324 Good Hustle vs. Bad Hustle & Building a Billion Dollar Brand with Ryan Holmes

"Live is self-serve." - Ryan Holmes If you enjoyed this episode, check out show notes, video, and more at http://lewishowes.com/324 Get more from Lewis! Get my New York Times Bestselling book, Make Money Easy! Get The Greatness Mindset audiobook on SpotifyText Lewis AIYouTubeInstagramWebsiteTiktokFacebookX

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Lewis Howes?

  This is episode number 324 with CEO of HootSuite, Ryan Holmes.

• 0:07Lewis Howes?

  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.

• 0:33Lewis Howes?

  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, you know, just a few hundred thousand dollars in revenue to

• 1:15Lewis Howes?

  valued at 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 1,000 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.

• 1:58Lewis Howes?

  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

• 2:10Lewis Howes?

  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.

• 2:34Lewis Howes?

  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.

• 2:41Speaker 02

  Good to see you, brother.

• 2:41Lewis Howes?

  Thanks for allowing me to come in your headquarters.

• 2:44Speaker 02

  Our Hoot Nest.

• 2:45Lewis Howes?

  Hoot Nest. I love it, man. This is the headquarters of HootSuite. I'm usually in my Greatness studio, but you're, 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.

• 3:00Speaker 02

  Right, I remember that.

• 3:01Lewis Howes?

  This is the early days of School of Greatness Podcast. So I'm glad that I did it 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 gonna ask some personal questions to get started.

• 3:16Speaker 02

  Alright.

• 3:16Lewis Howes?

  So this is gonna 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?

• 3:27Speaker 02

  Yeah, it's actually like early days, South by Southwest.

• 3:30Lewis Howes?

  We met with Amy.

• 3:32Speaker 02

  In New York and Amy.

• 3:33Lewis Howes?

  We met on Runyon Canyon.

• 3:35Speaker 02

  Runyon Canyon Run in LA.

• 3:36Lewis Howes?

  And you had 200,000 users on HootSuite at the time.

• 3:39Speaker 02

  I remember this.

• 3:39Lewis Howes?

  With like 10 people on the team and now you've got what, close to 1,000 people?

• 3:43Speaker 02

  Yeah, we're getting there. We're just about 1,000.

• 3:44Lewis Howes?

  Getting there, okay. I'm curious, who was your, or what was your biggest dream growing up?

• 3:51Speaker 02

  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, he still owe me a letter back, Richard. I know you're out there. We've been introduced since, but he like, I think he went dark. Anyways, I'm gonna track him down, 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 till I was back in my 30s, when I started a software company,

• 4:36Speaker 02

  and ultimately ended up doing software, which was very close to what grade five me wanted to do.

• 4:42Lewis Howes?

  Really? That was your dream?

• 4:43Speaker 02

  Well, I wanted to make video games, right? And so, you know, I'm in computers, I love, you know, we did, like, there was coding and all this other stuff, but I did so many other things to get back to what grade five me knew I wanted to do.

• 4:56Lewis Howes?

  What was the video game that influenced you the most?

• 5:00Speaker 02

  I love the Ultima series. It was kinda like Dungeons and Dragons video game. You like walk around and you get gold and you find treasures and all this other stuff.

• 5:08Lewis Howes?

  Like Zelda? Is that kinda?

• 5:09Speaker 02

  Yeah, I'm dating myself here, but like Ultima, Ultima 2, 3, 4, 5, it was a series. And then they made Ultima Online. I kinda stopped at a certain point there. But yeah, it was, it was a pretty big franchise.

• 5:21Lewis Howes?

  And who was the most influential person in your, in your life growing up?

• 5:24Speaker 02

  Oh, man, if you, 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. You know, my, my parents, I think, if, if I don't start with that. Parents, obviously, great teachers along the way. Um, high school, I had a fantastic teacher that really created an amazing program for outdoor education, and Barry Reid. And he was a fantastic teacher that, that, you know, I think through high school, it was in grade 11, this program was, was happening. So he had to keep kind of a, a clean nose till he got to there, not get into trouble. And so he probably kept me, unknowns to him, you know, leading up to that program, so I could qualify. And, and, and he was a big influence.

• 6:07Lewis Howes?

  Okay. Um, what was the biggest lesson that he taught you growing up? That you still remember today?

• 6:15Speaker 02

  Well, I mean, I don't, I can't nail one specific lesson that I, that I learned. I mean, that program was very holistic. We got into, you know, things like geography, looking at, at glacial formation. We did native studies, we did basket weaving, we did all this stuff. So, super holistic outdoor leadership. And, and I think outdoor leadership probably, um, it, 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, a group of people that have a, have a collective outcome, getting to the top of the hill on their skis.

• 6:55Lewis Howes?

  Sure.

• 6:55Speaker 02

  And then just thinking about what's the best, smartest way to do that. And some of that early stuff at a, at a young age, you're getting an opportunity to, to lead a little group and, and to take turns, uh, being a leader of a, of a

• 7:07Lewis Howes?

  Outdoor wilderness thing.

• 7:09Speaker 02

  Class in a, in a situation like that. That's a, a pretty, uh, important and, and valuable thing to learn.

• 7:15Lewis Howes?

  Now, is it true you lived on like a hippie foundation, like isolated from the world kind of thing, kind of like thing at some point?

• 7:23Speaker 02

  I grew up, so my parents were unconventional.

• 7:25Lewis Howes?

  Right.

• 7:26Speaker 02

  They, they were both teachers and the

• 7:27Lewis Howes?

  I mean, to knock hippie people and to associate that with hippie.

• 7:30Speaker 02

  I don't take that, I don't take, I don't take, I take hippie as a compliment in a lot of ways, so, um.

• 7:35Lewis Howes?

  But you had unconventional

• 7:36Speaker 02

  I don't know, unconventional upbringing, yeah. My parents were, uh, teachers in the seventies. They decided to leave teaching. Uh, they bought a hobby farm and, um, I grew up, uh, it was, it was off of the grid, so no electricity. I grew up with goats and chickens and honeybees.

• 7:51Lewis Howes?

  For how long, ages what?

• 7:53Speaker 02

  Uh, my, like till high school, till I went away to university more or less. I had kerosene lamps, I had a well.

• 8:00Lewis Howes?

  University is high school in Canada, right?

• 8:03Speaker 02

  Uh, high school, no, high school is high school, university is university, actually.

• 8:07Lewis Howes?

  So until high school?

• 8:08Speaker 02

  Yeah.

• 8:08Lewis Howes?

  You were living with honeybees?

• 8:10Speaker 02

  Actually, no, through high school. Yeah, yeah, yeah. So that, they got a little less into the farming as we grew up and like they were taking us to school and stuff like that. Uh, but I lived and grew up on this property and it was a, you know, beautiful, you know, little farm to grow up on.

• 8:22Lewis Howes?

  And did you have, um, were there other kids in your family or was it just?

• 8:25Speaker 02

  Yeah, I had, I got a younger brother.

• 8:27Lewis Howes?

  Okay.

• 8:27Speaker 02

  Yeah, yeah, so it was he and I and we were out in the middle of nowhere and, uh, yeah, it was, it was a real interesting upbringing.

• 8:33Lewis Howes?

  How, what was it like, you know, being around in the city life after being in the middle of nowhere for your whole

• 8:38Speaker 02

  You know, it's funny, when I was growing up, um, elementary school, you know, younger and 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? So I just wanted to be a normal quote-quote kid, um, like all my other friends. Uh, you know, and then in retrospect, you look at some of these experiences that you have in life that are the, you know, the funny weird experiences. Maybe you hate them at the time and then they end up being really formative.

• 9:13Lewis Howes?

  Yeah, yeah, okay. What would you say was your superpower that you gained from that experience that no other kids had?

• 9:21Speaker 02

  Um, I think that, that, um, in being a little bit of a, you know, 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.

• 9:36Lewis Howes?

  Hmm.

• 9:37Speaker 02

  And, um, and maybe that is one of the things, like I, I don't feel a huge need to conform on stuff. And, and I, 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.

• 9:51Lewis Howes?

  Okay.

• 9:52Speaker 02

  And, um, that maybe started to become a way that I, I self-identified.

• 9:56Lewis Howes?

  Hmm. Do you feel like you've embraced that in business as well?

• 10:00Speaker 02

  Yeah, I think so. I mean, I, you know, I've, I've also, uh, you know, at periods where I've been hustling on my business, you know, I, I've done a number of businesses. I did a paintball company. I did a restaurant. Uh, I did an agency. Uh, when I was doing the agency, I was building software products. Um, you know, I, 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, and, um, enjoyment out of building and creating things. And, um, you know, I guess sometimes like just, just being able to, you know, have the discipline, uh, to sit there and just like get immersed in something kind of, I think

• 10:43Speaker 02

  maybe comes out of that, uh, you know, solitude that I had as a kid and just being able to, to work on my own sometimes when I need to.

• 10:51Lewis Howes?

  I love it. What would you say was the biggest insecurity you had growing up, uh, that took the longest to overcome for you?

• 11:00Speaker 02

  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, you know, hard on other kids.

• 11:14Speaker 02

  And, and you kind of just want to conform, you want to be normal like all the other kids, and 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, you know, I needed to spend more time on that. In university, I spent more time on that than other stuff.

• 11:49Lewis Howes?

  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.

• 11:56Speaker 02

  We're social, yes, absolutely.

• 11:59Lewis Howes?

  Millions of users and fans and followers.

• 12:02Speaker 02

  It is ironic, yeah, you're right.

• 12:03Lewis Howes?

  You were the most isolated kid, probably, in Canada, like, in the top 1% of isolated kids to the most social, essentially, right?

• 12:11Speaker 02

  Right, yeah, yeah.

• 12:12Lewis Howes?

  Interesting. Why do you think you were put here?

• 12:16Speaker 02

  Well, you know, I don't, I don't know that there's any grand plan to why I was put here versus anybody else, but, you know, why I personally am passionate about is, is at this point, creating legacy. You know, I've been blessed with creating a great personal outcome with, with the business and, you know, the businesses I've done. I'm really passionate about, you know, I talk about building a technology ecosystem, creating opportunity for other people, both, both people within HootSuite. I love that, what we're building here, I think, you know, the work that we're doing for our customers is amazing.

• 12:55Speaker 02

  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. You know, we're in Vancouver, I would love to see a legacy that gets created out of this 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. You know, I think, you know, 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, you know, do business and the way we are as a society.

• 13:36Speaker 02

  And so I'm so excited to be a part of that and, you know, looking ahead into the future in terms of witnessing it.

• 13:43Lewis Howes?

  That's cool. Now, how did Hootsuite come about in the first place? And was it an accident or was it intentional?

• 13:49Speaker 02

  So, you know, I think, I think almost any startup founder that says that they planned out their startup to be where it is, you know, five, 10 years later is lying. If they say that they were, yeah, I had, I knew that all this was gonna happen. I mean, there's, there's some emails floating around that, you know, Zuckerberg was talking about how he was working on this fun little project called Facebook, didn't, wasn't really gonna amount to anything, you know, like, there's all that, that kind of stuff that happens out there. And so, you know, we, we saw an opportunity and a need. I had an agency, we had a group working on social media for our clients.

• 14:27Lewis Howes?

  You had about what, 15, 20 people?

• 14:29Speaker 02

  We're about 30 people, 20, 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, they were telling friends and it was growing very virally. You know, flash forward a few years, we had a couple, you know, a 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,

• 15:14Speaker 02

  you know, Instagram, Snapchat, come onto the market.

• 15:16Lewis Howes?

  Pinterest, everything.

• 15:17Speaker 02

  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 is really kind of 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 lifecycle that is relevant to social.

• 15:50Lewis Howes?

  Now, how did you scale? Because you're almost 900-something employees, right? How did you scale from probably the biggest company it sounds like was 30 before then?

• 16:00Speaker 02

  Yeah.

• 16:01Lewis Howes?

  I don't think the paintball company was probably bigger than 30, right?

• 16:02Speaker 02

  No, no.

• 16:03Lewis Howes?

  So your biggest company around was 30, now to 900. Within a few years, how do you learn that new skill?

• 16:09Speaker 02

  As a leader, as a CEO.

• 16:11Lewis Howes?

  Yeah, how did you learn how to do that?

• 16:12Speaker 02

  So, you know, the great thing about running a small business is like everything, the buck stops the year, right? So you're accountable for absolutely everything. I think small business owners are often or learn to become good generalists. So you learn to become the marketer, the salesperson, the productperson, the ops person, the copywriter, the janitor.

• 16:35Lewis Howes?

  Customer support, everything.

• 16:36Speaker 02

  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-MBA's. 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 delegate the stuff you don't like doing.

• 17:19Speaker 02

  Because if you're not aligned with passion to what you're doing, you're not going to, you know, 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 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.

• 17:45Lewis Howes?

  Right.

• 17:45Speaker 02

  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.

• 18:29Speaker 02

  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.

• 18:44Lewis Howes?

  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. 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 or they would not.

• 19:03Speaker 02

  Mm-hmm.

• 19:04Lewis Howes?

  Based on their answer, what would that one question be, the most important one for you to know the answer to?

• 19:10Speaker 02

  That's a real tough question. This is, I alluded to not give me these questions beforehand, just for the record.

• 19:16Lewis Howes?

  Off the top of your head.

• 19:17Speaker 02

  Off the top of my head, I think the one thing that I would ask somebody about is, you know, what is the hardest thing you've done? And, you know, why are you proud of that? And I think that, you know, people that go through some adversity in life, go through, you know, a super challenging project, you know, a challenge in a personal situation...

• 19:43Speaker 02

  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.

• 19:57Lewis Howes?

  I like that a lot. So what would be the answer to that for you?

• 20:02Speaker 02

  I think that the, yeah, that's a, that's a good question. You just throw it right back at me, Louis. Am I interviewing for School of Greatness right now? Can I get a job?

• 20:14Speaker 02

  You know, I think that I've had, you know, a number of different things in my life. I'm trying to think of the most

• 20:22Lewis Howes?

  Adverse moment.

• 20:22Speaker 02

  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.

• 20:39Lewis Howes?

  Really?

• 20:40Speaker 02

  Yeah, and it was

• 20:41Lewis Howes?

  While working with Hootsuite?

• 20:43Speaker 02

  Yeah, but don't tell anybody. This isn't going, this isn't going on the internet, is it, Louis?

• 20:47Lewis Howes?

  Exactly.

• 20:49Speaker 02

  So yeah, no, I crashed a paraglider. I wouldn't call that, so, 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. Yeah, I was like, I missed my landing zone by a lot. I wasn't paying attention. It's flying over a forest and all of a sudden I was too low. And so I knew I wasn't gonna make my landing zone and I was just like flying over a forest and going down, down slowly. And so that was a really, yeah, pretty scary situation. But I had time to kind of just like think about stuff and dread stuff and think about, oh man, this could be bad. This could be, I don't want, you know, I got a lot of stuff I need to do in life ahead of me.

• 21:27Lewis Howes?

  Like I don't want to break my legs or die.

• 21:28Speaker 02

  I don't want to break my leg or my back or be in a wheelchair or something worse, break my neck.

• 21:32Lewis Howes?

  What happened in that moment?

• 21:35Speaker 02

  I froze up.

• 21:37Lewis Howes?

  Was that when you landed?

• 21:38Speaker 02

  No, no, I froze up in the air. So my, I got, I got so pumped, my forearms, my muscles were frozen in fear. And I, I, the adrenaline kicked in overtime. And, 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 like trying to aim for it. And then I flew right over the clearing because I couldn't control my muscles.

• 22:03Lewis Howes?

  Oh my gosh.

• 22:04Speaker 02

  I was just like completely, I didn't have fine motor controls. I was just like pumped, like rigid. And so I, 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 lane road. And back and forth and back and forth, trying to miss trees on either side.

• 22:26Lewis Howes?

  No way.

• 22:27Speaker 02

  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. Uh, I landed on the ground, full force, my feet, I rolled over. Uh, it kind of got slowed down by the branches and then I started patting myself down to see if there's a branch going through me.

• 22:47Lewis Howes?

  Oh my gosh. Cause there was so much adrenaline, you probably couldn't feel it.

• 22:50Speaker 02

  Yeah, I, 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. But I didn't. And I was like, that's amazing. I started wiggling my toes, wiggling my hands. I got up. My, my own screensaver to this day is, uh, it is a picture of me when I landed on my paraglider.

• 23:06Lewis Howes?

  Oh my gosh.

• 23:07Speaker 02

  And I pulled up my, my, my lines and I took a photo of it. And, um.

• 23:11Lewis Howes?

  Let me show this on the video.

• 23:12Speaker 02

  Yeah. So I, I took a snap of that, uh, to catch a, catch a picture of my happy face in that moment. And, um, I can, I can send you a snap of that, Lewis, and you got it for later. But, uh, anyways, I came out of that with, um, with actually not even a single scratch.

• 23:30Lewis Howes?

  What?

• 23:31Speaker 02

  And I was super, super pumped.

• 23:32Lewis Howes?

  How fast were you going?

• 23:33Speaker 02

  Uh, you know, probably 20, 30 K and, and then kind of slowed down. Miles per hour. That's going to be, uh, that's going to be about 15, something like that. Yeah, yeah, yeah, yeah. So.

• 23:43Lewis Howes?

  Still.

• 23:44Speaker 02

  Not, not super fast, but it was high. I mean, it was tree height, then it dipped straight down. So.

• 23:48Lewis Howes?

  Wow.

• 23:48Speaker 02

  Uh, I came out of it okay, carried all my, packed up my wing, carried it out of the forest. And, uh, and then I went and, uh, relaxed and lied down in the sun and just thought about life.

• 23:58Lewis Howes?

  What opened up for you in that moment?

• 24:00Speaker 02

  I think, um.

• 24:03Speaker 02

  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 here? How am I going to, you know, make the best use of it 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 kind of keep that as a little reminder. Wow. It's one of the moments. What's the other moment, most adverse moment?

• 24:45Speaker 02

  Most adverse moment, that's a moment of adversity in a flash. Short window. Yeah, yeah. There's like three month windows. Longer ones, you know, I think. Was there ever a moment Hootsuite was not going to last? 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 feel like we've been really blessed and I think one of the bigger moments, you know, of adversity was dropping out of university also. Really? Yeah, that was, that was a really tough challenge. 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 that's what we're kind of wired from, you know, a very early age.

• 25:27Speaker 02

  And I had like 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, okay, well, that's great. What are you going to go do? And didn't, 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, you know, it was, it was a moment of adversity and also I think it was very formative, you know, getting back to hard times in your life and how that changes your life and why did I do it? You know, my motivations for doing it, the program I was in, I wanted to, I always wanted to be an entrepreneur and the program I was in was teaching me to be an employee.

• 26:08Speaker 02

  And I purposely sabotaged myself so that I wouldn't be a suitable, I wouldn't be a good employee. Sure, sure. 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, you know, make this decision. And it was a good one in retrospect.

• 26:30Lewis Howes?

  What's the vision for HootSuite moving forward? What's your vision for it?

• 26:36Speaker 02

  We've got a big vision. You know, 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.

• 27:20Lewis Howes?

  Right. Unless you're in London.

• 27:22Speaker 02

  Do you have a home phone?

• 27:24Lewis Howes?

  No, I'll cell phone.

• 27:25Speaker 02

  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 or 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?

• 27:47Lewis Howes?

  Yeah.

• 27:47Speaker 02

  And so if you think about that, I just, I always find that interesting because so many people that are non-millennials or, you know, 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, you know, 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.

• 28:09Lewis Howes?

  They're going to text.

• 28:09Speaker 02

  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?

• 28:19Lewis Howes?

  Yeah.

• 28:20Speaker 02

  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, you know, a trillion dollar opportunity. And we just want to continue to grow our business there.

• 28:46Lewis Howes?

  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?

• 29:06Speaker 02

  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 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 that

• 29:27Lewis Howes?

  It's like no sleep.

• 29:28Speaker 02

  No sleep, yeah. I stayed up and I worked 24 hours straight. And it's like, that's bad hustle. Congratulations. You're gonna give yourself a heart attack and die. You're like, don't do that. That's not, that's not healthy hustle. What's good hustle? Those are the things I want to focus on. And

• 29:43Lewis Howes?

  What are those things?

• 29:44Speaker 02

  You know, good hustle, you know, it's working, it's working smarter, not harder. It's like getting exercise and balance in your life. It is attacking things with passion, sure. This piece, I'll share with you. It's awesome. And it resonates so well with a lot of people. But, you know, 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.

• 30:24Lewis Howes?

  That's why you got into yoga, I think, right?

• 30:26Speaker 02

  Yeah, it's why I got into yoga. Yeah, absolutely. And out of that, like, you know, balance and, you know, not sitting down at your desk all day, you know, I created my stand-up desk company because I wanted to, you know, give that out to people and, you know, put that back to the world to give people a little balance in sitting down and standing up.

• 30:42Lewis Howes?

  What's the, I bought one of those. They're great, by the way. My video editor used it. What's the link for that?

• 30:47Speaker 02

  It's ori stand, O R I, like origami, stand.co.

• 30:51Lewis Howes?

  Okay, cool. Awesome. So, routine then for?

• 30:54Speaker 02

  So, yeah, I do probably, I exercise probably three, four, sometimes five days a week. I know, I try to get a little something in. You know, we got a gym at the office. I'll go and I'll take off at lunch and I'll go work out a couple of days a week. I'll go for a run. I'm trying to get faster at running right now. Cycling season's on. In the winter, I backcountry ski. You know, I just try to get a little bit of something everywhere and, you know, 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.

• 31:25Lewis Howes?

  I love that. Uh, who do you learn from the most in your life right now?

• 31:30Speaker 02

  Other than Lewis Howes. Um, I, you know, I, I, I have, I talk often about like the Mr. Miyagi. Um, you know, the mentorship, a lot of people ask me about who I learned from, who's been my biggest mentor in life. And I, I don't necessarily, um, believe in the idea of one mentor that like solves it all for you. When I was in B school, they, one of the big things is go find a mentor. And I, I appreciate that, uh, in, 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 Reid, uh, and there's been others along the way that I've learned a ton from.

• 32:12Lewis Howes?

  Um. Is there one person right now in your life, whether it be here at Hootsuite, your personal relationships?

• 32:18Speaker 02

  Right.

• 32:19Lewis Howes?

  That you learned so much from just by that relationship?

• 32:22Speaker 02

  Yeah, you know, I, I think, as I say, I think it evolves over time and right now, uh, yeah, there are people in my life that I'm learning a lot from. Um, you know, a, a couple of my investors, I learned a ton from them. They've been super fantastic. Um, I've, I've met with, uh, you know, when I, 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, and, uh, hopefully we can both gain knowledge and, and experience out of it. Um, but yeah, you know, there are, there are people I, I am learning from all the time.

• 33:05Lewis Howes?

  What's something you're most proud of that people don't know about?

• 33:08Speaker 02

  Oh, man, I'm, I'm, I'm an oversharer, Lewis, you know, this, probably everybody, I'm pretty transparent on this stuff. I'm super proud of, uh, TMBT, this is a foundation that I created. Um, and, and the goal of TMBT is to help, uh, accelerate young entrepreneurs. You know, I'm a young entrepreneur, so I have a paintball company when I was in high school. Uh, and, and, um, 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 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, you know, I'm a member of YPO, I poll people

• 33:53Speaker 02

  in YPO and I ask them, how old, you know, 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, you know, it's going to ultimately increase GDP, it's going to create more value, more jobs in the economy. And so that's my, my little piece is to find and try to help accelerate a small group

• 34:37Speaker 02

  of young entrepreneurs and that's a program that I'm really passionate about.

• 34:42Lewis Howes?

  If you had all these kids in one stadium that were part of this program.

• 34:48Speaker 02

  Right.

• 34:49Lewis Howes?

  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?

• 35:02Speaker 02

  I mean, I talked about the good hustle, 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, in a good and bad way. You are crushing through walls every day. You've got these, 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 go to your Your mental game's gotta be as strong as your physical game.

• 35:40Lewis Howes?

  Yes.

• 35:40Speaker 02

  You need endurance on both fronts, but you gotta be able to persuasively talk about what you're going to do to get people aligned around a vision.

• 35:49Lewis Howes?

  Right.

• 35:49Speaker 02

  To, you know, move the ball ahead and to, and to, and to work through bureaucracy. And bureaucracy is the enemy of entrepreneurship, right?

• 35:56Lewis Howes?

  Sure, sure, yeah.

• 35:56Speaker 02

  And so, uh, you, you have to be able to do that. And, and that, that just takes hustle. It takes perseverance. It takes uh, self-discipline and motivation and, and you gotta find that yourself.

• 36:07Lewis Howes?

  I love it. Okay. Uh, I have a rapid-fire question section. This is the first time I've ever done a rapid-fire thing.

• 36:13Speaker 02

  Oh, I'm honored to be your first guinea pig.

• 36:15Lewis Howes?

  Well, one, because we only have a few minutes left before the crowd comes in. Um, and then I have a few finishing questions after that, which will be more thoughtful. Um, or, or longer answers, I should say. So the rapid-fire, uh, and we already talked about this a little bit, but overall, what are you most proud of in your life?

• 36:34Speaker 02

  Uh, well, you know, at this point, I'm, I'm really proud of HootSuite. I'm proud of everything we've done. Um, that, uh, that to me, I think is, is probably it's been my baby. Uh, and, and until I have some babies, uh, which is, you know, obviously coming up in the next little while. I'm really excited about having kids at some point. Uh, I'm not, I'm not putting out a date or anything. It's not happening. There's nothing in the, no buns in the oven right now, but I'm excited about doing that in the future. Uh, for now, uh, this is my baby and then I'm, yeah, I'm really proud of what we've done.

• 37:02Lewis Howes?

  Um, if you could have anything you want after HootSuite, whenever HootSuite's you're gone from HootSuite or many, many years from now.

• 37:10Speaker 02

  Yeah.

• 37:11Lewis Howes?

  What would be the next dream if you could say, this is what I want afterwards? Anything at all?

• 37:15Speaker 02

  Uh, well, you know, I mentioned legacy. So, uh, you know, I just wanna be able to create a legacy in an environment that helps other people, uh, achieve their dreams. And so, you know, I think that, uh, technology is the way that I would do that. And so I'm, I'm excited about creating and helping create a technology ecosystem in my backyard, Vancouver, Canada in general.

• 37:34Lewis Howes?

  Cool. Uh, 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?

• 37:47Speaker 02

  Oh, man. Um, you know, the, the

• 37:51Speaker 02

  That is a great question.

• 37:53Lewis Howes?

  There's lots of challenges, obviously.

• 37:55Speaker 02

  Pick your battle, right?

• 37:56Lewis Howes?

  What speaks to you?

• 37:57Speaker 02

  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 gonna solve that, and I believe that we solve it through technology. Like, are we gonna convert to a hydrogen electricity economy? Are we gonna all go Tesla? I think the technology is solving that, and that's gonna help with our greenhouse emissions. Beef, you know, 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.

• 38:42Speaker 02

  And so that solves the problem. I think that I would, I'm kind of would be the kind of guy that would sprinkle it around in a lot of different areas. Environment, I think, technology, and I think food is also an interesting area to go for.

• 38:56Lewis Howes?

  Cool.

• 38:57Speaker 02

  I'm not rapid firing very well here.

• 38:59Lewis Howes?

  That's all good. When I, your favorite business leader, what's the one person you would say right now?

• 39:05Speaker 02

  You know, I...

• 39:07Lewis Howes?

  Beside yourself.

• 39:09Speaker 02

  Yes, modesty for bids, but I'm a huge fan of Richard Branson. I think he's just like, 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 gonna 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.

• 39:34Lewis Howes?

  The hobby you love the most, the thing that brings you the most joy?

• 39:37Speaker 02

  I think, it's a, 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's great. Obviously, I get my endurance 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 just, I find that's my way that I relax.

• 40:00Lewis Howes?

  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?

• 40:10Lewis Howes?

  So reverse wording, if it was stamped on your forehead, what would you put on your forehead?

• 40:16Speaker 02

  It would have to say free hugs.

• 40:17Lewis Howes?

  Free hugs?

• 40:18Speaker 02

  Yeah, I mean, you can't be mad at a guy with free hugs on his forehead.

• 40:21Lewis Howes?

  Okay, I like it. Well, what if it was one that people couldn't read, only you read in a mirror?

• 40:26Speaker 02

  Hmm, only I read in a mirror.

• 40:28Lewis Howes?

  A message that you saw when you looked in the mirror, so it was reversed.

• 40:31Speaker 02

  Alright, alright, so it's just I can see.

• 40:32Lewis Howes?

  Not to the world, but just to you. As a reminder.

• 40:36Speaker 02

  Maybe it's, you know, it's along the lines of seize the day, but like, life is self-serve and, you know, go get it. And maybe it's life is self-serve.

• 40:44Lewis Howes?

  Cool, I like that. If you could be anyone for a day, who would you be?

• 40:49Speaker 02

  Right. Oh, wow. If I could be anybody for a day, um, I would be, huh. That's, there's so many great opportunities there. Uh, I think I'd be lying if I said I wouldn't want to be a woman for a day. Like, how crazy would that be to just like, switch genders and check it out for a day? I think that would be a really interesting, I mean, I, look, I could say I'd want to be Barack Obama for the day and like, see what it's like to be behind, be on the big desk, but I think like, that's a really interesting, uh, experiment just to see what it's like to be another Jennifer day.

• 41:22Lewis Howes?

  Which, which woman?

• 41:23Speaker 02

  Oh, which, which woman, okay. Hillary Clinton for the day.

• 41:30Lewis Howes?

  Okay, uh, we're in the last few questions. 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? What are you hanging out with the most? I know Snapchat, you're still picking it up, but where should we follow?

• 41:44Speaker 02

  Yeah, I got a player on Snapchat, I'm, I'm @invoker, I-N-V-O-K-E-R, pretty much everywhere. Uh, Twitter, Facebook, I'm the Ryan Holmes, or the official Ryan Holmes, uh, on Facebook, I got a page there.

• 41:56Lewis Howes?

  Nice.

• 41:57Speaker 02

  And, uh, that's where you can.

• 41:58Lewis Howes?

  Where do you hang the most?

• 42:00Speaker 02

  Uh, I, I'll flip between Twitter and Facebook quite a bit. Instagram's fun, I share some posts on Insta, of course, yeah.

• 42:07Lewis Howes?

  So make sure, make sure to tweet @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. Um, last few questions. What are you most grateful for currently in your life?

• 42:25Speaker 02

  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 to them.

• 42:50Lewis Howes?

  That's cool. That's cool. Okay, many, many, many years from now, it's the final day. You've created your legacy.

• 42:57Speaker 02

  Lying on my deathbed.

• 42:59Lewis Howes?

  You've done everything you wanted to do. And peaceful, everyone's there, it's joyful moment. But for whatever reason, everything you've created has been erased from time. So you've written many books by now, but they're gone. Every article, gone. Business, gone. And your great, great, great whatever grandson 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 need 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?

• 43:37Speaker 02

  Wow.

• 43:38Lewis Howes?

  Without prepping you. Without prepping you, obviously.

• 43:45Speaker 02

  I would say, so getting back to, you know, life is what you make of. 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, you know, everybody has limitations in life and you gotta get past those things. So that would be, you know, obviously a big theme for me. I think that...

• 44:10Lewis Howes?

  That's one.

• 44:11Speaker 02

  Yeah, okay, that's one. I'm bundling those two things in there. You know, I think that...

• 44:18Speaker 02

  The love of family and friends is obviously, you know, 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

• 45:03Speaker 02

  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. I think that that's, you know, just a part of this interesting life that we have, the mortality that we have for now, maybe that changes in the future. But, you know, I get excited about, you know, experiencing everything we can on this planet and then, you know, at some point in the future, maybe we get to go beyond.

• 45:41Lewis Howes?

  Right, that's cool. Those are great three truths. Before I ask the final question, Ryan, I want to acknowledge you for a moment.

• 45:47Speaker 02

  Okay.

• 45:48Lewis Howes?

  For your incredible friendship. I don't think, you know, people know how intelligent, you 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 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.

• 46:12Speaker 02

  All right, make me blush, thanks.

• 46:14Lewis Howes?

  Maybe that's a 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.

• 46:29Speaker 02

  Thank you, Louis. And I feel the same way about you, my friend. You have been consistent the whole way through from Yeah, meeting you at Runyon Canyon, talking about what's going on in the world. And to today, you have built an amazing audience of people that love connecting with you. And it's great to see.

• 46:47Lewis Howes?

  Appreciate it, man. I appreciate it, thank you. Final question.

• 46:49Speaker 02

  All right.

• 46:50Lewis Howes?

  What's your definition of greatness?

• 46:52Speaker 02

  I think, you know, 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, you know, behind. And so, you know, leaving a mark and creating, creating value and opportunity for people.

• 47:10Lewis Howes?

  Ryan Holmes, thanks, brother.

• 47:11Speaker 02

  Lewis, thank you, sir. Appreciate it.

• 47:16Lewis Howes?

  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, @lewishouse, and make sure to tag Ryan as well, @invoker. And you can check out the full show notes and watch the full video interview at lewishouse.com/324. 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.

• 48:00Lewis Howes?

  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

• 48:45Lewis Howes?

  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.