Podcasts have exploded into a leading form of media in the past few years due to their ability to provide meaningful information on any topic, and be streamed at any time. Podcasts are becoming harder to ignore, while simultaneously becoming harder to discover unless you’re directly told about a show. Yet the information and entertainment found within these gems are truly unmissable. Therefore these are my favorite shows to listen to and learn from every week.

I grew up spending most of my free time playing video games and watching [adult swim] and Toonami anime. While I spend less time(and money) as an adult on games, I’m still enthralled by that world and culture. Whether you’re a fan looking to hear more about the things you’re into, or trying to get a better understanding, Castle Super Beast is a great podcast. Woolie Madden and Pat Boivan head the weekly series with almost a decade of LPs, and almost as much experience podcasting. They go thru their weeks covering topics in their wheelhouse, and then cover the big gaming and media news from the past week. Be warned though, they are not for the faint of heart or young people due their colorful use of language.
What makes this my favorite podcast is the experience and energy between Pat and Woolie. I may not be interested in every topic, but they discuss things in such an entertaining way that I will always find it informative and entertaining. Whether it is the virtual and IRL economies behind MMORPG, games as a service or random stories from their past, nothing is boring. Check out their live stream every Monday and their official release every Tuesday.

2. Group Chat
Group Chat is topically the complete opposite of Castle Super Beast. Focusing on business and pop culture with a hint of politics, Chris “Drama” Pfaff, Dee Murthy and Anand Murthy cover the biggest news three times a week. The balance of knowledge and opinionated spurts creates for an “entertaining and exciting” experience where listeners can learn about IPOs, retail business and the unstoppable takeover of businesses like Amazon. What makes this one of my top picks is the dynamic created between the three hosts. Anand and Dee bring similar knowledge, but vastly different personalities, while Drama brings a level of relatability the other two are missing. They may not always have opinions that I agree with, but it is refreshing to hear thoughts from a more mainstream and less fringe point of view. The information on stocks is also something that I would otherwise be aloof to without this show.

Gathering information is one of the main features of podcasts that attracts my attention to a show. While group discussions offer intriguing views on topics, interviews can be in-depth, especially with an experienced interviewer. Jeff Staples makes for an interesting interviewer because he isn’t necessarily experienced in interviews. Instead he is highly experienced in fashion, design and the world of hype. He uses that experience and his connections to create Hypebeast’s The Business of Hype.
The Business of Hype focuses on the business behind the flashy hype of fashion. The show feels like a discussion that should be happening at a trade show or transcribed in a trade magazine. The advantage of having a discussion between two experienced and successful individuals within the same business is giving listeners a chance to hear questions that they would not have thought of without years of experience in that field. Hypebeast is allowing their audience to understand their interest more thoroughly, and may inspire entrepreneurs to make better decisions in their field.

Short Story Long is another one of my favorite interview podcasts. Hosted by Chris “Drama” Pfaff interviewing entrepreneurs, designers, professional athletes and all around successful people about how they got to where they are. They start the story as far back as possible starting at childhood and offers extensive views into the guest’s life and transformative moments. The charm of Short Story is Drama’s genuine interest in the story. He asks what I would while listening, and does a good job representing the listener in the interview. Even when the guest is in a field that I may not find interesting, there is always a lot to learn about how to be successful in my own pursuits.

5. The Dropcast
The Dropcast is a fashion podcast covering the latest news in the fashion world. The show is produced by Highsnobiety and hosted by Jian DeLeon and Noah Thomas. The two are highly versed in fashion, and offer an expertise that keeps up with modern releases while also being able to have historical references in fashion as well. The show shines in the duos involvement in the fashion world as genuine fans and participants.
The show really excelled on their episode focusing on Paris Fashion Week. While they normally feature a guest of the week, this episode was only the two hosts having unadulterated fashion talk. They even bring up the question of high fashion and streetwear, and whether the two will grow apart once again in the next few years. I’ve found it more and more difficult to keep up with fashion news recently, and The Dropcast does a great job of making me feel in the loop once again.
Special Consideration
The thing that makes me a fan of podcasts are the routines of it. Being able to rely on them from week to week always keeps me on schedule, and coming back for more entertaining information. Yet there are podcasts that are less than routine, and downright random with releases. But these next two shows offer up so much information, and motivation that it would not be right to end this article without mentioning them.

Shannon Lee(Bruce Lee’s daughter) and Sharon Ann Lee(cultural anthropologist) host Bruce Lee Podcast and guide listeners on a broad range of topics all focused on the philosophy of the late, great Bruce Lee. From topics such as how to best position yourself in life through habits, to understanding what an ego boundary is, this podcast offers a great deal of information, that would be otherwise difficult to dive into. So much information that it could be overwhelming. My main reason for listening to podcast is for them to enhance my experience doing something else, ie driving, cleaning, drawing; podcasts are secondary in most cases. In comparison, Bruce Lee podcast is a college level lecture. I’ve found myself rewinding over and over again while driving, to the point that I now listen with a pen and pad for notes(not while driving of course). This is a great listen to those who really want it.

Much of my enjoyment with my favorite podcast, Castle Super Beast, comes from the insight and humor of my favorite host, Woolie Madden. Therefore another one of his shows would definitely be within my wheelhouse by his lead alone, but his other show is something both unexpected and necessary to listeners in this day and age. Woolie Will Figure It Out is a podcast that asks creatives to look at their work, and talk about their greatest failure in as much detail as possible. I’ve heard plenty of shows focused on success and accomplishments, but many of those have moments of failures. In those stories failures are moments and features of a bigger story, on WWFIO failures are the headliner.
In a time where everyone has a highlight reel of life through social media, it is refreshing and motivating to hear stories of mistakes. The one thing keeping this from being number 1 is the frequency. Mr. Madden says it best, “You know exactly what it is, but you never know when it’s going to happen.” Basically coming out at random, sometimes with a guest, sometimes simply answering questions like how to grow past procrastination, Woolie Will Figure It Out is something that I recommend everyone go and listen to ASAP.
Hopefully you can find as much enjoyment in these shows as I do. I’m always looking for more shows, so let me know what some of your favorite shows are in the comments. Thank you for reading.