7 Lessons From Pomplamoose on Being a Musical Entrepreneur

Posted by Dave Kusek on Jul 2, 2014 02:50 PM
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Photo by Brian J. Geiger

Pomplamoose’s story is one of true music industry success and innovation. The duo creates unique covers and original music using YouTube as their main platform, and also manage individual solo careers. They may not yet be household names, but Jack Conte and Nataly Dawn have made a full-time career for themselves doing what they love – and that’s something all musicians should strive for.

More recently, Jack Conte has used his creativity and entrepreneurial mindset to start a micro-crowdfunding site, Patreon. Building off the idea behind crowdfunding platforms like Kickstarter, Patreon allows fans to support artists for the content they release via recurring payments.

Of course, Jack and Nataly’s story starts way before they had 400,000 subscribers on YouTube, and while you shouldn’t try to replicate their strategies exactly, there are certainly key points you can incorporate into your own music career. Check them out below, then sign up for this free webinar interview with Jack Conte for even more great tips and strategies you can start using right now!

1. Learn and adapt

If you take one point from this article, make sure it’s this one: Learning is the number one best thing you can do for your music career, and the great thing is that you can start right now! If something’s obviously not working for you, figure out why and try something else. Just because Kickstarter worked for Amanda Palmer doesn’t mean you’ll be able to raise $1 million by following her strategy to a tee. In the same way, just because Pomplamoose was able to succeed on YouTube doesn’t mean your career will be affected in the same way.

Pomplamoose, like most musicians out there, started out releasing their originals on Myspace in 2008 with little success. The YouTube revelation began when Jack Conte was sent a video of someone playing acoustic guitar and singing. The music wasn’t spectacular by any means, but the video had 250,000 hits. Realizing that YouTube was the new platform for music and content, he began converting Pomplamoose’s music to video format.

The duo continued learning and adapting even after they were established on YouTube. Pomplamoose’s earlier videos were supposed to be promoting an album of Conte’s, but they quickly found that fans wanted to buy the MP3 versions of the covers instead. In other words, the videos were the products! It was a constantly evolving business model. What songs would get them the most hits? What was the best way to present the music? How much production time did they have to put into the videos? They kept learning and improving and ended up with a business model that was completely unique and tailored to their career.

“Okay, so we'd upload a video to YouTube. Great, we got 5,000 hits. How can we make it better? Okay, let's try doing this kind of song. Okay, that got 10,000 hits. Let's try to make it better. Let's cover Beyonce's 'Single Ladies' and let's release it right after Kanye West makes an ass out of himself at the Grammys. Everybody is searching for Beyonce's 'Single Ladies' — the best music video of the year — and then, using search engine optimization, we mooched off of all that traffic and got 10 million hits on our 'Single Ladies' video.” - Jack Conte (source)

2. Change a thousand things, find one that works

One of Jack Conte’s favorite books is Malcolm Gladwell’s The Tipping Point, and Pomplamoose is a perfect example of some of Gladwell’s concepts in action. If you haven’t already, I’d recommend giving the book a read. It’s a valuable resource for anyone serious about making a career in music.

If you want to be successful, you need to be constantly trying to improve. Just doing the same thing over and over again won’t get you very far. It’s all about making little tweaks to your strategy, finding out which work, making more tweaks, and continuing up from there. Change a thousand things, and if you find one thing that works, that’s awesome! For Pomplamoose, that was doing covers of hugely popular songs on YouTube. It’s a pretty common strategy today, but back in 2008, not many people were on that boat. The key is to make little tweaks and find the right business model for you and your music.

“The thing that I think you should learn from Pomplamoose is not about YouTube. It's not about social media. It's not about music. It's about iterations. It's about trying a million things until something works. That's all we did. We tried a million things and something finally worked, and we were sick and tired. I literally went on three tours where I played – I mean, there were shows I played where the bartender left. There was literally nobody in the room, and it was not a successful thing. It was a total flop, failure, but we just kept trying and trying and trying a million different things, and that's what I hope everybody’s takeaway is.” - Jack Conte (source)

3. Fail often

Failure is usually presented as a bad thing, and with good reason. We’ve all failed before. It’s a terrible feeling, especially when you fail at something you put your heart and soul into. But failure isn’t all bad, and successful musicians like Pomplamoose hit failure more times than they can count.

When you fail, you learn what doesn’t work. You know what not to do as you go forward. It can be really tough to step back, take a good look at your failure, and learn from your mistakes, but that’s exactly what you need to do, and in the end you’ll come out stronger and more successful.

Consider this well-known principle from the financial market: The higher the risk, the higher the profit. In other words, if you take risks, try new things and innovate, you may have a higher chance of failure, but your success could be exponentially bigger than if you had taken the well-trodden, safe route.

“If you’re going along with the status quo you’re probably not going to fail as much. But it also means that you’re not really doing anything that interesting. When you’re really taking risks and pushing boundaries and innovating, failure is just going to happen.” - Jack Conte (source)

4. Don’t go it alone

While we’re on the subject of failure, let’s look at some mistakes Jack and Nataly admit to making along the way. Like every musician out there, they’ve made decisions they now regret, but they’ve learned from them and moved on. They went the 100% DIY route. There were plenty of chances to work with labels and managers, but they turned everyone down.

“I feel like maybe we should have tried to trust some more people and bring more people into the circle and try to build the brand. We did a really good job taking it from zero to 50% and then I think we got paralyzed, and we needed to be better leaders and to have a cabinet of smart people around us to help us take it from 50 to 100, and instead I think we just kind of stopped at 50. Now we're a decent, well-known band. You know, we play 600-person venues and that's awesome, but I think we could have gone much higher had we been better business people.” - Jack Conte (source)

While Pomplamoose is certainly a testament to the validity of the DIY approach, a small team is a valuable resource. That’s not to say that you need to get a major label deal and have top executives working with you. The main point is to have someone else who’s passionate about your music to confer with. Your team could just be a friend who majored in business or marketing, a local booking agent, or even a small indie label.  

5. Start before you’re ready

“If you wait for it to be perfect before you launch, you’ll never launch.” - Jack Conte (source)

Jack and Nataly employ this mantra across every aspect of their career. The fact of the matter is that you could spend weeks or even months getting something perfect, and at that point you will have missed the opportunity. In the same way, you could spend weeks in a state of decision paralysis trying to figure out whether or not you should take the jump and try out a new tool or platform, or take the offer to collaborate with another musician or sign a sponsorship deal. It's important to think things through, but don’t let it become a barrier that results in missed opportunities.  

If Conte and Nataly like a song, they jump on it and record it immediately before everyone else does, and they make the video as quickly and cheaply as possible. Pomplamoose has developed a system, which they call the “videosong,” that cuts the production time, from idea to release, down to about one week. There are two rules for the “videosong”: The take you hear is the take you see, and if you hear it you see it. They get the mechanical licenses for covers quickly through the Harry Fox Agency.

Nataly jumped on Kickstarter in 2011, well before Amanda Palmer’s famous campaign. She heard about the platform, created a campaign, and recorded a video for her solo album before there was much buzz going around the music industry. In the end she raised $104,788 of a $20,000 goal with 2,315 backers. You can certainly still be successful on Kickstarter today, but in 2011 it was a lot easier to really stand out. Had she not decided to take the leap and try crowdfunding, her solo album may never had happened.

Patreon came together in a similarly short amount of time. Jack got the idea, sketched it out, called up an old college roommate, Sam Yam, then built the website and launched two months later.

6. Know what you want

If you don’t know where you ultimately want to be, you’ll never be able to create a plan to get you there. You need to be specific here. Just saying “I want to be a musician” isn’t enough. Do you want to be on the road playing live and meeting fans, or would you rather be home with your family most of the time? Do you want your albums to go platinum, or would you be happy just being able to get by? For Jack Conte, it was a question of whether he wanted to continue in film or go into music.

“I finished college and thought about going to film school, and then in the middle of an interview for film school they said, 'So where do you see yourself five years from now?' And it was sort of this moment where I just felt like being really honest and so I just told them, 'Well, I see myself making music and writing soundtracks and coming out with records.' And they sort of looked at me completely perplexed. And that's kind of when I started being really honest with myself about what I love.” - Jack Conte (source)

The struggles with their goals didn’t end there for Pomplamoose. After their “videosongs” started getting attention, they became an “internet sensation” or “internet musicians,” while their creative egos wanted to be known as “real musicians.” The duo eventually realized that they were doing exactly what they wanted - they were making a living in music. If what you’re doing is allowing you to achieve your goals, there’s no reason to change, even if your business model or strategy isn’t exactly normal. After all, in today’s music industry, there are so many options that you can really choose what success looks like for you.

7. Build your own model

Until recently, there was only one way to “make it” in the music industry: get a record deal. Today, the sky’s the limit and your approach really depends on a thousand little factors like your music, your fanbase, your image and your personal skills. A business model like Pomplamoose’s is certainly inspiring, but as you’ve seen, it was a result of endless experimentation, and just cutting and pasting such a personalized strategy into your career won’t necessarily work. The key is to start with a strategy, try it out, find out what’s working and what’s not, and make changes. In the end you’ll have a unique strategy that is totally specific to your music and your career.

“So YouTube seemed like a really incredible opportunity, but as good of an insight as that was, it's not repeatable. It isn't. So I don't know how to make it in the music industry and neither does Nataly. I don't think anybody really knows how to make it in the music industry, and I'm unable to repeat what happened to Pomplamoose for my solo project. I can't do it. I've been trying for years. So I guess it feels a little bit silly to say that Pomplamoose could save the music industry or anything like that. But I think it's just an example of how as an entrepreneur, using the entrepreneurial spirit, you can kinda figure out what's coming.” - Jack Conte (source)

Jack Conte is doing the exact same thing with Patreon. To him, crowdfunding was an obvious testament to music fans’ willingness to support artists, but the projects seemed very limiting, restricting musicians to large campaigns. What if you wanted to fund a stream of smaller projects like the “videosongs” that Pomplamoose releases? The tools weren’t available, so he build his own model with Patreon.

Check out more great tips from Jack Conte in this free webinar interview.


The New Artist Model is an online music business school for independent musicians, performers, recording artists, producers, managers and songwriters. Our classes teach essential music business and marketing skills that will take you from creativity to commerce while maximizing your chances for success. Get five free lessons from the New Artist Model online courses when you sign up for our mailing list.  

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