The Art of The Ask

Chelsea Riffe
  • 5.0 (5)
  • Entrepreneurship
  • Updated Weekly

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?!"

  1. May 6

    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 — 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 — something she'd been sitting on for three years — while still inside the programPitched herself to Cult Gaia (in person, cold, zero connections) and is now in talks with corporate about an in-store tarot eventTripled her social media following practically overnight by going all in on one TikTok videoBuilt 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 moveHow to use your intellectual gifts as currency when asking for introductionsThe "constellation collaboration" approach — identifying who's right in front of you and making the askWhat it looks and feels like to pitch from excitement vs. strategy — and why the former always wins CONNECT WITH ASHLEY: InstagramPodcastThe Free 75-Minute Workshop: The Favorite Self Treasure Hunt The Wishing Well 60-Min Reading If you liked this episode, you'll LOVE these: Visibility on Your Own Terms with XimenaHow to Ask for MoneyHow to Handle Rejection When Asking for What You Want Here's my ask for you! DM me on IG  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!

    41 min

  2. Apr 29

    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, 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 paid off! She: Published in an English-language magazine she loved, with no portfolio or large following — and became the only non-US contributorGrew from teaching 5 philosophy lessons online to 40+ in a year purely through connectionBuilt Rooted Impact (her signature philosophy program) and attracted students who joined without ever seeing her face or hearing her teachLanded 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 jobIdentifying 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 overheadReframing 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 FollowingHow to Ask For What You Want If You Have Imposter SyndromeHow to Handle Rejection When Asking For What You Want Connect with Ximena: All links + offers Here's my ask for you! DM me on IG @chelseariffe 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!

    36 min

  3. Apr 24

    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 inwhy discernment matters more than volume — especially when you're a single mom running a business led by intuitionwhat 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, like: how she pitched herself to an astrologer with 10x her following — and landed a soulmate-level client within a weekhow a voice note (not a five-paragraph essay) got her paid to teach her signature writing workshop inside someone else's programhow she pitched a local magazine editor IRL over coffee — and landed the columnThen, 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 Clients⁠⁠⁠⁠How To Handle Rejection⁠⁠⁠⁠⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠ Connect with Ayu: InstagramThreadsBook a Creative Archetype ImmersionSign up for the next FREE co-writing session Here's my ask for you! DM me on IG ⁠⁠⁠@chelseariffe⁠⁠⁠ 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 ⁠⁠⁠tag me on socials⁠⁠⁠ - 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!

    44 min

  4. Apr 22

    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, 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 conversationsthe 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 researchhow she used the skills inside Pitch Perfect to help transition out of her corporate careerhow the conversations inside the program helped shape her 7 month 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 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 is for you! Doors open until May 8th, 2026. If you liked this episode, you'll LOVE these: ⁠How To Ask for Clients⁠⁠How To Handle Rejection⁠⁠⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠ Connect with Giana: InstagramKitchen Table Sauce PodcastApprenticeship starting May 2026! Here's my ask for you! DM me on IG ⁠⁠@chelseariffe⁠⁠ 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 ⁠⁠tag me on socials⁠⁠ - 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!

    33 min

  5. Apr 9

    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 joins us today to share why becoming her own PR agent after 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 topicsPitch the broader concepts and frameworks she's passionate about, and let the podcast host help shape the specific talking pointsLet 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 is for you! If you liked this episode, you'll LOVE these (seriously): How To Ask for ClientsHow To Handle Rejection⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠ Connect with Abbi: Founder of ⁠Workwomb⁠™⁠Instagram⁠⁠Podcast⁠ Here's my ask for you! DM me on IG ⁠@chelseariffe⁠ 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 ⁠tag me on socials⁠ - 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!

    31 min

  6. Apr 2

    What I've Asked For in 2026 (Cash, Discounts and Payment Plans)

    Your fave pop-up podcast is BACK for Season 2! Kicking off today with an update on everything I've asked for, including: an extended payment plan from my tax team (and the unexpected surprise they hit me with)cash from someone I barely knew an indie bookstore to buy my books from mea few more requests that resulted in huge wins At some point, it was admirable to do everything alone, right? But in this era, if we want to get off the capitalist hamster wheel, we need to get comfortable asking people for support. If we want true community, intimacy, and partnership, stretching your ASKING muscle is essential. So, what are you asking for this week?! If you liked this episode, you'll LOVE these: ⁠How to Ask for Clients⁠⁠How to Ask for Money⁠⁠How to Ask For Something with No Track Record, Portfolio or Massive Social Following⁠ Pitch Perfect Spring 2026 is enrolling right now! Get $300 off until April 13th. Doors close May 8. Here's my ask for you! DM me on IG  or email  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! NOW GO ASK FOR WHAT YOU WANT!

    28 min

  7. 10/31/2025

    How to Ask For Clients

    What if you could just... ask someone to be your client? I'm so serious. Put down the automated funnels. Say goodbye to the free webinars. Break up with the 14-email nurture sequence. In this episode, I'm walking you through how I slid in someone's DMs that turned into a 2 year partnership and over $60K invested, and used the same strategy to have my biggest launch of Pitch Perfect ever. By the way, Pitch Perfect Spring enrollment for Spring is opening soon. Get on the waitlist HERE. If you liked this episode, you'll LOVE these: ⁠The Witch Wound - Taking Down the Patriarchy Through Putting Yourself Out There⁠⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠⁠Rejection Won't Kill You - What It Means & How to Deal With It⁠⁠Selling Without Social Media⁠ Here's my ask for you! DM me on IG ⁠@chelseariffe⁠ 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 ⁠tag me on socials⁠ - 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!

    51 min

  8. 10/19/2025

    How to Ask for What You Want if You Have Imposter Syndrome

    Let's address the elephant in this visibility glow-up room: imposter syndrome. In this episode, I'm breaking down what an imposter actually is (spoiler: unless you're actively scamming people out of their life savings or the Tinder Swindler, you're fine) and why feeling intimidated just means you're expanding. I'll walk you through the real mindset shifts and practical moves that'll help you own your expertise... no more $5K+ certifications required. I'm pulling from my own messy AF business moments, podcasting fumbles, and what I've seen working with clients to show you why most of us feel like frauds when we're literally just... growing. You'll learn how to build ACTUAL self-trust through prep, being completely honest about what you know (and don't), and really embodying your thing, so you can stop enrolling in 8 courses every quarter to "be ready". What you're going to hear today: Why the literal definition of "imposter" proves you're off the hook (unless you're Anna Delvey reading this...)The difference between feeling intimidated and actually being unqualified (no, they're not the same)How to swap "I don't know enough" for "I can figure this out or ask someone"What embodiment actually looks like in real life, and how to know if you've got itWhy DOING the thing creates confidence way faster than THINKING / spiraling about itHow to use "borrowed confidence" when you're too in your head to just askWhy putting people on pedestals and over-apologizing wreck good collaborationThe reframe that helps you trust your clients' ability to make their own decisions My Biggest Takeaways: Everyone is winging it. Yes, even them.Certifications don't give you confidence. Reps do.You're not an imposter, you're in a season of growth Stop assuming your audience is as harsh as your inner critic. They showed up for a reason, even if it's to "be in your energy" (because YES, many people DO just want to be around you) Episodes mentioned today: Taylor Swift, Bad Bunny and Modern Day TitansHow To Ask for Something with No Track Record, Portfolio or Massive Social Following If you liked this episode, you'll LOVE these: ⁠The Witch Wound - Taking Down the Patriarchy Through Putting Yourself Out There⁠⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠⁠Rejection Won't Kill You - What It Means & How to Deal With It⁠ Here's my ask for you! DM me on IG ⁠@chelseariffe⁠ 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 ⁠tag me on socials⁠ - 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!

    44 min
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5
out of 5
5 Ratings

About

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?!"

Information

  • Creator
    Chelsea Riffe
  • Years Active
    2025 - 2026
  • Episodes
    13
  • Rating
    Explicit
  • Copyright
    © Chelsea Riffe
  • Show Website
    The Art of The Ask

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