Seven of the Best Entrepreneurial Podcasts to Download in 2021

It’s that time of year where not only are we wrapping up gifts for under the tree, but we are also looking at wrapping up 2020. Can I get a “hell ya” on that one! Maybe you were one of the lucky few that made it through this crazy year without skinning your knees. I hope so. The thing is, no matter how impacted you were by what the year threw at us, I believe 2020 has taught us all a bunch of lessons.

The only way I made it through this year with a thread of sanity somewhat intact was by doing a ton of reading. I shared my picks for top reads <HERE>, but a lot of you responded to say…” but Diane, I don’t have time to read.” I get that. So I offered up the audio versions. But then people complained that audiobooks are so expensive. With all of the subscriptions available from Amazon Prime to Netflix to Apple TV to Hulu to HBO etc., the list goes on. I get that too. It all adds ups. 

But then I ask…what about Podcasts?

I am a podcast junkie. They are a wealth of info and span any genre. If you like true crime…there’s a podcast for that. Want to improve your health? Yep, you’d be covered. Sexual proclivities you want to explore?…bingo. (I mean…I’ve heard) Pretty much any genre that you can think of, there is a podcast for that.

But my purpose for writing this blog has always been and will always be to help travel professionals like you succeed in the career you love selling travel. So, as much as I’ve enjoyed My Dad Wrote a Porno and found that it served its purpose, I wanted to give you a list of podcasts that I listen to that helped me launch my business. Maybe you’ll find them useful too. That is to say…if you can pull yourself away from Season three of “The Crown.”

Here are my top seven podcasts, in no particular order, with a brief explanation of what to expect from each. Then you can decide if they are worth a download.

The Jasmine Star Show – featuring Jasmine Star

Jasmine’s specialty is mostly excelling at the game of Instagram, and she does it like no other. And like some of the others on this list, she is relatively new to the podcasting space, but mmmm, she’s good. She has a bit of Latina charm with a tell-it-like-it-is approach that I find refreshing. And, what I love is that I can count on her to deliver actionable steps to help me improve my success on the Gram in each episode. Much of what she shares, I regurgitate and feedback to anyone who’ll listen because she’s just that good. The only downside to her podcast is that I mostly listen while walking my dog, so I’m always having to stop and leave myself voice memos for fear I’ll forget later.

To the point, Jasmine is worth a listen.


Impact Theory – featuring Tom Bilyeu

Tom rose to his most notable success by co-founding Quest Nutrition (you know the energy bars that don’t suck, especially if you heat them for a minute in your air fryer?…Mmmmm 😋). He was at the top of his game, but like most self-starters, he found himself working way too many hours and no longer loving that particular flavour of hustle.

Enter Impact Theory. A weighty podcast where Bilyeu interviews some of the world’s best thought leaders and probes deeply into their success. He manages to tease out the commonalities between them, offering a roadmap to anyone who listens.

In full disclosure, some of his guests float way over my head. For example, his fireside chat with neuroscientist David Engleman made my brain hurt, but for the most part, I love how he digs into every interview and leaves no questions unanswered.


The Goal Digger Podcast – featuring Jenna Kutcher

What I enjoy most about the Goal Digger Podcast is that it covers all things about building a small business. From how to run Facebook ads to maximize your Pinterest exposure to how to nail LinkedIn while standing out on Instagram, Jenna covers it all. If you are someone who just wants a step-by-step approach on how to do things, Jenna has you covered.

Of course, she offers paid in-depth tutorials, but I have found she gives away most of her best advice for free. And with over 400 episodes already in the can, you have a ton to listen to if you are just getting started.

Shout out to my good friend and African travel specialist Kirsty, the owner of  Traversing Africa, who introduced me to this podcast eons ago. I take podcast recommendations as easy as I give them, so don’t forget to leave yours in the comment section below. 


The Life Coach School – featuring Brooke Castillo

Given the year we’ve had, the Life Coach School is kind of like having your own personal therapist speaking in your ear every Thursday. This podcast has been transformational in that it uncovers potential blind spots that we all know we have, yet we can’t always recognize. Hence the term “blind” spot.

While more mind-shifting than business coaching, having the right mindset is instrumental in achieving whatever goals you set out for yourself. You can have all the right pieces in place; the best website, the best travel products on offer, the most product knowledge etc., but you’ll never achieve your full potential if you come from a scarcity mindset.

And with the Life Coast School podcast, I’d highly recommend starting from the beginning if you can. I find some of her best stuff is hidden there.


School of Greatness – featuring Lewis Howes

I might just say that Lewis Howes is one of my all-time favourite interviewers (not counting Oprah, of course, duh). Like Tom Bilyeu, he manages to book the best guests, but his topics are a bit less esoteric and more digestible across the board. 

I find that I flirt between podcasts depending on my mood at the moment. But The School of Greatness is the one podcast that I’ve been subscribed to since the very beginning. It’s that good.

Plus, his interviews are long and meaty, so I know if I’m out for a long walk, he’s got me covered for the entire trip. That’s a bonus.


Entrepreneur on Fire (EOF) – featuring John Lee Dumas

If you can get past the cheesy intro and JLD’s  (as he is affectionately referred to) over-the-top enthusiasm, you’ll enjoy tuning into this podcast. His episodes are shorter, so you don’t have to block off as much time, but you still walk away with a ton of inspiration from some of the best of the best in the small-business start-up world. 

The entrepreneurs featured on his show cover all topics. And while they are not travel related per se, issues discussed are often transferable. 

The other thing I appreciate about EOF by JLD is that he’s introduced me to a lot of small start-ups that I may never have heard of otherwise. It’s crazy to me what business ideas people can dream up, but they do…and they find great success at them. I’m pretty sure it was on EOF that I first learned about Gary Vee.


The Gary Vee Audio Experience – featuring Gary Vaynerchuk

I’ll end this list with my favourite – my boy crush – Gary Vee. Now I can appreciate that Gary Vee will not be everybody’s cup of Tea straight out of the gate but hang in there. He swears like a sailor. He comes across as sounding arrogant at times when taken out of context but give him a chance. Hands down, I have learned more from Gary Vee’s podcast than any other. 

If you follow me on Instagram @asktravellingd, you’ll see how imitation is the best form of flattery. Yep, that’s where my Insta-handle came from. His original podcast that started back in 2014 was named the #AskGaryVee show. 

And I’m not alone in my admiration for the man. I’m fairly confident that every one of the podcasters I’ve mentioned above has all followed Gary at some point in their careers. He’s the podcasting guru.

If you can’t get over the cursing – maybe toss a quarter in the swear jar in his honour – if nothing else, you’ll be rich — he does offer up a clean version of his show. I have to assume it’s the same content stripped clean, but I’ve only ever listened to the original.

Gary Vaynerchuk is probably one of the most genuine and helpful podcasters in the arena. I have nothing but mad respect for him, and actually, his book “Crush it” is a masterpiece on understanding social media and launching a business.



So that’s the list. What do you think? Time to dive in? Do you have a favourite podcast? Drop a note in the comments section below — even if it’s not business related. I’m still all ears.


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2 years ago

Some good suggestions! Thanks!

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