Ryder Kessler: CEO of DipJar

My NativeAdVantage:


I’m the CEO of DipJar, where we aim to enable cashless generosity by making tip jars and donation boxes for credit cards. I grew up in NYC and then went to Harvard, where I spent most of my time sitting in coffee shops.

I studied interdisciplinary social sciences — but more importantly, I got close to the baristas who made me my Americanos and mochas every day. I learned that the shift from cash to credit cards had meant a severe decline in their take-home pay as tips in the cash jar evaporated. Customers wanted to be generous but didn’t have a way to easily drop a dollar in a tip jar using their credit cards — that’s how the idea for DipJar was born.

After college, I worked at a couple of startups then began a PhD in English literature, thinking I might become a college professor. But as I continued to spend inordinate amounts of time reading thousand-page novels in cafes, I realized that the problem of cashless generosity had yet to be solved — and was in fact getting worse. That’s when I decided to put my PhD on pause and launch DipJar.

What do you do best?

Coming from a background in technology, I saw that companies would build products aiming to solve problems, but they were problems faced by only a small fraction of Americans — i.e. entrepreneurs in Silicon Valley. What DipJar does well is remembering that there are millions of other Americans out there — people who don’t need on-demand rides, groceries, and hotel rooms. They are the people driving the cars, packing up the groceries, and cleaning the hotel rooms for the apps’ users. We exist to enable the generosity that helps millions of low-wage service workers make ends meet and that helps countless charities and cultural institutions survive and thrive. As CEO, I make sure we keep the needs of these constituents at top of mind, and that we keep pushing forward to deliver real money into the pockets of those who need it most.

What makes you the best?

What we hear from our customers, and from givers who use DipJar to tip and donate, is that our product is remarkably intuitive. While lots of people are developing payment technologies for phones and tablets, DipJar focuses on the vast majority of Americans who use credit and debit cards, and we make technology that allows them to tip and donate with one step — just dip your card, and you’ve given your tip! Nothing to download; no buttons to press. This simplicity and ease of use informs everything about our product, and it generates a strong positive response from our customers and givers.

How will you stay the best?

Right now our focus is on getting DipJars to everyone who wants them, so we have to keep building a great product and being mindful of why we’re putting it into the world. We’ll stay on top by staying focused on that mission.  

What are your aspirations?

Right now, my personal goals are very tied up in DipJar — I’d like to be an effective leader who keeps my team motivated and unified, and I’d like to take the company to a place where our impact is not just measurable but massive.

Soon after we began our first pilot tests of DipJar, I walked into one of the cafes where it was installed and a barista said, “I’m so glad you’re here — my last DipJar payment covered my electric bill this month.” That was such a gratifying moment: my idea, now a reality, was truly improving the quality of life for this wonderful, hardworking woman. I want to make that experience the reality for millions of other beneficiaries like her. (And, down the line, I’d love to finish my PhD someday!)

What fascinates you?

In technology, I’m fascinated by the ways work is changing in response to the on-demand economy — and how labor is responding with a call for higher minimum wages. I worry that the solutions for the 1% don’t necessarily help the growing set of 1099 workers, and so I’m eager to see how regulatory regimes and savvy businesses rise to the occasion to provide support to these vulnerable Americans.

Otherwise, I still love 1000-page novels, and I think literature has more capacity than most undertakings to foster imagination, critical thinking, and empathy. I’m eagerly watching how changes in education challenge the centrality of the liberal arts and humanities — and I’m hopeful that they aren’t sidelined too much by testing-based standards in K-12 education and STEM and vocational focus in higher education.

I’m also fascinated by the ways simple interventions and incremental changes can improve lives just as much as major technological innovations. For example, I was just reading about how one hospital reduced medical error in treatment of newborns simply by changing how babies were named on their bracelets (http://www.vox.com/2015/7/25/9036393/hospitals-errors-nicu) — sometimes thinking creatively is just as effective as developing new technologies.

I could go on, but that’s a start!

Favorite Motto:

I’ll offer three.

1. About participation in society, I often think of the William Sloane Coffin Jr. quote, “To show compassion for an individual without showing concern for the structures of society that make him an object of compassion is to be sentimental rather than loving.” It is not enough to think sympathetically of someone struggling financially — we have to ask why she is struggling and make changes to society to improve the lot of those we feel for.

That’s what we try to do at DipJar: not just to pity those whose cash tips and donations have gone away, but to look at the context in which those losses are happening and work at a global level to address them.

2. About leadership, I think of Lee Iacocca’s management philosophy (which I actually first learned from Tina Fey’s paraphrase): “I hire people brighter than me and then I get out of their way.” That’s definitely the most effective way to build a great company, in my experience.

3. About building something, the most apt quote is one of Edith Wharton’s about writing novels. She said, in French, “Je rêve d'un aigle, j'accouche d'un colibri” — “I dream of an eagle, I give birth to a hummingbird.” Our projects are often so much bigger and more fully realized in our minds than they end up being in the world. It’s very hard to make something, whether it’s a novel or piece of technology! But we keep trying anyway.

Favorite People:

My family of course takes the top slot — my parents and brother are all in New York, and they’re the greatest mentors, cheerleaders, and support system I could ask for. My grandfather just turned 91, and he grew up in poverty, fought bravely in WWII, then launched a company that he ultimately took public. His model of entrepreneurship is what inspired me to start my own company.

Besides them, I think I’ve learned more from Edith Wharton, George Eliot, and Jane Austen than from any other sources — the world’s knowledge is contained almost fully in the novels of these women.

Favorite Places:

I’m a consummate New Yorker: there’s nowhere better to read a book and sip an iced coffee than Washington Square, and no better way to spend an afternoon than at the Metropolitan Museum of Art or an evening than at the Metropolitan Opera.

Favorite Products:

Apple makes phenomenal products, and I take to heart Steve Jobs’s point that great product development consists mostly of saying no to things — to great ideas and features that ultimately detract from a product’s simplicity and the clarity of a company’s brand. So, I love my iPhone and my Macbook Air.

Here in New York, this motto is most effectively followed by Levain Bakery. It makes just four kinds of cookies, but these cookies far surpass those of any other bakery in New York. My favorite product is the dark chocolate chocolate chip cookie.

Current Passions:

Playing with my fourteen-month-old nephew. Talking to DipJar customers. Catching up on fantastic TV shows. Finding time to read.