Startup Spotlight: DipJar
Startup Spotlight: DipJar
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?
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.
GH: What has the Boston ecosystem provided you?
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 ?
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?