can't, we couldn't pay a lot, you know? But we certainly gave everybody a fun space to work, bring your dog to work, work in your slippers, here's some lunch, like, you know. Their perks helped, but I mean, they weren't the why. The why was every single person that came through those doors to work for us were because they had a story and they felt that that
to balance it out.
was the place they could be where their story would be accepted. And it was. And I would like to say that in the later days, all of those people who, know, now dispersed, some are still working for the company, some are not. I would like to say that they'll remember that job for the rest of their lives because of that. And for me, that is success right there.
Well, hopefully they take that influence. I Calgary, been on this journey of like, we need more exits so that those people can go in and infiltrate and inspire other organizations. And I think we were just, we're just on the journey, right? It takes time. I mean, you've got to have some of those spin outs for that to happen. Thinking about, like you mentioned earlier about when Bobby the risk taker showed up, I have a persona, it's Bobby the risk taker. How did you maintain that in your culture where people also felt safe to be like, well, I think this is going to work. I'm pretty certain.
But I'm willing to try because I know I'm not gonna get lambasted. You can call it psychological safety. You can call it just creating a human environment. How did you balance? Because as you grow, those can get tricky sometimes.
They can. I've questioned myself many times on the question of, does everybody in your company feel 100 % safe at all times? Probably not, right? And how can you make them feel that? And deep down, I don't think there's any way that any given time, every employee is 100%, feels 100 % psychologically safe. And as the leader, you take that on your back. know, like you-
No joke.
Okay. It hurts, I think you more than them. In a way, when there's calls you have to make that aren't okay. you know, so when I started really taking a lot more risks in my decision making, you were going to start selling this service, we're going to do this, we're going to build the platform, we're going to build AI, we're going to do this. I knew, I knew that, you know, it could be half and half, depending on the decision that some employees were good with it, some weren't. And obviously, I would hear them out as to why they weren't and I'd say, okay, great.
We're doing it, right? Because this is, at the end of the day, be self to make a decision.
The leader still needs to make a decision. I can be as curious as we want, but we're going this way. That's curious in life is one thing, curious in business, someone's making a choice.
Somebody has to and I get that your decisions aren't going to be, people aren't going to side with your decisions at all times. I think my number one struggle was that I wanted everybody to trust my decisions. And it was really important to me too. And so I tried to make everybody happy versus understand the risks that needed to go. And I think that's where mistakes happens, you know? And for me, not saying there was a big mistake or anything, but there were mistakes that happened because I...
I was trying to make everybody happy. And then when it came to the point where I said, you know what, I'm just going to do this and thank you. I'm hearing what you're saying, but I'm going to go this way and this is where we're going. Let's go. It wasn't until then that really good things started happening, like the scale, the growth. So I wanted to them to think, and I wanted to think that the employees at the time that maybe weren't happy were saying, okay, you know what, I could trust her decisions and I understand this, but.
You know, it's hard when you're in a scale up and you're moving so fast and there are balls being thrown at you at every right, like every angle and you're trying to catch everything. It's really difficult. And so the employees probably had the hardest time during that fast scale.
is, did you lose some key people at those times? self-select and we're all entitled to self-select. You chose to be on the journey and it's going to move.
You are.
Right. And I would have talks with them on that and same with our HR team and everything. And we would say, you know, you have the right, if you want, we can like help, you know, you start looking for work. And so this way you're not in, you could still give you two weeks notice and, know, look, be cool. Cause it's not.
Let's be cool about it. Let's be shitty. Sometimes it gets like, I'm wrong, you're right, you're right, I'm wrong. And nobody wins in that. Versus the, hey, we're no longer aligned. That doesn't make you or me a bad person. Let's move forward. That's a very different environment than a lot of places end up being. In my personal experience. Even earlier versions of me as a leader, like I was kind of shit sometimes. I wanted to be validated and right. And even when, like looking back, I wasn't right. All the time. Shocker.
I mean, you know, now I can honestly say at the time I might've thought I was right on all my decisions, but I certainly wasn't. Nobody is. You know, and yeah, you know, and I started realizing that more as you go in. And I mean, that's nine years of running one business, one scale app that went from zero dollars to however millions. So, I mean, it's great that I learned from it. And I think the employees all learn from it. But if there's something I would do different moving forward.
value of reflection.
is I would be taking a lot more calculated risks from day one.
worry a little bit less about having everybody.
Yeah, at the end of the day, you can't carry everybody on your back at all times, right? So you just got to go. And I think that's something that I've learned.
Just a random question. So nine years, how many versions of the business existed in that nine years? Four versions, five versions, ten versions, 150 versions, five solid like life cycles.
And I told myself from day one, and I'm at peace with this, is that the moment the company started losing the vision that I wanted was the moment it was my time to go. And I I'm not heard about passing the baton on and saying, good luck, run it, let's go. I'm not heard about that. In fact, I was really excited about it because...
It just made me go like, my God, I'm passing the baton onto my legacy, you know? And it's this amazing feeling.
Well, as to what about being a builder? Yeah, can build other things. I build. I can build other things. There's a sense of freedom that probably was a little bit intoxicating in that moment of like, oh, I'm kind of free again. Yeah. Yeah.
I know. They don't have to set an alarm and I was sleeping in and living at the campsite all summer.
Sounds like a lovely way to spend the summer in your RV because I follow you on Instagram. How many versions of you, five versions of the business in those nine years, how many versions of Bobby in those nine years?
You know, I would say it's the same version, one version. However, I would say just a little bit more of a version that has gone through the different areas, like, you know, the seasons of running a business. I'm a seasoned version.
I like that. How do you like your leaders? I like to move in season actually, but there's only one way to get there. You've got to go through the time. You've got to go through the drying out process, however you want to do the season. Thinking about that certainty that you had to have, that you have to have any time as a leader. But how is that balanced of like when you were standing up on stage being like, I'm 100 % certain, even in the back of your mind, when you're like, well, maybe that's true. Maybe it's not true. Have you become less certain with time or is it that
Like to your point, I'm certain, but I can de-risk it a bit. I can look at it from different perspectives. Has the certainty changed or has the rigor and maturity that gets applied to it changed?
I think it's the maturity that gets applied to it changes. So, at first you're essentially just throwing spaghetti at the wall to see what works and sticks, right? And you're like, okay, is this going to work?
You're throwing it confidently. You can't just lob it. You gotta throw it against the wall.
And then you're this is going to work. 100%. Right? We're now, it's, I'm just lobbing nicely like a piece at a time and like, you know, and I know this is going to work. I'm just more calculated about it. more data driven about it. I'm more understanding of what's probably going to work, what's probably not going to work. And if it doesn't, then I'm creating enough data that I'm going to understand the why. So then I can go back.
As you sit back, as it all falls on the floor.
I learned something I didn't blow something up.
Exactly. Yeah. And I think that that's like kind of in the ends where it really started going for me. I wouldn't say in the end because it's not in the end, but in the last year was, you know, I started making a little bit more of those calculated decisions based on what others wanted and on the board and this and that. But I think for me, it was that
I was really proud of even going more calculated into it and saying, okay, wait, if we go in here and we're going to do this and we're going to go here, then this might happen, which is great, but what if this happens? So how do we get, take that data to go to here? And when you would apply it, it'd be a little bit of a slower path, but all of a you would see like a up.
But less risk and more to show for it. Yeah. I love that strategic curiosity. Like we could go here and here and if it goes wrong, this is how we pick. And when you're laddering up to a board, that's kind of what they want to hear too. That you've thought through it. Not just what if it doesn't work? It's going to. That's not acceptable.
You know, and I could say that, you know, my board, I mean, bless them because probably for the first four years, they were like, my God, this girl's like, just like a bunny rabbit, just got this and this this. Where near the end, it was a little bit more easier of, well, here's why, and here's what we're going to do. And if it doesn't work, we're going to go here. And here's why it's going to work though, because the data. And you come, yeah, you become a little bit more calculated in a way where you start trusting yourself more because you're making that right decision. But.
It didn't come easy for any of that, you know, and you had to kind of learn the hard way. And I think that for some, it does come easy and it's okay too. It just looks like.
it does it just look like it does? I think some of us do a good job of making it look like everything below the water is fine.
Because even before when before we started recording we were like, you know, everybody was you know saying my god Bobby made it so easy like Bobby's got this this and that and say yeah, well, it's not easy. It was probably the hardest thing in my life, but
I like to push back on that unless you take the time to really talk to somebody, you don't actually know what they're going through. You don't. But we put out good stories on our social medias and we portray in the world. Well, I think it's the curse of social media in general. So that's another podcast for another day. We portray the shiny bits. The image that you want to portray to the world. But I think when I sit down and what I love about this and why I wanted to have you on the show is the authenticity of like, yeah, okay, no matter what it looks like, here's what it's really like.
He was what's really like, like, it's a bit chaotic. Yeah. You know, and, and yesterday he just did a talk at platform and platform Calgary. And it was amazing. It was with the EA 100 and then platform together came together. And I told my story of, you know, from start to exit type Dylan. And, and, know, it was a thing of, telling everybody that you don't know what's going to go right. You don't know what's going to go wrong, but you still just got to build it anyway. You got to go.
Give them a plug all day long.
And now's the best time to go. It's just like build, build, build and go. And it might work, it might not. You might exit in nine years like I did, you might not. You might be in it for your life, you might not. You might sell, you might have to raise money, you might not. And it's just a build it anyway and go and just trust that you're gonna learn along the way. It's okay not to know everything.
My change, right? There's a lot of right.
Let's we're getting to the journey of the nine years, but the last six months has been probably a big, this is the first time you've exited. I bet next time you would know a lot more than you need this time. How did that balance of curiosity, certainty, your relationship with the board, your relationship with, because while you're in a sales process, you're still running a business. Things are still moving forward. And oftentimes I've heard founders been like, the sale didn't go through and I lost four months because I stopped building. Talk to me about the last six months and how you kept the curiosity and certainty balanced.
And maybe, of course, always a chance to say what you might do differently, but let's save that for that.
Well, know, all honesty though, back in May, so May, June 2025 was when we really decided we were going to do what's called a dual track. And so we were going to go for either raising more money or selling the company. And it's not because we weren't scaling, we were scaling, we were in growth mode and everything, but you're at that part.
where it was time to really focus on profitability and really focus on becoming super lean. So we did agree that it would be better for the founder to kind of step aside, but still be a part of the business. And I was okay with it. So I actually stepped into a president role, which was really still being the face of the business. I was okay with that, like, because I was starting to become decision fatigued and I was...
I wouldn't say losing my mojo, but getting to the point of nine years where I just, I wanted to enjoy my first year of marriage and just relax. Phases and stages. And so luckily my successor was working with the company and I essentially brought him on for that. And so he took over and then we did get an offer right away, which is good. And so for me from like June until the sale went through in November, I...
really wasn't a part of the virtual grooves at all, other than, you know, the board meetings, because I sat on the board, to really being a part of some of the decisions, not all of them, to really just chill in. Like I worked maybe an hour a day. Yeah, like I was living the life and I got the taste of it. I realized more than anything that I was ready for some downtime, you know, and so I
Right up chillin'.
It's going be a hard transition for lot of founders. got to really get, you got to kind of know yourself on that.
And I thought it was going to be a hard transition. I really struggled a little bit mentally thinking this is going to be really hard because all I've known is virtual girls. All I've known is the hustle that I've done for the last nine years. And I was so afraid that I wasn't going to handle it well. And so was my wife. My wife was thinking, wow, this could go one way or the other.
There stories where the wife might be getting encouraging you to go back to work. I've had many wives have been like, my husband's been home and I was driving me nuts in that scenario. Because that's like you said, you've all you know and it was all encompassing for you.
thought for sure I was going to drive her crazy like within the first week. That's great. But I will say during the time, what was really uncomfortable was knowing what was happening and not being able to tell my employees. Like all of these people came to work there because of me. All of them trusted me. All of them loved the mission and they started seeing the mission was going towards a sell. And I just felt, I felt helpless. I felt like I, cause I had a very good open door.
You guys survived, obviously.
policy with all of them. wasn't in the office anymore. wasn't whatever. And I couldn't tell them that this was the best guesswork preparing for a sale. And I could. Yeah, like we needed to retain the team. You know, it was important. And I think that's probably the thing that ate me up the most. I think that was the hardest thing for me because I'm a very honest person and upfront and honest person with my team. And I couldn't be at that time.
You had to keep it.
And I just, and then when the cell went through and seeing how it was, and there was a few layoffs because you're getting rolled into another large company. So of course we can't take everybody. and, and just, it was just really difficult. And, know, my wife was one of those ones that were laid off to you. so, you know, and I knew that ahead of time that was coming. So it was just, being in that part.
There's casualties,
was tough and I blamed the board. I blamed the new CEO at the time and I was really upset about it, but I realized that that's just a part of the process. And in order for me to understand and learn what it's like to go through an acquisition, these are the things I'm going to have to go through so I can learn. And so I'm happy and confident that I stayed curious about it.
Yes, to share. Process is happening so I can take from it or I can feel beat up by it. can choose to learn.
And that's what I did. And it took three, four months for me to really sit there and go, I could choose to learn or I could choose to really hate this. And I chose to learn from it. And it was like a big weight off my shoulders. And to this day, when I'm talking to some of employees that are ex-employees now, I kind of make sure I'm telling them that. Just understand this is part of the process.
I knew that we were scaling into something that was going to eventually sell one day. And just know that you were part of the story of that to there. So be proud of that, you know?
As a leader, as a human being over the years, have you gotten better at putting yourself in the other person's shoes? Sometimes when we're younger, I wasn't that good at that. I'm not saying I'm awesome at it, but I'm better at it than I used to be. And I'm hearing you talk, there was a lot of like, wow, if I look at it from this side, I can learn. If I look at it from this side, I'm going to be pissed off. So I got to choose. That flexibility is not always easy to do.
not easy to dig hard within. I've read a lot of self-health books. I've been doing a lot of digging in deep to get through a lot of the, I'd say trauma from all of it. It's been a tough pill to swallow, but you feel so much lighter at the end of it when you realize that you took
that we carry around.
the road that was better for you, you know? And I felt so much better about that. I feel so much better about it.
has that personal improvement journey, has that been a lifetime journey for you or is it something you're leaning in? Maybe now you have a little bit more space. Are you leaning in even harder? It all starts with self in my opinion. All starts with self.
Yeah, I'm leaning in harder now probably because the more I've learned, the more I've learned about myself and what kind of a person I am, the more that so much opens up within you, right? And so I've started really digging deep, like, you know, being into ceremony in the indigenous world and really learning exactly that, putting myself in other people's shoes, really learning a little bit more of a softer approach while trying to make sure that I'm still loving myself just as much.
You know, but where, for me, when you're running the business, your ego is a little bit bigger. You're, you're, you're just like hustling hard,
It has to be to a certain extent. You need to have enough brute force to push through the shit to get to the top of that next peak. And then there's like the fall summit. guess what's after this peak? Another peak.
And then when you're getting to this part, you're like, kind of on the other side, looking in and going, wait a minute, I don't have to be that anymore. Right. And that's, that's the hard part where you're like, okay, there's a balance of I had to be this as the founder and go, go, go. And then you're like here and you're like, wait a minute, I don't have to be that anymore, but I can still equally take what I've learned to take everything that I have learned, take all of the things inside of me and apply it in a much more positive way.
Not in saying that it was a negative way, but saying that everything I've learned in that way has helped me.
Better, better. Was it about giving yourself permission or even seeing it? Both?
It was giving myself permission. This last eight months was probably the hardest for me. It was mentally, physically, but it tested me. It tried me. did all of it. Yeah. And all I wanted to do was come out a better person. for me, there's a documentary being made about me right now. I'm off to the Philippines to speak. I'm speaking all over the world.
questioning everything.
That's very cool. Yeah. That's all.
I'm building out the TapWe platform and stuff. So good things are happening. And I would like to say it's because I've let go and I've learned to dig a little bit deeper into who I am and do things and apply it the way I want.
And we could do a whole podcast on that right there. But you said, you obviously reading, you used the word ceremony, which to me is very powerful. with indigenous, like there's ancient knowledge. We've been on this journey for a long time and I think a lot of it got forgotten about. And it feels like it's being rediscovered right now a little bit, or that's just where my brain is seeing. So talk to me a little bit about that discovery and with your indigenous background and how much is that tapping into that wisdom that's always been there?
You know, in the indigenous world, money is trauma, right? And for me, the trauma that I feel, and I'm not saying from just the exit, but from the nine years, the last nine years of everything that I've been through and done to really run this business and do it, it's all trauma one way or another. It's trauma. It's all tied to money. It's tied to VC back money. It's tied to raising. It's tied to becoming positive.
like cashflow to money in the bank, to keeping the lights on, everything. And it's really, really hard because you are carrying the whole world on your back, especially when you're an indigenous person going through that. And there's not many of you. Like I think I'm the first indigenous.
I mean, it wasn't a playbook. You could just like pull off the shelf and had it all. Yeah. No.
There was no instruction book for me to do this. But yeah, and I think for me was digging in and going back to my roots and I've talked to my mom a lot about it and mom would say, okay, well, what can you learn from this? And that's almost all she would say to me is, okay, okay, so move your eyes. And I was it's not that easy and no, and stub my feet and run out the door because I...
Is it what you learned from
We're all little kids underneath Bobby. I'll throw a tantrum right now.
But it was really about digging deep and being in ceremony with yourself to understanding that this was the path that was carved out for you. These were the cards that were laid and it's okay. you know what? You've done a lot. Like what about thinking about the positive of all the goods you've done in that nine years and thinking about what can you take that to learn from it onto your next venture of what you're gonna do. I, know, whatever I'm gonna do, you know, and it's like, take it on, take what you've learned, apply it.
and what can you do to help the next founder and underserved person feel supported? Because I don't necessarily think I had the support from my closest, we'll say investors and advisors that I needed. And I want to be that person to have that support for them because as an indigenous person. Back to Yeah, I want to be a better version.
to seeing and doing a better version. Yeah, so interesting that that that journey of self and it so easily gets, you know, read another book, take another course. Yeah, but it's all in giving yourself permission like and even the biases like, again, anything come to mind in terms of like, what you used to think versus now you can almost laugh at it because I like to look back on earlier Tyler and go, Wow, that was a real knucklehead thing that but that was what I knew at the time. And bias is everywhere in our
It's all.
So we see it, we filter that way. Anything comes to mind for you in something that even the early days that you believed was true, now you look back on it and go, wow, what a different way I can look at this now and move myself forward. Because I think leaders were riddled with them, but because we're leaders sometimes we often just get to espouse them as trues and maybe they're not always true.
I think really the number one thing is like you're not always right, know and and like it's a dog
It's just shuttered, right? What do mean? What do you mean?
But I think, yeah, you know, there was, there was, yeah, right? Like there is a time there though, where I was like, no, I'm right. You're wrong. And, and I think, you know, as leaders, like, I mean, who I am now as a leader versus four years ago, five years ago, totally different person. And something now where it's just like, you know, the more you open that door and keep it open for them, the more that person's going to shine.
Right bias.
And that's where I didn't before. would be like, you know what? That was wrong. That didn't look okay. This is wrong. Start over. One minute. Let's talk about how do you make that person feel enlightened and make that person feel why it was okay for the mistake they made, but let's encourage them to continue going to make it back. Coach. Yeah. And I didn't, I didn't, I didn't do that at first.
It's a culture, right?
I appreciate you're like, no, no. I feel you. I got a few of those bricks in my backpack as well. like, God, what a dick. I heard such a good comment to the day from a friend of mine, goes, Tyler, before you give feedback, always ask yourself, are you trying to make, are you helping to make that person a better version of them or are you just trying to make them a version of you? I was like, ooh. That's deep. Yeah, it hit me hard. Cause I'm like, now I'll catch myself about to tell someone something. I'm like, okay, how can I frame this in a way that would be relevant back to your point about it?
VVVV
What can we take away from this? you know, again, how do you create a, how do you keep a culture of questioning versus defining alive?
Yeah. think like now I'm probably the kind of person where though I ask so many questions that I get kind of annoying.
The people I know ask the most questions.
Well, right. And then I would get a little bit annoyed and I realized that I'm probably getting more annoyed with myself than they are with me. for me, it wasn't just encouraging people that questions is exactly what's going to get you to where you need to go. And if somebody is not going to make you feel safe enough that they can ask questions, then that's a problem. so I
Right. Safety fall flat. Yeah. You get half baked or you get false truce.
Exactly. Yeah. And I really encouraged all my leaders to it's okay. Like, you know, there were times where I'd be sitting around the table in our weekly one or weekly leadership meetings and some of the leaders we showed like frustration about some of the questions. so it's really about leading them to understanding to like, you know what, like questions might seem annoying to you, but they're probably more annoying to the person asking them because they feel like they're annoying you. it's
It's the cycle of abuse of a question. But it all comes back to safety. I even talk about a about in the book, I remember early in my career, I'd meet people that were super successful in my mind, but they'd ask what I thought were the silliest questions. But they weren't afraid to ask anything, but they were learning. And they'd ask and they'd ask. And then all of sudden the asking would start to become directive a little bit. And it took me a few years to go, okay, they're not asking dumb questions. They're learning and they're not scared to ever act like they don't know the answer. And I think that's a gift as a leader.
I'm right.
You know, somebody had said to me one time where they were like, you know, there's no such thing as a dumb question. And then one of the leaders were like, actually there is, they're all dumb. And it was like, wait a minute, what? And they were like, well, they're all dumb. It's just our job is to decipher through the dumbness. And I was like, okay, that's dumb.
Yeah, but I love the playing the dichotomy
Yeah, you know, and you're like, but, know, it's something that since I've been young, my mom or advisors have always said that to me, you know, there's no, there's no such thing as a bad question. And, you know, I didn't really cycle that through my leadership, like abilities and what I was doing until a little bit later on. And then once you start doing that, it's just like things open, if you can have your team.
be the best versions of themselves and then some, it's just the world's limit. Like things happen where you're like, wow, you did that, that's amazing. Like, you know, it's where you just stopping that. And it's hard because when you're in a scale up and you have so many leaders and then you have so many team members and then under that you have so many people working in the platform that are freelancers, it is really hard to trickle that down. I think that was probably my hardest leadership.
struggle was how do you lead it down, right? Like how do you lead up, lead down?
Which is such a fantastic, because going back to your investment, common all comes back to investment. You're hiring someone, you're literally investing in that person. If you're not elevating or helping them become the best version of themselves, you're actually shortchanging your investment as a business. Like just to put this on a P &L, like you're going to balance it out. So how did you, like, did you find ways that worked better? Because I don't know if we've ever all figured it out, but how did you find ways that worked better at disseminating that culture and that way of being versus other ways that didn't?
Yeah, I don't know if I've ever figured that out. You know, because a lot of it comes on the trust of the leaders, you know, and, and for me, yeah, I think it does. But I also think that everybody that I would like to say that were hired into the company that I would that I, in any company I would do moving forward is that the HR team or the recruiting team, there's, there's a reason we're bringing these people on. And for us, a lot of the people that were coming to us were because there was a story.
Trust at the bottom of the pyramid
whether they be immigrants to Canada, transitioning genders to whatever, I would like to say that everybody is coachable, you know, until they're not. And then you have to make decisions that are not fun, but you have to. But I also do think it's on the leaders, right? Like a lot of our leaders were moved up from down here and they were moved up from, I wouldn't say down here because I don't think I ever looked at it that way. I'd say let's say individual contributors moved to their way up.
And that's because they all started somewhere in the company and they saw the type of leadership that I wanted. I don't, when you're putting your trust into other leaders and then maybe quite potentially you don't know what that other leader is doing or how they're, you know, they're not really living your values. When you're in a big scale, it's so much harder to watch for that. You know, and I really struggled with that near the end. And I'm going to say my leaders were all like that because I honestly, at the end of the day, I think, like I said,
The team at Virtual Grizz was probably the best team hands down this last three years. things start slipping away the bigger you get. It's harder to watch.
I'm a man.
And as you went through those five versions, the formula kind of changes. Like there's the core beliefs and who you are and what you stood for. The more you embrace that, the more everything worked better. But the needs of an organization that has 30 people is different than one that has 130 people. And the skills are just required to manage those bacteria. I hate doing it into a pyramid, but it is that way. See one to one or one to many, and you're now influencing 10 other human beings with your way of showing up. That gets tricky to balance. See, we're as messy as F.
It is,
I mean, me too, like I can only imagine, you know, some of the like billion dollar unicorns out there, like the unicorns and you know, how they always have so much hate online, but you're like, you can only take a little bit of a grain for salt because you're like, well, wait a minute. Now that I've actually been in the swamp, I'm not saying we were a unicorn, were nowhere near that, but we were certainly at the part of where
I struggled with leading down and having everybody in the pyramid being part on the same page. I can only imagine somebody that big. And so how do you as a leader, know? Right. Like it's like, it's, it's a, yeah.
sometimes.
You hear those stories a lot because oftentimes these are success stories. get betrayed that way. And you talk to people and I've heard the joke, oh, know, South Korea on the outside, but North Korea on the inside and those kinds of jokes. But what what journey were you? Where were you in that scale to the next level? When were you no longer the right fit for that organization? And we'd love to not always take on our personal part of that. It's easy for me to you, the leader for why it didn't work out for me.
I think.
I think when I stepped into President Roland May was the perfect timing and the exact timing that was set for me. I knew it was coming for me. It was nobody's decision but mine. I I started feeling like I've taken it as far as I could go. It's time to move into something that brings me more, something that brings me more passion again.
for for knowing back to know yourself. that's like,
I started losing the passion and that's okay. And that's the one thing like, you know, that deep and dirty talk from founders who have exited is, know, I was talking to two of them the other day who have just recently exited with me here in Calgary, like all three of us from, from Skellos and all three of us pretty much say the same thing. It's that we, it was our time to exit and we were happy for that because you, you get to that point where you're just exhausted. You're, you're fatigued.
You're not, don't have the passion as much anymore. And you know, what makes it different though is if you're a founder that can accept that and say it and versus just keep going and driving your business to the ground. Right.
We've seen those stories. It's always easy to see them from the outside. Well, you're kind of literally living the same journey you just talked about about the company maybe outgrows certain leaders or uncertain. Sometimes it outgrows you. Yeah. And you can always choose to step up or you can choose to step to the side. Point being is you've made a choice.
And I thought it was better for me to step aside and say, take my legacy and go, let's go guys go. And I was excited for that. Yeah.
Go. Exactly. know. know totally. was that, was that I woke up one day and that was real or was there a lot of back to the journey of self?
One with the world.
Yeah, it was really about the journey of self, like me sitting down with my wife for months before that. Even for our wedding in December, like the prior year, I was starting to be like, okay, I'm tired. I've lost the passion because the money that was given to us, which was great, like the raising, the passion got lost amongst everybody that was involved. And I was just like,
chats literally.
Back to the trauma, as we mentioned earlier.
Right. so for me, was that was my time. was my that was that was my sign. Yeah. You know, and I'm excited.
What signs go by is whether you see them or not, Sometimes too, like they're always going by.
Yeah, well I've seen it, it like everywhere, like...
Big billboard neon flashing. Yeah, I appreciate it. So thinking about going forward, I know you're excited. We talked offline about it before we push play around the passion of your next venture. What are some of the leadership lessons or founder lessons or like curiosity, confidence? Like this is a different Bobby than nine years ago. So that's exciting because you're taking a whole new set of tools forward. What are some of the stands out? It's like, are the non-negotiables for you going forward for your next ventures?
Yeah. There's so many of them. I actually wrote a list that is kind of funny. And reason I wrote a list was because I'm obviously starting a new venture and I have a bunch of, we'll say things in the fire right now that are happening for me that are good things. But, you know, I wanted to make sure that I would have non-negotiables. And I think right now it would be the way that I would have to raise money to the way that would work better for me.
I think some of the things that I've learned is virtual gurus still could have scaled and grown on its own without such a large investment. And I that the passion would have still been there if I was running it the way I want.
That's a powerful learning because there is that take as much as you can. But I've talked to founders, they're like, I should have taken a little less, kept a bit more control. Maybe things would have like netted.
100%. Cool. 150%.
I appreciate the honesty again about that one.
Yes, and I feel like it would have, I feel like my passion wouldn't have, I wouldn't have lost my passion into what I created. You know, and I mean, I'm excited to have learned that. I'm excited to have realized when the bulb went on. Yeah, and then when the light bulb went on, I was like, all right, okay, this is what this means, you know, but.
Often only one way to learn it's hard way.
The lesson I learned was I probably could have done it the way that a lot of people are telling me it's probably would be better for you to go this way versus this way. I should have. That said, again, I'm all about learning the hard way. I think that I just applied to the next. So yeah. And so for me, think it's it's taking what you're learning and understanding that moving forward. Like, like you can take what you've learned and build your non-negotiables or your yes, I'm going to do this. I'm OK to bend here.
You made it through.
But it's okay to say no. And that's one thing that I didn't realize. It's like, hey, I'm just gonna take all the money that's coming and let things fall where they've fallen in. And it might not necessarily have been a good thing for me. So, yeah.
Well, it different stages your journey, a little more confidence, a little bit back to that confidence where it's critical. I think boundaries, you didn't say the word, I'm using it, that knowing where to say no. Yes. And it's okay to say no.
It's okay to say no. It's okay to the boundaries. It's okay. And in retrospect, actually think that me deciding in May, June that it was my time to like step aside and let somebody else run the roost. I think was because some of my boundaries were getting crossed. And I think that was where I was like, okay, you know what? Like my passions lost, boundaries are crossed. This is enough. And I'm excited for that because the old Bobby,
I that, yeah.
would have just continued down that path, which is the wrong path. And I'm excited for that, for me.
True. When those first moments showed up for you, was it a, hey, my boundaries are being crossed? Or did it show up as like pissed off, annoyed? Like, did it show up kind of messy?
I was, yeah, I'm mad.
I mean, and then it was, you know, I mean, okay, just an even normal life. I don't stay mad for long. I have a little temper tantrum for five minutes and then I'm done, right? And I'm like, okay, let's move on. So I wasn't mad for long. I just was mad at the moment of boundaries being crossed and feeling violated in certain decisions that I think that...
It takes too much energy. takes too much energy.
I said the old Bobby would have continued to let that go where the new Bobby, like the Bobby that has learned to the Bobby that has grown, the Bobby that is not afraid anymore and the Bobby's not afraid to set a boundary. Right. But I was like, wait a minute, no. And I'm not saying this is anything bad about the board or about the company or about anything. It's more about the lines of where virtual groups was going once I've lost a little bit more control of decisions as such.
and enforce them.
It wasn't necessarily a bad thing. was just a, this is no longer serving my purpose.
What I really appreciate about everything you're saying, there's so many times where you could have in this story blamed somebody else. But you've not. Not once. No. It was always, that was a boundary, I had to react to it in a certain way. Not a victim. Yeah.
Exactly. And it's about me. Not a victim. It's 100 % about me learning in that moment. And what makes this more of a successful exit for me? But what makes this more of a success? The entire Virtual Guru is the entire last nine years for me is the amount that I've learned. I'm leaving with like, holy crap, did I learn a lot from that? And it was amazing. I mean, I'm actually very thankful for that.
We could end right there and do the mic drop. Yeah, how many moments where you could have exited stage left and you didn't. And the benefit is you got to here, you survived. It's amazing, we are very resilient individuals. But sometimes in the moments, those nights and mornings can be dark.
Yeah, yeah, and they're messy, know, MAF.
I mean, yeah, told you, messy. Humans are messy. I'm so excited for you. Anything you want to share about your new venture? Because I am a marketer at heart. if there's an opportunity for you to put it out, it will. People can follow you. You have a great website. Give us some, give us some deets. Give us some deets.
Yeah, so there's something that I've learned and I think a lot of it comes out of this conversation we just had. It's a lot about your own personal truths, right? And so I started Tapwe. It'll be at tapwe.com. just building the platform now, so nothing up there yet, but it's tapwe.com. Tapwe is truth for Cree and Cree, mean, it's Cree for truth. And I'm building kind of essentially like a FinTech style platform.
that is gonna help underserved founders like me with actual truths behind running a business. know, a startup is scale up. So, you you need to raise money, are the hard truths. You need to have introductions to equity founders, here's the truth behind that, here are the founders, here are the... Yeah, like... Well, I mean, more of the resources of the dirty secrets from founder to founder, but at the same time, giving them the resources where they can get that success.
You're tell all the dirty secrets. That shouldn't be. That should be out there in world.
They need to raise equity. Here's where we're going to go. They don't have any idea how to raise equity. We're going to help them. They need introductions to advisors and mentors. There's going to be an introduction platform right in the platform. There's going to be the Tufts University, which is an AI driven, folding everything from scale start to finish, bootstrapping everything. And it's just going to be a platform of truth, SaaS kind of fintech style platform. We're looking at building potentially some search funds into it, like search fund of.
Search funds are interesting. That's a whole other topic. I find that was very interesting.
That's where we can help build that next generation of underserved founders that might not have the ability to start something themselves, right?
they've got the passion to drive. There's so many, well, the silver tsunami is real thing. There's so many businesses sitting out there right now that don't have succession plans.
And I think for this, it's more of, you know, I want to create that next generation of founders out there and see.
Again, there you are right in the And very much catering to a very similar cohort or group or community that you've been working with so far. Back to you for the need is there you said that earlier. Yeah.
Yeah, and so I mean.
And just doing resources and giving people the resources that they deserve. And it could be, for example, let's just say you got an option sheet from your board of directors, but you have no idea what this option is, what it means. You should be able to go somewhere that's giving you the true resources, but that really doesn't make sense. It's as opposed to having to go and pay for a lawyer. Because when you're new starting out, you don't have money for illegal. So I mean, it's just those little easy things.
Back to
agreements get signed and you get bought in and how you set that structure up at the get-go can really return the long run as I've been told by many founders. What you don't know will get will get you.
And then writing a book.
very fun. No easy task. They're saying you're going to run a race and then there's actually doing it. What's the plan on the book? Can you give us any details? When can we expect to read it?
Yeah.
So the premiere of essentially, we'll say a documentary that I'm going to be in, it's kind of a pilot, it's going to be in May. And so the plan was to try to get the book kind of written by then and before then.
certain dates for certain things to happen, right? You're like, okay, well, there's no point not getting it done.
So I think it'll be sometime in the summer. But the book really is almost essentially, I would say it's borderline like an autobiography really. Really about my childhood and the upbringing that brought me into the resilience that I am and who I am and why I'm so eager and why I'm a builder. And, you know, I'm pretty excited about it. There's some good chapters happening and, you know, and I'm excited for it. I mean, I've never thought people would want to buy a book of an autobiography of me, but it's like...
I get a lot of requests for it.
It's a story. And it's a lot from my own journey. It's it's an interesting experience to spend time thinking about how you think about something and going, wow, how did I, how did that come to be? How did I develop these skills that now I just kind of, that's just me and I show up, but somewhere somebody put that into the computer and family community influences along the way, mentors, moms, dads, all the people. Like, and when you put, when you force yourself to sit down and think about that, it can always can be interesting of like, huh, I did not know that that's where that came from. Congrats on that. It's a of fun.
Yeah, there's going to be things. You know, and I think the documentary is already like, we start filming like next week. Sweet. it's not really documentary. It's like a pilot, like an hour pilot of the series and the pilot. you know,
Big deal, just a pilot episode.
I'm even excited about it. you know what's awesome is they're actually like recording my parents, both sides of my mom's and then my dad and you know my family and my wife, they're coming out to her cabin. You know, it's just a story of my life and what, how I am, what got me from here to here, you know.
Super inspiring for people. Random question, what are you the most curious about right now out there in the world? It's a crazy place. What's got you personally just excited to learn about?
you know, I think I'm just more curious about how can I take what I have learned and help the others that need to learn that? Cause a lot of things I've had to learn the hard way. And I know that's a part of growth is we all have to learn the hard way. But if I could just give somebody a little bit of a step up, you know,
Maybe can smooth out the edges a little bit. If you stepped on some landmines, maybe someone could sidestep and still learn some. They're gonna learn some other hard lesson, but maybe they don't have to learn that one. Like peer advisory, being in those types of environments. For me as a leader, it's been key over the years. People that have been there, go, hey, I see what you're doing. Curious, have you thought about this? I'm like, I have not. No, those are hugely gone, because what you don't know can get you for sure. Well, congratulations. I'm so proud of you. I'm so happy to know you.
Yeah, I'm pretty excited for
I listened to our episode this morning and it was so, it was great. We just sounded so young and cute listening to us talk. It was like six years ago. feel like so much has happened in the world we live in the last six years, but congratulations on your journey. think it's just fantastic.
As always, it's amazing because every time we chat, can have conversations for hours. I appreciate it.
Insistity goes a way. Bobby, thank you so much for coming on and congratulations and all the best on your journey.
Thank you.