Anna Rogers

How Dare You?

Business EN ↓ 16 episodes

You were taught to be nice. To be grateful.  To not want too much, ask for too much, or take up too much space. And honestly? You got really good at it. This podcast is for the woman who's ready to break the Good Girl rules. Every week, host Anna Rogers, coach, author, ex-good girl, and woman with genuinely delusional dreams gets into the stuff no one talks about at the dinner table as she unlearns people-pleasing, breaks societal conditioning, and dares to take radical responsibility for the life she actually wants.

Author

Anna Rogers

Category

Business

Podcast website

lifestylerich.co

Latest episode

Apr 17, 2026

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Episodes

8 Habits I Stole From Insanely Successful People 17.04.2026

What if success isn't about working harder… but about what you do every single day without thinking? A few years ago, I started getting into rooms with people who were making more money, moving faster, and playing at a completely different level. 8 and 9-figure entrepreneurs, VC owners, book authors. I kept thinking… "What do they know that I don't?" It wasn't strategy. It...

Why Big Dreams Feel So Scary (And Why That's the Point) 09.04.2026

What no one tells you about having a dream so big it scares you... In this episode of How Dare You, I'm breaking down why big dreams feel so scary and why it has almost nothing to do with failure.  From the identity gap that hits the moment you get serious, to the self-sabotage that disguises itself as being practical, this is the honest conversation about what going after something huge actu...

Advice to My Younger Self (I'd Be Further Ahead If I Knew This) 01.04.2026

These are the lessons I wish someone had forced me to hear earlier. After building businesses, making money, losing money, navigating relationships, and figuring out who I actually am... if I could go back and have a conversation with my younger self, this is what I would tell her. From learning to trust yourself when nothing makes sense, to the moment I genuinely didn't think I was getting o...

Why I Fell from the Face of the Earth...and Where I'm Going Next. 30.03.2026

I'm back… and I'm not the same person who left.... After moving to Bali, finally moving into the villa Tom and I spent a year building, and going down a rabbit hole of uncomfortable self-reflection, I realized something:  I'd been playing small. In my dreams, in my business, in the way I was showing up here. This episode is the unfiltered version of what happened...the mindset shift...

The Invisible Work That Separates the 1% 17.12.2025

What if the reason you’re not getting the results you want has nothing to do with talent, strategy, or timing and everything to do with what you’re willing to do when it’s uncomfortable? In this episode of Unrelatable, I unpack what the top 1% actually do differently. I break down what Taylor Swift, Tony Robbins, and Justin Bieber all have in common and how this has helped me explode in 2025. This...

How I Created $250K Cash in 90 Days by Going All In 03.12.2025

What if the biggest leap you’re craving… is one brave yes away? In this episode, I’m breaking down the last 90 days. Tthe wild, batshit season that turned into a full-blown rocket ship. The stages, the travel, the quarter-million cash months, the identity shifts… and the real reason everything accelerated at lightning speed. We’ll unpack: How saying yes before you feel ready creates exponential mo...

Behind the Scenes with Jay Shetty: What Most Entrepreneurs Miss About Success & Happiness 22.10.2025

I just got back from a three-week whirlwind trip through LA, Italy, and our first-ever Lifestyle Rich retreat in Greece. During a mastermind in LA, I had one of the coolest experiences as Jay Shetty walked into our villa and shared the behind-the-scenes of how he runs his multi–eight-figure brand. Something he NEVER talks about online. Instead to his topics around mindset, love, and relationships,...

Behind the Scenes of our Crazy Expansion in Business 23.09.2025

In this raw behind-the-scenes episode, Tom and I take you inside one of the most expansive, soul-stretching week. From speaking in front of 1,000 women… to closing multiple five-figure deals. In this episode, we share what really happened at Living Brave Live (including the standing ovation moment that changed everything) and how YOU can start taking bigger swings in business.

How Conditional Enthusiasm is Stopping You from Exploding Your Business 04.08.2025

What if the reason your business isn’t growing… has nothing to do with your strategy and everything to do with your energy? In this episode, we’re talking about the silent killer of momentum: conditional enthusiasm. We’ll unpack: Why revenue is one of the worst metrics of "success" The unsexy truth about quantum growth The invisible metrics high-level leaders obsess over (hint: it's...

The Future of the Coaching Industry: 3 Shifts You Can’t Afford to Ignore 22.07.2025

After 10 years in the coaching space—scaling four multi-6 and 7-figure brands, coaching thousands of clients, and running both a coaching company and a SaaS startup—I can see patterns and trends. The coaching industry is entering a new era. In this episode, I break down the 3 biggest trends shaping the next 5 years—and what it’s going to take to not just keep up , but lead. I'm breaking down:...

The 1% Crazy: Why You Have to Be a Little Unhinged to Win 27.06.2025

In this episode, I’m joined by my husband, co-founder, and partner in all things crazy—Tom Rogers—for a raw, unfiltered conversation about what it really takes to succeed in business. We talk about being part of the “1% crazy”—the kind of entrepreneurs who choose uncertainty, intensity, and expansion over comfort and logic. From building six and seven-figure companies, to getting punched in the fa...

Living a RICH life 12.06.2025

"I want to be so rich in experiences that money can’t even compete." In this episode, I’m taking you behind the scenes of one of the craziest 72 hours of my life. I talk about what it really means to design a life that is rich in money and moments. 

Moves I Made to Go from $20k Months to $60k-$100k Months 02.06.2025

In this episode, I walk you through the exact brand and identity shifts I made behind the scenes to go from consistent $20K months… to $60K–$100K months. I break down the three core areas that changed everything—my identity, my vision, and my brand presence—and how realigning them brought my business feel ALIVE again. If you're not playing at the level you know you're CAPABLE of...this e...

$100k in 35 Days 16.05.2025

In this episode, I take you inside the offers, brand elevation, and deep identity work that led to a $100K month in just 35 days. I break down the intentional strategy, emotional leadership, and inner recalibration it took to create that kind of money—while being deeply obsessed with my actual life. This is a raw, honest look at what it really takes to scale—through both the strategic moves and th...

Love, Business & Everything In Between 13.05.2025

In this episode, I’m joined by my husband, Tom Rogers—my co-founder, business partner, and the man who’s been by my side through every messy, magical chapter of this journey. We talk about how we fell in love, the wild decision to start our first business together, what it’s really like to scale companies, and how we’ve navigated love, money, and leadership without losing each other in the process...

Eating Fear for Breakfast and Becoming Unrelatable 13.05.2025

In this first-ever episode, I share the real reason behind the name Unrelatable —and why being too much is exactly the point. Because when you’re fully expressed, deeply embodied, and wildly successful… you shouldn’t be relatable. I’m also sharing a BIG project I’ve been working on, and the fear that nearly stopped me from starting.

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