Learning conversational banking the hard way is expensive; this is the short version.
The future of banking isn’t an app; it’s a conversation. I’m exploring the rise of conversational AI in banking and how it’s changing the way we interact with our finances. From chatbots that can execute trades to voice assistants that can pay our bills, this is the new frontier of fintech.
The Counterintuitive Truth
In conversational banking, the best practitioners often do less, not more.
The lesson: most founders overthink this and underspend on execution. It sounds simple. It's incredibly hard to execute.
What I've Learned From 136 Companies
A few patterns in conversational banking come up again and again.
The founders who handle conversational banking well understand that the best solutions are often the simplest ones.
Why Most Approaches Fail
Many common approaches to conversational banking 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 Numbers Don't Lie
Investing early in conversational banking 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 banking, fintech AI, AI risk management, AI trading that I've been thinking about a lot lately.
Wrapping Up
I've shared a lot here, and I know it can feel overwhelming. But you don't need to get conversational banking right on day one. You just need to get started and keep improving.
Founders who do well at conversational banking tend to share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.
That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.
As always, I'm rooting for you.
Frequently Asked Questions
Q:How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.
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.