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Speak Your Way To Cash

Author: Ashley Kirkwood

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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 [email protected].
333 Episodes
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👉 Attend Black Women Sell Live: https://www.blackwomensellevent.comWould you shut down a business generating roughly $500,000 a year to turn it into something that could eventually scale nationwide?In this episode of The Make More Sales Show, Ashley coaches a New Jersey real estate attorney who started an after-school chess program in 2009 and grew it into approximately 50 schools.At roughly $10,000 per school, the model became a significant business.Then he made a major decision: he shut down the original operation and turned the concept into a franchise.Now the franchise infrastructure is built, but the next challenge is clear. He still needs his first franchisee.Connect with Ashley and Resources:✔️ Claim Your Free Speak Your Way to Cash® Book: https://www.speakyourwaytocash.com/BookPreviewLive✔️ Pitch Your Way to Cash® Membership: https://www.pitchyourwaytocash.com✔️ Millions From The Stage Waitlist: https://www.millionsfromthestage.com✔️ Black Women Sell Live: https://www.blackwomensellevent.com/✔️ Free Skool Community: https://www.skool.com/sywtc
👉 Attend Black Women Sell Live: https://www.blackwomensellevent.comWhat changes when your business is already making millions, but you’re still the person carrying too much of it?In this episode of The Make More Sales Show, Ashley coaches Shanice Anderson, an asset protection attorney, life insurance agent, real estate broker, and multi-million-dollar entrepreneur.Shanice’s business generated approximately $2 million last year and is on track to close at $8 million this year. But her biggest constraint isn’t demand. It’s letting go.At this level, the question is no longer just, “How many sales can I make?”It becomes, “How many sales can my team make without me?”What you’ll learn in this episode▪️ Why the founder’s role has to change once a company crosses seven figures▪️ How imposter syndrome can quietly limit your next revenue goal▪️ Why delegation becomes a requirement, not an option, at scale▪️ How paid advertising helped accelerate Shanice’s business growth▪️ Why knowing your organic messaging first can make your ads stronger▪️ How to build a rigorous hiring process for senior-level leaders▪️ Why job descriptions should filter out the wrong applicants▪️ How Loom videos can help screen leadership candidates▪️ Why candidates should prove their experience instead of simply talking about it▪️ How paid trial periods can protect you from emotional hiring decisionsConnect with Ashley and Resources Mentioned:✔️ Claim Your Free Speak Your Way to Cash® Book: https://www.speakyourwaytocash.com/BookPreviewLive✔️ Pitch Your Way to Cash® Membership: https://www.pitchyourwaytocash.com✔️ Millions From The Stage Waitlist: https://www.millionsfromthestage.com✔️ Black Women Sell Live: https://www.blackwomensellevent.com/
👉 Attend Land Corporate Client Using AI Summit: https://landcorporateclientsusingai.c...👉 Attend Black Women Sell Live: https://www.blackwomensellevent.comWhat 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 opportunityOne 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.
👉 Attend Land Corporate Client Using AI Summit: https://landcorporateclientsusingai.c...👉 Attend Black Women Sell Live: https://www.blackwomensellevent.comWhat 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 pageOne 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.
👉 Attend Black Women Sell Live: https://www.blackwomensellevent.comWhat 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 programsVanessa 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.
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