Building a Media Presence Worth Paying For, Escaping Substack's Trap, and Selling Your Business Without Selling Out with Lex Roman

Modern media is the connective tissue of our online society. Where we consume content, what we read, share, and save directly reflects our values, impacts behavior, and shifts culture. RIP Buzzfeed listicles :(Do you pay attention to the platforms you use? Who funds the media companies you publish on? Or why you're using them, and what for?Lex Roman, founder of Revenue Rulebreaker, a community-fueled small business media backed by over 400 paid subscribers, is on today's ep to break down the misunderstood world of indie (independent) media, paid subscriptions and other revenue models, and why Substack might be the absolute worst place to build your writing career. Seriously.The main question we explore: what if your audience was your investor — and that was enough?We get into:What indie media actually means and why it's so important in today's fragmented landscapeWhy Lex hates Substack with the fire of a thousand suns and thinks everyone needs to get off... yesterday (including specific examples of how they steal your audience and revenue)The difference between a newsletter, an email list, and email marketing — and why we may be overcomplicating thingsPaid subscriptions vs. sponsorships vs. advertising: which revenue model fits your personality and daily workflow?How Lex sold her local politics newsletter, expanding our minds to what's possible when you have strong, valuable IPSubscription fatigue, the paywall police, and why patronage is not Netflix. The "dance for me because I paid you" mentality is tiredddHow to stay hopeful in the media biz when tech CEOs are devolving into oligarchy and software prices are spiking 200%If you've been questioning your presence on Substack, wondering whether anyone would actually pay for your writing, or assuming funding only happens to the Call Her Daddy's of the world — this episode is your invitation to look at the media landscape differently and build using your own playbook (and how to break a rule or two 😉).Connect with Lex:Grab 20% off your first year of Lex's Legends subscription right HERE! Revenue RulebreakerThreadsConnect with Chelsea:🌊 Audacity Waitlist - the pitching and visibility immersion for creative business owners🪄 Ultimate Pitch Kit waitlist ☄️ SUPERNOVA waitlist💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 Instagram🧵 ThreadsHelp run NFNTW: Your donations help cover costs of running the show; you can help fund NFTNW right HERE. If you're unable to donate financially, share it. It all adds up!Want to sponsor NFTNW? Email [email protected] to discuss partnership packages!

What would happen if you reached out to one person every day for 100 days? What if reaching out was a part of your daily practice, just like meditation or hitting the gym? And WHAT IF doors you couldn't even imagine opening flung open for you, all from ONE reach out?Carly Valancy, the QUEEN of reaching out, and is on today's ep to share all about the art of this powerful, life-changing practice.We get into:How technically we could be classified as competitors, but consider each other Power Rangers: part of the same squad, focused on similar missions, and going about it different waysWhy "if they wanted to, they would" is a phrase that needs to go in the trashcan ASAPThe real difference between pitching, reaching out, and clout chasing... and how to tell which one you're doingTreating your scariest asks like experiments Rejection as data, not a verdict... and how Carly turned a "no" from a bestselling author into a "yes" just by getting clearer (SO inspired by this story!)What happens if everyone says yes and you don't know what to do with yourself?Why "out of your league" is a story you're telling yourself, and how pedestalizing people actually dehumanizes themCollaboration > competitionIf you've been overthinking your website, your follower count, or your "readiness" before reaching out to someone, this episode is an invitation to stop preparing and just hit send. Life is about who you know, after all.Connect with Carly:Reach Out PartyWebsiteSubstackInstagramLinkedInTether ToolConnect with Chelsea:🌊 Audacity Waitlist - the pitching and visibility immersion for creative business owners🪄 Ultimate Pitch Kit waitlist ☄️ SUPERNOVA waitlist💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 Instagram🧵 ThreadsHelp run NFNTW: Your donations help cover costs of running the show; you can help fund NFTNW right HERE. If you're unable to donate financially, share it. It all adds up!Want to sponsor NFTNW? Email [email protected] to discuss partnership packages!

Xanthe Appleyard and I are BACK ON THE MIC breaking down August's biggest cultural headlines and zeitgeist moments...PLUS, we share 2 huge announcements up top! 👀August's topics ran the gamit:From Hayden Panettiere's passing, Ariana Grande and Alysa Liu stepping back from the spotlight, and more celebs taking mental health breaks, we have to wonder: what do celebs owe us? Why do we feel entitled to know everything about public figures? And where can we learn to set, enforce, and not cross boundaries, especially in the online space?Patronage vs. transactional support – from Diabolical Lies' maternity leave subscription controversy to reframing paid memberships as investment rather than instant-gratification transactions, it's time to talk about new ways to support creators!"More is more" posting mentality – Debunking the idea that posting 10x more = success; using data to find what actually drives revenue, and growing followers through podcasts/pitching instead of just posting moreDefining "enough" – Enough revenue, enough output, and prioritizing LIFE BUILDING over grinding it out at the content factory.Business model instability – Chasing followers as false security amid shifting launch models and buying habits.Imagination and dialing up the weirdness – period.Influencer industry news – Alix Earle's Netflix reality show, Alex Cooper shutting down Unwell Drinks, looking at their brand archetypes and what they represent, their media strategy, and what this all means at a macro level.We discuss everything through the lens of online leadership, digital behavior, and modern philosophy. You’ll leave with clear takeaways to move forward with, as well as a deeper understanding of how these topics are already impacting the conversations you’re leading, online and off. The internet is chaos — we'll help you make sense of it from our corner of it all ;)Connect with Xanthe:InstagramNEW Lifestyle InstagramSocial LifeWebsiteConnect with Chelsea:🌊 Audacity Waitlist - the pitching and visibility immersion for creative business owners🪄 Ultimate Pitch Kit waitlist ☄️ SUPERNOVA waitlist💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 Instagram🧵 ThreadsHelp run NFNTW: Your donations help cover costs of running the show; you can help fund NFTNW right HERE. If you're unable to donate financially, share it. It all adds up!Want to sponsor NFTNW? Email [email protected] to discuss partnership packages!

What if instead of booking a 90 min strategy intensive, $5000 VIP Day, or joining yet another mastermind on top of the four you've taken in the last two years... you went GREMLIN MODE?! What if going on side quests was the missing piece all along?!In today's episode, I chat with Alicia Koo of The Daily Atelier all about:Using silly goose energy as a strategic tool to sustain energy while carrying a heavy load... and where a stuffed frog comes into play (yes, really)Anger as a creative force vs. destruction. What's the difference between repression and diplomacy btw?How to stop the slam-dunk energy rampant on Threads and channel frustration into solutionsFAFO aka f*cking around and finding out... why is low-stakes exploratory research only for freshman in college? Let's reclaim that energy plzzz.Giving "branding" a rebrand. Put down the logos, fonts, and colors, and pick up a convicted opinion and a plan!What Japan's food-waste stickers or cheeky zines about AI use disarm people and drive real changeAudacity as boldness, not recklessnessIf you've been lost in the sauce, spiraling about how everything LOOKS, this episode is an invitation to shake up that energy and try a totally new approach focused on fun, play, and jester-like energy!Connect with Alicia:Find Your Brand's Soft Rebellion Free ResourceWebsiteInstagramThreadsConnect with Chelsea:🌊 Audacity Waitlist - the pitching and visibility immersion for creative business owners🪄 Ultimate Pitch Kit waitlist ☄️ SUPERNOVA waitlist💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 Instagram🧵 ThreadsHelp run NFNTW: Your donations help cover costs of running the show; you can help fund NFTNW right HERE. If you're unable to donate financially, share it. It all adds up!Want to sponsor NFTNW? Email [email protected] to discuss partnership packages!

If you're an introvert, Projector in Human Design, or subscribe to the "if they wanted to, they would" line of thinking, this episode is for you.Agata Serocka comes on the show today as a spokesperson for Projectors, who think reaching out, pitching, and asking for what they want isn't part of their strategy. We get into how to build a signal, BECOME the invitation, and not miss out on life's biggest opportunities by sitting in the passenger seat. We talk about:Reframing "waiting for the invitation" and how to move beyond the LITERAL interpretation to actively create conditions (podcasting, writing, showing up) that invite opportunities.Making outreach and pitching feel warm and not annoying AF. Building genuine rapport, finding connections, and doing research before reaching out vs. cold-pitching someone "hey girl haven't talked since we were 16 but would love for you to join my course! Link in bio!"Reframing labels (Projector, HSP, ADHD, rejection-sensitive) as data points to design a personalized, sustainable approach to visibility and business.Discernment over volume. How to say no to opportunities that don't fit, and trusting what's meant to work out, will! Making pitching fun and creative again. Gamify audacity by using playful approaches  like quests, small asks, and outlandish ideas to build confidence and make outreach sustainable vs. another "ugh, I have to do that?" choreConnect with Agata:The Culture of Unrushing Podcast on Spotify and AppleSubstackWaitlist to Agata's mastermindExperience Audit FreebieConnect with Chelsea:🌊 Audacity Waitlist - the pitching and visibility immersion for creative business owners🪄 Ultimate Pitch Kit waitlist ☄️ SUPERNOVA waitlist💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 Instagram🧵 ThreadsHelp run NFNTW: Your donations help cover costs of running the show; you can help fund NFTNW right HERE. If you're unable to donate financially, share it. It all adds up!Want to sponsor NFTNW? Email [email protected] to discuss partnership packages!

If I had to change my title, it would be Professional Shot Shooter. It's how I came up with the concept of Orbit Jumping. It's why I'm bullish on partnerships and collabs, it's why my business is running, profitable and energizing to this day, it's why I believe with every fiber of my being this is the answer to push back against Tech CEO Psychosis. We're in an era where we need humans banding together more than ever. You know this. I know this. We all do!!! And it all starts with moves being made. One shot. One ask. One request.This episode dives into nearly 20 ways to shoot your shot, ranging from asking your credit card to lower your interest rate to doing astrology readings at the local farmer's market to landing a byline in an indie magazine.The options are truly endless when you think outside the box! I've helped over 100+ clients realize the world is their oyster when they understand the art of shooting their shot. We'll be discussing alllllll the above inside the Shoot Your Shot Challenge going down August 25th - 27th (or 28th if you go VIP for more direct hot seat coaching!)The details:Runs August 25th - 27th (or 28th if you jump into the VIP Bonus Hot Seat Coaching Sesh!)$99 for VIP | $33 for the 3 day experienceAll calls recorded and sent as a replay if you can't make it liveMix of lessons + Q&A SHOTS WILL BE SHOT ;) Grab your spot RIGHT HEREConnect with Chelsea:🌊 Audacity Waitlist - the pitching and visibility immersion for creative business owners🪄 Ultimate Pitch Kit waitlist ☄️ SUPERNOVA waitlist💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 Instagram🧵 ThreadsHelp run NFNTW: Your donations help cover costs of running the show; you can help fund NFTNW right HERE. If you're unable to donate financially, share it. It all adds up!Want to sponsor NFTNW? Email [email protected] to discuss partnership packages!

The word "legacy" often triggers images of plaques, awards, or conversations people have when you're no longer in the room. It's thought of as something you leave behind.But Sienna J. Brown also believes it's a life well lived.In this episode, Sienna and I talk about:The Corporate America-to-entrepreneurship pipeline and why "take the leap and never looking back!!!" can actually be terrible advice (and how to build sustainably instead)Why the "Rags to Riches" narrative gets glamorized and why stability should actually be the Main Character insteadLegacy as a live well lived, not just the impact you make in your lifetime, and how the way you show up for your neighbor, grandma, and community matters just as much as professional milestones Sienna's "Life First Philosophy" and the life audit framework to design a business that actually matches how you feel AND what you wantIntentional time design and how to release the soul-sucking corporate conditioning of self-surveillanceThis episode was such an energizing reminder that the way your life FEELS is much more important than how it looks. And that's exactly what Sienna helps you do ;)Connect with Sienna:Join The Legacy LabFoundations for the Future Podcast on Spotify & AppleResourcesInstagramConnect with Chelsea:🌊 Audacity Waitlist - the pitching and visibility immersion for creative business owners🪄 Ultimate Pitch Kit waitlist ☄️ SUPERNOVA waitlist💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 Instagram🧵 ThreadsHelp run NFNTW: Your donations help cover costs of running the show; you can help fund NFTNW right HERE. If you're unable to donate financially, share it. It all adds up!Want to sponsor NFTNW? Email [email protected] to discuss partnership packages!

​Pitch Perfect lived a beautiful life. Bold. Daring. Courageous. Anyone who came across her path left more emboldened.It was rumored Pitch Perfect caused everyone around her to shoot their shots unapologetically, swing for the stars, and Orbit Jump to the moon, which resulted in almost shocking vision-board level opportunities.Podcast guests spots in abundance. Speaking collabs resulting in deep, genuine partnerships. Indie magazine features in the coolest niches. The opportunities overfloweth.​Pitch Perfect passed away peacefully in July of 2026. After a full and colorful life, she is survived by her heir... Audacity!!!In this episode, I reveal the name of the heir with absolute naming genius & strategist Katie Pannell of 26&thensome!We get into:Why I decided to rename Pitch Perfect, despite all its success and brand recognitionHow people perceive names and why it's so important to take your time naming thingsWhen is a good time to rename something? Why change a good thing?How I decided on Audacity (and why it scared me)Names that didn't make the cut (but will still use in my marketing)The emotional rollercoaster of naming precious thingsand SO much more in the world of naming, branding, and pivotingPerfect for anyone whose ready to kill their darlings.Connect with Katie:WebsiteInstagramThreadsConnect with Chelsea:🌊 Audacity Waitlist - the pitching and visibility immersion for creative business owners🪄 Ultimate Pitch Kit waitlist ☄️ SUPERNOVA waitlist💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 Instagram🧵 ThreadsHelp run NFNTW: Your donations help cover costs of running the show; you can help fund NFTNW right HERE. If you're unable to donate financially, share it. It all adds up!Want to sponsor NFTNW? Email [email protected] to discuss partnership packages!

Xanthe and I were frothing to record this State of the Internet July breakdown, because this was a TRUE "WTF is going on" month!Today's report includes:Our takes on Yesteryear by Caro Claire Burke — what was the book REALLY about? Tradwife influencers? Motherhood? Performing womanhood? We get into it and what it means in a broader cultural context.Is "influencer" an insult? We respond to this Reel by Levi Coralynn who addresses the topic, and dive into the overlap between influencers, capitalism and misogynyMeta Glasses — I share my theory about why these will never take off in the way Zuck deludes, Xanthe shares her take on how they've positioned these culturally, and we have to wonder... who (and what?) are these really for?Plus a slew of other AI headlines, including Substack's partnership with Pangram to detect AI writing, the backlash against Meta's gen AI tool, and how did we get to the point of "Claudefishing", where you can have Claude create videos of you from a single imageBIG ep today! We discuss everything through the lens of online leadership, digital behavior, and modern philosophy. You’ll leave with clear takeaways to move forward with, as well as a deeper understanding of how these topics are already impacting the conversations you’re leading, online and off. The internet is chaos — we'll help you make sense of it from our corner of it all.Connect with Xanthe:Join Social Life and use code CHELSEA for $10 off any membership! It's the social media + content strategy membership to stop second guessing your social media shit and become the sought-after creator you're meant to beCheck out Leadership Lifestyle Carousel Templates — strategic templates designed with your audience's reaction in mindLinks to all of Xanthe's offers: including Leisure Ethic Planner, Content Planner and moreConnect with Chelsea:🌊 Audacity Waitlist - the pitching and visibility immersion for creative business owners🪄 Ultimate Pitch Kit waitlist ☄️ SUPERNOVA waitlist💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 Instagram🧵 ThreadsHelp run NFNTW: Your donations help cover costs of running the show; you can help fund NFTNW right HERE. If you're unable to donate financially, share it. It all adds up!Want to sponsor NFTNW? Email [email protected] to discuss partnership packages!

I woke up thinking about the Latin root of "com" which sent me down a rabbit hole -- turns out, these used to be quite positive words back in the day.The words "comparison" and "competition" had a whole different meaning before capitalism and industrialization took over (shocking!) and in this ep, I'm exploring how we can get back to its original roots: "to make equal with" and "to strive together". Come with me as I make comparisons to modern day media powerhouses like Alex Cooper, how the Threads ick comes back around every season, the skill gap hamster wheel and more.I end with "The Parable of the Mexican Fisherman" which I think should be required reading for all entrepreneurs.This is for anyone in a comparison spiral, feeling exhausted by "competing" to scale, and who want to do business differently. Connect with Chelsea:🌊 Audacity Waitlist - the pitching and visibility immersion for creative business owners🪄 Ultimate Pitch Kit waitlist ☄️ SUPERNOVA waitlist💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 Instagram🧵 ThreadsHelp run NFNTW: Your donations help cover costs of running the show; you can help fund NFTNW right HERE. If you're unable to donate financially, share it. It all adds up!Want to sponsor NFTNW? Email [email protected] to discuss partnership packages!