Cover image of show The Art of The Ask

The Art of The Ask

Podcast by Chelsea Riffe

English

Business

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About The Art of The Ask

Ever wonder what could happen if you just… asked? Like, REALLY asked— for the raise, the date, the discount, the collaboration, the last slice of pizza, or the life you actually want? Welcome to "The Art of the Ask," the limited series podcast hosted by Podcast Host, Strategist and Professional Shot Shooter Chelsea Riffe, here to help you stop overthinking, start pitching, and finally get what you want. Each episode, Chelsea unpacks the psychology, strategy, and sheer nerve it takes to ask for what you want—and flip your "who am I to ask?" to "why not me?!"

All episodes

13 episodes

episode Becoming Your Favorite Self to Unlock Visibility, Obsession as Strategy, and Soulmate Conspirators artwork

Becoming Your Favorite Self to Unlock Visibility, Obsession as Strategy, and Soulmate Conspirators

What if pitching wasn't about sending more emails — but about making more friends? Today, I sit down with Ashley B. Jones [https://www.instagram.com/ashley.b.jones/?hl=en] — Mentor, Artist, Philosopher, Psychic, and neurodivergent habit architect — to talk about what happens when you stop pitching for clout and start pitching for soulmate connections. We get into how Ashley sold out her program on TikTok in a week to fund joining Pitch Perfect (!) using her Favorite Self framework, why voice notes are an underrated visibility weapon, and how she walked into her fave brand's store in New York City and pitched them on hosting tarot readings in-store — because she had the audacity and finally had the framework to back it up. Ashley's visibility strategy after Pitch Perfect paid off! She: * Launched her podcast Effects of Butterflies [https://open.spotify.com/show/0XqLu3KuuSW6TEYspOkAbH?si=14566d69e6da4736] — something she'd been sitting on for three years — while still inside the program * Pitched herself to Cult Gaia (in person, cold, zero connections) and is now in talks with corporate about an in-store tarot event * Tripled her social media following practically overnight by going all in on one TikTok video * Built a constellation of collaborators, co-conspirators, and soulmate friends who are actively opening doors for each other We check in on what's been going on since Pitch Perfect, and I help her think through some visibility opportunities including: * Why leaning into voice and video is her highest-leverage pitching move * How to use your intellectual gifts as currency when asking for introductions * The "constellation collaboration" approach — identifying who's right in front of you and making the ask * What it looks and feels like to pitch from excitement vs. strategy — and why the former always wins CONNECT WITH ASHLEY: * Instagram [https://www.instagram.com/ashley.b.jones/?hl=en] * Podcast [https://open.spotify.com/show/0XqLu3KuuSW6TEYspOkAbH?si=14566d69e6da4736] * The Free 75-Minute Workshop: The Favorite Self Treasure Hunt [https://ashleybjones.myflodesk.com/favorite-self-treasure-hunt] * The Wishing Well 60-Min Reading [https://calendly.com/ashleybjones/the-wishing-well] If you liked this episode, you'll LOVE these: * Visibility on Your Own Terms with Ximena [https://open.spotify.com/episode/2gM7OKPlNPbtnny6gHzNAk?si=9hUtn7QXTkKSZePw2B-4fw] * How to Ask for Money [https://open.spotify.com/episode/5gEK2bvpGJihIosi57voPd?si=zBmu0fBwQyOl1O3ajuNtXA] * How to Handle Rejection When Asking for What You Want [https://open.spotify.com/episode/5mCiy6xBeV4SxaOgLWjKaj?si=Bf3p94KVRYOUnfG2AP-hBA] Here's my ask for you! * DM me on IG [https://www.instagram.com/chelseariffe/?hl=en]  or email team@chelseariffe.com and tell me - what have you asked for recently, and what were the results? * Follow this podcast, rate, review, and  - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed!

6 May 2026 - 41 min
episode Visibility on Your Own Terms & The Power of Slow, Nurturing Connections with Ximena artwork

Visibility on Your Own Terms & The Power of Slow, Nurturing Connections with Ximena

Are you a dinner party person or a house party person? The reason I ask? It shows you a LOT about how you relate to pitching and visibility. 👀 Today, I sit down with Ximena [https://www.instagram.com/__ximenaximena__/?hl=en], everyone's favorite eco-philosopher, to discuss the power of human relationships and how it 10X your visibility, how to reframe pitching when it feels icky, and why it's completely okay to pitch more intimately and focus on depth vs. volume. Ximena's visibility strategy after Pitch Perfect [https://www.chelseariffe.com/pitch-perfect] paid off! She: * Published in an English-language magazine she loved, with no portfolio or large following — and became the only non-US contributor * Grew from teaching 5 philosophy lessons online to 40+ in a year purely through connection * Built Rooted Impact [https://www.arootedimpact.com/] (her signature philosophy program) and attracted students who joined without ever seeing her face or hearing her teach * Landed guest speaking opportunities and other visibility wins despite a "small following" We check in to see what's been going on since Pitch Perfect, and I help her move through some visibility blocks including: * Reframing pitching — helping her see it as connection-building rather than the cold corporate sales she dreaded from her past job * Identifying her visibility style — through the "dinner party vs. house party" conversation, I help her realize she's an intimate, slow-nurturing connector (a superpower!) * Diversified visibility strategies — like placing classified ads in newsletters and low-lift ways to reach new audiences without the relationship-building overhead * Reframing her "limitation" — helping her see that her bilingual perspective and unique POV are advantages, not obstacles, when pitching If you liked this episode, you'll LOVE these: * Pitching a Cinematic Universe and Decentering Your Social Following [https://open.spotify.com/episode/4wAh1vI22jbaBfbXcpGP54?si=3s86mqUkQW2iMczh1qZsog] * How to Ask For What You Want If You Have Imposter Syndrome [https://open.spotify.com/episode/4gJ8vR90F3Bf2DGoyXMKx6?si=gW6cZUHWRn6Ky7HeieDCng] * How to Handle Rejection When Asking For What You Want [https://open.spotify.com/episode/5mCiy6xBeV4SxaOgLWjKaj?si=HCllNy_CR92HJqF9bOlZPg] Connect with Ximena: * All links + offers [https://bio.site/ximenaximena?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGnLkmfcC5aQM8kKJJqk5KOP-sZ8oSVAGxHmIGPJwUodp1gC1jsrQKJfewSMKE_aem_yGC-dZ-QhxZR0LNHDwySMg] Here's my ask for you! * DM me on IG @chelseariffe [https://www.instagram.com/chelseariffe/?hl=en] or email team@chelseariffe.com  and tell me - what have you asked for recently, and what were the results? * Follow this podcast, rate, review, and  - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed!

29 Apr 2026 - 36 min
episode Pitching a Cinematic Universe and Decentering Your Social Following with Ayu Sutriasa artwork

Pitching a Cinematic Universe and Decentering Your Social Following with Ayu Sutriasa

So many of us hold ourselves back from pitching because we don't have a massive social media following, digital presence or booming online audience. This imaginary math that your following = more bookings is costing you serious opportunities, from both a visibility AND financial standpoint. But what you offer, your lens, and your PRESENCE are worth gold compared to an IG following. Your cinematic universe is what people are captivated by, and that's what you should center in your pitches! Today, Ayu from Astral Pathways joins us to discuss what happens when pitching feels less like strategy and more like texting a friend. We get into: * how pitching is really just reaching out to people whose worlds you already want to be in * why discernment matters more than volume — especially when you're a single mom running a business led by intuition * what it actually means to combine orbits and why visibility compounds when you stop cold pitching strangers She also shares some exciting wins since Pitch Perfect [https://www.chelseariffe.com/pitch-perfect], like: * how she pitched herself to an astrologer with 10x her following — and landed a soulmate-level client within a week * how a voice note (not a five-paragraph essay) got her paid to teach her signature writing workshop inside someone else's program * how she pitched a local magazine editor IRL over coffee — and landed the column Then, we move into visibility coaching where I help Ayu understand why her follower count is genuinely the least interesting thing about her pitch, the language shift that turns "I'm an astrologer" into a cinematic universe someone wants to live in, and why her most magnetic opportunities are already inside the orbits she's built — including the creatives who are waiting to find out their archetype. If you liked this episode, you'll LOVE these: * ⁠⁠How To Ask for Clients⁠⁠ [https://open.spotify.com/episode/7EKHzeF2YKkJT8SKnIZIMg?si=CPkPdaZVQyKEaPJ72NVOkA] * ⁠⁠How To Handle Rejection⁠⁠ [https://open.spotify.com/episode/5mCiy6xBeV4SxaOgLWjKaj?si=-ZlCLl44RD-toQMllhKETA] * ⁠⁠⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠ [https://open.spotify.com/episode/7lew5qCNPiij1rmrZW7IUG?si=mWhGN9C4QoOuvAV1-lB_0g] Connect with Ayu: * Instagram [https://www.instagram.com/astralpathways/] * Threads [https://www.threads.com/@astralpathways] * Book a Creative Archetype Immersion [https://ayu-astral-pathways.myflodesk.com/creative-archetype] * Sign up for the next FREE co-writing session [https://ayu-astral-pathways.myflodesk.com/co-write] Here's my ask for you! * DM me on IG ⁠⁠⁠@chelseariffe⁠⁠⁠ [https://www.instagram.com/chelseariffe/?hl=en] or email ⁠⁠team@chelseariffe.com⁠⁠ [team@chelseariffe.com] and tell me - what have you asked for recently, and what were the results? * Follow this podcast, rate, review, and ⁠⁠⁠tag me on socials⁠⁠⁠ [https://www.instagram.com/chelseariffe/?hl=en] - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed! Now go shoot your shot!

24 Apr 2026 - 43 min
episode Relationship-First Pitching, Anti-Clout Chasing and Knocking on Your Internet Neighbor's Door to Increase Visibility with Giana Cesaria artwork

Relationship-First Pitching, Anti-Clout Chasing and Knocking on Your Internet Neighbor's Door to Increase Visibility with Giana Cesaria

The biggest myth around increasing your visibility is thinking it's about VOLUME: blasting out 100 emails per week, nonstop appearances, and jumping on as many platforms as you possibly can squeeze into your schedule. But you're not an octopus with nine brains and eight arms. Also, you're not a clout-chaser. Giana Cesaria [https://www.instagram.com/giana.cerasia/?hl=en], anthrophilosopher and teacher of systems, conditioning and rewilding, joins The Art of the Ask today to discuss relationship-focused asks. We get into: * how pitching is just a fancy way of saying "interacting" or having conversations * the concept of "power with vs. power over" * being in true community and amplifying each others' work She also shares some surprising insights, like: * pitching as go-to market research * how she used the skills inside Pitch Perfect [https://www.chelseariffe.com/pitch-perfect] to help transition out of her corporate career * how the conversations inside the program helped shape her 7 month apprenticeship [https://ravish.life/apprenticeship], one of her deepest offers Then, I put on my Visibility Thinking Cap to help Giana understand where her message will land best, the language to use to stand out in a sea of pitches, and why her most fruitful opportunities are right in front of her, including the incredible community [https://www.notion.so/Free-Women-s-Circle-29439179192f80a3ba9fed0395f30f8f] she's built. Ready to work on your own visibility strategy and get into the rooms where your message is needed most through strategic pitching? Pitch Perfect [https://www.chelseariffe.com/pitch-perfect] is for you! Doors open until May 8th, 2026. If you liked this episode, you'll LOVE these: * ⁠How To Ask for Clients⁠ [https://open.spotify.com/episode/7EKHzeF2YKkJT8SKnIZIMg?si=CPkPdaZVQyKEaPJ72NVOkA] * ⁠How To Handle Rejection⁠ [https://open.spotify.com/episode/5mCiy6xBeV4SxaOgLWjKaj?si=-ZlCLl44RD-toQMllhKETA] * ⁠⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠ [https://open.spotify.com/episode/7lew5qCNPiij1rmrZW7IUG?si=mWhGN9C4QoOuvAV1-lB_0g] Connect with Giana: * Instagram [https://www.instagram.com/giana.cerasia/] * Kitchen Table Sauce Podcast [https://open.spotify.com/show/6RA1zd2Oyp756h4X2bzhB3?si=a6bdb1abbc084021 ] * Apprenticeship [https://ravish.life/apprenticeship] starting May 2026! Here's my ask for you! * DM me on IG ⁠⁠@chelseariffe⁠⁠ [https://www.instagram.com/chelseariffe/?hl=en] or email ⁠team@chelseariffe.com⁠ [team@chelseariffe.com] and tell me - what have you asked for recently, and what were the results? * Follow this podcast, rate, review, and ⁠⁠tag me on socials⁠⁠ [https://www.instagram.com/chelseariffe/?hl=en] - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed!

22 Apr 2026 - 33 min
episode Becoming Your Own PR Agent, Paid Speaking Spots and How to Pitch Yourself as a Multi-hyphenate with Abbi Miller artwork

Becoming Your Own PR Agent, Paid Speaking Spots and How to Pitch Yourself as a Multi-hyphenate with Abbi Miller

If you find pitching to be worse than the chores your parents gave you when you were eight years old and fantasize about outsourcing it to a glamorous PR agency, thinking you'll get featured in Forbes or Vogue, become famous, and stack cold-hard cash simply from your newfound visibility...come sit. We need to talk. Abbi Miller from WorkWomb [https://www.workwomb.com/] joins us today to share why becoming her own PR agent after Pitch Perfect [https://www.chelseariffe.com/pitch-perfect] was the key to unlocking the visibility goals she craved, including getting PAID for her POV. Psst, she had a PR team handle her pitching before Pitch Perfect and shares why that didn't pan out as imagined... You'll also hear how she's: * Become more discerning about the pitches she responds to, realizing many are lazy, low-effort and impersonal (I explain why this happens!) * Made time to do her own pitching despite a busy schedule AND being a mama I help Abbi navigate a burning question she had: how do you effectively pitch your wide range of expertise and services, without feeling like you have to narrow down to just a few specific topics to copy/paste into each pitch? I put on my Visibility Thinking Cap and shared how she can: * Create playlists of past podcast episodes organized by theme/worldview rather than specific topics * Pitch the broader concepts and frameworks she's passionate about, and let the podcast host help shape the specific talking points * Let go of the idea that you'll only have 3-5 angles to ever choose from; the talking points will always evolve, but your worldview is the larger container to hold it all! The key was helping Abbi leverage her existing content and expertise in a way that feels authentic, rather than feeling boxed in to a narrow pitch. Ready for your own visibility glow-up, where you'll learn how to position your expertise, stand out in a sea of vanilla pitches, escape your echo chamber, and create visibility that compounds? Pitch Perfect [https://www.chelseariffe.com/pitch-perfect] is for you! If you liked this episode, you'll LOVE these (seriously): * How To Ask for Clients [https://open.spotify.com/episode/7EKHzeF2YKkJT8SKnIZIMg?si=CPkPdaZVQyKEaPJ72NVOkA] * How To Handle Rejection [https://open.spotify.com/episode/5mCiy6xBeV4SxaOgLWjKaj?si=-ZlCLl44RD-toQMllhKETA] * ⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠ [https://open.spotify.com/episode/7lew5qCNPiij1rmrZW7IUG?si=mWhGN9C4QoOuvAV1-lB_0g] Connect with Abbi: * Founder of ⁠Workwomb⁠ [https://workwomb.com/]™ * ⁠Instagram⁠ [https://www.instagram.com/workwomb/?hl=en] * ⁠Podcast⁠ [https://www.workwomb.com/podcast] Here's my ask for you! * DM me on IG ⁠@chelseariffe⁠ [https://www.instagram.com/chelseariffe/?hl=en] or email team@chelseariffe.com [team@chelseariffe.com] and tell me - what have you asked for recently, and what were the results? * Follow this podcast, rate, review, and ⁠tag me on socials⁠ [https://www.instagram.com/chelseariffe/?hl=en] - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed!

9 Apr 2026 - 30 min
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