How to Profit From VIP Days with Jordan Gill

Sometimes, you just wish you could do several months worth of things in a single day. You’ve felt it in business and probably other areas like health or personal development, too.

What if you could do that as an entrepreneur for others? You’ve more than likely seen VIP days as a revenue stream for client-based businesses. But instead of making it an add-on to your business, what if you could turn that concept into the main offer of your business?

Today I have Jordan Gill of Systems Saved Me who has made VIP days the cornerstone of her company. In this episode, we dive into the upside of having a VIP day offer in your business.

On this episode of Promote Yourself to CEO:

5:04 – Why is Jordan so passionate about VIP days versus other types of service offers? She tells her story.

8:21 – Jordan describes what she did for VIP clients and the kind of entrepreneur VIP days are especially well-suited for.

12:45 – What VIP day ideas has Jordan seen from others? She reveals what any VIP day offer (including the more intangible ones) really comes down to.

16:21 – Jordan discusses what she did during her three-day workweek, including the non-VIP client days, and what.

18:22 – Jordan shares what she dislikes most about the retainer business model and how a VIP day offer helps mitigate it.

21:38 – What can attendees look forward to in Jordan’s upcoming Done In a Day virtual conference?

25:18 – How can you know if VIP days are a good fit for you as an entrepreneur? Jordan reveals a couple of things you’ll want to consider.

Mentioned in How to Profit From VIP Days with Jordan Gill

Racheal Cook: What would it do to your business if you could condense months of work with a client into a single day? We are going to dive deep into all things VIP Days with my friend Jordan Gill of Systems Saved Me to talk about how you can transform your business model, reduce how much you're working by collapsing processes it could easily take months into a single VIP Day with a client.

Are you ready to grow from solopreneur to CEO? You're in the right place. I'm your host, Racheal Cook. I've spent the last decade helping women entrepreneurs start and scale service-based businesses. If you're serious about building a sustainable business, it's time to put the strategy, systems, and support in place to make it happen. Join me each week for candid conversations about stepping into your role as CEO, the hard lessons learned along the way, and practical profitable strategies to grow a sustainable business without the hustle and burnout.

Hey there, CEOs. I am really excited to have this conversation with my friend Jordan Gill today because we haven't talked about VIP Days here on Promote Yourself to CEO but I have purchased multiple VIP Days from different service providers and I've also hosted several VIP Days. I was thinking when I talked to my friend Jordan, “Wow, this really is something that I think a lot of people look at as just an add-on, something they might do once in a while, but very few people are talking about making it the cornerstone of your business model the way that Jordan is.”

If you’ve never met Jordan Gill, she is the founder of Systems Saved Me. She also has a podcast called Systems Saved Me. I was on it a while ago talking about our process for creating a 90-Day plan and that was a really fun episode, I'll make sure to link it up in the show notes. But recently, we were both at the ConvertKit Craft + Commerce Conference together and I loved hearing her talk all about the different types of VIP Days that she is seeing her clients create.

I had previously invested in a VIP Day with a copywriter, a VIP Day with a brand strategist, a VIP Day with a photographer but I think sometimes when you don't see examples, it's really hard to envision what is possible and that's why I'm really excited about this conversation because Jordan is going to go deep into different ideas for VIP Days, different industries that could do really well with them.

If you are ready to have something that doesn't require you to commit super long term with clients, maybe you have a three-month or a six-month program you've been doing or service you've been doing but you know you could collapse that down into just a day or two days, you could see so much more flexibility and freedom in your business.

It's so funny because since we've talked about this, I'm now seeing VIP Days pop up everywhere, these immersive intensive experiences. I think it's going to be an interesting one to listen to. If this piques your interest, I'm going to encourage you to make sure that you head over to her Done In a Day™ Virtual Conference that is coming up September 5th and 6th. This is coming up very, very soon.

But if you use my link, she's created a special link for me, it'll be for Done In a Day™, we are giving an extra $10 off to anyone who signs up with that specific link so that you can have a full two days to understand everything there is to know, all the ins and outs of what is possible with adding a VIP Day into your business.

I will be there. In fact, I purchased a whole ticket with the team to go do their behind the scenes of how they're running this virtual conference because it is so interesting to me to see all of these different creative examples. I will also be learning right alongside of you. Again, I hope you enjoy this conversation and if it piques your interest, go over to get your ticket for the virtual conference.

Hey, Jordan. Thanks so much for joining me here today.

Jordan Gill: Yes. Thanks so much for having me, Racheal. Excited to chit chat about one of my favorite topics, VIP Days.

Racheal Cook: I'm so excited to talk about this because I feel like VIP Days are becoming more common as you have blazed the trail into really proactively talking about them in the space, but before we get into VIP Days and what they are and how they can benefit your business, I want to hear your story just so everyone knows why you are so passionate about having VIP Days versus other types of services.

Jordan Gill: Yeah, totally. I started my business in 2016 and I started how most people do with monthly retainers. I feel like that is a typical pathway, it's like, “Okay, you're supposed to do one-on-one clients for monthly retainers because of stability, safety, and all these things.” Five months in, I hated it. I was making decent money. I was making about $12,000 a month and I started my business making $12,000 a month so again, it was this weird like, “This is what should be making you happy from everybody else's standards but you actually hate it.”

Five months in, I was like, “Well, I need to figure out what I do like.” I went on this quest. I'm a bit of an explorer, pioneer vibe over here except for not real life outside, more like in business, and so I went exploring and found VIP Days from the sales coach who I had bought a VIP Day from her and it was a really great experience.

I was like, “Well, can I do a VIP Day? As a systems person, I want to be able to build something in a day.” She was like, “Yeah, sure. Why not?” I was like, “Okay.” Gave it a shot and my first VIP Day client actually came from my best friend who I don't even know how she knows what I do because there's no way she explained it properly but somehow, something, a nugget went to the right person and they were like, “Oh, I need that.”

It was a fitness competition coach and basically from there, I was hooked. It was just like sold, I love it. I love being able to come in for a day, knock it out, and then rest. That's just my vibe. I'm not like consistently doing the same thing every day, having the same energy. I'm like, “No, today I have the energy and then tomorrow I don't.”

That was my journey for three years, four years I guess until I realized everyone else kept asking me like, “I don't understand how you're just working a couple of days a month with clients, frolicking around, traveling, and doing all these things.” I'm like, “Oh, it's because I do VIP Days.” So the intrigue started and I launched my program in March 2020, literally the weekend that the world shut down, of course, and two years later, we've helped over 400 clients create and sell VIP Days. That's it in a nutshell.

Racheal Cook: That's it in a nutshell. It's amazing. A lot of great things came out of March 2020. That was also the month that we launched the Collective and shut down our other ways of working with people. It's funny that it ended up being a great time to go all in on a new direction. I love that.

For you doing a VIP Day, just to clarify what your VIP Day offers, you’re an operations systems expert, so you would come in and do what for people?

Jordan Gill: I work with seasonal business owners, so again this fitness competition coach is somebody who is off-peak and on-peak. I work with wedding planners, tax professionals, hail damage consultants, wine consultants, it's a very interesting bunch of crew but I love the variety but the thread amongst all of them is they have on and off-peak seasons. I would work with them in their off-peak seasons to get them ready for their on-peak.

I would come in and help them build out their CRM system, Customer Relationship Management, and really get them organized from an onboarding management and off-boarding of their on-season clients. It was super, super fun. I've done other VIP Days recently that are different but I did that VIP Day for up to five years.

Racheal Cook: That's amazing. It's so specific too, specifically setting up their CRM to manage all of their clients during the busy season. I love how clear that is. For them, it means it's all set and ready and they're not having to come up with something for you to do every month on a retainer.

Jordan Gill: Exactly. They love that. It's interesting, my clients like to watch me which is not usual for systems people but they like to familiarize themselves and watch me do my magic and I'm talking them through. They're not retaining all of it by any means but at least they're understanding and watching how it's supposed to be done and then when they get in there, it's not like if you work with other systems people, they go create this thing and all of a sudden it's like on you and then you're like, “I don't even know how to log on or log off. I have no idea what the system is.”

We're just chatting and whatever. I'm pretty decent at multitasking and having conversations and doing work so it works out for both of us, but that's a unique thing too is they like and that helps to sell the VIP Day is that they actually get to watch. That wouldn't sell for some other people who don't like to do that but again, you can create your VIP Day however you want.

Racheal Cook: I love that in you describing this, it's a very clear container, a VIP Day is very different from retainer work because retainer work is just ongoing, every week or month you're getting something new, you're ebbing and flowing between all the different projects. This is a very clear, “You're going to come work with me and get this outcome from our time together.” I love that. Definitely good for people who like project-based stuff to get in and get out and not the ongoing grind of what we think of with most retainers where it's the same over and over and over again.

Jordan Gill: Yeah, the never ending to-do list. If you like the maintenance and the accountability or whatever the work is that you do on an ongoing basis, then great, this type of work is for people usually who have pretty strict energetic capacities and what I mean by that is like I have a few chronic illnesses and I have to regulate and adjust my work schedule to when my energetic flow is.

To have something ongoing is really, really, really tough for me and so I've had to really get clear on, “Okay, what's my max of Jordan energy? Then do I need to take the rest of the meetings on my bean bag or do I just need to not take those meetings?” whatever the case is. If you're somebody who likes to create and be in that energy and then flow into more of a rest state for a while, then VIP Days are going to be great for you.

Racheal Cook: I love that. Now that you are coaching other people to create VIP Days, I'm really curious what kind of VIP Days you're seeing because I know you mentioned you've taken a sales VIP Day with somebody, I've done copywriting VIP Day where somebody got all of our sales copy for a promotion done all in one go, it was awesome. I've done a branding VIP Day where it was two full days together to do the full-on creative everything for the new branding.

I think it's easy to think about some businesses like that because they're projects that are very simple to understand and wrap our head around. But tell me about other types of VIP Days you've seen.

Jordan Gill: Oh man. I will pick a few but some ones that are not as tangible, I guess I'll say, would be, I guess it's semi-tangible, but we have some doulas that have come on the program who create a post basically four-trimester plan for their family; who's going to help with this? Who's going to help with that? What are the things that you need to purchase? What sleep schedule should you try to adhere to, et cetera? Which is cool. It is tangible-ish but it's in a unique industry.

Also got wedding planners come in and do literally wedding planning in a day and she's been a wedding planner for like 15 years and it's amazing and so she took her framework and plugged it into one day. We've had some money mindset coach VIP Days as well. We've had some anxiety coaches as well, support systems. I would say generally speaking, when it comes to having more of an intangible VIP Day, it still comes down to there is like a prescription or a solution that you're delivering, it just may not be like an Airtable base or something or website.

You still have to think through because we have also, she's an unconventional marriage coach who coaches couples through jealousy and communication issues. She has a couple come in, they talk at the beginning, then she has homework for both of them to go to in separate rooms while she prepares for the next session, then they come back, they review, they talk it out, discuss, and then she helps to create the solution of how they can communicate and work through these issues together across three months, six months, nine months, and whatever else. It's pretty cool what people have come up with and it really gets your creative juices flowing.

Racheal Cook: Yeah. I think that's so interesting. As someone who's purchased a lot of things, this actually makes me think a lot of, like you, I also have health challenges but I've invested so much into intensives, whether it's like a healing trauma intensive that I've done for myself or doing some retreat where I'm really doing some deep internal work to take care of myself. Those types of things are also VIP Days. We might not call them VIP Days, they might be called a retreat, they might be called intensive or something else but very similar. I love that. Very cool.

You now have gotten to the point where instead of doing any retainers, you were working like three or four days a month. What does the rest of the month look like for you if you only have a few client-facing days a month?

Jordan Gill: Totally. I worked three-day work weeks, Tuesday, Wednesday, Thursday, and I basically had four day weekends every weekend. It was lovely. I was also single at that time. It was just such a wonderful time. Now my life looks very different. It's still in a great way, it's a different season but I look back and I'm like, “Wow, I had so much spaciousness.”

The three-day work weeks would look a little bit like I would take usually sales calls on one day-ish, a few of those, and then another day I would focus on some different marketing efforts whether it was a guest podcast or going to an event of some sort, etc. Then the Thursday would be my VIP Day. Basically, that height of the week I would be like high energy and then fall into the weekend of four days and just rest, chill, and lean into that. Basically, it's like two days marketing selling, one day delivery is essentially how I had it set up.

Racheal Cook: I think this is so important for people to understand because there are so many ways we can set up our business to truly work for us and even though you only have those three or four client-facing days, you still have to do the marketing and sales in order to keep those days booked, in order to book yourself out for those VIP Days. That marketing and sales piece is still there. This is not an escape from marketing and sales, it is condensing them into shorter time frames with a super clear outcome for people to know about.

Jordan Gill: Totally. Yeah, because I think there really isn't any business model that you can escape marketing and sales. Now, monthly retainers give you this false sense of not needing to do marketing and sales because you feel very comfortable because you currently maybe have the amount of clients that you want and so you think, “Okay, I can just chill.”

Unfortunately, sometimes you lose a client or two, or even with some of my VIP Day folks, three clients within a two-month span. That's where I get on my soapbox a little bit about monthly retainers is because I don't hate monthly retainers, I hate them for myself but I don't hate them inherently. But what I do dislike very strongly about them is this false sense of security that they give people in business. They get very comfortable and then something just happens.

Life happens, a client drops you, a recession's happening and people are dropping their contractors. That is real life, it’s not Jordan just living up in a cloud. I hate to see that and I hate when then you're having to start from zero from a marketing and sales perspective and that's going to take some time then to drum up the clients and get things going again.

What I love and appreciate about VIP Days, whether you want to do them as the only thing you do, as a transitional offer, or something like that is that you are spending equal-ish amounts of time marketing, selling, and delivering. That's this well-balanced business model to where it's not going to give you a sense of like, “I can just chill and not worry about things,” but it's also not going to cause you to go into a spiral when you have to do marketing and sales.

I think that for a lot of people, it gives this nice balanced-ish business model for them to where then they are able to still have loads of time in their month but I hate to see when people lose monthly retainer clients because we see it time and time again and it's really unfortunate. It causes people to go into a really intense spiral.

Racheal Cook: I think this is a challenge that is not unique just to service providers but what I tend to see is many of the people who we think of as behind-the-scenes service providers tend to be very referral based, and if they only need a handful of clients for the whole year as a retainer, they don't have enough referrals coming in to easily replace a high-end retainer client. That's where it becomes a challenge.

If they don't learn how to do the marketing side of things and have some marketing going, they lose a client and it could be a while before they can replace them or replace that income. You make such a good point there with adding in this one-to-one ratio of marketing to delivery will help offset that fear of losing out on revenue when unpredictable things happen. That's just part of business.

Jordan Gill: Yeah, exactly.

Racheal Cook: I'd love you to tell us a little bit as we are heading into this season for you, you've been hosting this amazing virtual conference for a little while now. From what I've seen from it, it's been really fascinating to get in and hear from you talk about VIP Days and why they can make such a difference. Can you tell us a little bit about the upcoming virtual conference?

Jordan Gill: Oh, yes, I can. I say that all of my events are my favorite, because we do some internal client events, but this is our only external client event that we do from a marketing and sales standpoint. It's great because, again, it makes sense from my energy capacity standpoint. Every six months, I pop out for two days and host this event and then I go back for five months and chill or really plan for the next one.

But the virtual conference is a vortex for two days where we virtually meet for about six sessions a day and we go through day one is about structuring your VIP Day and then day two is about selling your VIP Day, again, that well-balanced, people are like, “Why don't you do a one-day? I'm like, “Well, could we squish it all? Maybe, but I just like the two-day format.” We are talking about some really deep topics this time which I'm really excited about.

A speaker that we have coming is Tara McMullin. She's one of my favorite business minds. I followed her for over a decade. She is going to be talking about the over delivery complex that a lot of us are subscribed to and how it's actually not serving us. I'm super excited for that conversation because I'm an over deliverer, all of my people are over deliverers, and I'm like, “We must stop.” She's going to talk about that.

Then we have Regina of By Regina. She is coming to talk about thought leadership and really how each of us have thoughts that are really important to get out in the world and yet we are hiding them or we are coming from a minority point of view and so therefore we don't feel like it matters or that it will make any difference.

I'm really excited because I am just like, “Y'all, get out here and share your expertise. Y'all are so dope.” I'm sure you feel this too, Racheal, when you're with your clients and you just see all of their dopeness and then they just shy away from truly being able to make the big impact that they can make. This conference, I'm not holding back.

Racheal Cook: I love that. I think this is, again, more women need to make their message heard and make the impact they want to make. We have to start embracing that visibility. It comes with being uncomfortable and getting out of our comfort zone into that growth zone. It stretches us, but yes, absolutely, I'm so excited for those different topics coming up to amazing speakers. I know, of course, you'll be sharing a lot more about the how to's and getting a VIP Day up and running for your business.

Jordan, as we wrap our conversation, is there anything that you would recommend somebody think about if they are considering a VIP Day? Is there a question they should be asking themselves to determine whether or not it could be a fit for them?

Jordan Gill: Yes, great question. I would say that a few things to really look at are, number one, energetic capacity. I don't think people even process that because they're like, “I just see time on my calendar so, of course, I have the capacity for it,” and it's like, “No.” Think about your energy, think about how much you realistically have on a daily basis to do great work.

I'm really interested in working with people who want to work in their excellence, not just, “Oh, somebody will pay me for that,” not interested in that. If you want to do really great work and make big impact, then VIP Days are going to be awesome for you. Think about your energetic capacity currently, what you want it to look like for you once you get things up and swinging.

Then the second thing is what is the result that gives you a ton of joy and your clients a ton of joy. I think VIP Day should be a win-win for both you and your client, so do not, again, just do something that you think your clients will pay you for, do stuff that also lights you up because that's what we're in business for, for a win-win. But I see a lot of people doing it the other way, which I get why, however, it's not sustainable.

Racheal Cook: Absolutely. I think that's one of the biggest things I love about this is your clarity here on getting super focused on what you want to deliver, owning that 100%, providing that amazing value, and loving it while you're doing it, that is exactly what we all want to be doing in our business.

Well, thank you, Jordan, so very much for joining me. I can't wait for everyone to come check out the Done In a Day™ Virtual Conference coming up. I will have all the links and details in the show notes because it is coming up soon, y'all, that first weekend in September so I can't wait to have you guys dig into that. If you think VIP Days are an option for you and your business, or you're just VIP Day curious as Jordan has shared with me, this could be a great way to really sift and weigh if it's a great fit for you.

Jordan Gill: Yes. Thank you so much, Racheal, for having me on and I'm excited to see y'all at the virtual conference.

Racheal Cook: There you have it, friends. I absolutely love talking with Jordan. We had so much fun in this conversation and catching up before and after we actually hit record. But I know that this is something more people could benefit from. If you are someone who can turn out results really quickly, if you are someone that can accelerate somebody through a process, a VIP Day offer might be for you and maybe you'll find that like Jordan found, it frees you up to only work three, maybe four days a week, because you only have one-client facing day, the other days of the week are doing the behind the scenes or doing marketing-related activities.

I was super excited about this and will be continuing to very quietly work on my own VIP Day strategy, but part of me working on it is attending the upcoming Done In a Day™ Virtual Conference that Jordan is hosting on September 5th through 6th. I will be listening in on all of these sessions as she really digs deep, I mean today we barely scratched the surface, but she really digs deep and brings in these amazing speakers and her clients to share all the different ways they are using this VIP Day concept to move their business forward and to make their business more sustainable for their own preferences, their own lifestyle, their own calendar, so I'm really excited to be a part of it.

Again, you can get $10 off your ticket price by going to my link You will get directed to a special page with a special $10 discount just for you, just for listeners of the Promote Yourself to CEO Podcast.

I cannot wait to hear your insights and ahas from this, your questions from this. Make sure you connect with me over on Instagram, connect with Jordan at @systemsavedme on Instagram. She's not actively creating new podcast episodes but so much goodness back in the archives. I would still go listen to that whole podcast again. If you're into adding more VIP Days, I cannot wait to hear what comes out of hearing all about it. I hope you have a great rest of your day and we'll talk soon.

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