We’re excited to welcome Ashley Kirkwood to this week’s episode of the Wealthy Woman Lawyer® Podcast. After graduating with honors from the Northwestern University Pritzker School of Law, Ashley began her career at one of the largest and most profitable law firms in the world, Kirkland & Ellis.

Ashley was living the dream as a well paid corporate lawyer but when she changed firms based on an offer she couldn’t refuse, the dream soured quickly. She knew there had to be a better way than stuck in a firm that didn’t fit. In our interview, we discuss the big shifts she made, and secrets to her success. Plus, 

  • How to play to your strengths to increase your impact
  • How to get paid top dollar as a speaker
  • The secret to scaling your own law firm so you are no longer needed for the day-to-day operations
  • Her important message to other women law firm owners
  • And more.

Listen now…

Mentioned in this episode:

  • Ashley Nicole Kirkwood’s Website
  • Text: 312-847-4590 
  • Speak Your Way To Cash Live Event


Davina Frederick: Hello and welcome to the Wealthy Woman Lawyer podcast. We believe all women lawyers deserve to be wealthy women lawyers. Our mission is to provide thought provoking powerful and practical information to help you in creating your own sustainable wealth generating law firm without overwork or overwhelm so you can live your best life. I’m your host, Davina Frederick, and I’m so excited for you to meet our guest today. So let’s get started. After graduating from Northwestern University Pritzker School of Law with honors, attorney Ashley Kirkwood, started her career at one of the largest law firms in the world Kirkland and Ellis LLP. While there she tried cases on behalf of large insurance companies. She also landed in the pages of American lawyer after a hard won victory in federal civil rights jury trial. 

After that trial, Ashley left Kirkland to work with another large law firm, where she represented employers in employment discrimination and sexual harassment cases. That experience led Ashley to hang out her own shingle, creating Mobile General Counsel. So she could help emerging companies bulletproof their businesses with trademarks, contracts, and business counseling. Ashley frequently provides legal training such as clap back with contracts and get the T on trademarks. When she’s not teaching and serving our clients, you might catch her serving as an on air legal correspondent for a local Chicago television network, speaking at a college or corporation, or helping her husband run their nonprofit organization to serve children in Chicago, by educating them about high paying careers. 

So Ashley is doing all the things and there’s some stuff other things she’s doing in here that I’ve left out this intro that we’re gonna get into in our conversation. And I’m super, super happy and excited to have you here today, Ashley, so we can get the scoop, and find out how it is that you’re able to do all of this. It makes such a great impact in the world. So welcome to the Wealthy Woman Lawyer podcast.

Ashley Kirkwood: Thank you. Thank you so much for having me. Really excited to be here.

Davina: Yeah, good. So why don’t you start out by telling us about your journey. I know I kind of covered a little bit in the intro. But tell us about, were you somebody who always wanted to new you always wanted to be a lawyer? Or was there somebody in your life who inspired you? Or were you one of those people that was like, you know, I went to college. And now I don’t know what to do. So I’m going to go to law school.

Ashley: Yeah, so I’ve always wanted to be a lawyer since I was a young girl, young girl. I always did speech and debate. So I’ve also always wanted to be a speaker. I didn’t know that you could make a living totally doing speeches for corporations. And now I do. I always wanted to be a lawyer. It was one of my dreams and Northwestern was my dream school. So I went to the University of Illinois at Urbana Champaign for undergrad, I wanted to go to Northwestern for undergrad didn’t get in, applied to Northwestern for law school. The first time didn’t get in for anyone who is listening to this who had a harder time getting into law school. That was my story. 

So I barely graduated undergrad, had a low GPA, went to a law school in Chicago, a local law school in Chicago first and then transferred into Northwestern. And I wrote a book about that called the Law School Hustle. So I have always been one to like document my journey. I really, really, really loved the law. I loved law school. So I’m one of those people. I’m absolutely loved law school and had a goal of working at a large law firm upon graduation. And that’s kind of what I did. So it was an untraditional path that I think turned a little bit more traditional while in law school.

Davina: Yeah, I love that story. I love it. I love the tenacity of that story. Because I think for success in business and life, tenacity is going to serve you well, that, that having that vision and just not letting those obstacles keep you from living the dream that you have for yourself. So that is what is so inspiring about your story. I appreciate you sharing that. I was one of those people who did not love law school. So hey, you know, I admire you for that. But I did not love it. So tell us that you graduated from law school and you got that dream job, which is working for that big law firm. What was that like?

Ashley: It was awesome. I so I I think I’m a weird lawyer because I’m very positive about my experiences. I think a lot. A lot of my colleagues are like, Oh my gosh, big law is awful. It’s so hard. You’re going to work all those hours. And I’m like, yeah, but they pay you a ton of money out of law school. So for me, I enjoyed my first law firm I really enjoyed I loved it. It was the firm that I wanted to be at. They were there were so many exceptional and extraordinary trial lawyers there. That literally when I would get like when I would lack motivation at work, I would look up some of the most experienced trial lawyers and just go in their offices. 

Like people who’ve been practicing 40, 50 years who’ve won humongous jury trials, they were partners are making upwards of 20 plus million dollars a year because of the great work they have done for their clients. And so I’m like, ikay, I’m gonna just learn from as many people as possible. And for me that made the experience worth it. Like I was a hungry associate, I would go in offices ask for more work. Ask to go to on trial, I tried my first case relatively early for federal civil jury trials. And we did a pro bono trial. And I, I started working on that case, as a law student. So I negotiated to start working for the firm at my associate salary as a third year law student. 

So my third year of law school, I was taking wonderful classes with like Supreme Court, former Supreme Court Justice, or former Supreme court clerks, and federal judges, I love my third year curriculum, and then I was able to work so I was doing real work as a third year law student, I kind of carried that into my career. But I, I really enjoyed it. I thought it was, I thought it was awesome. It was it was kind of what I expected. Except it was way less trial work than I expected, I really wanted to go to court everyday, but outside of being a prosecutor, or defense attorney for the state that just was not or the federal government that just wasn’t, that’s just not how it worked.

Davina: We grow up watching all these shows on TV with lawyers, and we hit this vision in our head of what a lawyer does, how they always go into a courtroom with just you know, a pen and maybe a yellow pad. And there’s no other files, or boxes, or no harried looking, paralegals, shoveling things behind them, or whatever. So it’s a different experience when you’re in court, for sure. But so you know, seeing all of that and being in that world and be a part of this, that’s really loving it. And aspiring, I’m assuming kind of aspiring to be one of these attorneys who’s making that $20 million a year. And also you accomplish great things for their clients. What made you decide to change and pursue the path that you’re on now? 

Ashley: Yeah, that’s a really good point. So I met this firm that I liked, worked really, really hard to get there. I didn’t even get the job. I applied to be a summer associate at Kirkland. And they said, no. And I had this whole strategy for how I was like, I’m going to get this job. And they ended up saying, no. I took a job with one of their biggest competitors, and told them about it. And then they were like, oh, we would really love to have you. And I’m like, this plays right into my hands. And they gave me an offer so I got there. So I work hard to get there. Loved it. But there was another firm who had been recruiting me for three years, like just ever since law school every year, they’re like, do you want to come here, if you come here, we’ll do all this stuff for you. 

We’ll do whatever you want. And I was just like, you know, I’m not coming there. Unless you have at least I think I get told them like $285,000 it was something really high. I was like, man, they’re not going to give me that I’m only uh, I think I was maybe a third year at the time. I was like, and I want to be bumped up a year, I want to make partnership earlier. And I want to be able to bring in my own book of business. Because I, I’ve always been a salesperson, like for me. I did sales before law school and several sales jobs. So I’m like, look, I’m gonna, I’m gonna bring in business, whatever. They, they were like, no, that’s too much. And I’m like, okay, fine. 

That’s, that’s fine, because I love my job. And they were like, well, they came back and they were like, okay, we can do it. And we’ll do all these other things, too. And so I was like, whoa, okay, I have to leave, I think so I have to try this out. And so I left after negotiating close to a six figure raise to go to another firm. And when I got there, it was like, all the things they said they would do all the magical things that would happen. We’re just not it. And and I had mentors who actually told me, they were like, do not leave. This is the best firm for you in the city. And the resources we have are unmatched. So I’m like, oh, they’re just trying to keep me they’re not going to match this salary, all this stuff. 

And I, you know, looking back, it’s all divine, because when I got to the new firm, and had no first firm paralegals, my paralegal had a paralegal. You know what I mean? It was like, right, right. Yeah, it was a cyst. Like everywhere. She was like paralegal five, but there were four other paralegals under her and my assistant had an assistant, it was just like, the support, all I had to do was show up and think and do law. So I loved that. So I go to this other firm, and I’m like, okay, great. Where’s my paralegal? Where’s my team? What do I do? And they’re like, you’re an associate, you don’t have any of that here. And I’m like, oh, no, this ain’t gone work. And I told my husband, he was like, oh, no, you’re too used to having your stuff your way. 

And I had a thought when I was in my office one day, I’m like, man, I could do this by myself, if I’m not gonna have support, if I’m not gonna have all those things, the money if they’re paying me $300,000 plus bonus or whatever. That means I could make so much more on my own because I also saw the bills saw how they were getting clients. I was handling the cases almost atomically on my own. And I’m like, oh, well, I could do this on my own, like, I’m not gonna deal with this. And on top of that, you know, I, I’ve always been the only black woman in my department. So on top of everything else, I’m the only black woman, I’m dealing with all that stuff. And there was a situation that happened where I asked one of the paralegals that we did have we all shared her her services. 

So I asked one of her like the paralegals to come in my office, and my superior came in my office and was like, you know, don’t ask her to come in your office, because you make so much more than her. And you know, she has a law degree too. And she feels slighted that you think you’re better than her because she feels bad about you making it was just all this stuff that had nothing to do with my job. And of course, the paralegal was a white woman. And I’m like, look, I’m not going to, I’m not going to play these games, I have a job to do, I have hours to bill. And if I can’t be respected and treated like every other lawyer here, I’m not going to play like I will leave and do better on my own. And so it was kind of sporadic. 

I was like, alright, I don’t need to do this. I can handle this on my own. And at the time, I had just finished my first book, which was The Law School Hustle. So I’m like, okay, I have this book out, I could literally bulk sell this book and do a speaking tour to law schools around the country and get paid to speak and bulk sell the book. And I ran the numbers. And I was like, that’s exactly what I’m going to do. And in the meantime, I’ll start building my brand as an attorney for smaller businesses that I can start getting some working on my own. And I, you know, I left now, at the time that I left, I had the book, I had already started doing a YouTube show called Passion, Purpose and Paychecks where I interviewed entrepreneurs about their journey. 

So I had some semblance of what it was like to run a business, but I was just information gathering. I paid for the YouTube show out of pocket. We rented we had a producers, we had camera and lights and makeup for all the guests. Like it was a whole production, but I was just paying for it out of pocket, you know, just to invest in to learn. And I knew that to interview really great people, I had to have the production quality that they were used to. So I’m like, okay, well, I know something about entrepreneurship, from this YouTube show, I got this book, I don’t like being disrespected. And I was so sad going to work, like I would literally cry on the train. I’m like, I don’t want to be in this environment, it was very isolating the people weren’t, it was just not a cultural fit. I didn’t drink or do any of that. 

So I couldn’t like I’m not going out with them. And at my first firm, the reason a lot of people didn’t like it is because they said it was a it’s not a touchy feely place, they’re like, it’s not really touchy feely, and people don’t really hang out and drink. But that’s why I loved it, you know, because if you’re not like everyone else at work, then going to work at a place where they respect you for what you do is what you want. Like, for me, it was like, I could go to work there. And I always felt like as long as I crushed it, and I work hard. I had a fair shot. Whereas at the second firm, that was not what I felt. 

And so whether it was true or not in reality, I didn’t feel it. So I couldn’t operate in that truth. And so for me, it was a it was an easy decision to leave all that money on the table, knowing that it really for me, it was like, this feels so uncomfortable that there is no way that I can’t work for myself make more money, and have a better lifestyle. And that has proven to be true.

Davina: Wow, wow, what a powerful story. And I think so many people are going to really appreciate it, you share that? Because, first of all, it’s it’s awful that that happened in the situation that you were in and that you were treated in such a manner right. And after they had done so much to recruit, you know, and of course, I’m sure it makes you question why they recruited me to begin with, you know, what was the, what was the plan for me? Why was it? Why was I recruited? And you know, was it for? How I look? You know? So kudos to you for making that choice. And I think you’re going to be an inspiration to so many because I think so many of us get caught in being comfortable someplace in a in terms of making money that we sort of put up with things that are uncomfortable for us. And that can happen they happen was can happen with a lot of women. 

Certainly, I mean, I’ve been in the workplace. I’m a little bit older than you are. So I was building my career in the 80s in the 90s. And where there was a lot of, you know, there was me too happening before there was me too movement. A lot of sexual harassment and, and working in an environment where there was a lot of sexism. And you put up with you put up and shut up, which I’m so happy to see so many women not doing that now in their work environments. So I’m so appreciative that you share that story. Tell me what it was like for you. When you left and you started your own business. I want to talk about, you’ve done your due, you’re doing a couple things that I really want to dig into. 

One is you started a unique model for your law firm business. And I want to know if you started that right out of the gate. If that was a vision that you had, or if you kind of started in a more traditional route, and then it evolved. And then the other thing is you is your power as a speaker, because I really want to talk about that. so that other people can consider what their unique strengths are, then they may be able to leverage and how you’ve leveraged that. So let’s start a little bit talking about the law firm and then get into your speaking.

Ashley: Yeah, absolutely. And, you know, one thing I want to point out, I really, I think that the second firm had good intentions and recruiting me, I think that they because at the time, I had won all these awards and been in the paper in Chicago, and all of that. And so I think for them, it was like, Okay, this girl brings a lot to the table, we can bring her here. But I think that sometimes when people recruit people who bring a bit of diversity in the way that they act, and the way that they think and the way that they operate, it looks appealing, but it does require a cultural shift that people aren’t always willing to make. 

So, you know, I’m having good intentions, you know, but in the end, in the end it just if they were not willing to change the culture of who, how they operate it to accommodate differences, because I’ve actually learned after getting there, I was the third woman of color who left in under a year’s time, and I asked him about it, and they were just highly offended by that. So I will put that out there for anyone in the recruiting space, like just make sure when you want someone who’s different. It’s not just does it look cool? Or do they bring something unique to the table? Or can they do the job? It’s like, are you willing to challenge your normalcy or what you consider to be normal to accommodate people’s unique perspectives? Because that’s, that’s really what’s required.

Davina: Or to even look at the even even ask the question to begin with, is there something? Hmm, maybe it is me, you know. Right, exactly. Just to say, well, maybe there’s something here, I don’t know that I need to learn. Because if this is the third woman of color that we’ve hired, and she’s leaving, too, what are we doing wrong? And maybe we need to start asking, asking those questions, you know, yeah, that even that. Alright, so we’ll leave them in the dust as you have done and move on to another to another topic. So tell me about your law firm business? Was that something you started right away? Or did you kind of go on this book tour and do all that first? What did you do next?

Ashley: Yeah, so I started it, I’m like, in almost right away. So I went and filed the paperwork right away, started to figure out a content strategy right away about how I was going to start talking about what we will do as a firm. Um, but I initially day one, it was like, okay, let me hit the ground running with this book tour. So we hired an intern, and I hired a VA, like almost right away, to help me get organized, because for me, I’m not I can do administrative work. But I’m really good when I can just sit back and think of ways to promote and sell my products and services. So that’s what I like. I don’t love doing like the nuanced answering all the emails, it’s very overwhelming for me to log into email, and then like, 50 people want something. So I hired that stuff out right away. I started the book tour. 

And the way that I did that I literally just started calling, I got a list of all the law schools in the country. And I went, you know, narrow to wide. So I called all the law schools in Illinois found out if I could sell books there, and do a book tour there. And then I went to law schools and other countries. And then eventually, I started speaking at colleges and doing orientations and doing workshops, off schedule for different universities. And that’s when the money started to get bigger from that. And eventually, I decided to go back to corporate not as an employee, but as a vendor and sell larger five and six figure corporate speaking packages and licensing packages to organizations to help them with some of those DEI issues that I personally experienced and developed a system for helping companies with.

Davina: Okay, great, great. So I want to know more about that. But let me ask you this. Do you struggle with any sort of internal dialogue around not being a lawyer like you’re still a lawyer, but not practicing in the way that is traditional for attorneys to practice? I’m in a firm, this is what I do as a shift to speaker, did you go home supposed to be a lawyer? Was there any, any answer because I know for me, I experienced that. When I first started doing coaching, I still had my law firm business. 

But I really wanted to dive more into coaching. And I knew that I couldn’t serve two masters. And I couldn’t do both at the same to the degree that I wanted to do it. And so I had to make that decision. I’m still a licensed active lawyer in the bar. But right now, I’m not servicing clients because I felt like I couldn’t do that at a level that I would need to do it for my practice area and do this as well, I grew it to the success that I wanted to. So, but I struggled emotionally with that. Did you have that moment where you kind of were like, talking to the hubs and going? What did I do?

Ashley: Yeah, so I think for me, it’s a little bit different in that one, I struggled, I had an identity. I don’t know if it’s an identity crisis, but I had an identity struggle when I left big law, because as you know, when you go to lawyer networking events, like you go to the event, they’re like, what are you doing? You’re like, oh, I work at Kirkland. Like it was a it was an identity for me as a thing, right? Yeah, I achieved this. It means I am at this level in the market. And we tried big cases. Read the paper today? Probably my case. Like, I had a real I’m gonna deal with that. Like, it was like, oh, yeah, you see that movie, our firm was in that movie, like, that was a really big, like value identifier for me. So I struggled with like leaving that. And the second time I went to did not have the same brand at all, but it was still it was still like a larger law firm, you know. 

So I think that that was the biggest identity shift was like not not having a brand behind me that everyone knew, and that I could walk into a room and get things done. Like in Chicago, when they would say like, they were sold out of restaurants, or whatever, I’d be like, look I work at, and we need this too. And they would give us the table, okay, it’s like I really leaned into that. So that’s the hardest part. And then, when I left big law and started my own practice, I started as a law and consulting firm. So it was really like, I’m going to do a flat fee law firm. I’m going to do trademark law so I can represent clients across the country in a federal practice. And we’re going to, we’re not going to bill, we’re just going to do flat fee legal work. And I set it up like that. 

So that right out the gate, I could take flat fee legal clients, I could hire contracted attorneys, I had contracts with our firm for a flat fee as well. And I could manage my profit margins. And so I’ve always focused more on the sales and business development piece of it, and then developing the legal strategy, but having other lawyers do the work. And and that looks like making sure your legal strategy is tight and your SOPs are tight, so that you can direct the work. But that’s always been where I’ve thrived, even for my clients. So like they, they don’t need me to file a trademark, they need me to help them think through how their trademark will convert into seven different streams of revenue. And that’s my unique identifier in the legal market. Most lawyers do legal work. They don’t, they don’t strategize on the business side in the same way as me. 

So that’s kind of how I’ve been able to like distinguish it. And then our firm would do like compliance work. So sexual harassment, training, ethics, training, that type of stuff. But I ended up liking the trading side a lot more. And then people started asking me like, man, how do you land? How do you make blue cross cutting my first corporate client? For my firm was Blue Cross, which was one of the first clients that I went to try the case for, while I was at the firm. So people started asking more and more like, how do we do that we want to make more money in our business. And I realized that this is this is unique like I can, I can own a firm, and I can coach people on how to how to land these larger speaking contracts, then they can take that stuff that IP that we developed to the firm and let the firm you know, protect the IP. 

But I did have to start seeing myself less as like a lawyer in the day to day and more as a law firm owner. So now we have full time attorneys. A full time associate, we have contracted attorneys and a full time operations director who can make sure that clients are very well served. So I’m still involved in the strategy side of it. But I am more out front and more focused on, you know, doing, I want to have a company called speaker with cash. And that’s where I really am able to show up and speak and be my fullest self. And law has always kind of been for me, something that I’ve used to provide for my family and to live a life that we’ve always liked to live. But at the point that the speaking side of things ramped up, you know, it was just, it makes more sense for me to focus more of my energy there. But to your point, it is true that somebody has to lead. 

So I had to have a real sit down with my firm team, like, look, I’m going to be the strategic leader. I’m still going to help with some business development. But by the end of this year, you all need to develop business in a way that does not require my image, so that people can believe in the underlying service that isn’t even provided by me. And that the firm can sustain without means that eventually you know, we could sell the firm or do whatever we want to do with the firm so I can focus on one thing. Because I don’t I don’t think you can do two, you can’t do two things at 100%. It’s just not possible even though I would love to think I can. It’s not possible. So it was it was tough. It was really tough. Like being like, y’all are gonna have to do this and make it work.

Davina: Sort of letting that, I think, a lot of women law firm owners struggle with letting go and you were able to build a team. So that is a wonderful story. One of the things that I want to ask you about before we move on and talk about your speaking company, because I really want to dig into that is, you said, SOPs. I’m guessing, though you’re not as sit down and type up SOPs kinda a girl. Like you, you had you develop those probably by leveraging the skill sets of other people to help you am I right.

Ashley: Oh, yeah. 100%, 100%.

Davina: Can you talk about that a little bit, because I think I think a lot of us tend to think that we’ve got to do it. Like, at some point, she was sitting there in the middle of the night, typing up these standard operating procedures for everything and setting up all of our systems, before she could hire the team to go in and run the thing. And I would love for you to dispel that myth.

Ashley: Yeah, so you’re 100% right in the prop. The one negative thing about SOPs is that you have to keep updating them as your systems change. And as your processes change, because even like the bio that you read, before, before this, it came from an SOP, like I had an admin sent that to your people, but she didn’t send the most up to date one, and I’m reading and listening, like, oh, we didn’t update the SOP. So it’s something that you have to continuously update. But I did two things. So the first thing I did is I’m not gonna sit down, write it out type of person. I will speak though, and I will do webinars, and I’m fine doing that. 

So I created an internal, almost like a course for internal employees. So it’s about 15 videos, where it was me on a like, one Saturday, and I just did 15 minute videos, walking them through how I like things done. And then I had someone from Upwork, who was a, they were process consultant, take those videos and convert them into SOPs. And for about three months, I met with a process consultant every week, we came up with a list of 50 SOPs that I wanted to have written and me and this person, like developed those out over time. And so that that’s one strategy, it was not a crazy, it was a it was an investment. But it wasn’t, it wasn’t like $1500 per SOP, or anything like that it was it was an hourly rate, and whatever it costs her to write them up, she would she would write them up and bill me by the hour for them. 

So that was one thing that did help, because I’m not going to and I and I told her how I wanted it. I wanted them to be able to read it and do exactly what it says like, I don’t want them to have to look anywhere else. If it needs hyperlinks, I want it all in there. And so it’s beautiful. Way better than I would have done. And I’ve tried to have team members along the way create SOPs. And they do. But they’re they’re not as detailed as when we hired someone who actually documents processes for a living. So that is, that’s really helpful. But you do still have to update them. And in addition to that, we do have our internal training system, where when someone joins, everyone goes through the same administrative training, even if they’re not an administrator, because they need to understand the technology that we use. 

And it’s a course. It’s literally a course. It’s not publicly available to buy, but it’s just for people who’ve joined the company. So it’s something that they can start doing ASAP because they, you know, someone joins your company, they’re excited they want to get going, they can watch the course. And then we have a quiz after each little section to make sure they understand the technology and get a chance to try it out. So they’re not just watching videos. And then I review their quiz results with them and go over what they’ve reviewed the week before. So we’ve we’ve Jerry rigged a training system together at this point. That’s been working out, but it was for sure process and a lot of people were involved.

Davina: Yeah, yeah, yeah. I appreciate you sharing that. Because I do think a lot of that’s what we’re we’re trans, we’re trying to transition from being the lawyer to being the business owner, we underestimate the work that we need to put into to becoming a leader, like, it’s not something that you’re just born, you know, coming out of the womb, like a natural leader, everyone works through a process of learning how to do that, and how to how to put together a team and how to lead a team. But what we cannot do is get caught up in the details of all the doing. You don’t have to get caught up in all the details. Because you get caught up in all the details, then you don’t have time to learn how to be a better leader. Right, you know, so that’s what I love about you sharing that I really appreciate it. 

So let’s talk about your speaking because speaking, I know every woman law firm owner who’s listening to this is going well. How do you get paid as a speaker because I know that if coming from a marketing background and then being you know, in professional services businesses, that so many of us are invited to speak for the exposure, you know, at the thought of saying to someone Well, you know, I get paid X to speak is, you know, people get offended or whatever. So, it’s one of the things that sounds like you did is you you went to corporation. You went to corporate clients, which is a different kind of environment and what people might envision, right. So tell me about your speaking journey.

Ashley: Yeah, definitely. And so I, for me, I’ve all I’ve gotten paid to speak, even before I left my firm. I would get paid small amount and my book Speaker Your Way to Cash is coming out January, it’ll be available to everyone, January 2022. But I share a story in the book that basically says my first paid engagement was for $100. And they gave me a $75 tip. And I literally looked at my husband, and I’m like, oh, my gosh, this is so much money. And it wasn’t because it was a lot of money. But it was because before that, people were just asking me to speak for free. 

So I’m like, oh, well, they actually at least they gave me something to speak. And I think my next engagement after that was $1,000, for one hour, and I after that, it was like, oh, no, there’s a market here, I have to figure this out. And after that, I believe we did an engagement for $5500 for a college. And then we did another engagement for about $13,000 for an hour at a particular University. And then we went to a corporate audience. And we sold like a $35,000 package to them to do one speech. And so it was like, okay, this is like, this is happening.

Davina: I like it. You just show up and you’re just fabulous. Money, and you’re fabulous, which is what you love to do anyway, right? To teach and educate you know. So awesome.

Ashley: Teach and speak. And so for me, it was like, okay, well, how do I, how do I systematize getting paid to speak at the highest level, because a lot of the coaching I saw out in the marketplace, was work your way up from the bottom, speak for free a lot. And then if you’re good, someone will magically be in the audience with a check for you. And they’ll say, hey, I saw you speak so good. I know you didn’t get paid. But now I’d like to hand you 15 grand. And in my experience, that has not happened. And I don’t know if it’s like, because on the speak your way to cash podcast, I interviewed so many speakers, and a lot of them are men. And they always say speak for free. Someone will be in the audience, they’ll give you money. 

That’s how I made my millions. And I’m just like, really? Because every woman that I’ve interviewed is like, no, no, no, this is the strategy that we employ to get this. And so for me, I had to set up an entire sales process. I had to get a list of people that I wanted to sell to. I had to develop packages that were worth 50 plus thousand dollars. And then I had to consistently ask people to do business with me. And for a lot of women that I work with, I always ask this question on my application, you know, how much money do you want to make this year from speaking? And they’re like, oh, one person’s like, you know, a million dollars. Like, I want to make 100,000, just from speaking, it doesn’t matter what the number is. The first question I ask them, when we start working together is like, okay, how many people? How much money did you pitch last month? 

And they’re like, what? How much money did you ask people for last month? Like, oh, well, I sold this webinar for 20 bucks, I’m like, look, if you want to make millions of dollars, you do realize you’re gonna have to ask people for like, a, like way more than a million dollars, you’re gonna have to ask for 10s of millions of dollars to make that first $1 million. And then after you make some money, you’re gonna have to go back and systematize the way in which you’re going to get people to do business with you consistently. The way people are going to how are people going to pay you every month. So for me the way the one thing I would tell anyone listening is yeah, getting paid to speak is great. But the way that our business has thrived, has been from people paying us every single month for the service. So like, they need five workshops in a year. So they pay X amount of dollars per month, or they want to license a training for the year. So they pay $50,000 every year and it renews every year, and we have a conversation with them about it. Even in my law practice. 

Our legal clients pay us between six and $20,000 every month for a certain amount of legal projects. So for me, the recurring revenue is really important even in speaking, but it all starts with what is your proprietary framework? How are you going to change their lives with that framework? And why is it that you have to deliver it and no one else can give them the same result? Because once you can answer that you can basically sell people anything, you just have to have a way for it to make sense for them to. Because you’re not you’re not taking people’s money, you’re giving them an opportunity to make more money with your products or your services.

Davina: So I think you said a mouthful right there, giving them an opportunity and being able to illuminate for them that this is an opportunity for them to make more money. So this would be an investment, not a cost and shifting that belief for them. I imagine you do. You did a lot of work at the beginning. Also being very intentional in who you’re targeting. As an ideal client. Can you tell me a little bit about that? Because I can, I can imagine most people going okay, well, I want to get paid to speak and then going out and, you know, just saying, here’s an opportunity, and they go try to pitch this one without having thought through. Is this ultimately, who I want as a client? Is this what I’m seeking? You know, right? So I’m sure you put thought into that at the very beginning, because you seem very strategic.

Ashley: Yeah, definitely. So for a lot of people, it all starts with your topic. So what are you teaching people to do? Because I have I have a client, for instance, her topic is purpose. Finding purpose. And she wants to teach corporations about how to find purpose, or she wanted to sell to corporations, her purpose, you know, program for their employees. And I was like, Yeah, but do companies care about their employees having purpose? Like, unless your purpose is showing up and making the company more money? No, they do not. So you can’t, but who like then I’m like, alright, your topic is perfect. Well, Who in the world would want their your audience to have purpose, maybe colleges. Because they want their students to stay motivated to stay in school to get the degrees so they can graduate and go become successful alumni. 

So then finding their purpose, or even finding out their purpose is different isn’t a big deal, because when the college students change purpose, they just change majors, they don’t typically drop out of college. So it’s okay for them. They’re not going to lose money from your presentation. But the corporate audience, like look around, do companies care about their employees having purpose? No. So like, as harsh as it is, I think the first step is like being a real being realistic about what your topic is, and finding an on not just finding an audience that wants the topic, but finding a buyer that can buy it. So after you choose your topic, you think about the audience, the topic has to fit the audience, but it more importantly, needs to fit the buyer. So you know, you got to find a buyer, and who are the institutions you could sell to with money? Is it schools? Is it corporations? Is it nonprofits? Is it with nonprofit space, there are some nonprofits that have money, there are several that don’t. 

So you think about the institution, then you think about the size of the institution, because not all schools are going to have a budget, but there are some that will. And once you know a little bit more about your topic, your institution and the size of the institution that you’re targeting, it’s just a matter of getting a list of all of those people that fit within that bucket, and then selling to them, then you need a sales strategy. So as much as people love to speak, because it’s fun, and you change lives. And that’s why a lot of people initially come I’m like, well hold your horses, we’re gonna change some lives. But in order for you to get on that stage, to change some lives, you have to understand sales and marketing. And that is a lot of what we teach and talk about at speak your way to cash. And the method that we’ve developed for helping our clients with that is called the paid method.

Davina: Yeah, yeah. I love it. Fantastic. So, so many questions are popping up in my mind about this. And so one of the things that I thought was very interesting, you distinguish between the audience and the buyer. And I think oftentimes, people conflate these in their minds, when they’re looking at, you know, who’s my, who I want to go, I want to have this big impact in the world, and I want to move all these people, I want to be a heart centered entrepreneur, or whatever, you know, and they go out and they, they have good intentions of changing the world. 

But then they don’t think through well, who’s going to pay for that. We see this a lot, particularly in the coaching space, maybe it’s, you know, different for women law firm owners, you know, and a lot of women law firm owners are focused on growing their business. So what would you tell them in terms of using speaking and how they can leverage their speaking gifts, and a message to attract better clients for their business, their law for businesses and grow that business? What would you say to them? Because it’s a little bit different?

Ashley: Yeah, it is different. So you have to determine what’s your goal with speaking, I like I use speaking in two ways. One I speak to sell. So I may go to a large conference filled with my ideal buyers, and pay like pay to sponsor the conference or, you know, pay my own way to get to the conference, but they let me speak for free or whatever, because I know that the audience, like within 20 people in the audience, I’m going to get two of them to spend at least $10,000. So for me, it’s fine. I’ll get paid on the back end. I bought it consistently to grow the brand of Mobile General Counsel, which is my law firm. The second way that I use speaking in my business is I get paid before I hit the stage. So I a company hires me to come in and do a keynote presentation. 

They’re gonna pay me before or very close in time to the day that I speak, depending on what your goal is. If you’re going to speak to sell like you’re you’re not going to get paid to speak. You just want to go on as many stages as possible. In order to build up your client base. You have to know as much information as possible about the audience and you should be in total control of the stage. So what I mean by that is, a lot of people don’t get paid to speak and they have no control over the stage. So they’re recording you, you didn’t know they were going to record you, you don’t know whether you’ll get a review or a testimonial, you don’t know how many other speakers will be there, your competitor is speaking there. 

There’s 15 other people that do exactly what you do speaking there, like that is just totally out of control. So there’s no benefit to you doing that. If you’re going to speak for free in order to sell your services and someone wants you to speak so they’re inviting you, you need to know. Okay, great. Will I get high quality video footage of the presentation that I can use for my purposes? Absolutely. Will I get at least five reviews from your organization? Will you refer me to at least five people who can pay my full speaking rate? Will I have the opportunity to make an offer? Will I get the email list of all the attendees? Will I get an email blast? Like you have to get what you want out of that situation? 

Otherwise, it’s not worth it. So for me, I’m not showing up to speak. Now. I don’t even I don’t even you know, speak for free. Often if I if someone doesn’t have a budget for me to speak, and they want me to promote the firm, I’ll send my associate. So we’ve recently bought her like webcams and ring lights. And she’s like, oh, now I’m an influencer? I”m like yep, you are. Like I grew the firm with video, you’re gonna grow the firm with video because I’m offloading some of that sales process now and taking that institutional knowledge and transferring it to her. So that’s how we’ll do it now. 

But if I were to go somewhere in order to and I wouldn’t get paid to speak, but I’m going to sell, I need to know the conversion rate. And if I’ve gone there before, I need to be able to trace okay, I went there last year, I only sold one trademark, alright, well, then that means we only got $4500. All right, is it worth going again? No, because you got to pay for flight, hotel, you have to leave, you can’t do any other work that day, you have to leave your daughter, leave your husband, your husband doesn’t go like, it just helps us to be honest about it. Because sometimes I want to do things then my husband, who’s our operations director, he’s like, what did you make last time we spoke to that audience? And I’m like, nothing. He’s like, well, it’s a no. You know, unless it’s for charity, it’s a no. So you have to have a framework for making decisions in your business.

Davina: Yes, yes, I love it. So there’s so many details. So this is, this is one of the things I know it’s gonna be so helpful for when your book comes out. And for your course, because I know that there’s so many people who may be interested in that as maybe a second act of your career, as an attorney to you know, shifting out of that, not just thinking about how they want to promote their law firm business. But you have to, there are so many things you have to think about. And you were sitting there listing off all these, you know, items that you want to make sure you are not leaving on the table that are valuable, you know, that these value items. 

And that’s something I’m sure that has evolved for you over time with doing this. Because as you’ve been a speaker, you’ve learned oh, yeah, let’s not forget. Is there gonna be a good video, you know, is, are they gonna get my best side, right? And so, but it’s interesting to me too, because what you’re doing is you’re really using your skills as an attorney to negotiate for yourself. And I often see, one of the issues that a lot of women law firm owners have, is that they use all their best skills to serve their clients, and they forget to use those same skills to serve their business and serve themselves. Right. So that’s one of the things that sounds like you’ve done in a very smart way of sitting down and saying, what is it that I need to get out of this thing for it to make financial sense for my company. 

It’s a, it’s a business owner’s view of it, as opposed to the speaker in you, who probably loves to speak, anytime somebody puts a microphone in front of you, you got something to say, right? Because you feel good when you do it. But as a business owner, you have to look at it as okay, what I’m sharing has tremendous value. And I need to make sure that I’m getting fairly compensated for that. So I appreciate you sharing that and really laying out some of those details. Because I think, you know, a lot of people might look at a speaker who’s out being successful and getting paid all this going, you know, what was she just speaking for free one day, and somebody from the audience handed her a check. 

And you’ve laid out no, no, no, that’s not how it works, you know, and I and I daresay that didn’t work that same way for those men, they were telling you that. They’re probably just, they’re probably just hoping that you buy that hook, line and sinker. Right. So thanks so much for being here today and sharing so much with us. Tell us how we can follow you stalk you find your find your upcoming book, find your existing book, and just be a general fan of you and the firm.

Ashley: Yeah, definitely. Well, thank you. Definitely so much for having me. I really appreciate it. If anyone is interested in learning more about me or possibly asking a question about how they can get more involved, you can definitely send me a text message to 312-847-4590. 312-847-4590. That’s actually a number that I use to communicate, communicate and connect with my audience. And if you’re interested in getting paid to speak, and you want to start that journey, join us in November for our event, we’re actually I’m coaching advanced readers of my speak your way to cash book for three days in November. So you can go to speakyourwaytocash.com/event

And let me coach you for three days on how to land your first or largest speaking engagement to date. I’m really excited about it. It’s our sixth event. So we’ve done this a lot of times, but this is going to be our largest and most expensive event for us and planning it. So I think it’ll be I know, it’ll be a really good time we have some awesome sponsors we’re working with and the sessions are really incredible and get more into the nuances of what we discuss. How do you sell? How do you market? How do you package it’s a great first step for anyone who’s considering making speaking an income stream in their business this year or next year.

Davina: So where’s the event isn’t in Chicago? 

Ashley: Yeah, so it is we have some we have 50 VIP seats, and some of those have already sold, I think 10 of those are already gone. But we have 50 VIP seats in person, or we have a virtual option. So you can attend from anywhere in the world. Every year we have some international folks attend via the conference. And so we wanted to make sure that was still available and accessible. Plus with COVID. We’re limiting the in person 

Davina: Right, right, right. Yeah, that’s how I was. That’s why I was curious if you were doing it, because I know a lot of people are just clamoring for an in person event. You know, I know it’s been a while since I’ve done one. And it’s like, people are saying, oh, I just want that connection with people. But I’m glad you’ve got a virtual option too, because I know there are a lot of people who just love the virtual option regardless, so great for you to share. And we will be sharing links in the show notes for all of that information as well. So you guys can follow Ashley and try to keep up with her and see what she’s doing, man. So Ashley, thanks so much for being here. I really enjoyed it.
Ashley: Absolutely. Thanks so much for having me.

Davina: We hope you’ve enjoyed today’s episode of the Wealthy Woman Lawyer podcast. If you have we invite you to leave us a review on your preferred podcast platform. The more five star reviews we have the more women law firm owners will be able to positively impact. Your thoughts and opinions are so important to us. If you are a woman law firm owner who wants to scale your law firm to a million dollars or more in gross annual revenue and do it in a way that’s sustainable and feels good to you, then we invite you to join us in the Wealthy Woman Lawyer League. 

The league is a community of highly intelligent, goal oriented and driven women law firm owners who are excited to support one another on their journeys to becoming wealthy women lawyers. We’ll be sharing so much in the league in the coming year, including these elusive million dollar law firm framework that until now, I’ve only shared with my private one to one clients. For more information and to join us go now to www.wealthywomanlawyer.com/league. That’s www.wealthywomanlawyer.com/league. League is spelled l e a g u e. We look forward to seeing you soon in the league.