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Full Transcript:

Note: This is an original transcript–edited for sense, length, and clarity.  If you have any questions or concerns, please email our host, Doria Lavagnino, at doria@sheventurespodcast.com.

Intro: 

Doria Lavagnino: This woman spent more than a decade coaching solopreneurs and small business owners —  200 and counting, probably many more —  who struggle to sell. I identify with that and that is how I found her; the fact that she talked about selling in a way that is not sleazy. She recently pivoted and rebranded. You will now find her as Quirk Works Consulting. She will still be running the Non-Sleazy Sales Academy. We’re going to go a little bit into why she rebranded. Her work is inspired by helping people like me and a lot of creatives [and] professionals, as well. We’re flummoxed by monetization. The fact that she is working with those that have criminal records and helping them become job ready, which I know reduces recidivism, is so important. I really want to hear from her. She’s so dynamic. What drives her to affect all these changes in people’s lives? Annie Ruggles, welcome to SheVentures!

Annie Ruggles: Thank you so much! I’m delighted to be here.

Doria: I love everything about you! You are amazing. You’re so different than I think what many of us find in the online space. 

Annie: Thank you.

Early Life

Doria: I wanted to explore a little bit since SheVentures is about pivots. In your earlier life, you studied musical theater. I wanted to know [about] that interest.

Annie: Oh, I love theater with my whole heart. I hate competition and not knowing if you can trust your friends because you don’t know if they’re on your team or they’re against you. Also, I hate every single thing about [it] like, “I don’t have any control if they pick me or not.” I could do the best work I’ve ever done and  if I’m a brunette or redhead [and] they want a leggy blonde Rockette, they’re not casting me. That’s how I came away from the theater. 

Let’s start at the very beginning. I am the daughter of a motivational speaker. My whole life, everyone would be like, “When are you going to be on stage with your mom?” I was like, “Never!” Speaking is her thing, right? I had all this exuberant energy. I’m an introvert. As a young kid, if I needed attention, the best thing I could do was get loud, make my face [and] eyes real big. I found that was my self-expression. I was a very quiet kid otherwise. 

I loved to read. I’m an only child. I would soak up a lot of that time. When it came time for, “Oh, Annie’s needs aren’t being met,” and one of those needs being attention, nurturing, praise, validation, or whatever a kid needs, I was like, “I need to do something!” Because I have that performance gift from my mom and other members of my extended ancestry on both sides, that’s how it started. 

[My] dad really fostered theater in me. You hear about stage parents [and] “Oh, they’re terrible —  blah, blah, blah.” It takes a lot to drive your kid to rehearsal every single day; to change your speaking schedule and fly home at three o’clock in the morning so you don’t miss a recital or show you’ve already seen. It takes a lot, but they did it. 

Theater, for me, was never a side job. It wasn’t like this big epiphany. Everyone was going, “Oh, she’s gonna be on stage like her mom.” I was like, “Don’t say that. I sing.” It’s hilarious because now I’m actually speaking and dyed my hair red. I’m basically just like my mom. It’s kind of wild. 

Doria: Own it!

Annie: [That’s how] I learned to read a room. I think that has stayed with me to this day and is where the theater shows up the most. Yes, I’m willing to do zany things on camera. Yes, I’m good at improvising, and I can think quickly on my feet because I’m trained to. Really where the theater comes in is if I deliver a piece of content or if I say something, I can tell how that answer affected you. 

I’m also a trained performer. It doesn’t matter if it’s one person on Zoom or 2,000 people in a room, if I’m not doing my job I can feel it. If I’m doing my job, I can follow it. That’s how the theater has kind of continued —  that love of communication and changing minds. 

If you watch a musical or a play, some of them are light, fluffy, and airy and some of them are dark. Most of the time, you’re there to learn, feel, and unlock something that you’ve been struggling to feel or be inspired by. The way that they do that is because the people on the stage are manipulating you with consent; working with your emotions to provide something for you. That’s what I do every single day. I manipulate emotions with full consent. Now, I teach other people how to connect on a deep emotional level no matter what you’re delivering. 

Theater and Entrepreneurship

Doria: You kind of intuited my next question, which is how has musical theater helped you as an entrepreneur? It sounds like, certainly, it’s helped you read a room. Are there other ways in which it’s helped you?

Annie: Oh, absolutely. One of the other biggest ways is that I’m a natural collaborator. People have this idea about only children and theater kids, and I’m both. The idea is that we’re raging narcissists who are like, “me, me, me, me,” [and] we don’t share.

Doria: Totally, yeah. It’s so untrue.

Annie: I was a very lonely kid. I loved being an only child. In the roles I’ve played, I very rarely go for the star slot. I am almost always [the] comic relief or featured chorus. That’s how I see myself in my businesses. I am not here to run your show, nor am I here to dull your sparkle. I am a consultant, advisor, [and] mentor. I’m going to cheerlead behind you and sing backup for you so that you can take your moment in the sun. I don’t feel slighted by that in the least. I’m a chorus girl. 

That shows up in my podcast. People say, “Annie, why don’t you have a solo podcast? Why do you only do interview shows?” I say, “Well, I have little videos here and there that I do just me.” I have always loved duets [and] choir work. I have always loved singing with and showcasing the band. That’s just how I am, that’s how I work every single day of my life. It’s about collaboration. I learned that from theater. 

Doria: Yes. I totally get that. When I was kind of going through your site —  I found you, I think, a year ago —  I was just like, “Oh my God, this message so resonates with me. I’m still kind of stuck in the same way that I was.”

Annie: Okay, well then you and I need to talk about that off-screen!

Doria: Yeah, I know!

Annie: Hehehehe!

Monetization Struggles

Doria: You’re very open about your own monetization struggles early on. Talk to our listeners a little bit about that. What was that like? And how did you figure it out eventually?

Annie: I look a lot at it as kind of like grade school bullying in that —  hear me out! Grade school bullying is messed up and no kid should have to deal with it.

Doria: Right, but we all do.

Annie: Entrepreneurship is freaking hard, right? It’s a rite of passage in some ways. It sucks. I wish we didn’t have to go through the mean times and struggles, but we all do, number one. 

Number two, when I was bullied in grade school, I made it much worse on myself. I thought, as a 12-year-old, that the best thing I could do would be to conform; they don’t like me, so turn into someone that they do. This is sad, [but] I passed around a note, “What would you change about Annie?” I was so desperate to be liked. I was literally willing to follow trends about it. 

By not being authentic, I made it worse for myself. I feel I made so many decisions as an early entrepreneur where I took the reality of how challenging it is [and] internalized that. I made it about me and went “I’m not marketable enough. I’m not likable enough. I gotta do something else. I gotta double down.” It’s like, “Whoa, whoa, whoa!” 

Grade school bullying is the worst. We all have to deal with it. I’m sorry, I wish we didn’t. Entrepreneurship is freaking hard. You are told that it’s going to be really freaking easy. It’s hard, but how you handle that matters. As an early business, I made a lot of mistakes. I took the nasty landscape and then heaped mismanagement on top of it. Like grade school bullying, it’s something that you’re like, “I have a goal. My goal is getting the hell out of this middle school so I can get to high school and be happy.” A self-actualized 13-year-old and an entrepreneur act the same way: “I’m not quitting today.” 

Looking back, I can see the mistakes that I made. I can see the challenges in the system. They’re so blended. I have to practice self-forgiveness because I was doing the best I could. 

Doing Things Differently

Doria: Yes! I’d like to believe that we’re all doing the best we can with what we know. Looking back, are there two or three things that you could say that, although you’ve forgiven yourself, you’re like, “I definitely would have done that differently knowing what I know today?”

Annie: Y’all, boundaries! Say it with me, audience!

Doria: That’s so true.

Annie: I [would] have new boundaries. The same little 12-year-old who was like, “Oh, you don’t have to pay my full rate. Why would you?” I was working with struggling businesses at the time; all of them were struggling. “I didn’t know how hard you were struggling. You know what? I will take on that struggle for you. Don’t pay me,” or “You can’t meet at my appointed meeting time? Let me just add a whole bunch of more meetings.” It was people-pleasing marketability. I thought it was customer service —  it’s not. Killing your boundaries is not customer service. That was a biggie. 

Doria: Yeah, because it’s not sustaining your business or yourself, which I totally get.

Annie: Right. The other thing that I followed —  and I gotta be really careful here to not come off as hypocritical because I’ve sold both personal development and business development for pretty much my entire working career that has been self-employed. I’m not knocking those things. I have incredible mentors and I’ve bought incredible programs, but I convinced myself early on that I didn’t know enough to do things —  invest constantly. I’d make a little bit of money. I’d spend more than that instantly, right? It’s like credit card debt. As a human being I was like, “Oh, I just paid off $45. Let me spend $300.” I would do the same thing. I would be like, “Oh, well, I’m going to try to launch a Mastermind but I don’t know anything about [it]. I’m going to sign up for a six-month program that I totally can’t afford and have no right to be in.” I’m already financially struggling, have no boundaries, overworking, approaching workaholism, [and] taking every client. I carried that stuff with me forever. I’m still dismantling some of it now. If I didn’t get back to people within a reasonable amount of time, as a 20-something, I’d be like, “Okay, my policies are now I get back to all emails within 24 hours.” WHAT?! Don’t set that standard for yourself. If you have to set that standard, you have to relax it. 

I was rigid. I would let my brand pivot, but I didn’t let my boundaries evolve. I didn’t let my expectations of myself decrease. I didn’t look at how I was treating [myself], as asset number one, in all those pivots. Now, in the last few, I’m finally really getting it.

Doria: Yeah, which I love. What I love about it, too, is you touch on something that I really wanna touch on. There are so many coaches and consultants out there. If I’ve bought something, ultimately I’m responsible for it, because I made that decision and I own it. Many of these things that I’ve bought, except for maybe two, I have not implemented or have not followed through on for X, Y, or Z reasons. There’s always a reason, right? What I wonder is, from your perspective, [for] solopreneurs, female entrepreneurs, or small business owners, how do you recommend that they research a coach, a course, a Mastermind, etc.?

Finding the Right Resources

Annie: Social proof, baby, social proof. You may not know someone they’ve worked with, but everybody’s got [somebody] at that level. Side tangent real quick, ya’ll! Take your testimonials [and] put them anywhere you have an opt-in or buy button. “I don’t wanna click that, why should I? Oh, look, the person right understand said, ’I’m so glad I clicked that!’”

Doria: Yeah, so smart. It’s so obvious when you say it, but I’ve never done that.

Annie: I teach that all the time. The other day when I was looking on my new website, [I was] like, “What’s missing here? A testimonial! Hello!” but sorry [about] that tangent. 

Doria: No, no, it’s so subtle. 

Annie: Everybody that is in this industry —  be it personal or business development —  understands the importance of people. We’ll make those people available. I have clients that will take calls from me all day long. I’m really lucky in that. I have the best clients in the world. I’ve forged that relationship. It’s the most important relationship of my life because they are my livelihood. I invest in my marriage and my friendships. I invest in my clients. It’s the same. I make my clients available.

Doria: Right, absolutely.

Annie: First of all, if you’re buying something from say Amy Porterfield —  who you’re never going to be able to reach —  [and] be like, “Hey, can I buy this thing?”

Doria: Oh, how many things I’ve got from Amy Porterfield. Yeah. 

Annie: Right? What you can do is, you can see who the testimonials are. You can type their name into LinkedIn and you can send them an InMail that says, “Hey, I’m wondering, I know about public testimonials and that’s awesome, but I’m not a very established business yet. I’m wondering if you think this program would be too advanced for me or if there’s anything months later that you’re using or implementing?” Just ask them.

Doria: Right. Yeah, that makes so much sense. 

Get to Know the Customer

Doria: It sounds like another thing that you did really well, that I feel like you’re not giving yourself credit for, early on is that you got to know who your customers were because you were constantly talking to them and serving them. You weren’t just blasting out content.

Annie: Yeah. No, I’ve been in the trenches since day one. I’m a hand-holder, right? I always have this really deep understanding. I allow people to get to know me [as] I’ve gotten to know them. Also, not for nothing, I’ve discovered what a low-key favor is. I think at the very beginning, I was like, “I don’t want to ask people that. They don’t even know me.” Now, I’m like [sending a] LinkedIn message in one second asking for a referral in a program like I picked something out of my teeth. It’s autopilot. I’m like, “Oh, I might buy this thing. Let me know.”

Doria: Yeah, that makes so much sense. 

Hurdles for Female Entrepreneurs

Doria: Also, because most of my audience are female entrepreneurs and your program is for both —  and we’re gonna talk about your rebranding next —  are there hurdles that female entrepreneurs face more frequently than men, and what are they?

Annie: Gosh, there are so many. We can also make the case that men who are really in touch with feminine energy, lead from feminine energy, and queer and non-binary folk also deal with this. As a queer woman myself, there’s a whole other aspect there.

Doria: Absolutely.

Annie: Women have been taught societally to be in “serve yourself last” roles. I always think about my ancestors. I’m very tied to my family history. I was lucky to be surrounded by so many people of my grandparents’ generation when I was younger. My grandparents lived with me. My grandpa was a used car salesman, totally crazy, but wonderfully adored and beloved.

Doria: And very honest, from what I understand

Annie: Oh my gosh, he totally didn’t know how to lie. German immigrant and no clue how to lie. My grandpa wouldn’t know how to manipulate anyone. He just didn’t do it. 

My Aunt Pauline, on the Italian side of my family, would cook Christmas meals for days. She’d be up at dawn [and] sleep when the rooster came out —  cooking over pans, stoves, everything else. Then, the day comes and I would watch her sit at the table while every single member of my extended family went up for not only first, but seconds. She wouldn’t eat. I remember, as a kid, being like, “What gives, woman? You should be the first one because of how hard you’ve worked!” I knew as a kid, “When I’m cooking, I’m licking the brownie batter. If I’m making the food, the first person to taste it is going to be me, right?” I watched her. Sometimes, she would get a meatball. 

Doria: Wow.

Annie: I [was] like, “This is ridiculous! This is absurd.” That is what I see women in self-advocacy professions, like solopreneurship or small business, do. We say, “I will benefit when my clients have been fulfilled. I will prioritize myself when I hit the metrics that I feel like I need to in order to consider myself successful. I will debase myself. I will hurt myself for the benefit of the client because that’s the caring, compassionate, womanly thing to do.” It’s like, “Whoa, whoa, whoa, whoa, whoa!” Ain’t nobody in my family would have gone hungry if Aunt Pauline would have made a plate.

Doria: Exactly. She was told, “Don’t take up too much space. Don’t make too much noise.”

Annie: Yeah, it’s better to give than to receive and all that stuff. What I tell my clients now is, “Yes, give more than you receive. That doesn’t mean give everything and receive nothing.”

Doria: Amen, sister.

Annie: There’s a whole landscape, right? It’s like no one in my family would have gone hungry. Did she really need to wait until everybody had had seconds? I’m sure I’m not the only one who felt guilty eating and watching her not eat. It hurt the pleasure of the food. I was eating, watching her not eat. How mindful could I be, right?

Doria: I was wondering because the rest of your family also allowed that to happen. 

Annie: Yeah, and that’s so funny because I think my family was in two camps of like, “There’s no use trying to argue with her. She’s gonna do what she wants to do, so I’m gonna eat my meatballs,” and then there’s the rest of us being like, “Oh, I am modeling this behavior, but also it sucks that I need to model this behavior.” For me, I would just take a meatball and stick it on her plate and be like, “Eat, please.” I was a 5-year-old. Then, in the early years of my career, I could have said the same thing to me.

Doria: Yeah, right. It’s not like we’re exempt. We do the same thing.

Annie: It’s interesting because what I see now, back when I started figuring out what I wanted to do in like 2009, entrepreneurship was a very different landscape. Pam Slim’s (who I freaking adore) Escape from Cubicle Nation had just come out, and Chris Guillebeau’s World Domination Summit had started. All of these things that we know and love weren’t there yet. Marie Forleo hadn’t even really launched. All of these things that are prevalent in our lives didn’t exist. I didn’t have the same atmosphere that new businesses or evolving businesses have now. 

I thought, from a marketing brain, if I’m the most cost-effective on the market, I’ll sell the most. I went as low as tickets could possibly go; “bargain basement” prices that I would let people negotiate out of. Over-delivery was the norm. It was like a weird martyrdom in my business. “Look how noble I’m being by giving so much. Surely if I give and give and give, I’ll learn to receive in the process.” Nope, sure didn’t. 

People coming onto the scene today, in this very established, saturated landscape, are almost immediately forced to go extremely high-ticket and razzle-dazzle from the jump; show up authentically right out of the gate. I don’t know which situation was better. They both have their challenges. It’s really interesting. 

Although, undercharging is still a really big thing with women. I now see a whole other problem. Where, before, it was women being like, “Hold on, let me be Aunt Pauline and serve and serve and never receive.” What I’m seeing now is, “Do I really have to charge $20,000?” Receiving is weird at this rate. I’m like, “No, you don’t have to start at $20,000. Start at $25.” It’s a pendulum. Let’s find something in the middle here between being the cheapest coach on the block and going directly to premium exclusive. 

Doria: So true, and you’re right, that’s what I found is that they run the gamut because I think I’ve pretty much done them all at this point where I get in with either a freebie —  they get me that way —  and then they have my email and it’s the whole nurturing thing. I’ve had it done to me so many times that I allow it. That’s where I guess I’m struggling. What attracted me to you is the Non-Sleazy because that is how I, for some reason, internalize sales. You’re right, it’s not noble because if you can’t keep your business going, then what’s the point?

Annie: Right, it’s self-torture at that point.

Doria: Exactly.

Annie: I was in a play in college called Self-Torture and Strenuous Exercise —  a great play. That was early entrepreneurship for me:, self-torture and strenuous exercise, 100 percent.

Realizations in Rebranding

Doria: Yeah, so now you’ve rebranded. Talk to us a little bit about the realizations that you’ve had —  whether big or small, whatever they were, where you are, what you’re going to be calling yourself, and what you’re going to be doing.

Annie: The Non-Sleazy Sales Academy is the best brand I have ever launched in terms of its resonance. I’m not surprised. I’m grateful that it clicked with you. How I got out of over marketing and under delivering was I realized that I wasn’t selling. All the nurture sequences and that stuff, I love [it]. In my previous iteration, the idea of a doula was what I was doing for new businesses. That’s why I was a doula —  I was birthing these new ideas, funneling them, and doing all these things. I realized that I was marketing specifically to struggling businesses. All of my stuff was in this kind of struggle narration, which also worked with the doula stuff. I’m like, “Childbirth is challenging. You’re birthing a business.”

Doria: Totally. Great analogy.

Annie: I loved it, but it wasn’t really clear to the point of resonance. I would get calls where people thought I was an actual doula, I only worked with women or I only worked with new business. I was like, “Uh-oh.”

Doria: Understandably, yeah.

Annie: Everyone around me had the best marketing imaginable. We worked hard on it and all of us were still broken. I was like, “Okay, first of all, fix the marketing, not to be so struggle-centric. See if that fixes it.” It didn’t. I was like, “What improved it but didn’t fix it? What’s happening here?” On a whim, I said to my doula clients, “Hey, send me your most recent sales call.” Half of them said, “What’s a sales call?” I was like, “I’m gonna jump off a bridge.” Then, the other half said, “Oh, I don’t want to send you that. I know they’re not good.” I [was] like, “Herein likes the problem.” 

I looked at my own selling practices. I read 138 sales books in rapid succession. I was like, “Look, I have misconceptions about this. I know good people that are killing it. How do I figure out how to do that in my way?” I still wasn’t anticipating teaching sales fully until I realized that every time I was like, “Hey, I’m launching this thing about non-sleazy selling.” They [were] like, “I needed that yesterday! Where has [this] been?” I took all my marketing stuff and told my clients, “I am not doing funneling, copyrighting, marketing, positioning, branding —  any of that —  anymore. I am taking up space in this new lane.” It worked well for years. I loved it. 

The challenge with the Non-Sleazy Sales Academy —  and the reason I’m pivoting and it’s a different pivot than ever before —  is, normally, I pivot based on a need in myself or the market. Number one, I’m still dealing with the stigma of sales, [and] stuff like my book is working against [that]. We’ll get there. [Number two,] you have to follow your zone of genius, right? You have to follow not your zone of confidence [or] competence, [but] your zone of genius. 

What I’ve realized is that I’m still a marketer. I’m good at teaching sales, but I’m still a marketer. The work that lights me up and the clients that want to work with me are people that go to my website, even if it doesn’t say I offer marketing. They say, “Your site is so good, I want one,” or “Your program is marketed so beautifully,” or “Your book is so weird. I want one.” 

What I realized for the first time [is that] I’m not doing a complete rebrand. I’m branding backward —  meaning the new brand, Quirk Works. 

Doria: This is getting very metaphysical here.

Annie: When I started telling people I [was] going to rebrand, they [were] like, “No! It’s lazy.” I [was] like, “No, no, no, no. It’s not going anywhere. It’s changing.” It’s one piece of my menu now, it’s not the whole restaurant. 

I’m naming [it] Quirk Works Consulting. The way that I came up with that is I started as a life coach [and] shiny theater kid —  a manic pixie dream girl for hire, right? That was handheld customer care. At the beginning of coaching, because of the hand-holding, it was successful. People wanted to know how it was successful. They assumed it was my marketing. They started hiring me for [that]. I love it. The marketing was failing everybody because we weren’t selling. Then, I started teaching selling. Now, all the people around me are killing it because we all know how to sell beautifully. 

I’m trying to give myself an expansive brand I can play that appeals to the product base. Also, for me, [it] has to show the through line of my work. 

Doria: Yes, and, interestingly, you say that because one of the things that I always hear is “The riches are in the niches.” That sounds like that’s where you started, but then you also realized that you have more breadth [and] that your clients need more breadth of support. That’s something that is where your gift lies.

Annie: I niche by people. I niche by psychographics more than demographics. I niche by problem-solving. People ask me, “What’s your niche?” I say, “Highly empathic, sparkly but struggling” —  whatever struggle means to them. Solopreneurs, small business owners, and service providers struggle to give and receive simultaneously. [They] want to do things their own way. I know those people so well. I could spot them in a lineup. I’ve surrounded myself with these people. 

I will never say, “I’m only going to work with coaches.” That’s not it for me. I have no problem with people that only do that. I don’t only do that. That’s not what I do because I have found highly empathic, heart-centered, do-gooders in men and queer people. For me, that’s how I want to serve. I agree with the “riches and niches” that we need to be specific about who we’re serving, what problems we’re solving, and [what] niching you can [do]. I just call that good old brand differentiation. 

Doria: Yeah, you go old school. You’re right, that is what it is. There are so many bells and whistles and terms. It’s so easy to get overstimulated when one’s starting today, right? 

Social Media Platforms

Doria: You mentioned that you started more than a decade ago, [a] very different, very saturated landscape. Is there a specific social media platform that you have found [that] works for you? Does it depend on the person? 

Annie: It depends on the person and the problem. However, I am a high priestess of the Church of LinkedIn, y’all. I never expected it. I am a shiny, weird theater kid. You may not think someone like me would be like, “You can leave all other social media behind if you focus on LinkedIn.” 

Doria: It’s true, though.

Annie: Love me some Instagram. It’s the one where I have the most personal pleasure other than LinkedIn. Seriously, I love LinkedIn.

Doria: LinkedIn, if you’re listening!

Annie: No kidding, sponsor this podcast! I have basically collapsed my Facebook. I’ll repurpose content over there. I don’t do a whole lot on Facebook. I have dabbled in Pinterest. I have clients that have done more. I have dabbled. I’ve done more. I run a show, so I have some YouTube videos. 

Doria: Do you do it all yourself? 

Annie: I do a lot of it myself [and] I have to delegate other things. I enjoy doing my social media. In the past, it [has] hurt my social listening. I sort of just “set it and forget it,” because somebody else is doing it [now]. I’m getting really good [at] comments and engagement. 

Part of it is self-policing me to be like, “You can’t make shiny things and put them on the Internet. If you’re trying to start conversations, go have them.” For me, [it’s] what my mentor calls the “time pie.” I don’t mind that part of my day is creating and putting out my own content. That works for me. [What] doesn’t work for me is a lot of the other admin stuff that [other] people don’t mind. That I’ll delegate all day.

I focus on LinkedIn. My Instagram is “set and forget.” I just remind myself to go look at it and engage in the conversations. I also have processes around social listening on Instagram. My Russell Brunson Dream 100, for folks familiar with that, is on Instagram. The difference between Instagram and LinkedIn is that if I go into my Instagram feed right now, I’m going to have pictures of people’s dogs, babies, influencers, etc. It’s not streamlined in terms of purpose. I could be going to Instagram specifically to watch an hour of Shabaz Says reels because I adore them and need to laugh. If I’m on LinkedIn, I am there to connect [and] learn. That’s it. 

Doria: Yeah, absolutely.

Annie: If I see business content, teachable content, or educational content, I’m a lot more likely to stop and absorb it. If someone is introducing or featuring another person, I’m a lot more likely to hang out on their profile for a while, get to know them, maybe even connect with them, [and] send them a message. 

Doria: It’s true.

Annie: On the connection front, it’s so easy.

Doria: It is.

Annie: When I get tagged or something on Instagram, I’ll get a couple of follows. When I get tagged on something on LinkedIn, I get a ton of followers. LinkedIn is the only platform where, if I put something up and you liked it, it goes into their feed. No other platform has the bandwidth to do that. LinkedIn can do stuff like use a part of the algorithm to show what other people are liking. Could you imagine if Facebook did that? 

Doria: Oh my god. 

Annie: We could be drowning in third-party whatever’s, but because LinkedIn is naturally curated, it’s okay.

Doria: Yes. I love hearing what you’re saying because I gravitate toward LinkedIn, as well. I just get the most ROI (Return on Investment), at least in terms of engagement. That’s helpful to me. I, also, think that what I’ve heard when you’re starting, if you try to do social on all the different platforms, you’re going to completely overwhelm yourself [and] spend all day doing just that and not figuring out how to do anything else. 

Annie: Yeah, and your bandwidth and your energy management matters.

Doria: Completely.

Annie: I mean, we can look at this strategically and energetically, right? You could add that whole layer for the woo-woo people out there. Strategically, if we wanna have an omnipresent message, [then] sure. That’s where the idea of being on every channel comes from, but you can do that in a more lean way than you think by creating a vortex of your content. 

Have your podcast, have that go out, and showcase people differently. You could do that in a much more lean way than, “I need to be on every single platform.” Number one, you might be diluting your message instead of amplifying it, especially if you’re putting out subpar content because you’re so busy doing everything. That’s the strategic side, energetically, on a point of recording. There’s a quote on this week’s version of my podcast with Joy Bufalini who says, “80 percent of marketing fails because the founder doesn’t want to do it.”

Doria: Yeah, that makes sense.

Annie: I could not agree more. I have run some amazing Facebook groups. I loved them until I hated them and once I hated them, I hated them and yet it was in my time pie. I [was] like, “Oh, why am I even here? This isn’t converting, this is so stupid. I don’t even like this.” Then don’t do it. If it’s an important part of your strategy, you can find someone to delegate it to or don’t do it.

Marketing Tactics

Doria: If you had to choose between email marketing and organic social, which one?

Annie: Social, but one of my favorite models I ever heard is “Choose your hard.” I would choose social. [Without] my nurturing and everything, [it] would be wildly different. It’s easier for me to get people onto my email list through social. I would favor my top-funnel over my mid-funnel. If I had to sell somebody in a DM, I wouldn’t DM them —  they DM me to do that. I would need new people to make the engine run.

Doria: That makes perfect sense. ChatGPT —  I wanted to ask you about it. Do you think it’s gonna do anything to marketing at all?

Annie: Unpopular opinion: I think it’s great.

Doria: It is pretty great. 

Annie: As a marketer who does my own marketing, it’s great. As a strategist, not that it’s gonna be awesome, but you can go in and you could type into ChatGPT right now, “Outline an eight-module program on personal development with an emphasis on Reiki.” It’ll just be like, “Cool.” People would come to me and say, “Outline an eight-module course about Reiki.” I’d be like, “Okay cool,” but I wasn’t really outlining the course. I was looking at how the problems flow. I was looking at, “Now that they’ve done this, what can they do now?” I was looking at the energetic flow, packaging, and customer delivery. ChatGPT cannot teach you how to be a good coach, write copy that sounds exactly how it is coming off your head and heart, [or] teach you customer service.

Using AI for Good

Doria: What ChatGPT can do is be an incredible brainstorming partner. Incredible. 

Annie: For example, in this rebrand, I had an orange and green color [scheme] that I loved, and no clue how to build a color palette around that. Guess what I did? I put those hex codes into ChatGPT. I said, “Recommend colors that are bright and warm [that] go with these colors.” What did ChatGPT do? “Right away, Annie, here’s the whole thing. Here’s the thing!” I still gave those hex codes to a designer, too.

Doria: Sure, but it saved probably three hours, right?

Annie: Tons of time! I have clients that I am their fractional CMO (Chief Marketing Officer) for. They come to me with marketing. [It’s] much faster for me to edit and perfect [it], whereas they would have spent hours writing an email that ChatGPT can write in minutes. ChatGPT is my junior copywriter. Then, they give it to me to fix it. It takes the same amount of time, and I make the same amount of money, but I get to do deeper work. I’m not mad about that. [The] same situation for me is if we use a lower-level copywriter. It’s not like there’s not still work for those people; there will always be work. 

Doria: There has to be. 

Annie: I’m still using my whole team. I’m still getting paid. My favorite use of AI isn’t ChatGPT. It’s Capsho.

Doria: I’ve heard of that.

Annie: Well, you should! It’s specifically for podcasters.

Doria: Isn’t it about transcripts?

Annie: It’s beyond transcripts. I’ve also met the founding team, [because] where my money goes is extremely important to me. If I [am] able to meet the team or engage with [them], then I’m gonna feel better. The founders of Capsho are incredible. I’m glad to endorse them. 

I was complaining to a friend of mine Danielle Weil —  incredible copywriter —  [that I was] worried about ChatGPT. I [was] like, “I hate writing podcast show notes so much. I hate it.” At that point, I was listening to all of my episodes back twice; once for a general gist [and] then I got to write show notes and everything else. I [was] like, “If I could find something that would help me write show notes, I’d be so happy.” Then, I saw this big beautiful sign that said, “AI for Podcasting.” The first thing on the bulleted list was show notes. I had my credit card out immediately. I was like, “Excuse me, does this do what it says it does?” They were like, “Oh, yeah.” I was like, “Does it actually listen to the episode?” 

At this point, I can copy and paste the text into ChatGPT and say, “What is the tone of this? What are the themes of this?” I could go into another transcriptionist and be like, “Hey, get me a transcript for this.” There wasn’t anything going, “Let me use AI to understand what this episode is.” Now, I put everything in Capsho. Not only does it recommend all my social stuff, it tells me the themes of the episode, pulls quotes for the episode, [gets] timestamps of the episode. It does all of these things. I’m still going to rewrite the paragraph it gives me, but I can get ahead of my podcast marketing. I don’t have to spend three hours listening to everything twice and then writing. I put it in, I look at the summation they give me. It refreshes my memory. 

Doria: Yes, exactly.

Annie: It cuts everything down and makes it easy for me —  as we already talked about —  to do my own social. I want to have an executive eye on what quotes we use. That doesn’t mean I want to listen back and have to write all the quotes down! Capsho serves up like 20 different quotes and I go, “That one, that one, that one, not that one, that one, that one, not that one,” and I’m done!

Doria: Yes! Good to know. I’m going to re-check it out because I saw it maybe early on and I was like, “I’m not quite sure what this is,” but obviously it’s something I need to do.

Annie: They did a whole launch. That’s an example of how AI’s getting used, and not for nothing. Most writers and marketers have been playing with AI for a long time. We can embrace our robot overlords and we can fear them. I’d rather collaborate with them and then give people —  whose jobs they’re replacing —  better things to do with their time [and] my money.

Doria: I love it. I love your mindset. 

Professional Wins and Regrets

Doria: I want to know more about how people can work with you. What would you say is your biggest professional win and your biggest professional regret or mistake?

Annie: My biggest win is twofold. I can’t separate them. One-half of it is that I’m still here. Businesses come and go, I’m still here. Talk about musical theater —  there’s an incredible song written by Stephen Sondheim called “I’m Still Here”: “Good times and bum times, I’ve seen them all, and my dear, I’m still here.”

Over a decade later, I’ve pivoted 750 times. It’s a privilege to pivot. It’s a privilege to struggle in this way. 

The other thing is, because I’ve been doing this and relying on myself for, 13-ish years now, I’m so deeply embedded in the root of my business that I don’t have to worry about being authentic. I don’t know any other way, right? Not only am I still here, but I’m also still here [and] true to me —  not grade-school fake-smile me, not guru-ed me. The me that you’re interviewing now is the same me that’s going to go celebrate my husband’s birthday later. It’s the same me that clients are gonna see later. I feel like relying on myself through all these years has made it so that I only know how to show up as me. I’m grateful for that because now that’s what people resonate with. They love the Non-Sleazy brand —  they come in for that —  and they stay for me.

Doria: Yes, that’s very validating.

Annie: It is. My mistake is sales avoidance, 100 percent. It’s all the things that sales avoidance is. It’s undercharging, rapidly discounting, relying on gimmicks, trying to do sharkish sales policies —  because you paid a really expensive program and that’s what they did to you, so you figure it must work. It’s all of the things that we’ve talked about that stand between you and compensation. The reason I wrote a book about it, the reason I know about it, the reason I’ve dedicated [to it] is I’ve watched it kill so many businesses, including almost mine. 

I got an autoimmune disease so severe that I’ll have polka-dotted skin for the rest of my life. I look like a cheetah. That’s what happens when you over deliver occupationally for a decade. If I had conquered my sales avoidance faster, my health would be better. My financial health would be better. I would have less credit card debt and sleep better at night, but I’m fixing that still. What I regret is I wish I had allowed myself to sell well faster. I wish I had prioritized my own receiving so much earlier.

Doria: I’m speechless. It really resonates with me. Let’s wrap up by letting people know how can they work with you.

Annie: With the rebrand, the Non-Sleazy Sales Academy is becoming a selling seminar. I’m also going back to helping people own their weird, which is what Quirk Works is all about. A great way to come into my world is twofold. If you are struggling in your business right now, what I want you to do is I want you to go to SellCoachSell.com, even if you’re not a coach. I want you to redeem your copy of my noir sales novella. I tried to write a sales book and I just couldn’t. If any of this stuff is resonating in a touchy way —  like “Oh, I need to fix that,” —  that’s my gift to you. That’s the book that I needed when I was in that spot. 

You can find me on Instagram. I’m anniepreneur. If you want to learn about me, my podcast, my work, my people, my work fam, my clients, or any of that: Annie P. Ruggles on LinkedIn. Don’t just follow me, connect with me. If you want super-duper bonus points, connect with me —  send me a message and say you heard me on this show!

Doria: Aw, thank you! This was such a great conversation, Annie. Thank you.