Why I'm Building Stax After 8 Years at Amazon

I spent most of March and a little of April this year in Southeast Asia. Cambodia, Vietnam, Singapore. Five weeks, one carry-on, a laptop.

The people I met on the road fell into two rough groups. The first were travelers on trips they had saved up for. Two weeks, three weeks, sometimes a month. Honeymoons, milestone birthdays, the big one they had promised themselves for years. The second were digital nomads, mostly in their twenties and thirties, working remotely from Da Nang or Ho Chi Minh or Bali. They had traded a cramped apartment in an expensive city for a comfortable life in a cheap one, and they were using the surplus to travel even more.

Different people, same underlying move. They had figured out how to save the money, make the commitment, and get on the plane.

The people who hadn't were not in Southeast Asia. They were at home. Smart, motivated, financially capable people with a trip they have been meaning to take. For five years. Six years. Since before their first kid. Since college.

The trip is real in their heads. The savings are not.

The Window Closes From Both Directions

Younger travelers have their own version of the window. The big trips, the adventurous ones, the Patagonia hikes and the six-week backpacking routes, are best done before marriage, before a mortgage, before kids who need to be driven to practice. There is a stretch of years in your twenties when certain trips are still possible, and GenZ knows it. They feel the window closing from one direction.

Stax was originally designed for GenZ, who are digitally native and socially fluent but shut out of the travel they want. Over the past year of conversations, though, a second group showed up just as clearly: mature travelers with a trip they have been describing for years, sometimes decades. My own parents talked about their dream trips for a long time. Then came health issues, and those trips never happened. They are not alone. The window on any given Someday Trip is narrower than anyone thinks.

This is not a motivation problem. These people have jobs or retirement income. They have savings somewhere. Their family would gladly help if there were a way. What they don't have is a single place to turn any of that into an actual trip. The people I met on the road got there by sheer force of will, cobbling together five apps and pushing through the friction. Most people won't do that. They shouldn't have to.

The Five-App Trap

Think about what happens when someone tries to save for a trip.

They open a new savings account, or a bucket inside one. They download a budgeting app to figure out how much they can set aside each month. They Google flight prices. They Google hotel prices. They Google whether they need a visa. They ask three friends what the trip cost them, and the number they get back is a range with a thousand-dollar spread. Their mom offers to chip in for their birthday, and there is nowhere to actually send the money. A cousin says they would contribute if the person ever actually books. The cousin forgets. So does the person.

Six months later there is some money in the account. Not enough. The trip slides another year.

This is the Someday Trip. The one you talk about and never take. Everyone has one.

The travel industry explanation is that people are bad savers, or that they don't plan ahead. I don't buy that. They are not undisciplined. The tools are just not built for what they are trying to do.

A stack of apps won't grow your Stacks.

You can combine a savings account, a budgeting app, a flight search engine, Venmo, and a Google Doc, and you still will not have what you need. Each tool solves a slice. None of them solves the trip. There is a 401k for retirement. There is nothing for the trip.

Why Build This Now

I spent forty years in tech, the last eight at AWS, leading Enterprise Business Development and then Technology Solutions worldwide. That job taught me something that applies far beyond enterprise software: when a category has no infrastructure, every individual user pays the tax. You feel it as friction. You feel it as cost. You feel it as the thing you keep meaning to do.

Travel has been running that tax on regular people for as long as regular people have been traveling. Every year, millions of trips that were supposed to happen quietly do not. Not because people changed their minds, but because the friction compounded and the Someday date kept moving.

I wanted to build something that takes the tax off. That is Stax.

What Stax Actually Is

Stax is a Social Travel Savings app. One container for the whole arc of a trip.

You declare the trip. The app estimates what it will cost based on the destination, the dates, and how you like to travel. You save toward it, either by linking a bank account or tracking contributions manually. You invite the people who have told you they want to help, and they can contribute directly to your trip, not to a vague Venmo request. When you are ready to book, you book through the app and earn cashback on flights, hotels, and activities. The cashback goes into your next Stack.

The Stack is the container. The trip, the money, the contributions, the bookings, all in one place.

Everything else is detail.

The Difference Is Infrastructure

I spent five weeks in Southeast Asia working on this app because I wanted the problem to stay real while I built the solution. Every café I sat in was full of people who had finally made the trip they used to only talk about, and full of people still describing a trip they might never take.

The difference is infrastructure.

Stax is the infrastructure.

Join the waitlist at stax.cash. The first members get a Founding Member rate locked for the life of their membership.

From Someday to Stacked.