In a rapidly advancing cashless society, the decline of cash transactions has had a significant impact on street-level charitable giving and the unhoused population. John Littlejohn, a former homeless individual, recalls the days when people would spare a few dollars to purchase a copy of Street Sense, a local paper that covers homeless-related issues and employs unhoused individuals as vendors. However, he has noticed a decrease in the number of people carrying spare change, with even well-meaning individuals unable to help due to the lack of cash on hand.

Recognizing the challenges posed by a cashless society, technological advancements are now coming to the aid of charitable groups and advocates for the unhoused. Street Sense has introduced a phone app that allows people to purchase the paper electronically, with the profits going directly to the vendor. This innovation, combined with Social Security and income from Street Sense and other side jobs, has enabled Littlejohn to secure his own apartment.

The decline of cash transactions in Western society has been a substantial shift over the past two decades. Initially, credit cards began to replace cash for even the most trivial purchases, and as smartphone technology advanced, cash-free payments became the norm for many. This shift has had a significant impact on street-level charitable giving, from individual donations to panhandlers and street musicians to the traditional red Salvation Army donation kettles outside grocery stores.

Sylvester Harris, a 54-year-old panhandler in Washington, laments the fact that most people now rely solely on cards or mobile payment options. While some individuals genuinely want to help, the prevalence of cashless transactions means they often don't have the means to contribute. The cashless world is particularly challenging for the unhoused, as many electronic payment apps require additional items such as credit cards, bank accounts, identification documents, or fixed mailing addresses - all of which are often out of reach for this vulnerable population. Charities have struggled to adapt to these changing circumstances.

To address this issue, the Salvation Army has implemented a system where donors can simply tap their phones on the donation kettle to make a cashless payment. Michelle Wolfe, director of development for the Salvation Army in Washington, reports that this new system has already resulted in increased donations. The minimum cashless donation is now $5, and donors frequently contribute as much as $20. However, this system is only available in 2% of the collection kettles in the greater Washington area.

Similarly, Street Sense had to adapt to changing consumer habits to maintain sales. Brian Camore, the executive director, explains that vendors reported potential customers wanting to buy the paper but lacking cash. In response, Street Sense licensed the technology for a cashless payment app developed by an affiliate paper in Vancouver. Vendors can now redeem their profits at the Street Sense offices, ensuring they still benefit from the sales.

The COVID-19 pandemic further complicated matters for Street Sense vendors. Firstly, the fear of transmitting the virus through cash exchanges led more people to avoid using cash. Secondly, the reduced number of people working in downtown offices - the paper's main customer base - significantly impacted sales. Thomas Ratliff, Street Sense's director of vendor employment, notes that commuters have always been the best customers compared to tourists. As a result, vendors had to expand their territories, traveling to areas like Silver Spring, Maryland, with steady foot traffic.

Ratliff has also taken on the role of tech support for vendors, helping them navigate the complexities of the modern online presence required for cashless transactions. Common problems include changing emails, forgetting passwords, and losing important documents. Some payment platforms like Venmo and Cash App are more unhoused-friendly, as they only require a phone number and email address, eliminating the need for a bank account. However, even these options can be challenging, as many vendors frequently change cellphone numbers, which can complicate the identity verification process on these apps.

In response to these challenges, some innovators have developed apps that not only enable cashless donations to the homeless but also connect them with support systems to help them transition off the streets. The Samaritan app, operating in seven cities including Los Angeles and Baltimore, allows donors to sponsor an unhoused person without using cash. Special cards containing a QR code are distributed to unhoused individuals, enabling individuals to donate directly to their account. The app provides mini-profiles of local unhoused individuals, describing their situation and immediate needs, allowing donors to contribute towards specific needs such as groceries, apartment deposits, or job interview-appropriate clothing. Jon Kumar, the founder of the Samaritan app, believes that personalizing the stories and needs of unhoused individuals makes it harder for people to ignore their plight.

As society continues to shift towards a cashless future, it is crucial for charitable organizations and advocates to embrace technological innovations to ensure that those most vulnerable are not left behind.