Your Legacy is a Life Well Lived with Sienna J. Brown

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:Join the SHOOT YOUR SHOT CHALLENGE Aug 25-27th!Enroll in Audacity for $900 off til Aug 27th!Get on the Ultimate Pitch Kit waitlist 🪄☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 IG: ⁠@chelseariffe⁠🧵 Threads: @chelseariffeSupport 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:Join the SHOOT YOUR SHOT CHALLENGE Aug 25-27th!Enroll in Audacity for $900 off til Aug 27th!Get on the Ultimate Pitch Kit waitlist 🪄☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 IG: ⁠@chelseariffe⁠🧵 Threads: @chelseariffeSupport 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:Join the SHOOT YOUR SHOT CHALLENGE Aug 25-27th!Enroll in Audacity for $900 off til Aug 27th!Get on the Ultimate Pitch Kit waitlist 🪄☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 IG: ⁠@chelseariffe⁠🧵 Threads: @chelseariffeSupport 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:Join the SHOOT YOUR SHOT CHALLENGE Aug 25-27th!Enroll in Audacity for $900 off til Aug 27th!Get on the Ultimate Pitch Kit waitlist 🪄☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 IG: ⁠@chelseariffe⁠🧵 Threads: @chelseariffeSupport 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!

Back with another off the cuff vlog today, and this time, I share a smoothie of thoughts, including:The power of constraints boosting imaginationHow I produce more coherent work with constraintsMy experience flying Business Class from Copenhagen to Lisbon and the glaring spotlight of class systems in travelWhat Business Class and the coaching space have in commonWhat "classes" are we creating in our own ecosystems and are we happy about it? Is there anything we can change?Why I'd never run a 4000+ person program and why I never desire toHow I make my business work focusing on intimacy and build that into my business modelWHEW, a lot can go down in 10 mins! Let me know your thoughts in the Spotify comment section, leave a written review, and slide in my DMs (on Threads)!Connect with Chelsea:Join the SHOOT YOUR SHOT CHALLENGE Aug 25-27th!Enroll in Audacity for $900 off til Aug 27th!Get on the Ultimate Pitch Kit waitlist 🪄☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 IG: ⁠@chelseariffe⁠🧵 Threads: @chelseariffeSupport 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!

It's the weekend. I'm in Copenhagen. And I think I need Digital Nomad Rehab, a center for people who want to settle down but addicted to traveling.This is an off the cuff vlog sharing what's swirling around in my brain, including:How my Europe Summer is goingEmotional whiplash of starting over every few monthsWhy it's so hard to commit to one placeSome financial advice nuggets sprinkled inGeneral musings about my lifestyle and what's nextWe're having a Letting It Rip Summer, so let me know what ya think of this style!Connect with Chelsea:Join the SHOOT YOUR SHOT CHALLENGE Aug 25-27th!Enroll in Audacity for $900 off til Aug 27th!Get on the Ultimate Pitch Kit waitlist 🪄☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 IG: ⁠@chelseariffe⁠🧵 Threads: @chelseariffeSupport 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 with your State of the Internet June report, where we try to make sense of WTF is going on in the internet each month.Today's report includes:Jessi Jean's viral Yap Challenge and million-dollar launches — what makes offers go viral? How much did the role of FOMO play here? Plus, pricing strategy, timing, and the difference between viral content and viral offers. (Xanthe and I also share what we think our own viral offers could be!)Desire over data — Why do some creators like Kareem from Subway Takes deliberately ignore data? When are metrics actually useful vs. an armor? How much do you create for the love of the game over the numbers?Flodesk's AI Studio rollout — AI really is taking over and its latest target is Flodesk, a company near and dear to Xanthe's heart that's prompted quite the moral dilemma. Will we use it? For what? What does this mean for tech companies en masse, including the "smaller" ones?Plus, low-effort posting, personal diary content, and the surge in nostalgia  — is this all in resistance to AI?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:Grab the Leadership Lifestyle Templates - strategic Carousel templates designed WITH your audience's reaction in mindJoin Social Life - the social media support system that solves your content execution problem, keeps your creative spark alive, and meaningfully grows your business — without asking you to post more, perform harder, or please the petty algorithmInstagramLove You To The Core PodcastLinks to all offers, including Leisure Ethic Planner, Content Planner and moreConnect with Chelsea:Join the SHOOT YOUR SHOT CHALLENGE Aug 25-27th!Enroll in Audacity for $900 off til Aug 27th!Get on the Ultimate Pitch Kit waitlist 🪄☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 IG: ⁠@chelseariffe⁠🧵 Threads: @chelseariffeSupport 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!

My financial situation this year is giving... erratic. I share every detail in today's ep and why I'm not calling 911 yet.After YEARS of steady monthly recurring revenue that paid all my basic expenses and then some, I changed my business model in late 2025, which resulted in seeing income numbers I haven't seen since year 1 of starting my business. I'm talking "how am I going to afford all this month's expenses?" kind of numbers.At first, I was chill, leaning on my savings and systems. Then, I freaked out. HOW TF DID THIS HAPPEN?! I thought I mastered budgeting and forecasting??I share the full story, what I did to turn the ship around, and share practical advice on what to do when you're in a similar sitch.Episodes mentioned: How I Paid off $8K of Debt in One MonthHow I Planned My Sabbatical (So You Can Too) - Saving, Taking 2 Months Off and Why It’s Freaking Me Out☎️ Have more questions? Leave a voicemail on the hotline and I'll answer in the next ep!Connect with Chelsea:Join the SHOOT YOUR SHOT CHALLENGE Aug 25-27th!Enroll in Audacity for $900 off til Aug 27th!Get on the Ultimate Pitch Kit waitlist 🪄☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 IG: ⁠@chelseariffe⁠🧵 Threads: @chelseariffeSupport 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!

We're back from the break room to discuss the second installment of this shitshow known as the Summer House Reunion.In Part 2, Shelly and I get into: WTF happened in that break room? Amanda and West's off-stage debrief sent chills down our spine. Baby voices. Fishing for reassurance. West coaching her like a PR handler. HUH??Is West Wilson a Companion Robot? The manchild said barely four sentences on stage, nodded along to Dara calling him out??, and then went home to yap with false BDE on his podcast. What IS West's strategy here?Amanda's post-Summer House reality check. Lost brand deals, a swimwear collab that's likely dunzo, and fully tied to a brand she said was never really fully invested in. What does the path "back" even look like — and does staying with West make it impossible?The Kyle and Amanda deep dive. Were they ever truly in love, or were they business partners who stayed together for the show? We unpack four years of no intimacy, the cheating admissions, Kyle's deflection Olympics, and what on earth did they think therapy was for?The "Carl's a Mess" ad moment. Was it harmless fun or did Amanda have a point? Also — did everyone forget about her Buffalo Wild Wings ad throwing shade at Kyle??? Because we didn't.Dara's speech. 10/10. No notes.What we need from Part 3: Andy asking Amanda and West to name what they actually like about each other. The Ben and Amanda Italy commentary that flew by way too fast. Jesse getting more airtime. Just a few things on our wishlist!We are SAT for Part 3 and cannot wait to see who gets asked back... filming starts next month! P.S. We get into convos like this inside POPCORN CLUB, my free monthly movie + TV debrief meetup. Next one is Weds June 10th at 11am EST to go IN on the three part Summer House Reunion. Come join us!Connect with Shelly:InstagramConnect with Chelsea:Join the SHOOT YOUR SHOT CHALLENGE Aug 25-27th!Enroll in Audacity for $900 off til Aug 27th!Get on the Ultimate Pitch Kit waitlist 🪄☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 IG: ⁠@chelseariffe⁠🧵 Threads: @chelseariffeSupport 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 for May's State of the Internet debrief, where we try to make sense of WTF is going on in the internet each month.Today's report includes:Spotify's AI-generated podcast announcement  — what does this mean for podcast hosts? Why do tech CEOs feel SO out of touch with these decisions? Plus why reading T&C's is IMPERATIVE these days and what to do with this info.Hot Chef Threads drama — IYKYK, and if you don't, we'll explain. Do we "owe" our audiences anything after we make our personal lives very public? Is it okay to paywall your vulnerability? How can we be more mindful of the dynamic we play in our online communities?The Met Gala x tech billionaires funding the arts — is this a good or bad thing in the long-run? Why are tech bros so obsessed with inserting themselves in fashion right now? What amount of money makes people bend on their morals/values and why?Everlane gets bought up by SHEIN  — WTF. Period.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:InstagramLove You To The Core PodcastLife of the Party  — enrolling right now! Use code NOTES for $100 off!Links to all offers, including Leisure Ethic Planner, Content Planner, Social Life membership and moreConnect with Chelsea:Join the SHOOT YOUR SHOT CHALLENGE Aug 25-27th!Enroll in Audacity for $900 off til Aug 27th!Get on the Ultimate Pitch Kit waitlist 🪄☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 💻 Website📜 Footnotes newsletter filled with rabbit holes, zeitgeist synthesis and more💌 The Art of the Ask Podcast📱 IG: ⁠@chelseariffe⁠🧵 Threads: @chelseariffeSupport 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!