“If they teach you how to build a business, you stop buying their stuff. That’s not what they want.”
– Jessica Lackey
A lot of business advice is a slot machine dressed up as a strategy.
Jessica Lackey‘s book Leaving the Casino lays it out cold: the entrepreneurial industrial complex isn’t, in fact, designed to help you build a sustainable business. It’s designed to keep you spending money on the PROMISE of one.
She and Anna get into:
- Why and how the casino targets the most vulnerable entrepreneurs, MLM-style
- The zone of enoughness: how to define your minimum and maximum across money, time, schedule flexibility, and creative autonomy
- Why “just raise your prices” might be the most misplaced advice in the industry, and what to actually do instead
- The difference between slowing down your activity and slowing down your expectations
- Why if your marketing isn’t working, it’s probably your market, not your mindset
ACTION ITEMS:
- Do you know your “enoughness” number? Not “I want to make a million dollars,” but the actual breakdown: mortgage, groceries, fun, vacation, retirement, etc.
- Where in your business are you trying to move faster than your growth can actually support? What would it look like to metabolize what you already have before adding more?
- If something in your business isn’t working, have you interrogated whether it’s a you problem or a market problem?
•
Strange Birds is a worker-owned cooperative of strategic messaging partners. We help small yet mighty teams figure out what actually needs to happen — and then we go do it with them.
Most partners bring only thinking or doing. We bring both to your big idea, and we stay until it’s shipped.
•
Listen anywhere podcasts roost (except Spotify).
Watch on YouTube: https://youtu.be/thrYK_KW3-s
Learn more about Jessica Lackey: https://www.deeperfoundations.com/
Learn more about Leaving the Casino: https://www.deeperfoundations.com/casino
Follow Jessica Lackey on LinkedIn: https://www.linkedin.com/in/jessica-lackey/
Subscribe for new episode drops, show notes, our secret insider thoughts on the interviews… and the occasional goof reel.
Read the raw transcript:
[00:00:06] Anna: Welcome to Flying the Coop, a podcast about rethinking how business works and who it should work for. We’re normally Janel and Anna, small business owners learning in public as we turn our company Strange Birds into a worker owned co op. But today you’re stuck with just me, Anna.
Today I’m talking with Jessica Lackey, author of Leaving the Casino: Stop betting on tactics and start building a business that works.
Jessica’s work sits at a really interesting crossroads. She spent time inside traditional high status institutions and she’s also been deep in the world of online entrepreneurship. In her book, she names something many of us feel but struggle to articulate, that a lot of modern business practices are built more around feeding our inner dopamine monsters than they are around care or sustainability.
We easily find ourselves asking what will perform instead of what actually matters right now.
So what I like is this book widens the lens outside of just the business to clients, teams, community, the broader systems we’re participating in, whether we mean to or not.
All right Jessica, to get to our interview, let’s start with the story that you share at the beginning of the book. Your own wake up call of being in the casino. You’re lying in your bed, you’re scrolling before 8am Your check in bank account and feeling like this big weight. What was that weight that you were feeling?
[00:01:34] Jessica: I mean it’s this feeling of the sinking in your stomach, the, the pressure on your chest, the looking at your bank account being like, I made money but it’s all going to somebody else. And so that was the, that was when I woke up and I said, you know, I, I was the pressure of feeling behind the pressure of like they have a secret, what do they know that I don’t? And that pressure was real for many, many years of building my business.
So that was the, the genesis of the book.
[00:02:11] Anna: Yeah, and I totally get it. So when I started as an entrepreneur, you could just get flooded with courses and PDFs and webinars and buy this, invest in that. You have to invest to make money. You have to spend money to make money. You have to invest, invest, invest.
Can you talk a little bit more about that? Those like hidden costs of operating inside. I would say traditional online entrepreneurial practices.
[00:02:39] Jessica: Some of the more outlandish spends did not make it into the book because I was not about to tell my parents how much money I spent on online entrepreneurship. I side hustled for three years as a first, as a try to become a holistic nutritionist. Then I wanted to Become a life and leadership coach. And then I transitioned in my full business full time. But my kind of like third website was someone from my local community who’s like, I’ll get you a website that will sell you clients in your sleep. And I spent $10,000 on said website because people had, in my world had trusted this person.
And when the website was handed over, the web copy was just Lauren Ipsum, you know, the Latin placeholder. And I was like, the branding was fine. The website itself was fine.
The copy, which is actually what sells, was missing or misspelled.
[00:03:40] Anna: And I was like, what the heck
[00:03:42] Jessica: am I doing here? Why did I spend all this money on this person?
You know, five years later, I’ve also spent $10,000 on my website.
Completely different experience because I knew what the hell I was doing. And I had. I went from like needing four pages to like 20. So like, there’s a difference, but between the super expensive website, the $25,000 mastermind, because that’s what you needed to do to accelerate your success.
I’m thankful that I was not. I didn’t go into debt because I had the capacity to take on bridge employment. So I was. While I was trying to build my business in the more the online way, I was doing consulting gigs from my old previous corporate network, which meant I was spending 20 hours a week getting paid from my old work. Spending 20 hours a week in my business.
And. Cause I have the capacity to work 40 hours a week.
And so I had the cash flow to afford to make some of these mistakes.
But then I looked around the rooms I was in and I’m like, oh, most people don’t.
And this is their entire like paycheck for the whole year is going to somebody else who’s selling them a dream.
And I fell for it.
[00:04:59] Anna: I mean, as we talk about it, it’s really clear this. This metaphor of the casino. I know quite a few people that got caught in the trap of like, I just need to invest in the next thing and then I’ll figure it out. And then I’ll figure it out. And then I’ll figure it out. So talk a little.
What that feels like. That. That rush and then the down. And then I’m just gonna gamble again.
[00:05:20] Jessica: Well, you think about, you walk into a casino and it’s noisy and it’s shiny and you’re just surrounded by all these promises.
And you know, the casino itself, like a physical casino is designed to short circuit your agency, right? There are no clocks, there are no windows. The food and the drinks keep coming and all you are doing is being surrounded by people having their best day ever, right? Like no one. You know, you hear the cheers, you don’t hear the, the silent let me go re up at the ATM kind of mentality, right? Your comped food and drink and beverages for your big spenders, you know, which is kind of like the free summit ticket that’s, you know, just, you know, come explore this free thing and then let me upsell you some amazing package that you have to buy. But when you look at the casino, two things become true. One is the house always wins, right? The goal here is not for you to be successful. The goal is for the house to make money.
Some people are successful if you have an intention and you are thoughtful, you can go there, get what you need and get out. But that’s not what it’s designed to do. And also if you are very well capitalized, know like the card counting teams, you can play the game, recognize the edge, adapt the odds to your, you know, think about Gary Vee and Cody Sanchez, how much money they spend on content teams and then win, right? House don’t like that very much and they, they kick you out. But the idea that everyone in this industry is seducing you with promises of success, encouraging you to again, keep investing and keep investing, win.
The house wins. If they teach you how to build a business, you stop investing in their stuff. If they teach you why you don’t need this program because it’s not meant for your business model, you know what you won’t do, you won’t buy that program, right? Like the amount of programs that I don’t buy anymore because I’m like, that’s not how I grow my business. Do I need your reels course? No, I’m not on Instagram, so I don’t need your reels course. Do I need this program that’s gonna help me grow my email list If I sell B2B through relationships, that an email list? No, I do not.
But if you know what game you are playing and you know the rules of your business, you know how it works, you don’t buy their stuff and that’s not what they want.
[00:07:39] Anna: This has made me think of early on in my entrepreneurship journey. I mean, I, I, I was pushed really hard to join a mastermind and I kept saying no one because I have al always, always been obsessed with budgets. So from day one, I knew my numbers and that’s something that we’re going to get to in a second. But they, they Couldn’t handle the fact that I was like, I can’t afford this right now. And they’re like, but you need to invest to make money. And I’m like, no, I am making money.
I’m not ready for what you’re selling me. I might come back in two years and I’ll be ready. And I did come back in two years. And when I, when I, I did join, it actually was the right time. And it, I think it was helpful said slowly, but it was also something that I felt like I had to do. Like, everyone at the level that I was at had joined a mastermind. And I was like, I haven’t checked that off the box. Like, maybe I should join.
So I kind of want to talk about, like, sometimes you talk about how choice and entrepreneurship sometimes feels like it’s kind of an illusion. How do you know when it’s a choice and when your system is getting hijacked by all this messaging of like, in order to be successful, you must do xyz.
[00:08:54] Jessica: I think we operate in an entire world that is designed to hijack your attention. Like, that is the entire point of technology. That is the entire point of social media. So I think you have to operate under the assumption that 99 of things you see on the Internet are designed to hijack your attention. Like, full stop, we have to go back to how business really works.
What does your business need right now? Sometimes you need to invest in point solutions to fix problems. Sometimes you need to invest in community. Right? Like, I have invested in a lot of communities because that’s also how my business has grown. But I think we, we want to go in operating an assumption that almost everything on the Internet is designed to hijack your attention. Our responsibility as business owners is to slow down, think more critically about what does my business need right now. This is the truth about solopreneurship. There is always more to do than you have capacity for. There is always more things you can do.
My job and part of the work I do is to help people recognize that, yeah, the list of stuff you need to build is like five years long. Trust me, I built it over five years. And it took me five years to do all the things I needed to do.
But spending more money isn’t going to make that go faster. In many cases, you’re not going to be able to move faster than the speed of your own growth. And I have spent more money on investments to accelerate that that I couldn’t metabolize because of my stage of business.
[00:10:23] Anna: So it’s Really?
[00:10:24] Jessica: I, you know, like, sometimes I’m like, it’s the right investment at the wrong time, which means it’s the wrong investment.
But I think we have to operate on the assumption that everyone here is trying to convince you to part with your money.
And it’s your job to build your own business acumen and detach from the dopamine cycle. To say, whoa, whoa, whoa, whoa, whoa, whoa, whoa, whoa, whoa, whoa. What do I actually need here?
[00:10:44] Anna: I. I’m very hung up on, on this word that you just use, metabolize.
I think, you know, I come from, from the marketing side. That’s, that’s my skill set in the Strange Birds team.
And everyone wants the silver bullet, right? If I do this thing, my business will take off. And it almost never works that way. It always takes way more time than people want. Someone’s like, I want a new website in two months. And I’m like, not gonna happen unless you spend a heck of a ton of money and you won’t be happy with the result. Websites take time, things take time. And so I think it’s understanding the speed at which you want to grow, where you’re at. And then that word metabolize, like, can you actually process what’s happening at the speed at which your business is going? And I think if the answer is no, you probably need to slow down. In our culture, slowing down is seen as failure.
That’s not giving up, that’s just slowing down. There’s a big difference there. And so I’m wondering if you could talk a little bit about what it looks like to slow down and like, maybe, maybe give the listeners permission to be a little bit slower and to be a little bit more intentional.
[00:12:03] Jessica: Well, I think there’s slowing down your activity and slowing down your expectations, and I actually want people in some cases to speed up their activity and slow down their expectations. So, for example, let’s say you’re a life coach of some sort, right? It is totally reasonable to get one new client a month. Okay. Which means that you’re not gonna have a quote unquote, full six figure practice for roughly 12 to 24 months. Because you bring on clients, they eventually leave, you bring on another client. So it takes time to build up that roster. So, okay, we got 24 months. If you’re like, I need to make, I need to fill my program in six months, I’m sorry, that’s like, unless you are bringing an audience of a couple thousand people from somewhere else, it’s not gonna happen.
So I want People to slow down the expectation of what their business can do unless they are selling super high touch, fractional work. And even then, you know, you get two clients, I stay with you for a long time and then they leave. And then you realize you didn’t do any marketing. So like, I want people to think about that. But in order to get those one referral per month, right, that probably means you’re gonna have two to three sales conversations. In order to have two to three sales conversations, you need to be getting in front of 10 to 20, 30 new people every month. So we gotta speed up certain activities, which is being in conversation with human beings, going to networking events, joining communities. You need to publish your work not with the expectation of likes and views, but so that people know who you are. You need to go write and think more frequently than you think in order to have a point of view that someone else is gonna put on their platform. So I think people spend a lot of time over engineering on the results and trying to speed up the results. When you get that first client and then they want to refer you, you’re not gonna get a referral from that client for another six months because they gotta work with you and experience it and then tell somebody.
[00:13:58] Anna: And that takes time.
[00:14:00] Jessica: But I think we are underappreciating the level of activity, real human to human activity and authority building activity required to get that momentum. So we’ve flipped the right where we keep hoping for a silver bullet. And I’m like, the silver bullet’s not coming. But also, many people are not doing some of the fundamental things frequently enough to create momentum. So I want to speed up and like focus on the activity. So like, less about, well, what do I post today? And I’m like, I don’t care. Just post and then go on with your day versus and so speed up the frequency of activity that generates real revenue and slow down your expectation of results.
[00:14:41] Anna: As a, as a marketer, I’m just screaming yes to all of this, right? And I think, and I want to say that this advice, if you’re listening and you’re like, well, I don’t sell services, I sell products. It’s exactly the same advice. You, you can’t just like turn on this magic spigot and all of a sudden you’re going to get thousands of new customers. That happens through diligent, consistent.
Sometimes it’s just going to feel like grunt work, right? And so I kind of want to, I want to switch the conversation just a little bit because I think it’s like the first chapter of your book and I really want to be able to talk about it. So you ask folks to think about what business they’re really running.
And then the first thing he said is most people, when you ask what business do you have? They say, I’m an entrepreneur, I’m a creator, I’m a copywriter, I’m a web designer, I’m a product designer.
And I laughed so hard because that’s how people respond when they’re asked about their business. That’s not a business, it’s a title. And then because of our culture, that title all of a sudden gets conflated with identity, which is way more personal.
So I’m going to throw kind of a curveball at you. But can you talk through the, the differences between identity, job titles and actual business models?
Because I think they get smushed together all too often and it creates a lot of chaos.
[00:16:13] Jessica: The wrong person to talk about the difference between identity and business. Because like I am a business. So I have, I’m like fully like business, business advisor, educator. Like that is what I do. Everything I every, all my hobbies are like, end up being like consumed into my business blob. But I’ll start with the business model and then we can use an example and we can maybe think about that. You know, there’s delivery based and service based business models. And then where you are delivering a service of some sort to person or individual or companies, there is creator based models where you are monetizing your expertise in some way, shape or form. Then there would be what was called the brand model which is where you have done something for long enough where you license people to do it on your behalf. So like Donald Miller’s like Become a story brand certified guide, that would be a, a brand model. And then there’s products which I don’t really talk about, like physical products or SaaS products. So let’s say a copywriter. They start as a copywriter. That would be what I call a Craftsman. Within the delivery model, okay. They are starting to become more busy and then are faced with a choice. They’re like, okay, I no longer wanna do copywriting for 20 hours a week or I wanna make more money. And so the casino’s advice would be scale.
So it’s hire a team of copywriters to do copywriting on your math or hire a team where maybe you’re still doing the copy but someone else is doing the scheduling and stuff like that. You’ve just transitioned from a Craftsman to an agency.
Model within the delivery side or the other scale is have teach everyone how you build it and, you know, build the next copy hackers, right? And that’s the. You’ve now become a teacher that’s on the creator side. These creator business models or delivery based models require a whole lot of different things. And even underneath them, they require different things. So if you are a copywriter and then you bring on a team of copywriters, you become an agency owner, which means your job is not great copy. Your job is setting copy standards. Marketing, sales team management, cash flow management. You may not want to run a team. Now you can say, well, maybe I just hire like a couple people to like help me do some additional projects or, you know, like, I do the copy, but they do the SEO. And then that’s kind of bridges the. It kind of blurs the line. But still, then you’re still managing people.
And then when you decide that you want to like, turn your expertise into a coach, that’s an entirely different business model. It’s a different marketing strategy. It’s a different client. First you were networking with people that could afford to pay you, and now you are talking to other copywriters. It’s a totally different ball game. And so if you like doing copy and you like copywriting for people and you need to make more money, there’s a lot of other ways that we can achieve that goal besides scale.
And I think, like, I’ve seen too many people scale their business and they realize, oh, I don’t actually like running this business. Everyone’s like, oh, this is a job. And I’m like, yeah, it’s a job. Like, I don’t know why we look down on having a job. I’m like, well, I have a job for myself where I show up to work at 10am and I leave at 5, and I get to like, work at a coffee shop over the weekend and I can pay my mortgage and yeah, I have to like, show up for work and I have a job and I’m okay with that. When I was building my business, I had jobs that were like literal jobs.
But, you know, everyone’s like, oh, well, if you can’t step away from your business, you have a job, not a business. I’m like, all right, I’m cool with that. I like having a job. Like, you know, I like actually doing the work for my clients. That’s what I got into business to do.
[00:19:42] Anna: I have never heard the if you the job business breakdown. It’s so interesting because do you do
[00:19:50] Jessica: you spend any time on Instagram because that’s all they’re doing. If you can’t outsource yourself completely from the business, you don’t have a business. You have a job. And your job is to scale until you can, like, outsource it to everybody else. So you can just, like, you know, work four hours a week on the beach. And that’s how you have a business, not a job. And I’m like, all right, cool, I’m just gonna have a job then.
[00:20:10] Anna: Do they realize that, like, a CEO is a job?
Like, that’s still a. That’s still a job. It’s like a position that just. I’m making fun of this, right? I’m not on Instagram at all. It’s a blast. I highly recommend it to everybody. This is making me think of when I quit my, I would say, traditional job in corporate world and started Strange Birds nine years ago. Now eight.
Time is an illusion.
My family and friends especially were like, oh, you’re just free whenever we want you to be free. Now I’m like, this is still a job. I’m still working. I’m still waking up and I’m making coffee and I’m sitting down and I’m doing work. I’m not just, like, hanging out, having a good old time, and every once in a while sending an invoice. Like, this is work. And I think that’s something that the casino wants you to forget, right? It wants you to forget that the casino being the entrepreneurial industrial complex, to use your phrase, which I love. They want you to forget that this is work. This is a job. You must work in order to make things work. But what they’re selling is.
But this is easy.
But if you just did it this way, you could sip mimosas on the beach and be like, what’s that guy? Tim Ferriss, whoever wrote the Four Hour Work Week, you could be like him and, like, basically do nothing and make money while you sleep.
Such a small, small, tiny group of the population does that. And they’re not making money while they sleep. They’re paying other people to make money for them while they sleep. Like, that’s. There’s still a transaction happening.
[00:21:46] Jessica: I want to put one more thing on there. Part of the challenge with the Entrepreneur Casino is who it’s targeting.
So I came in to. And not to be like, there’s female entrepreneurship and male entrepreneurship, but a lot of the messages, like the MLM world of it all is is geared towards, like, a lot. A lot of moms who can’t work a traditional 40 hour week job because in the US obviously we have no social safety net. And like women or you know, the flexible partner is the, the social safety net. And so the messages are targeted at them. This is like you can do it when you are only having a couple hours a week or a couple hours a day because you have other responsibilities. And let me show you how it can be so easy. And what like 1% of MLM participants actually make their money back. So the industry is like, it’s targeting the most vulnerable populations with this type of advice.
And that’s what makes it even worse is because a lot of individuals who, who really don’t have a lot of time and money buy into the promises of quick and easy wealth without understanding. No, no, the people that have done this either gotten super early or spent a ton of money and time to build up the network of people that they can get this army for, you know, the MLM army, as it were.
And again, like that’s what makes this all so hard is the population that needs to have flexible working arrangements and make the money that they need to make are being sold a dream of how easy it possibly is. And it can build a business with not full time hours. But I think we can’t expect full time income without full time hours in a six week accelerator program. Like, okay, in three or four years, sure.
But no one wants to buy that. No one’s going to buy a six week program that says, let me teach you how to make, you know, $5,000 a month in 20 hours a week, in four years. No one wants to buy that program. Even though that’s the reality of a lot of the timelines. If this is something that you’re doing in the margins of your life, and
[00:23:55] Anna: that’s not a bad thing.
[00:23:56] Jessica: It’s just, I think we, it’s. The expectations are set really awfully.
[00:24:01] Anna: Yeah, I, this kind of dovetails into. I really want to talk to you about enoughness.
We are the United States. Culture is grow, grow, grow. Nothing is ever enough. The more money you make, the more value you add to society overall, the better you are as a human. Like there’s like personal value attributed to the wealth that you can accrue and this question of enough. Right. So I said earlier, like, I’ve always been obsessed with budgets and I always like, know what my breakdown is of like what do I actually need to make in order, like the baseline. I have to make this in order to pay my mortgage, buy groceries and not be Stressed I need to make this much money in order to do all that and have some fun. And then I need to make this much money in order to do that, have some fun, go on vacation and save for retirement. Right. And running those numbers and I can’t tell you how many times I have talked to like newer copywriters. This is back when I identified more as a, as a copywriter, as a job title. No one wanted to run the numbers because it is a really, really scary thing to look the numbers in the face and say, this is what I need.
But when you run the numbers you’re like, okay, I actually have a goal rooted in reality that isn’t just I want to make a million dollars, which then you’re always going to feel like not enough. I’m just, I’m going on a soapbox now. But I. How do you think about this idea of enoughness when it comes to being an entrepreneur running a business?
[00:25:36] Jessica: So in the book I called it the zone of enoughness because there’s four dimensions that I outlined. There was enough money, time, schedule flexibility and creative autonomy. And so there is a min and max for all those. And you’re someone’s like, max money. And I’m like, we’ll get to that. So there’s a minimum and maximum on all those dimensions. I do think that it’s important to say minimum. What’s the minimum amount of money you need to run? Right. By the way, a good target is you will need to make 1.5 to 2x the amount you need to take home as your top line revenue. And you will need to do it in roughly 50 to 60% of the working hours you have available.
So because if you, unless you are running like a couple of like long term retainers that are basically like part time jobs, you’re going to need to spend a bunch of your time marketing, handling business admin, building business systems, building your ip, you know, building infrastructure. And then you’re going to have to like, you know, deliver for, you know, 50 to 60% of your time. So that’s kind of the, you know, unless you, if you’re like, I don’t really want to do that, I just want to like do my copywriting. I’m like, cool, that’s, that’s probably then be a contractor for an agency. Entrepreneurship means that you only get to spend 60% of the time you do want to do the things and then the other 40% is actually managing your business.
I had my best revenue month ever in late 2024. And the amount of work I had to do the following month because I sold it in was crushing. It was crushing. So, yeah, I had enough money. I had more than enough money.
I didn’t have enough time.
And when I looked at the types of projects that I was doing, I’m like, yeah, these pay the bills. Which is like the first journey in my zone of enoughness was like, just make money to pay bills.
Then it was like, cool, make more money to pay for business investments. And then it was like, oh, too much money, not the right fit clients, too much time.
I have to do something different.
So then I am in a different spade of my zone of enoughness now. But I think there was minimums and maximums, right? I hit my maximum with 50 hour work weeks for like an entire summer and it was pretty awful. But now my business is in a bit of.
[00:27:47] Anna: I know, but now my business, my, my facial reaction to the 50 hours a week during the summer was like pure horror.
[00:27:57] Jessica: Yeah. But if I’m working in my business less than 20 hours a week, I’m sad because that means I’m not engaging with my clients. It’s not, I’m not engaging in creative projects. Like, this is what I like to do. Like, like some people are like 20 hours. That sounds like my, my maximum. Like, awesome. Cool. I don’t have kids, right. Like, my husband works. So if I’m not working at my craft, what am I doing with my day? Watching tv? I don’t even know. My dimension of like enoughness being triggered has never been around money. The dimension that always has pushed me enough is time. If I let it work, would consume my entire life. So now that my business is a bit more stable, I, I could recognize that I could make more money if I sold, sold more things, but I don’t want to. I could make more money if I changed my prices, but that would change who I work with or stretch other people’s budgets. And I don’t want to do that. Or I could, I could sell more stuff. I could do more stuff. But I’m like, I, I’m not in that season. I’m not there. I’m like, I just want to like, you know, watch Bridgerton or Heated Rivalry and read a book and kind of putter around the house in the morning a little bit. I just finished up a program and I’m like, now I don’t have to sit down at work quite so early and everything just takes like a little bit longer. Everything’s a little bit slower. And I’m going to make less money top line this year than I did last year. You know, I’m going to do that. I’m going to take home more. Tell you that because I’m not spending.
I had last year, I did a rebrand, an entire new website, all with new copy. Finished my book, paid to publish my book, published my book, launched a program, redid the entire curriculum of my cohort program. And now those things are done. And I’m like, cool, I’m gonna like, chill for a minute. And I wrote a post on LinkedIn. I’m like, I don’t want to charge you more money. I don’t want to sell you more things. I don’t want to like, send more emails. Like, my goal is not more profit. My goal is cover my bills, do the work I love to do with the clients I love to do it with, and then go enjoy the rest of my life.
[00:30:01] Anna: So something that I really want to highlight in what you said and say it in a slightly different way. So, like, people really grock it is when we work with clients and they’re like, we want to sell more products or we want to raise our price or we want to add this new offer into our mix.
It’s so easy to say that, but it’s so easy also to not understand the ripple effect of what that seemingly small change could have. Something that you said of like, I could raise my prices, but then I’d be working with different clientele, right? And so, sure, you want to raise your prices because that would help your money goal. But then you have to do all of this different type of marketing because you’re now at like a quote unquote different level or different tier of clients or different tier of customers that you’re trying to get. You want to add an offer. Does your current customer list care about that offer? No, you got to go build a new customer list, right? And so it’s, it’s all of these things.
I don’t want people to hear that and go, well, I will change nothing. And with a feeling fear of not ever adjusting or growing or shifting or changing. It’s just going into those adjustments with eyes wide open and thinking about what you call, like the zone of enoughness. Right? If I change this thing, it’s going to change my zone in this way. Is that what I want? If the answer is yes, go ahead and try it, see what happens. It’s something that I see a lot that stops a lot of people is fear of failing. So they just don’t Even try or trying so hard they don’t actually launch it because it has to be perfect.
Just try something out, give it a go, give it a good honest college try.
And yeah, really think about like what feels enough.
I think we’re a consistently under satisfied population, which is just silly. I’m speaking from a very privileged space of a, a white middle class person in the United States, right, who has like a solid job and income.
There’s a lot at my disposal. There’s, there’s a lot of enoughness going around if you just take a look
[00:32:03] Jessica: at it to go back to something we were talking about earlier in the episode. If you’re raising your prices and it’s going to put you in another population, think about again, like the speed at which you’re going to make those connections and the speed of which if you’re like, cool, I need to raise my prices. You know what I’m going to do? I’m going to spend the next year building that new network and I’m going to spend the next year tightening my backend systems so that it’s a experience that matches that price point. I’m going to shore up my templates, I’m going to shore up my referral partners while getting even better and more efficient. How can I be more targeted and potent with the clients? I have the price point I want, so I’m kind of making that effectively hourly rate that I need to.
And then raise your prices. And again, that’s like, well, people are like, well, I need to do it now. I’m like, cool.
[00:32:50] Anna: All right.
[00:32:51] Jessica: Like there’s the, I don’t know if you read the book 10x is easier than 2x, the Dan Sullivan, Benjamin Hardy book. But you know, there, the, the, the, the concept of focus on the most important thing is a fine concept. Like, you know, like 20% of the work gets you most of the results. So focus on that 20%. But the story that the guy used is like, okay, well you know, this guy wanted to 10x his prices and so he got a bunch of no’s and then he got his first yes. And it’s like, oh, I could do it now. And I’m like, cool. I don’t have the Runway for, you know, six months of no’s.
So you know what I’m going to do? I’m going to not crater my existing business and I’m going to build the scaffolding which requires people to think in multiscale horizons and it requires us to again, unhook from people Telling you it’s going to just be easier to raise your rates. I’m like, no, it, it can be if you have the right client base, do you have the right network? And if you don’t, don’t take the easy way out because I guarantee you, I’ve seen it over and over again, you’re going to crush your business because you didn’t say, what are all the knock on effects and trade offs of this? And thinking in longer term horizons to say like, all right, I’m going to do everything I need to do so that by the time I’m ready to double my prices, you have a networking client base that is like, yes, this is a reasonable amount to pay for this. Without manipulative marketing. That’s not going to happen in an eight week accelerator, three month mastermind to like fill out your group program or double your prices and then it’s not going to come. And honestly, this is what drives me.
Sure, money mindset might be a thing, but what if it’s not your money mindset and it’s really your market? What if it’s not about your, your confidence in your skillset and it’s about you. You are working with early stage entrepreneurs who this is really not affordable. And if you want to charge these rates, you got to go, you got to go to B2B, you got to go to corporate, you got to go up market.
Is that a money mindset and confidence problem?
Maybe, but it’s probably your market.
[00:34:50] Anna: Yes, thank you for saying that. Yeah, absolutely. Actually identify the problem that’s in front of you when it comes to prices. That was always the advice that was given to me. Well, just like raise your prices, you’re really good at what you do. Ana just raise your prices. And I’m like, but I like the type of clients that I work with now. If I raise my prices, I don’t get to work with them anymore. I really like the clients that I work with now. They can afford me. I am on the higher end of affordability for them. But also the prices that I have with them allows me to be really generous in how I work with them. And that’s important. Right. So it’s thinking about the money you need to make, how you like to work.
Does that price point allow you to work in the way that you like to work within your zone of enoughness, et cetera, et cetera, et cetera. And I think that it’s scary to think in those levels of complexity because it’s a lot easier again, to the Casino is like, this is easy. Just pull this lever, you’re good, you’re good to go. Go run off into the sunset with big bags of gold.
But business is complex. Being a business owner is complex. Having a job is complex. Even if you’re in a company, your job is complex. Run your own company, your job is even more complex. And you just gotta face that complexity. This has been an amazing conversation. I have really enjoyed it. I feel like I could talk to you offline about business models and practices and budgeting and forecasting and levels of growth, et cetera, et cetera for eons. Is there any last minute thoughts that you would love to share with the audience?
[00:36:27] Jessica: This is a incredibly lonely journey. If you’re sitting in your, on your sofa, scrolling Instagram or Twitter, LinkedIn and like, being like surrounded by all these people, like showing you their, you know, polished highlight reel, one, it’s marketing. Two, it’s not real. And three, the way you get out of the casino is by surrounding yourselves with other people doing similar work in a similar fashion. So you.
Do you have to join the super expensive Mastermind? No.
Do you need to surround yourself with people who are walking the journey with you and maybe stumbled in from a different part of the casino and have different experiences and different worldviews, but also different skills than you? 100%. And I think in order to make the math work, too many of them have been built up with such scale where it’s not actually personal. Personal support in a lot of memberships is like, no, no. This is just the entry point. To get real support, you gotta upgrade to the higher ticket offer.
Find places and find people that you can talk to a real human and get real human support. Witnessing accountability.
Not to like plug my stuff, but I have a membership that’s like $30 a month us and if you ask an answer, you know what I will do, I will answer it because I’m like, you shouldn’t be spending more money than this. In some cases, I don’t want you to be spending more money. I have hit my business model so that I can afford to do this with you.
Awesome. Yay. And. But there are spaces like that where people are building more intentionally. There are spaces and places and people that are rejecting this casino dopamine environment. They are there.
Please find the others.
[00:38:10] Anna: Yeah. And just also want to say, if you, if y’ all are listening to this and you’re like, wow, I want to hear more. If you didn’t listen to our interview with Tarzan K, I highly recommend y’ all go listen to that.
So Jessica, is there any place that you would like to send people to learn more about you?
[00:38:27] Jessica: If you want to learn more about me, you can go to my website, deeperfoundations.com and if you’re intrigued by the book leaving the casino, you can buy that on my site or you can buy it on Amazon.
Flying the Coop is brought to you by Strange Birds, a strategy to execution Co op for organizations doing complex, meaningful work.
When the opportunity is obvious but execution feels impossible, we turn big ideas into real progress.
Find us at Strangebirds Land.