Strategic Operations Support

With Jill James, the founder and CEO of The Jill James, a strategy and operations consulting company that supports self-funded executives in building and running profitable companies. Jill is a business strategist and Chief Operating Officer that helps founders go from early concept to $5-$10 million without giving up equity. She has done most of the non-engineering jobs in SaaS and services companies. She has also been a personal financial planner, worked in investment banking, and has an MBA in entrepreneurship and strategy from Chicago Booth.

In our conversation, Jill shares her insights on money mindset in entrepreneurship, and emphasizes the significance of starting and scaling your business with a focus on aligning with your purpose and values over profitability. We also discuss the importance of considering legal implications in decision-making for your business (which impacts Jill’s daily work, too), and recommends seeking advice from the right professional advisors, particularly for entrepreneurs who may not have a clear understanding of their personal and business finances.

Join us for this insightful conversation with a leading expert that supports self-funded business owners quickly scale in a way that is true to their goals and values!

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Takeaways & quotes you don’t want to miss from this episode:

  • Importance of having money management and an abundance mindset.
  • Design your business that aligns with your values and goals, rather than simply focusing on profitability.
  • Why is it important to understand a business’s unit economics, margins, and pricing?
  • The complexity of managing a business with remote teams and the importance of considering tax implications before making decisions.
  • How to find the right professional advisors for your business?

“Many of us think of money like a pond, and a pond doesn’t have an inlet except for when rain shows up and we’re not in control of the rain… over time, as our money mindset expands, we think of money like a river. It has an outlet, goes by, and has a purpose. But money is really a flow state. It’s a tool that enables us to do other things.”

-Jill James

Check out these highlights:

  • 09:42 Principles of wealth creation that Jill wishes most people knew.
  • 21:28 Jill discusses the significance of aligning values in entrepreneurship based on her experiences with her clients.
  • 28:03 Some notable insights or “aha moments” her clients have experienced during the business design bootcamp process she guides them through.
  • 44:07 This is where vigilance comes in when it comes to asking the right questions to uncover a professional advisor’s values and alignment with your business goals…
  • 49:18 Jill’s takeaway to leave with the listeners.

How to get in touch with Jill on Social Media:



You can also contact Jill by visiting her website here.

Special offer for the listeners: Sign up at to get a FREE resource with thousands of dollars of tips, shortcuts, and operating knowledge to help you design and run a profitable company that works for you.

Imperfect Show Notes

We are happy to offer these imperfect show notes to make this podcast more accessible to those who are hearing impaired or those who prefer reading over listening. While we would love to offer more polished show notes, we are currently offering an automated transcription (which likely includes errors, but hopefully will still deliver great value), below:

GGGB Intro  00:00

Here’s what you get on today’s episode of Guts, Grit and Great Business®…

Jill James  00:04

Many of us think of money like a pond, and a pond doesn’t have an inlet except for when rain shows up and we’re not in control of the rain. The pond can dry up the pond can get very small the pond could get murky. Over time as our money mindset expands, we think of money like a river. It has an outlet, it goes by, it has a purpose. You can drink it, you can divert it, you can let it flow past you. But money is really a flow state. It’s a tool. It’s something that enables us to do other things.

GGGB Intro  00:35

The adventure of entrepreneurship and building a life and business you love, preferably at the same time is not for the faint of heart. That’s why Heather Pearce Campbell is bringing you a dose of guts, grit and great business stories that will inspire and motivate you to create what you want in your business and life. Welcome to the Guts, Grit and Great Business® podcast where endurance is required. Now, here’s your host, The Legal Website Warrior®, Heather Pearce Campbell.

Heather Pearce Campbell  01:03

Alrighty, welcome. I am Heather Pearce Campbell, The Legal Website Warrior®. I’m an attorney and legal coach based here in Seattle, Washington, serving online information entrepreneurs throughout the US and the world. Welcome to another episode of Guts, Grit and Great Business®. I am super excited to welcome back my friend, Jill James. Welcome, Jill.

Jill James  01:28

Thank you, Heather. I’m so excited. Thank you for having me back.

Heather Pearce Campbell  01:31

Oh, my gosh, I’ve been looking forward to this. And I can’t even remember how long it’s been since we recorded the first call.

Jill James  01:39


Heather Pearce Campbell  01:41

Totally. I will definitely post that link as well in the show notes. So if you’re listening, you’re gonna want to pop back over to conversation number one that I had with Jill. But if you are just now getting introduced to Jill, Jill is the Founder and CEO of The Jill James, a strategy and operations consulting company that supports self-funded Founder / CEOs in business and running profitable companies. Her services and programs are tailored specifically to help self-funded founders design the company they want to run, balancing purpose and personal values with building sustainable wealth. I love this so much. I mean, it’s short and sweet, and to the point. And there’s so much in there. I mean, you and I were just talking about like some of the things that we could cover in this conversation together. And it says it’s a big topic. It’s a meaty topic and such an important one. And it’s so important that we get this right at the right time in our business. So welcome Jill, I’m so excited to have you back. I would love for you to give us a refresher. I know we probably chatted about this in the first episode we did. But for folks that are listening today, give us a refresher a little bit about your background, where you come from, what led you into this specific niche in your area of consulting?

Jill James  03:03

Sure. And again, thank you, I know you and I’ve had so many conversations, and we’re like we were finally doing it. I think my background is like I come from a small town in central Wisconsin, about 1000 people, it’s farming community. And so both of my grandparents had small businesses. So my legacy is I come from a family of people that our family was employed in small businesses. I went to my grandparents for the summer. And I pulled soda fountain, you know, I was a soda jerk. And I made ice cream sundaes, and I filled the candy case. And, you know, I learned to make change and do math and things like in my grandparents businesses. And so that kind of small town customer service mentality has always come with me. But then I ended up you know, going to prestigious university and out of that I ended up in investment banking, you know, which was very different of it. Yeah, in New York, a little bit of cognitive dissonance there. But you know, learning really like how the money system works, how how wealth works, from being a banker, I also then was a private wealth advisor for a couple of years before I went to work for the CEO of that fortune 500 company as his analyst and Deputy Chief of Staff. So you know, I kind of went from in this little town where everybody knew each other and all the people that I had gone to school with for all 12 grades right there remember things like what I misspelled in the third grade spelling bee to like, you know, there’s a guy from France would show up and we talk about billions of dollars of things that we’re going to move around. So I think one of the things that I took away you know, from my time in finance and why didn’t stay was a lot of it was making a lot of money for people who already had a lot of money. And that’s something that I’ve held on to as I’ve gone through then, you know, some several tech startups several exits, and ultimately ending up working with founders who intentionally want to have small and medium sized businesses that are self-funded, that is so important to me, because it’s one access to really, you know, the American dream, but also getting out of wage and hour, and other people’s money that we don’t get rewarded for. So, you know, really making entrepreneurship accessible for people using those super 1%, high level tools and tax information, everything that I learned from being in finance and running other people’s companies and spending other people’s money. But bringing that to a level of, you know, what do you want to achieve. And the other big shift in that was, it’s very purpose driven. For me, work didn’t work. For me, I started my company, when I was a CEO, a venture backed company, I was seven months pregnant, and there wasn’t space for me to take care of myself, take care of my child, and work there. Like it just there was no compromise around that. So I left and started a company. And once you do that, you hear from all the other people who are like, Well, I didn’t really say this, but I had to start my company because there was no better alternative. And I think we are more and more seeing that in, you know, women still leaving the workforce, people of color and diverse, you know, struggling marginalized communities are leaving the corporate workforce at a much higher rate, because they cannot find the satisfaction in work. And the only way to define that is to have their own company. So you know, it’s been a really interesting, I’ve been doing this for eight years, the last five has been very interesting, because I think there’s more and more momentum around, I want to work for myself, but how do I do that? And so, you know, partners like you and I that have been there and can bring a really elite level of thinking and service, but at a level that a small business owner needs. That’s really my business today around operations, finance strategy, and figuring out how are we going to define a profitable business that you want to run? And then what are those really important cultural core values that we do not violate? Because we have to vigilantly protect those as we grow in who we hire who we work with the messages we put on market, because over time, everyone wants to dilute it. I mean, McKinsey is talking about, you know, I don’t think anyone that works with McKinsey can actually have a purpose driven business, but they got a big white paper on it now.

Heather Pearce Campbell  07:20

Oh, boy, right. I know, actually, one of my clients has done some consulting, and he’s a therapist, like his background is in therapy, but cause like personal consulting with folks at McKinsey. And anyways, there’s lots of laughs We have about that. But a couple things that you raise that are super important, is one, the trend that we’re seeing now. And one of my friends, Paul’s Eleazar, who really works in the socially aware business space, you know, socially conscious social impact based businesses that he’s seeing that is super exciting to me and to folks who care about this space is not only people exiting the traditional workforce, because it is not working for them. So you and I were talking about women, right? You mentioned people of color, minorities exiting, I think the word you had for it is just a level of fed up fitness that people are having. And the reality for any of us that want to see the systems changing is that people are no longer waiting around for the system to change, right? They’re exiting this long standing traditional framework and just creating their own thing, which my entrepreneurial heart really loves. And my legal heart loves as well. And what Paul mentioned the other day, because we had another conversation on the podcast, as well as that these are the folks investing back into women and minority owned businesses, right, which I also love. And I see so many women, you know, largely consulting with women. And of course, like in my work, I work with both men and women. Right. And generally, I think that we should all be open to that for legal reasons. And it’s really exciting to me to see the growth in the, you know, the online and business industry generally with people doing that. So I love it. This is a conversation I care a lot about. Before we jump into some of the juicy things that we’ll talk about. I am curious from your money and financial background. Are there like two or three principles that you think most people don’t know about? The flow of money generally about wealth creation that you wish more people knew?

Jill James  09:39

Yeah, that’s a great question. I think one is like something we can visualize. Many of us think of money like a pond, and a pond doesn’t have an inlet except for one rain shows up and we’re not in control of the rain. The pond can dry up the pond can get very small the pond could get murky. Our brains many of us think of money as a pawn. Mind over time as our money mindset expands, we think of money like a river, right? It has an outlet, it goes by it has a purpose, you can, you can drink it, you can divert it, you can let it flow past you. But money is really a flow state, it’s a tool, it’s something that enables us to do other things. And I think we layer a lot of emotions and feelings about things that have happened to us with money or with our families with money into something that is meant to be a flow state that is meant to move freight money should have movement, money has velocity. And I think just that one simple thing of stop thinking of your money as a pond, to protect at all costs, and start to think of it as a river. That is a huge, huge shift in money mindset of just you know, there is abundance, there is more, there is slow…

Heather Pearce Campbell  10:53

Always moving.

Jill James  10:55

It will continue to move, we need to find purposes for it that have meaning that would I would say is probably the number one thing for most of us is to get out of that money pond mentality into money river, just the simple visualization of that can make a radical difference in how you think about your money. Oh, really. That’s one. I think another is, you have to understand your personal risk tolerance. I personally am off the charts in terms of the risks I’m willing to take. But I also know, kind of, to do research and like where I feel comfortable. Yeah, like I was telling someone this morning, like, I kind of follow Warren Buffett’s investment philosophy, like, I’ve created a position in Roblox because my son is constantly asking for robux. And there are 8 million other kids who are constantly asking for robotics, you know, and a whole bunch of people don’t understand that. And they don’t have kids. And as analysts who don’t have kids, looking at these reports, right, but I see how my kid and his friends are behaving, and I see the money they want to put into it. So I think of like, start to understand something, whether it’s in your business, or how you invest or in real estate or something else, like just pick something that you feel like you know that you spend a lot of time on, that, you know, you understand who the players are, and what the dynamics are, and trust yourself, because you probably know that as well, as someone who’s observing it from a financial abstract perspective, right, you see what’s happening in the world. And that’s one of those places of, you know, pick, you don’t have to be an expert at everything. But understand, like, one, how risky are you willing to be, and to pick a thing that like, excites you, and you want to know more about it, and you’re naturally curious and go with it. Like, again, don’t worry that you’ve picked the wrong thing. There’s plenty for everyone. And I think, you know, we do see a lot of hoarding, and you know, from non regulation in our current economy, there’s plenty of money to solve every problem in the world, there are plenty of materials to solve every problem in the world. But we don’t direct them or we keep them for ourselves. And again, so thinking of that flow state and using your positive energy around something, you’re really going to enjoy engaging with your money, do that, and you know, it will get abundantly easier, right, maybe entrepreneurship isn’t your thing. But you can redirect the money that you’re making from your job into market investments or you know, into a business that you buy, right, you don’t maybe you don’t want to run it. But there are all kinds of ways to participate in the active, you know, in the economy in earning money and profitability, that don’t have to be having a job or starting a business. Lots of it.

Heather Pearce Campbell  13:32

I love that. And a couple things came to mind when you’re talking about that is you don’t have to be an expert at everything, like choose something that you’re familiar with, that you observe, you know, closely or often enough that you feel comfortable with it. Like your Roblox example is a great one. Women are the consumers, women are in it, like we do 80% of the purchasing in our economy, like we we have eyeballs on things. And so it’s such a great point to make, like trust your instincts trust what you’re observing trust, you need to mean when you’re in circles of women that are talking about things like it’s, I love how accessible that makes it feel. And then the other thing just around this concept of flow and money, it’s really fun because my kids are like five and 10 right now and they’re starting to both be very interested in how money works. And so I’m looking for little ways to like teach them things and let them have experiences with their own money and it’s pretty funny because I have to fight against my own training upbringing from my childhood right my son who’s 10 is like he’s a spender he wants to go buy for example all the Roblox things all the Pokeyman things all the you know, little boy gadget I call them gadgets widgets and gadget. Right and it’s it’s all this stuff. And you know, my my daughter, on the other hand is a real saver like we went to the bank for the first time, visit. Please, because COVID I just, we didn’t really go into the bank, I wanted them to kind of have the experience and like know where banks fit. And we’d actually taken some old jewelry of mine and gone to like a coin slash jewelry shop like precious metals. And like we walked out with 400 bucks that went into their savings accounts, you know. And so then we went down to the bank and did all this and Henley had saved like $90 just doing little things, right, you know, like, and I was like, when I counted it, because she’d stuffed it all in this jar, it looked like a bunch of like dirty ones, and a whole bunch of change. It was like, there was 90 bucks in here. My son who was a spender, he said, because I said we’ll eat in we went to spend a little bit of money kind of as, like a fun part of that journey as well. And, and Aiden wanted to spend all of it not the not the full 200. But the the portion that I’d given him for his wallet, and and I was like, well, you’re sure you want to spend all of it. He’s like, Yeah, mom, money’s easy to get. Yeah, and I stopped, I wanted to respond initially with something and and I was like, I love that perspective. So much. I cannot squash that. And I’m like, You’re right, money is easy to get. It’s a flow of energy. And if you know how to do it, and you know how to create value, you can totally get money. But now it’s like, okay, how do we teach them actually to do that, but it’s really, it’s actually so fun to think about from that perspective. I wish that as a kid, I actually had that perspective of like, yeah, money is easy to get, you know, and I want him to keep that because I want him to live in that abundance mindset of creativity and of like, it’s all around us. And how do we tap into it? Anyway, so that was just a fun little side note, but…

Jill James  16:42

It will tell you. So I started with my son, and a $5 allowance, you know, going to the bank and getting a brick of ones is kind of an amusing dance. But you know, I went in and I got $100 in ones and he we set up three jars. And when he was five, you’ve got $5.06 $6.07 $7. Yeah, so we have the three jars. And it says spend saving give, and he has to put $1 into the gift jar. So that both sets aside the effect of taxes. But also like, you know, again, money being a flow state, we don’t hoard it all for ourselves, we have responsibilities, and there are things that we can solve with money. And then he can choose spend or save. Right? So sometimes the spender has, or the Save jar has gone as high as 60 or $70. Because he has a high ticket thing that he really wants. Sometimes it’s like out the door, right? Don’t even give me the cash. Just put it on MY ROBUX account. And I you know, I already know the armor, I’m gonna buy with it. But that’s fine, because then he comes back, you know, three days later, he’s sort of like, Can I get an advance on my allowance? There’s like a physical thing I want or I want this money for this thing at school. And I’m like, No, but I caught him the other day with his entire pokimane binder hiding in his backpack, which you’re not supposed to take to school. And he was like, oh, yeah, I worked out with this other person that I was going to sell them. Like they could pick three of my cards for $5.

Heather Pearce Campbell  18:03

Who like little smarty pants good.

Jill James  18:06

Okay, well looks like you know, break the contraband rules and lose all of our Pokemon cards. But I like where your head is that like you solved the problem. You figured it out, you know, you needed money, and you sell it for it. And this is actually the $5 This kid was gonna pay for these cars. I was like, That’s highway robbery tag.

Heather Pearce Campbell  18:23

Hilarious, it is really fun. When you start to see those little light bulbs turn on my son who’s way into rocks. We had this experience in Montana on a trip where we ran walked past a rock and gem shop. And his eyes lit up when he realized like, there are some people that make a living selling books, you know, it’s one of his passions. And so he literally spent the rest of the trip collecting rocks and trying to sell them out of the lobby of our hotel where we were staying like little sign talking to people, it was the cutest thing. And I was like, Look at this little entrepreneur go. But I love I love those early lessons around like, oh, yeah, starting to understand how money works. And you know, all the concepts. And I think it’s really important and, and sometimes still, as an adult who loves talking about money and loves the concept of money and entrepreneurship. I still find it intimidating to talk about with him because I’m like, I want so much to do it the right way. Right. So there’s all that too. 

Heather Pearce Campbell  19:22

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Heather Pearce Campbell  21:06

Shifting gears into the entrepreneurial space, I think there’s some really important concepts, one of which you just raised, which is about getting your values right from the start so that you are building something in alignment with your values. Can you talk a little bit about that? And what you’ve seen with your clients and sometimes where it goes wrong?

Jill James  21:26

Sure, sure. So one of the ways that we start our engagements to believe we work with the company for six months we do is call the business design bootcamp and from the bottom up, even if you’ve already established your business, we want to know why are you doing this? What do you stand for what’s important to you what’s absolutely out of bounds. And let’s define that from this moment forward. We do business this way. We don’t do business this way. And it can be things like I’ve had people say, like, I don’t ever want employees, right, and we can design for that. Or I you know, I want to be a solopreneur I like this, but I want my income to be this much. Or I had you know a mom who was like I really want to enjoy, you know, I have young children. I want my work week to look like this, right? But I still want to make this much money. And all of these to me are really interesting design questions of what kind of products services teams consult, like, these are just pieces that we move that against solve for? Who do you want to be? What kind of people do you want to work with? What are the values we want to put in the world? What do you want for yourself? These are all valid questions. And then to me, it’s a fun puzzle for my team. And I just say what are the options that we have that would solve for this, that are highly profitable in the market, because you’re a small business, and you have to have highly profitable offerings, right, we don’t compete on price, right? We want to be high value, high cost to execute high price, that is the only sweet spot for a small business. Because you are especially when you’re self funding, you need that profitability to grow, you need to borrow money to pay yourself, all those things should be on the table from day one. So we want to combine both the expectation of being a profitable company with these are the behaviors that are in or out for me. And I think that’s another really big piece, right? A lot of my clients when we go through and start to you know, they do have employees or we talk about benefits programs, the, you know, visors we work with, they’re like this is incredibly generous, right? Or they talk to their lawyer about a policy and they’re like, you don’t have to do this, right? Like, you don’t have to run your business this way. Like this is what the law is. And almost everyone I work with is not saying what’s my minimum requirement under the law, they’re saying, hey, if we’re gonna make money, and these people are putting in the work, like I want to share with them, I want to be fair, right? I want to be aligned, I want us to be able to give back right to the people who are doing this, I’m not looking to exploit their labor, I want them to feel like they are fairly compensated for the work that they’re doing. I wish I had a public option. So we can try some, you know, a different set of benefits. But you know, we will do the best we can with either what’s called a que sera and give them money that they can use to buy their benefits, or actually, you know, if we have the size, offer a corporate benefits program and underwrite it at whatever level we can, and you know, 401 k matching, you know, all of that stuff. What are the ways there are a lot of ways again, this is understanding the money system, there are a lot of things that benefit you while you benefit your employees. And again, there’s a minimum level of that, that are trying to keep people who are doing the minimum from taking advantage, but there’s also a lot of upside in it. So you know, if you have the attitude of I’m designing this business to benefit me because I’m taking the risks, but I’m totally open to sharing with those who are helping me do the work, right. I’m gonna pay my vendors fairly. We’re going to use, you know, ethical and equitable labor, right. I’m going to offer benefits like all of that has to be baked into the design of the business because we need to make sure you can pay for it. You need to know how much you need to sell, you know where your attractive markets are. So you know, we go through this process and really say what kinds of businesses what kinds of products services, pricing will achieve what you want in the world, right. And I let my clients make the call, right, it changes over time, I’ve had people who have said, I never want employees, I want to make this much money. And this is what I want my life to look like. And they start running the business. And they’re like, I would like to hire five people. And I would like the business to be this much bigger. And let’s do that tomorrow. Right, right. And so you know, we have these moments in time as we evolve as entrepreneurs have either, you know, it looks too hard. And then we kind of get on the path with support and are like, Oh, this isn’t as hard as I thought. And this is going okay, like, maybe I should reach for that next thing. And I think that’s a really interesting element of like, working with people over time, as you know, an executive pier, right, as someone who’s it’s their company, they’re the CEO, I’m there to provide options. And also let them know, Hey, if you want to do this, these are the compliance things you have to do, these are the operating things we have to do. These are also some options that become available when you have a business of this size. So you know, kind of that companion person, so that you can stay focused on customers sales, where you want to go owning the vision of the business, and the vigilance that it takes to uphold your critical values, right? Every single person that comes into your business has to be filtered through that, you know, what you’ve written about, like, Is this okay? Is this not okay? It can be, you know, as simple as you know, he used the word scale. And, you know, everybody wants to like, say, I want to scale well, to a lot of people, that means the venture capital playbook, right? Like, throw a lot of money at it, get big, fast, turn and burn employees do whatever you need to do, like, if you say scale in that way, you might be inviting people into your business, we’re bringing in a playbook that you don’t want to follow. And you can’t undo that. So you know, in terms of even knew we were talking about, like your lawyer, your insurance broker, your banker, right, all of these people that you have to ask the questions of, you know, are you supporting me at this level of values alignment, because otherwise, they bring in thinking into your business and advisory that is going to take you out of the this is for us? This is not for us. And that is where you as a CEO end up, you know, with a business where you’re like, this isn’t what I set out to run, like, what what is this company? Like? I don’t feel good about this anymore.

Heather Pearce Campbell  27:30

Yeah. Oh, totally. It’s a couple things that you say that are super important. And the vigilance piece, I think is, you know, high up there. I want to ask them a follow up question on the first you walked us through kind of this process that you do, right, this business design bootcamp that you walk through with your clients, even those who are already established and have some things going, what are some of the aha was that your clients have had in walking through that process? Can you illustrate a few of those?

Jill James  28:02

Sure. I think the number one thing is coming from a finance background, I want to know what your unit economics are. And a lot of the time someone says this is my most popular product, this is my most popular offering. It’s easy to sell. People love it, and we go through it and it’s killing them. They are not making money from it. Right? It just it has a very low margin. And the reason people are saying yes, is it’s underpriced. And they’re offering too much, or you know, the product is too rich. And it’s easy to say yes to and that’s great. But it’s also like if you continue to build your business around that you will not have the money that you need to grow. Right. It’s needs to have massive scale. And so I think that is one of going through, like what do you sell? Now let’s look at the packages, or let’s look at your product lineup. And like what are your margins, and then just having that conversation, the person often will immediately be like, we are never selling one of those again, we are done. I got a contract on my desk, I’m gonna call them and say you can’t have it. Right. Just like in that moment. That is just like, whoo, okay, that is killing me.

Heather Pearce Campbell  29:12

What a surprise to them. Right. Well, and, you know, this highlights the point that it often takes an outside perspective for us to look at the right information and in the right way. Right. And it takes working with somebody who has done this for a lot of businesses before somebody might have that. Aha, like, oh, my gosh, I never saw it like that. 

Jill James  29:35

Yeah, I think that part is really interesting for me, because, again, you know, often we come from marketing or we come from a customer experience. And, you know, we really want you know, thinking of a small business, we want to make people happy, and we just want to work with customers that we like, and you know, we get less concerned about the economics of if our business is functional. And so I think that’s one place where, you know, before we You try to sell more tell her story or other things like foundationally, if your economics are bad, all of these other things that you’re going to do is like you’re selling yourself into a deeper and deeper hole. And so.

Heather Pearce Campbell  30:12

And nobody, we all come out as technicians have a certain expertise, right. And very few of us are trained on the actual economics of running a business.

Jill James  30:23

Yeah, absolutely. I mean, I have an MBA, almost none of what I learned in my MBA is useful here. Actually, the most useful thing was the things I learned as a financial advisor, I bet, because I did look work with a lot of small business owners, and you could see how they were creating wealth and where, you know, where money came from, where profit came from, and how they were running their companies. But all of these, you know, all my formal education and my bigger jobs, no, not useful, like useful, tiny bits of the moments, concepts, you know, again, knowing you know, how these things work, you know, those things are useful, I think, in context. But, you know, really the day to day, there isn’t a playbook for how to run a small business that you fund, you know, again, using sales using debt, you know, your some of your own money, other people’s money. I mean, I think these things are relatively simple, but it’s hard to find the right information and support for the level that you’re at, to help you move through these stages. Right. There’s a lot of help when you’re under $50,000. And there’s a lot of help when you’re over a million dollars. And in between, not a lot.

Heather Pearce Campbell  31:31

Yeah. Well, and you said something before we went live that really stood out to me that and I think it was you can correct it if I say it wrong, but there is no such thing as a simple small business. 

Jill James  31:43

Right, where you go into that door. So I think, you know, all of us being remote and having again, 10 million businesses started during the pandemic, we were fully remote. A lot of people, you know, kind of, there wasn’t a lot of vigilance around, like, where are you? What does that mean, you know, understanding from a tax perspective and a liability perspective, like, where are you physically located? Right, we’re just doing the work wherever we could, and it was kind of like, let it go.

Heather Pearce Campbell  32:10

Because so many of the folks you and I work with are not location specific, right in the delivery of their work. And so people tend to think like, oh, I can set up sub shop virtually and be anywhere.

Jill James  32:23

Right. Right. So I think where, you know, I have complicated things like, you know, I have one business with five employees, and all five of them are in different states. And the business that they operate is on three continents. Yeah.

Heather Pearce Campbell  32:39

That is not

Jill James  32:41

That’s three kinds of lawyers, right? Do we have to pay VAT? And do we have to pay sales tax? And what states? Do we have to be registered in? And are we paying the proper tax authorities? Right, and, you know, my client is just like, I just want to, you know, run my business, I want to go to Canada and you know, do this thing that we all want to do, right? And in the background, it’s just like, okay, registrations and how are we going to account for the money? And where are we going to pay taxes? And, you know, basically, my job becomes how do you not get in trouble? How do I facilitate you continuing the joy of working with these people that you love, we’re in five different states, and being able to, like, go to London or Cannes or Toronto, or wherever you want, and like, you know, your events in California even write and say, Hey, pause for a second, here are a couple things we’re going to need to work through on the back end, before you commit to this location, or before you commit to this hire. Like, it can’t happen overnight. We’re gonna need a two or three week window to get this right. Right to like, just figure out like, what’s our game plan here? Do we need a tax reserve? Do we need filings? You know, are we already in trouble if you go ahead and book this venue and start selling tickets there before we put any of this in place? Right. So I think there are things like that, that because we’ve been able to move around the world so easily. You know, I lived remotely in Spain for a year and I had clients even though I told them that it never clicked for them, that I was not in the United States. So you know, I think people are just like, you’re on Zoom. It’s light outside. Right? So I think there are like, we don’t think about this, that we don’t come from this world. And it is, you know, quickly very complicated to hire people and sell things in multiple states and sell things on the internet as you start to make more than $100,000 that, you know, it’s the experts again, that you need, I think, you know, this is one of the things of like, you need the skills and the alignment with the people who can give you this kind of advice. So you know, this is I function in this role as a team captain in a lot of my clients worlds where they’re like, just Okay, tell me but then take care of it. Please assemble the team of people and manage them that are going to take care of this for me and tell me how much it’s going to cost and please keep me out of trouble because cuz I just, I just want to run this company, like, I want to do the part that I’m good at. And then I like, I did not sign up for all this right? And so you know, and you know, this is you can be a one person business and still have all of these complications, right? So I think, you know, this is often we do it, and then we get in trouble, right, and then we get the scary letter. And then we, you know, really, really back off, maybe figure out the systems, the things we need to put in place, just, you know, sort of like a pause to say, Hey, I know, there’s probably a checklist of questions I should ask here, who is the person that I talked to about? And so, you know, that’s, you know, where, you know, you and I will, you know, jump in, you’ve jumped in with clients of mine before where we’ve talked about like, Okay, you’re gonna take this out to market, there’s producible, IP protections here, you need different agreements on your website, you can’t charge for that without saying this thing, right, you know, just kind of these operational steps, that again, we kind of gloss over, because it’s easy to say, I put this on the internet, you can buy it, and I can process your credit card. Hey, I’m in business, right? And then, you know, now that tax authorities and other things are so digitized. The second that something hits an account, you know, MasterCard has to send a report, you know, in the backend, what’s happening to the federal government, and then you get that letter, no one says to you, hey, let’s take a minute, you seem new here, let’s just give you the benefit of the doubt and like walk you through how this works. That does not exist, you just get a letter from the IRS or a state tax authority or, you know, an agency that’s like…

Heather Pearce Campbell  36:39

A foreign tax authority, because eyeballs are not on those foreign transfers and foreign payments. They absolutely are. And depending on amounts, you might have numerous eyeballs on those transactions. And so it is I’ve said for years, like the pace of business, generally, as it evolves, has been much faster than the pace of regulations to catch up with business. But we’re in an era where things are catching up with people. And you know, especially as more and more businesses live in the digital space, as tax authorities begin to be aware of the way businesses operate. Like, there are very few ways you can escape those eyeballs and escape those requirements to kind of catch up and play with the rules. And, you know, you’ve worked with clients, I’ve worked with clients that, that midway through the pandemic are like, Oh, we’ve had employees move different states and unit I mean, just kept them on payroll and and suddenly they’re having whole new states to file and reincorporate in, you know, do a foreign incorporation, you know, catch up with all of the regulatory issues that come along with it. And it’s not hard, but it does take some time and a little effort to like, go through the steps, right. And it just for me, it just underscores the importance of working with the right people in your business. Right. And I know one of the things you had mentioned is the importance of and especially for folks that come from the consulting world, skipping the part of the process, where you just grunt it out yourself and do all of this, you know, we’ll just call it toiling, for lack of a better word for several years on your own. Like, you don’t have to do that there is a different path.

Jill James  38:24

Absolutely, absolutely, especially I think you and I were talking about yet study from a couple of months ago that just again, showed the velocity of women and people from historically marginalized backgrounds, leaving the corporate world for entrepreneurship, well, you’re probably mid senior, you probably had a team of people around you, I bet you weren’t doing the p&l for your own business. Nor do you know how that works. Like, you could have been running a business unit, and I have no idea how to run a business, right? Because when you take on that CEO, mantle, founder and CEO, one, if you’re an LLC, or an S corp, it’s your personal credit, you is your faith and credit, right, like we just went through the debt ceiling thing, you are the full faith and credit of your business. So, you know, even though you’ve established a business, it’s you. And so understanding, you know, what that means for you financially with the risks are other things. And then also, you know, you don’t have that built in group of people who are experts and have been hired to function at a certain level. But also you’re not doing accrual accounting for a fortune 500 company, right? Like we need to get you the right people who understand the business that you’re in. And a lot of times the number one thing that I see people run into is they were w two employees, they call up their tax account and they say, Oh, hey, I started a business and they’re like, Okay, great, what a side hustle or whatever. And then they come in and they’ve sold like 234 $100,000 worth of stuff. And the accountant is like, you didn’t tell me you started a business business right the like, what did you think I was like, you know, selling repotted flowers out of my basement on the weekends. Like, you know, I was a CEO or I was a senior exec I get it over this big company like I started a legit business. And you know, it’s not that person who is your w two accountant is probably not the right accountant for your business. You’re they’re not giving you the right advice. But people just say here you are my accountant, you are an advice giver. Right? And there are whole classes of professionals that don’t want to touch advice, like, Right? Talk to a lot of lawyers where they talk about, there’s, you know, advice and counsel, and then there’s litigation, right. And nobody wants to be in the advice and counsel business because it’s it’s risky, right? It takes on a different level of insurance. And you know that. So for anyone, like an expectation that any professional will give you advice as a baked in part of their fee, and their job is not guaranteed, you have to say, hey, I want you to be on my team. I’m looking for somebody who’s going to get on calls, who’s going to give me advice, who’s going to give me feedback, right? I need to talk to you more than twice a year. Right? I need to I need to know, I can call you with these questions. And I think there’s an assumption for many of us have, like these high level, you know, people that we’ve been working with can just shift gears and understand the business that we’re in now. And that’s not how the practices are built.

Heather Pearce Campbell  41:13

No. And you highlight a really important point, which is that even within the world of a specialty, let’s call it accounting or tax prep or whatever, right? You’re working with a CPA or an accountant. And people just think like, yeah, this just makes sense to continue even financial planning, right? Look at your health needs, how many times have you had to switch practitioners or seek out a specialist because you’ve got a particular thing that you know, this other person can’t solve. It’s that way in other fields of advice and consulting as well, even within quote, unquote, the business world of legal business law. And what somebody does in one business law practice can be very, very different than somebody else, also in a business law practice, right. And so it often, like I tell people, it may take a little extra effort at the beginning to develop the right team and connect with the right people. But it’s so worth walking the steps to get the right one at the start, so that you’re not having to switch gears, you’re not having to like, oh, I relied on bad advice that really wasn’t a fit for me. And that screwed me up in this way. And I’ve seen that so many times, whether it’s clients that spoke to a CPA that was not strategic, they were more like backwards looking, and just documenting what’s already happened. Not helpful. If you’re a small business, and you are, you know, planning some level of growth and scaling. You need somebody who’s very strategic and knows exactly where you’re headed and help walk other people are on that path. Same with law, right?

Jill James  42:44

The advice for this, the place that you’re in, in your business is super, super important. And those people might not be with you forever, but you need the person that matches the phase that you’re in, I know, I say to my clients, like, you’re probably going to get into the ones that you know, really want to grow and like you’re gonna get between 10 and $15 million, and I’m not going to be the right person for you anymore. Right? Like, we may have gone from $250,000 to 10 million together. But when you want to go past this, there is again, a different set of tools, a different set of knowledge that you’re going to need, and we’re going to start to clash because you’re going to want me to give you more complex advice, and that’s not my area of expertise. So I think, you know, knowing also, what’s your lane, what area do you want to be in, and there are different specialists for for different times in your in your corporate life. You know, but I’m sure you have, and I have as well, like, you know, I cultivate relationships with people that I know, are running their businesses in the way that support other businesses that, you know, I’m taking on as clients. So you know, I naturally put a team of people in place, right, I functionally, as a business manager will say, here are two or three accounts, I know they will all work for you, let’s figure out which one you like. But all of them can meet your values, all of them are aligned with you, and all of them, you know, have great skills. And so you know, it’s the same thing. Oh, so once you tap into, and I think this is again, where the vigilance comes in, if you are tapping into people in your professional advisory capacity, who aren’t cultivating networks of people who do not share your values that will only amplify over time, because they are working together in a way that they are used to working, and they will bring that into your business and they will bring other people into your business who work that way. So you know, this is a place where again, there’s asking the skills questions, right, but do you work with businesses that are like mine? This is my intention for where I want my business to go. And that part’s really important to me, right? I mean, I you know, put on one of my recent you know, hydrogen UVA and I put on a lot of things like we work with a lot of gender non binary people, we work with a lot of creative people. We have people that have pronouns that you might not be used to using. This cannot freak you out. You need this is this is a part of how We function and we expect you to deal with us, right? This is the world, this is the world we work in. And I think that’s fair task of not just be like, you know, I hear all the time that like, oh, but they’re really good. Alright, but they might not be really good for you. And I think this is again a place where if you are trying to intentionally put a purpose driven business that is aligned to who you want to be in the world, and what you want to put into the world, this is the vigilance it takes to ask the hard questions of who are you as a person? What are your values? And can you give me great advice that fits the face of business that I met? 

Heather Pearce Campbell  45:37

Totally, it’s such a powerful question, you know, who else do you support that has businesses like mine, or you know, is this the area because you don’t want somebody who just dabbles in this has like, you want this to be like the primary type of business that they support, they know where you’re headed, they can support you right now. I mean, like you said, sometimes you might outgrow your, your professional team or need to, you know, get a new person for whatever reason. But not only is it important to know where you are right now, but where you’re headed, because you want those people to help you get there. So I know we’ve covered a lot out of respect for our time. I mean, we’ve talked about scaling we and what that means we’ve talked we’ve talked about really being clear on your values from the start, and the vigilance that it takes to really stick to that path, the importance of surrounding yourself with good team and you know, good advisors that will help make that easier. I know, there’s so much more that you cover that you work with, you know, for your own clients, for folks that are listening in that are like, gosh, I need to go connect with Jill, follow her on socials. Learn more from her hear more about how she works. Where do you like to send folks?

Jill James  46:51

Sure, well, our website is That’s a great place to start. It’s got some videos and more about how we work. We also have a blog. So you know, there might be some topics in there, I particularly write about things that again, as a founder, who is becoming a CEO, learning to be a CEO, what are some of those transition points? And how do you shift from thinking like an employee to thinking like a business owner. So there are a lot of tools in there that are written specifically for you as the self funded business owner who wants to be purpose driven, and is moving into ownership of you know, I am leading a business that I believe in. So that’s great. And we also set up I have a list and I write a weekly newsletter. And we also do an AMA every month where I just take questions. And you know, I know you do this as well.

Heather Pearce Campbell  47:40

And, yeah, for people who are wondering what that means. It’s an Ask Me Anything session. So I love that.

Jill James  47:47

Yeah. So I write the weekly newsletter really, again, from the point of view of things that you know, for this business owner are like, what is the world look like? What are technical things you need to know? What are trends we see happening that are useful for you different different technologies, or just to help you run your business better, and we set up a special URL so that we know you’ve come from Heather’s podcast, it’s So if you sign up for my list at, we’ll send you send you a special bonus for listening to.

Heather Pearce Campbell  48:22

I love it. Well, we will definitely share that link. Anything else that you want us to share? Do you show up on socials? Where do you like to connect with people who?

Jill James  48:30

Yes, so I regularly post on Instagram. And on LinkedIn, those are my two primaries. We do a lot of LinkedIn posting, we may repost a, you know, we have a YouTube channel, sometimes pieces from the AMA, or other short videos that we create, will put on YouTube, but we always put them on all the other channels as well on. Yeah, so I would say you know, if you are you following us on Instagram or LinkedIn, you’re gonna get all the good stuff in one place or another.

Heather Pearce Campbell  49:01

Oh, I love it. We will share all the links to socials will include your YouTube as well. I love YouTube, especially for like that content where somebody wants a library of it, right? They just want to see it all. What final either action step takeaway would you like to leave listeners with today?

Jill James  49:18

I would say, you know, I know there are a lot of people are saying like, Can I do this? Like, should I leave the job? Should I start the company. And if again, it may not just be a financial motivation, it may be to be the person I want to be in the world. I cannot be in this environment every day. That is a perfectly reasonable reason to start a business or buy a business that you’re going to run. So you know, it’s again, creating the world as you want to see it. You have so much more ability to do that. When you control the work that you do every day where your time goes and where your effort goes. You know, you’re always if you’re not feeling right in a corporate space So, just start, right, figure it out, get some runway, get a team of advisors together, reach out to people like me, I have, you know, free 20 minute session on my website, you know, reach out to people and use the resources that you have. And just ask questions like, gather everything that you can, and the minute that you feel a teeny bit ready, go for it.

Heather Pearce Campbell  50:20

I love that so much, I’m going to refer back to your new word, the general fed up witness that people feel about things like take that as a sign. Also, if you’re reaching that kind of fed up at this level, even in your current business, right, I’m gonna invite those people to also get help reevaluating what they’re doing and how they structured things, because there’s likely just an improved way of doing it, that would help you get a lot more enjoyment out of probably what you originally enjoyed about your business in the first place.

Jill James  50:54

Absolutely, and often it is two to three things that are not hard, but they have to be done in the right order. And we have to do them really intentionally. So identifying what those things are to get you back on track. And that certainly, you know, again, if you’re if you’re feeling like this has gotten too hard, or I feel really stuck, it’s a good moment to you know, a course, coach may not do that for you, like we really have to dig in and dig into your business and look at what’s happening both financially and qualitatively. If you know what you need to talk to you about your life and what’s going on and how your business is functioning. We have to look at both sides of it. And I know I’m a numbers person. And of course, I’m gonna look at your financials and, you know, look at all those things. But it’s a balance of what’s like, where do you want to go? And what are our options? And that’s always something that’s available to you.

Heather Pearce Campbell  51:47

Yeah, I love that. And I love that you mentioned you’ve got that 20 minute call. So folks, if you’re listening, pop over to the show notes page find Jill James’ episode, and this is episode two. So I will share also the link to the original episode, plus all the resources you’ve mentioned today. So I so appreciate you. I love the work that you do. I’ve so enjoyed being connected to you over the years and I’m really grateful that you came back on today. 

Jill James  52:15

Yeah, thank you for having me. I am always so happy to talk to you. We can go on for hours right the epic eight hour podcast one of these.

Heather Pearce Campbell  52:22

I know maybe maybe that’s the thing. Hilarious. All right. Well deal. We will see you again very soon. Thank you. 

Jill James  52:31

Thanks Heather.

GGGB Outro  52:33

Thank you for joining us today on the Guts, Grit and Great Business® podcast. We hope that we’ve added a little fuel to your tank, some coffee to your cup and pep in your step to keep you moving forward in your own great adventures. For key takeaways, links to any resources mentioned in today’s show and more, see the show notes which can be found at Be sure to subscribe to the podcast and if you enjoyed today’s conversation, please give us some stars and a review on Apple podcasts, Spotify or wherever you get your podcast so others will find us too. Keep up the great work you are doing in the world and we’ll see you next week.