Cherry Picked!

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

January 5, 2021 Judd Lillestrand

Highlights From 2020

It's time for another annual recap. There's no way around it: 2020 was a rough year for most of Check Cherry's customers. A prolonged pandemic, restrictions on gatherings, and general uncertainty resulted in fewer bookings for our customers.

Adversity aside, at Check Cherry, we were still able to make substantial progress in improving the platform during 2020. We're grateful for all the feedback and ideas you shared with us to make Check Cherry better. The pandemic shifted our development priorities, and I want everyone to know we worked hard to adjust and help you navigate the market's challenges.

Here is a quick recap on how we Check Cherry platform improved over the last year:

The Postpone Status

Our first feature in response to the pandemic came mid-March as cancelations and postponements started rolling in. We added a Postponed status for bookings. By marking a booking as Postponed, it made it slightly easier to navigate the pandemic, stay organized, and salvage one's current book of business.


Check Cherry now allows for your account to operate with multiple brands. While this feature had long been on our list of things to offer, the pandemic made it a higher priority because many of our savviest customers branched into other services to diversify their business and keep earning.

Contracts [Enhancements]

Getting clients to sign the right agreement is essential, and over the years, we've had many feature requests/ideas in this area. In 2020, now you can set up multiple contracts, insert data based on package or add-ons purchased, and dynamically add merge tags—essential features for those operating various brands and offering unrelated services.


Check Cherry is excellent at helping service entrepreneurs stay organized. With Checklists, you can build multiple lists for each booking automatically. This feature is perfect for creating pre-bookings todos, equipment checklists, and deliverable reminders. You can also add a list for your clients to help guide them through the process of working together.

Google Calendar Integration

A lot of Check Cherry customers operate their business while holding a full-time job or earning elsewhere. Check Cherry's Google Calendar allows solopreneurs to automatically block off company availability based on events they add to their Google Calendar.

Mini Sessions [Enhancements]

This fall, we received a lot of great feedback on the mini session scheduling features of Check Cherry. We reworked the feature in many ways to make it easier to use, more powerful, and more integrated into Check Cherry.

Message Queue

We believe business automation helps people free up time to connect on a more personal level with clients. You can now automatically generate an email or SMS/text messages for a booking but hold it in a queue for later review. At that point, the message can be manually reviewed, edited, and send out with a click by personalizing messages to a client meaningful impact on their effectiveness. 

New Online Scheduling Modes

The pandemic resulted in more of our customers offering services that are not anchored by an inflexible event/wedding date. People needed a way to let prospects easily browse their availability online before picking a date. We're happy to say Check Cherry now offers customers the ability to choose slots and tools for you to specify slot availability.

Booking Engine [Enhancements]

Online booking and scheduling are core to Check Cherry. In 2020, we were able to focus a bit more on the booking engine. You now have more control over the look and feel of the booking engine colors so they can better match their brands. One can direct someone away from online booking and into a traditional Contact From to collect leads for high-touch sales such as corporate bookings.


It's common for our customers to provide services at the same places throughout the year, from popular wedding venues to their favorite photo shoot locations. Customers can now store those places in Check Cherry and add pubic and private notes. One can even include Places as a step in the online scheduling process, allowing clients to select a location while booking online which is great for booking photography clients online.

Calendar Refresh

The calendar is one of the most used features of Check Cherry. We distilled years of feedback to rethink how to make it better, from seeing Leads on your calendar to spot a hot date to better search capability and even some helpful filters to find specific bookings.

SMS Messages

We consistently received feedback from customers who wanted to send SMS/text messages just like they send an automated email. I'm happy to say in 2020, we got it done by integrating with Twilio to send the messages. Now one can send important staff reminders, proposal invitations to clients, and any of the other hundreds of combinations that else Check Cherry's powerful messaging automation provides.

Proposals [Enhancements]

Check Cherry's proposal system is simple, elegant, and highly effective. It's a feature that is heavily used to generate sales, and we made it even better in 2020 by adding the option for a client to choose add-ons and/or backdrops before accepting the proposal. Also, Proposals can now show staff members assigned to work the booking to help make a human connection and drive more sales.

Hourly Add-ons

Our customers frequently vary the price of services based on the length of a booking/event. We added a new option allowing add-on pricing to be calculated on an hourly basis. 

A bunch of smaller tweaks and changes

There were over 1600 commits/changes to the CheckCherry platform in 2020. Many of those changes were small tweaks or improvements to the underlying platform, which most people will never explicitly notice. However, all those little changes add up to help make Check Cherry easier to use, more powerful, more reliable, more enjoyable use as a customer, and more fun to build as a developer.

Looking at 2021

Internally, we're optimistic about 2021, the COVID-19 vaccine is rolling out, and we expect to see pent-up demand for our customer's services emerge in the coming months. The pandemic has really highlighted the value of getting together and the incredible role it plays in everyone's well-being. 

Thank you for the continued support and for allowing us to play a role in helping you grow, manage, and delivering fantastic client experiences. 

Good Riddance 2020. Happy New Year! 

January 3, 2021 Check Cherry

10 mistakes photographers make when redesigning their website.

At Check Cherry, we see a lot of fantastic photographer websites. We also see our fair share of websites that are in desperate need of a redesign. Below is a list of the most common mistakes people make when building a photography business website. There's good news if you are making one or more of these mistakes. The fix is easy, and it will increase your website's effectiveness and sales.

 1. They make the home page about themselves.

Your home page is the most important page of your website. Avoid making your home page feel like an "About Me" page. The best home pages introduce the services you provide because it helps people quickly understand if they should keep scrolling or hit the back button. Your website should serve people looking to hire you.

2. They let a website template control the direction.

Starting with a template is helpful—however, don't let it limit your website's flow. There are so many great website builders out there; be sure to find something that works for you, even if it costs a little extra.

3. They’re not transparent enough.

A website's purpose is to help you sell more. The best way to facilitate this process is to make your website the most helpful resource for people who want to book you. When you give people everything they need to make a good decision, you attract more of your ideal clients and spend less time fielding questions from people who aren't a good fit. 

💡Remember, the goal is not to be a fit for everyone. Instead, you want to attract people who understand your value, appreciate your service, and will spread the word by telling friends.

4. They don't list pricing and packages.

If all goes well, people looking at your website will think: "I like what I see. How much and what's included?" That's a great thing because it's the next step in the buying process. It can also happen without you having to lift a finger. Publicly showing people your packages and pricing keeps the buying process moving for 100% of the people who visit your website, not just the small percentage who reach out and ask for more information. 

 5. They use too much text.

Very few people will read your website from top to bottom. Avoid large blocks of condensed text. If you have a lot to say, break it up with headlines so people can scan and quickly find out what a section of your website is about before reading it.

💡Remember, most who visit your website are looking for a few simple things. People want to see your work, your package, and your pricing. If all goes well, they will want to book you online.

 6. They use too many images.

Avoid making your website just a digital portfolio. While you certainly want to show your amazing work, there is a lot more to the story and often people will be confused about what to do next. You'll also miss out on some basic SEO and get a lot of the same questions.

7. They focus too much on making a beautiful website.

Your website needs to look great. But it also needs to be effective and easy to use. Do not sacrifice a fancy website for one that leaves people with more questions than answers. Confusion is the enemy of sales, and the more straightforward you can present your services, the better. Common signs your website is too fancy include lots of movement, hidden content with slider sliders, slow loading pages, confusing navigation, and a general lack of direction for the visitor.

8. They use weak calls-to-action.

You need to help people know where to go next if they want to continue the process of hiring you. All too often, we see people only use the "Contact Me" call-to-action, which leads to a page with a web form. Don't be shy about sprinkling in more direct calls-to-action throughout your website to remind people you are ready for their business. Effective calls-to-action for photographers are "View Packages", "Pricing" and "Book Now”.

💡 Remember, your calls-to-action should stick out like a soar thumb. Make them big colorful buttons with easy to understand intent. 

9. They show lengthy testimonials.

One of the best ways to communicate with a new customer will have a good experience sharing testimonials of past clients. It's important not to overdo it. Feel free to take a few sentences out of a long one to shorten it up. Bump up the font size so it's easy to read. You only need a few and you can sprinkle them around your website so people are sure to see them.

10. They don't offer online booking.

If your website does its job well, people are going to want to know how they can book you. Clients love the convenience of online booking. It also makes you look like a true professional. A proper online booking system for your photography services will make picking a package, scheduling a date, signing a contract, and paying a deposit effortlessly. After all, when you are easy to book you get more business.

December 9, 2020 Judd Lillestrand

Mini Session Ideas [Inspiration]

Running a successful photography business often means developing a steady flow of business throughout the year. While your bread and butter may be seasonal, you can fill in your calendar with back-to-back mini sessions throughout the year. They're a great way to bring new people into your business and open up the opportunity for more sales down the road.

We've curated a list of mini session ideas to get inspired and offer something people in your area are going to love.

New Year Eve Mini Sessions

People love posing with props displaying the new year. Be sure to bring glitter, gold, and your sequin backdrops. Champagne flutes with cider also add to the feeling of celebration.

Valentines Day Mini Sessions

Perfect for new and longtime couples. Promote this one as a great gift. Red hearts, balloons, and flowers make perfect props. A simple white backdrop will make the rest of the colors pop. 

4th of July Mini Sessions

Show your spirit and be sure to bring in the red, white, and blue. American flags and rustic will fit right in. Bandanas, sunglasses, and handheld flags make great props.

Easter Mini Sessions

Stuffed bunnies, yellow chicks, and giant Easter eggs can make for a great backdrop.

Carousel Horse Mini Sessions

Pick up a vintage carousel horse for the kids to sit on. You might need to paint it, and our/mount it. If you do it right, you can rent out to other photographers and earn.

Rocking Horse Mini Sessions

The bigger, the better. Maybe even make it a unicorn. Consider adding pillows and pajamas to the mix.

👋 BTW, Check Cherry offers some great software for booking mini sessions online.

Lemonade Stand Mini Sessions

It's every kid's first business. Build a wooden stand, serve some lemonade, and capture the wholesome goodness.

Red Wagon Mini Sessions

Pick up a vintage radio flyer red wagon. 

Pedal Car Mini Sessions

Those old pedal cars are too cute. 

My Favorite Toy Mini Sessions

This one is an excellent way for parents to document their child's favorite toy. Be sure to ask people what they are bringing, so you know what to expect. 

Gone Fishing Mini Sessions

Grab a few old fishing poles and catch some cuteness. A wooden pole with a string and fake fish can be magical for toddlers. For older kids, you might want to have some cute hats and small fishing rod as props. 

Pet Mini Sessions

People love their pets, and it's fun for people to bring them to a photoshoot and mingle with other pet lovers. Consider partnering with a local animal shelter to get the word out. You might even want to donate a portion of the proceeds.

First Day Of School Mini Sessions

Grab a small chalkboard for parents to write the child's name and the grade they are entering. Include some apples, staplers, books, and a globe for props.

Sweet Stuff Mini Sessions

Make a candy bar with beautiful jars and color-coordinated treats. Giant lollypops and vintage popcorn bags will be popular.

Holiday Card Mini Sessions

Everyone needs that perfect picture for their Holiday Card. This mini session sells so well some choose not to offer it and instead do short sessions.

Pumpkin Patch Mini Sessions

Bring out the pumpkins of all colors, stack the hey barrels and throw in some rustic wood. A wheel barrel is a great option. Consider partnering with your local pumpkin patch early in the season.

Suggested Article: Fall Mini Session Ideas

Do you have a great example of one of the mini sessions we listed? We'd love to show your work and promote your business with a link. Just start a chat with us to get started.

September 24, 2020 Judd Lillestrand

Mini Session Packages & Pricing [Tips and Tricks]

Mini sessions present a fantastic opportunity for portrait photographers to earn more, attract new customers, and build their portfolio. They can also be a great way to get your name out there and reengage with past clients. What is a mini session?Mini sessions are miniature versions of the full photography sessions you already offer. They are less expensive, shorter in length, and produce fewer final photos for the client. To make them profitable, photographers often group several slots back to back on a single day and location.BTW, Check Cherry has some nifty features for scheduling mini sessions and promoting them to your audience via email or social media.When should I offer mini sessions?There are no set seasons for mini sessions.

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August 20, 2020 Judd Lillestrand

Custom Branded QR Codes

Let's face it: QR codes are rather ugly. I suppose it's one of the reasons I've never been a big fan of using them, especially for customer-facing purposes. However, QR codes are a handy and downright amazing technology. With the COVID-19 Pandemic lingering, they are being used more and more by photo booth software providers to aid in contactless photo booth experiences.Have you ever wanted to add your branding within a QR code? We'll there is an awesome website which does just that. Just upload your image, add some text, and it will generate a QR code.Have fun!

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July 29, 2020 Judd Lillestrand

How to book your first photography client online [8 easy steps]

Too many people who visit your website never book. That's why we wrote this helpful guide to help you book your first photography client online.When you offer the convenience of self-booking online booking from your website, you'll get more bookings and better leads. That's because you make life easier for both you and your clients. By showcasing packages and pricing, you'll modernize your booking process and make it easy for people to know if they are a good fit for your business. Here are eight easy steps to get your first online booking:1. Create PackagesPackages make it easy for people to evaluate, compare and pick the best option for their needs.

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May 8, 2020 Judd Lillestrand

Photo Booth Business Checklist

So you're looking to start a photo booth business. We've got you covered with a checklist of things you'll want to consider as you progress from the initial inception to your first successful paid photo booth customer.Evaluate ViabilityTake some time to evaluate why you want to start a photo booth business. Are you happy in your full-time job and looking for extra income? Perhaps you're unhappy with your current employer and looking to transition to running your business full-time. You might want to supplement your existing business with a new service.Market ResearchIt's a good idea to look at your potential competition. Do some google searches for "photo booth rental NEARBY-CITY-NAME" and see what comes up.

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February 17, 2020 Judd Lillestrand

Photography Contracts, Signatures and Deposits [General Guide]

Running a successful photography business means you'll be doing business with a lot of people. As your business grows, you'll move on from doing business with friends, family, and friends of friends to doing business with strangers. This article will cover the importance of requiring all clients first to sign an agreement and pay a deposit.Why should I make clients sign an agreement?A solid photography contract will spell out all the terms and conditions of your services. It's common to have not have covered everything during the sales process. For example, photographers often include a model release, allowing them to use photos from a session in their marketing materials.

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January 30, 2020 Judd Lillestrand

The Most Popular Photo Booth Backdrops

A lot of business was done using Check Cherry's photo booth booking software in 2019. We thought it would be helpful to analyze and share some of the data with the community. This article will be helpful if you are new to the industry and looking to buy your first backdrops. After all, you'll want to get the most bang for your buck. For those more established, it may be helpful to get an idea/confirmation of what the market is doing. Perhaps you're missing out on an important option, or maybe you need to diversify so you can stand out from the crowd. Be sure to look at the smaller words below; you might spot an upcoming trend.This word/tag cloud is based on the name of each backdrop selection that happened on Check Cherry during 2019.

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January 23, 2020 Judd Lillestrand

See All Competitor Facebook Ads [Marketing Hack]

Have you ever wanted to see what your closest competition is doing with Facebook advertising? In this article, I'll show you how you can browse the ads of your competitors and cover some ways this information can be helpful and also how it might not be so important.A few things before we get started:The search covers all Facebook platforms, including Instagram.You can search by the name of a Facebook Page to see results.Only active ads will show.One does not need a Facebook or Instagram account.About Ad LibraryFacebook has been under meaningful pressure related to its business model, privacy policies, and the impact of advertising on social issues, elections, or politics for its platforms.

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