Colin Stroud runs Go Somewhere. He got into points and miles because he couldn't afford to travel. He had just gotten married, taken a low-paying job, and worked out that real travel with a wife and a baby was not happening. So he went down the rabbit hole. Now he does it full time for business owners and people sitting on large point balances.
I went deep on this myself four or five years ago. I still learned things in this one.
Here are the parts worth your time.
The $30,000 Christmas nobody paid for
A client came to Colin wanting a luxury hotel in the Caribbean over Christmas and New Year's. That is the week hotels can charge whatever they want, and they do.
He got them two rooms at the Park Hyatt in St. Kitts. Thirty-five thousand points per night, per room. The cash rate for those two rooms across the week was north of $30,000.
These were standard rooms. Not suites. The hotel had just tripled the price because it could.
They paid nothing out of pocket.
It cost a real pile of points. But it is a pile that any high earner running spend through the right card can build in a year.
Status is mostly a waste, and I have the receipts
Colin's take on airline status lines up with mine. If you are going to buy the front cabin no matter what, status does almost nothing for you. There is no way to guarantee an upgrade. And on long-haul international, the airlines do not do complimentary upgrades at all. That is exactly the flight where you want one.
His line: it is nice to get upgraded from Atlanta to Indianapolis, but that is not a big deal at the end of the day. That is where the upgrades actually happen.
The exception is the person running $200,000 a month through cards. At that level, buy status with one or two airlines and still earn flexible points on everything else.
Hotels are a different animal, and the programs are not the same.
Marriott Ambassador cannot be bought. Colin's point is that you could put $100 million a year on a Marriott card and they still will not give it to you. You have to stay the nights. He likes that, because it means nobody can fake it. Hilton is the opposite. You could open a credit card and land near the top of their ladder. If everyone has it, nobody has it. Hyatt sits in the middle, and he thinks it is the most valuable status that a normal person can actually reach.
This is the part where I will be honest about my own experience. We had Ambassador. It takes $23,000 of spend a year. Last year we missed it by about $500 and they would not honor it. Marriott is strict.
So now I book the cheapest room in the hotel and negotiate my way up at the front desk. I am fine living with that outcome in a hotel. On a twelve-hour flight I am not.
You are probably earning the wrong kind of points
This is the one that costs people the most and gets the least attention.
Delta SkyMiles and Marriott points are locked. They are only good in one place. Flexible bank currencies from Chase, Amex, and Capital One are not. A hundred thousand Chase points can become a hundred thousand United miles, or Southwest, or Hyatt, or Marriott. You decide later, based on what is actually available.
Colin walked through a client in construction spending about $70,000 a month with two suppliers. None of it in a bonus category. No four-times-points on drywall. They want Europe three or four times a year.
He put them in Capital One. Unlimited two points on every purchase no matter how small, and transfer partners that get them out of Orlando or Tampa on Virgin Atlantic to London or Air France direct to Paris.
The right card is downstream of two things: where your money actually goes, and where you actually want to fly. Most people pick on branding and then wonder why the points do not go anywhere.
The back end is where this stops being a rounding error. I am flying to Italy out of San Diego for 70,000 points on a ticket that prices at $6,000. Measured against two percent cash back, that is somewhere around nine cents per dollar spent.
Do not burn points on a room you could just pay for
Marriott only redeems well at the top of the range. A room running a few hundred dollars, even $600 or $700 a night, is rarely a good use of points. Pay cash for those.
We bank ours and spend them in five-night blocks, because Marriott gives you the fifth night free on points. Stack that with a high-end property and you are getting three, four, sometimes five cents per point.
Colin generally steers people away from Marriott's program. But he agrees that if you only ever spend those points at the St. Regis and Ritz-Carlton end, the value holds up. He knows someone who does a week at the St. Regis Deer Valley every year and gets a consistent one and a half cents a point out of it.
You are searching in the wrong order
If you constantly look for award availability and find nothing, Colin thinks you are asking the question backwards.
Most people ask how to get to the British Virgin Islands on January 16th, landing by four. Fine. You will find nothing.
Flip it. You want somewhere very nice in the Caribbean, sometime in January. Now ask what the best deal in the entire region is.
That is how Colin ended up in St. Kitts in the first place. He was scanning Hyatt properties across the Caribbean, found the best deal by a mile, paid 30,000 points a night, and got upgraded. The cash rate on the room he slept in was $1,700 a night. Call it $300 of points for a $1,700 room.
Two tools make this a lot easier. Seats.aero aggregates award space across the airline programs so you are not opening six websites at midnight. In the last year they added an AI assistant on top of their data for about $10 a month. You can type in that you have 400,000 Amex points, you live in Dallas, and you want your family in business class to Italy, and it will find it and then explain why it is telling you to book a Turkish Airlines flight through Air Canada.
If you are starting from nothing, dailydrop.com has a free course. Colin says twenty minutes with it puts you ahead of almost everyone.
Buy the second flight
If you do not live in a major hub, you will keep losing award value before you even start.
Book the main leg on points. Pay cash for the hop to the hub.
We flew ANA business class from Chicago to Tokyo last year and paid out of pocket for a separate Miami to Chicago ticket to get there. That saved somewhere in the range of $12,000 to $13,000. You do have to leave security, collect your bags, and check them again with a different airline. It is annoying. Do it anyway.
Colin had a client in Kansas City do the same thing for a $200 ticket to Chicago and fly direct to Germany from there.
Get comfortable with the itinerary not being perfect. That is the whole trade.
Give the full episode a listen. Colin is one of the few people in this space who will tell you that you are overcomplicating it and that the answer is on Google, instead of selling you something.
— Sam Silverman
Silverman Capital
