Have you ever thought of posting a project to Kickstarter? Inventor Ryan Grepper and his COOLEST Cooler have quite a few lessons for us about perseverance, timing, and content. Ryan’s first COOLEST campaign in December 2013 wasn’t successfully funded. His revamped campaign that launched this month was successful and funded at 13,676% of its goal! I studied Ryan’s two campaigns and this is what I learned that I will apply to my own Kickstarter projects. I hope these insights help you, too!
1.) Timing matters
Ryan’s first campaign for his cooler was timed to hit around Christmas time. Few people are thinking about coolers during the winter months. Timing his new campaign in July, prime time for summer products, worked much better. Also, holiday time is an expensive time of year for people with gift giving and this impacted his ability to raise the needed funds.
2.) Keep the total as low as possible
Ryan wanted to raise $125,000 the first time. His second campaign had a total of $50,000. Consider how much you really need to do a project, not how much you’d like to have.
3.) Get to the point
On Kickstarter, get to the “what” as soon as possible in the description. Explain the product clearly and succinctly with features prominently placed as soon as possible in the description. Put the detail further down in the write up.
4.) Have clear rewards
It’s common for Kickstater giving levels to have different rewards. Make sure those rewards are clear and listed early on in the general description.
5.) Have FAQs and answers
Think of likely FAQs that people may have about the campaign and answer them on your page.
6.) Be conscious of giving levels
Think carefully about the number of giving levels you have and the range of the options. Kickstarter’s community is filled with people who can give modest amounts of money so make sure to have plenty of opportunities for support at the low and mid-tier giving levels.
7.) Keep shipping simple
Many people, myself included, feel cheated when it comes to online shipping. The original COOLEST campaign had complicated language concerning international shipping. In the second campaign, that language is cleaned up and that seemed to have an impact on the number of international supporters.
8.) Don’t give up. Learn and revamp!
I love that Ryan didn’t give up on his idea nor on the Kickstarter campaign just because the first time wasn’t successful. He asked a lot of questions, reflected on his experience, learned, and tried again. After all, you can’t beat someone who doesn’t give up!
Congrats to Ryan and his COOLEST team! Have you run a successful Kickstarter? What advice do you have for readers?
IN BRIEF
Author, journalist, digital product manager, and licensed New York City tour guide. Creator and host of NYC's Secrets and Lies. Alumna of the University of Pennsylvania (BA), the Darden School of Business at the University of Virginia (MBA), Arizona State University (Biomimicry), and the University of Cambridge (MSt in Sustainability Leadership).
I build digital media platforms, report on urban climate resilience and biodiversity, and produce live narrative experiences that connect communities to history, nature, and place.
THE DEEP DIVE
My work centers on a single thread: building systems and stories that foster deep connection to our shared world. Across digital streaming, environmental reporting, and live civic storytelling, I design experiences that help people understand complex ideas and the environments around them.
DIGITAL PRODUCT STRATEGY & MEDIA LEADERSHIP
At Carnegie Hall, I serve as Digital Product Manager, leading product strategy, operations, and technical delivery for the video streaming platform Carnegie Hall+. I translate artistic mission into scalable, high-performance streaming architecture that reaches audiences globally. Previously, I led agile product and delivery teams across operations and compliance at American Express, managed Broadway theatrical productions and national tours, and guided strategic initiatives across cultural institutions.
ENVIRONMENTAL JOURNALISM & AUTHORSHIP
As a freelance journalist, I investigate how living systems, urban infrastructure, and human culture intersect. My reported features on urban decarbonization, biodiversity, coastal resilience, and biomimicry appear in publications including Smithsonian Magazine, The Washington Post, Mongabay, Natural History Magazine, and Foreign Policy Magazine. In fiction, I write the Emerson Page young adult novel series, alongside upcoming historical fiction and nonfiction works on New York history, mythology, and human resilience. I also write Togetherhood, a LinkedIn newsletter focused on urban ecology and community restoration, and co-host the podcast Frameworks in the Wild.
LIVE EXPERIENCE & CIVIC STORYTELLING
As a licensed New York City tour guide and live event producer, I transform urban landscapes into shared narrative encounters. I created, produce, and host NYC's Secrets and Lies, an interactive live storytelling series staged across cultural landmarks including the New York Transit Museum, the South Street Seaport Museum, and the historic tall ship Wavertree. I also design and lead site-specific walking tours exploring coastal ecology, food history, and neighborhood evolution, often with partners at Climate Week NYC and the Natural Areas Conservancy.
DOUBLE OR NOTHING MEDIA
Through my independent production studio, Double or Nothing Media, I develop ventures across media, ecology, and public history:
Digital Products & Strategy: Architecting scalable digital platforms, streaming experiences, and operational models for mission-driven institutions.
Environmental Reporting & Publications: Delivering long-form reporting, books, and newsletters grounded in climate resilience and regenerative design.
Site-Specific Live Storytelling: Producing immersive live shows and educational walking tours that engage public audiences in community history.
CONNECT
Website & Production Hub: doubleornothingmedia.com and christaavampato.com
Newsletter: Togetherhood on LinkedIn - linkedin.com/newsletters/togetherhood-7273771832221089792/
Instagram & Threads: @christarosenyc
Emerson Page Novels: emersonpagebook.wordpress.com/
View all posts by Christa Avampato
3 thoughts on “Inspired: Lessons from Ryan Grepper and the COOLEST Cooler Kickstarter”
Great summary, we are launching in the next couple of months and I will definitely take these tips on board! James at ZestDesk.com
I wish I knew someone to recommend. I would suggest looking into the site Freelance Writing Gigs. You could post something with them and see who applies. Best of luck!
Great summary, we are launching in the next couple of months and I will definitely take these tips on board! James at ZestDesk.com
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I am interested in locating a kick starter campaign manager, can you give me a recommendation to a good consultant
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I wish I knew someone to recommend. I would suggest looking into the site Freelance Writing Gigs. You could post something with them and see who applies. Best of luck!
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