Career Crashers: Forging a Path from Ski Pro to Marketing Pro with Andrew Flynn

Andrew Flynn is a growth marketing advisor with a fascinating career crash story, going from pro skier to a thriving marketing career.

Andrew Flynn is a growth marketing advisor with a fascinating career crash story, going from pro skier to a thriving marketing career.

Don’t be afraid to fall. Get good at falling. Because if you can get good at falling, you can try so many more things and learn so much faster than anybody else. 

Isaac and Andrew break down Andrew’s journey and the lessons he learned along the way, covering how Andrew got his start building websites to how he prioritizes learning now that he is running his own marketing company.

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Show notes

  • Becoming a professional “ski bum” by avoiding the normal path (college -> job).
  • Building websites for companies without being asked and turning into a bike shop owner.
  • How Andrew got hired at is first real marketing job by pitching himself.
  • Going on to an executive position, still without ever having gone to college.
  • Why Andrew eventually went back to freelancing.
  • How to prioritize learning by treating yourself as one of your clients.
  • Advice to reduce anxiety: getting good at falling.

Connect with Andrew

Full Transcript:

Isaac
Welcome to Career Crashers, where we tell the stories of those who are not content to wait around following rules and hoping for good things to happen. Great careers are found. They’re forged.

It’s time to crash the party.

On this episode of Career Crashers, I’m joined by Andrew Flynn, who is a marketing guru. And Andrew has done some marketing work with us at Crash, so I can vouch for his skills. But I just learned even after he’d been working, doing some marketing for us for a couple months, I just found out that he has a pretty awesome career crash story. Andrew was a ski bum, I shouldn’t say ski bum because he was paid to ski.

Andrew
I was a bum.

Isaac
A paid ski bum.

Andrew
Yeah, yeah.

Isaac
And in parlayed that into a marketing career, skip skipped out on the college route, and is now making a living in marketing, doing all kinds of all kinds of stuff for everything from fortune 500 companies to small startups and everything in between.

So I don’t even know where to start. Let’s start with the skiing. That was this like your passion and what you put all your focus and energy into in terms of like career?

Andrew
Um, I don’t know that I ever thought about it like a career thing of more than I just wanted to. Just wanted to go ski. Like that was like I didn’t even want to make any money skiing. In fact, like, I just wanted to ski. Like I just really just everyday just wonder wake up and wonder where I’m going to go ski today.

Isaac
And where did you Where did you grow up?

Andrew
I grew up in upstate New York. So I had a small mountain near me called Willard mountain but my local mountains would have been Stratton mountain snow, some of the bigger mountains in Vermont. So I’m basically a vermonter. I’d say New York because people think it makes me sound official and business-y, but.

Isaac
In business, you’re from New York in pleasure, you’re from Vermont.

Andrew
My mo explanation of me much like my lifestyle.

Isaac
So it’s really so it’s really like you just wanted to ski as much as possible. You weren’t really thinking long term or planning long term.

Andrew
Not at all, not at all. It I wanted to ski It was fun, is just very free. I don’t know, I grew up pretty easy to It’s not like I had a whole lot of stressors. So my dad was CTO and just was afforded a pretty nice lifestyle. So to me skiing was just like a normal thing to just wait just keep doing this.

And at the same time also, I’m actually not when I think about it, I’m not sure how much of it was I wanted to keep skiing versus I wanted to just avoid the normal path of like, I’m going to go to college, I’m going to do this next thing kinda kind of get off on flipping the bird of that whole thing and just doing my own thing and seeing what how I can make a go of it.

Isaac
So out of high school did you face like pressure from parents and stuff to go to college and do something and what was your what do you do instead? You skied in you How did you end up getting sponsored for skiing?

Andrew
A little bit but it was really more. I mean, my my dad was a college dropout and he ended up becoming a CTO. He dropped out to make guitars so he was like one of the call that a luthier so like that’s like a way bomb your thing than anything I was doing.

So I think my parents were like my one of the things my dad would say was he thought there was going to be a 5050 shot and whether I was going to be completely loaded and really successful professionally or in prison.

Isaac
My son will either be sleeping on a park bench or he’ll be like a billionaire. There doesn’t seem to be a middle.

Andrew
And his attitude was that’s up to me to figure out like it’s on the the individual the if you want to get the drive you got to figure it out yourself. Like just get out there in the world experience that you’re going to learn more going through things naturally than you would if you’re just walking on somebody else’s path your your entire life that never was interesting to me.

You know, it’s funny when he asked me to do this a couple days ago, I was thinking he’s get I was thinking like through my career and stuff of like how things transition from one thing to another. And I completely forgotten that I owned a bike shop at one point in time.

And I was like, oh, Isaac’s gonna get a kick out of this and like this guy accidentally owned a bike shop.

Isaac
Whoa, okay, so tell us this story. So where does that fit into the sequence?

Andrew
So skiing wasn’t good enough at skiing, actually make a bunch of money, started making websites to anybody that would listen to me. Some people wouldn’t even pay me as just like, oh, maybe they’ll pay me if I do it, they’ll feel guilty and then pay me said make websites.

Eventually I made a website for a guy that owned a bike shop. And the guy that owns the bike shop with one of the people in the cohort of no money. So he just gave me a portion of his bike shops. And I was like, I guess I own a bike shop.

But it’s been, I think, just in general, in my career, it’s been this thing. And this is something where I really think it came from skiing was, because the skiing I did this, the more we think of like Shaun White snowboarding’s type stuff of like trade Park, you’re constantly crashing, but you’d be working for like weeks on a trick, and just crashing, crashing, crashing, and then you get it, and you just get this flow about it.

So I think my life has kind of been that flow of like, I’m just going from one thing to the next. And like, it always ends up a little bit better. But it’s because consciously trying things, learning and iterating, just again, and again, and again and again.

Isaac
That’s so I’ve got to two lines of the narrative here that I want to pursue. I’m trying to decide which one to do first. Well, with this bike shop, so he gave you like, in exchange for you making a website, the guy gave you like part ownership, like you have equity in the bikes, yes. It listed on Robin Hood, and then you can go cash out, you know?

Andrew
It was an early, it was early in the days of like e commerce, where Shopify and those things didn’t exist. So you actually had to know a little bit of code to make an e commerce site. And I had made him an e commerce site, which was really rare in the bike shop world, because a lot of like mom and pops that just don’t get that stuff.

So then I given him a bill that was like, $30,000, or something. And he was like, well, the bike shops only worth like, 60. Like, do you just want half of it? And I was like, I think he expects you to say no, but I said yes. And then I just like I moved my design stuff into the bike shop, and just started doing web design out of there.

Isaac
Wow.

Andrew
Yeah.

Isaac
So when as a half owner of the shop, like, did you did you take in? Did you get half the profits? If there were any? Or did you sell that?

Andrew
It like very little, very little profits. It was unable to pay me for my website. In hindsight, I should have seen that.

Isaac
Well, but you were a tycoon, you know, you got to be a business owner. That’s, that’s crazy. So I want to dig it on this website thing. This is really nifty.

So you had a few, you had a few sponsors, you mentioned skiing, and that’s when we talked the other day, you said that’s who you first started pitching marketing services to some of the companies who were sponsoring you. What gave you the idea to say, oh, how about I like, go build a website for this company and see if they’ll pay me for it?

Andrew
It just, it was a skill that I just had. So I guess, of, you know, growing up with my dad, being a CTO, there were always computers in the house. So I remember, you know, back in like, I think it was like 1996 nba.com launched. And it had all these awesome commercials and stuff.

And young budding 10 year old Andrew Flynn was, at that point, learning how to build himself some like geo cities, sites and stuff like that. So it was like this skill that I just developed at home, you know, between playing roller coaster tycoon and whatever else. Whatever else a 10 year old did.

So it’s just a skill that I had, that I knew there was value there that it was just a factor of that being in my family that I could apply it to to other things. But as far as like thinking out, you know, 15 years from then was I going to be some like, hyper successful consultant doing this stuff. I was not thinking that far out.

Isaac
Yeah. So that’s what I love about your story. Like, it wasn’t like a master plan. It was like, keep, keep doing things that are interesting. You keep tinkering, experimenting, learning things, and then just don’t be afraid to go make a pitch make an offer to somebody, Hey, can I build a website for hey, here’s something I can do looks like they need it. Why don’t I just ask why don’t I just see it?

So you said you you would you would build the website first and then basically offer to give it to them for money or even give it to them for free? What made you decide to go about it that way? Instead of sort of asking them for permission or asking them ahead of time? Well, are you willing to have me build a website for you?

Andrew
I think at the time I didn’t even have like the confidence to charge people. It’s kind of a weird thing to say but like I wasn’t, I didn’t in hindsight, I see the value to everything that I did. But then it wasn’t seeing like an immense amount of value.

So it was almost like I was like embarrassed to say up front and now I feel totally different and be like, hey, guess what? Isaac, we’re doing a six month contract and you got to pay it all up front, but a year, whatever. like it’d be more forceful about it. But back then I was like, nervous and not necessarily sure my skill set and all those things. And with timing came, but back then I was, I didn’t even want to charge for things.

Isaac
When did you realize, Hey, I can charge I should charge, you get that confidence. Because asking a bike shop to pay you 30 grand, that seems like a really big leap from, hey, here’s a website you can have and maybe pay me, you know, how did that? How did that progress?

Did you just start to realize, hey, people really liked this, this is valuable? Or, you know, did somebody advise you on that?

Andrew
Um, I wouldn’t say advisement so much as like, my family telling me that like, Hey, you have to pay your own cell phone bill now. Hey, that car payment, that’s yours now, buddy. Like, that sort of thing.

And then me being like, okay, maybe I should charge these people like, this is a thing where like the, some of the some of the societal norms, I think are a good forcing function in that way of, you’ve got to go out on your own.

And I think the, if I had any regrets, it’s that I didn’t push for some of that stuff earlier. Because I could have, you know, accelerated things another three, four years in my life. So that would be a tip I’d give people is just go for it.

Isaac
When would you say? So you’re doing these kind of websites and building on and you start charging for making some money. Was there a point at which you’re like, you know, oh, I’m a professional marketer? Or did you go into? Because you did marketing? You haven’t always been a freelancer? You did it in house? Correct? at some point?

What was that like transitioning from, you know, a kid building websites and making little money charging for them to getting hired on as a marketer without a degree?

Andrew
Yeah. Um, it so the getting hiring part there getting hired part was always relatively easy, I’d say of like, is just the same thing. If you’re, you’re going in, you’re showing the skills, you’ve got probably showing a few things that you noticed about their site in my example, or their products or whatever you’re, you’re pitching yourself for.

I don’t think I got asked about college degree until I was interviewing for an executive position where it was like a checkbox that I had to check yes or no on. And they just assumed that I had one up to that point. And I was like, No, I wanted to ski. Why would I have a degree? Like, why would I want that?

But it was never, like, it just never got brought up. And I think because I didn’t go I just didn’t have any preconceived notions that it should be brought up. It’s just, I would show up for an interview show what skills I had and get hired.

Isaac
How late in your career was that? When you were when you were going for this executive position where you had to check the check the box?

Andrew
That would have been 2018? So 15 years in I guess at that point?

Isaac
Yeah. And did anybody say anything about it, when they when they saw that? You didn’t have a degree?

Andrew
Yeah, they were like a little bit put off about it. I’m like, you guys offered me the position. Like this wasn’t at that point. It wasn’t even one that I was interviewing for. It was like an executive team that was placing the position. And they were like, surprised.

I’m like, Well, sorry. Do you want me to do the job or not? And they put me right through and nobody had a problem with that.

Isaac
Yeah.

Isn’t that funny how it’s like, like, everyone sort of just accepts that there’s something useful and valuable that this degree is doing on the job market. Even the people who don’t actually care about it, they think that they should care about and there’s always that minute, we’re like, oh, you don’t have a degree like, am I supposed to do something? Am I supposed to be like, weirded out by that? Should there be a problem?

And it’s like, when you step back, think about it. You’ve been doing marketing for 15 years, they identified you as someone you want, they wanted you in this role based on your work to think that what you were doing 15 years ago, sitting in a classroom somewhere should bear some relevance to this like it’s just an absurd notion.

But it’s it’s just weird that you see these little funny little examples like that, that stick around. I you know, I don’t ever see them really being major obstacles if you’re, if you’re doing good work. And, you know, you’re out there but they they create just really funny like, reveals these, like implicit ideas and expectations, you know?

Andrew
Yeah, yeah, everybody’s looking for a filter. And it’s, it’s definitely a big filter, but it’s one that I feel like you can just work yourself right through if you if, if you want to.

Isaac
Yes. I had a degree and I remember being like, well nobody even asks, and no one seems to care, at all. And if I just listed it on my resume, and I didn’t actually have one, I don’t think anybody would ever know that there’d be no difference. Like nobody’s checking up on this stuff.

Nobody’s like, oh, you’re claiming to have a degree from Western Michigan University. We better verify that because that carries a lot of clout, right? It’s like, it’s like it just was useless to me.

So what you did you did you find when you went into, you know, working in house, in marketing. Did you find like you wanted more freedom, I guess what brought you to it? What made you decide to go back to freelancing?

Andrew
Yeah, yeah, I’m definitely not a, I’m not a long term employable person. Except for by myself. It Yeah, when I was when I was younger, I didn’t have the confidence to charge now I’ve got the confidence to charge and the experience and all that. So it’s a it’s a thing where I can run a really sustainable business for me and my family off it.

I like a lot. I like a lot of change. And change in companies is sometimes good change in large companies can sometimes be like really bad of like, companies need some consistency to them for really large companies to have everybody show up to work and be comfortable. That showing up to work can be uncomfortable, isn’t comfortable for me.

Yeah, I like the change. I like the early stage startups that don’t really know where they are yet. And that discovery phase, I like the I like doing the tricks that people haven’t done yet. I didn’t get as many opportunities to do that internal at companies as I do external.

And I think as a as an external person, too. Sometimes people are willing to let you go a little bit further than they are when when you’re internal. And that’s a that’s a fun place for me to be.

Isaac
On your path. And it sounds like this. There’s a theme of like, not over planning, not thinking too far ahead. Kind of like, hey, let’s let’s roll with what’s going right now let’s take the opportunities as they come, let’s not be afraid to go at them. But you know, kind of a roll with the punches or a sort of open ended approach.

Have there been times where that has been really stressful for you? Where you’re like, you know, okay, I mean, even just as a freelancer, like, I don’t know, six months from now, when my current contracts are up, I don’t know where my money is coming from, like, how do you deal with that? That aspect of your your lifestyle?

Andrew
Yeah, it It definitely is like it’s a it’s a thing where you know, some mornings you’ll wake up and everybody has certain levels of stress. But some mornings, I’ll wake up and be like, Oh, shit, I don’t know where money’s coming from. And it’s, I’ve got enough saved now where it’s not as big of a deal. But it’s still I’d be lying if I said it wasn’t a stressor.

But then at the same time, I’ve sort of just I’ve gotten enough of a rhythm now where I’ve figured out that every time I let go of a rope, there’s another rope there. And I don’t know if that’s always going to be the case. But it’s been the case, since I got out of high school, I might as well keep rolling with it. And eventually there won’t be a rope there. And hopefully, that’s my retirement.

Yeah, that’s, that’s how I I think about it. The same time, I don’t really I mean, again, I understand not everybody’s in the same type of situation as me like growing up pretty fortunate, that type of thing. But yeah, it’s not a big stressor for me, but it’s definitely there’s some mornings you wake up and I got a wife, two kids, like, you’re you. I’m the provider. So there’s a there’s a level of stress there for sure.

Isaac
Do you ever have difficulty because it seems like, you know, you, you were self taught on your sort of initial skill set building these websites and things and you’ve been, you know, I would guess largely self taught or maybe you’ve learned out of necessity in response to getting a job or a gig that you needed to learn something new for? How do you how do you balance?

Do you ever get to the point where like, you could keep taking jobs where you’re basically doing the same thing over and over again? And then like, you gotta you got to make sure that you’re learning new stuff, somehow. Do you know what I mean? Like, Do you ever get in a spot where like, Okay, I need to keep learning otherwise, I’m going to get behind, especially in a game like marketing. How do you make sure you’re maintaining a level of, you know, leveling up and learning new things?

Andrew
Yeah, I basically treat myself as one of my clients, is how I how I think about it. So like, if I had the capacity to work with five clients, I’d only work with four because one of the clients has got to be me as an advocate for myself, basically. Because if I’m not, I’m going to be irrelevant in a year or two, maybe even six months.

Sometimes it’ll go where I’ll go like six months without a Facebook ads client, and then I’ll sign in to that interface and is totally different. Shit, like I’m incompetent. I don’t have I can’t do this professional anymore. But again, it’s just the same rope thing of like you get in there. It’s okay. Like, it’s still the same stuff. Like there’s just, there’s just humans looking at ads, buying things.

Yeah, it changes fast, but also really slowly. But one thing that I’ve been pretty conscious about is always having a time, substantial time for learning set aside, I could definitely, I think make, probably in the short term a lot more money. If I was like, Hey, I’m only taking this boilerplate client and this boilerplate industry. That seems really boring.

It seems really, I don’t want to wake up for that. And like the, you know, we’re like waking up, and like not having money or something seems like it would be something that’s really frightening. The thing that would be way more frightening is like if I woke up, and all of my clients were suddenly in like, the public power industry or something. Like, what have I done? What have I done?

Isaac
I love I love that approach of make yourself one of your clients. And it’s so funny, you said just six months, like, I don’t think you’re exaggerating man in the in the, in the world of marketing. You know, because I remember when I first started Praxis, my first company, like, I was actually like, kind of good at marketing, like not great, but I could I could run Facebook ads when Facebook, Facebook was very young. I could run Facebook ad campaigns, I could do SEO, I could, you know, I could kind of I can do I kind of get to just do it myself.

As soon as I started handing some of that stuff off, literally, like two years goes by, and we lose an employee. And I’m like, I’ll just pick it up and read it myself. I couldn’t do Facebook ads anymore at all. Like it was it was like gone SEO like the game just ratchets up constantly with tools, technologies, whatever. And it’s so far over my head now.

You know, when we brought you on, I was like this is so this feels so embarrassing, because it doesn’t feel like that long ago. And like I understood, basic, you know, marketing stuff. And now I’m like, like, I understand the principles, but the tactics and it’s just, it’s insane how fast that stuff moves. So I really like that, that make yourself a client.

All right, well, give me give me something for our listeners who are because we have a lot of people that listen to podcasts that are like, early career, maybe maybe even pre career or early in their first couple jobs and they’re kind of like, you know, looking for something. Next, they’re getting a little bit of edge they’re getting a little bit restless, with you’re kind of just, you know, go out and shoot your shot and kind of see what comes and and you know, take take the chances.

What would you What would you offer as some, I don’t know, some advice to bring a little bit of to reduce some anxiety and bring a little bit of, you know, playfulness or, or, you know, ability to spot opportunity that you’ve learned from your life?

Andrew
Yeah, I think so thinking about this morning, what I would say and that was when I teach little kids how to ski, one of the first things I would tell them because they’d like look up to me is like this awesome skier guy. I just tell him that I fall more times on this mountain than anybody else here today. And I’m also probably the best skier on this mountain.

But it’s just don’t be afraid to fall, like get good at falling. Because if you can get good at falling, then you can try so many more things and learn so much faster than than anybody else. So that’s my that’s my life tip get good at falling.

Isaac
Are you still out there, falling on the ski slopes?

Andrew
I am now bad at physically falling. Physically falling, my body has physically fallen too many times to count. I get out there a few times a year with with some of my old buddies that are still into it. And then I get to see the the young whippersnappers out there who are all like I was, except way better than me.

Then it’s it’s cool to see the cycle of life and that in that regard. Were there. They’re all out there learning how to fall really well now and I’m assuming we’ll go on to wonderful careers themselves.

Isaac
I love it. Andrew, thanks so much. Do you have like a website or Twitter if anybody wants to check you out? Are you like leave along?

Andrew
@AndrewPFlynn on Twitter. P as in Patrick. Just Yeah, that’s that’s my spot. Twitter.

Isaac
Love it, man. Thanks so much for coming on.

Andrew
Cool. Thanks, Isaac.

Isaac
Like what you hear? Go to crash.co and join the career revolution. Do you want to share your own career crash story? Send it directly to me at isaac@crash.co.

If you’ve got a story you’d like to share, don’t hesitate! Email Joel at Joel [at] Crash [dot] co.

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