The School of Greatness - 324 Good Hustle vs. Bad Hustle & Building a Billion Dollar Brand with Ryan Holmes

Episode Date: May 4, 2016

"Live is self-serve." - Ryan Holmes If you enjoyed this episode, check out show notes, video, and more at http://lewishowes.com/324

This is episode number 324 with CEO of Hootsuite, Ryan Holmes. Welcome to the School of Greatness. My name is Lewis Howes, former pro athlete turned lifestyle entrepreneur. And each week we bring you an inspiring person or message to help you discover how to unlock your inner greatness. Thanks for spending some time with me today. Now let the class begin. Welcome everyone to a special edition of the School of Greatness podcast.

I am so pumped to bring on my good friend, Ryan Holmes. Now for those that don't know who Ryan is, he is the founder and CEO of Hootsuite. He started the company in 2008 and has helped grow it into one of the world's most widely used social relationship platforms with 10 million plus users, including 800 of the Fortune 1000 companies. I met Ryan briefly after he launched Hootsuite

and it's been incredible to see where he's taken his company from with just a couple hundred thousand subscribers to now over 10 million and taking his company from just a few hundred thousand dollars in revenue to evaluated over a billion dollars. And I've been up to the headquarters a couple of times. I've spent a lot of quality time with Ryan over the last seven, eight years now. And it's been an amazing journey to see the trajectory of where the company has gone and also what Ryan has learned. Because I think you learn so much about yourself, about other people, about building a business when you take it from 10 to 15 employees to almost a thousand and over a billion in valuations. Some great lessons you're going to learn from today is the difference between good hustle

and bad hustle. And I think this is really important. Also, expert tips in interviewing and hiring people as he's done a lot of this on a high level. How to build a team that does all the stuff you want them to do. What Ryan learned about from his near-death paragliding accident, and this was an incredible story he shares, the massive impact of millennials in the workforce, and so much more. We had a great time doing this up at the Hootsuite headquarters when I went up there to Vancouver

recently, and just one of the most genuine, loving, incredible human beings that I know. So without further ado, let me introduce you to the one, the only, Ryan Holmes. Welcome, everyone, to the School of Greatness podcast. My name is Lewis Howes. I'm with the one and only Ryan Holmes in the house. Good to see you, man. Good to see you, brother. Thanks for allowing me to come in your headquarters. Our Hoot Nest. Hoot Nest. Hoot Nest. I love it, man. This to see you, brother. Thanks for allowing me to come in your headquarters. Our Hoot Nest.

Hoot Nest. Hoot Nest. I love it, man. This is the headquarters of Hoot Suite. I'm usually in my greatness studio, but we're doing an event this weekend, and so I'm up in Vancouver, and I wanted to get the opportunity to interview you. I actually wanted to interview you two years ago when we were driving up to Whistler together for snowboarding training.

Right. I remember that. This is the early days of School of Greatness podcast. Right. Right. So I'm glad that I didn't because I have a much bigger audience now and I'm a better interviewer, I think, hopefully. So I'm excited to dive in and so much has happened since then.

And I'm going to ask some personal questions to get started. So this is going to be a non-traditional business podcast. I'm curious, for my own curiosity, because I don't think I've asked you a lot of these questions, so this is more for me. We've known each other for, what, six or seven years now? Yeah, it's actually like early days, South by Southwest. Hootsuite. We met in New York.

We met in Amy. We met on Runyon Canyon. Runyon Canyon Run in L.A. And you had 200,000 users on Hootsuite at the time. I remember this. With like 10 people on the team. And now you've got, what, close to 1,000 people? Yeah, we're getting there.

We're just about 1,000. Getting there? Okay. I'm curious, what was your biggest dream growing up? My biggest dream. So in grade five, I had a teacher who asked us to write a fan letter to a hero, somebody we wanted to be when we grew up. And I was big into computers at that time, video games. There was a video game

called Ultima, written by Richard Garriott. And I wrote him a fan letter about how I wanted to make computer games when I grew up. And I didn't hear back from him. See, he still owe me a letter back, Richard. I know you're out there. We've been introduced since, but I think he went dark. Anyway, I'm going to track him down and get that fan letter back. But it was funny because I went through from grade five. I did a whole bunch of different businesses all the way until I was back in my 30s when I started a software company and ultimately ended up doing software, which was very close to what grade five me wanted to do. Really? That was your dream?

Well, I wanted to make video games, right? And so, uh, you know, I I'm in computers. I love, you know, we did like there's coding and all this other stuff, but I did so many other things to get back to what grade grade five me knew I wanted to do. What was the video game that influenced you the most? I love the ultimate series. It was kind of like dungeons and dragons Dragons video game. You walk around and you get gold and you find treasures and all this other stuff. Like Zelda? I'm dating myself here, but Ultima 2, 3, 4, 5, it was a series. And then they made Ultima Online. I kind of stopped at a certain point there.

But yeah, it was a pretty big franchise. And who was the most influential person in your life growing up? Oh, man, if you don't say your parents here, I mean, whether it's good or bad, your parents are always a massive, massive influence on you growing up. My parents, I think if I don't start with that, parents, obviously great teachers along the way. High school, I had a fantastic teacher that really created an amazing program for outdoor education, Barry Reed. He was a fantastic teacher that I think through high school, it was in grade 11, this program was happening. He had to keep a clean nose until you got to there, not get into trouble. He

probably kept me unknowns to him leading up to that program so I could qualify. And he was a big influence. Okay. What was the biggest lesson that he taught you growing up that you still remember today? Well, I mean, I can't nail one specific lesson that I learned. I mean, that program was very holistic. I learned, I mean, that program was very holistic. We got into things like geography, looking at glacial formation. We did native studies.

We did basket weaving. We did all this. So super holistic outdoor leadership. And I think outdoor leadership probably, it's a great thing to learn because when you're in a small group, we were doing telemark skiing, backcountry skiing, things like that. You know, there's potential life and death. You have a group of people that have a collective outcome, getting to the top of the hill on their skis.

Sure. And then just thinking about what's the best, smartest way to do that. And some of that early stuff at a young age, you're getting an opportunity to lead a little group and to take turns being a leader of an outdoor class in a situation like that. That's a pretty important and valuable thing to learn. Now, is it true you lived on a hippie foundation, like isolated from the world kind of thing at some point? So my parents were unconventional.

They're both teachers in the... I mean to knock hippie people into associating that with hippie. I don't take that. I don't take, I take hippie as a compliment in a lot of ways. But you had an unconventional life. I don't have an unconventional upbringing yet. My parents were teachers in the 70s. They decided to leave teaching.

They bought a hobby farm. And I grew up, it was off of the grid, so no electricity. I grew up with goats and chickens and honeybees. For how long? Ages? What? My, like, till high school, till I went away to university, more or less. I had kerosene lamps. I had a well. University is high school in Canada, right? High school, no, high school is high school.

University is university. So until high school, you were living with... Actually, no, through high school. Yeah, yeah. So they got a little less into the farming as we grew up and they were taking us to school and stuff like that. But I lived and grew up on this property and it was a beautiful little farm to grow up on. And did you have, were there other kids in your family? Or was it just you? Yeah, I had a younger brother. Okay. Yeah, yeah. So it was he and I, and we were out in the middle of nowhere.

Wow. Yeah, it was a really interesting update. What was it like, you know, being around in the city life after being in the middle of nowhere for your whole life? You know, it's funny. When I was growing up, elementary school, you know, younger in high school, the pressures to be normal are huge. And I always wanted to, when I was younger, I wanted to live in a cul-de-sac like all my friends. I wanted to have a skateboard.

I lived on a dirt road. You can't skateboard on a dirt road, right? Right, right. I just wanted to be a normal, quote, quote, kid like all my other friends. And then in retrospect, you look at some of these experiences that you have in life that are the funny, weird experiences. Maybe you hate them at the time, and then they end up being really formative. Yeah, yeah, okay.

What would you say was your superpower that you gained from that experience that no other kids had? the kids had? Um, I think that, that, um, in being a little bit of a, uh, you know, the, the, the funny weird kid that lived like on the Hill or in the middle of nowhere, um, you know, I got comfortable with being different and, um, and maybe that is one of the things, like, I, I don't feel, uh, a huge need to conform on stuff. And I just kind of felt like initially I hated it and then eventually I was like, okay, well, I'm different and I just started dealing with it. And that maybe started to become a way that I self-identified.

Do you feel like you've embraced that in business as well? Yeah, I think so. I mean, I've also, you know, at periods where I've been hustling on my business, you know, I've done a number of businesses. I did a paintball company. I did a restaurant. I did an agency. When I was doing the agency, I was building software products. You know, I spent a lot of time coding and, like, being isolated and just, like, being focused on building something and creating something.

I get a lot of passion and enjoyment out of building and creating things. And, you know, I guess sometimes, like, just being able to, you know, have the discipline to sit there and just, like, get immersed in something kind of, I think, maybe comes out of that comes out of that solitude that I had as a kid and just being able to work on my own sometimes when I need to. I love it. What would you say was the biggest insecurity you had growing up that took the longest to overcome for you?

You know, I think it probably gets back to that being different thing, right? Like, you know, when your kids, kids are, can be vicious, they can be really, uh, you know, hard on other kids. Um, and, uh, and, and you kind of just want to conform. You want to be normal like all the other kids. And, and, uh, um, that can be a challenge. And so, you know, it took a long time to realize that that's a superpower and get comfort around that. And then also probably on the other hand, like, as I was doing a lot of these things, you know, like getting deep into computers, spending a lot of time there, you know, I probably didn't spend as much time, like, just socializing as other kids were doing.

And so maybe I needed to spend more time on that. In university, I spent more time on that than other stuff. It's kind of ironic that you were so isolated for so long, and now you've got one of the largest social companies in the world. We're social, yes, absolutely. Millions of users and fans and followers. It is ironic, yeah, you're right. You were the most isolated kid probably in Canada, like in the top 1% of isolated kids

to the most social essentially, right? Right, yeah. Interesting. Why do you think you were put here? Well, you know, I don't know that there's any grand plan to why I was put here versus anybody else, but why I personally am passionate about is, at this point, creating legacy. I've been blessed with creating a great personal outcome with the business and the businesses I've done. I'm really passionate about, I talk about building a technology

ecosystem, creating opportunity for other people, both people within Hootsuite. I love that what we're building here, I think the work that we're doing for our customers is amazing. I'm passionate about seeing a great outcome for everybody that's involved in the company. And then I'm passionate about an ecosystem forming around this. We're in Vancouver. I would love to see a legacy that gets created out of this business, the alumni of this business

going out into the community, into the economy, creating other startups. And then I'm also so passionate about technology. I think we are at a very interesting time in humanity right now. There's a lot of digital transformation that's happening, a huge shift in the way we do business and the way we are as a society.

And so I'm so excited to be a part of that and looking ahead into the future in terms of witnessing it. That's cool. Now, how did Hootsuite come about in the first place? And was it an accident or was it intentional? So, you know, I think almost any startup founder that says that they planned out their startup to be where it is five, ten years later is lying.

If they say that they were, yeah, I knew all this was going to happen. I mean, there's some e-mails floating around that, you know, Zuckerberg was talking about how he was working on this fun little project called Facebook, wasn't really going to amount to anything, you know. Right, right. There's all that kind of stuff that happens out there. And so, you know, we saw an opportunity and a need. I had an agency.

We had a group working on social media for our clients. You had about 15, 20 people? We were about 30 people, actually 21 people at that time. And we started building a tool to scratch our itch. And we put it out into the wild, into the Internet, and people started using it. We started to see good adoption on it. And all of a sudden, friends were telling friends, and we were telling friends, and it was growing very virally. You know, flash forward a few years, we had a couple million people after, I think, a little over a year, and it just started ramping, ramping.

And so, you know, we couldn't have predicted necessarily where it was going to be today. But as you build, you know, Twitter, Facebook, they're relevant. They're here to stay. They're not about, you know, sharing what's for breakfast. And then seeing new challengers, you know, Instagram, Snapchat come onto the market. Pinterest. Yes, absolutely. These are absolutely transforming how consumers are relating to big brands.

They're transforming how we're receiving content and entertainment information. And this huge transformation that's happening has really unveiled to us this really big opportunity. And we're very blessed to be sitting at the middle of this to help our customers with this whole customer life cycle that is relevant to social. Now, how did you scale? Because you're almost close to 900-something employees, right? How did you scale from probably the biggest company it sounds like was 30 before then? I don't think the paintball company was probably bigger than 30, right?

So your biggest company was ever had was 30, now it's at 900. Within a few years, how do you learn that new skill? As a leader, as a CEO. Yeah, how did you learn how to do that? So the great thing about running a small business is everything, the buck stops at you. So you're accountable for absolutely everything. I think small business owners often learn to become good generalists. So you learn to become the marketer, the salesperson, the product person,

the ops person, the copywriter, the janitor. Customer support. Customer support. You're everything. And that's like a mini business school, right? So that's your MBA. And so I think about all the businesses leading up to Hootsuite, they were all like mini MBAs. My restaurant, mini MBA. My payball company, mini MBA. There's I think about all the businesses leading up to Hootsuite. They were all like mini MBAs. My restaurant, mini MBA. My payball company, mini MBA. There's a lot on, on, on.

And then what you do learn, I think, through that process is you learn what you gravitate towards and what you love doing and what you're good at. Usually those three things are the same thing. You know, like what you love and what you're good at is usually the same thing very often. Sometimes we try to stretch ourselves to get good and to love things we don't love and we aren't good at. And sometimes that works. Sometimes it doesn't. I think most often it's people love doing something and that's what they end up doing.

And what you learn also as you scale and as you have more resources is to delegate the stuff you don't like doing. Because if you're not aligned with passion to what you're doing, you're not going to get enthused getting out of bed. And so find people that love doing what you're doing, you're not going to get enthused getting out of bed. And so find people that love doing what you're doing. And the great thing about people is that for every job that you hate, there's somebody out there that loves doing that job, which is pretty cool, right? Like I've got a CFO. He loves numbers. He sits and looks at Excels every day.

I can look at an Excel. I can read a balance sheet, an income statement, a cap table. But if I had to do that every day, I'd go crazy. And he loves doing it. And what do you know? It's so great. So surround yourself with people that love doing what you don't love doing and then scale yourself. And so, yeah, the process of scaling to this company, it's been interesting.

It's been an evolution. I've learned so much along the way. And at each stage, I'm a lifelong learner. So I love the different evolutions. I feel like we've recently gone through a bit of an evolution. You know, I think about the rule of 10. People can usually manage about 10 people. So you hit these kind of ceilings of management at 10 reports, at 100 reports.

So you've got 10 reports, and they're managing 10 people. That's 100. And then when you get to 10 people managing 10 people managing 10 people, that's 1,000, right? So we just kind of hit this next level. We did a lot of reorg around that. We brought in a bunch of leadership that are really going to help. And I'm super excited about the foundation of the company and the leadership I've got now. And now can I scale this to 10,000? I think we really hit an interesting new level in the company. I'm really excited about it right now. That's cool. That's cool. So you're hiring people, a lot of people, really fast over the last few years. And you

have to ask a lot of questions. You have to interview a lot of people. If you could only ask one question for every person you interview, and that question would decide whether they come on for you, they would come on board board or they would not, based on their answer, what would that one question be, the most important one for you to know the answer to? That's a real tough question. I alluded to not giving me these questions beforehand, just for the record.

Off the top of your head. Off the top of my head, I think the one thing that I would ask somebody about is what is the hardest thing you've done and why are you proud of that? I think that people that go through some adversity in life, go through a super challenging project, a challenge in a personal situation, adversity in sports and life or whatever it is, I think that's often really formative.

And then how they learn from it and what they learn from it, what they took from that that they carry through the rest of their life can be really important and talk a lot about the person. I like that a lot. So what would be the answer to that for you? I think that the – yeah, that's a good question. You just throw it right back at me, Lewis. Am I interviewing for the School of Greatness right now? Can I get a job? You know, I think that I've had a number of different things in my life. I'm trying to think

of the most adverse moment. You know, I've had some near-death situations. I think you learn a lot about life in those situations. But those are really small flashes. Like I crashed a paraglider a few years ago. Really? Yeah. While working with Hootsuite? Yeah, but don't tell me.

This isn't going on the Internet, is it, Lewis? Yeah. While working with Hootsuite? Yeah, but don't tell me. This isn't going on the Internet, is it, Lewis? Exactly. So, yeah, no, I crashed a paraglider. I wouldn't call that. But the interesting thing with that is I had a few minutes knowing it was going down. Like I was going down into a forest. A few minutes. Yeah.

I was like, I missed my landing zone by a lot. I wasn't paying attention. I was flying over a forest, and all of a sudden I was too low. And so I knew I wasn't going to make my landing zone, and I was just flying over a forest and going down, down, slowly. And so that was a really pretty scary situation. But I had time to kind of just think about stuff and dread stuff and think about, oh, man, this could be bad.

I got a lot of stuff I need to do in life ahead of me. I don't want to break my legs. I don't want to break my back or be in a wheelchair or something worse, break my neck. What happened in that moment? I froze up. You froze up when you landed? No, no. I froze up in the air.

I got so pumped. My forearms, my muscles were frozen in fear. The adrenaline. The adrenaline kicked in over time. Wow. And so I spotted this little clearing, and I was like, okay, I'm going to head for that clearing. And I headed for the clearing, and I was trying to aim for it, and then I flew right over the clearing because I couldn't control my muscles. Oh, my gosh.

I was just completely, I didn't have fine motor controls. I was just, like, pumped, like, rigid. And so I, out of the back end of the clearing, there was a little road, and I started kind of going up the road. But if you've seen a paraglider, paragliders are about two lanes wide, and I was going up a single- road, and back and forth and back and forth, trying to miss trees on either side. No way.

And I caught a tree, and it reeled into the forest. I careened down through branches, snap, snap, snap, snap, snap, snap, and I was hoping it was going to catch and snag on a branch. It didn't. I landed on the ground, full force, my feet, I rolled over. It kind of got slowed down by the branches, and then I started patting myself down to see if there was a branch going through me. Oh, my gosh. Because there was so much adrenaline, you probably couldn't feel it.

Yeah, I thought, like, immediately I thought it was that thing. Like, I had a branch sticking through my chest, and I didn't even know it. Oh, my gosh. But I didn't. And I was like, that's amazing. I started wiggling my toes, wiggling my hands. I got up. My phone screensaver to this day is a picture of me when I landed on my paraglider.

Oh, my gosh. And I pulled up my lines, and I took a photo of it. Let me show this on the video. Yeah. So I took a snap of that to catch a picture of my happy face in that moment. And I can send you a snap of that, so you got it for later. But anyways, I came out of that with actually not even a single scratch.

What? How fast were you going? You know, probably 20, 30K and then kind of slowed down. Miles per hour. That's going to be about 15, something like that. 15, gotcha. Yeah, yeah, yeah.

Still. Not super fast, but it was high. I mean, it was tree height, then it's straight down. So I came out of it okay, carried all my pack on my wing, carried it out of the forest, and then I went and relaxed and lied down in the sun and just thought about life. What opened up for you in that moment? I think it was really about the small amount of time that we have here to put a dent in the universe and just living every moment. You know, like taking advantage and making sure that what you do in the short amount of time you have,

like that could have been it. And thankfully it wasn't. But, you know, what am I going to do with the short amount of time I have, like that could have been it. And thankfully it wasn't, but you know, what am I going to do with the short amount of time I have here? How am I going to, you know, make the best use of it and, and, and then cherish that. And so that's been, you know, it's been something, as I said, it's on my screensaver to this day to, to kind of keep that as a little reminder. And that's one of the, one of the moments. What's the other moment, most adverse moment? Most adverse moment. That's a, that, one of the moments. What's the other moment? Most adverse

moment. Most adverse moment. That's a, that's a, that's a, a moment of adversity in a flash. Yeah. Yeah. Yeah. Longer ones, longer ones. You know, I think, um, was there ever a moment Hootsuite was not going to last or? There's been, there's been challenges with Hootsuite. I think one of the ones that was like racking for me, actually, we've gone through challenges. I, I feel like we've been really blessed and and um i think one of the bigger moments you know of adversity was dropping out of university also really uh yeah that was that was a really tough challenge uh i think societally so many of us are wired for you know you finish high school then you go to university you do your degree and then

you go and do your job and then and and that's what we're kind of wired from a very early age. And I had a lot of stomach acid on that. And it took a long time to kind of come to terms with that and then break it to my parents, who were honestly so amazing about it. They're like, oh, okay, well, that's great. What are you going to go do? And didn't give me a single moment of stress. I beat myself up over it a lot more than anybody else did. But that was also, it caused a lot of, it was a moment of adversity. And also,

I think it was very formative, getting back to hard times in your life and how that changes your life. Why did I do it? My motivations for doing it, the program I was in, I always wanted to be an entrepreneur. And the program I was in was teaching me to be an employee. And I purposely sabotaged myself so that I wouldn't be a suitable, I wouldn't be a good employee. And it sounds silly, but I made that kind of decision. I'm like, hey, I don't want to do that. That's not going to be what I want to do. I want to go and forge my own path.

And so I'm going to make this decision. And it was a good one in retrospect. What's the vision for Hootsuite moving forward? What's your vision for it? We've got a big vision. I think that with what is happening right now in society, there are the biggest cohort of employees in the workforce are millennials as of 2012. So that means there are more millennials than any other, more digital natives than any other group in the workforce.

That changes how the inner workings of companies and also the external workings of companies, how companies communicate with their customers. And we think that there is big opportunity in dealing with both the internal and external communications with customers. Most millennials have never seen a phone booth. Right. Unless you're in London.

Do you have a home phone? No, all cell phone. Right. So that's something that's completely changed. And by the way, I poll audiences with this. There's a bit of an age skewing. And then I ask the people that do have, you know, it's usually maybe max 5%, 10%. And I talk to the 5% and 10%. And I say, well, how many of you think every month when you get the bill that you should get rid of it? And the biggest reason that people keep it is because it's hooked up to their alarm in their house, right? And so if you think about that, I always find that interesting because so many people that are non-millennials or non-digital natives

grew up with the landline in the house, and a lot of them still have it. But in the next few years, as this millennial cohort gets bigger and bigger, it changes behaviors. Are they going to call a 1-800 number to talk to your company? Absolutely not. They're going to go to social media. They're going to text. They're going to tweet. They're going to text.

And how quickly do they expect a response? They expect a response in under 60 minutes, right? And sooner than that for a lot of them, right? And so that's just one example of how businesses are going to need to change to evolve. And so it's going to be customer service. It's going to be marketing, how they're communicating their brand and creating awareness in the market, how they're selling to people. And we sit at the middle of all this.

And so that's a really exciting piece for me, as well as how brands are sharing what they're doing with their workforce. And so we sit at the middle of a trillion-dollar opportunity, and we just want to continue to grow our business there. I love it. Now, you're constantly pulled in many directions. We were just hanging out for a couple hours, and you're on the phone, left and right, meetings, employees, vision, investors, all these different things happening. How important is your personal health for the success of a company, and what's your routine with health and working out? Yeah, I talk about this a lot. I write about it.

I think that having a balanced life is so critical. That includes, you know, there's a great post that I saw, and I posted it out a while ago, shared. It had good hustle and bad hustle, and I think there is such a thing as bad hustle and negative hustle. It's like no sleep. No sleep. Yeah. I stayed up and I worked 24 hours straight and it's like, that's bad hustle. Congratulations. You're going to give yourself a heart attack and die. Don't do that. That's not healthy hustle.

What's good hustle? Those are the things I want to focus on. What are those things? Good hustle, it's working smarter, not harder. It's like getting exercise and balance in your life. Attacking things with passion, sure. This piece, I'll share it with you. It's awesome, and it resonates so well with a lot of people. As I said, balance in health, hugely important to me. I had a back injury a few years ago. That is another, speaking of formative things in my life and adversity,

that was actually, I'm surprised I didn't immediately glom onto that. But that was a huge moment of adversity, one of my darkest years. I was using a crutch and a cane. Yeah, it was really bad. That's why you got into yoga, I think, right? Yeah, that's a cane. No way. Yeah, it was really bad. That's why you got into yoga, I think, right? Yeah, that's why I got into yoga. Yeah, absolutely. And out of that balance and not sitting down at your desk all day, I created my stand-up desk company because I wanted to give that out to people and put that back to the world to

give people a little balance in sitting down and standing up. I bought one of those. They're great, by the way. Thanks. My video editor used it. What's the site? I bought one of those. They're great, by the way. Thanks. My video editor used it. What's the link for that? It's oristand, O-R-I, like origami, stand.co. Okay, cool. Awesome.

So routine then for- So yeah, I do probably, I exercise probably three, four, sometimes five days a week. I try to get a little something in. We've got a gym at the office. I'll take off at lunch and I'll go work out a couple days a week. I'll go for a run. I'm trying to get faster running right now. Cycling season's on. In the winter, I backcountry ski. I just try to get a little bit of something everywhere and enjoy myself while I do it. Find sports that I like and get exercise in when I can and then lots of yoga. I really enjoy that.

I love that. Who do you learn from the most in your life right now? Other than Lewis Howes. I talk often about the Mr. Miyagi, the mentorship. A lot of people ask me about who I learned from, who's been my biggest mentor in life. And I don't necessarily believe in the idea of one mentor that solves it all for you. When I was in B school, one of the big things was go find a mentor. And I appreciate that in context. I've had a number of amazing teachers that I've learned from in life. You know, I mentioned my parents. I mentioned Barry Reed.

And there's been others along the way that I've learned a ton from. Is there one person right now in your life, whether it be here at Hootsuite, your personal relationships that you learned so much from just by that relationship? Yeah, you know, as I say, I think it evolves over time. And right now, yeah, there are people in my life that I'm learning a lot from. You know, a couple of my investors, I've learned a ton from them. They've been super fantastic. I've met with, you know, when I interview candidates, I learn a lot from them.

I learn about how they think they should be doing the job when they come in. One of the most important things for them. And I'm looking, you know, I've been looking for a couple of senior people and I've learned a lot from all the people that I've talked with. And I try to make it bidirectionally a learning experience when I meet with somebody and hopefully we can both gain knowledge and experience out of it. But yeah, there are people I am learning from all the time, Lewis. What's something you're most proud of that people don't know about? Oh, man. I'm an oversharer, Lewis. Probably everybody. I'm pretty transparent on this stuff. I'm super proud of TMBT. This is a foundation that I created. And the goal of

TMBT is to help accelerate young entrepreneurs. You know, I'm a young entrepreneur. I started my paintball company when I was in high school. And, you know, it took me from being a promising young entrepreneur when I was 16 to being 35 and doing Hootsuite and then the rocket ship that ensued there. And what my thesis is, is that there are in so many entrepreneurial circles that I go and talk at, the CEOs that are there, I'm a member of YPO, I poll people in YPO and ask them how many people in here started your business in high school? It's really interesting. It's about 25% from my kind of straw polls. I find that so many entrepreneurs have early entrepreneurial talent. And the interesting thing is those 25% later on go on to be the CEOs of multimillion-dollar companies.

How can we – I think there's a really strong value prop societally to try to accelerate entrepreneurs at an earlier stage more quickly. If we can do that, I believe that it's going to ultimately increase GDP. It's going to create more value, more jobs in the economy. And so that's my little piece is to find and try to help accelerate a small group of young entrepreneurs. And that's a program that I'm really passionate about. If you had all these kids in one stadium that were part of this program, and you got up in front of there and you could give them one message, one piece of advice for, they're all 18, 20,

and they say, what's your one piece of advice for us to have a successful business and thrive for the rest of our lives as entrepreneurs? What would that piece of advice be? I mean, I talk about the good hustle, the bad hustle. I'm huge into hustle. Entrepreneurs are self-propelled. It all comes down to you. You have to own accountability. It is not about the, you know, entrepreneurs need to be insane. You have to be insane in a good and bad way. You are crushing through walls every day. You've got all of these things that are stacked against you that are going to tell you that what you are doing you can't do, and you need to just have your own way of thinking about things.

You need to basically build your mental game has got to be as strong as your physical game. You need endurance on both fronts, but you've got to be able to, um, persuasively talk about what you're going to do to get people aligned around a vision to, um, you know, move the ball ahead and to, and to, and to work through bureaucracy and bureaucracy is the enemy of entrepreneurship. And so, uh, you, you have to be able to do that. And, and that, that just takes hustle. It takes perseverance. It takes, It takes self-discipline and motivation. And you've got to find that yourself.

I love it. Okay. I have a rapid-fire question section. This is the first time I've ever done a rapid-fire thing. I'm honored to be your first guinea pig. Well, one, because we only have a few minutes left before the crowd comes in. And then I have a few finishing questions after that, which will be more thoughtful or longer answers, I should say. So the rapid fire.

Okay. And we already talked about this a little bit, but overall, what are you most proud of in your life? Well, you know, at this point, I'm really proud of Hootsuite. I'm proud of everything we've done. That, to me, I think is probably it's been my baby. That, to me, I think is probably it's been my baby. And until I have some babies, which is, you know, coming up in the next little while, I'm really excited about having kids at some point.

I'm not putting out a date or anything. It's not happening. There's no buns in the oven right now, but I'm excited about doing that in the future. For now, this is my baby, and, yeah, I'm really proud of what we've done. If you could have anything you want after Hootsuite, whenever Hootsuite's, you're gone from Hootsuite or many, many years from now, what would be the next dream if you could say, this is what I want afterwards? Anything at all. Well, I mentioned legacy.

So I just want to be able to create a legacy in an environment that helps other people achieve their dreams. And so I think that technology is the way that I would do that, and so I'm excited about creating and helping create a technology ecosystem in my backyard, Vancouver, Canada in general. Cool. If I had all the money in the world and handed it to you and said, you get to solve one challenge in the world with this money,

what would you solve and why? Oh, man. You know, that is a great question. There's lots of challenges, obviously. Pick your battle, right? What speaks to you? Well, I mean, so many things speak to me. I think that I get really excited about, I know there are a lot of problems in the world.

I believe that in order for us to solve these problems, we fall forward and we solve them through technology. Like there's problems with the environment. I have to be optimistic that we're going to solve that, and I believe that we solve it through technology. Like are we going to convert to a hydrogen electricity economy? Are we going to all go Tesla? I think that technology is solving that, and that's going to help with our greenhouse emissions. Beef, I have a steak every so often, but beef is apparently a big contributor, one of the biggest contributors to greenhouse gases. But there are people that are creating lab-grown meat, which is really interesting to me. And so that solves the problem. I think that I kind of would be the kind of guy that would sprinkle it around in a lot

of different areas, the environment. Sure. I think technology and I think food is also an interesting area to solve for. Cool. I'm not rapid-firing very well here, am I? It's all good. Your favorite business leader, what's the one person you would say right now? You know, I...

Besides yourself. Yes, modesty forbids, but I'm a huge fan of Richard Branson. I think he's built such an endearing brand. He's got personality, and he's just, you know, I think so many people, if they were going to choose one business leader that they would spend some time on a beach with, that would be the guy. And I just really respect what he's done with his brand. The hobby you love the most, the thing that brings you the most joy? I think it's a good question. I think backcountry skiing I love. Running I just love. It's simple.

You just need a pair of shoes. Yoga is great. Obviously, I get my endorphins from sports, and that's the time when I tune out. I can't think about what's going on in business. So all these things, I find that's my way that I relax. If you were forced to put a word or a saying tattooed on your forehead that you would see if you looked in a mirror, it's a reverse wording, but it was stamped on your forehead, what would you put on your forehead? It would have to say, free hugs.

Free hugs. Yeah, I mean, you can't be mad at a guy with free hugs on his forehead. Okay, I like it. Well, what if it was one that people couldn't read, only you read in a mirror? Only I read in a mirror. A message that you saw when you looked in the mirror, so it was reversed. All right, all right.

Not to the world, but just to you. All right. As a reminder. Maybe it's along the lines of seize the day, but life is self-serve and go get it. Maybe it's life is self-serve. Cool, I like that. If you could be anyone for a day, who would you be?

Right. Oh, wow. If I could be anybody for a day, I would be... There's so many great opportunities there. I think I'd be lying if I said I wouldn't want to be a woman for a day. How crazy would that be to just switch genders and check it out for a day? I think that would be really interesting.

Look, I could say I'd want to be Barack Obama for the day and see what it's like to be on the big desk, but I think that's a really interesting experiment just to see what it's like to be another gender for a day. Which woman? Which woman? Okay. I'll go Hillary Clinton for the day.

Okay. You can put it like that. Okay. We're in the last few questions. All right. Okay. Before we ask the last few questions, where can we connect with you online? Where should we follow you?

What are you most proud of? Where are you hanging out with the most? I know Snapchat, you're still picking it up, but where should we follow you? Yeah, I play around with Snapchat. I'm at Invoker, I-N-V-O-K-E-R, pretty much everywhere. Twitter, Facebook, I'm the Ryan Holmes or the official Ryan Holmes on Facebook. I've got a page there. Nice.

And that's where you can – Where do you hang the most? I flip between Twitter and Facebook quite a bit. Instagram's fun. I share some posts on Insta, of course. So make sure to tweet at Invoker and let Ryan know what you appreciated most about this interview and this episode. So tweet him, and maybe he'll get back to you, hopefully.

Last few questions. What are you most grateful for currently in your life? I am, you know, I've got an amazing partner. She is wonderful, and I'm very grateful for having her in my life. I am also just grateful for my team here at the business and everything that they do at Hootsuite. They are hustling and putting it on the line every day and doing really big things. And their effort is just massive. So I'm super grateful for them.

That's cool. Okay. Many, many, many years from now. It's the final day. Okay. You've created your legacy. Lying in my deathbed. You've done everything you wanted to do.

And peaceful. Everyone's there. It's a joyful moment. Okay. But for whatever reason, everything you've created has been wanted to do. And peaceful. Everyone's there. It's a joyful moment. Okay. But for whatever reason, everything you've created has been erased from time. Okay. So you've written many books by now, but they're gone. Okay.

Every article, gone. Okay. Business, gone. All right. And your great, great, great whatever grand saying comes up to you and says, we have a piece of paper, and you get to write down three truths, the three things that you needed to be true from all your experiences, since there a piece of paper and you get to write down three truths, the three things that you needed to be true from all your experiences since there's nothing

else to remember you by in physical form. And this will be essentially what we remember and use as our lessons moving forward. So what are those three truths? Wow. Without prepping you, without prepping you, obviously. Wow, this is abstract. Without prepping you, obviously. I would say, so getting back to life is what you make of it, that's a theme for me, right?

So life is self-serve. It's all about the good hustle, right? Like you're putting it out there. Everybody has their limitations in life, and you've got to get past those things. And so that would be obviously a big theme for me. That's one. Okay, that's one. I'm bundling those two things in there. I think that the love of family and friends is obviously,

I think that I believe that we're heading into a really interesting era in humanity right now where we're talking about a lot of jobs getting displaced. I'm hopeful that we can do that with abundance and that people coming out of this have the opportunity to choose whatever they want to do in life. And I think that that's going to get back to recreation. I think it's going to get back to, you know, hopefully it's robots feeding us grapes, you know, that type of thing,

you know, utopia. And I think if that is the paradigm that happens and you think about what is important, I think that what is important is the love of your friends and family and people around you. So I think we may have a renaissance of that, you know, where we're less focused on the day-to-day grind, making ends meet and other things, and we get to focus on that.

And then also it's experiences, like experience things in life, go and see things, go and visit things, go and do things. things, go and visit things, go and do things. I think that that's just the part of this interesting life that we have, the mortality that we have for now. Maybe that changes in the future, but I get excited about experiencing everything we can on this planet, and then at some point in the future, maybe we get to go beyond. Right. That's cool. Those are great three truths. Before I ask the final question, Ryan, I want to acknowledge you for a moment. Okay.

For your incredible friendship. I don't think people know how intelligent you are and brilliant you are as a business guy, but as a human being, I don't know too many people who are as genuine and loving and caring as you are, so I want to acknowledge you for your caring and your consistently showing up for people.

I think you show up for your friends, but also your employees, your team, and everyone you're always available and you care deeply. So maybe that's the Canadian in you, but I really want to acknowledge you for that and consistently being genuine to who you are. You know, since the beginning of Hootsuite,

before you were the big deal, and to now where the company has grown, you're still the same guy, so I acknowledge you for that. Thank you, little guy. And I feel the same way about you, my friend. You have been consistent the whole way through from meeting you at Runyon Canyon and talking about what's going on in the world to today. You have built an amazing audience of people that love connecting with you.

It's great to see. I appreciate it. Thank you. Final question. What's your definition of greatness? I feel like I'm beating the same drum here, but I think my definition of greatness is legacy and leaving impact in the world behind. And so leaving a mark and, and, uh, creating,

creating value and opportunity for people. Ryan Holmes. Thanks, bro. And there you have it. I hope you enjoyed this episode with one of my favorite human beings, Mr. Ryan Holmes. If you did enjoy this, and if you know other people that would love this, then I'd love it if you would share this out with your friends over on Twitter and Facebook, Instagram, tag me everywhere at Lewis Howes and make sure to tag Ryan as well at Invoker. And you can check out the full show notes and watch the full video interview at lewishowes.com slash three, two, four. Again, Ryan is a stellar human being and he's built an incredible company.

I've used Hootsuite for a long time and it's helped me build my business, schedule out my content, and connect with powerful influencers as well and help me manage all that time. So make sure to check it out. Please share this if you enjoyed it. Leave a comment on the blog or on the YouTube channel wherever you are connecting with this content.

And again, let me know what you thought. We're looking to create more empowering, inspiring content with guests like Ryan. So if this is your first time here, then make sure to subscribe to the podcast on iTunes as well. We are constantly in the top 100 and often break the top 50 overall of all podcasts, over 300,000 podcasts on iTunes now. And we couldn't do this without your support. Getting over 1.3 million downloads a month. And it's all because of you and the quality guests that I'm able to get in front of. So continue to share this out so we can continue to attract and bring on some of the most inspiring people in the world who are changing the game. I love you guys. And you know what time it

is. It's time to go out there and do something great. Bye.