Speak Your Way To Cash

Ashley Kirkwood
  • 4.8 (78)
  • Business
  • Updated Weekly

Ashley Kirkwood from the Speak Your Way To Cash podcast will share business tactics, tips, and strategies from her own experience and interviewing experts in the speaking, sales and entrepreneurship space. Ashley has built several successful businesses including her law firm and speaking business, where she speaks to colleges and corporations on confidence, leadership, and student success. Her signature speech is entitled, The Currency of Confidence. Ashley has spoken to audiences with as many as 4,000 people in attendance. She has helped several universities reinvigorate student engagement and enjoys speaking to law schools and sharing her story, which is chronicled in her book, The Law School Hustle. Ashley hosts an event called, Speak Your Way To Cash for speakers looking to enhance their speaking business and learn knock-it-out-of-the-park sales strategies! Email Ashley at admin@passionpurposeandpaychecks.com.

  1. 17h ago

    320: How to raise your rates without feeling ready

    👉 Land Corporate Clients Using AI for just $17 — register here: https://www.aicorporatesaleslab.com/ 👉 Let Ashley coach you in person for 3 days at Black Women Sell Live: https://www.blackwomensellevent.com/ 👉 Join our FREE Skool community for experts who want to sell more services: https://www.skool.com/sywtc This one is for the expert who knows they’re undercharging. If you keep saying you’ll raise your rates next quarter, next year, or after one more certification, this episode is your sign. Ashley breaks down why “charging your worth” is the wrong frame—and why your rate is a requirement. You’ll learn how to run a rate audit, stop negotiating with yourself before the buyer even objects, and price your services based on transformation instead of fear. What you'll learn in this episode ▪️ Why Ashley says she’ll never charge her worth—but her rate must be paid ▪️ The four-part rate audit most consultants, coaches, and speakers never run ▪️ How to research 20 people in your niche so you stop pricing in the dark ▪️ Why exposure pricing and comparative pricing keep experts underpaid ▪️ How to know whether a free speaking opportunity is actually a marketing opportunity Why this matters now If you sell professional speaking, coaching, consulting, or corporate training, the wrong rate can quietly drain your revenue and confidence. Nobody can pay you the rate you won’t say, and the right buyers can’t find you if you keep pricing for the wrong room. Connect with Ashley and Resources Mentioned: ✔️ Claim Your Free Speak Your Way to Cash® Book: https://www.speakyourwaytocash.com/BookPreviewLive ✔️ Pitch Your Way to Cash® Academy: https://www.pitchyourwaytocash.com ✔️ Attend Millions From The Stage: https://www.millionsfromthestage.com ✔️ Attend Black Women Sell Live: https://www.blackwomensellevent.com/ ✔️ Free Skool Community: https://www.skool.com/sywtc

    10 min

  2. Jun 21

    319: How to finally lead through tough times without spiraling

    👉 Land Corporate Clients Using AI for just $17 — register here: https://www.aicorporatesaleslab.com/ 👉 Let Ashley coach you in person for 3 days at Black Women Sell Live: https://www.blackwomensellevent.com/ 👉 Join our FREE Skool community for experts who want to sell more services: https://www.skool.com/sywtc Here’s how Ashley got back in her zone. If life, health, team pressure, and revenue pressure have ever hit at the same time, this episode will feel personal. Ashley shares how an unexpected fibroid diagnosis, surgery recovery, a second sickness, team challenges, and a revenue dip pushed her into a funk—and what she did to get out. This is a CEO mindset reset for entrepreneurs who need to keep leading when life does not pause for business. The goal is not to pretend everything is fine. The goal is to act like the CEO you are until your mood catches up with your actions. What you'll learn in this episode ▪️ The exact list Ashley builds when she needs to get back into her optimal state ▪️ Why health, team, and revenue disruptions hit harder when you’re leading the business ▪️ How to stop a negative spiral without pretending you’re not frustrated ▪️ Why prayer, sunlight, clean food, workouts, and discipline became Ashley’s reset pattern ▪️ How to let your mood catch up with your actions when you don’t feel ready yet Why this matters now Entrepreneurship doesn’t give you a clean calendar for sickness, family, team issues, or economic pressure. If you’re a founder, consultant, coach, speaker, or expert building a revenue-generating business, this episode will help you lead through hard seasons with faith, discipline, and emotional honesty. Connect with Ashley and Resources Mentioned: ✔️ Claim Your Free Speak Your Way to Cash® Book: https://www.speakyourwaytocash.com/BookPreviewLive ✔️ Pitch Your Way to Cash® Academy: https://www.pitchyourwaytocash.com ✔️ Attend Millions From The Stage: https://www.millionsfromthestage.com ✔️ Attend Black Women Sell Live: https://www.blackwomensellevent.com/ ✔️ Free Skool Community: https://www.skool.com/sywtc

    19 min

  3. Jun 14

    318: How to sell $50K offers without discounting

    👉 Land Corporate Clients Using AI for just $17 — register here: https://www.aicorporatesaleslab.com/ 👉 Let Ashley coach you in person for 3 days at Black Women Sell Live: https://www.blackwomensellevent.com/ 👉 Join our FREE Skool community for experts who want to sell more services: https://www.skool.com/sywtc Here’s why your offer may not be too expensive. If you’ve raised your prices, heard “no” a few times, and quietly drifted back down, the problem may not be your market. It may be your price anchoring. In this episode, Ashley breaks down how the first number your buyer sees changes the way they process your premium offer. You’ll learn how to reveal your price in a way that makes the investment feel clear, strategic, and worth serious consideration. What you'll learn in this episode ▪️ Why buyers may pay 346 more for the same thing depending on the first number they see ▪️ The four anchors Ashley uses before revealing a premium offer price ▪️ How to position a $50K engagement as an investment instead of an expense ▪️ The 3-step price reveal that makes your offer accessible without discounting ▪️ Why your buyer may be comparing your offer to a $300 class, an $8,500 coach, or a $200K degree Why this matters now If you sell coaching, consulting, corporate training, or high-ticket services, your price does not exist in a vacuum. Price anchoring helps your buyer compare the investment to the right reference point so they can make a better decision with a CEO mindset. Connect with Ashley and Resources Mentioned: ✔️ Claim Your Free Speak Your Way to Cash® Book: https://www.speakyourwaytocash.com/BookPreviewLive ✔️ Pitch Your Way to Cash® Academy: https://www.pitchyourwaytocash.com ✔️ Attend Millions From The Stage: https://www.millionsfromthestage.com ✔️ Attend Black Women Sell Live: https://www.blackwomensellevent.com/ ✔️ Free Skool Community: https://www.skool.com/sywtc ⏱ CHAPTERS 00:00 - Why your offer is not too expensive 01:06 - The MIT study behind price anchoring 02:06 - Why price sequence changes perception 02:39 - The four anchors to use before your price reveal 03:05 - Career, time, and expense anchors 04:30 - How CEOs should evaluate business investments 04:58 - The 3-step price reveal 05:41 - The $1,500 airport shoe reframe 06:44 - The anchor line Ashley uses from the stage 09:21 - Why experts need to get paid well

    12 min

  4. Jun 7

    317: How to finally sell $10K offers without pressure

    👉 Land Corporate Clients Using AI for just $17 — register here: https://www.aicorporatesaleslab.com/ 👉 Let Ashley coach you in person for 3 days at Black Women Sell Live: https://www.blackwomensellevent.com/ 👉 Join our FREE Skool community for experts who want to sell more services: https://www.skool.com/sywtc Here’s the sales shift most experts are missing. If your premium offer pitch is all about what people will gain, you may be leaving the strongest part of the decision out. In this episode, Ashley breaks down how to sell premium offers by ethically showing the cost of inaction. You’ll learn why buyers don’t just need to see the upside. They need to understand what staying the same is really costing them. What you'll learn in this episode ▪️ Why gain-heavy pitches sound good but still make buyers ask for “time to think about it” ▪️ The 2.25x loss-aversion principle Ashley uses to explain why people move faster when they understand what delay costs ▪️ The $50K-to-$4,200 reframe that makes the status quo feel measurable, not vague ▪️ How to talk about loss ethically without manipulating, fear-mongering, or exaggerating ▪️ Why your best pitch may need more grounded stories, data, and cost-of-delay examples Why this matters now Whether you sell corporate training, consulting, coaching, or high ticket services, your buyer is already doing math in their mind. This episode will help you make that math visible so your next webinar, discovery call, or premium offer pitch gives people both sides of the decision: what they gain when they act and what they lose when they wait. Connect with Ashley and Resources Mentioned: ✔️ Claim Your Free Speak Your Way to Cash® Book: https://www.speakyourwaytocash.com/BookPreviewLive ✔️ Pitch Your Way to Cash® Academy: https://www.pitchyourwaytocash.com ✔️ Attend Millions From The Stage: https://www.millionsfromthestage.com ✔️ Attend Black Women Sell Live: https://www.blackwomensellevent.com/ ✔️ Free Skool Community: https://www.skool.com/sywtc ⏱ CHAPTERS 00:00 - Why your pitch may be selling the wrong way 00:37 - Why gain-heavy offers land soft 00:52 - The ethical way to show the cost of inaction 01:40 - The 2.25x loss-aversion multiplier 02:25 - The $50K gain-to-loss reframe 03:15 - Why the weight-loss example makes it click 04:09 - The business cost of waiting 05:06 - Ashley’s early business lesson on delay 06:35 - Belief, knowledge, and invisible problems 07:54 - Scripts, client stories, and typical results

    19 min

  5. Jun 1

    316: The Exact 4-Part Posting System To Land Clients

    👉 Land Corporate Clients Using AI for just $17 — register here: https://www.aicorporatesaleslab.com/ 👉 Let Ashley coach you in person for 3 days at Black Women Sell Live: https://www.blackwomensellevent.com/ 👉 Join our FREE Skool community for experts who want to sell more services: https://www.skool.com/sywtc Here’s how to turn your LinkedIn profile into a buyer-ready sales asset. LinkedIn is packed with corporate decision makers, but most experts are still using it like a digital business card. You post a few times a month, the same 12 people like it, and you wonder why the leads aren’t coming. In this episode, Ashley breaks down how to use LinkedIn and AI to build credibility, create content faster, and start real conversations with buyers. Your profile should not just look professional. It should help corporate clients trust you before they ever reply. What you’ll learn in this episode ▪️ The LinkedIn profile rewrite Ashley says every expert needs before pitching corporate buyers ▪️ How to build a 4-post-a-week content engine AI can help draft in 20 minutes ▪️ Why your headline should sell the buyer’s outcome, not list your titles ▪️ The three-touch DM sequence Ashley recommends before making a direct offer ▪️ The voice note question that can turn a cold connection into the right conversation Corporate clients are checking you before they answer you. If your LinkedIn profile is quiet, vague, or built for peers instead of buyers, you’re giving decision makers a reason to hesitate. This episode helps speakers, coaches, consultants, and service providers use LinkedIn for corporate sales without sounding like a bot. Connect with Ashley and Resources Mentioned: ✔️ Claim Your Free Speak Your Way to Cash® Book: https://www.speakyourwaytocash.com/Bo... ✔️ Pitch Your Way to Cash® Academy: https://www.pitchyourwaytocash.com ✔️ Attend Millions From The Stage: https://www.millionsfromthestage.com ✔️ Attend Black Women Sell Live: https://www.blackwomensellevent.com/ ✔️ Free Skool Community: https://www.skool.com/sywtc

    13 min

  6. May 25

    315: How to get corporate referrals without feeling pushy

    👉 Land Corporate Clients Using AI for just $17 — register here: https://www.aicorporatesaleslab.com/ 👉 Let Ashley coach you in person for 3 days at Black Women Sell Live: https://www.blackwomensellevent.com/  👉 Join our FREE Skool community for experts who want to sell more services: https://www.skool.com/sywtc Now let’s turn referrals into a system. Your referrals should not be random. In this episode, Ashley breaks down a 30-day referral system that helps experts use AI, warm relationships, and simple follow-up to create more corporate sales conversations without feeling pushy. If your revenue feels lumpy, this gives you a practical way to stop waiting and start asking. Referrals aren’t just nice to have — they can become a repeatable sales process. What you'll learn in this episode ▪️ How to use AI to sort your warm network into four referral buckets in 20 minutes ▪️ The four-sentence referral ask that makes the request clear and low-pressure ▪️ Why referred customers can have higher lifetime value and lower churn ▪️ How to run a 30-day sprint that turns warm introductions into sales conversations ▪️ When to ask for referrals so your clients are most likely to say yes Why this matters now: Corporate sales gets easier when trust enters the room before you do. Whether you’re a coach, consultant, speaker, or expert selling B2B services, this episode shows you how to combine referrals and cold outreach so you’re not depending on random miracles every quarter. Connect with Ashley and Resources Mentioned: ✔️ Claim Your Free Speak Your Way to Cash® Book: https://www.speakyourwaytocash.com/BookPreviewLive ✔️ Pitch Your Way to Cash® ACADEMY Use code "PODCAST" FOR A DISCOUNT: https://www.pitchyourwaytocash.com ✔️ Millions From The Stage: https://www.millionsfromthestage.com ✔️ Black Women Sell Live: https://www.blackwomensellevent.com/ ✔️ Free Skool Community: https://www.skool.com/sywtc ⏱ CHAPTERS 00:00 - Why referrals should not be random 00:33 - The problem with lumpy referral revenue 01:09 - The 30-day sprint that can replace months of cold outreach 02:00 - The Wharton study every expert should know 02:41 - The four-bucket referral audit using AI 03:36 - The four-sentence referral ask 04:12 - The 30-day referral sprint 05:02 - Teresa’s warm-intro success story 06:01 - When to ask for referrals 07:43 - Why Ashley waited to ask for help

    12 min

  7. Apr 20

    314: How To Impress Corporate Buyers Without Begging

    Want me to coach you for three days for just $97?? Attend the Land Big Clients Challenge: www.landbigclients.com If you’ve been wondering how to close corporate contracts and actually get corporate decision-makers to take you seriously… this episode is the one you’ve been waiting for. Because listen—corporate buyers aren’t just looking for someone “good.” They’re looking for someone who makes them feel confident, protected, and prepared. In this powerful conversation, Ashley sits down with Attorney Steffany Cunningham, General Counsel (North America) at National Express, who oversees a team of 30 and manages a multi-million dollar vendor budget. She’s worked with top-tier vendors, hired them, fired them, kept them, and referred them. And she’s sharing the real behind-the-scenes truth about what makes a vendor stand out. If you want to win in corporate, you’ve got to know how corporate leaders think. And that’s exactly what this episode delivers. ▪️ What corporate decision-makers REALLY look for when hiring vendors ▪️ How to pitch corporate contracts without sounding “new” ▪️ The #1 mistake vendors make when they don’t understand the business ▪️ How to stay top of mind after you’ve already landed the contract ▪️ How strong vendors help executives look like rockstars to their boards ▪️ What it takes to build trust with senior leaders and get repeat work This conversation is for experts, consultants, speakers, coaches, and service providers who want to land corporate speaking opportunities, secure corporate consulting contracts, and position themselves as the kind of vendor corporations keep on speed dial. Because here’s the truth: People see your services through the lens you give them. So if you present yourself like a beginner, they’ll treat you like one. And we’re done doing that. Guest Spotlight: Attorney Steffany Cunningham Steffany Cunningham is General Counsel (North America) at National Express, a major transportation organization serving school districts across the U.S. and Canada. She leads legal strategy, manages vendor partnerships, and supports large-scale operations across North America. Modern Counsel Connect with Ashley and Resources Mentioned: ✔️ Claim Your Free Speak Your Way to Cash® Book: https://www.speakyourwaytocash.com/BookPreviewLive ✔️ Waitlist for Black Women Sell Live: https://www.blackwomensellevent.com/ ✔️ Pitch Your Way to Cash® Membership: www.pitchyourwaytocash.com ✔️ Join the Speak Your Way to Cash® Skool Group: https://www.skool.com/sywtc ✔️ Join the Speak Your Way to Cash® Facebook Group: https://www.facebook.com/groups/SpeakYourWayToCash/

    1h 13m

  8. Apr 19

    313: How To Make Your First $1M Selling Services

    Want me to coach you for three days for just $97?? Attend the Land Big Clients Challenge: www.landbigclients.com If you’re trying to make more money selling your services but you’re feeling stretched thin, overwhelmed, and like you’re doing “too much” for too little… this episode is going to hit you right in the chest (in a good way). Ashley Kirkwood joins David Shands on the Social Proof Podcast and delivers a masterclass on what actually moves revenue: simplifying your offer, choosing ONE dominant sales channel, and selling in a way that makes your business easier to scale. This conversation is real, practical, and exactly what you need if you’re going into a new year and saying, “2025 has to look different.” Here’s what you’ll learn in this episode: ▪️ How to make more money by selling fewer things (and why most business owners stay stuck trying to sell 10 offers at once) ▪️ The Dominance Framework: how to scale by focusing on one sales channel, one marketing channel, one vision, and one offer ▪️ Why your content shouldn’t be built for likes, and what it should be built for instead: leads + sales ▪️ The difference between active selling vs. passive selling (and why you need more active selling if you want consistent revenue) ▪️ How to increase revenue even with a small audience by offering a high-result program instead of low-cost products ▪️ What to do when you set a revenue goal and don’t hit it (hint: you don’t “wait for next month”… you make an audible) Ashley also answers real-time audience questions and breaks down how to structure offers for: ✅ people selling e-books or memberships ✅ people building thought leadership content ✅ people with multiple skills who need to get focused now If you’ve been saying: “I need to make money, but I don’t have a big email list…” “I’m posting consistently but it’s not turning into sales…” “I feel like I’m doing everything and nothing is working…” This episode is your sign to simplify and scale.  Connect with Ashley and Resources Mentioned: ✔️ Claim Your Free Speak Your Way to Cash® Book: https://www.speakyourwaytocash.com/BookPreviewLive ✔️ Waitlist for Black Women Sell Live: https://www.blackwomensellevent.com/ ✔️ Pitch Your Way to Cash® Academy: www.pitchyourwaytocash.com ✔️ Join the Speak Your Way to Cash® Skool Group: https://www.skool.com/sywtc ✔️ Join the Speak Your Way to Cash® Facebook Group: https://www.facebook.com/groups/SpeakYourWayToCash/

    30 min
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4.8
out of 5
78 Ratings

About

Ashley Kirkwood from the Speak Your Way To Cash podcast will share business tactics, tips, and strategies from her own experience and interviewing experts in the speaking, sales and entrepreneurship space. Ashley has built several successful businesses including her law firm and speaking business, where she speaks to colleges and corporations on confidence, leadership, and student success. Her signature speech is entitled, The Currency of Confidence. Ashley has spoken to audiences with as many as 4,000 people in attendance. She has helped several universities reinvigorate student engagement and enjoys speaking to law schools and sharing her story, which is chronicled in her book, The Law School Hustle. Ashley hosts an event called, Speak Your Way To Cash for speakers looking to enhance their speaking business and learn knock-it-out-of-the-park sales strategies! Email Ashley at admin@passionpurposeandpaychecks.com.

Information

  • Creator
    Ashley Kirkwood
  • Years Active
    2019 - 2026
  • Episodes
    322
  • Rating
    Clean
  • Copyright
    © Copyright Ashley Kirkwood
  • Show Website
    Speak Your Way To Cash

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