Best Difficult Convos Podcasts (2025)

1
Side Hustle = Full Time? 30 Min Of Tactical Social Media Advice | GaryVee Backseat Q&A Highlights 29:18

3h 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!…

1
Zarna Garg: Proof It’s Never Too Late to Start Over (and Crush It) | GaryVee Audio Experience w/ Zarna Garg 31:22

1d 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 …

1
228. Divorce’s Quiet Pain 💔: Asking for Support Without Feeling Needy (Send this episode to your bestie) 8:06

1d ago8:06

8:06

Join The list for A Different D Word Have you ever felt surrounded by people, yet completely alone in your divorce? Even if you’ve got friends checking in or family around, that silent ache you feel—the one nobody asks about—can make post-divorce isolation feel insurmountable. When you’re barely holding it together, asking for support feels impossi…

1
The Future Won’t Wait: How to Build When Everything’s Changing | GaryVee Samsung Keynote 39:07

3d 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…

1
227. How To Stop People Pleasing After Divorce Without Becoming “The Difficult One” (Because It's Destroying Your Nervous System) 20:41

3d ago20:41

20:41

Join The list for A Different D Word Have you ever found yourself saying “yes” when you desperately wanted to say “no”—and then wondered why it’s so impossible to break this pattern, especially now that your marriage is over? If you’re feeling exhausted from constantly trying to keep the peace and worried you’ve lost touch with who you really are, …

1
MicroVee: Time Management’s Best-Kept Secret: Imperfection | GaryVee Throwback Q&A 2:03

5d 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…

1
MicroVee: How to Get Comfortable With Losing and Start Winning | GaryVee Throwback Aspire 2024 Keynote 7:06

6d 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…

1
MicroVee: How To Win In An AI World — Use Fast-Changing Tech Before It Uses You | GaryVee x Alpha AI Podcast 14:45

7d 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…

1
The Harsh Truth About Modern Marketing (And Why You're Still Losing Attention) | GaryVee Elevate Event Throwback Keynote 41:49

8d ago41:49

41:49

In this throwback keynote from Elevate 2017 in Copenhagen — the first 40 minutes of it — I lay out the real game of business in today’s world: 🎯 It’s not about who’s got the best product. 📲 It’s about who’s best at grabbing and keeping attention. Whether you’re in SaaS, hospitality, DTC, or B2B — this is about understanding that you’re not just in …

1
226. What If You Could See Yourself Through My Eyes 😍 Rebuilding Confidence After Divorce 10:23

8d ago10:23

10:23

Join The list for A Different D Word For many women, the aftermath of divorce is riddled with self-doubt and relentless self-criticism, hampering the path to healing. What if the true step towards renewal isn't in trying to fix perceived flaws but in transforming the lens through which you view yourself? This episode unravels the profound impact of…

101
The Marketing Unlock That Actually Works in 2025 | GaryVee Elevate Event Throwback Q&A 59:41

9d ago59:41

59:41

📍 From the ELEVATE 2017 Conference in Copenhagen, Denmark 📆 Recorded in 2017, more relevant than ever in 2025 We’re living in an era where attention is everything, and yet so many people are still sleeping on the opportunity right in front of them. This keynote/Q&A combo from my 2017 trip to Copenhagen hits on a mindset that’s even more relevant no…

101
Social Media Changed Everything. Are You Still in Denial? | GaryVee Keynote 39:53

10d ago39:53

39:53

💥 Social Media Changed Everything. Are You Still in Denial? This is the full keynote and Q&A from my 2022 talk at the NAHREP conference in San Diego — and honestly, it hits harder now than it did back then. I break down exactly why content is still the most practical way to grow your business, why so many people are still making excuses instead of …

1
225. How To Let Go After Divorce Without Dwelling On Your Ex’s Faults 22:01

10d ago22:01

22:01

Join The list for A Different D Word Divorce is tough enough without being your own biggest critic. When you dig into this episode, you'll realize those harsh judgments may actually be a reflection of issues you need to work through within yourself, offering a starting point for genuine healing. You'll figure out why those pesky habits of your ex d…

151
MicroVee: How to Balance Your Main Gig and Your Side Hustle | GaryVee Advice 11:10

11d ago11:10

11:10

If you’re trying to turn your side hustle into your main thing but feel stuck, overwhelmed, or just plain exhausted… this one’s for you. Destiny’s been grinding—working a full-time 9-to-5 while building her hair extension business on nights and weekends. But when she came on the show, it was clear she needed a mindset reset more than a marketing pl…

151
MicroVee: Why Linkedin Is Crucial in 2025 | GaryVee Keynote 13:01

12d ago13:01

13:01

If you’re still sleeping on LinkedIn in 2025, this is your wake-up call 🚨 I’ve been shouting this for a while — the amount of organic reach and business opportunity on LinkedIn right now is insane. In this keynote from a recent Vegas conference, I break down why LinkedIn is behaving like Facebook did back in 2013… and why it’s a massive miss if you…

1
MicroVee: Which social media platform is right FOR YOU? |GaryVee Podcast Moment 10:45

13d ago10:45

10:45

If I were starting from scratch in 2024, here’s exactly how I’d approach social media marketing 💡 There’s so much confusion right now around what platforms to focus on — especially for beginners. In this episode, I map out the different paths depending on what you sell, who you're selling to, and what kind of creator you actually are. B2B? Start on…

1
AI Won’t Replace You—Unless You Let It | Tea with GaryVee Ep. 73 1:09:27

14d ago1:09:27

1:09:27

This Tea episode was wild—in the best way possible. I went deep with a bunch of callers on everything from building personal brands to battling imposter syndrome, choosing between buying a house or opening a dream pizza shop, and even bouncing back after Etsy shut down a six-figure store. If you’ve ever felt stuck, scared to start, or unsure which …

1
MicroVee: How to Turn Viral Content Into Sales — Marketing Framework For 2025 | 4Ds Business Consultation 6:30

15d ago6:30

6:30

2025 is here, and the game has changed 🧠📱 In this episode, I go deep on one of the biggest missed opportunities in marketing today: turning viral content into actual conversions. Just because something got 4 million views doesn’t mean people are going to buy — but there’s a way to bridge that gap 👊 I break down: The shift from social networks to in…

1
224. Rubbing Your Ears?! The Divorce Anxiety Hack Nobody Told You About 11:25

15d ago11:25

11:25

Join The list for A Different D Word Navigating through the emotional turmoil of a divorce often feels like a battle between your mind and body. Yet, there's a surprisingly simple tool at the tip of your fingers that can help you regain control. In this episode, you'll gain insight into the profound connection between your nervous system and emotio…

1
MicroVee : The Four Steps That Lead to Real Success | GaryVee Rant 5:45

16d ago5:45

5:45

Ever feel like you’re doing a lot but not actually getting anywhere? In this quick but powerful episode, I break down a new acronym I’ve been thinking a lot about: L.O.V.E. No, not the romantic kind — I’m talking about the four real drivers of progress: Learning. Observing. Providing Value. Executing. 💥 I share why being curious beats being clever,…

1
THIS Is The 1.5 Hr Car Ride That Will Change Your Business Strategy For GOOD | GaryVee Backseat Q&A Pt.2 45:02

17d ago45:02

45:02

On today's episode of the GaryVee Audio Experience, we’re diving into the first-ever Backseat Q&A — a raw, no-filter format recorded mid-travel. Gary tackles hard-hitting personal and professional questions, covering everything from toxic family business dynamics to managing team chaos in high-growth companies. Whether you're trying to escape a bad…

1
223. Middle School All Over Again 📼 How Divorce Recreates Feelings of Social Anxiety 32:06

17d ago32:06

32:06

Join The list for A Different D Word Feeling like you don't belong during a divorce can be just as awkward and isolating as being in middle school, and if we’re being honest, it can be downright damaging. This podcast episode tackles that uncomfortable truth head-on with Coach Tiffini, exploring the real reasons behind this longing for acceptance a…

1
Overcoming Healthcare Hurdles: Inspiring Stories from Laura Romero and Desiree Taliancich 34:06

17d ago34:06

34:06

On this episode of Catalyst Convos, host Amy Grover is joined by Laura Romero, a university student living with epilepsy, and Desiree Taliancich, a nurse practitioner diagnosed with Lambert-Eaton myasthenic syndrome (LEMS). Together, they dive deep into the unique healthcare challenges in the Hispanic community and share invaluable advice on self-a…

1
Business Advice You’ve Been Waiting For… In One 1.5 Hr Car Ride | GaryVee Backseat Q&A Pt.1 48:31

18d ago48:31

48:31

On today's episode of the GaryVee Audio Experience, we’re diving into the first-ever Backseat Q&A — a raw, no-filter format recorded mid-travel. Gary tackles hard-hitting personal and professional questions, covering everything from toxic family business dynamics to managing team chaos in high-growth companies. Whether you're trying to escape a bad…

1
7 Minute Crash Course On Live Social Shopping 7:03

19d ago7:03

7:03

In this clip from Gary’s appearance on Squawk Box, he dives into a trend that’s about to explode in the U.S. — live social shopping. If you’ve been sleeping on platforms like Whatnot, TikTok Shop, or even Instagram Live as sales channels, this is your wake-up call. Gary breaks down how social commerce is evolving, why it’s dominating overseas, and …

1
How not to make a $100,000 ? | Erika Taught Me Podcast 4:20

20d ago4:20

4:20

On today’s episode, Gary sits down with Erika from the Erika Taught Me podcast for a powerful conversation that flips the typical “get rich quick” mindset on its head. If you've ever asked, “What’s the fastest way to make $100K?” — this one's for you. But Gary’s take might surprise you. He challenges the idea of speed altogether and dives deep into…

1
Commercetainment is the future, don’t miss this opportunity | Tea with GaryVee Ep. 72 35:49

21d ago35:49

35:49

Today's episode of the podcast is Tea with GaryVee Ep. 72! This episode was one of those rare ones where the energy in the room matched the depth of the conversation. You’ll hear Gary talk about commerce-tainment in real time—literally selling while delivering value—and it perfectly sets the tone for what this show is about: merging business with r…

1
Want to be a Good Manager, CEO, Founder, Parent, Leader? | After the Tea Episode 1 11:34

22d ago11:34

11:34

Have a business question for me? I'm trying something new, the first episode of After the Tea is here. With Tea with GaryVee exploding, a lot of questions are coming in, so sometimes while I travel, I'll be answering some of them in this format. This is for managers, CEO’s, founders, parents, leaders of all sorts... Hope you enjoy it, and please le…

1
222. Your Nervous System Has a Post-Divorce Secret Language...Are You Accurately Translating? 16:45

22d ago16:45

16:45

Join The list for A Different D Word Have you ever felt like you're at war with yourself, trying to heal after a divorce? It might be time to stop fighting and start listening. We all want a life full of peace and clarity after ending a marriage. But surprisingly, our deepest fears and beliefs can throw unexpected obstacles in the way of healing. W…

Podcasts Worth a Listen

Difficult Convos Podcasts

Podcasts Worth a Listen