*Formerly known as Solopreneur: The One-Person Business Podcast*
Welcome to The Aspiring Solopreneur, the weekly podcast that dives deep into the world of solopreneurship. Join us as we bring you insightful interviews with industry experts and successful solopreneurs who have mastered the art of running their own businesses.
Are you a solopreneur looking for guidance on how to attract clients? Or maybe you're searching for ways to stay motivated and overcome the challenges of working alone. Perhaps you're even struggling with the intricacies of taxes and financial management. No matter what obstacles you face, The Aspiring Solopreneur Podcast is here to provide you with the knowledge, inspiration, and practical advice you need.
In each episode, our hosts, Joe Rando and Carly Ries, sit down with a diverse range of guests, including seasoned solopreneurs, marketing gurus, financial experts, and productivity specialists. Together, they unpack the secrets to solo success, sharing their personal stories, strategies, and actionable tips.
Learn from those who have paved the way before you, as they reveal their tried-and-true methods for growing their company of one.
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You guys, we are fortunate enough to have Jessica Lackey on today who brings her infectious energy and decades of expertise to help solopreneurs build authority, streamline systems, and design businesses that actually work for their lifestyles. I know music to our ears as well. If you've ever wondered how to turn everyday efforts into powerful content, leverage workshops as game changing authority builders, or create, like, a newsletter that people actually want to read, then you're in for a treat because Jessica's approach is all about impact, authenticity, and spoiler alert, talking to real humans to unlock untapped potential. So grab a cup of coffee, settle in, and get ready to take some notes because this episode is one you don't wanna miss. You're listening to The Aspiring Solopreneur, the podcast for those just taking the bold step or even just thinking about taking that step into the world of solo entrepreneurship.
Carly Ries:My name is Carly Ries, and my cohost, Joe Rando, and I are your guides to navigating this crazy but awesome journey as a company of 1. We take pride in being part of LifeStarr, a digital hub dedicated to all aspects of solopreneurship that has empowered and educated countless solopreneurs looking to build a business that resonates with their life's ambitions. We help people work to live, not live to work. And if you're looking for a get rich quick scheme, this is not the show for you. So if you're eager to gain valuable insights from industry experts on running a business the right way the first time around?
Carly Ries:Or want to learn from the missteps of solopreneurs who've paved the way before you? Then stick around. We've got your back because flying solo in business doesn't mean you're alone. Jessica, we told you this offline, but we you just exude kindness and happiness, and we it just puts us hosts at ease the second somebody hops on with that. So ladies and gentlemen, we would like to introduce you to Jessica Lackey.
Carly Ries:We are so happy you're here today.
Jessica Lackey:Excited to be here. It's gonna be a fun conversation.
Carly Ries:It will. And, Jessica, I just kinda wanna dive right into it because you're all about building authority and helping solopreneurs, just really establish that reputation for themselves. So I'm curious, what are some lesser used forms of content that can play a role in growing a solopreneur's authority?
Jessica Lackey:So most people have a podcast or a newsletter. Some people have a podcast. The most effective of content for me has been monthly master classes. So every month for free, I teach a 60 minute class. It is not a sales pitch.
Jessica Lackey:It is not a 55 minutes of, like, rags to riches story. It is, straight up, content teaching. And that has been one of the game changers in building my authority and starting to build my reputation is teaching these classes for free.
Carly Ries:And here's what's so funny. I feel like people hear that and they're like, oh, that's content? Like, people, when they think of content, they're like, oh, I need to do a blog post. I need to create a video, which we all love doing. I need to write a PDF or something.
Carly Ries:And they forget that these podcasts, these master classes, these workshops, that is all content and much more digestible content, in my opinion.
Joe Rando:You know, a while back, we started doing events like that as, you know, as content, as lead magnets. And I said, you know, events of new content. I mean, it really, really works.
Jessica Lackey:It serves as, like, 5 purposes for me. Well, maybe not 5. I just made up that number. But, it's a fortune mechanism. So almost all of my classes are around something I wanna learn or teach to my clients because it's a question they have.
Jessica Lackey:And I'm like, I have like a hypothesis, but I don't have a well researched answer. So I go research that for these classes. I probably write 1 or 2 newsletters on the topic. By the way, my newsletters, live on the blog, on the website, and they link to each other. It informs the class.
Jessica Lackey:It informs an illustration I get commissioned for the class framework, which goes into a YouTube video, which makes it into a course that I actually sell or a framework for my clients. And all of that lives on social media in some way, shape, or form. So that's a forcing function to say one idea turns into, like, 5 different assets for my business.
Carly Ries:Can you clarify the commission component? Because I feel like a lot of people would be like, oop, ding. She just referenced a way to make money. What do you mean by that?
Jessica Lackey:So a lot of what I do is visual framework related. Like, I have a framework for how I think solopreneurs should spend their time and where our money should go and marketing cycles. And some of that's really hard to, see through text or just slides. So I actually have an illustrator that I work with on a subscription model.
Jessica Lackey:I send her ideas of what I want drawn or, concepts I want illustrated, and she turns them into amazing illustrations, which go on my YouTube channel, my newsletter, and on my homepage, and in content and classes.
Carly Ries:Yeah. I mean, and repurposing is just the name of the game for solopreneurs because we don't have time. Like, who's gonna reinvent the wheel every time they had to create content? It just not feasible when you have to run every aspect of your business.
Carly Ries:But I wanna circle back because you briefly mentioned your newsletter. Well, a couple of times, I guess. And is it called the deeper business newsletter? Is that right?
Jessica Lackey:Yep. That's right.
Carly Ries:Why did you use that as an authority building strategy instead of, like, a regular email newsletter? Like, tell me how you built this thing because this is kind of a big deal for you.
Jessica Lackey:It is. So my business is 1 on 1, and it really started with high end, I would call fractional COO work, chief operations officer work, or high end 1 on 1 coaching. So around a year into my practice, I had a full roster, or it was full at that time. I had a whole bunch of contract consulting gigs in my 1st year of business.
Jessica Lackey:But at some point, I hit, a ceiling of, like, okay. Well, I'm now full,
Jessica Lackey:Of clients. But so I wanted to continue building an audience, building a list. And I don't remember who gave me the idea, but I wanted my newsletter to be a product in and of itself. I wanted it to be so good that people could learn from it and maybe never pay me, but it was the kind of work that would spread. People are like, this is a newsletter I read.
Jessica Lackey:And because my business model doesn't require, a lot of launching, a lot of selling to that list, it grows just through value. So the deeper business newsletter is an asset in my business. That's a way to both give back to an audience, but help me explore the topics I wanna talk about in more depth without necessarily needing to sell with that newsletter. So it's very much like it's its own asset. It's its own way to give back to the community.
Jessica Lackey:I have a philosophy that, because I came from corporate where, I learned how to do business, but not everyone has that kind of background. And I stepped into this world where a lot of there's a lot of bad actors in the space, charging exorbitant amounts of money for things you can find on YouTube. And I got really tired. I'm like, I wanna make foundational knowledge, not behind a paywall. And I think my business model can make that happen because I don't need thousands of customers. I need 10 a year.
Carly Ries:So for the newsletter, has this grown organically because of the value, or like, did you promotion with it? and same with your workshops. How does that work?
Jessica Lackey:So the workshops almost exclusively grow by word-of-mouth. People come and they're like, wait. You gave this away for free? This is free, and this is useful? Can I bring my friends?
Jessica Lackey:So I do a terrible job of promoting my newsletters, or not my newsletters. I do a decent job of, but my, workshops, I do a terrible job of promoting them just because I'm like, you're on my list. Come bring friends. My newsletter, I grow in a couple of ways. One, I do podcasts like this, to expose that.
Jessica Lackey:I think I did the math. I hit a 1,000 subscribers, like, a month ago. So I have done 30 something podcasts. I've done 20 different guest teaching opportunities, in different communities I'm in. I've been in 15 different communities since I, started like, programs or communities since I started.
Jessica Lackey:So it's a little bit of and I'm on the curve ConvertKit creator network, so I think I've gotten, a couple 100 subscribers from there. There's been a handful of, guest posts I've done, that have generated 20 to 30 new subscribers from each one. And so that's where it's really happened. It's come from, a grassroots effort of going out and building exposure with new audiences through other methods, and then they find my newsletter.
Joe Rando:But you're really focused on kind of talking about the newsletter and as a focal point of your conversations, it seems. Right?
Jessica Lackey:It has become one. I have social media, but I find social media very much for me, it's not a particularly good discovery mechanism. It's a nurture mechanism. And I'm like, well, I'd rather nurture people on my newsletter. But my newsletters have become a little bit of a thing for my audience because they're not just again, they're not just marketing tools.
Jessica Lackey:I'm like, I'm gonna explore a topic. And I write my newsletters for me as much as I write them for other people. I'm like, I need to, clarify my thinking on something, and you're gonna be the beneficiary of, seeing it written down. But I'm like, how do I think about this? And what's my point of view on this?
Jessica Lackey:And what's been noodling around my head that I wanna put down on paper? If I have these thoughts, I'm gonna have people share it and read it. Why not?
Joe Rando:And I'm curious. What is the range of topics that you cover when you go into this? Is it very, focused on a certain aspect of business? Is it any aspect that you wanna explore? How do you think about that?
Jessica Lackey:So my newsletter started off being, I would call, a little ranty. What do I see as, like, kind of, missing from business building advice? But it's very quickly become usually one of 3 different topics. 1 is, about designing business. So, really understanding business models and why helping people understand why certain tactics or advice is not meant for certain types of businesses and why is that?
Jessica Lackey:Why does it certain advice work well for businesses? So business design is one topic. The second topic I talk about is build building business systems. So a lot of people talk about, like, one particular marketing tactic. And I'm like, this is all a system of systems, and I help people think about how we build assets and things that compound in the business.
Jessica Lackey:And then I talk about running the business and, again, how your business model impacts your business systems, which impacts how you manage tasks, projects, time, team management. So whole whole gamut of business.
Carly Ries:Okay. Well, before we move on from the newsletter, we need you to settle a debate that every marketer has. Short and sweet newsletter, long and informative newsletter. Which one?
Jessica Lackey:It depends on your audience. My audience and I think it's part like expectation setting. I write a wildly long newsletter every week. I mean, it's not wildly long. It's like maybe, like, a 1000 words or so like that, maybe a 1000, 1500 words.
Jessica Lackey:But my audience expects it, and I tell them upfront this is what they're getting. If I were to send that newsletter out 5 days a week, like a daily newsletter, I would have lots of unsubscribes. So I think it's, again, what's your promise? My promise is it stands alone. It is a product in and of itself, and I couldn't do that in a 250 word message.
Jessica Lackey:But, if your newsletter is more like short and sweet, digestible things that you send out on a more regular basis, then it has to be short because it has to be like really potent and kind of like the hot tip.
Carly Ries:So you were saying that you write your newsletters for yourself just as much as your audience. And I think this applies to the workshops and everything as well. What role does storytelling have in all of this and your success?
Jessica Lackey:It has a lot to do with it, because I'm always looking at how do we apply this to individuals. Right? Like, I tell this, I'm very public about how this has impacted my business, how this has impacted clients' businesses, not clients I don't name them my name. But, I really think about, again, there's a lot of information in the abstract. How do we make it personal?
Jessica Lackey:How do we make it applicable? And how do we understand the context in which the information is coming and how it needs to be received? So storytelling is a huge part of it. I've been working on storytelling, in my business. I've been working on how to incorporate more of that, why as much as what to.
Jessica Lackey:And that's all kind of it comes through story.
Joe Rando:do you know do you know, of Jay Acunzo?
Jessica Lackey:Oh, he is my coach in storytelling.
Joe Rando:That's very cool.
Jessica Lackey:I've been in I've been in his creator kitchen for a year and a half. I've hired him privately. So, big fan of Jay, and that's who I'm learning storytelling from.
Joe Rando:Yeah. He was a guest a while back on the podcast, and I love his stuff.
Carly Ries:Yeah. We have, a Jay's fan club, I feel like, between Jay Acunzo and Jay Schwedleson . I don't know if you know who that is from email marketing.
Jessica Lackey:I don't. But do you know Jay Clouse from the creator science, the lab? He's another Jay who you would be a fan of.
Carly Ries:Triple J's. We like it. Well, add him to the podcast guest list.
Joe Rando:That's great.
Jessica Lackey:You talk about Jay, and he's been actually a real inspiration, on days when I don't wanna, like, days when I don't wanna ship. I got in with Jay really early on of the kitchen. And part of the reason I write is to think, to write, to think, to write, to think. It all hangs on a methodology. Those are all things that I've learned from Jay.
Jessica Lackey:But this concept of, you have to ship. You have to ship. That's just, part of, authority building and expertise development is being an expert and being an explorer and publishing your thinking. That's what I wanna do.
Joe Rando:What does he say? Something like my newsletter goes out because it's Tuesday?
Jessica Lackey:It's Friday. it's Friday we ship.
Joe Rando:Yeah. And you know, it's not like, oh, I'm feeling inspired this week. And it's like, no. You just you do it.
Joe Rando:And we have the same philosophy here.
Carly Ries:Yeah. And especially for, our LinkedIn post every day.
Joe Rando:And the newsletter. And the newsletter. And the events.
Carly Ries:And the webinar. Yes. We stick with it. But you seem to have some processes in place for how you do everything. We just talked, we're talking right now.
Carly Ries:It goes out on Friday. So how do you help clients set up repeatable systems to achieve goals and profitable growth over time?
Jessica Lackey:Yeah. It all depends on the system, we're trying to set up. And it's all about, again, like the business model. So, one of my clients who's an animal communicator those are like a real thing. Yeah.
Carly Ries:Oh, you have to hire this person.
Jessica Lackey:They're not what I would call an authority based business. Right? They're I mean, they are an authority based business, but they're not probably gonna write, long in-depth analysis of, animal communication. They're gonna build their authority through the doing of the work through, you know, lots of people kinda word-of-mouth and maybe demonstrating what they do through, classes and things like that. Their email newsletter is once a month a reminder of, like, here's what's coming up.
Jessica Lackey:Here's why you should book your sessions. Here's, a resource or something like that because they don't need an authority based newsletter. there's probably not enough content, to warrant.
Joe Rando:I know. I'd like to hear stories about what the animals are saying.
Jessica Lackey:That is true. But yeah. But, with her full practice, it's like she just needs to continue getting a handful of new people in and she has a lot of repeat business. So again, like we always start with the purpose of what you're trying to build and what it needs to do for you, what role it plays in your business. And then we can architect the system around it.
Jessica Lackey:My newsletter, I'm always thinking 3 to 4 topics ahead. I got a couple of things I'm noodling on. I have a system to capture ideas when they come up from clients. Right now, all my clients, said, we know our client. We're not totally nailing who our client is.
Jessica Lackey:They're all doing market research on clients because I teach a cohort, and so we're on clients right now. Do you have great questions to do client research interviews? I'm like, you know, I haven't and there might be out there, but I'm like, I haven't really come across any that are not like for that are not for SaaS based businesses. So let me go explore and let me pull that together. And I can guarantee you that's gonna be some kind of newsletter and a workshop and a YouTube video at some point in time.
Carly Ries:And you mentioned a few things that people often do wrong, not understanding their audience well enough. I hear time and time again, people being like, oh, well, I send out or I'm on Facebook. And you're like, why? And they go, because you're supposed to be on Facebook. They just kinda think that all best practices apply to everybody.
Carly Ries:And so I'm curious with all of your clients and just everything that you do with the workshops, what are the most common pitfalls you see solopreneur space when they're trying to scale without the right systems in place and knowing what they're doing?
Jessica Lackey:Almost all of them have the marketing systems and structures don't match their business model. The big you know, everyone's like, I need to be on social media. I need to be on the platforms. I'm like, well, how many clients do you need, Jenn, really? And there are more effective ways to like, social media circa 2019 was a great way to be discovered.
Jessica Lackey:It's really not anymore. There's much more effective ways for service providers and delivery based businesses to make stronger connections. Social media is a really bad way, in my opinion, for a solopreneur to deepen relationships. All like, the the the people who grow on social media, it's because of their relationships. That's like the relationships came before the social media growth, not the other way around.
Jessica Lackey:And so that's the biggest challenge is, are we building the right systems for our business? And I think usually we're trying to replicate traffic based high volume businesses because that's where our sole openers, that's where our teachers usually run. But actually for us at our stage of business, that's actually not appropriate. it's about relationship building. It's about collaboration.
Jessica Lackey:It's about expanding your network of people who know about you by joining programs and things like that. So that's step 1. And then really step 2 is not understanding the interplay between the authority you need to build, the offer structure you have, the marketing and sales, and how that means you need to deliver. And I think that's where, it gets challenging, particularly as you're trying to scale. If you have built a revenue model that relies on your time and you haven't spent the time to codify, what you do and how you deliver it and decide, do you want to, fractionalize yourself through courses or, leveraged, courses, leverage content, those things.
Jessica Lackey:Or do you want to, scale through others? And do you want to hire people to do client facing work or people to help you run the back end? Those are some of the decisions that people just, fall into. Oh, well, I'm a life coach and I wanna scale, so I just must do a group program. Well, that changes your marketing.
Jessica Lackey:And, oh, I think I wanna build a course. Well, that changes your marketing. Oh, I think I wanna hire a success coach to work for me. That changes your delivery. And so, most people fall into a business model that they didn't anticipate.
Jessica Lackey:And then, something happens in their business that sets them back. So those are the market mismatch marketing and then not understanding the business model that you want to scale with is the 2 biggest pitfalls I see.
Joe Rando:Can I ask a favor?
Jessica Lackey:Yes.
Joe Rando:Could you define because I see different definitions and I've invented my own too. Define what you mean when you say business model. What does it include? What does it not include?
Jessica Lackey:Yeah. So , I'm working on this framework for a while, but, I would say there are 3 axes that I tend 3 and maybe a 4th axis that I tend to see. There's delivery models and creator models. So, like, are you doing services for people, or are you monetizing through, content, essentially, you know, selling a course, selling it monetizing a substack? One is very time intensive.
Jessica Lackey:One is very leveraged. There is, short versus long duration models. So you could have a recurring retainer. You can have a recurring subscription or a community, or you can have a one time high ticket intensive or a one time $25 course purchase. So these are all different business models.
Jessica Lackey:And then there's, do you intend to do it solo or do you intend to do it scaled, through others? The last part is, like, are you selling b to b or are you selling b to c or business entrepreneur? So how complex is your sales process? Combining all those together dictates, what type of things we need to build based on, like, how your business operates. Really sets the frameworks for how your business operates.
Joe Rando:Yeah. No. I mean, I have a slightly different but not totally, divergent perspective on it, but it's just interesting because I look different places and see different things. And, so I appreciate that. That's helpful.
Jessica Lackey:Thank you. There isn't a lot of, and this is where, I'm really passionate. There you know, everyone looks at, like, oh, I must scale like Alex Hermosy, and I must, run like Gary v, or I must scale like the E Myth tells me. I need to, outsource my delivery. I really is really passionate.
Jessica Lackey:I have, like, 7 archetypes that, fit some of these models. But I think there just needs to be more honest discussion about, the fact that you can stay solo, you can stay small, and there's lots of ways to grow your business, without giving up the work you love to do and transitioning into management if you want to.
Joe Rando:I mean, the main thing from our perspective is people are solo because they're not trying to scale infinitely. Right? I mean, why would you give up employees if you wanted to become, Elon Musk or Jeff Bezos? Right? You wouldn't do that.
Joe Rando:So there's another reason. And then you find that reason, you say, well, that's gonna define a size and a workload that makes sense for you. Right? So it's really important to have those pieces in place in your mind as you start to define and grow your business. So I totally agree.
Carly Ries:Did you guys talk offline about Alex Hermozi ?
Joe Rando:No. No.
Carly Ries:So we literally just finished his back. She's grabbing it too for listeners that can't see us for both.
Joe Rando:Oh, you got the leads book. I got the leads book too. It's over here.
Jessica Lackey:I think I bought the $100,000,000 offers book, before I bought leads. But yeah. Like, this is kinda what I do for my clients is, I'm gonna read across every silo of business building knowledge to understand different points of view and, how we can apply that to, you know, expertise based business owners. And what do I like about Hormozi's stuff? What do I not like about it?
Joe Rando:Right.
Jessica Lackey:What do I see as missing? What's the gaps? Where do we fill it in? How do I get a kind of a survey landscape?
Carly Ries:Yeah. That's a really good approach. Well, so knowing all these different point of views, what is one piece of advice you'd give a solopreneur who's feeling stuck, and just isn't seeing progress even if they're trying a bunch of different things?
Jessica Lackey:Talk to humans. That is the unlock I've seen for every one of my clients. You don't know who what you're trying to sell? Talk to people. You don't feel like you're getting enough traction on social media?
Jessica Lackey:Talk to human beings. Anything you can do to decrease the latency of you and another human being, do that. People are like, oh, I don't know who you know, like, they have a list of maybe a couple hundred people or less than that. And they're like, oh, I'm struggling to grow my list. And I'm like, do you know every name on your list?
Jessica Lackey:They all signed up to hear from you. What would it look like if you, over the course of a year, had conversations with every single email address on that list? And what's kind of the insights you wanna unlock and what the relationships you would build? Again, like, that doesn't scale, but we don't need it to scale. We just need to be having as many conversations with human beings as possible.
Joe Rando:I mean, if you look at, the masters of scale, the book by, what's his name? Reid Hoffman. And Reid Hoffman says, in order to scale, you have to do things that don't scale. So whether you wanna scale or not, you gotta do things that don't scale. Right?
Joe Rando:Because you just have to do those things, and it's time consuming, and it's hard sometimes when you have a lot of work to do. But totally 100% with you, you gotta talk to those people. We spent a lot of time doing that.
Carly Ries:Well, Jessica, I knew the second you hopped on, we were gonna like you, and I was right. And I'm curious. You help so many people find success through everything that you do. So what is your favorite quote about success?
Jessica Lackey:So my favorite quote about success is from Patrick Overton. It's, when you walk to the edge of all the light you have and take that first step into the darkness of the unknown, you must believe that one of 2 things will happen. There will be something solid for you to stand on, or you will be taught to fly. Wow.
Carly Ries:I really hope you're reading that and didn't memorize that because I couldn't memorize that, but that was amazing.
Jessica Lackey:I did pull it up. Although in front of me there, I was at an off-site with one of my coach trainers because I have a life coaching background even though I don't necessarily use that. I mean, I am a coach, but I'm a really a consultant. But right in front of me is a sign that says I hand painted it. It says, you will be taught to fly.
Jessica Lackey:And I put that in my view when when I quit my job a couple of years ago, because I knew I could no longer be in my toxic corporate environment. I didn't quite know what I was gonna do next, but I knew I figured out. And I knew that if I just kept taking steps, the path would appear. Now you have to keep the taking steps and you have to, in my mind, ship on Sundays. But, the path has unfolded because I've talked to human beings and kind of put my point of view out there.
Carly Ries:So amazing. Well, Jessica, if people wanna learn more about you, where can they find you?
Jessica Lackey:They can find me at jessicalackey.com/welcome If you'd like to be, taken to my newsletter, you can sign up for my classes. And, if you wanna work together, there's an opportunity to do that too.
Carly Ries:Awesome. I love it. I feel like we have such similar brains from this conversation. So thank you so much for coming on the show. And listeners, we hope you enjoyed this as well.
Carly Ries:You know the drill. Leave that 5 star review, subscribe across any platform, subscribe on YouTube, and we will see you next week on the aspiring solopreneur. Take care. You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes, running a one person business and figuring it out as they go.
Carly Ries:So why not connect with them and learn from each other's successes and failures? At Lifestarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.