As we move closer to a cashless society, the role of AI in our financial lives will only grow. I’m exploring the implications of this shift, from the death of privacy to the rise of new forms of digital currency. This is a glimpse into the future of money.
Why Most Approaches Fail
Many common approaches to cashless payments are flawed at the root.
The root cause is usually one of three things:
Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.
Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.
Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.
The Framework That Actually Works
Here is a simple framework for evaluating cashless payments. It's not complicated, but it requires discipline.
Step 1: the best solutions are often the simplest ones
This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: customer feedback is the only metric that matters
Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.
Step 3: Iterate relentlessly
Nothing works perfectly the first time. The companies that get cashless payments right treat it as an ongoing process, not a one-time project.
The Counterintuitive Truth
In cashless payments, the best practitioners often do less, not more.
The lesson: customer feedback is the only metric that matters. It sounds simple. It's incredibly hard to execute.
The Numbers Don't Lie
Investing early in cashless payments can be the difference between raising your next round and running out of runway.
One of my portfolio companies went from struggling to profitable in under a year after they finally got serious about this. The founder told me later that they wished they'd started sooner.
This connects to broader themes around AI trading, robo-advisors, AI banking, algorithmic trading that I've been thinking about a lot lately.
The Bottom Line
None of this is rocket science. But it does require intentionality, consistency, and a willingness to learn from mistakes.
If you take one thing from this article, let it be this: start now, start small, and iterate. The founders who win at cashless payments aren't the ones with the best strategy on paper. They're the ones who execute, learn, and adapt faster than everyone else.
Companies that take cashless payments seriously tend to pull ahead of the ones that don't.
If you're working on something interesting in this space, I'd love to hear about it. Drop me a line.
Frequently Asked Questions
Q:What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
Q:What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 234 startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
Q:How can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.
Q:Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.