Why I'm Building MileIntel (And Why I Can't Stop)

My wife is a surgical resident. I run a startup. Between her 80-hour weeks and my tendency to be on my laptop at 11 PM, the amount of time we actually get to spend together, like really together, phones away, present, is embarrassingly small.

So when we do get a few days, I want them to be extraordinary. Not "let's drive to the beach" extraordinary. I mean "let's fly to Barcelona and eat at a rooftop restaurant overlooking the Gothic Quarter and not think about a single Slack notification for four days" extraordinary.

The thing is, we don't have the budget for that. Not the way most people think about it. I'm a founder (I run another startup alongside building MileIntel), and surgical residents are not, despite popular belief, swimming in money. What we do have is a system. And that system is the reason I started building this.

The Barcelona Trip

Let me tell you about Barcelona, because it's the trip that made me realize other people needed this too.

I'd been planning it for almost a year. Not obsessively, more like a slow game of chess. I knew my wife had a rare block of days off coming up in the fall. I knew I had enough Delta SkyMiles and a pair of Global Upgrade Certificates. So I started watching.

I booked us round-trip Boston to Barcelona in Delta Comfort+ for about 60,000 points each. Comfortable, not crazy. But here's the thing about Global Upgrade Certificates: they can take you from Comfort+ all the way to Delta One. I applied them to the outbound, and a few weeks before departure, both seats cleared into lie-flat Delta One.

For the return flight, I booked strategically. I chose a flight and a fare class where I knew upgrade probability was high, not guaranteed, but the odds were good based on the route, the time of year, and how full the flight was running. We were confirmed into Premium Select, which is already a great seat. But I'd been watching the cabin loads, and sure enough, the morning of the flight, both of us cleared into Delta One for the way home too.

Full round trip. Boston to Barcelona. Delta One both ways. For 60,000 points each and basically nothing out of pocket.

But my favorite part wasn't our seats. A group of our friends met us in Barcelona, and on the way back, I found a last-minute points deal to get them upgraded to Premium Select. They had no idea that was even possible. The look on their faces when they boarded and saw the wider seats and the menu — that's the part I keep coming back to.

The Game Nobody Teaches You

Here's what frustrates me: this isn't magic. It's not some elite skill reserved for finance bros or travel bloggers. It's a learnable game with knowable rules. But nobody teaches you.

I started playing in college. Back then, I was signing up for credit cards because they were giving away 50,000 points for spending $3,000 in three months, money I was spending anyway on textbooks and food. Most of my friends thought I was nuts. "Why do you have four credit cards?" Because each one earns the most in a different category, and together they earn me free flights every year. That's why.

During COVID, when almost nobody was flying, I was. My wife (girlfriend at the time) was in med school in a different state, and I was flying to see her every month. Empty planes, middle of a pandemic, just me and the flight attendants and an overwhelming need to not do long distance over FaceTime anymore. Those flights built my status. I maintained Diamond on Delta when most people's status was expiring, and I kept earning points through credit card spend on everything else. When travel came back and everyone was starting from scratch, I had status, I had points, and I had years of experience. That's not luck — it's just showing up consistently, even when the reason you're showing up is because you miss someone.

The India trip right after our wedding is another one I think about. We were flying economy, no complaints. But at the Virgin Atlantic lounge in Washington Dulles, I used my Global Upgrade Certificates to get us into Upper Class for the return leg. Virgin Atlantic Upper Class. Right after our wedding. That's a memory that's worth more than anything I could buy.

Even on the outbound, we were in economy, and when we connected through Amsterdam, I checked the app and saw two business class seats to Mumbai had opened up for 35,000 points each. I transferred the points right there in the KLM lounge and we were in business class an hour later.

The best travel experiences shouldn't be reserved for people with unlimited budgets or unlimited time to research. They should be available to anyone willing to play the game.

Why This Matters to Me Personally

I'm not going to pretend this is just a business opportunity. It's personal.

My wife works harder than anyone I know. She saves lives and then comes home exhausted and we eat takeout on the couch and it's 9:30 PM and that's our Tuesday. When we get to travel together, really travel, not just go somewhere, it's the thing that recharges both of us. We disconnect. We talk. We remember why we chose this life.

The miles game is how I make that happen without destroying our finances. Planning a year ahead, knowing which cards to use, watching for upgrade availability, understanding which routes have the best odds. It's become this secondary hobby that directly translates into the experiences that matter most to us.

And here's the thing: every year, we've managed to fly to India and at least one other international destination. Barcelona. Tokyo. London. I've almost always been able to get us upgraded, or at minimum, booked in a way where we're paying close to nothing out of pocket. Not because we're wealthy, but because I learned to play the game early and I plan way ahead.

But doing all of this manually is exhausting. I had spreadsheets tracking balances. I was checking airline websites at midnight. I was monitoring transfer bonuses on Twitter. I was doing math on napkins at dinner trying to figure out if 35,000 points for a KLM upgrade was actually a good deal.

That's when I started building MileIntel.

What MileIntel Actually Is

It's the tool I wish I'd had when I was sitting in the Amsterdam KLM lounge frantically calculating whether that upgrade was worth the points.

MileIntel tracks your loyalty balances across programs, monitors award pricing on the routes you care about, and tells you when something changes. It's the difference between refreshing Delta.com every day and getting a notification that says "BOS-BCN Delta One just opened up at 60K. You have enough miles and a Global Upgrade Certificate. Book now."

But I want to be clear: this isn't just for people like me who've been playing the game for years. The person I'm really building for is the one who doesn't even know they can play. The couple sitting on 80,000 Chase points who don't realize that's a round trip to Tokyo. The family spending $5,000/month on credit cards and earning 1x on everything because nobody told them about category multipliers.

Why I'm Sharing the Build

I'm writing this series, "From the Cockpit," because I think the process of building something should be as transparent as the product.

I don't have a team of 50. I don't have a marketing department. I'm one person building between two startups because I got obsessed with a problem and couldn't stop writing code for it. If it works out, I want people to see how. If it doesn't, the lessons should be useful to someone else.

I also want feedback. The miles and points community is terrifyingly knowledgeable. People on r/awardtravel know routing rules that airline employees don't know. If I build something wrong, I'd rather hear about it from someone who flies 200,000 miles a year than discover it six months later.

So every few weeks, I'll share what I shipped, what I learned, what broke, and what I'm thinking about next. Real numbers, real mistakes, no marketing speak.

What's Next

The core is live: dashboard, balance tracking, a concierge that can answer questions about your miles. What I'm working on now:

None of this is complicated. It's just tedious, detail-oriented work that nobody has put together in one place. That's the gap I'm trying to fill.

The Real Reason

The real reason I keep building this, the one that has nothing to do with product-market fit, is that moment in the KLM lounge in Amsterdam, refreshing the app, seeing those two business class seats appear, and knowing exactly what to do.

Or the moment in Barcelona when our friends boarded and found out they'd been upgraded and didn't even know that was a thing you could do with points.

Or every trip to India where my wife falls asleep in a lie-flat seat after a 28-hour shift the day before, and I know she's going to wake up in Mumbai actually rested for once.

This game shouldn't require spreadsheets and midnight browser sessions and years of accumulated knowledge. It should be simple: here's what you have, here's what it's worth, here's the best trip you can take right now. Go make a memory.

My wife and I don't have a lot of time together. But the time we have, we make count. The miles game is how. And I think everyone deserves access to it.