This is not a strategy post.

Well — it kind of is. But it's a life strategy post.

This is Part 2 of how we use our business to pay for travel. Specifically, how we paid for spring break this year using points. If you read Part 1 last summer, you know we are pretty nerdy about this. This year, we leveled up.

And because I get asked about this constantly — how we travel four times a year as a family of four without going into debt or sacrificing the business — I'm laying out the whole system here.

Why We Prioritize Travel (And Why It's Part of the Business Plan)

When I left corporate, the goal wasn't a bigger title, a bigger office, or a bigger team. It was freedom. And for our family, travel is one of the clearest expressions of what that freedom actually looks like.

Our girls have been to 11 countries. That has shaped who we are down to the core.

So we have a family rule: we travel once a quarter. Not always international. Not always big. But once a quarter, we go somewhere. A road trip counts. One night away counts. The rhythm is what matters.

Here's the reality though: since 2022, travel for a family of four has more than doubled. Flights, hotels, food, experiences — it adds up fast. So instead of saying "we can't," we built a system. And that system is what I'm sharing today.

The Two Cards Doing the Heavy Lifting

Marriott Bonvoy Brilliant

We've been Marriott members since my corporate consulting days — back when I was living in hotels for work. That history built up status over time, which means room upgrades, late checkout, and occasionally free breakfast. That matters a lot when you're traveling with twin girls.

This card paid for 100% of our Hawaii hotel last year. For this spring break trip, it covered about a quarter of our total hotel stays. Still a significant chunk of a trip that would otherwise have cost us thousands out of pocket.

What we use it for: Personal spending. Hotels. Anything non-business.

Chase Sapphire Reserve (We Upgraded This Summer)

All of our business expenses go on Chase Sapphire Reserve. Team payments, software subscriptions, contractors, ads — everything business-related runs through this card. This keeps the tracking clean and the points accumulating fast, because business spending adds up quickly.

What we use it for: All business expenses. Flexible point transfers.

The Transfer Move Most People Don't Know About

Because our Hawaii trip used a significant number of Marriott points, we needed to top up the balance for this trip. Here's what most people don't realize: you can transfer Chase Ultimate Rewards points directly to Marriott Bonvoy. We did exactly that.

Then we used the Chase Travel Portal to book the rest of our accommodations — and saved 30% on Vegas shows while we were at it. (Yes, we took the girls to Vegas for 48 hours. Direct flight, fun shows, easy trip home. No judgment. 😂)

What We Actually Paid For With Points

Here's the breakdown for our spring break trip covering Arizona, Utah, and Nevada:

• Hotels: 100% covered by Marriott Bonvoy points (combination of earned points and transferred Chase points)
• Flights: Covered by airline points from a previous trip
• Vegas shows and experiences: 30% savings through the Chase Travel Portal

The actual out-of-pocket cost for accommodations on this trip? Zero.

How We Planned It Using ChatGPT

This is the part I love talking about, because it made the whole process so much faster.

I opened ChatGPT and typed: "Here's where we're going: Arizona, Utah, Nevada. Here's how many points we have in Marriott and Chase. Where should we use which points to get the best value?"

It helped us map which properties were better for Marriott redemption, when it made sense to transfer points versus book directly, and when to use the Chase Travel Portal instead. Then I asked it to identify which experiences in those cities offered the best point redemption or partner discounts through Chase.

It's like having a travel hacking assistant available at midnight when you're deep in planning mode. You don't need to be an expert in points optimization. You just need to ask better questions.

ChatGPT Prompts You Can Use Right Now

If you want to try this yourself, here are the exact types of prompts that work well:

• "Compare Marriott Bonvoy Brilliant vs Chase Sapphire Reserve for a family that travels four times per year."
• "What's the best way to maximize Chase Ultimate Rewards for hotels in [city]?"
• "Is it better to transfer Chase points to Marriott or book through Chase Travel for [destination]?"
• "What are the most overlooked credit card perks that families forget to use?"

Start there. Let it do the comparison work. Then make the decision based on what it surfaces.

The Spreadsheet That Changed Everything

My best friend Megan taught me this one, and it is genuinely one of the most useful things we've ever done for our travel system.

We keep a simple Excel spreadsheet — nothing fancy — that lists every card we hold with the following columns:

• Card name
• Annual fee
• Benefits and credits
• Expiration dates on credits or offers

Why does this matter? Because you have benefits you are forgetting about.

Here's a real example. We have a $250 StubHub credit on one of our cards. Do we use StubHub often? No. But now that it's on the spreadsheet? We will. We also have an Uber credit. We don't use Uber every day — but knowing the credit exists meant I could surprise the girls with Cane's Chicken on Valentine's Day via Uber Eats and pay zero out of pocket.

Those little quirks are what make the annual fees worth it. But only if you actually know they exist. Intentionality is everything.

The Bigger Picture: Business Spending Becomes Life Experiences

Here's the part I really want you to sit with, because this is the core of why I share posts like this.

Every invoice I send. Every team member I pay. Every software subscription I run through the business. That spending becomes points. And those points become experiences.

We don't overspend to earn points. We don't carry balances. We pay off both cards every single month. But we are strategic about where the spending lands, and that strategy compounds over time into something that genuinely changes what our life looks like.

This is what "life-first business" actually means in practice. Not the aesthetic of it. Not the aspirational version. The real, spreadsheet-and-ChatGPT version of designing your business to fund the life you actually want to live.

And yes — inflation is real. Travel is expensive. It would be easier to not go. But instead of shrinking, we optimized.

The Practical System: How to Start Doing This

You don't need to have our exact card setup or our exact travel rhythm. But here's the framework that works for us, which you can adapt to fit your life:

1. Separate business and personal spending completely. This is non-negotiable if you want to build points efficiently and keep your accounting clean. One card for business. One card for personal. Full stop.

2. Pick one to two cards that align with how you actually travel. If you're loyal to Marriott, the Bonvoy Brilliant makes sense. If you want flexibility and your spending is high enough to justify the fee, Chase Sapphire Reserve is hard to beat for the transfer partners alone. Don't collect a dozen cards. Pick the ones that match your real travel patterns.

3. Build your benefits spreadsheet. Do this once. Keep it updated. Set a calendar reminder every January to review it. This single habit will recover more value from your existing cards than any new card you could sign up for.

4. Use ChatGPT to plan your redemptions. Before your next trip, open a conversation and tell it exactly what you have and where you're going. Let it do the comparison work. The quality of your redemption strategy will go up significantly.

5. Set a travel rhythm and protect it. Quarterly is ours. Yours might be twice a year. It might be one big trip and a few overnights. What matters is that it's on the calendar and it's non-negotiable. When travel is a planned part of your year, you plan for it financially. When it's spontaneous, it becomes a stress.

The Real ROI

We don't do this perfectly. There are credits we miss. Transfers we forget to optimize. Points that expire before we use them.

But we do it intentionally. And intentionally is enough.

Our girls won't remember the spreadsheet. They won't remember the ChatGPT prompt or the transfer from Chase to Marriott. But they will remember the desert hikes. The Vegas show. The hotel pools. The time together in places they've never been.

That's the real return on investment.

And that's why every business decision I make comes back to this question: does this support the life I'm building? Not someday. Now.

Go read Part 1 if you missed how we use our business to fund travel. And if you want to see more behind-the-scenes life and business posts like this one, let me know. Because sometimes strategy is a 47-tab spreadsheet. And sometimes it's Cane's Chicken on Valentine's Day paid for by points. Both count.

Frequently Asked Questions About Using Credit Card Points for Family Travel

What are the best credit cards for families who want to travel using points?

The best combination for most families who travel consistently is pairing a flexible points card like the Chase Sapphire Reserve with a hotel loyalty card like the Marriott Bonvoy Brilliant. The Chase card earns flexible Ultimate Rewards points that can be transferred to airline and hotel partners or used through the Chase Travel Portal, while the Marriott card builds loyalty status that unlocks room upgrades, late checkout, and free night certificates. The key is to match your card choices to how you actually travel — if you're loyal to a specific hotel brand or airline, lean into that ecosystem rather than spreading points across multiple programs.

Can you transfer Chase points to Marriott Bonvoy?

Yes — Chase Ultimate Rewards points can be transferred to Marriott Bonvoy at a ratio of 1:1. This transfer is one-way and generally non-reversible, so it's worth comparing the value of using points through the Chase Travel Portal versus transferring them before you commit. For high-value hotel redemptions, transferring to Marriott can offer excellent value, especially at properties where Bonvoy points are worth significantly more than the portal rate. Use ChatGPT or a points comparison tool to run the numbers before your next trip.

How do you use ChatGPT for travel planning and points optimization?

ChatGPT works well as a travel planning assistant when you give it specific information about your points balances, destination, and travel dates. Ask it to compare redemption options across your cards, identify which properties offer the best value for your points in a specific city, or surface partner discounts through your card's travel portal. It won't have access to real-time availability, but it's excellent for strategy — helping you think through whether to transfer points, use a portal, or save your points for a higher-value redemption. Treat it like a knowledgeable friend who can run comparisons quickly, not like a booking engine.

How do I keep track of all my credit card benefits so I don't miss credits?

The most effective system is a simple spreadsheet — one row per card, with columns for the annual fee, all benefits and credits, and expiration dates on any time-sensitive offers. Review it at the start of every year and set calendar reminders for credits that reset annually. Most people are sitting on hundreds of dollars in unused card benefits simply because they signed up, set up auto-pay, and never looked at the full benefits package again. One hour spent building this spreadsheet will save you money every year going forward.

How do you travel quarterly as a family without it becoming financially stressful?

The short answer is that you plan for it instead of treating it as spontaneous. When travel is on the calendar as a non-negotiable four times a year, you build the budget and the points strategy around it rather than scrambling when the trip comes up. Using business spending to earn points means the money you're already spending on operations is doing double duty. Paying off cards monthly means you're never paying interest. And choosing a mix of big trips and simpler overnights means the rhythm is sustainable even when time or budget is tighter in a given quarter. The goal is a system, not perfection.