Your Next Move - Prioritizing Mental Health Could Save You Money

Episode Date: April 22, 2025

In this episode, Inc. staff reporter Ali Donaldson interviews Ashley Kirkwood, founder of Speak Your Way to Cash, which is No. 370 on the 2024 Inc. 5000. The company aims to help speakers, experts, and entrepreneurs land speaking contracts.   Ashley talks about balancing her work life and her married life, her trick to staying productive, and how she's learned to incorporate self-care into her daily routine.

I'm Sarah Lynch and you are listening to Your Next Move, Audio Edition, produced by Inc. and Capital One Business. For this season, we gathered an array of conversations with entrepreneurs who made last year's Inc. 5000 list. They joined us in our Your Next Move booth at the Inc. 5000 to share lessons learned and anecdotes from building their businesses. In this episode, Inc. staff reporter Ali Donaldson interviewed Ashley Kirkwood. She is the founder of Speak Your Way to Cash. They're ranked number

370 on the 2024 Inc. 5000 list. Ashley's company aims to help speakers, experts, and entrepreneurs land speaking contracts. Ali started this conversation by asking Ashley about what's driving the company's fast growth. Ashley Hildesby I attribute a lot of our fast growth to community. So one of the things that my husband and I both have a church background, both of our dads are pastors. We did not plan that. We did.

Nicole Soule Both PKs, married another pre-church kid. Ashley Hildesby Yes, both PKs. And one thing that churches do really well, especially churches that are well run, is they get people excited about coming together. And it's not just about the pastor who's the leader. And in our company, I really wanted that same vibe. I wanted the familial vibe. I wanted people to come and work with our company and we just not be a vendor. But we become a part of doing business and life with them. So we started a Facebook group and our first Facebook group was about writing a book

in 30 days, which I never did by the way, but I wanted other people to do this with me. And that did not work. It did not work. My book took a year and it's called, Speak Your Way to Cash, but I realized that people just loved talking about their experience, talking about their journey.

And my husband came up with the name Speak Your Way to Cash because I was getting paid to speak at colleges around America while working as a federal trial lawyer for a large law firm. So I was kind of doing this on the side, and people kept asking, you know, how are you getting paid to speak? And so I did a really small event, 10 people, in a WeWork, and the venue was free because my husband worked at WeWork.

So he got us this little room and it was 10 people there. And after that event, I thought nothing of it, but our clients who came to that event were like, can you do this again? And our event, Speak Your Way to Cash, started from that 10-room person event that probably made 500 bucks and grew into a multimillion dollar company from there. And we kept doing events, they got larger and larger, and we kept helping speakers and experts land paid speaking contracts, speak persuasively, and learn how to sell

their services to their clients. Ashley, this is so fascinating because when you first started speaking, I'm guessing you were talking to law schools, kids that want to go to law school about your experience as a trial attorney. Yeah, it's funny. I actually was talking a lot about confidence. So the colleges that were hiring me to speak were hiring me to speak on confidence.

It was called the Currency of Confidence, which is our framework. Good phrase. Thank you. It's our trademarked framework for how to build your confidence. And it's comprised of mindset, your beliefs, and your actions.

So that was the framework that I was teaching colleges across America. And when people saw me doing that, they were like, well, you know, I have life experiences. I'm an expert, too. I've been able to overcome some things. How do I share my story and get paid for it? How can I have my own business instead of just doing what everyone has expected me to do? And so I loved law.

I was a trial lawyer, so I got to speak in that vein. But I went to work one day and I'm like, okay, are you really going to do this for the rest of your life? And that was the thought that I had. And so I'm like, okay, I'm a researcher. So I went and interviewed all of the top partners at the firm. I mean, these people were making tens of millions of dollars. I worked at, right now, it's the largest law firm in the world by revenue. I was the only black woman in the litigation department. And I went and talked to all these top lawyers and I was like, what do you like about this job? And it was not the money, it was the work. And it was at that moment that I realized if all I like about this job is,

or predominantly what I like about this job is the money, I'm never going to be the best in the world at it. I have to go and find an area where I can thrive in where my joy comes from the work, not the money. And I loved that 10 conference room environment where I was teaching people about their dreams and seeing them go out and get their first paid engagement and start a business. So that became my passion. But I never thought in a million years I could do it full time.

Because I'm a traditionalist. I'm like, you go to school, you get a job. Yeah, you get health care, you get paid every two weeks. There's no risks. But I was at work one day and my first law job I loved, but I went to another firm and I just really hated it. For the first time, I feel like I felt depressed. And I'm not a depressed person. I've never dealt with depression until then.

And I was going to work and I just start bawling on the train and people are looking at me like I'm crazy, because it's a public train. What city are we in? Oh, we're in Chicago. So, you know, people are looking at me like I'm crazy, because it's a public train. What city are we in? Oh, we're in Chicago. So, you know, people are not even asking if I'm okay. They're like, what is wrong with this girl? Okay, like, they're not even like...

They're not even being Midwesterners. Are you okay, baby? No, they're like, what is wrong with this lady? And I wrote out a gratitude list of all the things I had to be grateful for just so I could calm myself down and stop crying. And then I was like, okay, Ashley, you're clearly not happy, but what are you going to do about it? And a couple days later, I quit that job.

And I was making 300 grand a year, and I didn't have a big backup plan, but I had a book that I'd written about my law school journey. And I'd already gotten paid a little bit to speak, so I took that book and I cold called law schools to start getting a speaking tour together. And through that process, I didn't use connections or anything. Through that process, I learned that cold calling works, cold emailing works, outreach works. And so I developed this system for getting paid to speak.

And thank God I didn't use connections because I did it without connections. I was able to give that system to my clients and help them get paid to speak. And then we realized what we're really teaching isn't how to speak, what we're teaching is how to sell. And that is how we became Speak Your Rate of Cash, a sales training company. And now we've, you know, our first event had 10 people, the event we did a couple weeks ago, had hundreds of people and brought in $1.6 million.

So, in a weekend. So, you know, the events have grown, our clients have been successful. We've seen clients go from never getting paid to speak to building their own million dollar companies under our brand. And it's great because they're like me, they're experts, doctors, lawyers, engineers, or they have expertise not by way of degree but by way of experience. And so showing them that that's valuable outside of a corporate structure is something that

their families and them find lots of value in and we get a lot of joy in helping them do that. I'm curious, Ashley, when you realized that there was this niche that was underserved of trying to help create more speakers and was there anyone else in this space of sort of consulting in that? Because you know recently I was just speaking with someone at my college who's trying to help like professors do that and they look at some of the professors that like have their name out there and speak to me a lot that do their own speaking engagements and they're

like well how do I do that? I have advice, I'm an expert. I have great research I can share. So was there anyone else doing what you're doing? Not in the way that we do it. Because one of the things that makes our community unique is that 90% of our clients are actually black women experts. And so what we do is really unique. We actually, I studied black women millionaires from the 1800s and the 1900s. And I pulled out some of the sales strategies that they were able to use.

And I teach my clients those same sales strategies. At our event a couple of weeks ago, we pulled an ad that Madam C.J. Walker wrote and put it up there. And literally the headline of the ad was, is your hair short? And we use that. And I told my clients, I'm like,

does that not catch your attention? And they're like, yeah. And I'm like, okay, so how can you write like that? And so we really have been able to infuse culture, history, faith, and community. And we make it so much fun to learn sales. And there's not many people that serve our specific niche the way that we do. And then we bring the family into it. 60% of our clients are married.

Me and my husband, we run the business together. And so we don't just train our clients. We tell them, bring your spouse, bring who you're married to. Let's train the family so that you have the support that you need, whether they're going to work in your business or not. And that goes back to, I think, the church background of just knowing, like, it's not just about, you know, mom or dad or whomever. It's about the family unit thriving,

and everyone needs to be on the same page for that to happen. And what's your advice for other founders that work with their spouses or even other loved ones in their family of like how to manage that because like there are going to be disagreements in the business but you want to all still love each other when you go home. TAYLOR You know it's so funny I was just featured in Essence magazine for quote unquote retiring my husband which literally just means he's retired from education but he works in the family business so he's not retired at all. So the running joke, if I ask him to do anything, is like, I'm retired, okay, so I don't know,

I'm not going to do that. But in that article is the same advice that I would give here, which is you need rules. One of ours was if it ever came down to, am I going to run this business or are we going to stay married? He would be the one who steps away from the business, I would run the business, he would get a job or start his own company, and then we would stay married. And so there's always that guiding light.

Another rule was, we both had to be in therapy. So before he joined the company, that was one of our non-negotiables, was like, hey, we wanna both be in therapy to understand, what are the things that make me angry? what are the things that make me angry? What are the things that make me happy? What is my communication style? What is my avoidance style?

And we really needed to discover that. Because when you work together, like, who I am at work is who I am at home, but I don't necessarily turn it off. My husband has to turn it off. But I didn't understand that until going through therapy. So I would say making sure you get therapy and then three have clearly defined roles

that don't overlap. So for us, it was a hot mess. Okay, I'm just gonna say it the way it is. It was a hot mess in the beginning because we both were trying to do everything together. I love my husband so much. I'm like, yeah, we can work on this marketing campaign together, we can work on these.

He's just like, I need some separation. So we figured out through trial and error, what are our strengths? I am really strong on stage speaking to thousands of people and showing them who they are and then inviting them to become clients. I am very good at selling one to many. He's very good at selling one to one.

I'm more extroverted, he's more introverted. Now, we have three things. It's like if you do these three things this year You have done an amazing job for the company and I cannot complain about anything else and he's like if you do these three things For the year you have done an amazing job for the company and I'm not gonna complain about anything else And then we both know that we're pulling our weight because we have clearly defined KPIs and I do not manage him. We work together He's like I you're not my boss.

I'm like, I'm not your boss, babe. Like, it's okay. So that's kind of how we've done it. And then just remember to have fun. I wish I would have learned about balance earlier. Now we do an annual sabbatical. We did six weeks last year. We're doing four weeks this year. We went to Ghana, Thailand, Bali, and just six weeks did not work. Our daughter came. She's four.

It was amazing. And it was what I needed for my mental health. And now I play tennis, I have a hobby. I never had a hobby before in my life, but I had to get a hobby. And I play tennis and now I'm on these competitive tennis teams. And it's just, it's so fun, but I needed to find out who am I outside of work?

You know, my identity was always tied to being a lawyer. Quickly, my identity became tied to being an entrepreneur. Then it became tied to being a seven-finger entrepreneur. Then it became tied to being a seven-finger entrepreneur. Then it became tied to being a multi-seven-finger. So it was just always an identity outside of myself. And I had to realize that that just wasn't healthy for me or my family. And I had to take some accountability there. Like, I allowed this to get out of control.

And it was because I had absolutely no balance. And now I think I have a really good rhythm of things that are just for me and not for us, but for me that helped me to feel fulfilled. And he has things that are for him. And that makes us a happy, harmonious couple. When we come back, Ali asked Ashley how she gets it all done.

But first, a quick break. I really like that you have, Ashley, those things you do outside of work that help you unplug. What do you do during the workday to help you stay productive? Oh, that's such a good question. One thing that I do is I set timers. So I can get really bored with work sometimes. Like, okay, do not judge me, guys. But I can get really bored with the mundane work.

Like, one of the things that I do for our company is I write hundreds of emails for our company. And I really understand our brand voice, and so I've kind of made that and running our advertising. I actually run the Facebook ads. So I've spent over 700 grand on Facebook ads myself. Like, I'm the one running them. And they're profitable. So that involves a lot of writing.

And so sometimes I'll get a little bit bored, so I'll give myself prizes. So I'll say, OK, I'm going to write for 60 minutes straight, no breaks. I have an app called Opal, O-P-A-L. It blocks social media, and it has a setting that's called Deep Focus, where you cannot unblock it. If you put that on, you're done.

Not on that phone. So I use that app, and I'll give myself 60 second time blocks and I will just force myself to work for those 60 second blocks and I'll just like, I'm going to do three. I'm going to do three in a row. I'm going to take a 10 minute break in between and do whatever I want. But that's how I stay productive at work. Ooh, I really like that. And do you have any other things?

Like do you feel like you're a list maker or you're a calendar person? I am a list maker. I'm an Asana girl. So I will use a digital list and I will put categories of what I need to do for that day and then I'll just check them off, which is so satisfying. But another thing that I've started doing recently is I'll make a list in a Google Doc and I'll go through and go through that list and try my best to assign every single task to someone else.

And after I feel like, okay, I can't assign this to anyone else, only then will I go back and make my list. So I won't make my list on everything that needs to be done. I make an enlistment in Google Docs and then I assign it to everyone else with directions or a Loom video. And then I put in Asana, only the tasks that I need to do as the CEO. And I really force myself to be strict about it, because sometimes, you know, I'll just do it myself.

No, you have to assign 85% of everything on that Google Doc to someone else on your company before you make your final list. So I'm curious who you talked about Facebook ads and has that been the most affecting marketing hack because I think it must be hard for you to reach your clientele because by definition a lot of them are not yet speakers but want to be so how do you find those people? Yes so Facebook ads have been amazing for that. Facebook ads and content. So we do a lot of content marketing, a lot of Facebook ads, a lot of speaking in other

people's audiences. And I know that my clients are feeling something. So if you go back to that currency of confidence framework, it's also a content writing framework. So I think of it like mindset. What are the thoughts my clients are having right now that they can't voice because they're at work? And I will make a post about those thoughts and then I'll tell them, hey, DM me if this really resonated with you. And then that is how we'll get leads and we'll use Manny chat or some automation to really send them into a funnel where they get our book. 80% of our clients who've invested over $30,000 with us have read the Speak Your Rate of Cash book first.

So my book is a great introduction. It's a great foundation for how I work, and it's in my voice. So they kind of know, like, do they like my style or not? Like, they'll be able to tell from that. So between content and ads, that's kind of how we've been able to reach them. And that's been working really well. Ashley, how many employees do you all have now? So we have 17 globally, but many of them are contractors. Three full-time employees, and then our team, our payroll, is 17 people that we pay month to month. And what's your advice for finding the right people?

Oh, you know, one of the things that I used to run away from that's been working for most really now is hiring from our community. So we have a free Facebook group. We have people who are always willing to volunteer from our events. And I was always very self-conscious about hiring from my community because I was worried that if they like me as their community leader, I'm serving them. But if they come and work for the company, they're serving the company. So I didn't want them to, like, lose that image they had of me

as, like, just their best friend in their head. And I really had to get over it. Because hiring from our community has been the best thing for us because they already understand the brand, they already understand the culture, and they want to work. So when we have events and we have volunteers that sign up, we look at who does the best job

and we have started having people apply to be like volunteer leads. And if they apply to be a volunteer lead and they do a great job in that capacity, we'll invite them to an interview. So we will look to see within our community who's looking for this role. So that's one. The second thing is never have them work for you full-time until they work for you in some capacity. So we have seven day trials and 30 day trials that we do for each role and of course they're paid and during that trial I don't train. I give them tasks and I analyze how they complete those tasks. And so if they get it wrong, it's okay.

It's really to see how do you think? How fast can you make decisions? How fast can you take action? And typically we will give them some background knowledge but they don't need like a full 30 day onboarding for a 30 day trial. So we always have people go through the trial and everyone who's completed that trial successfully,

for the most part, like I think 90% have been with our company for at least two years at this point. So that is a great indicator of whether or not we will have a good working relationship. And we do a written interview before an in-person interview. So they apply, they're invited to a written interview and that written interview lets us know how they think,

it lets us know what they're thinking about. We ask them to complete tasks and if they're in a videography position, we'll pay them for the task. So depending on the complexity of it or how long it takes, we may even pay them to do that written interview. But that really has given us a lot of insight into who they are.

And one of the parts of the written interview is answer these questions on Loom and submit it here. So I'll actually hear some of their answers and I can speed that up and go through 20 of those in two hours versus sitting all day through interviews when the person may not qualify on writing. So I am really big on, maybe it's the law background, but I'm like, you gotta know how to write. You gotta know how to critically think. So if you can write and critically think, I can train you on some other hard skills.

So Ashley, are you like walking around on 1.5 speed listening to everyone? Yes. Like a little podcast in your head? Yes. And sometimes, depending on the role, another leader in our company may take the first pass and then I'll review whoever they recommend because they know me really well. I really like that with the experiential interview too because it's also seeing how they work with the team. Yes, definitely. You learn a lot. It's hard because in interviews, there are some people who are just experts at interviewing. So you really want to know not can you do well in an interview,

can you do well in our office, in our culture. And when you look back over the past three years, have there been like the biggest mistake you've made that you would do differently? The biggest mistake I've made in the past three years is not taking care of my mental health. It has cost us money, right? Because I'm a public-facing figure and there was a time where I had like a total mental breakdown and it was like on a stage in front of clients and I was just like so exhausted and tired. And I was really flippant and really disrespectful

in like the way I delivered a particular part of my speech. And it was totally just because I did not prioritize myself, my personal wellness over my company's revenue bottom line. And I should have because by prioritizing my personal wellness, I'm prioritizing the company since I'm the person that brings in the most money for the company. But I didn't see it like that. And so now a lot of the safeguards that we have in place are so that I can thrive

professionally. And my pastor, Pastor Darius Daniels, he's actually a pastor and a leadership expert. But one of the things he said to me was, hey, you know, when God created Heaven and Earth, that seventh day, it wasn't like he needed to rest. It was that he rested because he was productive. And I was waiting until I was exhausted to rest. Instead of, because I'm so productive,

I have to rest on a consistent basis. So that's been the biggest mistake that's affected us, you know, professionally and financially. And thank goodness, because we have such a transparent community, I was able to just tell the truth on my YouTube channel. I did a full hour-long video, like, this is what happened, this is how I've overcome it, this is what I was dealing with. And something incredible happened, where my DMs were flooded

with people that were like, thank you for not lying to us, thank you for not covering up what you were going through, thank you for sharing your story, I'm gonna do better, I'm gonna eat better, I wanna get a a personal trainer and so our whole community has now been Focusing not just on revenue, but also on rest. I like that cuz I you know, I ran track growing up So it's like the thing from your coach It's like those rest days are just as much important as those days when you're doing the workout Yes, exactly

And I didn't know that you know and in law when you're on trial you work 20-hour days for as long as the trial takes You don't think about oh, I need to have self care. I don't even think the partners would have let me just, oh, I need a self care. I don't think that would have worked out. Not a book out. Well, Ashley, thank you. This has been great.

Thank you. It's been amazing. I'm so glad you all had me on. That's all for this episode of Your Next Move. Our producers are Blake Odom and Avery Miles. Editing and sound design by Nick Torres. Executive producer is Josh Christensen. If you haven't already, subscribe to Your Next Move

on Apple podcasts, Spotify, or wherever you listen. Your Next Move is a production of Inc. and Capital One Business.