Shaping a Career in the Outdoor Industry, with Chris Jerard

In this episode of the Entrepreneurship@DU Podcast, host Joshua Ross interviews Chris Jerard, serial entrepreneur and current VP of Marketing at Outside. They discuss Chris’ journey from an English and poetry major at the University of Colorado to becoming an influential entrepreneur in the outdoor industry. Chris shares how his early entrepreneurial experiences, from running a painting business in college to co-founding Freeskier Magazine, shaped his career.   

The episode concludes with insights into Chris’s current role leading experiential and event marketing for Outside, including the successful launch of the Outside Festival and his passion for outdoor adventures. 

 Transcript:

Joshua Ross (00:03): 

Name is Joshua Ross and welcome to the entrepreneurship at DU podcast. I wanted to be a writer. I was really into the creative process and did not think of myself as an entrepreneur. I thought of myself much more, like more of an artist, I guess, writer. 

Joshua Ross (00:24): 

In this episode, I’m joined by Chris Jerard, an entrepreneur, and currently the vice President of Marketing at Outside. Chris shares his fascinating journey starting as an English and poetry major at the University of Colorado and how he took these skills and went on to build several successful businesses in content creation and digital media within the outdoor industry. We also dive into an ironic and entertaining story about Chris’s first attempt to land a job at outside and how life came full 

Chris Jerard (00:57): 

Circle. I was 22 years old on my motorcycle in Santa Fe trying to get an internship so that I could eventually get a job at a ski magazine and had applied at outside and was in the parking lot in Santa Fe and my motorcycle calling trying to get into the building. They literally would not let me in the building. 

Joshua Ross (01:23): 

Today Chris is leading experiential and event marketing for outside, which includes the outside festival and summit. Here’s my conversation with Chris Jerard. Hey Chris, welcome to the podcast. I’ve been looking forward to having you on. 

Chris Jerard (01:42): 

Yeah, thanks for having me, Josh. Excited to be 

Joshua Ross (01:43): 

Here. Cool. Well, it’s nice to have a fellow boss. So let’s start at the beginning. You graduated from the University of Colorado in 1998 with a degree in English and poetry, which isn’t the most common path into entrepreneurship. And so I want to get a little context to what inspired you to go down the entrepreneurial route and especially in content creation. 

Chris Jerard (02:09): 

Yeah, I was a creative writing major. I was a biology minor actually, and I chose that. That was my passion. I wanted to be a writer. I was really into the creative process and did not think of myself as an entrepreneur. I thought of myself much more as a more of an artist, I guess writer. And what I didn’t realize is that I’d always kind of been an entrepreneur. I had always hustled. The motivation earlier in my life was like I needed to make money somehow. So I stuffed flyers in my neighborhoods mailboxes and just looked for ways to create value, I guess is how I would put it. Now, it was odd jobs, it was lawn mowing, it was whatever someone Mrs. Jones would pay me for, and that turned into actually a painting business when I was in college. So I paid for college by running a painting business back in my hometown of Durham, New Hampshire, and ended up hiring all my friends and started to get some experience as a little bit of an operator, had to start a company, create a logo, do advertising, and that was in parallel to what I was doing in school and what I was doing in school was really what my passion was. 

(03:46): 

So I kind of financed my passion by creating ways to make money. So not a normal way I guess, of going into what ended up being my career along the way. When I was a senior, I started asking myself that same question. 

(04:10): 

What are you going to do, dude? You’ve got a degree. And effectively my thesis was a book of poems and I was really into that and I was like, are you going to be a poet? Are you going to actually be an artist? And I came to the conclusion, I remember it really clearly that this was not going to be how I was going to make a living. I didn’t want, frankly, I didn’t have the wherewithal for the lifestyle in a way. I was like, I am going to combine what I’ve learned here with something else and find a way to make a living. And what that turned into right out of college was find a job as a writer for a magazine and an established magazine would’ve been great. No one would give me a job. So that turned into being on the founding team of starting a magazine, which I didn’t think of as a startup, but was my first real entrepreneurial, real business in my career. 

Joshua Ross (05:22): 

As you said, you couldn’t get a job at a magazine. You were one of the founding members of Free Skier, which took this off your LinkedIn became the largest independent ski magazine on the planet, which I love. So I believe this was your first entrepreneurial endeavor, I thought, until you just told me about all the other things that you did. So what’d you learn from this 

Chris Jerard (05:46): 

Experience? Oh, so much. I mean, it was another, I mean, got lucky in a lot of ways. I think that’s part of being an entrepreneur is taken swings, and as I described, I made the decision, I think there’s a couple things, right? I made the decision that I wanted to combine something I knew I could do, which was right. I’d just been trained in that with the business of media and I had moved to Colorado to ski. That was my passion. So it’s this combination of passions and I started looking around, is there a place that would hire me? And as I said, I didn’t have a lot of luck. I was very persistent and eventually ran into these guys who were starting a new ski magazine and that experience, one of staying persistent and not a lot of doors shut in my face and having the faith that if I really wanted this, and I’ve said this to students before, what are you willing to sacrifice? 

(07:05): 

What are you willing to do if you really know? The hard part is understanding what it is you wanted do. I knew that I wanted to work in media. I knew I wanted to work in outdoor ski, all of those, the adventure in that area. And so jumping in on board with those four other guys, and we were all in our early twenties and there was so much, we didn’t think of it as a startup. That’s the funny thing is it was not your traditional today you say startup people know what that means. Even entrepreneur, I don’t even think any of us really thought of ourselves as entrepreneurs. We just loved skiing and we were bringing something new to the market, which was youth culture, skiing, free skiing. At that point even that was not even a word, that was a word that we had to describe and it was a new thing that we’re bringing to the market completely. 

(08:01): 

And that was really hard that I’ve spent a lot of time on the phone explaining what free skiing was. And that would be another sort of kernel of learning was we were building something from the ground up and people didn’t understand it and didn’t necessarily want it, but we knew there was a small dedicated group that was driving culture and leading in that area. And we had the faith and the confidence that if we stuck with it, that it would become something. And it took years of that along the way. We had a lot of fun. We got to ski and it was a creative endeavor. There was photography, there was writing, it was this combination of all those things, trying to sell advertising, make the business work. And it took a few years for the business to really work. So learned a lot about persistence and resilience and also if you really care and love something, those things are not as hard. You can be persistent when there’s purpose underneath the thing that you’re trying to start. 

Joshua Ross (09:14): 

So you mentioned this whole thing of there has to be this kind of sacrifice too. So what was the sacrifice? 

Chris Jerard (09:20): 

Money. Money, interestingly enough, going back to that decision of I don’t, I’m not going to be a poet, I sort of ended up being one in a way in that in order to get that job, I had to be really willing to forego some of the things that maybe some of my classmates who were getting into the workforce and really trying to build their career around, okay, this is a good job. I can make this much money. I get these benefits, get a 4 1 1 K. None of that stuff existed. So in fact, I still had to run a painting business on the side to make ends meet for years. Eventually that changed. Eventually when I was there for 10 years, we acquired another magazine and eventually it became a normal job with health insurance and all those things, but we had to kind of build it up from the beginning. 

(10:26): 

So I would say that monetary gain was one of the sacrifices. I loved it, but I had to travel a lot. That wasn’t a sacrifice for me when I was 23 harder now, once you have a family and those kinds of things. So there always is something I think that you have to, I really do think in entrepreneurial endeavors, the idea of balance is kind of a myth. Eventually you can find balance, but there’s always some aspect that you have to say, well, that part’s going to be out of balance for a little while, not forever, but how long are you willing to kind of persevere? 

Joshua Ross (11:10): 

It’s a great point. You really have to believe in what you’re doing and have this conviction and also a passion for what you’re doing. Because I remember in my own entrepreneurial journey when we weren’t making any money and I was seeing friends and classmates and colleagues and investment banking or working for startups that were IPOing and all of a sudden they were flush with cash. And I was just slogging through trying to get the next customer and make payroll. And it’s tough and it can be a little defeating at times. 

Chris Jerard (11:46): 

Absolutely. I mean, you do have to have a belief in what you’re doing when it’s hard. I mean, there are other stories, not mine, but there are others where you get on board and it’s a rocket ship and all those things come together. So there’s not one story. But in my case, I had to sacrifice the, and that comparison as a young person right out of college, I’ve heard some great advice around that in your twenties. And I would say my experience kind of bears this out, that you really don’t worry about that. Don’t worry about comparing yourself to others and the money. It is the time in life when you really can be incredibly thrifty. You don’t need much, you don’t have dependence and all that stuff eventually has a way of showing up in your life in one way or another. And when you’re free like that, you can get so much done when you’re in that time period. If you really are focused on, am I learning? Is it what I like to do? Am I getting the skills that can pay off later? 

Joshua Ross (13:00): 

You’ve had a pretty amazing journey as a founder, but I want to focus on two businesses. You created INL Media in 2014 in Rome Media in 2017. So what was the reason you started these companies kind of building off of what you did from free skier and all your entrepreneurial adventures? I 

Chris Jerard (13:22): 

Would listen to some of the younger staff debate some things that were problems or issues in their mind that I had actually already lived a couple times. I mean, you can only write so many reviews on ski resorts. There’s only so many in the world and just there’s this little part of me, and I remember it really clearly that said like, oh, is this year, is it going to be Telluride or is it going to be Aspen or Whistler? That’s number one. And in the back of my head, this little voice said, who gives a shit? And that was to me like, okay, you’re done. And I think that’s an important point just from the standpoint of what we’re talking about before that I cared so much about that business and about the community. And as soon as that little voice said that in the back of my head, I was like, you’re done. 

(14:18): 

Okay, you got to go do something else. And so I started, I kind of opened myself to that. I had a great gig, man. I mean skiing all over the world every year, going to Alaska for a skier, which was my passion. It was a very good gig, but I’d hit a ceiling creatively and from a business perspective. And so started looking for some other stuff, and this was about 2008 and realized that there were some really interesting things going on with some of my friends who were content creators and that they were utilizing these new platforms, specifically Facebook and Twitter at the time. This was pre-Instagram to put messages out in the world around the content and the stories that they were living. And I went and saw a friend of mine, chase Jarvis, and he opened up his Google Analytics for me and was sort of like, Hey, I was wondering, you’re publishers. 

(15:20): 

This is how many people are watching my videos. And I was like, oh, wow, everything’s about to change. This was way before the concept of influencers or influencer marketing was a thing. The individual is a conduit to many now it’s the beginning of a new era of media. And I was fortunate to be in a place where I really understood media and knew a lot of folks who were creating content as athletes and artists. That was the first kernel for inkwell is that I saw that there was this new emerging class of content creators who didn’t need my permission as a magazine person or didn’t need anyone’s permission to put content into the world. And it was discoverable based on was it attention grabbing? Was it educational? And that got my wheels turning on, I need to learn about this as a media person and a creative, and maybe there’s some business in it. 

(16:26): 

So I actually ended up working with Chase for a number of years, and we did some really, really fun interesting things with a lot of big brands, and it kind of took me out of the outdoor business for a little bit and put me in like the real world. We worked with Apple and HP and Nike and Nikon, and that set up the landscape for me to start to work with individual content creators. And that was what I saw as an opportunity is that not a lot of people understood the individual as a media company or as a media entity. And the thought was, if I could network these folks and their audiences, you could build a rather large media platform. And that was just an idea. I was passionate about it because I got to work with people I really admired and that were doing things that were mostly in the artistic or athletic space and things that I thought were really cool and help them refine that into media platforms on their own, sort of their own that they could just as we had with the magazine, then monetize that through brands. And that turned into inkwell, which was really a creator marketing agency, content agency where we both helped individuals create their social feeds and put their content out at scale and then connected those folks with brands. Sounds pretty rudimentary now, but in 2010 there weren’t a lot of people doing that at all. So it grew pretty quickly. 

Joshua Ross (18:11): 

Do you think without your background with free skier and the people that you came into contact with, and I’m imagining you had a pretty large network by that time and a pretty solid reputation in the industry, you could have been successful building out what you did? 

Chris Jerard (18:29): 

I think that the path with Free Skier set me up because of a lot of the relationships. I had relationships with a lot of really accomplished skiers and snowboarders, climbers, people in the outdoor business that were in that world famous and needed help. So it was the time I had put in with Free Skier and Snowboard magazine that sort of set that network up, which is always a big part of building anything. Your network is very helpful. And those folks trusted me because of the work I had done around the magazine for a lot of years in that community. I truly still care and did care very much about the skiing and snowboarding community. And so some folks really came to me looking for help. And so yes, the experiences and all that time put in there started to pay back really rapidly on when I started. This was the first, I would say, real business that I started on my own. 

Joshua Ross (19:47): 

So it goes back to what we were talking about in your twenties. You were doing things in terms of building trust, which is so important that you probably had no idea that you probably wanted to do the right thing and be ethical and have good relationships, but you are building this capital that you were able to use later on, which is awesome. 

Chris Jerard (20:05): 

Yeah, for sure. Community is really important to me and I think it’s in a lot of businesses, certainly in the world that I’ve lived in the outdoor world and the media world, when you’re selling stuff, trust is really important. I talk about this a lot in what we’re doing now, that first understanding you have to be understood, your brand has to be understood what service you provide has to be understood. And that understanding then can lead to trust. And then trust is ultimately why people buy your stuff, whether it’s in a consumer or it’s on a B2B level or they to work with you or for you, they have to have some level of trust. So I think the free skier days taught me that for sure, working in a tight community with a lot of brands, and that’s how it kind of works in a community. 

Joshua Ross (21:07): 

So you have inkwell and then you decide to start Rome in 2017. What’s the connection? What was the drive behind starting a second company? 

Chris Jerard (21:20): 

Yeah, two companies at once. I had a mentor just on that front who was an advisor at inkwell, and inkwell was a bootstrapped entity. So Kate actually the same mentor early in the beginning of inkwell when I was trying to figure out how to put that idea of networking humans together. He said, just get five clients. That’s really good advice. He said, just get five. Get five. See how it goes. And with a bootstrapped approach, that’s what you should do is just get a couple clients, see how it goes, service those clients. So the same guy, when I was thinking about starting Rome, it was like that’s not normal to have two businesses at the same time. People do it, but it’s not just so you know. And the impetus was that we were building platforms at inkwell as a, we were agency really, right? 

(22:17): 

Building platforms for brands and for humans, for athletes and artists. And at some point we started to go, well, why wouldn’t we build one for us? We had the skills, we knew how to use the platforms. And so that was the idea was well, we could actually build a media entity as opposed to just being a services based, build our own audience and maybe take some of these folks who are our clients and bring an idea for a new kind of a next generation National Geographic was the idea Adventure from the field was what our tagline was at the beginning. Take real time adventure, real time storytelling that you could now do without a lot of money or even equipment you could basically do from your phone and bring that to an audience with all of these athletes and photographers and filmmakers. And that turned into a deck and then that deck went out and this was my first go at raising capital to enterprise venture capitalists. 

(23:27): 

And that was a whole new experience. I would say taking that idea, the motivation really had been we should do this for ourselves. And it doesn’t exist right now. There’s not a creator owned media company in the space. So there was an opportunity, we were well positioned. I again get to work with all these people like Jimmy Chin and Travis Rice and Sasha de Julian friends who had big audiences and who saw the idea, ran the idea by them and said, yeah, that’s something I would either be an advisor for or invest in and then put that whole presentation together and brought it to funds and then started knocking on those doors. 

Joshua Ross (24:16): 

Both Rome Media and inkwell ended up being acquired by Outside Interactive. Can you walk us through the decision making process for you when it came to selling these two companies? What factors influenced your choice and what made you do it? 

Chris Jerard (24:32): 

Well, I met the founder and CEO of outside before it was outside when it was Pocket Outdoor media. Robin Thurston, and I actually met him who introduced me. Josh was John WinDor, introduced me to Robin Thurston. And I think it was just a kind of casual like, Hey, you should meet this guy. He’s doing some interesting stuff. And Robin came over to my office at inkwell in Boulder and we had a good, we just kind of hit it off on the first conversation. And I often think about that conversation in terms of the answer to your question as I had no idea who really, who Robin was at that point, meaning I had done a little, usually try to know who you’re talking to a little bit, but I didn’t know what his ambition was. He didn’t at that point share it with me. And we just had a good conversation. We talked about media and media theory and what was going on in the world. This was just before the pandemic. 

(25:35): 

We stayed in touch. And I think about that conversation sometimes because you never really know who might be the conversation that becomes influential in one way or another in your life. And through the course of our conversation through the pandemic, I went and raised another round. So I had reached out to him at that point and asked him if he knew anyone that might be interested and he was helpful in that and we continued to stay in touch through that conversation. It was a two year conversation. It was kind of back to trust and understanding. I started to understand what he was trying to do, and I think he started to understand what I was at that point doing. And at some point it really just turned into him saying, Hey, would you be interested in coming in, joining me? And at that point, we were really just talking about Rome. 

(26:35): 

I didn’t actually have any intent of selling inkwell. I had no investors and it was doing well, and I had a couple of that were really great at operating it. So I wasn’t looking to sell that Rome. Of course, I wanted to sell mean. So a lot of times you raise, well, certainly your investors want you to sell and that’s your fiduciary responsibility. So I was very interested. I also, looking at the landscape at the time and looking at what Robin was doing, it just made a lot of sense. It was a perfect fit. Going way back to where we started the conversation when I was talking about the magazines, that wouldn’t give me a job. I have a funny story that I was in at, I guess I was 22 years old on my motorcycle in Santa Fe trying to get an internship so that I could eventually get a job at a ski magazine and had applied at outside and was in the parking lot in Santa Fe in my motorcycle calling, trying to get into the building. 

(27:45): 

They literally would not let me in the building. So fast forward 23 years later, they let me in the building. And that was the progression of my relationship with Robin and the reasons to do it. The scale that he was envisioning was exciting and inspiring to me and to be able to take what we had, which was going well and would’ve been difficult to achieve the kind of, I mean, he had quite literally raised a hundred times more capital than me. So the Annie had outside magazine now he had all these storied brands, he had ski. And so what he was doing was and is doing what we are doing now was I could see it and I could see where the integration of Rome and my network and all those things we talked about before could be really impactful to help get it to build this platform that inspired people to get outdoors. 

(29:02): 

So those were the first parts of it. Do I like him? Do I trust him? Do I like the vision of where he’s going? Those are the first two gates. And then you start to get into terms and all that kind of stuff. And it was a good deal. It was a fair deal. He did end up saying, Hey, if you’re going to sell me this, you have to sell me inkwell as well. That was a little bit of a curve ball because as I said, I hadn’t expected that. But again, went trusted him, saw where the integration of that business could be helpful to what outside was trying to do. And it was a fair offer and so away we went. 

Joshua Ross (29:48): 

That’s a great story. And Robin, his history in Pass is pretty impressive. I mean, cyclists entrepreneurs started Matt, my Ride, and Matt my run, and I believe he sold to Under Armour at some point in time and wanted to come back and start something new. I remember when he bought outside, because Outside Magazine for me was the only magazine that when it hit my mailbox, I’d read it from cover to cover the first day I got it. I’ve been a subscriber for, she’s probably 30 years now and it’s just a special magazine. 

Chris Jerard (30:24): 

Yeah, I mean I felt the same way. Why did I decide to join up with Robin? That was significant. All of those brands were Warren Miller, all really storied, and I was very familiar with them as brands and the opposite and downs of some of those brands. But the opportunity to be part of, in some ways, refreshing some of those brands, very much what we were doing at Rome and certainly what we did at Free Skier was very youth culture based, always fresh in that way. What’s the newest thing? 

Joshua Ross (31:03): 

So what is it like going from, I mean, you’ve been an entrepreneur your entire life and now you work for a company, dare I say it, as an employee? How’s that transition? 

Chris Jerard (31:15): 

Thanks for reminding me, Josh. Yeah, I mean it is a transition just frankly, especially going from being a founder, right? To yes, being an employee. But it goes back again to those early conversations with Robin and he as a founder being someone that I really admire for his experience of founding something based on his passion, selling that to a major, major brand, then that brand going public. So really the experience, wow, there’s something that can be learned here for sure inside of outside, I am an intrapreneur, so I’m fortunate that because of that trust I think and that mutual understanding with Robin that he continues to create opportunities within the company where I am kind of running a startup within the startup. And there’s a skillset that goes with that operating understanding, a p and l marketing product that we sometimes need, not on the macro for every aspect of the business. 

(32:53): 

His job is the CEO, and there are others that are in leadership that do that for the 400 person company. But when my experience in three years there has been, when we are starting something new or crazy, I seem to be the person who’s doing it. And that’s exciting. I mean, I love that. I mean it is like there are aspects of it that are very much like being a founder or an entrepreneur within what we’re doing at outside. And then there are certainly aspects being on the executive team of a larger company, a much bigger company that are actually new experiences for me on more of a corporate level. And that’s really good for me too. I’ve realized that it’s one thing that I’ve realized, in fact, one lesson that could be good for any entrepreneur is as a founder, oftentimes you manage by authority. You are the founder. 

Joshua Ross (33:53): 

Yeah, absolutely. 

Chris Jerard (33:54): 

People listen to you 

(33:56): 

Whether they want to or not sometimes. And when you’re in a larger organization, you really have to manage by impact because you’re not actually the boss. And like I said, that is actually sometimes, and I am sure any founder out there that’s challenging and it’s why a lot of people say, no, I’ll never work for somebody else. And it can be challenging. You have to navigate. You can’t just say we’re doing it. You have to sort of navigate the hallways of making a case and having impact so that doors open and permissions happen and budgets open and that kind of thing. And that’s more time consuming sometimes. But it’s actually really good I think on a managerial kind of career level. 

Joshua Ross (34:52): 

So some of the times you just want to say, let’s go full send. You got to reel it back a little bit and go through the proper channels. 

Chris Jerard (35:00): 

Yeah, you have to go secure the permission ultimately, right? And you’re almost pitching, it’s back to that experience that I had finding funding. Oftentimes that’s kind of what it is. You’re finding funding or permission or resources, and it’s not always capital. It could just be resources. It could be I need design resources. And since you’re not fully in control as you would be in a startup that you’re the founder of where you say, oh, we need design. Let’s hire a designer. We’ll figure it out. I’m in control of the p and l inside of a larger company. Sometimes it’s just not that easy. You have to navigate other priorities within the organization. And again, that can be really frustrating, but it’s actually, I think very good. It’s an exercise in patience sometimes, which is good 

Joshua Ross (36:02): 

Audience, I just want you to know that Chris is smiling as he’s talking about this. So one of the things that you’re in charge of is the outside festival, which I think is an amazing new venture for outside, and it’s something that has created a lot of community here in the front range. Last year was year one. What I want to first understand was is what’s the vision and purpose behind this festival? 

Chris Jerard (36:31): 

Yeah, great question. It is, I think to fill a void that exists right now within specifically the outdoor community I in where is the one place that we all agree that we meet once a year? The annual definitive gathering of the outdoor industry and the outdoor enthusiast and the outdoor curious that is the vision is you can kind of work back from there that it’s a global understanding that this is where you go and that you go. If you are in the business, you go if you want to be in the business, you go, if you’re looking for a job, you go, if you have a job and you want to learn, you go. If you want to be entertained, you go with your family and your friends because you want to feel good and joy in the outdoors and connected to other human beings and listen to some great music. 

(37:38): 

And we don’t really have that in the outdoor business at this stage. And I’ve just, I realized over the years how much events have actually carved in a way my pathway meeting people over the years through the ski industry, through the outdoor business south by Southwest, going to these events that were gatherings and thought leadership and meeting people. And oftentimes you can bring whatever happened after because of that meeting, you can go back and you can say, oh, that’s right. We met at SIA, we met at, or we met at South by Southwest, we met at the X Games, whatever. Those are, in my experience, all real and relevant. So feeling that there wasn’t truly that in the outdoor business. And then going back to Robin, Robin having the same idea when we went through the conversation around the acquisition, that was one of the things that he said, I think we could do this south by Southwest kind of thing for the outdoors and light bulb, just, yes, let’s table that. 

(38:46): 

We’ll get back to it. But if you decide to do that, I agree. I think there’s real opportunity. And then looking at Denver and Colorado, an outdoor brand, a global outdoor brand, being Colorado and looking at the map of Denver when the last couple of times I was in Austin for South by and saying, wow, we have all the same, we have 16 theaters in this mile and a half. We have Coors Field, empower Red Rocks, multiple parks. We have the geography to do a large scale event that could draw people from all over the world and show off what we have here in Colorado, bring the industry together and see new innovation, new connections come out of that. So that’s always been my vision. That combined with Robin, combined with Connor Hall at the office of Outdoor at Recreation here, the governor, the mayor, others seeing that same idea and wanting to do it here really kind of brought the idea to the forefront almost two and a half years ago now, and that we’re starting to see it happen. 

Joshua Ross (40:05): 

So running this Multiday Festival, huge lift, many moving parts, scheduling, personalities, costs. So what did you learn from putting on the first outside festival kind of big challenges and also highlights? 

Chris Jerard (40:21): 

Yeah, I think one of the things that, and I just spent some time with my friend Chase Jarvis, who just put out this book called Never Play It Safe. And that idea, one of the things that’s been reiterated by this experience and that I learned is you have to take big swings. You have to be unafraid to take big swings. You have to, there’s some faith that goes into, if you’ve got the right team, you’ve done the math. It’s possible. I’m not saying the emperor has no clothes like magical thinking. You’ve worked it out, you’ve penciled it out. Some things have to go right, but they can go right? And if they do, it can be amazing. And this whole experience has reinvigorated me around vision and putting a lot of disparate parts together to make something cohesive and given me some confidence. Again, in that idea, it has definitely reiterated for me that the number one thing to do anything hard is team. 

(41:32): 

The team, all those folks I mentioned, the civic aspects, the public, private, nonprofit, all of the people around that, plus the team at outside who absolutely went to the mat to make it happen, none of it would’ve been possible. All the things you said, like so many moving parts in an event. Oftentimes, in fact, I think a lot of entrepreneurs will be like, juice not worth the squeeze, man, unless you’re measuring it in smiles. Very expensive to do also. But team, it’s all about assembling a team that believes in what you’re doing. Because when you’re doing something like that, especially for the first time, and I would say for the second time now too, you’re going to run into really some hard days. And if you don’t have that purpose behind it, then it’s impossible. People will not, they’ll dig in and say, okay, the cost is not worth it. 

(42:39): 

The personal cost, my time on phone calls at 1130 at night with people who also have families trying to get this thing over the line. People putting that much effort into it. And by the way, not getting paid anymore to do that, right? They’re doing it because they believe in the work. And that’s been one of the biggest professional takeaways. There are a lot of other takeaways from a community perspective, but on the building of the team to see people really rally around an idea and a vision has brought that back to bear for me. How important 

Joshua Ross (43:17): 

It’s, were you able to enjoy the moment? Were you able to during the festival as you’re walking across the grounds and looking around and being like, we did this? 

Chris Jerard (43:29): 

I think so. I think it was both sides of it. I guess. It is funny because a coworker, after the first day, we had projected six to 10,000 people, and so 18,000 people ended up coming. And you could feel that from a like, wow, people actually turned up. And you’re kind of, especially on the first year, there’s a little bit of, is anyone actually going to show up? We know we’ve sold some tickets, but what’s going to happen? And so when those gates open and people started flowing in, that was really fun. And it was really fun. It was humbling. I think it was humbling for a lot of people to say, wow, the music was great, the vibe was great. All the things that we had envisioned were coming to light. And a coworker said to me after day one, are you, same question. 

(44:27): 

Are you so happy? And as a business, I wasn’t yet because we were only halfway through, there were still targets we needed to hit and said, talk to me like Monday. And so even in the midst when you’re operating, there is always that part of you that’s like, yes, it’s cool, it’s working from a cultural perspective, but is it working from a business perspective? And that I’m obsessed with that I can’t. So I enjoyed it, but I was still working on it and I was still a little bit nervous about is it going to pencil out? Because in the end, if you make it, and it’s a big success from the outside perspective, really though the p and l still matters. And so do you hit your targets? And that made it so I wasn’t quite able to fully appreciate every moment, but at the very end when Fleet Foxes were kind of closing it down and there was a lot of joy, and actually even I think about it now and know you’re reminding me, I think there were tears people, it was an outpouring of, it was relief and excitement and joy, and we worked so hard to bring it together. 

(45:53): 

And you’re kind of like, oh man, it worked. That is awesome. 

Joshua Ross (45:58): 

So the outside festival’s happening again, May 31st through June 1st year two, the music lineup was just announced. So what can attendees look forward to this year? What’s new? What’s staying the same? Give us a little inside, little inside peak. 

Chris Jerard (46:14): 

Yeah, happy to. Well, the big thing is the music. Bigger, bigger bands just such high quality music. Krung bin, Sylvan Asso, Waxahatchee, Neil Francis husbands Haslet, trampled by Turtles. Lord Huron, who am I forgetting? A bunch of others. But all of these bands are bands that can sell out Red Rocks altogether for two days. I mean it’s like 20 hours of music. So that’s the undercurrent. And the bands have been selected based on their vibe, based on the feeling cr bin as probably our biggest headliner. Their music is just, I would say it’s like joy personified. It feels good. So that is the big draw is the music. And then beyond that, you’ve got about 15 acres between Civic Center Park and Lincoln Veterans Memorial Park. We’re closing down Broadway, so the footprint itself will expand by about 40%. We are in Denver Public library this year with the film festival and the ideas sort of forum, which is speakers and panels. 

(47:35): 

We’re in Denver Art Museum again, so we’ve got a film festival, we’ve got an ideas programming with all of these speakers. There’ll be climbing, there’ll be yoga, there’ll be coal plunges, there’ll be a dog expo. Again, lots of really exciting things coming down the pipe. And we’ve got a title sponsor, REI and Capital One, which came in, it was kind of proof from year one that we’ve got some really great, great support this year going into year two. And its expansion growth is part of what we’re bringing this year, and we expect there to be again, like 50% more people, like 25,000 or so folks in the park. 

Joshua Ross (48:23): 

Alright, so final question. When you’re not working, what do you do for fun? How do you relax? How do you recharge? 

Chris Jerard (48:30): 

Yeah, I obviously love being outdoors. That’s kind of my go-to. I hike this peak in Boulder every week called Bear Peak, mostly with my brother, my younger brother. But I invite people all the time. 

Joshua Ross (48:48): 

Wait time out, you hike that every 

Chris Jerard (48:50): 

Week? I try to once a week. 

Joshua Ross (48:52): 

Alright, so just audience out there, what is it, about 3000 feet of vertical and at what, three or four miles? 

Chris Jerard (48:59): 

It’s about a five mile round trip. So it’s like two and a half miles from my house to the top, which is, and the vert is more the thing it’s kind of straight up for, 

Joshua Ross (49:10): 

But some of it from your house I’m guessing is that flat part. So I mean that vert is real. 

Chris Jerard (49:15): 

Oh yeah, 

Joshua Ross (49:16): 

Yeah. And you get up to a saddle the first time I did it and you think you’re done. And my daughter’s like, no, we’re going to hang a left right here and go up that. 

Chris Jerard (49:23): 

That’s right. 

Joshua Ross (49:24): 

Okay. 

Chris Jerard (49:25): 

Yeah, no, I love it. Kind of defrags for the week and I get to connect with my brother or other friends. We get up above it. We try to go for sunrise, so really early. So that’s something I love to do. If I could do anything, I would go surfing. I mean, it’s funny, we’re landlocked here. I love to ski still, but I’ve done a lot of that in my life and I’m still learning how to surf and I just love being, I grew up near the ocean, I miss it. And just for my birthday, I just went to Mexico for a week with a bunch of friends and that’s probably about as perfect as it gets for me to be near the ocean, hanging out with my friends and my family and get to go surfing a couple times a day. See the sunrise, see the sunset, be immersed in the outdoors. That is my happy place for sure. I do love going to dinner with friends too, but if I could choose to do anything, I think I want to go 

Joshua Ross (50:27): 

Surfing. Alright, I love that. I love that answer. Well, Chris, thanks for joining us today and making me a little bit smarter. I appreciate it. 

Chris Jerard (50:38): 

Oh, thank you. I don’t know about that, but happy to have the conversation with you. Thank you, Josh. 

Joshua Ross (50:45): 

The entrepreneurship at DU podcast was recorded in Marjorie Reed Hall on the University of Denver campus. You can find us on Instagram at du Entrepreneur on Twitter, X at DU entrepreneur, and on Facebook at entrepreneurship at DU u. This episode was engineered, edited, and produced by Sophia Holt. Entrepreneurship at DU is part of the Daniels College of Business, which has its own podcast. Check out Voices of Experience wherever you get your podcasts.