“Call Me CEO” is your master-class on innovation, creativity, leadership, and finding YOUR perfect balance between motherhood and entrepreneurship.

Have you ever wondered what strategies you can use to level up and scale your business? In this episode, Camille welcomes Jill James, the founder and CEO of The Jill James.  She helps transform self-funded companies into high-growth businesses by helping the founders design and implement their strategic operations based on their visions for their company to avoid burnout.

As an entrepreneur, if you want your business to grow, you have to accept that you’re going to keep walking up to those limits and figuring out how to move to the next level.

— Jill James

Jill shares her journey from moving from a small town in Wisconsin to working on Wall Street and now, running her own business. She gives step-by-step strategies that can help you expand your business, including tips on how to do pricing, task delegation, branding, and building a successful pipeline. She also talks about how important it is to go out of your comfort zone and some resources that you can use to learn more about business growth. 

Look for those kinds of things where it’s highly informational, has lots of support for you as an entrepreneur, and is positive. Find something that you can do until you get to the level that opens the door that you’re truly ready for that growth. You’re ready to go and commit because if you want to level up, you’ve got to be completely all in.

— Jill James

If you’re still at the early stages of your business or are looking for ways to further expand, tune in to this episode to learn different step-by-step strategies that you can use to make your business grow and work more efficiently so that you can avoid burnout.

You’ve got to get a little bit out of your comfort zone and learn to live in that space just a little beyond where you want to go, and that’s where growth comes.

— Jill James


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I think just being honest with yourself about what's going on, why is this scary, what are you afraid could happen, and putting it out there, and then sometimes, just saying it is like, "Oh, you know what? It's not as scary as I thought it was."



So, you want to make an impact. You're thinking about starting a business sharing your voice? How do women do it that handle motherhood, family, and still chase after those dreams? We'll listen each week as we dive into the stories of women who know. This is Call Me CEO.


CAMILLE [0:40]

In this episode, you're going to be hearing a lot about strategy and what to do when you think you are ready to level up your business, but you're not quite sure how to do that. So, as we go into the episode, I first want you to think about creating space for your dharma. What is dharma? I've been listening to a book called Think Link a Monk by Jay Shetty. And there's this part that I specifically wanted to zone in on where he talks about thinking about your interests in four quadrants.

The first quadrant is something that you're good at, but you hate doing it. He said a lot of times, people get stuck in jobs like this because you're good at it. You know what to do. You're efficient at it, but you hate it. Okay. We don't want to live there. Number two is something that you're good at that you love. You have a passion for it. It's so fun for you. This is where you want to live. Quadrant number three is something that you're bad at, but you love. This is something that you may not be the best, but you love learning about it and there is something in you that just keeps pulling you to want to learn more. Fantastic. And the fourth quadrant is something that you're bad at and you hate it.

And I can tell you with each and every business owner that I've spoken with, there is something in that quadrant that they're bad at and they hate doing. And, for whatever reason, they hold onto that responsibility of that item for far too long. In this episode, I want you to think about that quadrant and think about what you can systematize or move off your plate onto someone else's plate that's much better at that thing than you are, so that you can live in quadrant two of something you're good at and something you love.

Welcome back everyone to another episode of Call Me CEO. This is your host, Camille Walker. And today, we are talking with Jill James, the owner, entrepreneur, and creator of The Jill James, which is a powerhouse that helps you go from a founder to a CEO of your own massively successful company. Now, what I love about Jill is that her approach isn't a one size fits all. It's more about tailoring your approach, so that it fits into your life. And you know that I'm all about that because we celebrate different stories each week as we talk to different founders, owners, and CEOs. So, Jill, thank you so much for being here with us today.

JILL [3:07]

Thanks for having me, Camille.

CAMILLE [3:08]

You're very welcome. I love so much from your bio that you came from a small town of Wisconsin all the way to Wall Street, and now developing your own business. And I'm thinking, "A book titled Wisconsin to Wall Street, that was a cool play on words." Tell us about how you got started and how you went from a small-town girl to then now creating a massively successful business.

JILL [3:32]

Sure. So, I'm originally from a town of about 1,000 people in Central Wisconsin, but I feel lucky in that both sets of my grandparents had small businesses. So, I grew up working in one grandparent's general store, making Cherry Coke, stocking the candy canes, making change in the old-fashioned cash register. From the time I was five or six years old, I would go stay for a couple weeks and actually work in the store and I thought it was amazing. It was so much fun.

So, I've always had family that has had businesses. One of my aunts had a dress shop for a while. My other grandparents had a freight and trucking business. So, lots of different kinds of businesses. I've always been a natural student, so I have asked a lot of questions about how does this work? What do you do? So, I think that carried over across everything that I do is I just like to learn about how things work. I’m not a manual how things work. I can't fix anything that's physical. But if you give me a concept, I can figure out how to make it work.

So, in thinking about that, I didn't really know what I wanted to do. But there were only a couple of jobs available in my small town and I knew that wasn't what I wanted to do. So, I got lucky and oddly enough at a 4-H Fashion Revue, I had made some clothes for myself and I got sent to the Wisconsin State Fair. And a couple of the other girls there in the Fashion Revue had a Harvard Fletcher shirt. And I was like, "Oh, did you get that at this local chain store?" which was super popular to have Harvard Fletcher and they're like, "No, I’m actually going to Harvard." And I was like, "How did you do that?"

And they explained to me how college admissions worked and that I should really aim higher and see what I could get because not a lot of people from smaller towns apply to elite colleges. So, I started throwing some applications and I got into the University of Chicago and decided to go. And I think that was a big gamechanger for me because I just didn't understand the possibilities of the world until I got there. And also, that I could compete with people who had gone to prep school and people who had had a different kind of educational background than I did and it was really just a level playing field of people who liked to learn and wanted to try different subjects. So, I don’t think I would have ever ended up on Wall Street if not for the recruiting program there.

One of my friends, I was like, "I don’t know what I want to do." She's like, "Throw in some resumes. See who picks you." It was a really good year. So, I happened to get an offer from JP Morgan when it was just a standalone investment bank before it was part of Chase and I decided that was the most interesting job. So, I took it and I moved out to New York and I worked in the bank for a little over a year and got the gist of how big companies worked. And there was a dot-com boom that's going on at the time. And so, I jumped ship and was like, "I don't want to wait 10 years to be able to do something interesting. I want to do it now."

So, I worked at a startup for a while and we got acquired, which is amazing. But then, the dot-com bust happened and then I went back to finance. So, the progression of this is I've gone from finance to tech to finance to tech until the point that I started my company in 2015. And I did that. I was the COO of a venture-backed company and I was flying out to Dallas every other week and negotiating our deal. And I should have realized this before, I was seven months pregnant, but I realized that seven months pregnant, it was not going to work in the long-term for me to have that job.

So, the best option was I had a couple of people who had said, "Hey, if you ever want to do this for me, I wouldn't want it full-time, but if you want to, you could work for me and be my fractional COO." And that's how my company started. And so, for years, I had tried to think of that big idea that would get me venture and be the billion-dollar company and I just never really had that idea. And then, ultimately what it came down to was I started this services business at seven months pregnant because I had a client and that was what I could do. And so, that's how this company started. And I had my baby and my company at the same time. I always call them my twins because everything in my business has been designed around my funds needs up until the point he went to kindergarten.

CAMILLE [7:44]

Oh my goodness. First of all, there's so much for me to chew on that I'm like, "Yes, yes, yes." Just those little bits of opportunity where meeting those girls at a 4-H Fashion show at a state fair, like what? How does that happen? And then, I think there's a lot of lessons in that in taking opportunities that may not seem like they would be so transformative, and then also where your friend said, "Just throw it out there. See what's available. Put your resumes out there. See who latches on."

I think that you've been able to teach so many life lessons just in that scope of time that you just shared with us that a lot of times, it's about taking what's available. And with this business, "Okay. I have someone who wants to pay me for what I know what to do. What if I lean into that and what happens?" What a powerful experience.

Now, for those of you who are listening like me who are thinking, a fractional COO, does that mean that you're doing operations? Does that mean that you are helping them with strategy? Talk us through that a little bit, so that we can understand at a larger scale what then your business turned into.

JILL [8:50]

Sure. So, when I started, I basically was doing the job that I had been doing for my last two or three years, partnering with the founder and figuring out how to operationalize their vision. So, the founder would say, "This is where I want to go." They were really focused on customer, maybe on product. But running the business was not a thing that was in their wheelhouse and I really liked to run businesses. I like finance. I like personal wealth. I like operations. I don't like HR, but I'm good at it. So, all of those things that there's six or seven buckets that fall into operations in most small companies and I had exposure and have done a number of those jobs.

So, being able to step into a small company and say, "Okay. We're going to put your systems and your finances and how you hire people and your agreements and your legal, we're going to whip that all to shape. And then, we're going to be able to make it repeatable, so that you don’t have to think about whether or not those things are working for you."

Because I think those are the things that for a lot of founders, they don't know what they don't know and it's really scary. I've had people call me the person who makes sure I don't go to jail. It's unknowing mistakes that you could make that could actually lead to some serious trouble. There are just rules you have to follow. And I think when we're new founders and we're trying to make our way, sometimes there isn't a set way to learn that and often we learn through trial and error until the errors are painful and expensive.

So, my focus has really become I started out doing the fractional work where I could only work with two or three companies at a time. And after a couple of years of that, I really saw that most of the founders I was working with had this common problem of they were not business operators nor should they be business operators. There was some stuff that they had to learn as CEOs to be good operators and to help make decisions, but that wasn't going to be their day-to-day job and it wasn't right for it to be their day-to-day job.

So, for them to grow, we had to keep them out of the day-to-day operations, make that my job and my team's job, and set them free to work on their zone of genius, which is customer, sales, revenue, product, building that vision for the company, leading the company. And so, I hear from a lot of people, "I don't think I should be a CEO because I don't know this stuff." Most CEOs have a layer of stuff that they know, but they leave it somebody like me to actually do it and make sure that's in front of them at the right time.

So, the way that my business has changed, I'm now six years in, the way that it's changed over the past four years is I've moved much more into being designing people's businesses of thinking about what do you want to be as a CEO? What's your purpose for this business? What do you want to put in the world? And then, we design the business to be profitable for a staffing plan, a budget, and then the kinds of operational things we need to do that actually move the business toward where they want to go. So, I start with the business design process, and then I help the founder implement for at least six months, which is typically where we start.

CAMILLE [11:58]

Wow. I know from experience in many interviews that I've done that that is a big pain point for a lot of entrepreneurs because a lot of times, entrepreneurs are more visionary and are more into the process of the vision, not so much the step-by-step minutia, like you said, the HR and the hiring and the books. So, what would your suggestion be for someone, say, who's been in business for five years and they're ready to hire out more, perhaps they're ready to create more of a vision? What would be a common question that people would come to you with and what would be maybe the first steps to take with taking a small company into something bigger?

JILL [12:45]

I think the first thing that we really talk about is that what is your role as CEO? So, who do you want to be to the company? What kinds of things do you love to do? What kinds of things do you hate to do? I have my clients do this love hate exercise where we want to skew their job to things that they love and we want to quickly take off the plate the things that they hate because it just drags down your energy when you're constantly pulled into those things that you truly deeply dislike. There are some things that we can tolerate, but everybody has a hate list. And I think it's okay to embrace the hate list and get that off your plate. That's a top delegation priority because it will drag you down. That's an obvious place to make some investments and get that moved off your plate. So, that's the work part of it.

And then, it's also, what's your vision? What's your purpose for the company? Why are you doing this? What do you want for the people who work here? What do you want for your customers? What does this do in the broader world? Most of my clients have some purpose that they want to put in the world through their work, some change that they want to make. And so, we want to make sure that always stays in the forefront as a pillar of how we make decisions of, does this serve the customer? Does this serve our purpose? And if it doesn't, that helps us make decisions about things that can fall away because they might be things that a lot of companies do, but they're not right for us.

And then, the last piece of it, I ask a lot of questions about personal finance. I jumped over this part, but I was a personal financial adviser for a couple of years when I lived in New York. And so, by being an owner of a self-funded small business, there's a different world of opportunities available to you in terms of how you pay yourself, opportunities for wealth-building, opportunities for building the value of the company, if it's something you think you want to sell down the line. So, how do we make sure that you are being compensated and getting to your personal goals while you put all this good in the world?

So, it's a balance to me of you have to get paid from the beginning to make a real business if you're self-funded. So, how do we make that happen? So, that's a big piece of the first part, and then we actually go into the unit economics of the business and what activities are we doing that are not profitable that we should stop doing? How can we repackage what we do to do the most profitable things that are most valuable to our customers? Because that's the best zone for a sustainable small business. You want to do things that are hard for big companies to do that you can make a lot of money at.

CAMILLE [15:15]

When you're presenting these questions, how long would you say it typically takes for someone to get through that process of going through questions and finding answers that help them to move that needle and that accountability to move forward?

JILL [15:32]

Once people are ready to start, I do this in a free session where we focus on the you in the business design and it's just a lot of talking in the first two hours. Typically, within the first two hours or about a week of thinking about it, when you ask the questions a certain way, people are like, "You know what? This is why I'm doing this. This is meaningful to me. These are my non-negotiables. I know what I love and hate." When you ask questions that are sharp like that, we cut out the middle. You know what you love to do. You know what really bugs you. So, that helps us get more focused on things you can clearly answer with conviction right off the top.

If you're in your business every day, a lot of these things are things that you know. It's just that nobody is asking you these questions. So, I find that when we ask the questions in terms of what you are doing, why you're doing it, what your vision is for it, what you want to make, and being given the freedom to say, "This is my ambition for this." It's okay to say, "I want to make money for my business." It's okay to say, "I want my business to be this big." When I'm sitting with someone who can say, "Okay. This is the path to how we get there." And I think that takes out some of the scariness of when we can put together some stepping stones of this is how this will look in six months, in 12 months, in 24 months, if we do these things in this order. All of a sudden, it doesn't seem so unachievable or this chaotic stoop that you have to wade through to figure out, grab things out of the bucket as you go. There's actually a path and a progress for you is, "We're going to do this first, second, third."

You have somebody to ask who knows the answer to most of the questions or is going to put you in touch with the right referrals of people who align with you and can do the work. I think that makes things a lot easier because we spend a lot of time thinking about, how am I going to solve this problem or who could I ask? And then, we boil the ocean by interviewing six or 10 people and trying to decide who's going to be the right fit and it just creates a lot of paralysis. So, I try to boil everything down to one or two people who are a good fit and do that work without bringing it to the CEO. So, I think that's really helpful. If you have a narrower set of things to choose from, it really helps you make a decision.

CAMILLE [17:58]

Yeah, for sure. Now, when you started this business and obviously, you have so much experience that led up to this place of you creating this business for yourself, how did your business go from there and what was the best thing you did to grow your business from that one first client to now the many?

JILL [18:20]

I think the best thing I did was move away from hourly billing. It just didn't feel aligned with what I wanted to do for the client and then I wasn't getting any information I needed because every time they went to call me, they're like, "Is she going to charge me for 15 minutes? What's happening?" I need a steady flow. I need a steady diet of information about everything going on with you and no hesitation to share it, no hesitation to say, "You know what? Let me send this to her and let me not try to figure this out. Let me just send it to her and ask the question."

So, when I moved from a pure consulting model that was by hour, things like that, to set packages for periods of time with scope of work. I think that was a big change in my business because it shifted from, "I'm just a day-to-day person and really have to think about it every time we want to ask her something" to "This is my partner for this long. I've committed to it. She's going to help me and we're going to go from here to here in this period.: And I think that's made a huge difference. It also helps me spend less time on marketing and promotions and finding that next client, so that I can really do deeper work with my client.

CAMILLE [19:31]

How were you able to set your pricing and was that difficult for you?

JILL [19:34]

It's always a dance on pricing because this is what I do. I have some analytic tools that I can use, but one thing that's been really helpful for me that I carried over from when I was doing hourly billing is I still keep a time record. I still use Harvest and I have it in my calendar. And I keep track of everything that I do whether it's for business development or internal management or working on a client. And I have it broken up into whether I'm having meetings or I'm doing work. In that way, periodically I can look back, I can say, "How much time am I actually spending on this and what did I do?"

If I'm finding that this client has stepped up a level, their business has grown. We're doing more sophisticated things, then I can create a different tier of, "Hey. You're a little bigger. We're doing different stuff here. Your monthly retainer or your six-month retainer is going to go to this price." And so, it just keeps me honest of not overdelivering and also looking at how much time does this actually take me or where can I delegate something that would keep the price sustained? I don't need to be the person doing that. So, I find that that time tracking both a discipline of keeping track of what I'm doing and then having a record to look back is really, really helpful for pricing and for structuring my work.

CAMILLE [20:59]

I really like that. I have a coaching business that I've created, a virtual assistant course for women to start businesses and work from home, and it's always this debate of is it hourly? Is it package? Or how do I put that together? I really like how you said that, how you stay accountable to what you're offering, but it's also you can keep track of that time valuing that time and exactly knowing what that looks like, but also to be totally invested, so that you're not going back and forth and thinking, "Oh, that was a 15-minute phone call, now what?"

Because that's true. I have had time where I have thought that before in a situation where I was talking to someone and I thought, "Oh, man. We just chatted for 20 minutes on DMs. Was I getting charged for that?" That's a thing, so you have a team now. How long did it take you to go from yourself to now a team and how did you introduce those key players in your own business?

JILL [22:01]

It's been gradual. I think the most important thing is adding a virtual assistant who's an executive assistant. And I still use a lot of consultants, so I haven't had any permanent W-2 employees yet. That's something that's coming up for me. So, if you really love modelling and finance out there and you like small businesses, I will have a job posting coming up in the next couple of months.

CAMILLE [22:24]

Did you say modeling and finance? Two separate jobs or maybe a really good-looking accountant.

JILL [22:32]

Modelling is when we build how the business works.

CAMILLE [22:34]

Okay. You're not talking for products.

JILL [22:38]

No. I'm out in L.A., so people tend to be very pretty here. But yeah, it's a financial skill to be able to model out the cash flow in a business.

CAMILLE [22:46]

Got it. Okay. Now, I know what you're saying. Oh, that's so funny.

JILL [22:52]

Yes. No, we are completely EOE here. We'll not judge people on their looks. So, yeah, from that perspective, I think the first thing was just some of the day-to-day management. Being in your email all the time is a time killer. So, my VA checks once an hour. Is there anything critical? Is there anything action-oriented that needs to come to my attention? What can she take care of? Any bookings, things like that, I've tried to use more standard operating procedures.

In fact, just this morning, I redid my standard proposal, so that all the pricing is up to date and it's standardized and we're just dropping two things and we can get it out the door. So, there are things like that of trying to do the most with the people that you have. We use a lot of Loom videos. As I do it, I make a recording, hand it off or we go person to person and just show how you did it, so that we have that guide. So, I found that's really helpful, but yeah, definitely the first thing is a VA, even if it's just 10 hours a month or a couple of hours a week just to be able to hand something off. Learning that delegation and getting those important, but low-value tasks off your plate, I think that's a great place to start.

And then, beyond that, I think there are times probably when you have to think about, do I need this person forever or do I need this person seasonally or what do I need? So, there have been times that I use a personal assistant, a PA. Sometimes, there's stuff in my life that I need taken care of, so I can spend time on work. So, I'm terrible at opening physical mail. It's like go through the mail pile, scan it, put it in my drop box, all the way to running pickup on a Target order that I put in. You can still do the ordering if you want, but send someone else to pick it up and bring it to you.

So, sometimes it might be something personal in your life. Like a couple years ago, my son's school ended at 3:30, I needed the full day to work until 6, so I hired someone to be a nanny for him just from 3 to 6 every day. And she would pick him up, bring him home, and they'd have a good time for a couple hours until I was done with work.

So, there are all different ways it can look in your team to make it work for you, both to create the space that you need to do the work and grow your company. It might be something with your family or things that you take care of in your home. It's a good use to have someone help you with that versus also taking work off your plate.

So, again, looking at that what do I hate to do list. One other initial hires, even though I know how to do my own books, I hired a bookkeeper really quickly because it's not worth my time. It's something that somebody else can do and do it high-quality for a relatively reasonable price. So, I have a pretty big professional team. I have an insurance specialist. I have a real estate broker and I have a banker. I think that's one that people miss is to have a relationship with someone at your bank because as your business grows, you can call upon them for all kinds of solutions for your business. So, I really rely on that professional team around me to be pros and give me shortcuts for a lot of these things.

CAMILLE [26:15]

I really like that. Now before we started the call, we've talked about systematizing things, which I think is huge. That's something I struggle with for sure, so having someone with a brain that works like yours is a big deal. But also, the mindset of a CEO and what does that look like and getting over hurdles? We were talking before this conversation was being recorded that when I changed my website, I have a website called www.mymommystyle.com, which is a lifestyle website for moms with recipes and lifestyle, parenting, travel, all of those things. And I was going more into the business space and I was trying to decide what to make my handle if I was going to do camillewalker.com, which was taken. And then I thought, I could .co, people don't always search .co and it was this whole thing and thecamillewalker was available, but my husband said, "Oh, don’t do that. That sounds so conceited." And so, I was relating that story and pick up from there and tell me what you said.

JILL [27:20]

Sure. So, the name of my company for the first five years was Sif Industries, S-I-F. And the whole story around that and it ended up being too much. When I explain the story, people were just like, "Oh, okay. That makes sense, but it didn't mean anything." The brand didn't mean anything to people. So, about a year and a half ago, I went through a branding exercise with a brand and creative specialist and when we went through the exercise, she was just like, "You know what? You need to be The Jill James." And I was really uncomfortable with it. I was just like, "No, we're not doing that. I don't want to be a personal brand."

And she explained to me why as the leader and the CEO of the company, I needed to be out front at least for the next few years of people recognizing me and coming to the business for me and the team that I'm building, but to know that the discipline is around the things that I've learned and experienced in my life. And she actually encouraged me to flex more. She knew what I had done for the companies that I had worked with. And she's like, "I know you come from finance. We don't tell other people secrets, but I know the work that you've done. So, how can we tell those stories about what you've done or empower those clients to come forward and provide you with testimonials and stories? Because the work that you've done is really valuable."

So, to me, it's more I'm by nature a behind-the-scenes person. And so, her push was, "You've got to conquer that and get out front and this is a way to push you to do that. If your name is on the company, you're going to step forward and be that leader." So, we had everything in a box ready to go by September of last year and it took me to April to actually put it out in the world. Because every time I thought about it, I was just like, "I'm not ready to own this." Being The Jill James and making that the name of the company, I agree with what your husband said. There is a growth process that goes into putting your name in the company in that way, especially if you're a service-oriented person.

I'm definitely a service-oriented leader and I just want to help. I want to help people do the things that are meaningful for them, so to splash my name across it felt like a big push. So, I think until you're ready to step into that, maybe that's not the right thing for you. But it gave me the push I needed to think about where I wanted to take the company and what was that next level for what I wanted to charge and how I wanted to structure my working relationships going forward. I really did need a different kind of brand.

CAMILLE [29:57]

Yeah. I think it's brilliant. I love that you chose The Jill James because there really is so much for you that you offer and also that people automatically investing in getting to know who you are to understand the business. I think that that speaks for itself when it's your name and it's The Jill James. And I have a quote here that you said in an interview recently. This was with ShoutoutLA and you said, "I'm about as risk taking as the average man, but as a woman, I'm an off the chart risk taker." That's been important for me to understand in helping others approach change and hard decisions. And I think that that is one of those moments where you took that risk of knowing maybe this isn't something I would have been comfortable even five years ago doing or in 2015 when you started it, but you are in this place claiming this space and it's so powerful.

JILL [30:57]

Thank you. Yeah, it's definitely been a big moment of transition there, but many of the life transitions in the last year, year and a half, so rebranding has gone along with that. What I have learned from clients that I've worked with is you have to go out to the edge of your comfort and a little beyond. If you go too far, it shuts you down but you've got to get a little bit out of your comfort zone and learn to live in that space just a little beyond where you want to go and that's where growth comes from.

CAMILLE [31:27]

I love that. I think that there's a lot of power in that and that's right where fear exists where it's like just enough where having a mentor or a coach can help you to see that and frame it in a way that it gives you a step-by-step process. And I think that's where a lot of us get hung up is knowing, what's that next baby step without taking a huge leap that I can't sustain? So, what would your advice be for those who are in scenarios like that? How do you help them determine what those steps are?

JILL [31:57]

Get a little push forward, when I think about that, some of the comfort that I take is in numbers. Most of the founders that I work with are really good at spinning a great story about who they are and what they do and the vision that they have for the company, but there's also a financial story that you have to be able to tell. How many customers do I need? How much money would that generate? Who would I need to hire? How much would that cost? What would I have to pay in taxes? And making the companion to the story that we're telling in a more comfortable space, in a story telling space, having numbers that go with it, for me, always calms me down.

So, I know everybody does this, but when I have a freak-out moment, I crack open my spreadsheet and I'm like, "How many customers did I say I was going to need? Am I there? Do I have the pipeline? Okay." I have trust from experience of, if I do these activities, it will come. Sometimes, it's a little slower. Sometimes it's a little faster, but it always happens. And so, for me, having some kind of roadmap of what I expect to happen if I do certain things and seeing that it's happening takes away some of that anxiety for me.

And I have seen that with my clients. We will make their design and be really aggressive. "I don’t know if I can do it." And we can say, "Let's give it three months. And if we see the business moving this way, we'll keep going. And if we don't see the things that we predicted happening, we'll reevaluate." And that's part of having a longer relationship because then we can see, did the things that we predicted, did the things that you think you understood about your customer and about your audience, are those things happening? Are we moving in that direction?

And I think having those successes, I work on a 90-day implementation plan after we make the plan and I sit with the client and do it because you need to see that the success is happening. You need to see that this is actually a real thing. This is reasonably predictable and you can count on it if you do these activities. So, getting those early wins, I think, and seeing that the path is one that you can handle and having somebody with you who in those scary moments that sometimes our business reviews are just like, "This is freaking me out." And we talk about why.

But I think you have to manage each new plateau or each new limit that you hit, your mindset has to go past that. So, you can sit separately and do mindset work, but I find it works better as you're running your business when you hit that moment, let's address it and figure out what is the scary part of this and how can we make a strategy to make you comfortable walking through that scary part and knowing that you have somebody with you?

And so, that I find is the way that we move forward is we just keep finding those new limits and being like, "This next part feels scary again." And we can look back at the success that we had and how we pushed through it to make a strategy for the next. And sometimes, people just want to stay where they are for a little while and that's okay.

So, I think just being honest with yourself of what's going on, why is this scary, what are you afraid could happen, and putting that out there. And then, sometimes just saying it is like, "Oh, you know what? I'm being a little silly or maybe now that I said it out loud, it's not as scary as I thought it was. And now that I see the strategy for it, I just didn't have a strategy." So, I do think those conversations absolutely come up for new CEOs who are going through these growth phases and part of it just accepting that you are going to feel like this on a regular basis. If you are staying in your comfort zone, maybe you've made one breakthrough, but you're going to stay at that level if you don't reach the next limit and figure out how to get past that limit. I think as an entrepreneur, if you want your business to grow, you have to accept that you're going to keep walking up to those limits and figuring out how to move to the next level.

CAMILLE [36:02]

That's really powerful. Everyone needs a Jill James. This is awesome. Now, you talk a lot about pipeline and setting up a pipeline. Talk me through a little bit what you're referring to in that sense and if maybe there's a formula that those who are listening could apply to their own business.

JILL [36:20]

Sure. So, when I think about pipeline, it's about knowing who your ideal customer is and what your offers are. And then, if you're in more of a product or an e-commerce business, how many people are flowing through the business? The example I got when I was learning it for any business is if you had a physical store out front, how many people are walking by it and seeing it?

CAMILLE [16:40]

Numbers game, yeah.

JILL [36:41]

Yeah. That's step one. Are enough people getting a look at what you do? And then, from there, are you having a conversation with the people who walk by that are meant to walk in the door? So, are you inviting in and calling to the people who are the right people for you and accepting that some people might look like the person who should walk through the door, but you need to let them walk by or come in and go out?

So, when you have that group of people that you know are well-qualified to be your customer, then that's the point where we really start with how do we develop them? How do we nurture and how many do we need? And then, knowing this is where they fit for the value of the sale. So, if it's like, "Okay. I think this customer could be in my $5,000 package versus this person's more like my $500 package, what's the effort that I put in? What kind of timeline do I look at?" And then, knowing, "Okay. If I want to have $5,000 this month, I need to have $10,000, $20,000, or $30,000 available in total deals, so that enough people sign up in that given month."

So, that's part of figuring out I think for you individually of what is that flow that makes you feel confident as you get better at sales or as you refine your nurture campaigns, your lead gen, and you're calling more specifically to that person who's meant to walk through the door for you. This will get easier and the amount you need in your pipeline will get smaller to feel confident that that number can be hit. But there is a way to back into if I want to make this much per month or per quarter, what needs to happen overall? How many people do I need to talk to and what mix of people do I need? And where do they have to be in the process to make that happen?

So, if you're really, really good at this, it's probably double what you want to hit in a month, you need two times that in your pipeline. If you're just starting out or times were inconsistent like they have been in the past year and a half, you might want as much as three or four times the amount that you want to hit in your pipeline because you can't hold on to, "I just got to have this one person say yes." It's like, "Hey. There are 10 people out there to have this conversation. I can go back and check in with them. Somebody's going to come through. Somebody's going to say yes." So, I do think in that having the activity and cultivating your relationship to people who you know are qualified to work with you, then moving them along the path to working with you knowing that not everybody's going to come through.

CAMILLE [39:20]

Yeah. I think that that is a lot of times, what's very easy to get emotionally wrapped up in the one or in maybe three deals you've worked on for a really long time, and then it doesn't fall through and to be able to take that emotion out of it and say, "No, this is a numbers game whether it's online or physical like a physical interaction that we just have to put ourselves out there."

Would you say for those who are listening and love these ideas and are wanting to implement more strategy and purposeful action plans, but may not be able to afford a coach such as yourself, what would you say would be a good place to start on a smaller scale? Because I feel like you're working with huge companies. I don't know exactly who your ideal customer is, but let's say, they've been in business for maybe five to ten years, and they would probably be at the stage you're at. But, let's say, we're talking to someone who's been in business for maybe one to three years, what would you suggest they do before getting to where you are as far as strategy and those mind blocks?

JILL [40:34]

Yes. I do try for people who are earlier on or aren't at the point that they're ready to work with me yet which I want people to have at least one year of running their business because you don't know what you want to do until you've tried a little bit. So, between one and two years is typically when I start with people because then they have clarity of, "I want this. I don't like this." And then, typically they have at least a $100,000 in sales. Otherwise, its' a big investment. You're going to make it out of your personal savings, so if you want your business to be able to pay for the investment, it's going to be somewhere between $100,000 and $200,000 is typically the place to start with the ambition of, "Hey, I want to be this big. I want to double or triple or five times within a couple of years. I just want to be a significantly bigger size."

So, I think that some of it is you do just have to go through. There are so many good and affordable programs around developing lead generation and thinking about what you want your business to be and basic business fundamentals, paying $49 to join a webinar. Paid webinars are often a good investment because they're going to just tell you stuff versus when you're in free webinars, you know there's a glitch coming. So, you're going to get a little nibble of something and then you're going to have to sign up for a bigger program.

So, look for opportunities of people who will just share information for a slightly paid way. I have a colleague named Lisa Niser and she does a tech workshop, just basics of entrepreneurial packs. And I think it's a couple hundred dollars, but she goes through all the stuff you need to know as an entrepreneur, why taxes are different than when you were a W-2 employee, and what different terms are just goes through it, then you pay and it's one session and you're done. But it's a way to level up. It's typically what you need to know in those areas.

So, I think looking for people who can help you at that stage, everything has to be stage appropriate for you to get you to the next stage. So, if you're really in an early stage, I think I even go back to some of Amy Porterfield stuff. She's meant for people making $50,000 or less and just getting started. But she's got good foundational and basics stuff and there are a lot of people who have scaled programs who will speak to the basics really well and going back to get those basics, that's great. That's going to serve you throughout your time.

So, whatever it is, if it's a local business organization or a women's business owner group. I have just a group of us who own companies and we're divorced and we get together and we talk about running our companies and being single moms. So, whatever your group is that helps you, get in that conversation and have it and I think that's a great way to start. For me, I always want to be in service to the community, so I have a free newsletter that I write every week. I often will post very informational things on my blog. I just post, how to consider your health insurance for 2022 and what are different options for you? Should you hire kids? And if you want to, how do you do that? So, I always try to put stuff out there that not necessarily like, "Hey, here's how to work with me, but here's some topics that raise your general level of business understanding around how your personal financial life works with your business, things like that. We've got to make your life run."

So, that I think, look for those kinds of things where it's highly informational, lots of information sharing, lots of support for you as an entrepreneur, really positive. Find things like that that you can do until you get to the level that opens the door that you're truly ready for that growth. You're ready to go and commit because if you want to level up, you've got to completely be all in.

CAMILLE [44:38]

Yeah. I think that's really good advice because I've noticed that oftentimes, those who we surround ourselves within our personal, recreational, and business, it all effects the way we think, the possibilities that we see for ourselves and also even limiting beliefs that we may inherit without even meaning to. So, that in and of itself is really, really good advice to look for opportunities to learn from people online and in person that can relate to what you're going through, especially as women and as mothers and finding people that are there to rally around you and really give you that encouragement.

Can you think, just to wrap this up, of a time in your business that perhaps you learned from a mistake or something that you really tripped up or an experience where something that may have been seen as a setback really propelled you forward?

JILL [45:39]

Yeah. I think at about the two-year mark, I was fairly highly compensated. Before I started, my son was two years old, had this smaller scale business and I really thought about, am I truly ready to walk away from my career and have this be the direction that I go? And I think that two years, 18 months to 24 months is a place where we're at that tipping point and you hear over and over from people of like, "The last time I seriously considered going back to a job was 18 to 24 months." Because the second year of business is a lot harder than the first and I don’t think people necessarily tell you that. But the first year, all your friends and family want to jump onboard and help you and all obvious sales you make right away. And then, the second year, you have to go talk to strangers and it gets harder. And there's definitely that moment where you're like, "Oh, should I just get a job? That seems easier."

So, I actually went to the process and was deep in the interview process of being a COO, CFO for a small publishing company and I sat with the founder and I was like, "You know what? I like making the decisions you're making better than being here." And I had that taste of the flexibility and freedom of, "I don’t want to be tied to the flexible holiday calendar." I don't want to say, "I can't go to this thing for my kids."

And I think work is changing, if you can find the right job, you can certainly find more flexibility than you could five years ago. But for me, there was just no way again that I could be the mom that I wanted to be and have a full-time job that was that kind of job. That was the burn the boats moment for me of, "I have to fully commit to this business. I have to figure out how to make it work on my terms, the things that are important to me for the times I want to be there for my family, and bake that into reinforcing. I'm not going to do this like other people do it. I’m going to do it in a way that works for me. I'm going to design the business that way and I'm going to commit to it."

And so, that was four years ago now. And it definitely doesn't mean there aren't any hard times because every time you level up, it gets hard again. And then, it gets easier and then you push forward. And then, it gets hard again. So, the cycle of growth I think is something I have to accept and I just push through and have our support around us. But I do think that would have been in that moment, a massive mistake to give up the business at the two-year mark versus just trying to figure out what would this have to be to make it work for me?

CAMILLE [48:17]

I love it, pushing through the hard stuff. I think that you've talked a lot about very hands-on approaches to pushing forward when things get scary and investing in coaches and mentors and that has been so helpful. If there is one last bit of advice, what would you say has been that something that propelled you forward in those moments that you wanted to stop?

JILL [48:46]

I think about what it would be like to have a job honestly. I think about what do I want for my son? How much do I want for my self-care and taking care of myself and being able to direct the course of my life? And I think also now that I'm in more of a self-financed situation, I'm completely in control of where the business goes and who I take as a client and how much I tune it up and down. So, to give that up and have somebody else calling the shots is usually the thing that is like, "Okay. Go back. Work the pipeline. Call everybody. Find that incremental client. Figure out what's not working. Figure out what are you going to do to get to the next thing?"

Take a day. I often use day use to go to a nice hotel just for the day and be in a different environment and work. Just have a day to think about what my business is and work on some planning stuff. So, I think sometimes removing yourself from your business and giving yourself a little space and actually let yourself think about like, "What would the world be like if I did this other thing?" Sometimes, you just need to give yourself permission to look into the abyss and be like, "Okay. What would that really be?" Every time I think about going back to a job, I'm just like, "I just know that's not going to work. It's not." And so, I have to double my efforts and make this work and get smarter about how I do it.

CAMILLE [50:16]

So good. Self-care, taking time away. My sister and I, we do a quarterly hotel night where we go and we do different businesses, but we love talking strategy. And if you can find someone in your life, you don't have to be with someone, but for me, I find that if I can have someone that I can tag team ideas and also take time to relax and really rejuvenate away from everything especially as a mom, it just gives you so much clarity. And looking into the abyss, I love that term. I'm going to use that now.

So, this has been so helpful, Jill. I think that you have given us so much to think about and I hope for those of you who are listening that you're listening with a pen and paper and have written down those step-by-step strategies. For those of you who are listening and want to hear more, Jill, tell us where we can find you.

JILL [51:08]

Sure. My website is thejilljames.com. I offer a free 30-minute strategy session, which people ask me about a consultation, that's what it is. So, it's available on the website. You can book it two weeks out. So, there's that and the newsletter, I post in LinkedIn a lot. I put a lot of daily tidbits there about things I'm thinking about, things that come up with clients, so all different ways that you get to know me and get a little bit of the recommendations and tips that I would give to you if you were a client, but in a way that's on your own terms.

CAMILLE [51:46]

Very cool. And if you happened to have missed our LinkedIn episode, please go back to Mindi Rosser and listen to that episode about all things LinkedIn because it is mind-blowing what you can do to grow your business on LinkedIn.

JILL [51:58]

Yeah, absolutely. That's almost all the social that I do. LinkedIn, for my customers, is a great place to be.

CAMILLE [52:07]

Yeah, awesome. Thank you. This has been awesome. Thank you so much for being here today.

JILL [52:13]

Yeah, absolutely. Thanks for having me, Camille.


CAMILLE [52:17]

Thank you so much for listening to this episode of Call Me CEO. I would love to be friends with you online. Please subscribe to Call Me CEO here, wherever you're listening to this podcast and come hang out with me on Instagram. I am @camillewalker.co as well as @callmeceopodcast. And each week, I like to share with you behind the scenes of family life and running a business as well as tidbits here and there of things that I like. So, come hang out with me. And I hope that if you are listening to this and you're not quite sure of what your purpose or what your why is that you have taken my free 5-day challenge of discovering your purpose and your why at www.camillewalker.co. Thanks for being here, friend.

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