Speak Your Way To Cash

Ashley Kirkwood
  • 4.8 (79)
  • 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. 4d ago

    She Made $343K in Insurance—But Still Felt Behind

    👉 Attend Land Corporate Client Using AI Summit: https://landcorporateclientsusingai.c... 👉 Attend Black Women Sell Live: https://www.blackwomensellevent.com What if you’re making progress in business—but still feel like you should be further ahead? In this episode of The Make More Sales Show, Ashley coaches Moon Thomas, owner of Thomas Family Agency, a full-service brokerage focused on health and wealth products including life insurance, health insurance, Medicare, and annuities. Over the last 12 months, Moon wrote more than $343,000 in personal production. But despite the progress she’s made, she still feels the pressure of looking at her annual goals and wondering whether she’s moving fast enough. Ashley’s response? Entrepreneurship is NOT school. You don’t have to move from first grade to second grade to third grade in business. With the right information, strategy, execution, and focus, growth can happen much faster than you expect. In this coaching session, Ashley breaks down: ▪️ Why you need to know exactly which products are generating your revenue ▪️ How to identify and double down on your top-performing offers ▪️ Why some products should become upsells instead of your primary marketing focus ▪️ How to protect the revenue already working while testing a new direction ▪️ When it makes sense to pivot from one primary business model to another ▪️ The difference between a bookkeeper, accountant, tax strategist, and CFO ▪️ Why every investment in your business should produce an asset or lesson ▪️ How to stop replaying mistakes and start extracting value from them ▪️ Why your current position does not determine where you’ll finish the year ▪️ How Ashley thinks about “receipts versus rhetoric” when making decisions ▪️ Why entrepreneurs need both faith and practical execution ▪️ How sales, knowledge, and learning become part of stewarding your opportunity One of the biggest lessons from this conversation is that being behind your original timeline does not automatically mean you’re failing. Businesses do not grow in perfectly straight lines. Sometimes what took you an entire year before can eventually happen in a single month. The goal is to understand your numbers, protect what is already working, learn from your mistakes, and keep planting the right seeds. Energy high. Excuses low. Results and financial examples discussed in this episode are individual examples and are not guarantees of future performance. Business results vary based on execution, market conditions, experience, strategy, and other factors.

  2. Sep 9

    Pro Athlete Wants 30 Real Estate Deals a Month—Here’s the Lead Strategy

    👉 Attend Land Corporate Client Using AI Summit: https://landcorporateclientsusingai.c... 👉 Attend Black Women Sell Live: https://www.blackwomensellevent.com What would it take to go from chasing real estate leads outbound to having qualified property sellers come directly to you? In this episode of The Make More Sales Show, Ashley coaches a professional athlete and real estate investor who wants to scale his business to 30+ property deals per month. His strategy is focused on finding distressed property owners, helping them understand their options, and potentially purchasing properties directly from sellers who need to move quickly. But there’s one major constraint: LEADS. Right now, much of his process depends on outbound prospecting through county records and manually identifying potential sellers. Ashley breaks down how he could flip that model by creating an inbound lead-generation system designed to identify and qualify motivated sellers before he ever gets on the phone. They discuss: ▪️ How to calculate the number of conversations needed to hit your monthly deal goal ▪️ Why your sales math should determine your advertising budget ▪️ How to create a simple one-liner people immediately understand ▪️ Why distressed sellers may respond better to discreet qualification funnels ▪️ How quizzes can qualify real estate leads before a sales conversation ▪️ Using paid advertising to generate inbound seller opportunities ▪️ How to determine what you’re willing to pay per qualified conversation ▪️ Measuring advertising ROI based on deals closed and potential property equity ▪️ How to identify which geographic markets are producing your best opportunities ▪️ Why you should outsource repetitive outbound prospecting once the process works ▪️ How a professional athlete can leverage an existing personal brand to grow a separate business ▪️ Why your company should have its own focused social media presence ▪️ How referral incentives can activate your existing audience ▪️ Building a personal brand around multiple pillars without turning your entire platform into a real estate page One of the biggest lessons from this coaching session is simple: If you want 30 deals every month, you first need to know exactly how many qualified conversations it takes to produce those 30 deals. Once you understand that math, you can build your marketing, advertising, lead qualification, and sales systems around the goal. The conversation also shows how athletes can leverage the discipline, visibility, and audiences they’ve already built to create opportunities beyond sports. Results, advertising returns, deal volume, and financial examples discussed in this episode are illustrative and are not guarantees. Actual results depend on market conditions, execution, advertising performance, deal quality, financing, and other factors.

  3. Sep 9

    She Builds $25M Neighborhoods—Now She Wants to Monetize Her Expertise

    👉 Attend Black Women Sell Live: https://www.blackwomensellevent.com What happens when people are already asking you to teach them what you know—but you haven’t built the offer yet? In this episode of The Make More Sales Show, Ashley coaches land developer Vanessa Cole, who develops neighborhoods and generates between $10M–$25M in sales volume through her real estate business. Selling houses isn’t Vanessa’s problem. The opportunity is monetizing the expertise people are already asking her for after speaking engagements. Ashley breaks down how Vanessa could turn her knowledge into a scalable education and advisory business without distracting herself from the land development business already making her money.  They discuss: ▪️ How to create an 80% passive / 20% hands-on coaching model ▪️ Why a $997–$1,997 course could serve as the entry-level offer ▪️ How to structure premium strategic advisory offers at $5K+ per month ▪️ Why your highest-level access should be reserved for qualified buyers ▪️ How cash + equity deals can create additional upside ▪️ Why you should sell your course before spending months recording it ▪️ How to use your first live students to create the course content ▪️ Why your warm audience should convert before you spend heavily on cold ads ▪️ How to test a webinar three times before automating it ▪️ How to build an email list from an engaged social media following ▪️ What questions to ask leads before launching your offer ▪️ How AI can become the “brain” behind an on-demand course ▪️ Why contracts, disclaimers, and FTC compliance matter when selling coaching programs Vanessa already has an engaged audience of approximately 90,000 Instagram followers and people regularly asking how they can learn her real estate development process. Now the question becomes: how do you turn that demand into an offer that scales without sacrificing the business that created the expertise in the first place? This coaching session shows exactly how Ashley would approach it. Results discussed in this episode are examples and projections, not guarantees. Business results vary based on execution, market conditions, audience, pricing, advertising, and other factors.

  4. Aug 9

    326: How to fill 100 event seats without guessing

    👉 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 you stop hoping people buy tickets and start activating the audience you already have. Ashley’s first event made $600 with 10 people in a WeWork. Years later, she sold just under half a million dollars in services from the stage at an event with about 75 people in the room. In this episode, Ashley breaks down how to get your first 100 people to your event by identifying the real buyers in your audience, sorting them by buying signals, and sending personal invitations that actually start conversations. If you want to host profitable live events, retreats, intensives, or sales events, this is the event marketing system you need before you post another generic flyer. What you'll learn in this episode ▪️ Why filling the room is usually a segmentation problem, not just a reach problem ▪️ The 3-tier audience sort Ashley uses to find the people most likely to buy tickets ▪️ How to spot buyer signals inside your email list, DMs, CRM, and past purchases ▪️ The one-paragraph invitation structure that turns warm audience members into ticket buyers ▪️ Why referrals can help you fill the room with better buyers, not just more people Why this matters now Events are powerful, but they are also risky when you don’t know who should be in the room. If you’re a coach, consultant, speaker, expert, or service provider, your first 100 attendees may already be closer than you think. You just need the right message, the right segmentation, and the courage to personally invite the people who are most likely to say yes. 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

  5. Aug 2

    325: How to keep webinar buyers without begging

    👉 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 people leave before you ever make the offer. You have about seven minutes to prove your webinar is worth staying for—and most hosts waste that time reading their bio, fixing slides, and asking people to drop their city in the chat. In this episode, Ashley breaks down what to do in the first 30 minutes of your webinar so you close the retention gap, keep attention, and build the emotional and psychological contract that makes people want to stay. You’ll learn how to open with urgency, build authority without reading your resume, and prime the room to buy before the pitch ever starts. What you'll learn in this episode ▪️ The 90-second buyer open Ashley uses instead of “drop your city in the chat” ▪️ Why the first 30 minutes of your webinar determine whether people stay for the offer ▪️ How to build authority with sacrifice, proof, and vulnerability instead of reading your bio ▪️ The psychology of yes framework: personal belief, community worth, and business worth ▪️ Why your webinar should feel more like a performance than a slide presentation Why this matters now If you’re hosting webinars, masterclasses, virtual events, or conversion talks, your audience is deciding fast whether you are worth their attention. The right webinar opening can help coaches, consultants, speakers, and experts keep more people engaged long enough to hear the offer and understand the transformation. 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

  6. Jul 26

    324: How to get 1,000 webinar registrants without posting all day

    👉 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 truth about getting people into your webinar. If you want 1,000 webinar registrants but you’re not posting five times a day, you need more than hope and organic content. You need a marketing system. In this episode, Ashley breaks down how she went from webinars with 20 to 28 people registered to thousands of registrants by using paid advertising, direct outreach, influencer marketing, and show-up campaigns. This is for experts who want more of the right people in the room so they can sell the offer that changes their clients’ lives. What you'll learn in this episode ▪️ Why paid advertising helped Ashley go from 28 registrants to thousands ▪️ How to use organic content to decide which ads to run ▪️ The direct outreach math behind getting 1,000 webinar registrants ▪️ Why influencers and niche pages work differently when promoting your event ▪️ The three email campaigns you need after someone registers for your webinar Why this matters now A webinar is not just a registration page. It’s a full marketing system that has to attract the right people, remind them to show up, and move them toward the offer. If you’re a coach, consultant, speaker, expert, or service provider, this episode will help you think more strategically about webinars, masterclasses, challenges, summits, and virtual events. 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

  7. Jul 19

    323: How to build a $25K offer without guessing

    👉 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 you stop selling tiny offers and start building something that matches your expertise. Ashley’s first coaching program was $30 a month. Today, Speak Your Way To Cash® is a multi-million dollar company with premium offers, six-figure offers, and a clear system for helping real experts outsell the fake ones. In this episode, Ashley breaks down how to build your first $25K coaching or consulting offer by starting with the problem, packaging the solution, naming the pieces, proving the value, and selling it through events. If you’re a doctor, lawyer, consultant, coach, speaker, or credentialed expert, this is the offer-building strategy you need before you raise your prices. What you'll learn in this episode ▪️ How Ashley went from a $30/month coaching offer to premium offers and a multi-million dollar company ▪️ Why you may need to start lower—but should never stay there without testing, proof, and results ▪️ The problem-to-offer chart Ashley uses to build premium coaching, consulting, and corporate offers ▪️ How to name your offer pieces so they feel specific, valuable, and impossible to compare ▪️ Why events, masterclasses, and group sales calls can help you sell one-to-many instead of one-to-one Why this matters now If you’re an expert selling services, your offer cannot just be “I’m good at what I do.” Buyers need to understand the problem, the transformation, the deliverables, the value, and the reason your solution is worth the investment. A premium offer is not just a higher price. It is a better-built case. 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

  8. Jul 12

    322: How to handle objections 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 why you freeze when the buyer says, “I need to think about it.” Most objections are not the real objection. They’re the polite version of what the buyer is actually feeling. In this episode, Ashley breaks down how to handle sales objections around time, money, and worthiness without pressure, panic, or discounting your offer. You’ll learn how to ask better questions, uncover what the buyer really means, and respond like a trusted advisor instead of a desperate seller. What you'll learn in this episode ▪️ The objection iceberg method Ashley uses to hear what buyers really mean ▪️ What to say when someone says, “I don’t have time” ▪️ How to handle “I can’t afford it” without shaming, pushing, or discounting ▪️ Why worthiness objections show up as timing, money, or confidence issues ▪️ How to answer objections with your offer instead of arguing with the buyer Why this matters now If you sell coaching, consulting, speaking, corporate training, or premium services, objections are not the end of the conversation. They’re the beginning of the real one. When you learn how to ask consultative sales questions, you can close more aligned buyers and serve people with truth instead of pressure. 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

See All (331)

4.8
out of 5
79 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
    331
  • Rating
    Clean
  • Copyright
    © Copyright Ashley Kirkwood
  • Show Website
    Speak Your Way To Cash

You Might Also Like