Business Systems Made Simple w/ Jamie GIlleland

If you feel like you're doing way more than you need to in your business, it's probably because you are. Most likely, if that's the case, you do not have enough or the right systems and automations built inside of your business, which is why today I brought in expert Jamie Gilliland. She's an international speaker, best-selling author, and sales automation expert who has built and saved multiple businesses. On top of that, she has this amazing, amazing story about overcoming life's challenges and how these various challenges ultimately led her to being the business owner she is today and the expert she is in automations. So if you like what you hear in this interview and you want to connect with Jamie Gilliland, then do check out the links down in the description. Without further ado, let's dive into the interview.

Jamie, how you doing today?

Fabulous. Once I get the little button clicked, I'm great.

Confirm it's recording.

There you go. How are you, James?

I'm doing excellent. Super pumped to be hanging out with you today and talking about marketing and marketing automations, because that's your secret sauce and it's so, so helpful, especially with people being so busy nowadays. And just, I feel like people are just getting more and more on their plate. So it's ever more prevalent to talk about automations and how to use them to really live a more fulfilling life.

How did you—

Yeah. How did you, um, how'd you kind of like fall into becoming the expert? Was it just something that happened overnight or was it something you always wanted to pursue in terms of like marketing automation and getting to where you are today?

It kind of happened overnight. Um, about, well, 2003, I started a real estate company with a partner and we ended up franchising the concept. So I was the CEO of the franchise corporation. We had IPO on Wall Street. We were chosen the top one. It was a technic— technology-based residential real estate office. Life was pretty sweet. And then somebody rear-ended me. And when I went in for the X-rays, the doctor said— I was expecting to say you have whiplash. Actually, they sent me for an MRI. Expecting to say I had whiplash. And in turn, they said, you have a massive brain tumor and you have less than 6 months to live. Jeez. Um, kind of not what was in my plans at that point in my life. I had 3 small children. My daughter was 10 and my sons, I have twins, were 6. And my 4th child wasn't here yet. So I took off and there's a whole story behind that I call Option C. That I took off to take care of my health for 6 months. And when I came back, it was 2007. So real estate market was crashing anyway. But because I had literally written the book on how to run the franchises, big old manual, what color paperclips to use on what color this, you know, it was detailed. My, my role and how to run the corporate office, I hadn't created the systems for yet. I hadn't put in place my being out of the office and all of the staff who was used to saying, hey, Jane, I'm doing this. Hey, Jane, should I do this? What do you think about this? And asking me for suggestions. They didn't have me for 6 months and the company failed while I was out. So I lost my business, lost my income. 3 months later, lost my first husband and ended up collecting food, going from a high 6-figure paying job, beachfront, front row beach house, uh, fancy cars, fancy schools, to standing in line to collect food stamps. To feed my kids. Well, kind of a strange story, but I— where I lived, I lived in Hilton Head, South Carolina. There weren't many job opportunities for somebody with my background. If I wanted to go clean the hotels, I could do that, but— or landscaping, but there really wasn't a lot of other job opportunities. So I started my own company, which was a web design company at the time. But I kept thinking, so many people build their life around their business, and that's what I had gotten caught in. I hadn't built the business around the life, so I didn't build in the opportunity to take vacations, to get sick, to deal with situ— situations. So I became really passionate about creating systems for myself and then for my clients. Fast forward to 2021, 2 years ago, I had a dog— my dogs got into a fight. Long story behind that one too. That's a great story over beers. But, um, I got bit and it broke this bone. It ended up giving me a bacterial infection that I ended up in the hospital for 4 days, uh, lost my knuckle. Um, so I had 6 months of recovery. Literally the last day I was going for physical therapy and the doctor's appointment to finish out and say, okay, you're recovered. Somebody pulled in front of me in my brand new sports car, beautiful car I had just bought, uh, less than 3,000 miles on it. And she totaled the car, totaled the airbag, went off and shattered my wrist, was like an S. Oh man, shattered, shattered my wrist in 7 different places. So 6 months of repair of not being able to use this hand. So literally 12 months of working one-handed. And being in back and forth in doctors and physical therapy and all the stuff that, that trashed my company the first time.

Wow.

Lo and behold, my company this time, with me being partially there, having 2 assistants and my husband, we had our best year ever.

Wow.

So having the right systems in place allowed me to deal with my health and deal with— and I'm still dealing with some of it. I have some— I have a tremor from the, the accident, somehow triggered an autoimmune disease. But I still, because of the systems I've built, because of the systems in place, our company just keeps growing and growing with a minimum number of people in the process handling all the work. So systems work, and I've just become so passionate about them because of that.

Yeah. Wow. No, that's an incredible story. And I'm sorry that cars are not very favorable of you, or just people driving, I guess. People are on their phones way too much. When they drive for sure.

Well, you know, it's funny, the guy that hit me the first time literally saved my life. If he hadn't hit me, we wouldn't have found it. I would have been walking around and just dropped dead because it was a tumor that was pressing on the brainstem. Wow. And I had no symptoms. It just was there. But I was the 4th person he hit that in 2 days. They arrested him on the spot, but I'd like to go back and see if the other 3 people had something major happen in their life because of it too.

This guy's one purpose is just to save people without saving people. Exactly.

Exactly.

Oh geez, that's crazy.

I'll have to look into that later. Yeah.

Well, okay. So some things I want to unpack here. The importance of systems is just obviously prevalent because even when that second accident happened, your company was able to have its best year and just continue to grow and it still does with minimal minimal effort or even a minimal size teams. I feel like when people hear systems, it's a really big buzzword. People say scale with systems. They can hear you got to build systems and then it can be a bit of gray area for people. They can obviously dig into it and systems can go really deep too, depending on the size of your business, where you're at in your business, et cetera. So what kind of, I guess, how do you approach building systems, I guess, regardless of the size of company, if someone's just starting out, should they even focus on that early on? Do you have to a certain point before you recommend to start building systems?

Well, systems can be as simple as Calendly for your appointments, right? How many times have you played phone tag? Oh, how about this time? Oh no, sorry, somebody booked that since I sent it to you. Or back and forth with email. You know, that's the very basic first level of systems. But having those kinds of pieces in place from the beginning A, lets you be organized in your growth and your follow-up. If you're, if you don't have systems in place, I know from past history, people fall through the cracks. You lose track of it. When I first started using Keep, is the software that I use primarily for automation, when I bought it, back in 2014. I bought it in November, and in the business I was in, November and December were notoriously my lowest revenue months. It was the end of the year. People were out of budget. They were saving for Christmas. Every excuse in the book. So I got the hiccups all of a sudden.

That's okay.

So if they, if I made $2,000 in November and December, I was jumping for joy, which was not a lot with 3 kids, right?

Yeah.

So I started using Keap, which was called Infusionsoft back then, and sent out my first email in for Black Friday from Keap. Now, I had a pretty good-sized list at the time. So sent out an offer, made something like $10,000 that month in the last week of the month. Did the same thing in December, ended up from November of 2014, in the year of 2014, I made $60,000 total working from home. I was happy. I wasn't overjoyed, but it was paying the bills.

Sure.

In November of 2015, I made $60,000 in a month. So I literally 12x'd my company because things weren't falling through the cracks. People were being followed up with. The important ones were rising to the top so I could pay attention to them and take care of them instead of focusing on the person that was getting the free offer from me. So those systems can take a solopreneur over the, over the, the edge. There's a, there's a, there's a space there where people get up to, but they can't get over. So it gets them over that hurdle of being able to focus on what's important in their business. And still have all the busy work happen. So your first question, I believe, was how do I get people started regardless of their size? And I have a, um, tool I call my activity tracker, which you guys can go to tracker.keepitsimplestrategies.info and download it. It's just a little table, little worksheet, and it has a bunch of columns. And I have my clients stop, set a timer on their phone for every 15 minutes, so that in— they jot down on the sheet what they did for the last 15 minutes. Sent XYZ email, copy and pasted this, did that, looked up this, whatever it was. And then at the end of the day, I have them go through and say, this the responsibility. If I had a full organization, whose job would it be for this? This would be the social media manager. This would be the bookkeeper. This would be the janitor, right? Whatever it is. So A, they're tracking where their time is going. B, we're looking for repeatable tasks that can be turned into systems. And C, we're starting to build out the org chart. And look at where hiring the first person would make the most sense. So it's a great tool when you look at the granular activity. How many of us at the end of the day say, geez, that was an 8-hour day and I don't know what I got done, right? Happens all the time. Everyone I talk to, what did you do yesterday? I don't remember.

I ate some food somewhere in there.

Somewhere. I took a lot of phone calls, right? So, or I read a lot of emails, or I got lost in Facebook, right?

Right.

So this helps them track what they're doing. All of our clients get anywhere from 4 to 10 hours a week back once they look at this and we figure out how to start building the systems around it. And systems, as I said, can be as simple as a calendar or as complex as this is where we find our client. This is the next step and the next step, and this is who it gets handed off to, and this is what they say. So it can be an entire process start to finish. But the sooner you start, the easier it is to integrate the full longer process systems, right?

No, I like that. I like the idea of just tracking your time because you can easily see where you're getting lost in the weeds or where you're procrastinating or you're just wasting time on things that actually aren't moving the needle. And you can really pinpoint like, wow, I'm actually not even doing the thing that does grow the business, whatever it may be, for whoever's listening.

Exactly. Well, so many people start a new business because they're good at one thing. They're excellent at accounting, or they're an excellent mechanic, or they're an excellent whatever. And they get frustrated because they see billing for other clients and what the owner is getting, and then they compare it to their salary and they think, wait a minute, I'm only getting 10%, 20%, maybe 50% of what I could. If I start my own business, I can make more money. Woohoo, right? But they don't think about all the supporting staff around them that are doing all the other things while they focus on that. When they start their own business, all of a sudden they have to wear all of those hats and they get lost and they don't know how to do it. And that's why so many startups fail.

What kind of companies do you, um, at, uh, Keep It Simple, which is Keep It Simple Strategies, uh, what kind of companies do you typically work with?

Um, my primary market, just because of where I've been in the speaker arena for the last 10 years, is speakers, coaches, and authors. So the majority of my clients fit in that realm, and they're building systems around, um, sales of classes, creating group courses versus one-on-one products. But I also work with a lot of trade-based people. So we've had a funeral home, we've had truck drivers, not truck drivers, tow truck.

Yeah.

Right. So we've had some brick-and-mortar style service businesses as well.

Gotcha. So my audience, mostly coaches, content creators, authors as well, kind of fall under that, that umbrella of people. What do you kind of recommend for them to, you know, get started in creating those systems? Obviously, there's like tracking your time, but do you notice any kind of common trends you could kind of like— I don't want to say cookie cutter, but kind of give people almost like a cookie cutter, like baseline at least to kind of get started looking at their business maybe in a different way for systems?

Absolutely. For coaches, the cookie cutter system starts with a good funnel. Where are you attracting your clients? How do they get the download? And please, for the love of God, don't just give them the thank you page that delivers your IP product, because then when you look at your email addresses, you start getting Mickey Mouse at blankwords.com, right? I've seen some of the most obscene emails that people have gotten, and they've given away their intellectual property and not done it. So having them opt in, delivering the product by email so that your, your bribe— I call it an ethical bribe— they're getting your IP and you're getting their real email address. If they don't give you a real email address, they don't get your IP. Having that in there, then upselling with whether it's other landing pages or email marketing to upsell them into courses, having the courses be automated so that the minute they pay, they've, they're given an email with the username and password and access. I see so many coaches that are like, oh yeah, every morning I go through who's bought And then I send them access and I send them this.

No, put that on the tracker. Stop. No, I'm glad you brought that up because I'm the same way as you. I'm really big on systems. I did productivity coaching and that's where I found out about like automating course sales and things like that. So I learned about systems. I was obsessed with like, how do I trim my work hours? You know? And using, just being like clean, organized and all that kind of stuff. So I mean, I get it, you know, delivering it, making sure that things link together. And I think having the right tools is so important. But if someone's listening to this and they're like, holy crap, like that's what I'm doing. I'm manually sending this. I'm manually doing this, granting people access to the course every single time someone buys or the product or giving them the lead magnet once they give me their email address, like That is a clear-cut sign if you're doing anything like that, that that can be automated. You know, you, there's so many tools available to us where we can just do that. My favorite tool that I use is Kajabi and they do a great job of just making it really simple. Like they have the funnels, you click it and it's like, here's the opt-in page. Here's the lead magnet. It automatically just puts it all together for you, you know, but it kind of depends on the tools you decide to go with.

Yeah, of course. And by the way, if your assistant is doing that, that's not any better.

No, absolutely.

Somebody else say, oh no, that's what I hired my assistant for.

No, they can do other things like responding to comments or email questions. You can't, you can't really automate that, you know, and even if you did with like ChatGPT or something, it wouldn't give a great customer experience. So assistants could do that. But no.

Yeah. So, so yeah, that's the first part. The other part that is, I think, really important in creating systems for coaches is the ongoing contact with people. I had a coach come to me and say, oh, I've got a list of 35,000 people. Excellent. Great. When was the last time you emailed them? About a year ago, I'm like, you don't have a list anymore.

No.

Right.

Yeah. I wonder what their open rates would be, the percentage when they start emailing again.

The list and got rid of the literally dead emails. I think there were 15,000.

Wow.

And we re-engaged them. So we got them back up and got good open rates for them. We do— I do done-for-you work as well as just teaching people how to do it so they do it themselves. So we work with startups all the way through. Here's our system, here's what we want, go do it.

Right. So in terms of that, because that's a big piece of what I teach people with the email marketing, I firmly believe in it. It's worked great in my life. What do you kind of recommend in terms of email marketing? Because I've had people I talk with, they're like daily emails, and then there's some people are like, all you need is one email per week. What's kind of your take on just staying active and keeping that list fresh?

Um, it's kind of a double-edged sword. So minimum would be once a week. Minimum. Um, I like the daily if it's content rich. If it's buy now, buy now. Buy now, Buy now, buy now, buy now, buy now, buy now. It gets overwhelming and people are going to unsubscribe. Now I have some coaches who are brash and abrasive and they say that's fine. That gets them off my list. If they're not going to buy, then get rid of them. And some people have that mindset and that works great. Others are more nurturing and don't want to say, hey, you haven't opened my emails, I'm deleting you off my list, right? So keeping the list engaged, in order to do that, you've got to give them good content. So whether it's, you know, daily tips, whether it's stories that are Um, you, you're parts of your own story, parts of clients' stories of how they had X, Y's X problem. They took Y course and they got Z results, whatever, whatever the success stories are with little, hey, by the way, book a call with me and let's, let's talk about how we can get you the same successes.

I know a really popular strategy I've seen with people is where they send their email, very content rich, and at the bottom they just kind of do like the PS, like, by the way, whenever you're ready, here are a couple of ways that I can help you. And it can be like, one, you can book a call with me, or two, check out my course or join my Facebook group and limiting it to like 3 different options. I kind of like that approach. Something I even do with my email list. I think there's a time and a place where it's time to do like the hard sell where you're very direct. But I think for the most part, like, yeah, I agree 100%. It has to be content rich and showing that you're there for them. Kind of what you said got me kind of thinking. I feel like if I feel like if you're a very nurturing person, it's going to show in your emails and it should show in your emails. But if you're a very direct person, you can show that in your emails. But I wouldn't say like it. I would say like pay attention to who you are if you're listening right now to like, if someone tells you, you need to be direct in every email and you're a nurturing person and it feels off to you, then I mean, I'd say to kind of go with your gut on that part.

Yeah, absolutely. And that's why I say there's no one size fits all. It's, it's what works. And yes, the content rich with the PS is one of our best strategies. However, I keep it to one call to action. I don't give them 3 options. So I might have a theme for the week, and on the first one, it's, hey, if you want to talk, you know, if this hits a nerve and you want to talk about it, here's my calendar link to book. Let them book a 15 or 20-minute exploratory call. Then the second one, the next email, still on the same theme, the PS might say the course Susie took is XYZ and here's the link if you want to check it out. So direct link. And then the third one might be something different but around the same. So instead of giving them 3 options in one email, giving them daily different options.

Yeah. Okay. Right on. I dig it. Okay, Jamie. Well, one question I love to ask people is why do you think that people, when they listen to podcasts, they consume content, et cetera, online, they'll consume a lot, but they won't take action. What do you think is the real defining factor between the people that win and the people that just kind of stay stuck where they're at for months or years?

Fear. I think fear holds too many of us back, whether it's fear of failure or fear of success. There's something if you're not 100% focused on your results. And one of the things I do is every day in my journals in the other room, um, I write down in the morning what my long-term, my BHAG goals, the big hairy audacious goals, right? Or 10X goals or whatever you want to call them, what my big goals are. So I write down every day, I'm a multimillionaire with 9 figures in my bank account, right? And the multiple things that go with that. And every evening I write them a second time so that those goals are constantly in the back of my mind. Then I also write my target goals for the short term. Gonna have this program kick off and have these results. I'm looking for these many new souls to share what I do with this week, whatever. So I keep those goals in front of me. If I'm focused on achieving what I'm writing every day, it knocks fear out of the way. But if I don't have a clear goal or a clear destination, fear helps people procrastinate, stops them from taking steps. I'm not, I'm not worthy. All those stupid things that are stuck in the back of our heads. Yeah, my, my family Unfortunately is prone to a lot of those. Money doesn't grow on trees. Who do you think? You know, we're not that kind of people. We don't make that kind of money. Well, damn, I'm, I do and I am, and I'm breaking the mold, right? I want out of the crab pot.

Love it.

Yeah.

I love the idea of writing out your, your dream. I do it every day too. Journal right here, but I do it every morning and I plow through journals. So huge proponent of that. And I've noticed that the things that you write down, you really embody, like you said, it gets stuck in the back of your head and it really taps into that reticular activating system where if you want a red Honda, you start to see the red Honda, you start to see those opportunities, those systems that you could build or the people that you could reach out to or opportunities of when to say something. You know, to get you closer to that goal because you get obsessed with it in your mind. And it's just a matter of taking that action. I feel like people know when that action is. But yeah, like you said, it's that, that fear that can hold them back. And I think there's no easy way around it. If you listen to this right now, like you just have to be courageous, which is taking action in the face of fear. It's being scared to get on the horse, but doing it anyway.

So what do they say? False evidence appearing real.

Yeah, fear.

Fear.

So good.

So ignore that false stuff and focus on what you want and you'll get it 9 times out of 10.

Love it. Amazing, amazing story. Amazing content you're sharing with us today, Jamie. Where can people connect with you? What's the best way for people to reach out if they're interested in working with you, etc.?

Sure. If somebody would like a 15 or 20-minute call J-A-M-I-E, jamieg.com. And, um, otherwise, Facebook or at Keep It Simple Straight.

Okay, right on. I'll make sure that we have links down in the description for any and all things related for you to connect with Jamie to make it easy for you. Other than that, take what you learned here, take action on something that you from today's episode, and we'll see you in the next one.