My Top 10 Favorite Podcasts

I am a massive fan of podcasts.

I’ve spent a majority of my career working in the podcast space. So, I have seen from both sides as a consumer and a producer/host what it takes to have a great show.

Most recently I’ve been helping behind the scenes with two rocket ship shows at Shadow Lion. While they aren’t on the below Top 10 list solely cause you guys would arrest me for solicitation, DeepCut with VicBlends and Pound 4 Pound with Kamaru Usman and Henry Cejudo are must-watches.

It might be super hardo of me, but while I absolutely love music, sometimes listening to music in a long car ride just feels very unproductive. I need to throw on a podcast to feel like I am learning and getting better.

The industry is a crowded space, but I wanted to shoutout a few that standout and that I incorporate into my weekly rotation when ghost riding the whip.

I decided to rank these 10 shows in order of my favorites to spice things up…

Reply to the email with your disagreements on the list.

1. This Past Weekend

What is it?

A comedy podcast that typically features high-profile guests in 1v1 style, 2-hour plus conversation about their journey in life and beyond. There is the occasional solo episode where the host breaks down interesting cultural topics (I never listen to those).

The Host: Theo Von

If you don’t know who Theo Von is, you’re missing out on one of the funniest, most wholesome dudes on planet earth.

Theo is a chameleon, can literally fit in with any crowd. There is not a person out there that doesn’t like Theo Von, as a human being. Maybe you hate this pod, but impossible to hate him as a person.

He’s from a small-town in Louisiana and has been sober for several years. Since ditching cocaine (which he talks about A LOT), he has exploded onto the comedy scene with one of the biggest podcasts in the world while also selling out arenas on tour across the globe doing stand-up.

No coke = success. Good learning.

Why it’s ranked my #1:

Listening to an episode of This Past Weekend is a rollercoaster and you will never expect what the topic of conversation will be. Theo’s superpower is speaking whatever comes to his mind and presenting it in a comedic, entertaining way.

He gets his guests extremely comfortable (a must for any successful interview show). Actually, I would call it a “conversation” instead of an “interview”. He’s never reading off a list of questions and does a great job at going with the flow.

The best example is with YG when in the first 15 minutes you feel this very awkward tension like YG has no interest in being there, and then all of the sudden the rapper finds some sort of trust with Theo and lets his guard down turning into one of the best episodes.

Yes, it’s a comedic show and Theo says the most ridiculous things in the world that often make zero sense, BUT you’re still learning. These conversations will definitely give you a different perspective on things.

You will see a side of his world-famous guests that you have never seen before.

Say you’re a Luke Combs fan and maybe have listened to him on 10+ podcasts and interviews prior. I guarantee his interview with Theo will give you stories and a side of Luke you have never seen before.

He had on Ed Sheeren this week. I had no idea Ed was the absolute man.

One of the biggest reasons new podcasts fail is due not being unique. While a 1v1 interview show isn’t unique at all, Theo makes up for it by being one of the most unique people I have ever encountered.

I’ll stop rambling about Theo, you can tell I have a little man crush at this point.

This podcast is the perfect hour+ car ride killer if you’re looking for a place to smile and learn about cool people at the same time.

If there’s a weakness to this show, it’s that sometimes the non-sense can really go deep and be tough to reel back in. But he usually does!

Danny’s Diary Official Rating: 9.2

Listen here

2. How I Built This

What is it?

Interview show where famous entrepreneurs, mainly from consumer brands, join to teach us how they built their iconic brands from start to finish. In each episode, founders reveal an incredible amount of insights that lead to their eventual success.

Each episode is essentially a masterclass on how to navigate challenges of building a start-up.

The Host: Guy Raz

Unlike Theo, Guy Raz wouldn’t be the guy I choose to spend my weekends with.

That being said, I have never listened to a more prepared host. I respect the hell out of him.

He has a list of questions that must’ve taken HOURS to prepare. He starts from the entrepreneur’s childhood and works up until present day. And he nails every single detail of their lives 100% of the time.

This is the most powerful part of the show as the preparation makes guests more exciting to be there.

Sometimes I listen to episodes twice because I know I missed some gold nuggets in there.

Here’s some of my favorite episodes the last few weeks: Complex, Dave’s Hot Chicken, Therabody, Medium and MGA Entertainment.

Different from Theo Von’s show, this podcast focuses strictly on audio and does not record video. It is rare in today’s age of podcasting to not have a distribution channel on social media hammering clips. Video clips is how Theo’s became popular.

Instead, the audio is engineered perfectly with music and transitions that keep listeners engaged.

As someone who’s started a company and worked in start-ups, this show motivates me after every single episode.

I take as many mental notes as possible and try to apply them to my journey.

It’s cool cause most of the time they go deep in episodes regarding $$$$, in terms how much they raised, spent, revenue and made on the exit. Never afraid to chat details

A college course should be kids having to listen to this show and write essays on their learnings.

F*** books. This podcast would be the perfect business class material.

Danny’s Diary Official Rating: 8.8

Listen here

3. The Joe Pomp Show

What is it?

Sports business podcast that breaks down the most compelling storylines backed by incredible data. His best podcasts are the 10-minute solo episodes focused on specific topics. There are also the occasional longer-form interviews with entrepreneurs/athletes in the sports industry that are also very insightful.

The Host: Joe Pompliano

Joe Pomp was a former finance bro in NYC that said F’ this. He was working at a large bank while on the side writing a sports business newsletter called “Huddle Up”. The newsletter audience got large enough where he was able to quit his job. Then started a podcast as well.

Hmmmm, his journey in sports media sounds eerily similar 🤔🤔 (I quit a job in corporate America - NYC, started a sports newsletter and a pod!)

Could be why I am so drawn to Joe's content, I can very much resonate with his story.

These podcast episodes are short and digestible. The 10 minutes are PACKED with great info, and you can always trust Joe as a credible source.

I feel accomplished after listening to an episode, especially since I work in sports.

Examples of recent episode topics: The economic effect of Caitlin Clark, Tiger Woods new clothing brand, Tom Brady’s broadcasting career, why NFL rookies are ditching agents, A-Rod interview.

Joe is still early in his content creation career. I expect a lot more out of him in the near future.

Danny’s Diary Official Rating: 8.1

Listen here

4. Pardon My Take

What is it?

General sports podcast with three episodes per week. The show focuses on the most popular sports at the given moment in time, typically football leads the charge. It’s the biggest show at Barstool and they land some of the biggest names in sports to join for guest interviews as well. Episodes run 2.5 hours.

The Hosts: Big Cat, PFT and some other characters.

Big Cat is the leader and a naturally funny guy that most people love. Big Cat rocks.

PFT was previously a comedian, sometimes tries a bit too hard to land obscure jokes on the show, but good guy and I like him.

The other characters on the show all have their roles and there’s typically some fun drama to follow between them depending on where their sports fandom lies.

After 8+ years of the show, they get over a million views per episode for good reason.

Regarding their interviews, much like Theo Von, they do an unbelievable job of getting guests comfortable. They ask questions your traditional sports media journalists would never touch.

The guys develop true friendships with some of the biggest athletes and personalities in sports, and the fans grow to appreciate that.

Yes, these dudes are goofy and typical Barstool content, but they GRIND.

They record episodes at 2am on Sunday nights during football seasons in order to get new shows out Monday morning for listeners. I think the early morning launches is subtly one of the most important aspects of the show’s success.

Another long car ride gem. I usually don’t miss an episode during football season and then that drops off in the summer months depending on their guest that day.

I am a proud AWL as they would say (Award Winning Listener).

Danny’s Diary Official Rating: 7.9

Listen here

5. Smartless

What is it?

You can see the three hosts in the photo above. One of these three iconic actors brings on a surprise celebrity guest each show. The talent of guest is top tier (Will Ferrell, David Beckham, Selena Gomez, and so on).

When I say “surprise”, the other two hosts have no idea who is going to join the Zoom call prior to the interview, the guy who brings the guest on gives a blind intro without the name attached and then the other hosts try to guess who it is.

Then the guest turns on his camera and they have an hour long 3v1 interview session!

It’s a super unique format that doesn’t allow host to really prepare questions, forcing them to really go with the flow of the conversation.

Another prime example of a podcast that makes their guests comfortable.

I mean, if a podcast didn’t make guests comfy, they wouldn’t be on anyone’s top whatever list.

It’s fun to listen to celebrities interact with other big-time celebrities. It really humanizes them.

Jason Bateman is definitely my favorite of the trio.

Will Arnett brings the energy and never afraid to hammer a chirp, which I respect.

Speaking of chirps, Sean Hayes is their punching bag on every episode and I’m here for it. It’s a hilarious bit, even the guests like to get in a few solid punches.

By listening, you’ll usually get a few laughs while learning more about a very high-profile guest in a causal setting.

Sounds like a fricken’ win to me!

Biggest downside of the show is sometimes they dive too deep into the world of actors and their journeys with acting specific stories that just isn’t as relevant to the average consumer. Also, I wish they did video (only record audio even though it’s Zoom)!

Danny’s Diary Official Rating: 7.6

Listen here

Rest of my Top 10

6. The Indicator by Planet Money: 8-minute-long daily episodes on one specific relevant world topic a day that helps you become smarter. The hosts present the material in a very digestible way. Content ranges from economics to politics to media and beyond. I am a big dumb idiot, so this one is perfect for me. Listen here.

7. Golf’s Subpar / The Smylie Show: It’s a virtual tie between my two favorite golf podcasts that both do a great job on breaking down the professional game in a digestible way along with having top talent guests on the show. The Subpar hosts Drew Stoltz and Colt Knost love to have fun on air (I’ve interviewed them both together on my old show), while Smylie’s show is a tad more serious. Subpar link. Smylie link.

8. Colin and Samir Show: Hosted by YouTube “creators” with a goal to give other creators and people working in media valuable insights on how to get better in the space. Typically involves an interview with a successful creator, but my favorite are their solo episodes answering questions from the audience. Only suggest this show if you work in media. Listen here.

9. Giggly Squad: Quite literally the only podcast my girlfriend and I can agree on when we get in the car together. Hosted by two Bravo chicks from Summer House, they talk about “pop culture”, whatever the hell that means. It’s kinda funny, mostly entertaining and a good mindless listen. No shame here, I am a “Giggler”. Should be noted, host Paige DeSorbo is my #1 ranked celebrity crush at the moment and probably why I agree to listen. Listen here.

10. Social Media Marketing: Listening to this podcast only makes sense if you work in media and/or are trying to grow a following or any kind on a social platform. If that’s you, then absolutely check out this show. The host does a brilliant job of having on relevant guests with expertise in specific areas of media that you can directly apply to your work. Another pod that should be taught in college. Listen here.

Instead of podcasts, here’s one of my favorite newsletters I read to help stay in the know on adult stuff that I think you’d also enjoy! Maybe I’ll rank my top 10 newsletters next?

Money Machine Newsletter

Market Beating Stocks in 5 min. Elite traders narrow down the universe of stocks to their best ideas, delivered weekly to your inbox pre-market. Join Money Machine Newsletter today for free.

Switched it up a bit today, but then again, this is my Diary so I make the rules! Hope you all enjoy. I truly love you guys.

Shocked how many people are reading these and responding with positive feedback. Makes me ecstatic.

See you next week for another banger!

Love,

Danny Healey