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Speak Your Way To Cash

Speak Your Way To Cash

By: Ashley Kirkwood
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Summary

 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.Copyright Ashley Kirkwood Economics
Episodes
  • 314: How To Impress Corporate Buyers Without Begging

    314: How To Impress Corporate Buyers Without Begging
    Apr 20 2026
    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/
    Show More Show Less
    1 hr and 13 mins
  • 313: How To Make Your First $1M Selling Services

    313: How To Make Your First $1M Selling Services
    Apr 19 2026
    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/
    Show More Show Less
    30 mins
  • 312: Land Big Clients Without More Credentials

    312: Land Big Clients Without More Credentials
    Dec 28 2025
    ATTEND OUR VIRTUAL 3-DAY EVENT & LEARN TO LAND BIG CLIENTS AS AN EXPERT: https://www.landbigclients.com/register

    Join our FREE Skool Community for Experts Looking To Sell More Services: https://rebrand.ly/SYWTCSkool

    If you’re a licensed, credentialed, or highly educated expert and your income still doesn’t reflect your expertise, this episode is for you. In this powerful conversation, Ashley Kirkwood breaks down how to land big clients without another degree, certification, or year of playing small. This is the exact system thousands of experts have used to move from hoping someone hires them to confidently closing $10K, $25K, and even $100K+ clients.

    Ashley pulls back the curtain on why experts with impressive credentials stay underpaid while lesser-qualified people win and, more importantly, how to fix it. If you sell services and want to position yourself for premium clients, this episode will change how you see your story, your offers, and your sales process.

    Here’s what Ashley walks you through in this episode:
    ▪️ Bullseye targeting and why talking to everyone is the fastest way to stay underpaid
    ▪️ How to uncover and leverage your unique selling power so you stand out in a crowded market
    ▪️ Why selling transformation instead of tasks instantly raises your price point
    ▪️ The real reason your offers are being compared to cheaper competitors and how to reposition them ▪️ How licensed and credentialed experts can sell ethically while protecting their reputation and license

    This episode is especially for experts who know they’re brilliant but feel overlooked, underestimated, or tired of watching less-qualified people get the opportunities they deserve. Ashley shows you how to stop hiding behind credentials and start using your voice, story, and experience to land clients who are ready to pay for real transformation.

    If this hits you in the chest, you already know this isn’t just strategy. It’s a shift.

    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/
    Show More Show Less
    29 mins
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