311: 5 Hard Truths About Scaling

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Speak Your Way To Cash

Ashley Kirkwood

314 episodes

1 week ago

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.

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311: 5 Hard Truths About Scaling

Speak Your Way To Cash

31 minutes

1 week ago

311: 5 Hard Truths About Scaling

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What if the very habits that helped you hit six or seven figures are now quietly sabotaging your business, draining your energy, and pushing away your best team members? In this powerful episode of the Speak Your Way to Cash® Podcast, Ashley Kirkwood breaks down the hardest truths about scaling a business that most entrepreneurs never hear until it’s too late.

Drawing from her journey from a $300K corporate law career to building a multi–seven-figure company recognized on the Inc. 5000 list, Ashley shares what actually happens behind the scenes when your business starts to grow fast. This conversation is real, unfiltered, and exactly what seasoned experts, coaches, consultants, and speakers need if they want to scale sustainably without losing themselves in the process.

In this episode, Ashley pulls back the curtain on:
▪️ Why the clients who helped you reach six figures may be the very ones holding you back from seven and eight
▪️ The uncomfortable truth about marketing budgets, paid ads, and why organic growth alone is not predictably scalable
▪️ How doing “everything yourself” keeps you trapped and why systems, sales processes, and delegation unlock real freedom
▪️ The leadership mistake most founders make when their team underperforms and how to fix it
▪️ Why burnout is not a badge of honor and how protecting your health is a revenue strategy, not a luxury

This episode is especially for high-achieving entrepreneurs who feel the pressure to perform, lead, and grow while secretly wondering how long they can keep this pace. Ashley shares personal stories, real numbers, and practical frameworks to help you scale your business without burnout, chaos, or resentment.

If you’re serious about business growth, leadership development, predictable revenue, and building a company that doesn’t collapse when you step away, this episode will shift how you think about scaling forever.

🎧 Listen, take notes, and get ready to lead at a higher level.

🔗 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/