Andrew Dickson & Aaron James: Self-Employed Mountaineers

By Alixandra Rutnik on May 10, 2021

Freelancing duo shares a mountain of experience via podacst


Creative duo Andrew Dickson and Aaron James knew that they had accumulated a mountain of knowledge about freelancing over the years, and they wanted a way to share it with the world, especially those who are just starting down paths that they've already traversed. So they created Mt. Freelance, just two freelance pros sharing what they know. Most recently, they decided to expand their business and have stepped into podcasting with The Mt. Freelance Podcast — their new initiative to grow and support the freelance community.

Each episode highlights a specific freelancer’s story that you don’t want to miss! So far Lisa Prince, Marcus Smith, Sue Kim, and Aaron Ruell have been featured, with Kathy Hepinstall’s episode being debuted this week.

We talked to Andrew and Aaron all about Mt. Freelance, their unique stories, and what to expect on their new podcast– The Mt. Freelance Podcast.


How long was it after you guys met before you started Mt. Freelance together?

Aaron: We first met years ago when I was making some ads for The Northwest Music Fest. I had this idea it would be funny to have a group of moms come to a focus group and react to the bands who were playing the festival that year solely based on the band's name, without hearing their music. I cast Andrew to run the focus group.

Andrew: I remember the Butthole Surfers getting a powerful reaction. So we knew of each other, but it wasn’t until we were partnered together by BPB on a pitch that we worked together and really got to know each other. The idea of creating Mt. Freelance came up during those two weeks together, mostly over lunch. We realized we both were being asked out for coffee and beer by folks new to freelance to discuss how much we have learned over the years. Aaron said we should put it all in a course, so we set out to create it as soon as the job wrapped up. One of the biggest questions at first was should we call it Freelance Mountain or Mt. Freelance.

Aaron: It took us a good year of work to figure out what to cover, and organize our ideas, and then of course actually script, film, and edit the course. Then we had to create the website and figure out the member community component of it. We were both and still are freelancers working for brands and agencies, so it was work real hard on Mt. Freelance, get busy on client work, then come back to the course when we were both free.

Andrew: Then we had to market it and promote it. You’d think having worked for big brands that would have been easy, but those are established brands usually with massive audiences. So even with a supportive network and our experience it took a tremendous amount of work to get the word out between press, emails, social, and just hustling.

Aaron: As far as why we created it, for me, it was about passing along what I know. I was freelancing for a few years before some senior freelancer creatives took me under their wing and helped me make my book better, encouraged me to charge more, and gave me tips on how to work effectively as a freelancer. This podcast was our chance to pass on what we’ve learned and make it accessible. We’re pretty much an open book on all things freelance, including rate. It was also a chance to work on our own brand instead of only working on other bands.

You have been doing freelance work for 20+ years combined, so what have been the best benefits and the most difficult challenges about being a freelancer?

Andrew: I love freelance because I get to see my family five times as much as when I worked full-time at W+K. Don’t get me wrong, there were a lot of great things about working there, but control over my schedule wasn’t one of them. As a freelancer I am fortunate to have a lot of job opportunities. I get to choose jobs where I get to work on a great project, get to work with great people, or have control over my schedule. When I’m lucky, I get all three.

"I love freelance because I get to see my family five times as much as when I worked full-time at W+K."

Aaron: I love freelance because it gives me the chance to work hard and then take a few weeks or even months off to travel or work on my own businesses. I also co-created another business called the Hitting Vault and I co-own the soccer magazine Howler. So I love the flexibility of freelance.

Andrew: Legendary freelance copywriter Kathy Hepinstall is one of our guests on the Mt. Freelance podcast. She talks about how freelancing allows you to charge for your value versus your time. That idea resinates with me, and it’s one of the reasons I love charging a project fee. If I can come up with an idea or a solution in an hour that a client hasn’t been able to crack for a few weeks, I want to be able to charge more than an hour’s time and freelance affords that.

"Legendary freelance copywriter Kathy Hepinstall is one of our guests on the Mt. Freelance podcast. She talks about how freelancing allows you to charge for your value versus your time."

Aaron: The challenge of freelance is not having coworkers. That’s a big reason why we created a members-only Facebook group for Mt. Freelance, to give people a chance to get to know each other and help each other out, and help each other find excellent gigs. Since the pandemic, we’ve been doing monthly Zoom meet-ups with our members to check in with each other and share ideas and tactics.

Andrew: The hardest part about freelancing for me is when client work goes cold. I might go from turning down multiple jobs because I’m too busy to suddenly having no work for a few weeks. One of the things we encourage our members to do is work on personal projects during slow times, which is advice I take myself. While I used to stress out about it, now I throw myself into my own work and trust paying work will pick up again.

What are both of your "how I fell into advertising" stories?

Mt. Freelance is a membership-based community with an online freelance course, and now it has a podcast for all to hear, so what made you feel that the world needed another podcast, and what made you the right people to do it?

Andrew: Honestly, part of it was just having the opportunity. Eric Stolberg at Digital One, who we’ve both worked with for years, approached us about doing a podcast as a way for him and his team to showcase how badass of a podcast they can make. When you listen to it, you will hear that it is impeccably recorded, mixed, and produced. A lot of what our guests talk about applies to other freelancers but anyone with a creative career, especially business owners. It’s been great for everyone involved to hear the interviews and get ideas.

Aaron: We have a wide network, having done this for so long and worked at so many different places, so this was a chance to invite some of the inspiring people we know and hear their stories. There’s a sharp focus to it, because we’re interviewing them through the lens of being a freelance creative. It’s a little bit like How I Built This, but our guests have built these super exciting careers instead of a big company.

Andrew: Process-wise, we did most of the interviews remote, but we bought three of the same microphone. Aaron and I would have ours, and then we’d mail the third to our guest, which helped keep the audio quality superb. In a funny way, it was almost more intimate than being in the studio together, and it cut down on flight costs.

How are you hoping The Mt. Freelance Podcast will grow and encourage the freelancing community?

Aaron: I think people are going to tune in and get inspired. Our first guest Lisa Prince quit her job as a global group strategy director at W+K to intentionally spend a year of doing nothing, which led to creating her own company, the School of Ideas.

Marcus Smith spent a season photographing a high school basketball team all on his own, which opened the doors to a career shooting for Kobe and LeBron for clients like ESPN, Nike, and Brand Jordan.

Sue Kim quit her job to make a passion project that turned into the documentary “The Speed Cubers,” which was short-listed for an Oscar.

Andrew: I think anyone in the creative industry who listens will get some actionable ideas from the episodes and get the theme song stuck in their head– apologies in advance. A shout out to Tristan Schmunk for making it.

Season 1 will be 12 episodes, with a new episode available to stream every Thursday. What do you want people to know about this podcast?

Aaron: You can listen anywhere you listen to podcasts. Apple, Spotify, or of course, our website

"We spent upwards of two hours with each guest, getting stories about their journey and then asking a lot of practical questions about charging and how to juggle client work with personal projects."

Andrew: I think our guests make it unique. We spent upwards of two hours with each guest, getting stories about their journey and then asking a lot of practical questions about charging and how to juggle client work with personal projects. The episodes are cut down, so you’re getting the really good stuff.

You guys are freelance pros, so how do you see the freelance community evolving in the future?

Aaron: I think it’s a pretty great time to freelance. As clients move towards project-based work away from the agency of record relationships, having a reliable stable of freelance talent is becoming a business model a lot of new studios, agencies, and collectives are using.

"As clients move towards project-based work away from the agency of record relationships, having a reliable stable of freelance talent is becoming a business model a lot of new studios, agencies, and collectives are using."

Andrew: What we’re hoping to see and hoping to be a part of is freelance feeling less like you are all alone, competing with other freelancers for a job, and more of an actual supportive community. We have some old W+K friends that threw a Holiday party for freelancers for years. That spirit is precisely why we created Mt. Freelance.

"What we’re hoping to see and hoping to be a part of is freelance feeling less like you are all alone, competing with other freelancers for a job, and more of an actual supportive community."

MT. FREELANCE


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