Startup Spotlight: DipJar

Oct 9, 2016

Startup Spotlight: DipJar

Oct 9, 2016

This week we talk with Ryder Kessler, co-founder and CEO of DipJar. DipJar enables cashless generosity via tip jars and donation boxes for credit cards.

GH: How did you build your team?

RK: After two years of pilot tests that helped prove out the value of DipJar to customers and investors, I convinced my phenomenal co-founder, Jordan, to give up his secure and well-paying job to join me. We raised some funding and then hired hardware and software engineers who knew much better than we did how to take us from prototypes and pilot tests to a truly scalable hardware, software, and payments company.

GH: What is the philosophy driving your company culture?

RK: DipJar is all about empowering causes to make a positive social impact and valorizing the labor of service workers – those same values drive our company culture. We strive to empower our team members to be autonomous, respected, and acknowledged for their contributions. And everyone here is passionate about the positive social impact DipJar makes.

GH: What is DipJar?

RK: DipJar enables cashless generosity via the first ever donation box and tip jar for credit and debit cards. As we’ve shifted from paying with cash to credit and debit cards, charities miss out on the donations that fuel their work and employees lose out on the tips that help supplement their hourly wages.That’s where DipJar comes in. It’s as simple as a donation box or cash tip jar, but with the technology to accept and pass along gratuities left with credit and debit cards. We’ve built a streamlined hardware and cloud payments infrastructure fine-tuned for this novel and unique approach to giving.

GH: Startup life is full of failures and ‘make it work’ moments – can you identify how you bounced back from one of yours?  (please identify the perceived failure as well)

RK: I started DipJar as a side project while in a PhD program, studying to be an English professor. After the first DipJar pilots were up and running, I was sure that I would be able to raise venture capital. Here were ten DipJars generating lots of new money for their beneficiaries, excitement from dippers, national and international press coverage, and hundreds of inbound requests. What VC wouldn’t want to throw a few millions dollars our way!? But once I started meeting with investors, I realized that they were (rightfully!) wary of investing in a part-time entrepreneur who knew a lot about Victorian novels but nothing about making hardware. I didn’t “bounce back” as much as “stick it out”; after a year and a half of slowly growing our pilots and grinding out progress, we were finally able to raise the money that got us on track to grow.

GH: What did you learn from your first customers?

RK: We piloted 20 DipJars before scaling up our production, and those early tests were critical. Businesses and nonprofits using DipJars loved the simplicity of the donation experience (just dip your credit or debit card, pull it out, and you’re done!). But they wanted more flexibility in setting the dollar amount of the dip, since those first DipJars were hard-coded for a single dollar amount. Donors and tippers also wanted more confirmation that their dip was successful – and more social signalling of their generosity.

That feedback absolutely informed the current product, which allows our customers to control and change the preset dollar amount, and which has visual as well as auditory signalling of successful dips.

GH: What has the Boston ecosystem provided you?

RK: DipJar started in New York, but Boston offered us the support we needed to grow. We were able to move from piloting our prototypes to building a scalable business because we were invited to join the portfolio of Bolt, the Boston hardware VC. Bolt is where we met the brilliant Jon Fraser, who became DipJar’s VP of Hardware. And folks from the broader Boston VC and angel community were excited to invest in DipJar, whereas New York and SF investors were much more wary of the hardware component of our business.

GH: What was your Eureka moment: how did DipJar get started?

RK: I had the idea for DipJar talking to a barista at my favorite coffee shop. She told me that her cash tips had declined from about $4-$5 per hour to 50¢, all because folks had shifted from paying with cash to plastic. I realized how hard it is to be generous in a cashless world – whether it’s at the coffee shop, valet, coat check, church, museum, street fair, or gala dinner. And so I started DipJar to enable people to be generous (which everyone wants to be!) with the payment mechanisms they actually have in their pockets.

GH: What is the Boston ecosystem lacking in ?

RK: Though our hardware team, fulfillment center, and many of our investors are in Boston, the rest of our company is still based in New York. That’s more for personal reasons than business reasons: Boston just can’t compete with New York’s diversity and vibrancy.

GH: What is the best/worst piece of advice you’ve been given along the way? 

RK: This is startup 101, but the best piece of advice I got was from Ben Einstein at Bolt: “Hire slow, fire fast.” DipJar has made soaring progress when the right people were on board; our times of struggle have always been due to having the wrong person in a role.

Team is everything – especially if you’re doing something you haven’t done before (like being an English Literature academic starting a hardware and payments company!) – and so being cautious about team-building and swift about removing people who aren’t the right fit is everything.

GH: What was the best thing that happened to you last year?

RK: More than any single moment, it has been so edifying and energizing to see DipJar making real impact for the causes we serve – whether they’re national organizations like the Salvation Army, United Way, and Boys & Girls Club of America, or local causes like the Los Angeles County High School for the Arts, AbleGamers in West Virginia, or the New York Public Library. Seeing DipJar help fund education, health, faith, arts, and community programs makes all the work we’ve done worthwhile.


GH: What does the future hold for DipJar?

RK: We’re going to keep expanding the reach of our technology to enable as much generosity as possible. We’re also excited to offer additional tools to our nonprofit partners to help them optimize their offline and online collections and work more effectively with their donors – stay tuned!
Learn More about DipJar at
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