From Sex Talk to Bestseller: WeezyWTF on Still Not Being 'Brand 'Safe'

Pretty Privilege & the Funding Game

Riana gets candid about something most founders won't say out loud — the role attraction and appearance play in early-stage funding. From noticing the drop in male investor follow-ups after cutting her hair, to reflecting on being "flown out" in her twenties without fully understanding why, she breaks down the unspoken interpersonal dynamics behind the money. Honest, sharp, and long overdue.

She Built the Future | AI, Food & Purpose ft. Riana Lynn

She never applied for a job in her life. Instead, she emailed her way into Obama's White House, learned how money moves inside a $2B private equity firm, and then built an AI company changing what billions of people eat. Riana Lynn is doing it all as a Black queer woman in one of the least diverse industries on the planet — and she's not waiting for permission. Main Topics: * How AI is reshaping the food industry and global supply chains * Why half of entry-level white-collar jobs could disappear in 5 years — and which jobs are actually safe * The real funding roadmap for founders who don't have the "right" network * Why she cut her hair mid-fundraise and what happened to her checks * What it means to be a "conscious AI leader" * Living in purpose while running a company that feeds billions If you're looking for insight into the future of AI, what it truthfully takes to raise millions, or how food security is being reshaped, this episode is for you!

The .05%: Artists Who Last vs Those Who Don't ft. Ye Ali

Most people don't make it in the music industry. Statistically, 86% of artists are never discovered. So what separates the ones who do?  This month on Your Hero's Journey, we're diving into the music industry, and Savannah kicks things off with a conversation that's equal parts tactical and deeply human. Grammy-winning producer and R&B artist Ye Ali opens up about the scrappy early days, building a network that actually shows up for you, turning down deals that didn't feel right, and what taking care of his dad taught him about purpose, legacy, and what really matters. This is a conversation about longevity — in your career and in life. In this episode, we cover: - What it really means to have an entrepreneurial mindset as an artist — even when you're signed - How Ye Ali funded his career through modeling, brand deals, and investors before music paid the bills - The $500 music career starter guide — where to actually put your money when you're just getting started - Why he chose supporters over fans and how one real interaction can spawn 20 new listeners - Why he turned down label deals, fake PR relationships, and requests to over-sexify his image — and what it cost him - Protecting your peace in an industry designed to compromise it enjoy!

Sell to Your People: WeezyWTF on Building Brands Your Audience Believes In

In this episode, WeezyWTF gets real about what it actually takes to build something from the ground up as a Black woman entrepreneur.   From opening a gym to running a production company to owning a brand, Weezy has done it across every vertical — and she's not holding back on the lessons learned. She opens up about letting go of the anger that comes with being overlooked, shifting from a scarcity mindset to one of abundance, and why chasing corporate validation might be the thing holding you back. Her message? Stop waiting for the room to let you in — go straight to your people. They will show up. A must-listen for any woman building something real.

From Sex Talk to Bestseller: WeezyWTF on Still Not Being 'Brand 'Safe'

What happens when you build an empire after talking about sex—then everyone still only sees you as the "sex girl"? WeezyWTF gets brutally real about the moment an agency told her she wasn't "brand safe" despite selling a New York Times bestselling book. In this raw conversation, Weezy breaks down the double standards she faces as a Black woman creator, why she rebranded her hit podcast from Whorible Decisions to Decisions, Decisions (and whether it actually hurt or helped). She's not holding back on the racism, the exhaustion, or the tears that came with being reduced to sex work while building multiple successful businesses. If you've ever felt pigeonholed by your brand, told you're "too much," or wondered why some creators get to evolve while others stay stuck—this one's for you. Topics: Personal branding, creator economy, podcast monetization, rebrand regrets, influencer marketing, breaking stereotypes, New York Times bestseller, building community, brand perception, entrepreneurship, self-help