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

Today we’d like to introduce you to Ashley Kirkwood

Hi Ashley, thanks for joining us today. We’d love for you to start by introducing yourself.
I left a $300,000 partner-track law associate position to build my firm, Speak Your Way to Cash®. I thought being a lawyer was my dream job because I did love the traditional practice of law, but I didn’t love looking around and not seeing women who look like me at the very top. I also didn’t like the feeling that things hadn’t really changed much over a century in the law practice that I was particularly in. I was at a large law firm in Chicago and only 14% of all lawyers get to work at a firm the size of the firm that I was working at. It was not giving me the fulfillment that I now have. So, I’m just really grateful that I was able to start Speak Your Way to Cash®, a sales training firm that specializes in helping experts like me sell services to large companies.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
There has been some tough lessons. One was integrating my faith into my business because initially, I didn’t. However, I realized that 80% of my audience identifies as Christian, and their faith significantly influences their approach to goals. Inspired by Dr. Benjamin Hardy’s book “Be Your Future Self Now,” I understood that people’s views on God shape their views on success and effort. Not addressing faith in my business was a disservice to my clients, as it led them to believe that success might come without effort, which contradicts biblical teachings.

I began discussing the relationship between faith and work, emphasizing that while God blesses us, He also expects us to put in effort. Scriptures like Colossians 3:17 teach us to give our best in everything, acknowledging God’s role in our success. Jesus and his disciples were actively working, and this work ethic is crucial for achieving our goals.

Integrating faith into my coaching was a necessity to help my clients align their actions with their beliefs and realize their potential. This shift wasn’t just a choice; it was a response to a need for alignment between faith and professional growth.

Another challenge as a leader is that leaders aren’t afforded recovery time when going through things. So, what I learned is that the same way we’re aggressive about growing our businesses and getting new clients, is the same way we have to be aggressive about rest to make sure we have exactly what we need to serve at the highest level.

For me, I took a sabbatical in 2023-2024 and it was life-changing. I spent six weeks focusing on myself, my health, and my family, and it was incredibly refreshing. It made me realize how essential it is to take mental breaks because the work that I do involves a lot of mental energy. This experience was so valuable that I’m committed to making sabbaticals an annual part of my wellness plan.

We’ve been impressed with Speak Your Way to Cash®, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
Speak Your Way To Cash® is a dynamic sales training organization with a clear mission: to help diverse experts secure corporate contracts and master sophisticated sales processes. We do this through events, high-end coaching programs, courses, books, podcasts, social media, and even an invitation-only private mastermind group. The company was founded in 2019 and has rapidly evolved from a single event into a comprehensive platform for expert empowerment.

At the core of Speak Your Way To Cash® is our commitment to ensuring that no expert’s business falters due to a lack of understanding in sales and marketing. Our approach is rooted in no-nonsense training that exposes small businesses to the strategic thought processes of major corporations, bridging the gap between individual expertise and corporate success.

Our growth has been remarkable, driven by a multi-faceted approach to expert development. We have a thriving Facebook community of 12,000 speakers, coaches, entrepreneurs, and experts as well as our “Speak Your Way To Cash” podcast, which has become a go-to resource for aspiring and established experts alike.

By equipping experts with sophisticated sales processes and the confidence to pursue corporate contracts, Speak Your Way To Cash® is changing lives. We’ve had students book $10,000 corporate contracts RIGHT AT OUR EVENTS literally by taking what they learned that day, putting together an effective pitch, emailing it and receiving an offer.

One of the things we’re most proud of is being named to the Inc 5000 list this year ranking #370 in the nation and #14 in Georgia out of the 5000 fastest growing companies in America.

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Courtesy of Ashley Kirkwood

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