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.

Thank you, Erin.

Thanks for inviting me.

I'm very excited to have you here today.

you talk about is so applicable to this audience, but before we dive in, would you introduce yourself?

Sure.

So I'm Jill James, as you mentioned, my company is called the Jill James, not gonna get lost there.

so my focus is kinda 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, whole different set of, Tools that we have when you are not having venture investors.

So that's really, an area that I've chosen to focus in to help people who wanna self-fund their businesses and grow them to the right size for them.

So I think our conversation today is gonna be very applicable to your audience.

Absolutely it is.

And I'm gonna jump right in with what you mentioned there about your target audience, about them being founders that aren't gonna take VC funds.

And we're gonna talk about scaling, we're gonna 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?

Yes.

Mm-hmm.

in my working background, I come from investment banking, wealth management, and venture backed startups.

Mm-hmm.

And you can see I am not in that world.

Right.

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 is 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.

Mm-hmm.

So, you know, as much as we look at, we hear about these venture capital businesses and it's sexy to say, oh, they got 1.2 million in funding, or they got mm-hmm.

You know, 50 million in funding, whatever it is.

sometimes that's just to figure out what are we gonna sell?

Yes.

And 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.

Mm-hmm.

you are going to start your business with money that you earn by selling things, and then you're gonna earn the right to borrow money from other people or from banks mm-hmm.

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 wanna do it at a pace that's right for me.

Mm-hmm.

And 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 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 gonna 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.

Thank you for that.

Thank you.

So having set that framework, let's go back a little bit.

You okay.

Mentioned you came from, the venture world.

How did you make that transition to where you are today working with this population of clients?

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?

Mm-hmm.

And 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.

Mm-hmm.

But I did not understand how that worked yet.

I understood the get big fast model.

Right.

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.

And so it was about no leave.

Maybe it was, it was about no leave.

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 wanna 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 gonna be having a baby.

But you know, 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.

And I really appreciated that because the first couple of years in my business I've worked very flexibly, more like a fractional COO.

Mm-hmm.

I think this is.

Part of the process of especially an expertise business, is you're gonna try out a bunch of stuff.

I tried to work with different kinds of people.

I worked on an hourly basis.

You know, I just kind of figured out like, what is this?

What are people asking me for?

You know, 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 are 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 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.

Like what have I learned and the people around me, how can they help these people as well?

so that was really the evolution.

This was 10 years ago, right?

Mm-hmm.

My son is nine and a half.

It was almost this time, 10 years ago that this conversation happened.

Mm-hmm.

10 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 mm-hmm.

Do my old job as you know, my business.

And that's a perfectly legitimate way to start.

Absolutely.

Thank you for sharing that because so many of us, you know, there's so much information now.

Yeah.

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 mm-hmm.

now works with a different population and it has taken, it is, I'm still evolving.

Frankly, I'm, 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 you know, 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.

Like we can start to drill down on the best way to help them, and that you're probably not gonna just.

Come straight out of, this corporate for most of us, and go straight into the final product, so to speak.

So, yeah.

Yeah, I think that's a great point that, there is going to be an evolution in your entrepreneurial journey even if you're a product-based business mm-hmm.

The first idea that you have.

If you're very lucky, it will be the successful one.

Mm-hmm.

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, you know, ourselves and what our capabilities are and, who wants to work with us.

Now when you think, of course, this is a scaling expertise Yes.

Uh, podcast.

So, a lot of people have a very narrow definition of scaling as being mm-hmm.

You know, selling books or courses or software, things like that.

But what does scaling mean to you and your clients?

Yes.

So scaling in the self-funded world is a very intentional act.

Mm-hmm.

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 of looking at where are we 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.

Mm-hmm.

So, where are we gonna get that capital?

Is it, from a bank loan?

Is it from a line of credit?

Is it a seven 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 is 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?

Mm-hmm.

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.

Mm-hmm.

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?

Mm-hmm.

And then you get really stuck.

Mm-hmm.

So you have to have a plan for what is the next milestone.

What do we need to do to get there what's gonna be the uncomfortable stuff that we have to do in the meantime?

Mm-hmm.

Um, 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 wanna go for the next one, and then we need to look ahead and say, not just based on the revenue number that you wanna 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 wanna get paid, you keep the culture that you wanna keep.

What's that next point?

Okay, let's move toward that.

What's, 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.

You know, I think that even with the expert, certainly one who's relatively new in their business and they're not even thinking in terms of profitability, they're thinking in terms of matching their old salary and I'll say, you know.

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 to me to generate this much revenue?

and so there is a like kind of a, a foundational misunderstanding or lack of understanding, I think for some, experts about just that, about profits as opposed to just.

Revenue.

So Yeah.

Yeah, I think that's a great point.

There is definitely a transitional moment when you're that expert solopreneur.

Mm-hmm.

To moving into, I'm going to run a scaled business now.

Mm-hmm.

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?

Self.

Mm-hmm.

And to take most of the money and put it in my bank account.

Right.

And just be tax smart about that.

Right.

And how do I set things up so other people can replicate what I do mm-hmm.

At this level of quality that I wanna sustain.

Mm-hmm.

Because people still need to, you know, still mostly me, right?

And so how do I bring in the right people and then how much is that gonna cost?

I think that that is a point where.

We really have to think through what you charge.

Mm-hmm.

And how many clients you need, or how many sales you need, and what that next investment is gonna be.

Because bringing on people is a big leap.

It is expensive.

Yes.

Yes.

Right.

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, really do have all of these other layers of operating and administrative responsibility once you start to scale.

Mm-hmm.

And do you want your expertise to become, I wanna get really good at.

operating a business.

Mm-hmm.

Or I wanna get really good at going and finding customers and telling them my story mm-hmm.

And aiming my business in that direction.

And I think that's one of the challenges of people get really bogged down at that next phase of.

I don't know how to do any of this stuff.

Mm-hmm.

And it's really hard, and I keep getting letters and they're scary and I don't wanna like, and now I'm spending time on, 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 and you stop trying stuff.

that is one of the big pitfalls of going from a single expert.

Into a scaled business setting mm-hmm.

Is, we rise to the place where the administrative stuff overwhelms us.

Yes.

And then who do you get to help you with that?

Mm-hmm.

Right?

How do you get good at that a lot faster.

Mm-hmm.

Right.

Yeah.

I'm a huge, Proponent of division of labor, there's something I don't even wanna get good at.

Yes.

Like for me to go from, the, uh, what is it, the zone of genius, go, yes.

Not even adequate to decent would be like, that gap is, for some things is huge for me versus going from good to great, you know, which is where I'm trying to spend my time.

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 you know, 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.

And so 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 a ask me anything.

Mm-hmm.

Where you let people come and you give away your, expertise for free.

some people and I do a lot of that as well, and people are like, why you give so much away, but where do you see the benefit of sharing your expertise?

well, most of the things that I know you will eventually learn, right?

Mm-hmm.

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, mm-hmm.

She said them to these, bigger group of women.

And I was just like, yes.

Pass on that message.

Mm-hmm.

We all can get better at this.

Mm-hmm.

So I think, 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.

Mm-hmm.

Is not protectable.

Right.

The product of your innovation might be protectable.

The question is like, is it relevant for a long time, if it takes several years to get a trademark, or it takes, utility patent, right?

Mm-hmm.

Is that.

A useful investment for you?

Is that something that's the product of your innovation mm-hmm.

That you need for a long time?

And 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?

Mm-hmm.

How do we think about who we bring onto our team?

Other people can't replicate that.

Mm-hmm.

And I think also that curiosity, did it move forward?

Most organizations are not that.

Mm-hmm.

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.

Mm-hmm.

Absolutely.

There are things that, you know, might live well beyond you where your heirs can continue to get money from them.

Mm-hmm.

And understanding what those things are are 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.

Mm-hmm.

Like, do you wanna become an organization?

That is defending a copyright or defending a trademark.

Mm-hmm.

Or do you wanna be this thing in the world?

Mm-hmm.

so I think that's the kind of the balance of you have to understand what intellectual property will and won't do for you.

Mm-hmm.

I think one of the things that I do with my clients is we look at insurances.

if intellectual property is important is mm-hmm.

How do we form a legal defense fund mm-hmm.

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, you know, scared us with a big lawyer, we have a bigger lawyer and we're gonna write a nastier letter.

' cause 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, you know, there's like a major manufacturer that thought they would scare her off.

Mm-hmm.

And she.

It was like, I have insurance for this.

Mm-hmm.

I'm getting a good lawyer.

Right.

And went ahead and like, 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 mm-hmm.

Yeah.

Is a thing as small business owners, that there are tools that we can use mm-hmm.

To make us run with against bigger companies.

And I think that's a big thing to think about if you are gonna be an IP driven business.

Yeah.

I love that, and I will, people probably forget this about me, but the, my brand name Think Beyond IP was about kind of not just.

copyrights, trademark patents, it was about all kind of intellectual capitals I called it, you know, which it is called, but which nobody wanted to hear me talk about, which is yeah, what my evolution was 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 wanna work in, that clients wanna 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 I feel better about, I'm so glad to hear that.

I feel so much better.

So tell me how, your clients know, Hey, I need to call Jill.

Like, what's happening in their businesses?

Yeah.

Yes, yes.

so often with my clients, like you ask me about like why I do so much stuff for free and I consider like I want to be Mackenzie Scott level.

Giving Right.

And not keeping what I have, right?

Mm-hmm.

And 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.

Mm-hmm.

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.

Mm-hmm.

Right?

Mm-hmm.

Until they phase through and hire, permanent people mm-hmm.

if they get that big to take these on permanent jobs, all of mm-hmm.

You know, four or five, six things we're doing for that.

Mm-hmm.

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 like how to take it to the next level, but I need someone to help me think through what is that right?

Like 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.

Mm-hmm.

We gotta get paid while we build these things.

And when I get to the other side, is it still a business?

I'm gonna be happy running.

is it still a thing?

Does it become somebody else's thing or is it my thing?

And so I think when you're having thoughts like that's the moment to call me as a thought partner and a strategist of what could it be?

Right.

Let's talk about what it could be.

and that's like kind of bringing in the structures and, you know, different capital models and things like that.

And that's where I draw a lot on my venture background.

Mm-hmm.

And also what I know about money management of like, 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 wanna get back to, focusing on the, 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, right?

Mm-hmm.

They wanna share all the rising tide lifts, all boats.

That's the attitude.

Mm-hmm.

So, how could I do that?

What's good for me and what's good for them?

So, you know, that's very often of 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, you know, 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 gonna need to do to do that.

Right?

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, you know, 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, like.

You know, that's up to like $15 million, right?

I'm just talking about a hundred thousand dollars businesses here.

There's a wide range of small business.

Mm-hmm.

But I think that's, the point of 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.

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?

Yes.

I'm really investing in my newsletter and my community around that.

something that'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 they didn't know they had a deadline mm-hmm.

Or they got behind on their taxes.

Right.

All of those things that you just don't know when you first start a business.

Mm-hmm.

So, you know, the newsletter and the community around that, are free and it's, you know, just something that I want as many people as possible to get to the place where they could be become my clients.

Right.

Like, that's all.

Mm-hmm.

Uh, so we're really, you know, focused in on like, what else can we do for that community?

Of self-funded small business owners to help them get to that point.

and I think on the other side of the business, I'm really leaning more into, some of the wealth management aspects of, you know, that's kind of a hidden aspect.

I was a registered investment advisor, for several years.

And so like I've been through all the training on, personal wealth.

Mm-hmm.

Uh, and that's part of it be coming from investment being as well.

when you're in a pass through entity, when you're an S corp.

When you're an LLC.

The opportunities of how to compensate yourself.

Mm-hmm.

And what your world are look very different than when you have an investor who said you take a salary mm-hmm.

And you're gonna work for a long time mm-hmm.

Until you get paid out.

I think the piece of like, especially in the flux of the current administration, I.

How can we not be afraid and operate in a smart way?

And that additional piece of, you know, your responsibilities as a business owner mm-hmm.

But also your opportunities.

That's a new layer.

I think that's really, more people are asking about in our operating work.

Ah, well, I will say I'm going through that right now, so that is definitely hitting home for me.

So, very interesting.

Thank you for sharing that.

And you answered my last question, which is first steps for people to get going on this journey, but signing up for your newsletter and getting access to, all of the, generous information that you share, I think is fantastic.

We'll make sure we have links to everything in the show notes.

Where else can people find you, Jill?

So my website is the Jill James.

If, you wanna join the newsletter, it's the jill james.com/newsletter.

I also have a booking link on my website.

I know people are a little hesitant to use it, but I'll talk to anybody for 20 minutes and mm-hmm.

And brainstorm with you.

So, you know, feel welcome to use that if you know you've heard some things here that you wanna talk about.

I'm on LinkedIn Threads Blue Sky.

Hmm.

And Instagram, as, the Jill James.

Mm-hmm.

the company is, and then my personal LinkedIn is Jill d James.

I'm curious about your use of Instagram for what you do.

Like, do you find your clients there or have?

Do you use Instagram?

Instagram for me is more of a credibility, uh mm-hmm.

Step, I talk to a lot of people of like.

Various ages.

Mm-hmm.

Right.

And one of their checks for, especially for some of the more creator driven businesses that I work with, is they go to my Instagram page first.

Mm-hmm.

Mm-hmm.

And they wanna see that I'm legit.

Mm-hmm.

And that I've made an effort.

So we don't do a lot of original content.

Like 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 a MA clip.

but it is an important.

Credibility.

I treat it like a billboard.

Mm-hmm.

Like it's a live billboard for me.

Mm-hmm.

Of when you pass by.

Is there something useful there and do you know how to contact me?

So that's really, that's the role for Instagram.

you're right, it's not driving mm-hmm.

Business directly.

But I do hear a lot of people say, Hey, you know what, I really, I found you because you put something interesting on Instagram and I wanted know more about that.

Yeah, yeah, yeah.

That is why I haven't used, what could I do, that would be catchy enough for Instagram, which I feel like needs like kind of another level of creativity than say LinkedIn and so yeah, I've been thinking about that one.

And then, do you use TikTok or.

I don't use TikTok.

I have all the security concerns about that and I have from the beginning.

so yes, I've had many people over the years say, Hey, this is new.

You could be the blank of TikTok.

And I was just, you know, I've had things like that.

I've, my business has not been on Facebook and we've been off.

What X since 2017.

Mm-hmm.

Yeah.

And I think this is part of, you know, my centering principles is if the only way my business can make it is by being on platforms that I don't wanna be on, then I'm okay if I fail.

Hmm.

That's a great way to look at it.

Yeah.

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 and, 'cause.

Of information shared.

And thank you again.

yeah, hopefully we'll do it again soon.

Thank you, Erin.

I would love that.

Thanks for having me.

I.