Cherry Picked!

Hand-selected articles, guides, and more from the makers of Check Cherry, designed to help your business grow and flourish.

January 13, 2020 Judd Lillestrand

2019 Highlights

I'm proud of all we accomplished in 2019 and motivated by the excitement and appreciation of our customers when they see each new iteration of Check Cherry.  In my recap of 2018, I wrote Matt and I both felt that 2019 was going to be even better than in 2018. I'm happy to share, our instincts proved to be accurate. While it's been a lot of work, it's also been a lot of fun to see Check Cherry continue to mature and help more people.

Our customers are continually sharing feedback while they use and implementing the Check Cherry's style of a CRM or booking management system into their business. I want to give a HUGE thank you to all of those who took the time to provide feedback (big and small) to help make the platform better. Check Cherry has come a long way and is in a great spot; however, we recognize there are still a lot of ways to make Check Cherry better. Please keep the feedback coming.

On to the recap of 2019:

We rolled out a series of features allowing customers to manage the availability of their company, packages, staff, equipment, and more. Included was an innovative feature for bundling items together and capping its availability. This bundling aspect of Check Cherry allows for more complicated configurations, such as managing the availability of double-sided backdrops or a set of equipment often included as a package.

We developed an official solution allowing customers to send proposals to their clients. A simple, yet highly effective implementation, the proposals feature compliments the self-service booking side of Check Cherry extremely well.  It's been heavily used and we received a lot of feedback leading to several iterations over the year.

With mini-sessions, you can offer several short slots for customers to choose within a given time frame. Minis are popular in the world of portrait photography and helpful for booking short sessions at your studio. We think they will come into play for other customer profiles of Check Cherry, just as photo booths in the years to come.

We released and reiterated upon a robust integration with Zapier. This feature gives customers more options for integrating their Check Cherry account with over 1,500 other applications. For example, one can easily sync their customer list with the mass/bulk email service provider of their choice such as Mailchimp or Contact Contact.

We continued to improve the Design feature. Enhancements include integrations with the PBO Design Shop and Photo Booth Talk.

From the time of our public launch in late 2016, integrating with Square was a common feature requested. In 2019 it made it to the top of the list, and customers can now choose among Stripe, Square, and PayPal to process card payments.

With widgets, customers can embed components of their Check Cherry account directly within their marketing website. Widget options include backdrops, add-ons, staff profiles and more.

Email Events
There is no more guessing if a client opened or clicked an email. Check Cherry now reports back the following actions for each email sent: delivered, opened, clicked, bounced, dropped.

Some of our customers are required to collect a different sales tax rate for each address/venue they provide services. With Check Cherry's TaxJar integration, customers can now automatically set an accurate tax rate based on state, county, city, and special districts.

Travel Fee Enhancements
We improved Check Cherry's feature set around Travel Fees. Customers can now scope Travel Zones on a package-by-package basis, add a custom address for each to calculate the distance and prevent self-service bookings that fall outside their travel zones.

Multi-package Support
One can now add multiple packages per booking/proposal. This is a great feature for those who offer multiple services (e.g., Photo Booth and Photography) for one client event such as weddings or corporate parties.

Staff Account Enhancements
We added extra permissions for staff accounts allowing admins to limit access to pricing and other actions of standard accounts. One can also now specify and customize the title/role of staff accounts for each booking. 

Calendar Refresh
Perhaps one of the most used features of Check Cherry, the calendar, got a refresh allowing one to see Confirmed Events, Proposals, Canceled Events, Company Time Off, and Staff Time Off in a single layout.

Improved Search
We leveled up some of the search features for Check Cherry to make it easier to find the booking, proposal, or design you're looking to work on next. We're indexing more data and leveraging best-in-class search technology for fast and forgiving lookups.

Override More Stuff
Over the years, we've come to realize just how important flexibility is when closing a deal. While Check Cherry is setup to auto-populate based on your business and package preferences, we spent meaningful effort to make it flexible. Allowing customers to override booking data such as the price of a package, price of an add-on or payment due date.

Hundreds of refinements, enhancements or fixes.
Looking back, there were a lot of smaller tweaks or enhancements which are not worth mentioning in this recap. However, all of those small changes add up to make a huge impact on how smooth and easy-to-use Check Cherry is for customers.

Our team is really excited about 2020 and where Check Cherry will be in 12 months. We're not satisfied simply creating a better mousetrap, we want Check Cherry to be something unique, innovative and to continually challenge the definition of what category of software Check Cherry falls under. We're so much more than CRM and while booking management will likely always be at our core, we have a few exciting features that have been on our wishlist for years and it looks like 2020 may be the year we get to push the envelope and see how everyone responds.
January 6, 2020 Judd Lillestrand

Photo Booth Rentals & Sales Tax [General US Guide]

Just about every state in the union imposes some form of sales tax. Among the few states who do not, some of them allow local counties, cities, and municipalities to tack on their own rates. As such, be sure to doublecheck because you may still be required to collect on that next booking.

The intent of this guide to help you quickly understand some key concepts related to sales tax and how they might impact your photo booth business. It's important to note: taxes in the United States can be complicated, making compliance painful for small businesses. Often some areas need interpretation. After reading this guide, you'll have a better understanding of several important concepts. You'll be better prepared to speak your accountant or tax advisor to develop a game plan for complying with the laws which apply to your business. You can also reach out to your local taxing authority for guidance. 

Over the years, we've added several features to Check Cherry, our Photo Booth Management Software, to help customers easily comply with the requirements for collecting sales tax. From tax settings on each package/add-on to our integration with TaxJar, which allows you automatically calculated the proper sales tax rate based on the address of each booking.

Essential Sales Tax Concepts

Sale Tax vs Income Tax

First off, keep in mind sales tax is separate from the income taxes you will pay each year as the result of operating your photo booth rental business.

Specifically, a sales tax is a consumption tax on goods and services — services such as providing a photo booth at a wedding or goods such as selling wedding party gifts to a bride. In the United States it is customary to have the sales tax paid by the consumer as a separate line item. As a business, you are effectively acting as an agent of the government and collecting sales tax from your customers. All monies collected will later be paid (remitted) to the government periodically. We'll cover more on remittance later in the article.

Because any sales tax you collect belongs to the government, it is essential one not use the money for personal or business expenses. Keeping the money is going to make fulfilling your obligation of remitting payment to the proper governing agency much less stressful.

Sales Tax Nexus

The first step in understanding where or not you are required to collect sales tax form customers is to identify where your business has a sales tax nexus. Your business could have a sales tax nexus in multiple jurisdictions. Furthermore, each jurisdiction may have different rates. 

While we often think of sales tax as being one percentage (that is how it will be presented to the consumer), sales tax is comprised of rates for multiple governing bodies such as a state, county, city, or municipality. For example, a bustling entertainment district of a city may have a higher tax rate to cover additional costs, such as extra police officers. It's possible for two addresses in the same city, state, postal code to have different tax rates.

Products vs Services

Some states choose not to tax businesses who provide services. For example, in Californa, plumbers generally do not charge sales tax because they are providing a service. Meanwhile, if you go to your local Home Depot and buy a new faucet, sales tax must be collected.

Destination Based vs Origin Based

In the world of traditional e-commerce (think, the concept of destination vs. origin-based is crucial. If a business sells online and is based in one state (the origin) but ships product to other states (the destination), it could impact the sales tax nexus for those transactions. I've seen photo booth rental companies interpret this in two ways:

1) The origin of services is the business's primary address, and the destination is the venue your traveling to provide your services.

2) The origin of the services you provide is based on the venue's address because the staff is physically operating at that location. This interpretation means you'll need to collect the state, county, and city rates based on each location where you provide your services. Effectively, your business will have a different sales tax nexus for each booking.

Sales Tax vs Use Tax

Use Tax is another concept worth noting. A Sales Tax is collected on behalf of the government by the seller. Conversely, the consumer of goods or services is responsible for paying a Use Tax directly to the government on qualifying transactions. A common example is buying a car out of state where no sales tax was collected on the initial sale. It's the government's way of preventing people from avoiding taxes and simply making big purchases across state lines.

Use Taxes are much harder to enforce, and it's why most businesses are saddled with the responsibility of collecting sales tax from consumers.

Digital and Tangible Transfers of Property

Another concept that may impact your responsibility to collect sales tax is whether or not you're are transferring property to the client digital or physically. You may operate in a state that does not require a sales tax on services where there is no transfer of property. On the other hand, as soon as you print photos or allow customers to text photos to themselves, a transfer of property may have occurred.


Any sales tax collected by your business must be paid to the government. Each state has different rules concerning the frequency and which jurisdiction (state, the county city, all three) one will cut the check.

For example, in Texas, it might look something like this: 

* Remit Monthly: if tax is $1,500 or more for the calendar quarter 
* Remit Quarterly: if tax is under $500 for the month or $1,500 for the calendar quarter 
* Remit Annually: if tax is under $1,000 for the calendar year with Comptroller authorization 

The Sales Tax Institute has a handy chart of each state's return filing thresholds for sales tax. It's worth noting you'll need to acquire a sales tax permit prior to remitting sales tax.

Sales Tax Exempt Organizations

If you find yourself collecting sales tax, you may be hired by a client who is exempt from paying sales tax. For example, in Florida, governmental entities (cities, counties, school districts, libraries) are exempt from paying sales tax. If a client requests to have sales tax removed, be sure to collect valid documentation such as a Florida Consumer’s Certificate of Exemption.

Speaking with your accountant or tax advisor to develop a game plan for complying with the laws which apply to your business is highly recommended. You can also reach out to your local taxing authority for guidance. 

December 27, 2019 Judd Lillestrand

Managing Availability For Online Bookings

Happy Holidays! 

Check Cherry now has more advanced features around the concept of managing your company's "Availability," so you can be sure you have everything you need before taking that next self-service booking. 📷📦💻✔️

Over the years, we've learned firsthand how service providers like you run unique businesses, and the standard inventory/equipment management concepts just would not have cut it for our online booking software. A big thank you to everyone who shared their feedback/thoughts with us and also for the patience while we devised a solution that is modern, easy-to-use and crazy powerful.

We packed a lot of stuff into this release and also created a video:

Below is a rundown to help give you an idea of what's new:

Company/Package Availability
  • You can now set the max number of bookings company-wide. A great/easy option for small operations, which are limited more by staff availability than they are hardware availability.
  • You can set availability based on specific hours of any given day of the week. The most common use case would be someone wanting to take self-service bookings for Friday evening, but not Friday mid-day (because they are working their day job).
  • Multiple bookings per day for the same packages/hardware. You can now offer self-service bookings and remain open for multiple bookings on the same day. Great for those who operate in a market with substantial corporate business, such as the Bay Area, where there can be many daytime bookings.
  • If you allow for multiple bookings of the same package on the same day, you can add a buffer between gigs to ensure you have enough time to tear down, travel, and set up for the next one.
  • You can now set booking limits at the Service, Package Group, and Package level. This is great for those who offer packages catered to specific customer profiles (wedding, corporate, etc.) but have limited hardware.

Add-on/Backdrop Availability
  • You can now manage the "availability" of your add-ons. This will be great for those who offer equipment rentals or add-ons where a physical item is tied with stints, such as an uplighting add-on or a giant Jenga set.
  • You can also manage the availability of your backdrops, including double-sided backdrops with our new "bundles" feature.

Booking Bundles
  • Great for managing the more complicated situation such as a double-sided backdrop, Booking Bundles allow you to create a new "Item" and then limit it's available.
  • Similarly, you can create a new hardware "Item" and bundle it with multiple packages. Great for adding something like two iPad booths and then tying them to 6 different packages.

Check/Test Availability
  • We snuck in a feature allowing you to check and test the availability of the various items listed above. This is great for testing while you are setting things up and also helpful for quickly determining if something is available.

Blackout Dates
  • You can now apply blackout dates to specific packages.

As usual, this is the first iteration and lays the groundwork for some related features and enhancements to come. Please keep the feedback coming: we love to hear the challenges you face and learn how you run your business.

Thanks for all the support and encouragement as we continue making Check Cherry better with each iteration. ✅🍒🚀
January 10, 2019 Judd Lillestrand

2018 Highlights

Looking back, 2018 was an amazing year for Check Cherry. With your help, we were able to continue improving the platform making it easier to use and more powerful. A sincere thank you to all of those who took the time to share their thoughts with us. Here are just a few things we accomplished together in 2018:Improved Tax SupportTax support in Check Cherry is rock solid. From managing different rates on a per event basis to allowing for only certain packages or add-ons to be be taxable. Your accountant is going to love what we did in 2018.PayPal PaymentsThis long requested feature finally hit production.

Keep Reading >>

August 13, 2018 Judd Lillestrand

Call-to-Action Guide [Tips & Tricks]

Most people who visit your website will never reach out to you. That's why your website needs to be the most helpful resource for people looking to hire you. By anticipating common questions, providing clear answers, and guiding people through each phase of the buying process your website will help you increase sales.Adding common sense calls-to-action on your website is the best way to help people find what they are looking for so you can keep the buying process moving even when you are not there to help.What is a call-to-action?A call-to-action (CTA) is text on your website, often a button itself or a short sentence with a link. They are designed to prompt someone to click and take action.

Keep Reading >>

February 21, 2018 Ross

7 Great Ways To Automate Your Photo Booth Business

I absolutely love the notion of keeping my customer experience consistent and saving time. This year I've really dialed up my customer automation efforts. I thought I would take a few moments to jot down some ways I'm automatically sending messages with Check Cherry for my photo booth rental and mobile DJ company, Local Boy. Generally, any email to the customer should be sent with intent to provide value and/or helpful information to the customer. Setting up automation is super easy, so don't feel overwhelmed. We have a video showing you just how easy it is to get started.The Proactive NotesI've been laying the groundwork for delivering an amazing customer experience by automatically sending out emails leading up to the event.

Keep Reading >>

February 15, 2018 Matt Goatcher

Feature Enhancement: One Click Lead Conversion

We hate busy work and are always looking for ways to make your life easier and create the best photo booth booking software. Now you can convert a Lead into a Reservation with a single click. Get more leads, close more sales, and grow your business with Check Cherry.While this may seem a small thing, we know it's the little things that count and add up to make one awesome service.If you want to learn more about Check Cherry's Leads, watch this video:A huge thanks to the Check Cherry customers who suggested this feature. We hope you love it!

Keep Reading >>

February 8, 2018 Ross

6 Ways To Increase Photo Booth Sales With Coupons

Coupons are an amazing tool to help grow a photo booth business. I've found some really good ways to use coupons at my business, Local Boy, and I thought I would share what is working for me so you can consider them for your business.Venue DiscountsDo you do business with a venue on a recurring basis? Create a special coupon with the venue's name in it. By including their name in the coupon code, they know it's exclusively for their customers and gives them another reason to recommend your service to others. If you want more venue business, try calling several in your area and and offer an exclusive coupon.

Keep Reading >>

February 2, 2018 Judd Lillestrand

Feature Spotlight: Messages

Automatically log email communication with your clients.We understand how important it is to stay on top of your event communication. While searching your inbox is one way to get an overview of your past communication, such a strategy can quickly breakdown if you have multiple people in your photo booth business and send attachments.With Messages, you start an email from within the Message section of an of your bookings, and all future communication will be logged automatically even if you respond directly via email.

Keep Reading >>

January 27, 2018 Judd Lillestrand

Feature Enhancements: Automated Emails & Coupons

Automated Emails can now be sent on a package by package basis.Good news! Check Cherry's Automated Email feature just got a lot more powerful. Now you can specify which packages will receive any given automated email. We think this is really going to be handy for those who offer multiple service types.There are a lot of reasons one would want to send automated emails. It's a huge time saver and can really help you deliver a consistent customer experience.

Keep Reading >>