Ep: 113 - Work Less, Grow More: Jill James' Blueprint for a Self-Sustaining Business
What if the biggest thing holding your business back… is you?
In this episode of Scaling Expertise, I sit down with Jill James, founder of The Jill James, a fractional COO firm that helps expert founders scale without burning out or staying stuck in operator mode. Jill built her firm by asking one powerful question: “How can I help people do the work they love without being buried in admin?”
We dig deep into the invisible costs of overwork, the identity shift from doer to leader, and the moment Jill realized she needed to break her own rules to scale. If you’re feeling like your business can’t run without you, this episode is your wake-up call.
Jill shares hard-earned wisdom from scaling businesses to $10M+ and offers actionable ways to reclaim your time, build operational clarity, and let go of control—without compromising your vision.
Key Takeaways:
Founders can be the bottleneck. If your business can’t function without you, it’s not scalable.
Don’t sell your time—sell your thinking. Experts grow when they stop doing and start designing systems.
Scaling isn’t about doing more—it’s about doing less, better. Create space so the business can operate without you.
You don’t need to be a “visionary.” You just need to be clear about where you want to go.
Resist the "fixer" urge. Let your team solve problems so they can grow into their roles.
Fractional leadership. This can help expert founders transition out of operator mode with structure and sanity.
Jill is a featured author in The Wisdom Collection: Stories That Transform How We Live, Connect, and Lead—an anthology of powerful insights from business leaders who’ve built, failed, and figured things out the hard way so you don’t have to. Each chapter is practical, quick to read, and full of hard-won wisdom.
The book launches June 24 and will be available for just $1.99 during its first 24–48 hours.
Want the launch link or more details? Check out Jill’s announcement post on LinkedIn.
Resources Mentioned:
🔗 Check out Jill’s firm: The Jill James
📬 Get her insights: Subscribe to the newsletter
🤝 Connect via Beehiiv
Charity: Black Girls Code
Connect with Erin to learn how to Turn Your Expertise into Scalable Recurring Revenue.
Erin's LinkedIn Page: www.linkedin.com/in/erinaustin/
Scaling Expertise YouTube Page: https://www.youtube.com/@Scalingexpertise
More About Our Guest
Jill James
Jill James is CEO & Founder of The Jill James. As a recent client summed up, she is what would happen “if you could hire Sallie Krawchek, Dany Garcia, and Mackenzie Scott to run your company.” Jill started her career in New York City as an investment banking analyst with J. P. Morgan and personal wealth planner with AXA Financial (now Equitable). She moved to tech start-ups and held nearly every non-programming job in early stage companies, including product, marketing, sales, and C-level leadership. She used these experiences to found The Jill James in 2015, and now partners with self-funded founders to grow and run purpose-aligned companies.
At the University of Chicago, she earned a BA with honors in Political Science from The College and an MBA in entrepreneurship, strategy, and marketing from Booth School of Business. Originally from Greenwood, Wisconsin, Jill lives in Los Angeles with her kiddo and their very squeaky guinea pigs. She writes a weekly Beehiiv newsletter for owner/operators of small businesses. Learn more at thejilljames.com, including a video introduction and our most recent newsletters and blog posts.
Find Our Guest
Music credit: Paphos by Mountaineer
A Team Dklutr production
Blog Transcript:
Erin Austin: Hello everyone. Welcome to this week's Scaling Expertise, where we talk to experts who have scaled their expertise and also have some tips about how you can scale your expertise. I'm very excited for my guest this week, the Jill James—I love that—who is a business consultant who helps her founders go from founder to CEO. So welcome Jill, so much.
Jill James: Thank you, Erin. Thanks for inviting me.
Erin Austin: I'm very excited to have you here today. What you talk about is so applicable to this audience. But before we dive in, would you introduce yourself?
Jill James: Sure. So I'm Jill James, as you mentioned. My company is called The Jill James—not gonna get lost there. My focus is kind of in three areas: I'm a business manager, I'm an operator, and I also have a background in wealth management. So that makes it a little bit unique in that I mostly work with self-funded people and a whole different set of tools that we have when you are not having venture investors. That’s really an area that I've chosen to focus in—to help people who want to self-fund their businesses and grow them to the right size for them. So I think our conversation today is going to be very applicable to your audience.
Erin Austin: Absolutely it is.
Rethinking Scaling: The Self-Funded Founder’s Playbook
Erin Austin: And I'm going to jump right in with what you mentioned there about your target audience—about them being founders that aren't going to take VC funds. We're going to talk about scaling, we're going to talk about intellectual property, but I'd like to just start with how the misperception generally—that when we talk about scaling, we're talking about VC funding, and we're talking about software. We're talking about these things that we read about in magazines as opposed to the things that we do every day in our business. Have you found that kind of general misperception when you're talking to people?
Jill James: Yes. In my working background, I come from investment banking, wealth management, and venture-backed startups. And you can see I am not in that world. So it's: What can we take from that world? But if we follow that playbook—and that is a lot of what you see in the press, that is a lot of what you see on social media—it’s the “get big fast” playbook or the assumption that there is unlimited capital or you've just been handed a chunk of money, and you can go try some stuff out and figure out how it works before you have to sell anything to anybody.
That isn’t the real world for 98% of businesses.
So, as much as we hear about these venture capital businesses and it’s sexy to say, "Oh, they got 1.2 million in funding," or "They got 50 million in funding," whatever it is—sometimes that's just to figure out, "What are we gonna sell?"
That isn’t the reality for 98% of us.
And I think in particular, if you are a non-traditional founder or you didn't go to a certain set of 10 or 12 schools where you met the people who are gonna fund you, you are going to start your business with money that you earn by selling things. And then you're going to earn the right to borrow money from other people or from banks to accelerate the growth of your business.
It is a very different playbook. And I think what I am seeing is more people are evolving to: “I want to keep control of how this business grows, and I want to do it at a pace that's right for me—not what somebody else dictates.” And so when you choose that path to be self-funded, we have to be very intentional—especially from about $250,000 to $500,000 up to about $5 million.
We have to be extremely intentional in how we step through that time to help you grow without falling into some of the traps that are going to start to come into your world around seven figures, where lots of people start to say, “Oh, I can help you. Now you made it to seven figures. You're in the big leagues. Well, let’s get you on this different playbook.”
The foundation that it takes to build a self-funded business and to set a playbook for yourself is really what we work on with founders in my business.
Erin Austin: Thank you for that. Thank you.
From Venture-Backed to Self-Funded: Jill’s Journey to Building Her Own Path
Erin Austin: So having set that framework, let's go back a little bit. You mentioned you came from the venture world. How did you make that transition to where you are today working with this population of clients?
Jill James: Yes. That is a good question. So for a long time, being in—I think I worked at seven different venture-backed startups over my career—and been through lots of exits. And so I was always looking for what is that big idea? What is the idea that would get me venture?
I had a lot of other ideas that I didn't follow because they would not have qualified for venture, and they were probably all really legitimately good businesses where I would've made a lot of money. But I did not understand how that worked yet. I understood the get-big-fast model. That was business school, that was all the businesses I worked in. That was the goal.
So when it finally came down to it, I ended up leaving. I was the COO of a venture-backed tech startup, and I was seven months pregnant. There was a conversation about maternity leave, and it did not go well.
Erin Austin: No...
Jill James: It was about no leave. Maybe. It was about no leave. So I waddled my little self out of there. I took a minute to get organized, and I had had a number of people—I had partnered with more founders who had come from a place of knowing how to sell, having a good idea about a community or a business that they could establish—but no operational expertise in how to set up and run a business.
So I had self-funded founders who had seen me do that, and they had left the door open of, “If you ever want to do this fractionally or maybe would take a side job where you're not all consumed with building somebody else's business, I would hire you.” So I called a couple of those people and I said, “This is the situation, and I'm going to be having a baby, but until then we can start something and then we can pick it up again.” And they said, “Any help you could give me, I would just so appreciate having someone look over my shoulder, help me out with this, and whatever we can do.”
I really appreciated that because the first couple of years in my business, I worked very flexibly, more like a fractional COO. I think this is part of the process of especially an expertise business—you’re going to try out a bunch of stuff. I tried to work with different kinds of people. I worked on an hourly basis. I just kind of figured out: What is this? What are people asking me for?
That was almost my investment in finding my product-market fit.
In the evolution of that, about two years in, I saw an opportunity with lots of women who needed flexibility, who were establishing businesses because of that—often around caregiving. And so I redesigned what I was doing to make it a little bit more package-driven, knowing those women were probably not going to get venture, just given the numbers and the kinds of businesses they were establishing. I moved more in a direction around: How do I work with self-funded founders, and what does that mean, and what's my unique expertise that I can bring to that area?
What have I learned and the people around me—how can they help these people as well?
That was really the evolution. This was 10 years ago, right? My son is nine and a half. It was almost this time, 10 years ago, that this conversation happened.
Ten years later, I have a very defined: this is who we are, this is what we do, this is who we're for, and these are the reasons that we do it. All of that is very well-developed at this point, but I went through a phase of experimentation initially where I just got paid to show up and do my old job as my business. And that's a perfectly legitimate way to start.
Erin Austin: Absolutely. Thank you for sharing that because so many of us—there's so much information now—and it is really easy to get caught up in all the different way offers and ladders and all these things. And I have absolutely suffered from it. I'm post-corporate, who now works with a different population, and it has taken—I'm still evolving, frankly. I'm not 10 years out working with this group of people.
Learning who your best client is, the best way to help them—our expertise can be used in lots of different ways, but the more we work with people, the more we hear their pains, the more we start to speak their language, the more it makes sense. We can start to drill down on the best way to help them. You're probably not going to just come straight out of corporate—for most of us—and go straight into the final product, so to speak.
Jill James: Yeah, I think that's a great point. There is going to be an evolution in your entrepreneurial journey, even if you're a product-based business. The first idea that you have—if you're very lucky, it will be the successful one. But in most cases, there's a pivot, there's some amount of learning, there's a change in the market. And so we have to continue to look for the opportunity and move toward it as we learn more about ourselves and what our capabilities are, and who wants to work with us.
Redefining Scaling for Self-Funded Experts
Erin Austin: Now when you think—of course, this is a Scaling Expertise podcast—so, a lot of people have a very narrow definition of scaling as being, you know, selling books or courses or software, things like that. But what does scaling mean to you and your clients?
Jill James: Yes. So scaling in the self-funded world is a very intentional act. It's about milestones, and it's about knowing what are those points of investment and the next place we're going to land.
So scaling often—as you start as a self-funded business owner—there's the problem of where is the money gonna come from, right? So we need to be intentional about looking at where we are going next. How much money is it gonna take? What are we gonna have to sell? Who else do we need on the staff? What other resources do we need?
And sometimes that means there's gonna be a dip, where we need to move forward and we don't have the revenue yet. So, where are we gonna get that capital? Is it from a bank loan? Is it from a line of credit? Is it a 7(a) loan?
Learning that world of places that you can borrow for growth—that you know you can pay back because you're moving through a point in time and not stuck in “I don't know how to get out of this, let me borrow some money”—it's meant to accelerate you.
So I think that is the thinking on scaling: it's not “How fast can we get how big?” but “What's the next iteration of this business where we can be profitable at this size and deliver?” And how long is that gonna take? How quickly are we gonna move through this?
Because what I see is when you don't know what that next point of profitability is going to be, you get stuck in a trough where you are having to make extra investments in operating expenses, in people that you can't pay for yet. And you meant to move through that in three to six months, and all of a sudden it becomes two years and the debt becomes unsustainable, right? And then you get really stuck.
So you have to have a plan for what is the next milestone, what do we need to do to get there, and what's going to be the uncomfortable stuff that we have to do in the meantime to get us through this phase. Then you can be there and say, “I like this size of business, and this is great for me. I love it here.” Or you can be like, “That wasn't so hard. I think I want to go for the next one.”
And then we need to look ahead and say, not just based on the revenue number that you want to be at, but what is the right size of your business at the next iteration—where we hire the people, we have the profitability, you get paid what you want to get paid, you keep the culture that you want to keep. What's that next point? Okay, let's move toward that. How long is this next phase gonna take?
But I think it's the stepping-stone approach—making sure we're just moving through an investment phase to a next point of sustainable profitability. That's the way that we scale a self-funded business.
Erin Austin: You know, I think that even with the expert—certainly one who's relatively new in their business—they're not even thinking in terms of profitability. They're thinking in terms of matching their old salary.
And I'll say, when I first started being self-employed, I was not thinking about profitability. It was literally like, “How much do I need to make to pay my bills?” It was not about, you know, what does it really cost me to generate this much revenue? And so there is kind of a foundational misunderstanding—or lack of understanding, I think—for some experts about just that: about profits as opposed to just revenue.
Jill James: Yeah, I think that's a great point. There is definitely a transitional moment when you're that expert solopreneur to moving into “I'm going to run a scaled business now.” And other humans are involved—whether they are employees or contractors or other businesses that you work with.
How do I go from how I do it myself, and take most of the money and put it in my bank account, and just be tax-smart about that, to “How do I set things up so other people can replicate what I do at this level of quality that I want to sustain?” Because people still need to—it’s still mostly me, right?
And so how do I bring in the right people, and then how much is that going to cost? I think that that is a point where we really have to think through what you charge and how many clients you need, or how many sales you need, and what that next investment is going to be.
Because bringing on people is a big leap. It is expensive. They come with a lot of rules. I'm in California—ah yes, you had one part-time employee, you better have a retirement plan. You better be thinking about all of your compliance, right? That is that one human being for more than 10 hours a week. We have to do that.
So, you know, there are other places where it's not that, but we really do have all of these other layers of operating and administrative responsibility once you start to scale.
Do you want your expertise to become, “I want to get really good at operating a business?” Or “I want to get really good at going and finding customers and telling them my story and aiming my business in that direction?”
And I think that's one of the challenges—people get really bogged down at that next phase of “I don't know how to do any of this stuff, and it's really hard, and I keep getting letters, and they're scary, and now I'm spending time on hold, trying to figure out what's going on, and like, who do I need to solve this problem?”
The sales stop. You stop selling. You stop focusing forward. And you stop innovating. You stop trying stuff.
That is one of the big pitfalls of going from a single expert into a scaled business setting. We rise to the place where the administrative stuff overwhelms us.
Erin Austin: Yes. And then who do you get to help you with that? How do you get good at that a lot faster?
I'm a huge proponent of division of labor. There's something I don't even want to get good at. Like, for me to go from what is it—the zone of genius—not even adequate to decent would be like… that gap is, for some things, huge for me versus going from good to great, you know, which is where I'm trying to spend my time.
Sharing, Protecting, and Evolving Intellectual Property
Erin Austin: So you mentioned having a scalable, sustainable business. And from my perspective, you can't do that without developing some intellectual property. Not necessarily software, books, or courses, but making sure we're capturing our expertise—putting it in a form that it can be replicated by other people.
You know, as founders, we are the most expensive resource in our business. So how do we have less expensive resources deliver some or all of that value to our clients?
I get too many questions about, like, “I'm worried about people stealing my intellectual property,” and one of the things that you do is you have an Ask Me Anything, where you let people come and you give away your expertise for free. Some people—and I do a lot of that as well—are like, “Why do you give so much away?” Where do you see the benefit of sharing your expertise?
Jill James: Well, most of the things that I know, you will eventually learn, right? I was a proud business auntie earlier this year as one of my clients got on stage in front of a group of other women and said things that I know I said to her. She said them to this bigger group of women, and I was just like, “Yes. Pass on that message.” We all can get better at this.
I come from a place where innovation is the IP. Creating an organization that will be curious and continue to learn, continue to try new things, continue to really move ahead to new opportunities—and being smart about what we need to protect in that, and what is protectable.
Because innovation in and of itself is a discipline. It is not protectable. The product of your innovation might be protectable. The question is: is it relevant for a long time? If it takes several years to get a trademark, or it takes a utility patent—right? Is that a useful investment for you? Is that something that’s the product of your innovation that you need for a long time?
So a lot of what we're doing in our intellectual property is really that special sauce of how do we make our business ours? What are the operating procedures we follow? How do we think about who we bring onto our team? Other people can't replicate that.
That curiosity—did it move forward? Most organizations are not that. So you know that aspect of “we will continue to evolve” versus, you know, often people with intellectual property think, “I've got my thing; now I'm gonna milk it for the next 75 years.”
And that might be true—as you capture some of these things, put copyright on them. Absolutely. There are things that might live well beyond you, where your heirs can continue to get money from them. Understanding what those things are is really important, and where those fall in.
But I think sometimes people get too attached to, “I protected this thing so that nobody else can use it.” And it's really the defense of that, that they haven't thought through. Do you want to become an organization that is defending a copyright or defending a trademark? Or do you want to be this thing in the world?
So I think that’s kind of the balance of—you have to understand what intellectual property will and won’t do for you.
One of the things I do with my clients is we look at insurances—if intellectual property is important, how do we form a legal defense fund using insurance. That gives us the right to say, not only are we gonna write that cease and desist, but when you think you've scared us with a big lawyer, we have a bigger lawyer, and we're gonna write a nastier letter—because we have a legal defense fund that you didn't know we had.
I went through this with a client a few years ago, where there was a major manufacturer that thought they would scare her off. And she was like, “I have insurance for this. I'm getting a good lawyer.” And went ahead and wrote back the letter, and they were like, “Oh. Oh, she's for real.” Right?
So I think there are things like that—not just the intellectual property, but the defense of intellectual property—that, as small business owners, there are tools we can use to make us run with and against bigger companies. And I think that's a big thing to think about if you are gonna be an IP-driven business.
Erin Austin: I love that. And I will—people probably forget this about me—but my brand name, Think Beyond IP, was about not just copyrights, trademarks, patents. It was about all kinds of intellectual capital, as I called it. You know, which it is called, but which nobody wanted to hear me talk about.
That was my evolution—like, okay, nobody really wants to talk about intellectual capital. But it’s exactly—of course, I didn’t put it the way you put it—but about culture, innovation, all those things. Insurance. There’s a whole ecosystem of how we create a business that is differentiated, that people want to work in, that clients want to work with.
It’s not just about what is filed in a copyright office. And those things are all absolutely so important. So thank you for putting it that way. I feel better about...
Jill James: I’m so glad to hear that.
Erin Austin: I feel so much better.
When It’s Time to Call in Strategic Help
Erin Austin: So tell me how your clients know, “Hey, I need to call Jill.” What’s happening in their businesses?
Jill James: Yeah. So often with my clients—like you asked me about why I do so much stuff for free—and I consider, I want to be Mackenzie Scott-level giving. And not keeping what I have. I want lots of people to be successful. So my business model—what I’ve settled on for my own growth—is more of a freemium model. Lots of people are on my newsletter. Lots of people come to my free stuff. We work with 10 or 12 clients a year, and a lot of those clients stay on for multiple years. So really, when it comes to new clients, we’re taking on four to six new clients a year, until they phase through and hire permanent people—if they get that big—to take on permanent jobs, all of those four or five, six things we’re doing for them.
So I think the point that people end up calling me is they either say, “Hey, I’ve been running this business for a while. I have an idea of how to take it to the next level, but I need someone to help me think through: What is that? What are my options? How could I do it?”
And then: How do I stay true to me while I do that? What are the centering principles that matter, that we’re building this business around? What are the forms the business could take that don’t trade off who I am?
What matters to me? Getting paid, right? Because none of us can go to zero. We gotta get paid while we build these things. And when I get to the other side, is it still a business I’m going to be happy running? Is it still a thing? Does it become somebody else’s thing or is it my thing?
So I think when you’re having thoughts like that—that’s the moment to call me as a thought partner and a strategist of what could it be. Let’s talk about what it could be. And that’s bringing in the structures and different capital models and things like that. That’s where I draw a lot on my venture background and also what I know about money management: how would we make that happen?
The other piece that people call me for is: “All I’m doing now is admin.” Like, I really want to get back to focusing on the growth of my business, selling things, talking to customers, running my team—and I’m so bogged down in all this other stuff, and I don’t even know the right questions to ask.
And also, I know I’m getting these giant tax bills. I know they’re more. I know I could be smarter. I know I could give more benefits to my people. I tend to work with very generous founders who do more than the law requires. They want to share—'a rising tide lifts all boats.' That’s the attitude.
So: How could I do that? What’s good for me, and what’s good for them? Very often it’s, “How do we fix the running-it part of the business so that you are doing the running-it part that you want?” And we take all that stuff that—when you say something like, “Hey, I’d like to implement this in the business,” and I just see 11 to 15 things we’re going to need to do to do that. You don’t have to go through the trial and error of what are those things. We make a checklist, we step through them, we prioritize them, and we might, in many cases, just do them for you.
So I think that part is like an operating partner—an experienced operator in so many different areas of running small business. And when I say small, that’s up to like $15 million, right? I’m not just talking about $100,000 businesses here. There’s a wide range of small business.
But I think that’s the point—when the operating of the business has gotten overwhelming for you, but it’s still cost-prohibitive to bring in a really experienced operating partner—that’s the other time to call me.
Looking Ahead: What’s Next for Jill & How to Connect
Erin Austin: That’s fantastic. So speaking of how you work with your clients—is there anything new and exciting coming up in your business that you’d like to share?
Jill James: Yes! I’m really investing in my newsletter and the community around it. It’s free. We have lots of resources. I don’t want anyone to fail in starting a business because they didn’t file a piece of paper or didn’t know they had a deadline, or they got behind on their taxes—right? All of those things that you just don’t know when you first start a business.
So the newsletter and the community around that are free, and it’s just something I want as many people as possible to benefit from—to get to the place where they could become my clients. That’s all. We’re really focused on: What else can we do for that community of self-funded small business owners to help them get to that point?
And on the other side of the business, I’m really leaning more into some of the wealth management aspects. That’s kind of a hidden part. I was a registered investment advisor for several years, and I’ve been through all the training on personal wealth. That comes from my investment banking background as well.
When you’re in a pass-through entity—like an S Corp or LLC—the opportunities around how to compensate yourself and what your financial world looks like are very different than when you’re working for a venture-backed company where you just take a salary and hope for a payout down the road.
So, especially with the current administration and all the flux, I think the question is: How can we not be afraid and operate in a smart way? There’s a layer of understanding your responsibilities as a business owner—but also your opportunities. That’s something more and more people are asking about in our operating work.
Erin Austin: Ah, well, I will say I’m going through that right now, so that is definitely hitting home for me. Very interesting. Thank you for sharing that.
And you answered my last question, which is: what’s the first step for people to get started on this journey? Signing up for your newsletter and getting access to all the generous information that you share is fantastic. We’ll make sure we have links to everything in the show notes. Where else can people find you, Jill?
Jill James: My website is thejilljames.com. If you want to join the newsletter, it’s thejilljames.com/newsletter. I also have a booking link on my site. I know people are sometimes hesitant to use it, but I’ll talk to anyone for 20 minutes and brainstorm with you. So feel welcome to use that if you’ve heard something here you want to talk more about.
I’m on LinkedIn, Threads, BlueSky, and Instagram as @thejilljames. And then my personal LinkedIn is Jill D. James.
Erin Austin: I’m curious about your use of Instagram for what you do—do you find your clients there?
Jill James: Instagram for me is more of a credibility step. I talk to a lot of people of various ages, and one of their checks—especially for some of the more creator-driven businesses I work with—is they go to my Instagram page first. They want to see that I’m legit, that I’ve made an effort.
So we don’t do a lot of original content. We repurpose a lot of the newsletter content and just repackage it with graphics for Instagram. Or I’ll make short videos, or we’ll take an AMA clip. But it’s an important credibility piece. I treat it like a billboard—a live billboard. When you pass by, is there something useful there, and do you know how to contact me?
That’s the role for Instagram. It’s not directly driving business—but I do hear a lot of people say, “Hey, I found you because you posted something interesting on Instagram, and I wanted to know more about that.”
Erin Austin: Yeah, yeah, yeah. That is why I haven’t used it—what could I do that would be catchy enough for Instagram? I feel like it needs another level of creativity than, say, LinkedIn. So yeah, I’ve been thinking about that one. And then—do you use TikTok?
Jill James: I don’t use TikTok. I’ve had security concerns about it from the beginning. Many people over the years have said, “This is new—you could be the ‘blank’ of TikTok,” and I’ve had to say no.
My business has never been on Facebook, and we’ve been off X (Twitter) since 2017. That’s part of my centering principles—if the only way my business can make it is by being on platforms I don’t want to be on, then I’m okay if I fail.
Erin Austin: That’s a great way to look at it. Well, this has been a wonderful conversation. Thank you so much, Jill, for generously sharing your wisdom with the audience. And to everyone—please make sure you get on Jill’s email newsletter list. So much valuable information is shared there. And thank you again—hopefully we’ll do this again soon.
Jill James: Thank you, Erin. I would love that. Thanks for having me.