Two weddings. A honeymoon to remember. Points waiting to be earned and miles ready to fly. Let's plan the strategy that turns every dollar you were already going to spend into a gift worth toasting — champagne flutes raised, boarding passes in hand.
Rough and approximate is perfect. Nothing precise.
Please don't include any of the following — they're not needed to build a points strategy:
This is points-strategy planning, not a financial application. Anything sensitive stays with you — you manually copy the summary at the end and send only what you're comfortable sharing.
What's the #1 thing you most want me to figure out for you?
So I focus on getting that right above all else. Pick one — or write your own below.
Pick the intensity that feels right today.
No wrong answer. The more you share, the more tailored the strategy — but don't get stuck on anything. You can always come back and add more later.
Just enough to calibrate the strategy. Nothing precise required.
Add an entry for each child getting married. The date drives the whole timing strategy — and we'll capture honeymoon plans here too, since they often need different cards than the wedding itself.
Click any card you have to add it. Click the same card twice if both you and your spouse have one. Card names only — never card numbers.
This matters for Chase's 5/24 rule and re-earning welcome bonuses. Add any closed cards for either spouse. Skip if none.
Combined household balances are fine for now. Rough figures work — leave blank for any program you don't use.
These often expire — we want to use them before losing them. Skip any you don't have.
Outside of wedding contributions — your baseline spending drives which cards make sense long-term, well beyond the weddings.
Last set of questions — these determine how aggressive we get with the strategy and where we focus the payoff.
Review your answers below. When you're ready, tap Copy Summary and paste it into a reply — I'll take it from there and come back with a custom points strategy.
How should I reach you with the strategy?
So I know the best way to follow up — and you're not chasing my reply.
Sends directly to Simon — arrives in his inbox in seconds