From $250K to $10M: What Breaks First When You Scale with Jeni B

Jeni: [00:00:00] everybody's brain goes immediately to, SOPs, standard operating procedures. But actually SOPs are the tiniest little, piece of systems, and if you start with SOPs, you end up with a Google Drive junk drawer full of stuff that nobody ever looks at because it's not helpful.
Intro: You're listening to the Seven Figure Leap podcast. We're here to leverage rich relationships and smart strategies to take your business to the next level. Here's your host, Dustin Riechmann.
Dustin: How do you actually scale your creator business to a million dollars and beyond without losing your mind? That's gonna be the central question that we unpack today, and rather than hear more of my own journey, although I'm sure we'll have some of that, as part of the conversation, I'm really honored today to have a friend, [00:01:00] Jenny B.
Dustin: Lee, who's an... or Jenny B, who's an expert at this very topic. And, Jenny, please introduce yourself to the audience, provide a little context for how you've, grown to learn so much about this journey of scaling for solopreneur businesses.
Jeni: Absolutely. Thanks so much for having me on, Dustin. I appreciate it.
Jeni: So I'm Jenny B. I have been in online business specifically for, how old's my son? 19 and a half years now. Yeah. I've got a slew of degrees that I picked up over the years, mostly from not wanting to get into the workforce during the dot-com bust. it was rough back then.
Jeni: so stayed in school for a while, but fast-forward to 2007, and I had a baby, and just like for many people, it changed absolutely everything. Turned my world on its head. And I've been a person with lots of ambition. I love solving problems. my background was actually in linguistics, which is, the systems and science of language.
Jeni: had spent a lot of time going back and [00:02:00] forth to West Africa to do my, what was then doctoral research. But I held this baby in my arms, and I just was... I lost my breath. I looked at his sweet little face, and I had this moment of, "Oh, God. I'm not going back to work." I'm not, and I'm gonna figure out whatever it takes because I do not want to be away from this human being for a moment that I don't have to be.
Jeni: my, my service business life kind of started in a way to fund my mothering habit. you know- ... as an instead
Jeni: got, got- That's a very healthy habit to fund, I'll admit It
Jeni: is. we've, we all got bills to pay. And aside from a regular salary, which would've been very nice to hold onto, I realized that if there was any time in my life that, to be scrappy and just apply like the figure it out, like anything is possible, we can figure this out.
Jeni: I was in my mid-20s, and just full of energy, inspired by this new [00:03:00] baby. so I, I t- I kind of took a survey of the skills that I had at that time, and I grew up in early... The internet really came online with the Netscape browser when I was in high school, and we had a computer lab. and I spent a lot of time in high school just messing around building GeoCities websites.
Jeni: So teaching myself HTML and was CSS part of that? I don't think they even let you. They were just like, "This is, we have ugly lime green, we have ugly cobalt blue." Like you had limited choices back then. but I had also developed a fascination of, what it was to be a business that had a website.
Jeni: and so I, I was messing around with like early black hat SEO techniques and, oh my gosh, this is, this so dates me, but we would literally do keyword stuffing. At the bottom of a webpage, you would scroll all the way down and the background of the page is white, and we would just write, "Dentist, Dalton, Georgia.
Jeni: Dentist, Dalton, Georgia. Great [00:04:00] dentist, Dalton, Georgia." And it would be white text on a white background 'cause we were writing for the bots. so super shady business.
Dustin: And how far we've come with, AI and, it's what's new is, or what's, old is new again in some ways. there's always a new tactic.
Dustin: There's always a new trick. yeah. So yeah. I, I, what's funny about that story is it brings me right back to the beginnings of my online journey and, and it just sort of teleports me back and then I think in sort of a flash forward moment of it's again, like everything's changed, but a lot of things really fundamentally haven't changed because ultimately it's business and you're trying to stand out in a noisy world.
Dustin: And yeah, I'd love to hear more about, present day Jenny B and, and like how your, how you've acquired this experience to know so much about scaling businesses. I'm sure you've scaled your own, but you also served a lot of other entrepreneurs as well, right?
Jeni: I did. I s- I scaled and sold one in 2019.
Jeni: I... The way that I came up in, in business is very [00:05:00] organic, and it was literally me being insatiably curious, looking at the next problem that my clients had and saying, "What's a better way to do that than what they're doing right now?" and so it was this very organic evolution where every single stage of my career exposed me to another layer of how businesses actually function.
Jeni: So, SEO taught me discoverability, demand. when I was building websites a couple years later, I learned about user experience and buyer flow, and then I was in copywriting for a bit, and psychology, messaging, funnels, product development. Like, all of these different layers that I added over, You're gonna get from this story that I have a very short attention span, and I-- that's not incorrect. that's 100% true. I
Jeni: think many of us can, relate to that, so...
Jeni: Yeah. But it's just this idea that every... I was going deeper with every single layer in a business that I went through, and so that I've,fast-forward to today, I have [00:06:00] been in literally every seat of a business.
Jeni: I even dabble in a lot of, CFO-type functions a lot of times with my clients. And so having come up supporting businesses as a contractor, being a coach, being an advisor, being a strategist, through all the different functions of a company, I really have developed a perspective for the holistic ecosystem that is a business, and so that when, if you change one thing, it does have a ripple effect out to other parts, to other parts of the business.
Jeni: So that's gotten me to where I am today, kind of the, the 30,000-foot view that has come from a lot of experimentation, learning, iteration. and I've seen gurus come, I've seen gurus go. I ... and I've seen the pendulum swing so far in one direction, from, the early days of vlogging where it was like, "Online community is so rad," to, ev- to,[00:07:00] purchase media and ads and, now we're kind of swinging back the other direction where it's so much more about relationships, and that's really what I love about your work, Dustin.
Jeni: but the... See, being able to s- to see the pendulum swing over two decades now, it keeps me feeling excited about solving the problems that are happening right now and being able to anticipate also what's coming next down the road.
Dustin: so there's like knowledge, but then like applied knowledge becomes wisdom, right?
Dustin: And I used to, in earlier my engineering career, it was like all I wanted to do is shortcut the line. I'm like, "I'm smart. I can figure this out," right? But you just can't replace experience. And so, you brought up relationships, which is great because Jenny and I actually met through Rich Relationships Club with, Selena Soo, and we had a get-to-know-you call.
Dustin: And by the end of the call, I'm like, "I gotta have you on the podcast because I already know you can offer such a unique perspective, not only in your own lived experience in doing this for 19 and a half, years and counting and sitting in all the seats, but you have a really unique [00:08:00] perspective in sitting alongside entrepreneurs in different stages of growth."
Dustin: And, as we zoom into kinda one of those key transition points, this podcast is called The 7 Figure Leap, right? And so a lot of our listeners are on that journey. They are solopreneurs. They're experts. They're-- they deeply care. They're on a mission to help the world with this unique ability and gift they've been given.
Dustin: And the business part is often feels like an obstacle, I think. and I can speak from personal experience. A couple years ago, I would look at that seven-figure threshold and think, "Well, when I get there, all my problems will go away," right? Like when I get... that is the pinnacle, and, once I hit that finish line, then I feel like, I've made it and I've accomplished it.
Dustin: And there is some truth to that. that's a huge milestone, and I'm super grateful to have done that. I've had numerous episodes on this podcast talking about a lot of those struggles, hiccups, unforeseen things around the corner that come in that s- in that, particularly in that journey from six to seven figures.
Dustin: So that's really why I [00:09:00] hope to zoom in today, Jenny, and learn from your experience and your wisdom so that people can see what's coming in that or, some people might be sitting kinda on that seven-figure, pinnacle and looking down the other side or looking back and saying, "Oh my gosh, what has happened?"
Dustin: And I know I felt like the dog who caught the car, that, that proverbial moment of "I got what I wanted, and now what?" Exactly. Or, "Wow, this could've been way easier if I had some guidance along the route because it was a pretty, pretty painful experience." So yeah, so let's dive into that.
Dustin: We got a few kinda key areas I'd love to get your wisdom on. So one is speaking to someone who's in that seat, not as a discouragement at all that like I think that's a great aspiration is a seven-figure business. But maybe let's unpack like why hitting that first seven figures, doesn't actually fix the overwhelm that maybe people feel when they're sitting in, the six-figure or even multiple six-figure seat.
Jeni: Yeah. [00:10:00] So, an interesting thing, you said the dog who catches the car and then now what. First of all, we're obsessed with numbers with lots of zeros in them. We love them. we love a zero- Without decimals in front of it. so the thing that nobody tells you though is that the way that you feel on the journey is the way you will feel when you arrive at the destination.
Jeni: And so you are tuning your-- You are literally tuning your nervous system every day you show up to work, every week, every month, every quarter, every single day that you make choices in your business and you take action or don't take action, or simplify things, or make things more complicated. You're making individual choices that, however you feel, let's say you're currently at two hundred and fifty thousand and you're going for the next five hundred thousand right now.
Jeni: Well, if you don't fundamentally change how you show up and the type of energy you're [00:11:00] bringing to your business, then you will feel at five hundred exactly like you feel at two fifty. You will feel at a million exactly like you feel at seven fifty. and part of it is because of how our nervous systems,exist.
Jeni: Thank you, evolutionary biology. the person that you are fundamentally doesn't change just because you hit a milestone with seven figures. So the,the thing-- Oddly, the thing that makes entrepreneurs so incredibly effective at running, at starting a business, at getting that first six figures, at growing to seven figures, is the thing that actually s- becomes their ceiling at seven figures.
Jeni: So, we get into this because we have lots and lots of interests, and we're multi-passionate most of the time. And, we don't have the ability to focus, but that's fine because there's so much of early-stage business that is about experimentation and bringing a spirit of playfulness and "I can figure it out," and all that kind of thing.
Jeni: If you [00:12:00] hold on to that at seven figures, though, what you end up doing is stacking str- one strategy on top of another s- another strategy on top of a tactic. When I go into businesses and I look under the hood for the first time, Dustin, it is... I feel like an archeologist. Like I can go into somebody's CRM, and I can be like, "Oh, I see evidence of this type of video sales letter funnel.
Jeni: Oh, I see what they were doing over here." And I can literally reconstruct everything they've done in their business by what it looks like today. Because most of the time, founders will add, everything is additive. Let's try this, let's try this. Or they will-- they'll start a project, never finish it.
Jeni: But guess what? The remains of that project are still hanging out, still clogging up our ability to make great decisions, without actually leaning out, making conscious decisions, and deciding, "What am I gonna cut?" Out. [00:13:00] What am I gonna hold on to? What am I gonna change and adapt, and what am I going to keep as is 'cause it's already awesome?
Jeni: So part of-- like my work is, informed so much by lean principles, which came from manufacturing. but as applied to service businesses specifically and entrepreneurialism, i-info entrepreneurs, it looks a little bit different, but the principles are the same, which is let us find the straightest line between two points, and let's let everything else fall away.
Jeni: And it's that piece of the letting go, which we're not great at. In twenty twenty-six, we're not awesome at letting go of stuff. I don't know about you, but, I, I know so many-- I am a digital hoarder. I have a Dropbox that is full of fifteen years' worth of online courses, and I used to record my screen so I wouldn't miss anything.
Jeni: And then... You know what I mean? So it's this ability to identify what works and then say, "What [00:14:00] do-- what does my team need to be able to do? What do they need to know? What do they need to be able to evaluate to carry this on in my stead?" Once you've leaned out exactly what you're doing there. Oh, man. So much- So this- So good
Jeni: yeah,
Jeni: the team there, I just, it's tangentially- Yeah, you just, threw in this little
Jeni: word that, It's
Jeni: oh, yeah, by the way, you have a team at a million." No big deal. yeah, let's,
Dustin: let's set the team over here- ... 'cause I think that's what we should talk about next is, like- Okay, great
Dustin: how does that work, right? but yeah, I think when I reflect back on what you said, I'm, of course, I can't help but think of my own, journey in a couple different businesses that went to seven figures. I think the energy that you bring as a founder and in this, scrappy mode of, just push, push, push, energy in.
Dustin: And like you said, you keep trying new things, and they keep adding up, and a lot of them are incomplete. And I know for me mentally what can happen in that is, it creates these open loops, some of which I'm conscious of, some of which are kind of buried in there in the subconscious. And [00:15:00] I love what you said about, your CRM or your, website or email marketing, whatever.
Dustin: You have these sort of archives of energy and projects and things you've built over time, and I think huge gap that we encounter, which is, where you started to go there, in talking about lean principles, is we often don't take the breath and sort of be able to look back objectively and be like, "It's good that I experimented, and I built many partial bridges and a few complete bridges, and I've made great progress."
Dustin: But at some point, you have to step back and be able to objectively evaluate and decide, and, like decide means to cut off. you have to actually cut out much of that, probably most of that, right? And I think that's a big principle here is like- You get six figures through hustle and pushing and adding and trying and experimenting, but when you want to get to seven without losing your mind and just having a 10X, version of the bad stuff, you have to make objective decisions and adopt these lean principles.
Dustin: [00:16:00] So finding the straightest line from where you currently are to where you want to go without maybe having that, a disordered attachment to things that you've done in the past, right? Like objectively saying, "Well, I am here now. This is where I want to go. What's the straightest line? I have to let go of some things," because you actually have to do less to get to seven figures than you did to get to six figures or multiple six figures.
Dustin: And then, and then your-- of course, your identity has to shift in that too, because you're no longer a scrappy solopreneur, and we're gonna get to team. anything in there that you wanna like double tap on or deny or confirm about what I just shared sort of as a summary of how people get to the point many people are listening to us at?
Jeni: Yeah. I-- Well, to add on, these are not problems that solve themself. Like complexity, any complexity that exists within your business will scale. So if it's really noisy, if you go into Slack and it feels like the Wild West, and there's gonna be like a shootout on Main Street because the every-- the messages are rolling in and you have to make [00:17:00] 800 different decisions in the next 15 minutes before you go and serve your next client, that, unless you like draw a line in the sand and we say, "We do not go forward beyond this until we solve this communications problem, this decision-making problem, who's responsible for what," then at 10X, it is 10 times noisier.
Jeni: It's 10 times wilder. So I was talking the other day to, the actually the chief of staff of a $10 million company, and this is a company that has not, They didn't deal with all of these things at one million. They're dealing with them at 10 million. But at 10 million, it looks even uglier. At 10 million, it looks like, like our organization is a revolving door.
Jeni: We hire people, we cannot hold onto them because they don't have, they don't have the patience or time, highly qualified people, to sit around and wait to have the tools and resources that they need easily and [00:18:00] simply for them to be able to shine. so we've, money does not buy efficiency.
Jeni: And-
Dustin: It's a writer downer. I'm writing that down. So money does not buy efficiency, and we always like to say like simplicity scales, complexity kills. That's true, but also complexity will scale if you let it, right? But it just scales into more complexity, and it becomes an exponential Tangled web of craziness, right?
Jeni: Yeah. And what I see for founders that are not dealing with this on their own, there is... Like I said, there, there's a nervous system component to it, and, Dustin, you touched on this with your identity. as the crucial identity work. shout out to Cassie Shea, who is now a mutual friend.
Dustin: Yeah, and she's been on the show a couple times talking through my iterations and my evolutions through some of these identity ceilings, and what that particularly was what was required and, practically what we did with the identity work, to push through that.
Dustin: So [00:19:00] if you're feeling tension as you listen to this, definitely go check out, the episode with, with Cassie, who's a mutual friend of Jenny and I, so.
Jeni: Yeah. So if you have a founder, what I see in founders that will, they'll scale to a million, they'll unknowingly, because they're, like, they don't know how to handle that feeling of chaos.
Jeni: They're like, "I've done all this. I've-- Surely I have earned some rest at this point." But they're, like, flirting with burnout. They're working. They have a team, and they're working harder than they have ever worked. But now it's because it's dysfunctional, they're spending all their time managing a team when they got into it because they love to do the work.
Jeni: They wanted freedom, right?
Jeni: And so they wanted freedom. And so we inadvertently... And so many entrepreneurs come into this, from corporate of "I don't want that," but then they recreate corporate inside of their own organizations. So if they don't deal with it, then what happens is they will be like, "Oh, well, I'm tired of this business," and they'll go [00:20:00] start another one.
Jeni: "And I'm tired of this business," and they start another one. and become serial entrepreneurs, which n- I am not knocking any of that. I love the ambitious and, the ambition and tenacity and, nothing ultimately is ever wasted because it's wisdom and it's experience. But it's the point where it becomes at odds with the goals that they have that they, they leave feeling incredibly unfulfilled.
Jeni: So I-- a primary,kind of litmus test for am I building the kind of business I wanna build is how do I feel? As we were saying at the beginning, do I f- do I love this on a day-to-day basis? Because you could be loving it, and if it's kind of like pain is a signal that there's something wrong in the body, this feeling of mild dissatisfaction, stress, overload, it's actually a signal that something is wrong.
Jeni: And just because it's something most entrepreneurs deal with, especially scaling to seven figures, it's [00:21:00] not something they have to. But they keep pushing because everybody talks about how hard it is. Yeah.
Dustin: And that's the only tool they've ever had, right? and I think a lot of people, and I've been in this camp too, you sort of- adopt this fatalist identity of "Well, I guess I'm just the type of person who starts new things, and I'm good at starting things, but I'm just not good at, completing them," or, "I'm just so creative, I get bored easily."
Dustin: Which to me, speaking to myself like that, I realized was a cop-out, and that the skills and the resources and the experts like Jenny are there to help you get to that next level, right? But you have to make a conscious decision to, realize you need the help and pursue the help, invest in the help. And like that, I think is, someone...
Dustin: Hopefully this is the wake-up call for some people listening, right? either your health or your relationships or hopefully someone in your peer network or a client or a team member, someone's gonna hit you upside the head with a wake-up call, right? That's gonna tell you this is no longer [00:22:00] sustainable, and then you're gonna have to make that decision out of a place of relieving pain.
Dustin: Much better, if you can do it, is to get ahead of that and anticipate "This is part of the journey, and I need to make conscious decisions now to,kinda head that off and get ahead of it." So I think we've, probably painted a very emotionally, connecting, reality for a lot of people listening who have experienced this.
Dustin: So I'd love to shift a little bit now, Jenny, into so what do you do about it? maybe we can talk about team or we can talk about, systems or s- I know there's a lot of elements here obviously that we're not gonna be able to get into in tons of detail. hopefully people will reach out to you and get more specific help.
Dustin: But, kind of at a high level, what are the levers we can pull to be able to get to seven figures and beyond and have joy and fulfillment and peace in that? and maybe since we opened the loop on team, maybe we should start there. Like how do you do team withou- without screwing it up and without making it like feel like you're back in the corporate world that you tried to escape?
Jeni: Yeah. So to, to back up [00:23:00] to a little bit higher level, team is absolutely an essential part of scaling a business, but it's one of five essential parts. So like it,it's usually the thing where-- In, in fact,I sold my first business because specifically I had a team. Ironically, right?
Jeni: I had a team, and I no longer wanted a team. I was like, at that point, I had four kids 12 and under. I was a single mom. I was like, "I don't wanna be... I don't want to boss anybody like-" I want a job. And so I got a job for a couple years, and it was great. But, but so we've got, in the lean scaling system that I use, we have the strategy, which is what fundamentally is can you predictably get results for people in a way that is leveraged?
Jeni: So you've got a, you've got a way to get repeatable results for people, so they will, obviously go off and tell other people about you. You get a great [00:24:00] reputation. you have a lot of buyer confidence in the services that you provide or the courses that you have or whatever you're selling.
Jeni: but so if the strategy, if the business model itself is not scalable, it is going to create a huge logjam in every other part. I see you nodding your head. You're like, "Yep." I see that
Dustin: a lot. I mean, I've also experienced that. but this is something I see a lot, where someone, they get to six figures, they've got this very bespoke one-on-one model, and they're like, "I wanna have a seven-figure business."
Dustin: I'm like, "I think you should, and this model can, literally cannot get you there." you can do the math, that you need 10 times as much money coming in. How can you ever deliver 10 times as much value in the current model, right? And that doesn't mean that's, a death sentence to the thing they're doing.
Dustin: It just means it requires a different model, right? it requires a different strategy, and I love that you started with this one, and you define strategy in the lean, system that, that you use with clients as [00:25:00] predictably deliver results that are leveraged. So we're talking about build and fulfill the promise to our clients and add value in a way that actually can scale, which I think a lot of people sort of jump over and they forget that's the core part of business.
Jeni: Yeah. And a simple test for this,and it really applies to all five of the areas. So let me just give you the high level, because I've got people that are gonna be-
Jeni: Yeah, let's go all five, and then we can zoom in on a few.
Jeni: Yeah. Yeah. if we don't start with the high level, we're gonna lose people in the weeds.
Jeni: so strategy planning. Do you have the ability to connect the plans that you have, y- the vision that you want with specific plans, and do you have the ability to connect those plans with day-to-day execution? What should you and every person, every bot, every agent who is working for you, what should they be doing on a day-to-day basis to be able to carry out those strategic plans which are ultimately tied to your vision?
Jeni: So [00:26:00] if you're missing that way to connect the vision with what you're doing on a day-to-day basis, this is where I have founders being like, "What are they doing all day? I have no idea. I have a team of seven people and, I feel like I'm paying them too much. I don't know what they should..." and it's because we're not organized around a central Strategic plan where everybody knows what they own, everybody knows what steps they take.
Jeni: We've got regular cadences of getting people unblocked. "Hey, team member A, what do you need to be able to get to that next milestone in our project," right? To be resourced. But if you don't have a strategic plan in place, you cannot do that, and if you're not actually working the plan.
Dustin: Yeah. You have a plan, and then you don't use it or you don't abide by it yourself, and, obviously that gives you leadership in a whole nother aspect.
Jeni: Procrastaplanning will not get you there. we're just like, "Ooh, if I... Just a better plan." But we have to work the plan. So strategy planning systems, and this is where everybody's brain [00:27:00] goes immediately to, SOPs, standard operating procedures. But actually SOPs are the tiniest little, piece of systems, and if you start with SOPs, you end up with a Google Drive junk drawer full of stuff that nobody ever looks at because it's not helpful.
Jeni: and so if I'm coming in, if I identify that a company has s- a systems problem, I'm looking at, okay, what is the flow to... let's take a client onboarding for example. And I'll say, if I just started with the SOPs of, how do I welcome somebody, how do I make sure they have access to Kajabi? How do I do...
Jeni: all of the little how-tos, I'm missing some big opportunities. Seth Godin said, and this is in a more recent, one of his talks, he said that a l- that what gets in the way of scaling is that people, founders spend their time optimizing things that should not exist.
Dustin: I've heard Elon Musk use that quote as well at a very high level where that's like his main thing when he [00:28:00] walks into a SpaceX facility or whatever.
Dustin: He's like, "Before we s- continue to optimize, let's first decide what shouldn't exist, because we spend most of our time optimizing things that actually shouldn't even exist." Which yeah, I didn't... that makes total sense that Seth Godin would, would say something along those lines. It is so true.
Jeni: Yep.
Jeni: What... Pull this over here. Yeah. So with the, when I'm looking at,a company that has high-level systems, first I'm gonna sit down, and I'm not gonna start digging through their Google Drive. I'm gonna say, "Show me where I can see the customer journey." From the time a person hears about you, they discover you on, the Seven Figure Leap podcast They are evaluating you against other people.
Jeni: They are identifying themselves in the problem that they have, the solution they want. They sign on with you. There's the receiving the service, they're getting success, they're becoming ambassadors. I wanna know how that happens. A lot of times, like it-- when I'm mapping out a full customer journey with [00:29:00] psychographics of how, like exactly where they're at, what do they need to know?
Jeni: what do they believe that they need bridges for, right? if I could cut out 35 SOPs if I identify that, "Hey, we didn't even need to do that," in the first place. So systems, we did strategy and planning and systems team, and then we're building a team around what it takes to deliver the results that we are promising that the clients want and are willing to invest in.
Jeni: And, there's so much stuff that you could do, like in any given day. and this is actually a problem I see with, founders getting super distracted by AI, is because they're like, "I'm geeking out. This is so cool. I live in the future. Look at me." And they're doing all this stuff, and it's activity that's not actually moving the needle.
Dustin: Yes. Amen. I, I feel like that is like a huge trend as we sit here today. I'm in, different communities and [00:30:00] discussion areas, and I watch these individuals who, they're pursuing AI knowledge for efficiency, and then they are now-- and they'll tell you, "I'm now working twice as many hours as I've ever worked in my life.
Dustin: my business is faltering, but I know a lot of cool stuff about AI, and I created this really neat, video about a, a gopher on a dock somewhere." And it's Yeah. So I think that it's like the new way to distract ourselves from what actually matters. And of course, AI has its applications, but I would argue that, the founder shouldn't be focused on mastering these new tools.
Dustin: that's a great place to invest in people who Can take that and apply it to your, let's see, strategy planning systems team, in a way that actually moves your business forward. And then if you wanna geek out on AI, that's cool, but that's more of a hobby. It's not like the thing you should be spending your time on as a CEO.
Jeni: Yeah. And ideally, your, your-- the people that you are hiring on your team are going to be strategic implementers. [00:31:00] they are themselves going to be taking the mantle. in the year of our Lord, 2026, would I hire anybody with an aversion to AI? I would not. I need people... I'm gonna be looking specifically for people who are adaptable, who are,are looking for quicker, more efficient ways to be able to achieve the same output.
Jeni: And so I can just hire people on my team that are already doing that hobbyist work of, taking apart custom GPTs or building agents. they can do that. and this is, again, Dustin, back to the place where what got you here won't get you there. You got to six figures because you were endlessly curious, and you were experimenting, and you were learning all these different things.
Jeni: And, to get to seven, to, to scale from,a million to 10, 10 to 50, we actually need to have enough trust with guardrails and responsibility and ownership where our team can be the ones that are out [00:32:00] there during our innovation hour that we have once a week in our company, right? And can be like, "Hey, I have an idea for an agent that will do this.
Jeni: What do you think? Does this align with our strategic plan this quarter? Or should we put it off and talk about it next quarter?" But ultimately, we're hiring the people that are gonna be doing that, and then, geek out yourself all you want. it's cool stuff. I love it, but it's not gonna... It's-- In itself, it's not gonna grow your business.
Dustin: It's a great excuse to get distracted in a new way that feels like progress, even though,many times it's not, right? so we got strategy, planning, systems team. So- And insight ... what? Insight. All right. Insight. That's a good one. I like that.
Jeni: And this is the one that, I mean, I've had clients in the past that just say straight up, "I'm allergic to spreadsheets."
Jeni: Like I don't-- and we have this idea that, that insight, that data has to be complicated. Now more than ever, this is something-- This is a place where AI shines [00:33:00] because I can come in and I can look, So for example, one of the companies that I work for, we were looking at what retention looks like over years of cohorts.
Jeni: So they have a curriculum company, and they were looking at people in-- who came in the, into the business in 2000-- sorry, in, in 2020, in 2021, 2022 by cohort, how long are they staying and making repeat purchases. And we saw that over time, we are having-- they're hanging on for longer and longer.
Jeni: This is a great thing. And we're able then, with that insight, to connect. We can reconstruct some-- what was it we do that we thought would lead to this that's actually working, and how can we do more of that?
Jeni: Yeah. That's
Dustin: so good. That makes my engineer brain happy. I love that. That's such like a practical, such a practical example of kinda dashboard level decision-making that a CEO should be super excited about [00:34:00] because it's so aligned with the systems and the strategy, aspects.
Dustin: Obviously, all five of these tie together. Yeah, please complete your thought on insight, and then we can, maybe we can double tap into at least one of these, before we run out of time today 'cause we, we-- I'd love to just sit here and talk for five hours and go through each one, but, we, we won't do that.
Dustin: But yeah. Any other thoughts on insight before we move on?
Jeni: Well, yeah, you s- you said the word, dashboard, and absolutely reporting dashboards and KPIs have a big place, a big central place. They're very important. But there are also, there are also things that you know and you could find evidence for that you're not gonna find on a dashboard yet.
Jeni: and a lot of times, founders know what's moving the needle in their business, and sometimes it's just, are we willing to admit that, to look at it? So, for example, I have a client that I was working with early in the year who has a, healthcare business, a telehealth, telehealth business, and they knew [00:35:00] that the majority of their c- of their customers, of their patients that came into their business were coming in through referrals, which to me, I'm like, "This is a wonderful sign.
Jeni: This is so exciting that you're giving such phenomenal service that people are just organically talking about you and getting their friends in," right? And so, however, this founder has really bad shiny object syndrome. And, a guru comes along who has a promise of, "Hey, let's take your list, and we're gonna mine your list for leads," and blah, blah, blah.
Jeni: And I said, "Wait a minute." You have a very inactive list. You have not been doing a phenomenal job nurturing them. Fine, everybody's been there, but you have this incredible opportunity right before you, which is we know that when people talk about you to their friends, that they come on and they become patients.
Jeni: And so this-- the strategy here that is, the next best [00:36:00] thing, it isn't necessarily the most scalable, right? It's not high volume, but it is high trust, which is what if we gave every one of your current patients every time you can wait for them to be like, "I love you guys," and then offer this? Or you could do it now to everybody and just say, "Hey, I'm gonna give you a coupon code.
Jeni: You can give this to any of your friends for fifty dollars off our front-end inta-intake evaluation." Because people are already ta-talking about it anyway, why not make it easier for their friends to say yes? So this is where, to bring it back to, this is not a dashboard kind of thing. It is strategy.
Jeni: It-- And we're not gonna see these numbers, presented in some sterile third-party thing. but we can say, instead of looking at all the possibilities out there, the insight piece of this says, "What is working?" And let us optimize and double down on what is already working, and there's an opportunity cost.
Jeni: We're gonna need to say no to some other opportunities [00:37:00] there. But if we go off and pursue those other opportunities instead of doing what's really gonna move the needle a bunch, especially like you get everybody who comes through your program to refer successfully two people, guess what? It's gonna scale.
Jeni: Yeah. Exponential growth. It's gonna scale. By definition. Exponential growth.
Jeni: Yeah. You got it. Yeah. So insight is the thing that ties it together, and I find that a lot of founders are sort of the weakest in this, or they think that just because they're tracking page views that they're doing it. But,the real thing is can I make decisions to understand based on information that will show me what's working, what's not working, and then, am I willing to make decisions based on, on, on the information that I have?
Dustin: Yes. Two, very important questions that aren't always, yeses, right? So sometimes we make decisions without the insight, and as sort of a gut or guess or shiny object, and then many times we get really good insights, and we [00:38:00] still choose not to pursue them or honor them, by, I guess, believing them and taking action towards them.
Dustin: So yeah, as we kinda get closer towards the wrap-up zone here, I love that we went through and at the level that we did through those five really key components, so strategy, planning, systems, team, insight. So I'm imagining a listener who's like they're grinding, they're at 200,000.
Dustin: all they want for Christmas is a million-dollar business, and they've got like little pieces of each of these things going. Like, where do you start? I, I would... And I, I'm-- maybe it's just completely different for every business, and everyone needs a, strategic advisor to sort of sit there and help them objectively decide where to start.
Dustin: But in your experience, Jenny, and having sat with so many founders in this journey, yeah, which of those five do you think you start? Or is it, is there not a one-size-fit-all, fits-all answer?
Jeni: So there's... I mean, I have an a- an assessment that's on my [00:39:00] website that anybody can come in and take.
Jeni: So I've got that on the homepage of, trueflowscaling.co. and that just goes through some very simple questions of, to help you identify which one is the biggest bottleneck that's going to keep you from scaling. However, it can be kind of discouraging, especially before you're at the six figures to, look at an assessment and be like, "Everything sucks.
Jeni: It's all horrible," right? So, so some of it, I would take, especially, I can... I use this evaluation with $3 to $10 million, companies all the time as just a very quick entry point into, okay, now let's look, let's explore more about what's going on and the complexity and the intricacy and how it's all related.
Jeni: There's a very simple question though, Dustin, that you can ask, and it is: If you had 50 new customers or clients sign up
Jeni: today, what would break first?
Dustin: Write that down
Jeni: too.
Dustin: so right alongside money doesn't [00:40:00] buy efficiency and what got you here won't get you there. yeah, and I think that's like a critical question in this stage of business, and I know there are people that hear that question are like, "I'd give anything to have 50 clients," because the constraint in their business is, leads and client acquisition.
Dustin: That is generally the constraint when you get up to six figures, right? But to go from six to seven, it usually becomes much more of a matter... to get to a multiple six-figure business sustainably, you have product market fit, you have some form of lead acquisition that works, whether you've realized it or documented it or doubled down on it yet, it's there.
Dustin: But then when you're at that point looking towards a million, three million, 10 million, this becomes a critical question. if someone gave you five or 50 new clients today, what would break? And that's like such a good strategic question because, if you've have even the, a basic kind of customer journey map, you can look at that and be like, oh, like we could never onboard 50 people or well, we could probably get them through onboarding, but we don't have enough, Zoom seats to serve [00:41:00] them in the way that we now deliver value.
Dustin: or we, yeah, we don't have the system in place to, process that much payment or whatever. there's always, there's gonna be all these constraints that start to identif- that start to come out.
Jeni: Or I can't get them results if I have that many, right? So the piece that is absolutely that will get us to, scalability the quickest, because a lot of what I do is scalability evaluation assessment strategy.
Jeni: and the thing that will get us to the heart of that, i- if your business model itself is not scalable, then you're going to have so much waste in other parts of your business, and you're gonna buy into the next thing that the guru says, or you're gonna chase that shiny object because no matter what, if you have wins, they're gonna be short-lived because ultimately, your business will be as successful as the offer itself and people's experience and success with that offer.
Jeni: And so if your offer doesn't scale, and this is where, I'll sit down in a 90-minute session with [00:42:00] somebody and be like, "Okay, we're gonna map out what this core offer is." Or maybe you have eight offers. Like I was saying about, the archeology piece, I can also be like... Or, and oh, we have eight payment plans, and we have, all of these offers that we've accrued over the years.
Jeni: So I want to get you down to a single lane, lean, scalable offer suite first, and then we will see what else will naturally just fall away based on that. And there's way you, there's ways you-- Yeah, offer first, and let's-- Because if we can't scale the, if we can't scale the offer, then we're gonna be stuck in very linear growth that's gonna come with a lot of friction on the way.
Dustin: Yeah, absolutely. Well, this has been amazing, as expected, and, it brought up some, old emotions that I think is actually really healthy for me to kind of reflect back on my own journey. if anyone's sitting here "Eh, I don't know if this is real," like I [00:43:00] think seven figures will, solve all my problems.
Dustin: if you trust me at all, believe me in that everything that Jenny said here is gold, and I really wish I would have had this, th- these, this guidance, a couple years ago when we were kind of hitting this own hockey stick moment in our business. so strategy, planning, systems, team, insights.
Dustin: what gets you-- what got you here won't get you there. you have to start with a lean offer first that will actually scale, and it's okay if you need to make changes to that because, again, what got you here won't get you there, and often those changes are necessary. And obviously you've got an amazing resource with your assessment, and this is the work that you do typically for three to ten million dollar companies, Jenny.
Dustin: But yeah, tell us, kind of next steps so people are like, "Oh my gosh, this is exactly what I needed to hear today, and I want to take some action toward improving the situation of my own business." what's the next best step for them?
Jeni: so taking the assessment is gonna help, diagnose which is most likely the most pressing bottleneck that you're experiencing right now.
Jeni: And, the [00:44:00] problem ultimately that I, that I-- the reason that I work with three to 10 as my primary folks is because, we've got product market fit. We've got, s- we've got a lot of fundamental systems here, but I've got a founder who still cannot get out of the day-to-day running of the business.
Jeni: We've still got all... It's very founder centric. the business is literally relying on them, their brain, and their nervous system all the time. So the thing that I love to do is actually create that freedom. That is why founders got into this in the first place. as far as kind of a day-to-day, how do you find me on ye olde interwebs?
Jeni: LinkedIn is a place that I'm hanging out a lot, so- Black Cat
Dustin: CEO it. she's got keywords stuffed all over the place. Jenny's everywhere.
Jeni: They're everywhere. Yes. I love it. I'm hanging out on LinkedIn. if you couldn't tell by my voice and demeanor, I'm actually very approachable,and very nerdy at the same time.
Jeni: But, I just love having conversations with people. So y'all find me on LinkedIn. it's a great place [00:45:00] for us to just to rub elbows and get to know each other.
Dustin: Love it. So Jenny B, J-E-N-I-B, and then you can go to trueflowscaling.co, and that's where you'll find the assessment and be able to get, deeper into the, the transformation that Jenny provides to her clients.
Dustin: Jenny, I'm so grateful for you. I'm so glad that, we've met, and we're gonna continue to grow together, and I'm, really appreciative of your time and wisdom that you shared today, so thanks for being here.
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