The Summer Cash Dip and Why It Happens
There is a specific kind of quiet that scares small business owners, and it is not the quiet of a slow, lazy summer afternoon. It is the quiet of their July bank account. Clients are off on vacation, nobody is starting anything new, and you can feel the summer dip coming the way you feel a huge storm before it lands.
I used to brace for that dip too. Now I don't, and the reason is one move that I make almost every single summer. I pre-sell my fall. I get the yes now while it is quiet. The deposit comes in, the contract gets signed, and the start date is set for September or October in the future. And then I actually get to enjoy my summer knowing that revenue is already on its way.
There is no more bracing, no September panic to fill up the calendar again. Because here is the truth most people miss. The summer cash dip is not usually a demand problem. It is often a timing problem. And timing you can fix. That is what this episode is all about. Let's get into it.
Hey there, CEO. Racheal Cook here, founder of The CEO Collective and host of the Promote Yourself to CEO podcast. I hope you have been enjoying the series all about setting yourself up for success this summer. We have tackled so many topics in the last few episodes, everything from doing a Mid-Year Review, making sure you looked back through the first half of 2026, and now you are looking forward at the second half.
We talked about reviewing your calendar and plugging in the notes to future me, so that you have reminders of commitments you are already making and you are protecting your time and your capacity. We talked about how the summer slowdown can affect us in our business, and how you can use this time to think strategically and work on the big picture strategy, work on upgrading the infrastructure for your business.
And we talked about setting a summer schedule so that you are putting some boundaries in place, clearly articulating them, and you are able to take some more time off and really enjoy this season. Well, there is one thing we have not talked about yet, and that is how to manage the revenue.
Revenue Strategies That Keep Cash Flowing
For a lot of small business owners, summer is a challenging season, because this is when they start to see revenues dip. And it makes sense. Just like we want to go do summery things and enjoy days at the beach and vacation and time with our family, our clients do too. They want to do all the summery things. They want to go on vacation. They want to take their time off.
This makes it a little extra challenging for small business owners, because that means it gives those potential clients a reason to not get started yet, to not sign up for our products, programs, and services. They do not want to make a commitment to something when they know they have a vacation coming up right in the middle of it. It makes it too hard to juggle all of those moving pieces.
But we need revenue, right? Unless you are going to focus on building all the revenue you need in the other nine or 10 months of the year so that you can live off of that during the summer season, then you need to come up with a strategy that is going to continue to have cash flowing in your business.
Now, there are a lot of different ways you can make sure that you still have revenue coming in the doors. Maybe you have retainers in your business, so you already have clients who are committed to paying you month after month after month. Maybe you have payment plans, and those payment plans are going to continue to be collected whether people are on vacation or not. But what if you need another strategy, another way to bring revenue in the door?
What Pre-Selling Your Fall Looks Like
Today I want to share with you a simple strategy that I give clients all the time. I give clients this every single early summer. Late May, early June, I start talking to them about this strategy, because you do not want to be white-knuckling it through the summer months. The simplest, easiest way that I know to help bring revenue in the door is to go ahead and pre-sell your fall.
Pre-sell your products, programs, and services to start in the fall. Here is what that looks like. You get the yes now, while it is a little quieter, which means the deposit gets paid, the contract gets signed, and the start date gets set for the future. It can get set for the end of August, September, October, whenever works for both you and your client.
You are locking in the start date in advance, and you are not starting the work right now. You are simply locking the date for them on your calendar, committing that you will start with them in the future.
Setting the Deposit and Start Date
The deposit can be whatever makes the most sense for your business. It really does vary from business to business. It could be 25% of the fee. It could be half. It could be a flat booking fee to hold the start date, or it could be just a first payment if you have payment plans. The point here is that you have real money changing hands, and you have a contract that is signed, so the commitment is real on both sides.
This is what a lot of small business owners do, and we do not always see it from the outside. Often, very in-demand service providers are booked months in advance, especially in the B2B, the business to business space. A lot of creatives that I have worked with in the past who do websites or branding or copywriting, or maybe they are running intensives or retreats, the opportunity to work with them is not that you can book and start right away. It is that you have to get on their calendar in advance, because they are that in demand.
But you can borrow this strategy. You do not have to wait until you have a wait list to do this. You can start booking people in advance right now. This is a great way to both build your demand, to fill your calendar and be booked out months in advance, and to manage your capacity and your calendar by intentionally deciding when those start dates are going to be.
When Proactive Selling Feels Pushy
Now you might be thinking, this feels a little pushy. I do not know if I like this. Reaching out to ask people right now to work with me, it just feels a little pushy. If that is your reaction when I am talking about booking people in advance and pre-selling your fall, then usually that indicates that you have some sort of belief that proactive sales is pushy, and we need to tackle that.
Because sales truly should be a win-win every time. If a sale is not good for you and your client, then it is not a sale worth making. If offering your product, program, or service feels pushy, then that is worth unpacking, because it usually means that somewhere in the back of your head you have decided that what you offer is an imposition, or that it is not as helpful as it could be, or not as valuable as it could be, as if those clients are doing you a favor by buying from you.
That is not true. You know that your clients appreciate the work that you do together. You know the results that they get from working with you. So your ideal clients should not experience you being proactive as being pushy. They should experience it as care and thoughtfulness, as leadership. They should appreciate it when you are looking out for them, when you are helping protect their time and helping them get the result they are looking for.
Protecting Clients From the September Scramble
Here is what you are really protecting your future clients from. The September scramble. The September scramble is when everybody comes back from the summer all at once. Suddenly school is back in session, people are hitting their routines again, they are ready to get back to their goals, they are back in work mode, and it is an intense few weeks.
For a small business that is not really ready for that, it can be incredibly overwhelming. It can make you feel behind, and it can also have you feeling like now you have to accommodate for every single person who waited until September to book you for the project they want done before the end of the year.
This whole series on the podcast has been about using summer strategically so that you avoid that scramble for yourself. And that also means helping your clients avoid that scramble. We want to think about how we are helping them be more proactive and achieve their goals, because that is what all of us are here to do, help our clients get the results they are looking for.
So the test is this. If your product, program, or service makes their life easier, gets them results, and is something they want to have done, or have started, or made meaningful progress toward before the end of the year, then your solution for them is, get locked into my calendar now so that you are not scrambling in September. That is a gift to them. That is not a hard sales pitch.
I have practiced this myself with The CEO Collective and with other programs that I have. I will often open early enrollment months ahead of a cohort actually kicking off. And I do this because my clients are like me. They are busy. They have busy lives, and their calendars get filled fast.
One of the hardest things is making time for a program like The CEO Collective, and this allows them the runway they need to block out time for the work they are about to do with me, before their calendar is completely filled up. This also lets them take a little bit longer with all of their onboarding, and that is actually a bonus for them.
For many of us, just the onboarding work, the prep work before they get started with the real work they have signed up for, that can be a lot. It can require a lot of time and energy. But when we pre-sell The CEO Collective for fall, then people have more time to get all that onboarding work done and send it over to me. I can take my time getting all of the strategy built out for them, so that they can walk into their first CEO retreat in September feeling ready, and not feeling like they have just scrambled through the first month headed into the fall.
How to Position the Pre-Sell
So what do you need to do? How do you position this? How do you talk about this to your clients? I keep it pretty simple and straightforward, honestly. I like to be really clear and honest with my clients.
Hey, I know that summer is a season you are taking some downtime, and it does not feel like the right time to get something started. And I also know that you want to have this done by the end of the year. You wanted to start this by the end of the year. You want to go into fall already with your game plan ready to go.
So you tell them now, do not wait to get on the calendar. Do not wait to start. The time to book is now, so the work is ready to go when you need it. Get on the calendar now so that you can plug everything in well in advance.
This is especially true if you are a service provider and there is something they are trying to accomplish before the end of the year. I will often hear people say they want to have a new branding photo shoot done by the end of the year. Well, guess when photographers are busiest. It is going to be September and October. If you want that done by the end of the year, you better get on their calendar now.
If you are saying you want a new website, or a new brand, or copywriting for a big program that you are planning to launch, you have to get in the calendar in advance, because that work takes time. Sometimes it can take months for somebody to go through an entire rebranding process or website development process. So you want to let them know how long that process takes, how much time it really takes, and encourage them to get it in their calendar now, instead of waiting until they are already in the season, their calendar is already getting full, and now they are trying to add that project on top of everything else.
Okay. So keep it simple. You can literally keep it that simple.
What Happens After They Say Yes
So what happens once somebody says yes? This is the next step, and this is the key to this actually working. What happens after they say yes? What happens after they send in the deposit and have signed a contract? And again, until they have sent a deposit and signed a contract, it is not real. We do not count that as a sale until both of those things have happened.
The next step is they get started with onboarding. Now, this should be a process you already have in place. For every single product, program, or service you have, you should have some sort of onboarding process for that client. I find this is especially important when you are booking things out in advance, because people want to know that they just made a smart investment in hiring you and working with you.
So you want to go ahead and send them what they need to prepare for the engagement. It does not matter if the engagement is not happening for two or three or four months. You want to go ahead and get them the prep work now, not the week before they start, when they are scrambling because September is crazy busy and they are trying to juggle a new school year and a new schedule and all the new things. You get it to them now.
Building the Onboarding and Timeline
Once they have said yes, the deposit has been paid, the contract has been signed, the start date is locked in. You let them know exactly what the timeline is going to look like. Here is your start date. Here is what you need to do before that date. Here is what I will do before that date. And here is when I will check in with you next.
You want to make sure they know there is another check-in that is going to happen before they start. You do not have to check in with them nonstop all summer long, but it is nice to pop in and give them a reminder, to make sure all their prep work and onboarding has been completed before the actual start date, especially if you need that in order to start on time.
A clear timeline is what makes people more comfortable paying now and starting later. It is what lets them know that you have a process, you are a professional, and you are going to handle everything for them and make sure they have exactly what they need to make this a successful engagement.
If you need homework or prep from them, have it built already. Have a system in place so that you can send it immediately. This is also where the pre-sell becomes a gift to clients, and I think this is so true for deeper level work that requires some thinking time. When they sign up to work with you well in advance, they get a little extra time to think through everything, and sometimes that can be really hard to do in a normal busy season.
Why the System Makes It Repeatable
So quick pause, because this is exactly where pre-selling your fall lives or dies. It is the system. Pulling off one pre-sale with a scramble of emails and a deposit link is doable. Making it something you can run every summer without reinventing it each and every time, that is a different thing.
And that is what we teach here at The CEO Collective. It is what we encourage you to do when you build out your Client Growth Engine, the repeatable system underneath your marketing, your sales, and your client experience. So pre-selling becomes something your business just does, not a heroic effort to bring cash flow in when you desperately need it.
We want you to start thinking like a proactive CEO, like a strategic CEO. That is what this bundle, the On-Demand CEO Retreat and the Client Growth Engine, helps you build. We are currently offering the On-Demand CEO Retreat and the Client Growth Engine at the lowest price it is going to be, and the price is going up. So if you want to get started and have more strategy underneath your business, have a clearer game plan for how you are going to approach Q3, we would love, love, love to support you.
Keeping the Outreach Simple
Okay. Now let's talk about how simple the outreach can be, because this is where you can really overcomplicate it. I know this is where a lot of people want to overcomplicate it. The good news is you can make this incredibly simple. So simple, you do not even need a sales page if you do not already have one. You can run the entire pre-sell with a handful of emails and a way for people to book the consult with you or put down a deposit on your calendar.
The core message you are sending to your audience is, I have a few spots opening in September and October. If you want X, Y, Z to be completed by the end of the year, here is how to get on the calendar now so that you do not have to stress about it while you are relaxing during the summer. Some variation of that.
Keep it simple. A few clear emails. You are describing what you are offering, the service. You are explaining what the results are, what the benefits are, how it works, what the timeline is. Maybe you are sharing some case studies in the emails, and then you share a booking link. Once they have that consult, you send them the deposit link and the contract. Or maybe they are just going directly to a page to pay immediately, and you do not have a consult process. It depends on how you work.
Who to Send the Pre-Sell To
Now, who do you send it to? You do not necessarily want to send it to your whole audience at the same time, especially if you are just looking to pre-sell a few spots. You do not have to send it to everybody. Maybe this is not an offer you run all the time.
I will often pre-sell one-on-one CEO strategy intensives, and that does not go to my whole audience. Often I can pre-sell that by making a curated list out of my audience. Here is what that means. The first thing I do whenever I am doing a pre-sale like this, or trying to sell something that is really for a small segment of my audience, I will start with the people who are the hottest clients.
What do I mean by that? I mean people who have already worked with me, my past clients, my current clients. Those people are always going to get first dibs on any opportunity to work with me that is not a public-facing opportunity. So those are the first people I am going to reach out to. And often I will send personal invitations to those people. I will even sit down and record personal video invitations, letting them know, hey, this is what I have available. I would love to work with you on this. Here is why I would love to work with you. I know you are working on this, that, and the other. If you want to learn more, here is the link to get all of the details, and let me know if this is something you would be interested in for the fall.
Working From Hottest to Coolest
So I will actually send out highly personalized messages to a lot of people. Does it take a little extra time? Yes. Because if I am talking about the one-on-one CEO strategy intensive I offer, that is a high-ticket offer, so I will take the time to send personal invitations.
Once I have sent out to my hottest list of past and current clients, then I will expand out to the next warmest layer, and that is people I have probably already talked to in some way. I have more familiarity with them. I know them, they know me, and I know this is something they would probably be interested in, but maybe they have not worked with me before. Maybe we have had a conversation. Maybe we had a sales call and they were not quite ready yet. They are still interested in working with me in some way, and maybe I just need to make the right offer. The last one was not the perfect fit. So again, I will send out personal invitations.
Then I will expand a little bit more. So you can see I am going from my hottest list of potential yeses, expanding out from the hottest to the warmest. Then I expand out a little further, and I am going to send it to my email list. Those are really my insiders. Those are the people who are usually the most interested in learning about working with me, because they have taken the additional step of hearing from me via email. I will go to them, and then I will finally go out to social.
If you hear about something on social, it is either a big public-facing launch, or it is something higher touch that I have not yet filled. Usually I like to focus on who is the warmest all the way to the coolest, and that allows me to send out a group of invitations. I will go to my hottest people over a few days. If none of them respond, or I still have some spots left, then I will go to the next layer, and then the next layer.
The people who already trust you are the most likely to book, and that early momentum makes the rest a little bit easier. One of the things you can often do is say, hey, you are on the hot list right now. You are the first one to hear about this. I have only got five spots available, and as of right now I have only sent this out to 25 people. Next week I am going to send it out to my larger list of clients, which is 350 people.
You can use that also as a way, as you are expanding from hotter to colder, to say, oh, I already invited my past clients to this. I filled three out of the five spots. I have got two left, and that is why the rest of my audience is hearing about it now. So you can think about that as a way to take this from just a couple of blasts to everybody to really tightening it up.
The more you can personalize the pre-sell, especially if this is a higher ticket offer, like a four-figure offer or five-figure offer, the more likely they are to actually be interested. Usually that is what really works for this, when we are talking about your higher end work. This is not pre-selling for a course that is a couple hundred dollars. There is no need to really pre-sell that. We are talking about things that are going to be more intensive, more time-consuming, higher commitment from the clients and higher commitment from you to deliver the product, program, or service.
Make Your List of Dream Invitations
So I hope this was helpful for you. I have talked through this with a couple of my clients. I have already seen them start to pre-sell everything from their highest ticket one-on-one offers to group coaching programs that have a start date in the fall. I have seen them do this to offer services they are going to start in the fall. I have seen them use this for retreats or workshops, things that people need to block out in advance.
Keep in mind that this move does not have to be complicated. It just does not have to be complicated, y'all. Make a list of your dream invitations. Your past clients, your current clients, the handful of people you have communicated with who you know are high interest in working with you, and you know they had wanted to get started, or they wanted to tackle this before the year is over.
Send them a personalized invitation, not an email blast, a personalized invitation. Is this still a goal for you to complete this year? I am booking now for people who need it by Q4. I am booking now for people who want to get this accomplished before the end of the year. And that could be the whole thing. A few emails to people closest to you, a way to book, a way to get a deposit, a way to sign the contract. You could have this running by next week.
So go ahead and try this out. I want to hear from you. How is this landing? Have you ever done anything like this for your business? I find that this is one of those simple things that, when you position it and really think of it as I am being of service, I am helping my clients block time for something that is high priority for them well in advance so that they have time to do it justice, I am helping them avoid their own September scramble, I am helping them make this a priority while they can still enjoy this season. It is such a win-win.
What's Coming Next Week
So next Thursday is the last episode in this series, and it is the proof that all of this can work. I am in Italy with my family for a month. In fact, I am there right now. I am recording this well in advance. I am sitting in Richmond, Virginia, as I record this. But we have almost a month in Italy with my family this summer, and I am going to tie this whole series up with a bow by sharing how I was able to keep the entire engine running while I am in Italy with my family. It is practical and magic at the same time. I cannot wait to dive into it. I think you are going to get so much out of that episode too. All right, I will see you then.