Why parts of Main Street reject Silicon Valley
When cash beats Apple Pay, and group chats beat SaaS
Cash-only in 2026
When I helped run our family’s restaurant a few years ago in Dallas, one of the most important decisions we made was to become a cashless business. Doing so saved us hours of time previously spent counting every dollar and penny in our cash register every night at closing, several trips to and from the bank, and a significant level of anxiety around safety and security. A small minority of our customers paid in cash, and a majority of them were happy to pay with a card if we asked them to, and we were content with missing out on the fraction of a percentage of customers who did not want to dine with us after we made the switch.
We felt way better from the very first day we made the transition. Workers felt much safer and more at ease being at and near the register, and because closing out took a few clicks instead of several minutes of counting currency after a long day, we were happy to go home way sooner than we used to be able to.
For us, it was an easy decision to make because the tradeoff was simple to calculate, clearly positive, and directly aligned with our culture.
I contrasted the calculus of the decision for us with a popular gas station that sells street tacos and only accepts cash.
The tacos are cheap and taste good every single time. The two locations closest to me are in perfectly convenient locations right off of major highways. I’ve never gone there to fill up my tank, only ever to get those tacos.
I also haven’t carried cash in my pocket for years, so it’s a bit of a chore to have to go to my bank’s ATM beforehand or pay a fee to use the ATM at the gas station, but it’s worth it every time.
It’s not like they don’t know about Square, Clover, or Toast. It’s not like they don’t know people enjoy paying with Apple Pay, Google Pay, CashApp, or Venmo. Funny enough, you can use credit cards and digital methods to pay for gas, car washes, and everything else in the attached convenience store, just not the tacos.
Why?
Maybe the few percentage points they save on processing fees are them taking a final stand to protect their margins. Maybe the taco shop has different ownership than the other services so they like to keep the economics separate by not mixing the POS systems. Maybe they’re just old school. Who knows.
What is more interesting is thinking about what would happen if they did start to also accept cards and digital payments or if they were to become completely cashless like we did.
Being cash only isn’t just a transaction currency decision for them. Doing so attracts a certain type of customer to come there. It also selects for a certain type of person to work there. It probably helps keep the prices low, further signaling to their target customer base that this place is for them.
Sure, you may not get as frequent business from people like me who like to pay with their phones, automatically rack up loyalty rewards, get text alerts when the food is ready, and get receipts stored in their email inboxes. But taking away cash only would threaten everything else that makes this place the perfect spot for the right person at the right time. They’re not looking to be all things to all people, and that’s refreshing in a world where I can go elsewhere to have a seamless digital experience (and likely pay as much for a bottle of water as I could for a few tacos from this spot).
We don’t need every restaurant to turn into a fully optimized, autonomous, digitally driven machine. Sometimes the minor inconveniences, longer wait times, and less than 5-star customer service are part of its charm. It’s that authenticity that fosters loyalty. It’s usually a sign that the food is really good.
Silicon Valley solved the problem of cashless payments a long time ago, but that doesn’t mean that it’s the “right way” for every business to operate.
Free group chat > expensive AI workflows
I recently chatted with someone who runs a dessert shop in downtown Chicago that hires mostly hourly employees that work part-time. They diligently track productivity metrics like sales, cook times, and delivery times, and openly praise high achievers based on their performance data. This seemed like a place born for Open Work.
However, what is also true is that nearly every day, someone posts in the storewide group chat that they either need someone to pick up their shift because they can’t come into work, or that they’ll be late to their shift but that they’re on their way. Regardless of how well planned or how far in advance the schedule is set, last second changes always happen.
They use a popular frontline workforce engagement app for HR and scheduling, and it has a feature for trading shifts, but people don’t use it. They just send messages in the GroupMe like this:
An hour before opening: “Can’t make it today, can someone take my shift?”
A few minutes later: “I gotchu”
Everyone looks out for each other like friends do.
No paperwork. No workflows. No headaches. In some ways, it’s inefficient, but it’s also socially empowering.
The informality is actually a cultural asset.
Company executives try to foster this collaborative work environment in ways that are often more expensive and technically complex, but ultimately less effective than a simple group chat. With the late hours making a little over minimum wage, I’m sure that group chat and the people in it are a big driver for the above average retention at this specific location, not the fancy tech stack or values statements that get pushed down from the corporate headquarters.
What would happen if this company adopted Open Work? Could it do more harm than good?
On the surface, adding reporting on the backend of the tool employees use to clock in and out doesn’t sound like a big deal amidst the rest of the operational complexity within food and retail.
But that one decision to adopt Open Work isn’t just another workforce benefit. Just like if the street taco shop stopped accepting only cash, doing so will have a ripple effect into every other part of the business. It would attract, reward with promotions and pay raises, as well as push out a different type of employee, embed a different type of culture, and in a company where the people are as, if not more essential, than the product itself, this one choice could change the trajectory of the entire organization.
Some companies already have a culture where strict punctuality and accountability are at the core, but after seeing how one of the highest grossing locations within this chain actually operates on the inside, I’m not sure that’s the right answer for every team.
The purpose of Open Work is not to turn every work environment into a military academy, nor is it only to serve organizations and employees that embrace that kind of culture. The goal is to make it possible for any employee in any work environment to capture how well they function within that specific system, regardless of what exactly it tracks and rewards.
What if the aforementioned dessert shop chose to track, incentivize, and reward people who picked up other people’s shifts? What if it wasn’t about punishing absences and tardies, but rather about encouraging everyone to be a team player? How could Open Work add value to places outside of corporate America where embracing more informal business customs is essential to success?
We don’t all want to work for (or buy from) the “PE buyout” or “Silicon Valley automated” version of the company we currently love for its warmth, as well as its inefficiency. Open Work is committed to bringing out the best version of every employee and every company, not dictating exactly what that needs to look like.