Best Difficult Convos Podcasts (2025)

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Life Interrupts Us: The Maturation of lil Stevie pt. 2 2:00:20

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1d ago2:00:20

2:00:20

Season Two - The Journey of the Creatives Episode 5 - The Maturation of lil Stevie pt. 2 Welcome back to The Journey of the Creatives! We're thrilled to dive even deeper into Season Two, where we continue our candid conversations with inspiring creatives, exploring the unique paths they've forged, the unexpected detours they've encountered, and the…

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POV: You're An Intern At VaynerMedia & I'm Sharing My Social Media Marketing Playbook | GaryVee Q&A 23:33

2d ago23:33

23:33

Today's video is one of my favorite meetings of the year: meeting with VaynerMedia's interns and answering questions, like what the future of AI in media looks like, and whether or not ChatGPT will take over creative. I talk about how AI is shaping the marketing field, and give my two cents on the best way to improve your skillset to become experts…

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Life Interrupts Us: From NFL Dreams to the Gospel/R&B Scene - A convo with my bro Takim Brown! 1:59:13

4d ago1:59:13

1:59:13

Season Two - The Journey of the Creatives Episode 4 - A Deep Conversation With my Bro Takim Brown. Join us for an incredibly powerful and inspiring conversation with Takim Brown, a man whose life journey is a testament to resilience, faith, and the transformative power of redemption. In this episode, we delve into Takim's remarkable story, tracing …

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This Is What Entrepreneurship Really Looks Like | Kass and Mike Lazerow 35:42

10h ago35:42

35:42

I've said it before—entrepreneurship is a grind, and today’s episode is a masterclass in why. Kass and Mike Lazerow, two people I love like family, just released their new book Shoveling $h!t : A Love Story About the Entrepreneur’s Messy Path to Success*. It’s real, unfiltered, and packed with insights that go way beyond business. We talk about wha…

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MicroVee: The Worst Business Advice I Ever Got — And How It Made Me Win or 7:31

2d ago7:31

7:31

Today’s MicroVee is a powerful reminder that bad advice can lead to great outcomes — if you trust your gut. I sat down with Massimo Marioni from Fortune and shared one of the worst pieces of business advice I’ve ever been given… and how ignoring it helped me build a massive retail business. We also chopped it up about the best advice I got from my …

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This One Shift Will Make or Break Your Brand in 2025 | GaryVee Advertising Week Interview 23:03

4d ago23:03

23:03

This one’s for anyone in marketing who’s still clinging to outdated tactics. I sat down for a conversation at Advertising Week and went deep on how the industry is changing — fast. From the collapse of social media as we knew it to the rise of live shopping, AI influencers, and attention-based algorithms, this episode covers where marketing is actu…

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Give Me 7 Minutes, I’ll Delete Your Fear Of AI | GaryVee Q&A 7:02

10d ago7:02

7:02

Today’s episode is all about AI — the fears, the facts, and most importantly, the mindset shift you need to thrive. We’ve compiled some of my strongest takes on the future of work and how AI fits into it. You’ll hear from people who are genuinely scared they’re about to be replaced… and I’ll give you the exact advice I’d give my own team. This tech…

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If You Don’t Understand AI Yet, You’re Already Falling Behind | GaryVee Rightworks Keynote 37:55

12d ago37:55

37:55

In this episode, Gary speaks to a group of business owners about the real challenges and opportunities in today’s landscape — from the rapid evolution of AI to the often-overlooked power of consistent social content. He explains why many businesses aren’t seeing results with digital marketing, how simple strategies like localized video ads can driv…

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MicroVee: What Happened When I Sent a $400 Thank-You Gift | GaryVee Keynote Clip 6:33

14d ago6:33

6:33

Sometimes the smallest gesture creates the biggest return. In this episode, I talk about one of my favorite stories ever—where a simple act of gratitude turned into a massive business opportunity. This is for all the entrepreneurs out there who are obsessed with scale and tech... but might be sleeping on the old-school moves that really build brand…

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How to Succeed in the Workforce After Graduation | GaryVee 2024 NYU Commencement Speech 15:43

16d ago15:43

15:43

This is my 2024 commencement speech at NYU Stern — one of the most important talks I’ve given. I break down what graduating students actually need to know before entering the real world. This isn’t about hype or theory — it’s about the mindset and clarity you’ll need to succeed in a tough job market and an even tougher business landscape. We talk a…

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Still One of the Best Talks I’ve Ever Done | Dutch Bros 2017 keynote/Q&A 44:05

18d ago44:05

44:05

I’m bringing you one of the most impactful keynotes I’ve ever done—my 2017 Q&A with the Dutch Bros Coffee team in Portland, Oregon. It’s been a fan-favorite for years and I totally understand why: the energy, the heart, the realness in this room was just unreal. No fluff—just practical, emotional, and deeply honest takes on leadership, burnout, amb…

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Life Interrupts Us: An Intimate Conversation with Author, LaKeisha Williams 1:14:18

18d ago1:14:18

1:14:18

Season Two - The Journey of the Creatives Episode 3 - An Intimate Conversation with Author, LaKeisha Williams Join me on Life Interrupts Us for a deeply moving and incredibly important conversation with my niece, LaKeisha Williams. LaKeisha has bravely penned a book, "All Things New," detailing her personal experience with domestic abuse and her co…

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This Is Where AI Is Taking Us — An AI & Social Media Playbook For 2025 | GaryVee w/ Iced Coffee Hour 1:06:15

20d ago1:06:15

1:06:15

🔥 Ever wonder what really fuels consistent success? In this powerful, introspective episode, I sat down with the hosts of The Iced Coffee Hour for one of my most vulnerable and wide-ranging conversations yet. We get into gratitude, hard work, burnout, parenting, AI relationships, and everything in between. This isn’t your typical motivation talk — …

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Give Me 62 Seconds... I'll Change Your Life Forever 1:02

21d ago1:02

1:02

The insane 400 trillion to 1 odds of becoming a human being is enough to drive me daily, I'm just grateful for this at bat!!

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Legacy, Attention & Building Something That Lasts in 2025 | GaryVee x Maury Povich Conversation 48:01

23d ago48:01

48:01

This episode comes from my appearance on On Par with Maury Povich, and it turned into something really special. We went deep — like deep deep — on the stuff that really matters: legacy, media, parenting, regrets, and where the world is heading next. Maury’s a legend. He’s lived through the golden ages of radio, TV, and now digital. We talked about …

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The EXACT Formula I Use to Grow Businesses with Organic Social Content | GaryVee Possible Keynote/Q&A 35:30

25d ago35:30

35:30

This one’s for the marketers, brand builders, and business leaders still clinging to yesterday’s playbook. In this high-energy keynote and raw Q&A from the POSSIBLE conference, I’m throwing punches—at outdated marketing models, bloated ad budgets, and the creative delusion plaguing our industry. We’re in the Interest Media era now. Organic creative…

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The Future of Marketing, Regret, and Human Truth | GaryVee Fireside Chat 28:34

27d ago28:34

28:34

I’m getting deep on this one—this is a raw and reflective talk I gave recently, and it goes way beyond business. I touch on what it means to simplify your life, how gratitude and guilt have driven my success, and why judgment is the killer of potential. We also talk about: The massive shift coming when glasses replace phones Why the scariest thing …

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MicroVee: AI Is Eating Google Search: What Every Business Should Do Next | GaryVee Bloomberg Interview 5:43

28d ago5:43

5:43

AI is flipping the script on search—and most brands aren’t ready. In this episode, I sat down with Bloomberg to break down the massive shifts happening in digital marketing, thanks to AI-powered search engines, and how every brand—from Fortune 500s to startups—needs to urgently adapt. We talk about what Apple’s shift away from Google search really …

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How to Be a Great Collaborator in Any Industry | GaryVee x Neil Patrick Harris Q&A 32:44

30d ago32:44

32:44

I had an unreal time chopping it up with the legend himself, Neil Patrick Harris! 🤯 This convo goes WAY beyond acting – it’s about creativity, adaptability, and how to keep reinventing yourself while staying true to who you are. Neil’s been on a wild journey from Doogie Howser to Gone Girl to Broadway to magic at the Magic Castle… and yet he’s stil…

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Forget Algorithms — Here’s How to Actually Grow in 2025 | GaryVee Keynote BizX 42:55

1M ago42:55

42:55

This one’s for the real entrepreneurs—the ones in the trenches building something that matters. In this keynote from the BizX conference, I go deep on the real traits of successful business owners: resilience, adaptability, and the relentless pursuit of attention through content. We’re entering a world where platforms like ChatGPT and AI-driven sea…

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The Marketing Strategy Every Small Business Is Sleeping On | GaryVee BizX Keynote 2025 32:22

1M ago32:22

32:22

This one’s a MASTERCLASS for every small biz owner, startup founder, or scrappy team trying to grow with limited resources. I kicked off this keynote with a personal story—my family’s immigrant journey, my days flipping baseball cards, and how I scaled my dad’s liquor store from $3M to $65M without outside capital. 💥 But here’s the truth bomb I dro…

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Side Hustle = Full Time? 30 Min Of Tactical Social Media Advice | GaryVee Backseat Q&A Highlights 29:18

1M ago29:18

29:18

Today’s video is the “best of” my 1.5 hour Backseat Q&A! So if you missed it, or just wanted to catch the highlights, this video is for you. I talk about taking your side hustle full time, whether or not social media is skill or pure luck, and how to stay consistent making content (and making it viral). Hope you enjoy!…

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Zarna Garg: Proof It’s Never Too Late to Start Over (and Crush It) | GaryVee Audio Experience w/ Zarna Garg 31:22

1M ago31:22

31:22

I sat down with my good friend Zarna Garg, and what unfolded was a raw, unfiltered conversation about rejection, resilience, and rewriting your story — even when it feels like the world just slammed a door shut. Zarna is one of the funniest, most driven people I know. From stay-at-home mom to touring stand-up comic, bestselling author, and opener …

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The Future Won’t Wait: How to Build When Everything’s Changing | GaryVee Samsung Keynote 39:07

1M ago39:07

39:07

In today’s episode of The GaryVee Audio Experience, we're sharing a powerful keynote Gary gave at Samsung — all about leadership, adaptability, and thriving in the face of chaos. Gary dives deep into why the old rulebooks for business no longer apply, and how kindness, accountability, and relentless adaptability are now the ultimate competitive adv…

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MicroVee: Time Management’s Best-Kept Secret: Imperfection | GaryVee Throwback Q&A 2:03

1M ago2:03

2:03

Happy Sunday! Time management isn’t about mastering every moment — it’s about your relationship with imperfection. In this episode, we dive into why the most successful people drop balls all the time — and how being comfortable with imperfection is the real secret to getting more done. Learn how to free yourself from the fear of failure, stop judgi…

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MicroVee: How to Get Comfortable With Losing and Start Winning | GaryVee Throwback Aspire 2024 Keynote 7:06

1M ago7:06

7:06

🚨 Content Creation Blocked? Here’s the Truth That Will Change Everything! 🚨 Do you ever feel stuck when it comes to content creation? Gary has some powerful insights on how to push through that block and start creating content that actually resonates! In this episode, I share the mental shift that needs to happen in order to break free from the con…

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MicroVee: How To Win In An AI World — Use Fast-Changing Tech Before It Uses You | GaryVee x Alpha AI Podcast 14:45

1M ago14:45

14:45

Let’s be honest — most people have no idea what they’re talking about when it comes to AI... but they’ll pretend they do. In this conversation, I pull back the curtain on what I’m actually doing with artificial intelligence, how I’m thinking about it, and why humility is the cheat code in an era where everyone’s faking it. This episode is for the l…