Inspiring Conversations with Ashley Kirkwood of Speak Your Way To Cash®

Today we’d like to introduce you to Ashley Kirkwood.

Hi Ashley, so excited to have you with us today. What can you tell us about your story?
Sure! I started out as a trial lawyer at a large law firm making $300,000 a year. I was on the partner track, arguing major cases and doing the work I thought I was supposed to love. But even with all the external success, I felt confined. I knew I was meant to build something bigger—something that aligned with my voice, my faith, and my vision.

So, I took the leap and left. I launched my own law firm, where we didn’t just help people draft contracts—we helped them re-write the entire narrative around what they believed they could charge and how they positioned their services. That experience opened my eyes to something powerful: a lot of brilliant experts knew their craft, but they didn’t know how to sell it.

That’s what led me to create Speak Your Way To Cash®, a multimillion-dollar company that helps experts—lawyers, consultants, coaches, and creatives—increase their sales and land five- and six-figure contracts, especially with corporate clients. We teach people how to package their brilliance, pitch with authority, and finally earn what they’re worth.

Since starting, we’ve helped thousands of clients, landed multi-seven-figure deals, and secured a spot on the Inc. 5000 list. But more than anything, I’m proud that we’re changing lives by changing how experts sell. Because when you learn to speak your way to cash, you stop surviving and start scaling.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Definitely not a smooth road—and I wouldn’t want it any other way.

Sales came naturally to me. I’ve always been good at selling, especially when I believe in what I’m offering. But what took time—and a lot of trial and error—was simplifying the client journey. In the beginning, I had too many offers, too many directions, and not enough structure. I was passionate, but I was also doing the most. It took time to realize that clarity and focus scale faster than hustle alone.

Another challenge? I built this business from scratch with zero outside investment. For the first three years, we didn’t even have access to business credit. Every dollar we earned had to work overtime. There was no cushion—just vision, faith, and grind.

But those years taught me resilience. They taught me how to build lean, sell strategically, and value every client who came through the door. Now we run a multimillion-dollar firm, but those early years taught me lessons I carry into every decision we make.

The struggle wasn’t a sign to stop—it was training for the level we’re operating at now.

Appreciate you sharing that. What should we know about Speak Your Way To Cash® ?
At Speak Your Way To Cash®, we help experts turn their voice into their most powerful and profitable asset. We specialize in teaching speakers, coaches, consultants, and service providers how to increase their sales and land five- and six-figure contracts, especially with corporate clients. Whether they’re pitching Fortune 100 companies, government agencies, or top-tier universities, we show them how to package their expertise, position themselves as authorities, and sell with confidence.

We’re known for our straightforward, sales-driven training that delivers real results. Our clients secure transformational deals, raise their rates, and finally start charging what they’re worth.

What sets us apart is our unique blend of mindset, sales strategy, and high-ticket positioning—and the fact that we built this multimillion-dollar company from scratch, with no outside capital. We earned our place on the Inc. 5000 list by doing the real work, and now we teach others how to do the same.

Here’s how to plug into our world:
• Book: Want the blueprint? Start with the Speak Your Way To Cash® book: www.speakyourwaytocashbook.com
• Podcast: Weekly sales training, real stories, and big breakthroughs: Speak Your Way To Cash® Podcast
• Free Community: Join our free expert community here: https://www.skool.com/sywtc/about?utm_source=Youtube%20
• Live Event: Ready to scale? Come to Speak Your Way To Cash® Live: www.speakyourwaytocashlive.com

What I’m most proud of? We’ve built more than a business—we’ve created a movement. A movement that helps experts own their value, use their voice, and walk boldly in purpose. If you’re ready to sell smarter, speak with power, and scale faster—we’ve got you.

We’d love to hear about any fond memories you have from when you were growing up?
One of my favorite childhood memories is going to work with my dad. He’s a pastor, and I remember watching him serve people with so much passion and purpose. I’d sit in the front row during Bible study, or follow him around the church as he prepared for Sunday service. It wasn’t just about the preaching—it was the counseling, the leadership, the behind-the-scenes dedication.

Seeing him lead with integrity and faith planted the seeds of entrepreneurship and service in me early. It showed me what it looked like to pour into people and build something that impacts lives. Even now, so much of how I run my business—through values, purpose, and high service—was modeled for me by watching my dad do his work.

Contact Info:

• Website: https://Www.speakyourwaytocash.com
• Instagram: https://www.instagram.com/theashleynicoleshow/?hl=en
• Facebook: https://m.facebook.com/TheAshleyNicoleShow/
• Youtube: https://youtube.com/@theashleynicoleshow?si=lCyEnLaGQuK68Czx

 

Image Credits
Jason McCoy for static images
Shaun Washington for action shots