25,000 monthly downloads

Launched in December 2015

2 episodes a week

Hello! What’s your background, and what’s your podcast about?

I’m David Kadavy, and I’m host of the Love Your Work podcast. I love creative people and I love creative work. I’m really fascinated with how people find the intersection on their “love and money” venn diagrams. It’s something I’ve always striven to do in my career as a designer, an entrepreneur and an author.

I interview creative entrepreneurs who have built businesses and bodies of work that are completely their own. I alternate one-hour interview episodes with roughly ten-minute “essay” episodes, in which I often share lessons that I’ve learned in the interviews.

I’ve been very fortunate to interview incredible guests such as Seth Godin, James Altucher, and Steve Case. I’ve also interviewed a ton of other interesting people you may not have heard of – people who have sailed around the world, started a chocolate company in Colombia, or built a living as a travel blogger.

What was the motivation behind starting the podcast?

The idea for Love Your Work marinated in my mind for years. I’ve always personally tried to find success by my own definition, and I wanted to ask my heroes how they did it themselves. I procrastinated for a long time, but I was all along studying other podcasts.

If I had found another podcast that satisfied what I wanted to hear, I wouldn’t have started my show. But I felt there was something missing. There was room for something less about traditional definitions of success, and more about finding what success means to you.

I had my own ideas about how to find your version of success from my career as an entrepreneur and author. I approach most interviews with an internal hypothesis about what lessons the particular guest will help me find. Some ways I’m glad that I prepared are that I took many performance-related classes before I ever did my first episode: sketch writing, improv, acting, storytelling, and voice. That may seem like overkill, but I enjoy all of those crafts individually. Still, I think most people overlook that a podcast is a form of entertainment, and there’s no limit to the extent you can study how to be more engaging and professional in making your show. I also had some experience with audio production, which I had gained from building online courses. And, as a designer, I knew how to do my own graphics and code and maintain my website.

Financially, the podcast doesn’t make a ton of money – a little more than break even. I’ve considered quitting many times, but the conversations I have with my guests are too valuable, and the response from my listeners is too moving. I moved to Colombia when I started the podcast to cut my expenses, but most of my income currently comes from online courses, book sales, and affiliates.

What went into launching the initial podcast?

I was sitting in a room I had rented for a month in New York’s East Village when I finally started the show. I got an email from Paul Jarvis’s newsletter, talking about how easy and fun it was to start a podcast. I immediately emailed my first interviewee – Jonathan Wegener of Timehop. A couple of days after emailing Jonathan, I went by his office and interviewed him.

In parallel, I was obsessing over what to call the podcast. Was I famous enough to just call it “David Kadavy’s Podcast”? (I concluded: No way.) Did I want something really on the nose and searchable, like “Entrepreneur Podcast?” Nope, that was too restrictive for my wandering curiosity. I wanted a wide umbrella under which I could explore many topics. Love Your Work turned out to be that umbrella. It’s something that conveys something very important to me. I also love that I can send potential guests an email with the subject line “Love Your Work,” and have it mean something. I bet that has helped me land so many great guests.

I tried not to restrict myself too much on format, but rather do what came naturally, and then go from there. It turned out to be not only a good place to have conversations with my heroes, but also to share my writing – often with lessons I’ve learned from my heroes.

A few weeks after my interview with Jonathan, I returned to Chicago, where I was living, and did a few other in-person interviews. James Altucher had sent a whole studio’s worth of equipment to my friend, Robbie Abed. I guess Robbie was going to start a podcast on a network that James was starting, but I don’t think that ever happened. Robbie kept telling me to use the equipment to start a podcast, so that was a sign from the universe after years of putting it off. Ironically, Robbie never launched his podcast, and I’ll never let him hear the end of it (I’m also forever indebted to him).

Jason Fried of Basecamp was the first episode of the show. I interviewed a handful of people for him, but he was really the archetype of what I was trying to convey – he questions conventions every chance he gets, and he does things his own way. It was also nice to have some interviews under my belt before interviewing him, so it could be ever-so-slightly better than it would have been otherwise. I searched for a theme song and simply had to have “See In You” by The Album Leaf, which had powered many of my writing sessions. I emailed Sub Pop records and paid $500 to use it for a year. (I’ve since changed songs a couple of times.) I used Audacity to remove noise and apply EQ to the raw audio, and I cut everything together with Garageband. I bet I was spending ten hours per hour of podcast early on. But the hours melted by. It was the first time in awhile I lost track of time doing something.

How have you attracted listeners and grown podcast?

I could have done much better on my launch. I really dislike trying to coordinate a bunch of things, especially after working so hard to make something. I simply made sure to debut with a few episodes. On December 15, 2015, I emailed the Jason Fried episode to my list, which was 35,000 at the time. The next day, I emailed them about the Jonathan Wegener episode. The following day, I emailed with an article about my design process for the show name and artwork. The following week, I solicited reviews, explaining that the day after Christmas is a big day in the iTunes Store (because people have new gadgets), and that they could help the show rank. I also shared on social channels: Twitter, Facebook, Instagram.

The show made it to #1 in the Business category. The first day, I had 513 downloads, the second day, we peaked at 1,046 downloads for the day. These days, when a new episode debuts, we have about 1,700 downloads. It’s important to note that Libsyn has changed their stats to be IAB compliant, so a download today is more strictly-measured than a download yesterday. Not only has the show’s growth been flatlined for two years, downloads have actually dropped because of these changes in measurement. Yeah, it hurts.

People ask me about how to grow a podcast, and I really have no idea. Podcast growth is incredibly slow and difficult. You’re asking people to make a big behavior change to find your show in an app and give it a bit of their precious listening time. Some of the best marketers I know have been completely baffled at how to grow a podcast. Having big guests that people search for does help, but only a small amount. Tweaking iTunes SEO does help, but only a small amount. Having inbound search on show notes does help, but only a small amount (this is where growth would be easier if the show were more nuts and bolts – the kind of stuff that people search for). Even socially engineering to get the show featured on a big banner on iTunes provided only a temporary jump in downloads. Advertising on Overcast did work well, but that costs money.

My biggest failure was my first “round-up” episode – should you make your bed. I spent six weeks on that episode and the accompanying marketing and it barely outperformed any other episode. I still think I got much better at making that kind of narrative episode in the process. My next round-up – find your calling – was much easier, though still not an explosive source of growth.

For anyone thinking of starting a podcast, I’d tell them to be prepared to have nobody listen for a very long time. Be prepared to feel like you’re being punched in the stomach because you’re working so hard and nobody cares. Think about someone like Drew Ackerman from Sleep With Me. He made three episodes a week for three years before he made any money on his show. Are you prepared to push that hard?

What’s your business model, and how have you grown your revenue with having the podcast?

While podcast growth has been hard, things have improved on the sponsorship front. My show has below the magical “5,000-downloads” number that you hear is required to get sponsors, bust I still I have almost all of my ad inventory sold out this month.

I make money through sponsorship, and also through my Patreon page. I also sell some books and courses.

For finding sponsors, my advice is to be proactive. I spent a lot of time thinking about which sponsors would be a good fit, or listening to similar shows to see who is sponsoring. With a little sleuthing on LinkedIn, and guessing some email addresses with the aid of a tool like FullContact, you can get in touch with many decision makers. Now, I have some pre-existing sponsor relationships, so sponsorships come more organically.

For Patreon, my advice is to not treat the premium content you provide as a “product.” People want to feel good about giving to a show they enjoy, and the bonuses are just that – bonuses.

What are the biggest challenges you’ve faced and obstacles you’ve overcome when it comes to running the podcast? If you had to start over, what would you do differently?

I was blindsided by how hard it is to grow. I also think I wasted a lot of time worrying about my rankings in Apple Podcasts, or how many reviews I was getting. I think it’s far more valuable to find ways to engage with your loyal listeners. That’s something I work on a little but I could still get much better at.

Have you found anything particularly helpful or advantageous?

The biggest mistake I made was not starting sooner. I first fantasized about starting a podcast as far back as 2004. I can only imagine how much farther I could have gotten by now if I had started. (Starting is something I’ve struggled with over the years, which is why I wrote a book about it.)

The Podcast Movement conference was definitely worth going to. I made some connections that got me sponsorships, and I made friends who understand what it’s like to try to run and grow a podcast.

A good decision I made was investing in a post-production company. I record the episodes and put the relevant information in a spreadsheet (AirTable, specifically). It really saves me a ton of time and I can concentrate on other parts of my business. I’ve also started batching production on a monthly basis, though I do think if you try this before you find your own way of working, you run the risk of burning yourself out.

What’s your advice for podcasters who are just starting out?

Make your first episode right now. It’s okay if you don’t even release it. Just listen to it as you would any other podcast. Really try to take it in like you didn’t know yourself. What can you improve? Action is everything.

Where can we go to learn more?

Listen to my podcast on iTunes!