Most entrepreneurs don’t actually fail—they quit too soon. And in 2025, quitting is easier than ever. The business landscape is shifting fast, with AI, automation, and changing consumer expectations redefining what it takes to succeed. In this episode, we’re sharing a recent keynote from Gary at Jobber Summit, where he breaks down the hard truths about running and growing a business today. Whether you're a small business owner, entrepreneur, or leader, this is the real talk you need to hear. 💡 We talk about: ✔️ The biggest changes in entrepreneurship and tech (and what to do about them) ✔️ How ..read more

💡 If you’ve ever told yourself “it’s too late” to start something new, this episode is going to prove you wrong. Too many people hit their 40s, 50s, or beyond and start believing the lie that their best years are behind them. Gary is here to crush that mindset. In this episode, we’re breaking down why age is actually your greatest advantage, why experience beats youthful energy, and why you still have more time than you think. 🔥 You’ll hear from: 🔹 Chip Conley – The successful entrepreneur who joined Airbnb at 52 and turned his experience into his biggest asset. 🔹 An older entrepreneur asking ..read more

Feeling stuck in your career or life? You’re not alone. In this episode of Tea with GaryVee, I take live questions from callers struggling with change, self-doubt, and figuring out their next move. We break down what it really means to "waste time," why you're actually ahead even when it doesn’t feel like it, and how to balance ambition with self-compassion. 💥 We also dive into: How to know when it’s time to pivot your career (or stick it out) The #1 mindset shift that stops people from moving forward How to use discipline to grow your business (without losing your sanity) The real reason you ..read more

Want to stay ahead as an entrepreneur in 2025? This episode is a crash course in evolving your business, featuring three real entrepreneurs tackling three major challenges—scaling, branding, and reinvention. Pulled from the most impactful moments of 4Ds, these conversations are handpicked using YouTube analytics to help small business owners and operators navigate the realities of growth. We cover: 🔥 Building for Scale – How do you grow without losing momentum? When do you reinvest, and how do you make the right financial moves? 🔥 Balancing Identity & Growth – Managing multiple ventures wi ..read more

If you're in business and avoiding technology, you're in trouble. In this episode, I dive into why contractors—especially roofers—need to stop resisting tech and embrace the tools that will keep them competitive. I break down:✅ The brutal truth about technology in business ✅ How to overcome resistance to change and get your team on board ✅ The real way to use social media for local business growth ✅ Why brand beats sales (and how to build yours) ✅ The one video every roofer should make today If you're still thinking old-school marketing is enough, this one's for you. Let’s get to work ..read more

🔥 The game has changed—are you keeping up? In this episode of Tea with GaryVee, I dive deep into the shifting landscape of social media, why follower counts don’t mean sh*t anymore, and how content is the only thing that matters. We talk about: ✅ The biggest mistake brands make on social media (and how to fix it) ✅ Why TikTok followers don’t equal views—proof inside 🚀 ✅ How giveaways actually build community (watch me do it live) ✅ The real reason people don’t buy from you (and what to do about it) ✅ The truth about AI replacing jobs—should you be worried? ✅ What to do if you’re stuck at the ..read more

In this episode, I sit down with four business owners from completely different industries—hospitality, franchising, community-driven services, and social media marketing—to break down their biggest challenges and give them the no-fluff, high-impact advice they need to scale. ? We talk about: Franchising vs. Private Expansion – Should you franchise your business or scale on your own? The brutal truth no one tells you. Turning Customers into a Community – If your customers aren’t talking, you’re doing it wrong. Here’s how to make them superfans. The Real Way to Grow on Social Media – Why most ..read more

I sat down with Lydia Moynihan from the New York Post to dive into some of the biggest shifts happening in business, media, and technology. We get into the explosion of social shopping, how AI is changing the content game, and why traditional media is struggling to keep up. We also talk about: ? Social Shopping Takeover – Why TikTok Shop is the next big thing (and why you should be paying attention). ? AI & Content Creation – Will AI replace creators, or is it just another tool in the arsenal? ? The Evolution of Attention – Why real estate and attention are the same game, and how to capita ..read more

? How to Start a Business (Even If You Think You Can’t) Starting a business? You need to hear this. In this episode, I break down the best way to start—from working for someone in your industry to making sure you actually like what you're doing. Trust me, if you're only in it for the money, you're going to quit. We also dive into: ✅ Why procrastination is actually a sign you’re in the wrong game ✅ The REAL reason businesses fail (it’s not marketing) ✅ AI fears vs. AI opportunities (HUGE perspective shift) ✅ How I deal with burnout—and the one thing I wish for every young person ✅ Why failing i ..read more

The real fix for feeling stuck? Curiosity. So many of us are trapped in our own excuses, using judgment from family or fear of failure as a reason to hold back. If you’ve ever felt like you’re not “going hard enough,” this episode is for you. ? We talk about: Why everyone should try selling on TikTok Shop and Whatnot (even if you’re not a “salesperson”) Overcoming family judgment and finding your own path How working 6 hours a day is capping your success Growing your Instagram audience from TikTok before it’s too late The #1 thing stopping people from taking action (and how to fix it) Why mo ..read more