• WHAT WE DO
  • CONNECT WITH US
  • PRODUCTS
  • EVENTS
  • MEET THE FOUNDERS
  • WHAT WE DO
  • CONNECT WITH US
  • PRODUCTS
  • EVENTS
  • MEET THE FOUNDERS

AT SPEAK YOUR WAY TO CASH®, WE TEACH CONSULTANTS, SPEAKERS, TRAINERS, ATTORNEYS, ENTREPRENEURS, AND OTHER PROFESSIONALS TO PACKAGE, PITCH, AND SELL THEIR SERVICES.

Whether you’re selling one-on-one, leading a presentation, selling from the stage, or e-mailing a pitch, we’ll show you how to use our proven communication techniques and business processes to EXPLODE your INCOME.

AT SPEAK YOUR WAY TO CASH®, WE TEACH CONSULTANTS, SPEAKERS, TRAINERS, ATTORNEYS, ENTREPRENEURS, AND OTHER PROFESSIONALS TO

Whether you’re selling one-on-one, leading a presentation, selling from the stage, or e-mailing a pitch, we’ll show you how to use our proven communication techniques and business processes to EXPLODE your INCOME.

HERE ARE THE
SPEAK YOUR WAY TO CASH® SERVICES:
OUR PRODUCTS

We have several informational products to help you book more, charge more, and sell more.

Whether you're looking for a book to read or wish to take a deep dive into a comprehensive training

course, we've got you covered.

HERE ARE THE
SPEAK YOUR WAY TO CASH® SERVICES:

OUR PRODUCTS

We have several informational products to help you book more, charge more, and sell more. Whether you're looking for a book to read or wish to take a deep dive into a comprehensive training course, we've got you covered.

SPEAK YOUR WAY TO CASH® THE BOOK!

Ashley’s best-selling book is packed full of the

information professionals need to reach the top of

their industry.

Learn More

YOUR FIRST FIVE-FIGURE CONTRACT COURSE

The SYWTC Your First Five Figure Contract course is

designed to get you those five to six-figure contracts

from corporations and universities.

Learn More

THE PITCH YOUR WAY TO CASH MEMBERSHIP

Our Pitch Your Way To Cash Program reveals a simple

one-hour-a-day strategy to land large clients even if

you’ve never sold to large clients before….

Learn More

THE SPEAK YOUR WAY TO CASH MASTERMIND

The Speak Your Way To Cash®️ Mastermind is for

service-based business owners and experts who

already have a revenue-generating business and are ready to scale.

Learn More

SPEAK YOUR WAY TO

CASH® THE BOOK!

Ashely’s best-selling book is packed full of the information professionals need to reach the top of their industry.

Learn More

YOUR FIRST FIVE-FIGURE

CONTRACT COURSE

The SYWTC Your First Five Figure Contract course is designed to get you those five to six-figure contracts from corporations and universities.

Learn More

THE PITCH YOUR WAY TO

CASH MEMBERSHIP

Our Pitch Your Way To Cash Program reveals a simple one-hour-a-day strategy to land large clients even if you’ve never sold to large clients before….

Learn More

THE SPEAK YOUR WAY TO

CASH MASTERMIND

The Speak Your Way To Cash®️ Mastermind is for service-based business owners and experts who already have a revenue-generating business and are ready to scale.

Learn More
OUR LIVE EVENTS

Our live events have become “must-attends” for professionals who are serious about their businesses and are looking to grow exponentially. Our attendees now number in the hundreds (we sell out every time), with an astonishing number of repeat attendees who want the latest in what we offer. Why? Because what we teach not only works, but is immediately deployable.

OUR LIVE EVENTS

Our live events have become “must-attends” for professionals who are serious about their businesses and are looking to exponentially grow. Our attendees now number in the hundreds (we sell out every time), with an astonishing number of repeat attendees who want the latest in what we offer. Why? Because what we teach not only works, but is immediately deployable.


Our now-annual three-day event has become legendary.

 

It is here where people learn how to package their expertise, services, and wares into an irresistible presentation that corporations, universities, and other organizations want.

It is here where speakers, consultants, authors, attorneys, educators, and other professionals all come together and get the hands-on interaction and instruction from Ashley and other experts who have walked the talk. 

 

It is here where a recent student took what she learned, went back to her hotel room that night, put together a proposal, e-mailed it out, and LANDED A CONTRACT the next day. If that doesn’t tell you how powerful and life-changing this event can be, nothing will. This is the event people come back to again and again. Why? Because each time something magical happens. And this year will be no different

GET YOUR TICKET NOW

BLACK WOMEN SELL LIVE

As a black woman, Ashley understands the barriers society has created, intentional or not. And, along with several other professional women of color, she’s put together a program specifically for Black Women who want to KILL IT in sales and business.

 

This is real stuff from real people. Epic Sistahs who have stared down and overcome the mental roadblocks and stereotypes that have kept many professional black women from the success they DESERVE.

 

This is our most specific and intimate event. Because it’s centered on a particular demographic – one that gets ignored over and over. 

JOIN THE WAITLIST FOR 2026 NOW

BLACK WOMEN SELL LIVE

As a black woman, Ashley understands the barriers society has created, intentional or not. And, along with several other professional women of color, she’s put together a program specifically for Black Women who want to KILL IT in sales and business.

 

This is real stuff from real people. Epic Sistahs who have stared down and overcome the mental roadblocks and stereotypes that have kept many professional black women from the success they DESERVE.

 

This is our most specific and intimate event. Because it’s centered on a particular demographic – one that gets ignored over and over. 

As a black woman, Ashley understands the barriers society has created, intentional or not. And, along with several other professional women of color, she’s put together a program specifically for Black Women who want to KILL IT in sales and business.

 

This is real stuff from real people. Epic Sistahs who have stared down and overcome the mental roadblocks and stereotypes that have kept many professional black women from the success they DESERVE.

 

This is our most specific and intimate event. Because it’s centered on a particular demographic – one that gets ignored over and over. 

Learn More

Our now-annual three-day event has become legendary.

 

It is here where people learn how to package their expertise, services, and wares into an irresistible presentation that corporations, universities, and other organizations want.

 

It is here where speakers, consultants, authors, attorneys, educators, and other professionals all come together and get the hands-on interaction and instruction from Ashley and other experts who have walked the talk.

It is here where speakers, consultants, authors, attorneys, educators, and other professionals all come together and get the hands-on interaction and instruction from Ashley and other experts who have walked the talk. And it is here where a recent student took what she learned, went back to her hotel room that night, put together a proposal, e-mailed it out, and LANDED A CONTRACT the next day. If that doesn’t tell you how powerful and life-changing this

event can be,

 

nothing will. This is the event people come back to again and again. Why? Because each time something magical happens. And this year will be no different

Learn More
CONNECT WITH
SPEAK YOUR WAY TO CASH®
Join Here
Watch Now
Follow Us
Follow Me

THE SPEAK YOUR WAY

TO CASH® PODCAST

Subscribe

CONNECT WITH SPEAK YOUR WAY TO CASH®

Join Here
Watch Now
Follow Us
Follow Me

THE SPEAK YOUR WAY

TO CASH® PODCAST

Subscribe

It's about your revenue matching your expertise. But how does that happen exactly?

 

At Speak Your Way to Cash, we teach professionals to better package, pitch, and sell their products and services.

And when we say "professionals", we mean consultants, trainers, speakers, entrepreneurs, attorneys, doctors, authors… any professional who has something to sell.

 

And what do they sell? Consulting services, professional services, information, books, courses, training, speaking gigs, or any and all combinations of such.

 

We educate and train via in-person events, courses, books, podcasts, social media, and even an invitation-only private mastermind group with Ashley, the company founder.

It's about your revenue matching your expertise. But how does that happen exactly?

 

At Speak Your Way to Cash, we teach professionals to better package, pitch, and sell their products and services.



And when we say "professionals", we mean consultants, trainers, speakers, entrepreneurs, attorneys, doctors, authors… any professional who has something to sell.

 

And what do they sell? Consulting services, professional services, information, books, courses, training, speaking gigs, or any and all combinations of such.

 

We educate and train via in-person events, courses, books, podcasts, social media, and even an invitation-only private mastermind group with Ashley, the company founder.

WHAT ARE OUR CLIENTS SAYING?!

CLIENT PITCHES $56,000 CONTRACT AFTER THE PITCH YOUR WAY TO CASH CHALLENGE:

CLIENT PROJECTED $1M IN 2022 REVENUE POST SPEAK YOUR WAY TO CASH©:

CLIENT LANDS $140K+ IN CONTRACTS POST SPEAK YOUR

WAY TO CASH©:

Previous Next
WHAT ARE OUR CLIENTS SAYING?!

CLIENT PITCHES $56,000 CONTRACT AFTER THE PITCH YOUR WAY TO CASH CHALLENGE:

CLIENT PROJECTED $1M IN 2022 REVENUE POST SPEAK YOUR WAY TO CASH©:

CLIENT LANDS $140K+ IN CONTRACTS POST SPEAK YOUR

WAY TO CASH©:

Previous Next

SPEAK YOUR WAY TO CA$H

COURSE

LEARN WHO TO PITCH, HOW TO PITCH THEM AND WHERE TO FIND PAYING ENGAGEMENTS?

Interesting note on the above video: at 5:00 in, the interviewer states the reason they are even talking. And that reason is Ashley sent her an e-mail pitch. Not once, but twice. Ashley literally pitched her way into this very television interview. THIS IS PART OF WHAT WE TEACH!

Learn More

SPEAK YOUR WAY TO CA$H

COURSE

LEARN WHO TO PITCH, HOW TO PITCH

THEM AND WHERE TO FIND PAYING

ENGAGEMENTS?

Interesting note on the above video: at 5:00 in, the

interviewer states the reason they are even talking.

And that reason is Ashley sent her an e-mail pitch.

Not once, but twice. Ashley literally pitched her way

into this very television interview. THIS IS PART OF

WHAT WE TEACH!

Learn More


COMPANY HISTORY

Ashley Kirkwood founded Speak Your Way to Cash after leaving her corporate attorney position. The original intent was to help speakers level up their game and book the 5-6 figure corporate and university contracts everyone wanted.

 

It began as one in-person event. There were perhaps 20 people there. And it was wildly successful – attendees took the information Ashley presented and, to put it quite bluntly, went out and made money.

 

Through word-of-mouth alone, a second event was held a few months later. This one had triple the attendance.

But a funny thing also happened – the audience was NOT only speakers. It was consultants, coaches, trainers, authors, executives, lawyers, doctors, entrepreneurs… it was a sea of professionals looking to book more, charge more, and sell more.

 

These professionals saw speaking as a way to better sell their consulting services, sell their books, sell their training… whatever they offered. And some saw "speaking" on a smaller level than the big stage. After all, isn't leading a training workshop speaking? And trainers and consultants want those bigger corporate contracts too… exactly what Speak Your Way to Cash® was teaching.

A SHIFT IN FOCUS...

So given our expanded audience, the focus shifted slightly to become what we are today – we coach professionals and entrepreneurs on how to use communication and processes to book more, charge more,

and sell more.

 

It's about mindset. It's about speaking. It's about pitching. It's about sales. It's about licensing your information. It's knowing what to say, how to say it, when to say it, and who to say it to. It's about selling from the stage, selling one-on-one, and selling via e-mail pitch. And it's all VERY effective. How effective?

 

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, e-mailing it, and bam, offer received.

 

We change lives here at Speak Your Way to Cash®.

 

And that's what we're all about.

COMPANY HISTORY

Ashley Kirkwood founded Speak Your Way to Cash after leaving her corporate attorney position. The original intent was to help speakers level up their game and book the 5-6 figure corporate and university contracts everyone wanted.

 

It began as one in-person event. There were perhaps 20 people there. And it was wildly successful – attendees took the information Ashley presented and, to put it quite bluntly, went out and made money.

 

Through word-of-mouth alone, a second event was held a few months later. This one had triple the attendance.

But a funny thing also happened – the audience was NOT only speakers. It was consultants, coaches, trainers, authors, executives, lawyers, doctors, entrepreneurs… it was a sea of professionals looking to book more, charge more, and sell more.

 

These professionals saw speaking as a way to better sell their consulting services, sell their books, sell their training… whatever they offered. And some saw "speaking" on a smaller level than the big stage. After all, isn't leading a training workshop speaking? And trainers and consultants want those bigger corporate contracts too… exactly what Speak Your Way to Cash® was teaching.

A SHIFT IN FOCUS...

So given our expanded audience, the focus shifted slightly to become what we are today – we coach professionals and entrepreneurs on how to use communication and processes to book more, charge more,

and sell more.

 

It's about mindset. It's about speaking. It's about pitching. It's about sales. It's about licensing your information. It's knowing what to say, how to say it, when to say it, and who to say it to. It's about selling from the stage, selling one-on-one, and selling via e-mail pitch. And it's all VERY effective. How effective?

 

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, e-mailing it, and bam, offer received.

 

We change lives here at Speak Your Way to Cash®.

 

And that's what we're all about.

MEET THE FOUNDERS

Ashley Kirkwood is an entrepreneur, speaker, and award-winning lawyer. As a renowned corporate attorney, she reached what many would call a peak – a $300k+ job. But she left it to go on her own.

 

She began a virtual law firm, which quickly replaced and then surpassed her previous income. But along the way, she realized two things: she loved speaking and teaching, and she also had a real talent for scaling up a business. She perfected packaging and presenting professional services to corporations and other organizations, and started teaching others. Speak Your Way to Cash® was born.

 

Ashley’s enthusiasm and success mindset are infectious, and her results have been well-documented. Most important to her, however, is how her teachings help, inspire, and empower others. Professionally, that’s what she lives for.

 

Ashley has been recognized as a thought leader by FORBES, Crain's Chicago Business, Black Enterprise, The Chicago Tribune, and more.

Chris Kirkwood is an educator and sales professional at heart. Always walking an entrepreneurial / non-profit professional path, he’s mentored, coached, and established programs directed at helping high school and college students reach and exceed their goals.

 

Chris also developed a sales process that he called “empathetic selling”, aimed at teaching sales professionals how to sell from a more introverted perspective that looks to educate and help people. This has proven to be incredibly effective (all sales training likes to “say” they help people, but Chris truly walks the talk.)

 

With Speak Your Way to Cash® poised for expansion, Ashley convinced him to come on board as Sales Director in February of 2021.

 

Since that time, the company has experienced exponential growth. Chris’ voice has become instrumental in the company’s offerings, teachings, and overall tone, where an empathetic, helpful demeanor (plus stellar client results) are what truly drives business.

MEET THE FOUNDERS

Ashley Kirkwood is an entrepreneur, speaker, and award-winning lawyer. As a renowned corporate attorney, she reached what many would call a peak – a $300k+ job. But she left it to go on her own.

 

She began a virtual law firm, which quickly replaced and then surpassed her previous income. But along the way, she realized two things: she loved speaking and teaching, and she also had a real talent for scaling up a business. She perfected packaging and presenting professional services to corporations and other organizations, and started teaching others. Speak Your Way to Cash® was born.

 

Ashley’s enthusiasm and success mindset are infectious, and her results have been well-documented. Most important to her, however, is how her teachings help, inspire, and empower others. Professionally, that’s what she lives for.

 

Ashley has been recognized as a thought leader by FORBES, Crain's Chicago Business, Black Enterprise, The Chicago Tribune, and more.

Chris Kirkwood is an educator and sales professional at heart. Always walking an entrepreneurial / non-profit professional path, he’s mentored, coached, and established programs directed at helping high school and college students reach and exceed their goals.

 

Chris also developed a sales process that he called “empathetic selling”, aimed at teaching sales professionals how to sell from a more introverted perspective that looks to educate and help people. This has proven to be incredibly effective (all sales training likes to “say” they help people, but Chris truly walks the talk.)

 

With Speak Your Way to Cash® poised for expansion, Ashley convinced him to come on board as Sales Director in February of 2021.

 

Since that time, the company has experienced exponential growth. Chris’ voice has become instrumental in the company’s offerings, teachings, and overall tone, where an empathetic, helpful demeanor (plus stellar client results) are what truly drives business.


  • P.O. Box 823, Flossmoor, IL 60422

  • hello@ashleynicolekirkwood.com

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