The Definitive Travel Rewards Episode w/ Chris Hutchins #899

When it makes sense to buy points, sites that make redeeming your points a breeze, how he thinks about points deflation… these are just a few of the topics we cover with our friend Chris Hutchins. If you’re wondering, like we were, whether or not travel hacking is still worth the hassle then this is the episode for you. And Chris covers a range of topics on his podcast, All The Hacks, like ways to gain confidence, practical steps to strengthen relationships, and anti-aging with his diverse guests. Chris was a co-founder of Milk which was acquired by Google, then he was the founder and CEO of Grove which was subsequently acquired by Wealthfront- he’s quite the renaissance man, he loves technology and optimizing virtually everything, and we get into a variety of topics today!

 

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Episode Transcript

Speaker 1 (00:00):
Welcome to How to Money. I'm Joel and I am Matt,
and today we're talking about the Definitive Travel Rewards episode
with Chris Hutchins.

Speaker 2 (00:27):
Yeah, Joel, this is going to be an episode that'll
be fully dedicated to what the kids call travel hacking.
And that's actually just one of the topics that Chris
Hutchins discusses on his podcast All the Hacks, which I
will say, it's a great name for a podcast, by
the way, among us personally, I'm a little jealous. And
it's also really accurate as well, because Chris he covers
a range of topics on his show, not just travel,

(00:48):
but like how to be more confident, ways to strengthen relationships.
I saw recent or not too long ago, he had
a conversation with Brian Johnson about living longer. Joe, we
actually we had a discussion about Brian Jonson. Yeah, on
the podcast there's a lot of money doing that a
while ago. But prior to the podcast, Chris was a
co founder of Milk, which was acquired by Google. Two
percenters killing Chris, He's the whole type of guy. But

(01:11):
then he was the founder and CEO of Grove, which
was subsequently acquired by Wealth Front. He is quite the
renaissance man, and we're excited to have him joining us
today to talk about travel rewards. And this is a
special episode because Chris is here in person with us,
hanging on in our little little clubhouse. So Chris, thank
you for joining us today on the podcast.

Speaker 1 (01:30):
Due thanks for having me. I like it. You call
him a renaissance man. He's like Leonardo da Vinci and
DiCaprio all rolled into one. I'd say, is that true?
Chris the old? Maybe the old? I'd like to let
himself all right. First question we ask everyone who comes
on the show is what do you like to Sporgehn
Matt and I sporge on craft beer? Obviously everyone knows that.

(01:51):
What's that for you? Even while you're still doing smart
stuff with your money?

Speaker 3 (01:53):
Yeah, so I thought about this and I was like, well,
you guys, you guys got to graduate outside of just beer.

Speaker 1 (01:57):
So I want to hear some more things. But we've
got other things.

Speaker 2 (02:00):
Yeah, but this isn't about us, know about I see
what you're trying to do.

Speaker 1 (02:03):
No, no, no, I have an answer.

Speaker 2 (02:04):
You're like slide into the podcast host. See, no, no, you
are the guests today, Sir.

Speaker 3 (02:09):
I think recently I've started not batting an eye at
spending money on information.

Speaker 1 (02:16):
So okay, So it's likely Pedia Britannica. Okay.

Speaker 3 (02:21):
But like, if I think something will, like whether it's
a book, whether it's a subscription to someone's premium content
site at substack, if there's something that I think I
could learn from. I used to think, Gosh, is this
really worth it? Couldn't I go find this information online free?
Maybe it comes back to spending money to save time,
but it's just like, I'll just pay the twenty dollars,

(02:42):
I'll pay the fifty dollars whatever the cost is if
I think it will make me smarter, satiate my curiosity
or something. I try not to think about it.

Speaker 1 (02:50):
Isn't that amazing how we went from everything needs to
be free and that supported and now think about what's
happened with sub second, all that we pay Matt for
a couple of different subs writers because it's such good content,
such good information, And you think eighty bucks a year
for this one person's writing. That's crazy, that's crazy talk.
But we're doing right and left these days, I know.

Speaker 3 (03:11):
And then, but and then apps sometimes I find. I
tell my mom, I'm like, oh, you should down this
Habit's really good, and she's like, yeah, but it's ninety
nine cents. And I'm like, come on, somebody took time
to and maybe now as an AI took time to
build it, but somebody took time to submit it to
the app store. True, And so I think a lot
of those things. Maybe it's because I'm on the other
side now, I'm like, I'm a creator, Like I create things.
I'm less, you know, objecting to spending money towards things

(03:36):
other people build. So I'll extend that to software.

Speaker 2 (03:39):
Fair enough well, and not to justify the expense. But
I like what you said too, as far as it
is a way that, yes, you could spend the time
and comb through different websites. Ask your AI app that
the system that you were just showing us before the
before we record, ask it to find the answers for you.
Or you can get it directly from the source yourself,
if you know it's a I don't know, a reliable source,

(03:59):
and if it provides a lot of value for you.
But you know, so I kind of mentioned I touched
on a couple of the companies that you were highly
involved with early on. How often do you think about that? Like,
does that influence how it is that you think about
Let's say, like we're just talking about paying for data.
Are you kind of constantly thinking through just new opportunities,
new ideas. I'm curious how that impacts how you view

(04:21):
the world right now because you've got a podcast all
the hacks, but you're you're more than just like a
podcast host. You're not just trying to find ways to
cut corners.

Speaker 1 (04:29):
Yeah, I'd love to hear you speak to that.

Speaker 3 (04:31):
I think having worked for like a decade in Silicon
Valley building startups, spending a lot of time trying to
find new ways to do things, I think I bring
that to everything. I definitely this goes long before that career.
I was always the person in school where I'd be like, no, like,
there's got to be a better way. Can't I do
it a different way? Can I take the final today

(04:52):
so I don't have to sit in your class all day?
And so when I started a podcast, I wasn't like, Oh,
I just do what everyone else does. I was like, Oh,
why don't I treat this like a business? How do
the analytics work? How does the growth engine work. How
do you know what kind of viral loops can you create?
And I think every time I look at anything, I
come with that like entrepreneurial founder mentality of what could

(05:13):
this become? How could it be done differently? What is
everyone else missing? And I'm just amazed at how many
industries just kind of operate the same way they've been
operating for a long time. And podcasting is one where
we've had a lot of conversations about this, the three
of us, Like some people are just sitting there doing
the same thing they've done for ten years, and then
you're like, ooh, what if we try this thing differently?

(05:34):
You guys were talking about SEO earlier, Like there's all
these opportunities to treat a podcast like a business, but
I think there's opportunities to treat your life like a business,
your relationship like a business. Not in the sense that
you need to make it a business, but what are
ways to make it more efficient? How could you improve it?
Like I'm kind of taking that growth mindset to everything
I do. I'm curious relationally, what does that look like

(05:54):
for you and your wife? When you treat that, do
you treat your marriage like a business. I mean, we
work together. So yeah, yeah, I think one way is
what are better ways to have a healthy relationship. When's
the best time of day for us to have certain conversations?

Speaker 1 (06:09):
Is it to happen in the morning.

Speaker 3 (06:10):
I don't know. Does that work? We have a sauna?
Now do we have our conversations in the sauna where
we're not just dric.

Speaker 1 (06:14):
That should we have them? That should have been your
your craft bere equivalent.

Speaker 3 (06:18):
So things like that, like we're experiment with when we
have the conversation. We'll experiment with whether we one time
we were like, let's write up notes before we have
like a you know, like a family goals check in
or you know, we just open to different things. Yeah,
we've seen people post stuff like here's the way we
do our check ins. I don't believe that the way
we operate our relationship at any given point in time

(06:39):
is the answer. I think the biggest change was I
interviewed this couple that wrote a book called The eighty
eighty Marriage, and their general principle was, so many relationships
are fifty to fifty. Tip for tat you did the
dishes last night, I'll do them this night. You watched
Watch did Kids Bedtime, I'll do it, And their idea was,
if you can just operate on the assumption that everyone's

(07:00):
doing eighty percent, you can stop keeping score and it
gets rid of a lot of the overhead in a relationship.
And so we tried that. I was like, oh my god,
it's so nice. It was like, you just assume the
other person is going to do as much, and obviously
you have to have a partner that's willing to do
a lot, Like yeah, if you have to be the
partner willing to do a lot too, exactly, But if
you're both that and you can stop keeping score, then
it just gets rid of a lot of the I guess,

(07:21):
the overhead of a relationship and operating a family, which
is kind of also like a business schedules kids.

Speaker 1 (07:27):
Yeah, it is. We talked about the startups. You started
one called laid Off Camp at one point, right, I
don't know, I'm curious for people out there for unemployments
pretty low right now, but what if someone does face
a layoff or there's certain things that they need to
do immediately post that happening.

Speaker 3 (07:43):
So mine kind of came by surprise, but it was
in the middle of the Great Financial Crisis in two
thousand and eight, so I was not alone in the
fact that there are lots of people who lost their jobs.

Speaker 1 (07:53):
I think right now, with everything.

Speaker 3 (07:57):
That's happening on the internet, with all these language models,
AI tools, it has never been easier to kind of
experiment on your own. And I really wish that I
had a complete, blank slate of time for the next three,
four or five months to just play around, because the
things you can build are unbelievable. I remember five ten

(08:17):
years ago, I'd get all these calls from people. I
remember one time I talked to someone at my university
and they were like, I've got an app idea, And
I was like, oh gosh, another one of these, Like
random person who doesn't have any experienced building software wants
to build an app. Well, now that person can build
the app and put in the app store like next week.
And so I would say, if I had gotten laid
off right now, assuming I'd had an emergency fund and

(08:39):
a lot of the things that I know you guys
care about as well, now would be an awesome time
to be able to experiment with any idea you have
and find product market fit quickly. On really anything, because
it's never been easier to build. But it sucks and
I'm sorry. Yeah, there's no way to skirt around.

Speaker 1 (08:56):
What you're saying is that you wish you had that
additional time. It's funny how much you have the financial prep. Yeah, yeah,
so get ready for it. But I'm curious if you
ever regret.

Speaker 2 (09:05):
So it's interesting that you mentioned like the relationships part
of the question, jol.

Speaker 1 (09:10):
But because like when.

Speaker 2 (09:11):
You hack something, what you're typically focused on is the
end result, right and so, and the idea is that,
like what can we do to get us to the
end result quote unquote faster or more efficiently? Do you
ever regret doing that because of what you're missing out
in the process, like in the interim, Like sometimes the
process how it is that you achieve that end result.

(09:33):
It's formational, like the means mean more than the end.

Speaker 1 (09:35):
Yeah.

Speaker 2 (09:36):
Like so I hate to use this as an example,
but like some of the Semaglue, tides, wigov, all these
different drugs.

Speaker 1 (09:43):
You got canceled the other day for using that.

Speaker 2 (09:45):
So but you don't there's something that you Obviously there
are amazing results that people are experiencing by doing that,
results that they would never have been able to achieve otherwise,
and I think it's fantastic, But there's also something that
you're missing out in the interim, which is, let's just say,
movement or loading your bones, things that also benefit your body.

(10:06):
So in a similar way, do you ever see instances
where you say, man, it's pretty cool that I was
able to achieve that ends faster, but that there was
something that you missed out on in the interim.

Speaker 3 (10:16):
I think I just try to think of it at
a higher level, so not just playing at ten thousand feet,
but thirty thousand feet and zoom out. Because if the
end goal is longevity, for example, if we're talking about health,
it's like, well, you do need strong bones and lots
of muscle mass. And if you just get on GLP
one so you don't take any protein and you don't
work out, you will lose weight, but you will lose

(10:36):
your muscle mass and that's not going to be good.

Speaker 1 (10:38):
For the long game.

Speaker 3 (10:39):
Sure, So the hack isn't to just do that. The
heck is to say, okay, what's the best set of
protocols I could put together? And maybe the hack is, okay,
I need to eat more protein and do more strength
training and do in addition.

Speaker 1 (10:51):
So got it. I think it's funny.

Speaker 3 (10:53):
The word hack is a tough one for me because
so many it turns off a lot of people, right,
But it also I can't find a better way to
succinctly say what I like. But what I like is
look at a thing and find out if there's a
better way to do it, And that better way might
be to take longer doing it right. That better like
the hack, might be that you don't try to make
this shorter, you actually spend the time because the energy

(11:16):
you put into it is the experience. And so my
ethos has always been if there's a thing you want,
there's probably a way to get that thing, whether it's
an outcome, a good, a service for less. And so
after you mentioned laid off camp, after I got laid off,
I was like, I need to find a job, and
the jobs I've had in the past I didn't love.

Speaker 1 (11:35):
So I don't know what to do.

Speaker 3 (11:38):
But I need to save money as aggressively as possible
with whatever I do, because I haven't found a job
I love. But I don't want to just like eat
beans and rice and live in like a little cabin
in the middle of nowhere. So how do you find
ways to take the things you love doing in life?
My wife and I love traveling, but not spend money
on them because we need to take that money and
save so that we don't have to work at jobs

(11:59):
we don't love forever.

Speaker 1 (12:00):
Okay, so you want it all?

Speaker 3 (12:01):
Yeah, I want it all, but like I don't want
to I don't want to sacrifice. And I think that
that's where the kind of hacking mentality comes up. It's like,
is there a way to do it? And sometimes the
answer is no, you just have to work hard.

Speaker 1 (12:11):
Yeah for some folks.

Speaker 2 (12:12):
Well, that's when it comes down to the individual as well,
because there are some folks that don't necessarily have the
capacity to maybe think about problems in the in the
way that you are, in which case hard work. You
know that, like for them, that's going to be the
only solution. So you alluded to travel. This is gonna
be a little teaser as we set up are the
credit card points? How many points do you do you
have like a running total of how many points that

(12:34):
you have a mass over your entire lifetime?

Speaker 1 (12:36):
A massed over my lifetime?

Speaker 2 (12:38):
No?

Speaker 1 (12:38):
Okay have currently? Yes?

Speaker 3 (12:41):
Approximately A massed over lifetime. Maybe, like I could probably ballpark.

Speaker 1 (12:45):
Okay, what do you think the ballpark is? So right now,
I have a little over sixteen million.

Speaker 2 (12:49):
Oh gosh, that is insane.

Speaker 1 (12:52):
So I'm gonna say it's somewhere over twenty. Oh my gosh,
that's a lot of points. We have a lot to
talk to you about credit card points than one of
the most interesting stories I've heard though, that you've used
points for, because typically we talk about buying a plane
ticket or paying for a hotel stay with your points,
and those are very traditional ways. You paid for your
wedding photographer with credit card points.

Speaker 3 (13:13):
Yes, So I met this woman who was technically videographer,
and I was like, I love a wedding video. I'd
never even thought about it. It wasn't really in the budget,
but I actually had no idea how much a wedding
videographer cost. And I saw this video online and I
was like, it was beautiful, But it was for this
guy's wedding who I just I didn't know him personally,
but I knew he had a lot of money, and
I was like, well, it was really good. Let's just
reach out. You know, sometimes things are the same price

(13:36):
depending on who you hire, sometimes are super expensive. And
she came back with a price that was five figures
and I was like, wow, this is not in the budget.
And we were talking and we actually kind of hit
it off. She thought like we just had a good conversation.
You know, you meet people and you're like, I could
be your friend. So this wedding videographer and I were
like having a great conversation. She like me, my wife,

(13:56):
she grew up in Colorado, the wedding was in Colorado.

Speaker 1 (13:58):
It just all seemed to click.

Speaker 3 (13:59):
And then she's at the price and I was like, yeah,
we can't do this and she was like, oh, like
I really thought it'd be a fun wedding to do.
It turns out that as you move up in the
client tele you have when you start doing weddings for
the richest people, you know, doing the most expensive weddings,
they actually sometimes lack a lot of personality. So she
actually was like just dying for a reason to do

(14:20):
someone's wedding that she told me this later, that wasn't
just the cookie cutter wedding she'd been doing and doing,
but not at the expense of doing a pro bono
that was not an option. But in our conversations, I
told her that we were taking our honeymoon to the
Seychelles and she was like, oh my gosh. My husband
and I thought it would be amazing to one day
go to the Seashells, which is a small tropical island

(14:41):
kind of halfway between Southern Africa and India, like middle
of nowhere. And I was like thinking about this, And
then a couple days later, Delta had this promotion where
if you transferred miles from your account to someone else's
account and you had to pay but not too much,
they would double them, and so I had I was like, well,
I was about to transfer all these miles to my
account to book our flight to the Stayshells. So I

(15:04):
reached out to her and I was like, hey, you
mentioned that you would really love to go on a
honeymoon to the stay Shehells. What if I booked you
and your husband business class tickets to the Seayshells as
you know, maybe we could do something here. And she said, yeah,
I think that.

Speaker 1 (15:19):
Could work a little barter. Yeah.

Speaker 3 (15:21):
She came back and she's like, let's do it. She's like,
if you can just pay for the fixed costs, like
the hotel room for the videographer and those kinds of things.

Speaker 1 (15:29):
Then we'll do it.

Speaker 3 (15:30):
And so instead of transferring to miles just from I
think it was AMEX to my account. It was AMEX
to my account and then my account to my wife's account.
And I think the transfer call, like to transfer the
miles was like twelve hundred bucks and the hotels were
probably like five hundred bucks. So we saved I know,
we saved over ten grand.

Speaker 1 (15:45):
Yeah, video, it's amazing.

Speaker 3 (15:47):
And the street cost of those tickets were like ten
grand each. So she got two tickets that cost twenty grand.
Not to say she was going to pay twenty grand
for them, but she got twenty thousand dollars of tickets.

Speaker 1 (15:59):
She got a better deal. You got a better deal.
You're thinking outside the box of the MSRP. Yeah, she
feels wealthy. Yeah. Now that's a great wedding video. Yeah,
that's awesome, dude. Yeah, I mean, I think there's so
many interesting things we can learn talking to Chris, and
specifically we're gonna dive all the way into credit card points.
We're gonna get like knee deep, maybe even chess deep
my credit card points stuff. So We'll get to more
questions about that with Chris right after this. I we're

(16:29):
back for the break talking with Chris Hutchins.

Speaker 2 (16:31):
This is the definitive travel Rewards episode, and Chris, before
we dive into kind of like the specific details and
how we can maximize credit card travel rewards. I think
it's worth asking the question if it is even worth
it to chase points anymore, because like back in the
day before let's say Chase implemented the five twenty four rule,
it felt like it was a little bit more of

(16:51):
the wild wild West several years ago, where it seemed
like that there was also just more opportunity. But do
you feel like that there is still the opportunity today
to maximize the points that you can earn from some
of the different credit card issuers.

Speaker 3 (17:04):
I saw this great post I think it was in
the Wall Street Journal where it's like the value of
credit card rewards has gone down, and then someone combated
that post saying, yes, the actual number of you know,
the ability to get a trip to Europe with your points,
it takes more spend now than it used to. On
the flip side, the cost of that trip has gone
up and the sign up bonuses on cards has gone up,

(17:25):
and the like number of points you earn per dollar
have gone up to the point that I think you're
actually better off now than you were before. Really, so
I think that's true. What has also changed, though, The
little wrench I'll throw into this is that the amount
of cash back alternative that you could return like earn
has also gone up, so your opportunity like, I think
points have gotten more, not more valuable, but the quantity

(17:47):
of them that you can earn gets you more total value.
But the alternative or the opportunity cost is cash back
that's also gotten better. So I think overall we win.
No matter which game you played, the game has gotten better.
Whether you want to play the game or not. I
think really comes down to how you want to travel
and whether you want to travel. Sure, if you don't
want to travel, you should probably get some cash back. Yeah,

(18:08):
that's where you should focus. If you want to travel
just domestically, and or you want to travel internationally, but
you only want to travel an economy and you always
have really fixed dates and you don't you're not that flexible.
Cash back is probably going to take you further. But
if you want to do aspirational travel. You want to
fly in you know, premium cabins, you want to stay
at really high end resorts, and you have a little

(18:29):
flexibility whether that's where you go, when you go, whether
you change planes along the way. I think miles and
points will get you significantly further than cash back.

Speaker 1 (18:38):
So a lot of people who are listening might say, well,
it seems like the best credit cards come with significant
annual fees attached to them, right. I think you told
us before you don't have to share this if you
don't want to. But how much you spend every annually
in annual fees on credit cards? It's up there. So
what would you say to somebody who says, gosh, I
just don't know if I'm going to get the value

(18:59):
for the annual fee it comes with this card, and
whether or not that makes sense for me given the
benefits I might or might not get, I would say, every.

Speaker 3 (19:05):
Time I've done the math, the annual fee is often
unjustified by the points earning rate, Meaning this card earns
two points per dollar on everything, but this one earns
two point five. Am I gonna spend four hundred dollars
and make it worth that extra half a point on
every dollar I spend. And unless you're running a business

(19:25):
putting hundreds of thousands or millions of dollars through your card,
that one's gonna be harder. Where the annual fee is
kind of very easily negatable is looking at all the
perks and credits the card comes with. So if I
had to guess, I probably have like sixteen ish credit
cards easily probably three four thousand dollars of annual fees.

(19:46):
But let's take a card, the Hilton Aspier card.

Speaker 1 (19:49):
Paula has I.

Speaker 3 (19:51):
Five hundred something annual dollars five hundred dollars annual fee ish,
but you get a free night at any Hilton in
the world. And so we've used that to stay in
hotels that otherwise we most recently used. At a hotel
it was three grand a night. Wow, Now what I've
stayed at the three where or in Majorca, Spain? Okay,
it was incredible and so okay, So pay five hundred

(20:12):
dollars get a three thousand dollars.

Speaker 1 (20:14):
A night hotel room. Sounds a good deal.

Speaker 3 (20:15):
Yeah, it's also got a fifty dollars credit. It's kind
of annoying every quarter for airlines so I just go
into the United site, I add fifty dollars to my
travel bank, get that fifty dollars credit back, so I
can capture two hundred there. With many of these cards,
if not all of them, they've kind of become this
little coupon book, which if you're not going to take.

Speaker 1 (20:35):
It's a perfect way to describe it. It's like those
Q funny books you just spend twenty bucks on and
you have to flip through them and find them and
use them. That's how it works.

Speaker 3 (20:41):
So AMEX, a lot of MX cards have an airline credit.
It only works on one airline, and if you and
it doesn't work on flights, it only works on the
incidental fees. If you pick Southwest, it also works on
any flight under one hundred dollars, or maybe it's one
hundred and ten dollars. So go buy a seventy dollars ticket.
Southwest has free cancelation. Cancel it. Use that credit to
book a two hundred dollars ticket. Now you've been able
to kind of cash out your credits.

Speaker 1 (21:04):
You know.

Speaker 3 (21:04):
One of the things I thought about saying I splurge
on at the beginning was I'm wearing like twenty five
or thirty dollars boxers, which to me seems an egregious
amount of moneys amount of boxers. But the Platinum card
has a fifty dollars SAX credit, and like there's just
nothing cheap to buy at sacks except for boxers. So
it's like we could buy these these unreasonably expensive boxers
because I have this fifty dollars credit. So I wouldn't

(21:26):
value that fifty dollars credit at fifty dollars because I
wouldn't pay fifty dollars for two pairs of underwear.

Speaker 1 (21:30):
Would do it otherwise?

Speaker 3 (21:31):
But I probably valued like twenty bucks. Yeah, And so
if you sum up all the cards I have and
how money, how much value I get from those credits?
Very few of my cards have a net annual fee.

Speaker 1 (21:42):
Yeah all right, okay, So is it ballar to spend
four grand if you get five grand back? I don't know.
I just think it's smart. Yeah, yeah, I think you're right.
It makes sense.

Speaker 2 (21:50):
So you mentioned Southwest, What are your thoughts there? Because Southwest,
specifically the Companion Pass, that has been my first foray,
because up until I would say last year or a
couple of years ago, when I first went after the
Companion Pass.

Speaker 1 (22:01):
And got it.

Speaker 2 (22:02):
I've always been a cash back sort of guy because
for us, we're not doing a whole lot, weren't doing
a whole lot of traveling.

Speaker 1 (22:08):
We've found four young kids will do that to you.

Speaker 2 (22:10):
Yeah, it's decade of having babies and staying home and
not traveling. That changed last year. But yeah, are you
a fan of the Southwest Companion Past?

Speaker 1 (22:19):
Is it? I think here? Southwest Pass is amazing. It's
still as good of a deal as I'm macking it
out to be.

Speaker 3 (22:24):
The Southwest Companion Pass is as good of a deal
as is the number of dollars you spend on Southwest
on flights that one person also comes with you on.
So if you spend five hundred dollars a year on
flights and your partner or friend is traveling with you,
then it's worth about five hundred dollars.

Speaker 1 (22:40):
Yeah.

Speaker 3 (22:41):
If you spend eighteen thousand dollars a year flying around
the country and you bring someone with you, then it's
worth eighteen thousand dollars. So it's a really different flight
on how how many flights you take and when you
earn it, because you get it the year you earn
it and the next year. So if you earn it
in December, you get it for thirteen months. If you're
on it in January, get it for twenty four months.

(23:01):
So there's a little bit of nuance there, but opening
two Southwest credit cards and sometimes there's a promotion whereas
just one can get this for you. And so I
think ultimately the one hang up I have with cash
back is that the sign up offers on cash back
cards are often just not as generous as the sign
up offers on points cards. And so I put together

(23:21):
this model where I looked at the top twenty sign
up bonuses on all credit cards few months back, and
on average they earned about sixteen percent back. And that
was just looking at the value of the points. Right,
So you might open up a credit card that gives
you two hundred and fifty thousand points. You could cash
those points in even if you didn't want to try

(23:42):
to reward them for travel, you just wanted to convert
them to dollars. You could find a way to get
one to one point one cents for those points. And
so if you you know, it's like over two thousand
dollars of value for opening that card, most cash back
cards have a kind of sign up bonus of like
two hundred and fifty three hundred and four hundred bucks.
So the highest ROI on your spending, to the tune

(24:03):
of sixteen percent back is going after the biggest and
best sign up offers. And so if you want to
maximize the way you spend your money, you should always
be putting money on a card that has a sign
up bonus. And if you're worried about your credit, then
I would just say don't because most people that sign
up for twenty cards a year end up increasing their
credit and not decreasing it.

Speaker 1 (24:22):
Which you got to pay attention to your credit score
because you won't qualify for some of these cards if
you don't, and you could ding it if you don't
use them.

Speaker 3 (24:28):
Aropri Yeah, and you might get a bunch of credit
cards and you have a bunch of inquiries on your
credit and then you're going to go get a mortgage,
and that could be a problem. So I would say,
like within six to twelve months of any major loan
you're taking out, you know, playing this game really hard
could be less advantageous.

Speaker 1 (24:43):
But if you you know.

Speaker 3 (24:44):
Got a mortgage a year ago and you got a
car six months ago and you don't have any intent on,
you know, really tapping a major, major lending credit situation.
Then I would say it's a it's a game, and
you can play it. I don't even play it that hard, though, Yeah,
what do you what do you mean to be?

Speaker 1 (24:59):
Play like? I'm not.

Speaker 2 (25:00):
There are people that's cards right four to five thousand
dollars annual piece.

Speaker 3 (25:04):
But I would say the average person that's really playing
this game hard is probably opening up ten to fifteen
cards a year new cards. I've tapered that back a lot.
I probably am like four cards a year, and so
I am not optimal, right because if I am going
to go put money on a card that's not earning
a welcome bonus, there's no world on any expense I
know where you're going to earn much more than like

(25:26):
six percent back maximum, but usually it's probably like three, two,
four and so versus the sixteen you'd get from a
sign up bonus. But it's just a lot to be
like I'm going to open up a new card each
month and and collect these people.

Speaker 1 (25:40):
Do you have like a spreadsheet where you keep track
of everything? Like, how do you do okay, because you
have to, because you'll get lost in the shuffle.

Speaker 3 (25:45):
There are some apps travel freely, card pointers that you
can sign up for that you know very you know,
low cost or free that will manage. Like, here are all
the cards I have. Remind me when my annual fees
are due. Help me make sure I, you know, do
the right thing. Back to annual fees if you're about
to if you have a card with an annual fee,
very often, if you call or live chat with the
bank and say, hey, annual fees a lot. I've had

(26:09):
the annual fee waived the second year I've had. Well,
if you can put another three thousand dollars on it,
you know, in the next three months, we'll give you twenty.

Speaker 1 (26:15):
Five thousand points. It's like, okay, well that negates half
the annual fee.

Speaker 3 (26:19):
So you can negotiate their annual fee with retention offers
if you want.

Speaker 1 (26:23):
What would you say to someone who's saying, all right,
I like the idea of getting free tickets to Spain
or something like that, and I use my credit cards responsibly,
so I'm pretty sure I can do this without like
screwing it up in a major way. But how do
I know which card makes the most sense for me
given my circumstances in the way I spend.

Speaker 3 (26:40):
So I think there's the question of which card makes
the most sense for me based on how I spend
If I don't want to play this game too crazy,
And that's just looking at how much do you spend
and where? Right, If you're spending all of your money
on travel and dining, there are cards like the Chase
Sapphire Preferred the Chase Sapphire Reserve that are like two
or three points per dollar on those categories. If you
spend all of your if you have a contractor business

(27:02):
and you spend all your money at home depot, Like,
there's not a great home Depot card or card that
earns a lot of points at home depot. You might
be better off with a card like the Venture of
the Venture X that's just two X on everything, or
you might be better off going for cash back. Right,
the robin Hood card is now three percent cash back
on everything. US Bank probably by the time this comes out,
is supposed to have a card that earns four percent

(27:25):
cash back on everything.

Speaker 1 (27:27):
Wow, which is pretty competitive. You do have to have.

Speaker 3 (27:31):
It's like a varying rate of two to four percent,
depending on how much you keep at US Bank. So
if you transfer an Ira or a brokerage account and
you have over one hundred one hundred grand in a
US Bank account, it doesn't have to be cash, it
could be an old Ira or something, then they'll give
you four percent.

Speaker 1 (27:46):
On everything is pretty solid. I mean, anyone listening and
that's on anything. And it just makes it easy too.

Speaker 2 (27:52):
You know, you're a usage that could be an easy and.

Speaker 1 (27:54):
So here's what I'll call a hack.

Speaker 3 (27:58):
I used to think that the points, like I still
believe points are incredible because we stay at a hotel.
That hotel costs three thousand dollars a night, and it
was one hundred and thirty thousand points a night, and
so I'd much sure to use my points. But here's
the thing. Those are Hilton points. And you can earn
Hilton points by signing up for a Hilton credit card,
getting to sign up bonus of points, spending money on

(28:19):
it and all that.

Speaker 1 (28:19):
That's great. You can also just buy those points.

Speaker 3 (28:23):
And so what I've come around to is that there
are a lot of people that come to me and say, gosh,
sometimes I want to book a trip and like there
just aren't ways to book it with miles and points.
That's a good deal, but I have all these miles
and points. Alternatively, you could focus on earning cash back
and then just buy the points if you find a
good points and miles deal. And I looked last year,
and most miles and points programs points go on sale

(28:45):
anywhere from like two to twenty times a year, and
so Hilton points regularly, like probably twenty times a year
go on sale for half a cent. So you want
one hundred thirty thousand points to book a room that
costs three grand, you can buy them for six hundred
fift dollar just on hillt Like you go there, say
I'm about to book this hotel, it's super expensive. What
if I just go buy the points and then book

(29:07):
the hotel with points right away? You don't even have
to play the points game. You could have been playing
the cash back game your whole life. Yeah, and then
see France has this amazing deal where you can get
a five thousand dollars ticket for forty thousand points or something,
and then you could just go buy the points, and sure,
maybe it would have been a better deal if you
had been earning those points in the first place.

Speaker 1 (29:27):
But I would say that eighty.

Speaker 3 (29:29):
Percent of the value that you get from having points
and miles is from the points in miles to the
value of the ticket or the hotel, and so you
basically you can buy almost any point for less than
two cents. So any value over that you can get
from buying points, it's like that little marginal difference of
like are you getting it for one cent or two cents?

Speaker 1 (29:49):
Like if you if you earn the.

Speaker 3 (29:51):
Points on your card, it's probably a little cheaper, but
you lose the flexibility. So I would have no problem
with someone listening and say, I want to keep it simple.
I'm gonna go get this robin Hood card US Bank card.
I'm gonna earn three to four percent cash back on everything.

Speaker 1 (30:03):
And if the.

Speaker 3 (30:04):
Hotel I want to stay at for my big trip
happens to be a bit available for points, maybe I'll
just see if I can buy those points on sale
and get that huge arbitrage where you can save eighty
percent yea without having to earn those points in the
first place.

Speaker 2 (30:16):
What's the longest that you've waited for those points to
go and sale. I mean, I guess depending on the
issue or you're saying that it happens fairly frequently.

Speaker 3 (30:22):
But yes, So I think that's the big challenge is
if you want to book it, if you want to
book it right then maybe they're not on sale. You
have to pay point seven, maybe you have to pay
point a like it really depends on the program. The
strategy I like, and this takes a little bit of
knowing your travel style. Is like, Okay, I've decided and
this is a hypothetical. It's like I've decided I want
to take a big trip, and I know I'm probably

(30:42):
gonna stay at these four or five places. They're all Hilton's.
Hilton Points are on sale. Let me buy enough points
to book that trip, and I'll keep that in my balance,
and then when that trip happens, I'll use them, and
the next time they're on sale after that, I'll buy them,
so you kind of always have the points waiting. Now
I realized that might take a little bit of an
upfront commitment.

Speaker 1 (31:01):
Like your point pantry, y store them for when you
need them.

Speaker 3 (31:04):
So for me, I played the points game. Now I
have those balances and all be a great name for
an Applets steal it this Points pantry.

Speaker 1 (31:09):
You can have that one. Yeah, you build it with
chat VPT. It's got a nice little rustic right home.
We feel too, exactly like Benny Crocker.

Speaker 3 (31:15):
Yeah, So I would say if you play the points game,
a little build up a balance everywhere, see how you
use those points, and when you realize, gosh, it seems
like every trip we've taken, and this is true for us,
it seems like Air France or Air Canada Aeroplan is
ninety percent of the way we've used our points for flights.
We're not transferring them anywhere else. It's those two programs.
So now that I know that, that's pretty much how

(31:37):
I'm booking all of our flights. Once I have no
Air France or Aeroplan points, next time they're on sale,
it's probably worth a little bit of an investment because
I know I'm going to be able to use them
because I understand it. So maybe if you already have
some points, or you open up a card for a
really great sign up bonus, see how you use those
points for travel, and once you kind of get a
sense of your way of travel and using points down

(31:59):
the road, the thing and buying points could make sense.
But I can see how it's daunting. But there are
multiple cases where someone has come to me and said,
I really want this deal, and I was like, oh,
it's such a good deal. If you just had these points,
and they're I don't have them, I'm like, well you
can buy them, and like it will never occurred to them.
It never occurred to them. There's actually companies online that
will say, hey, you want to buy this ticket that's

(32:20):
three grand, We'll sell it to you for two grand.
And the reason they're selling it to you for two
grand is because they can get it. They're buying points
on like a slightly shadier marketplace of points buying than
just going to the airline in the hotel's websites. But
the cool thing and the reason why a lot of
this works is that there's three major airline alliances, Sky Teams,
Star Alliance, and One World. And so if there's a

(32:42):
flight to Europe that you think, well, I really want
to take this flight and it's on United, the best
deal might be Aeroplan, and so you might be better
off with Aeroplan points over United or Avianca or Luftanza
or you know, any other Star Alliance partner. But if
the United points are on sale right now, Like you're
not necessarily waiting for one airlines points to go on sale.

(33:04):
You're waiting for any of the partners in the alliance
to go on sale. And so if every airline's going
on sale like once a month, and there's twelve airlines
that you could pick, you might not get the best
deal ever, but you'll probably get on a significantly better
deal than just waiting for or just buying to take
it out right.

Speaker 1 (33:21):
Yeah, you've also talked about ways to earn points that
don't involve spending, right, So you don't just have to
swipe or insert now or your credit or tap to
pay in order to get the points back to your
account through just what you're spending. What are the other
ways in some of which you've said, like you could
split the check right and then have other people pay
you via Venmo, but that can be annoying and frustrating

(33:43):
and weird on relationships. But there are ways that like
don't involve spending at all. Right, Yeah, so I did
this episode.

Speaker 3 (33:47):
I think it was like fifty plus ways to earn
points without spending more, And that was my goal was like,
sometimes people want points, but they don't want to just
go out and spend more money, because that's not responsible.
Like I always say, if you have to pay fees
to use your credit card, worth it. If you carry
a balance on your card and you're paying interest, definitely
not worth it.

Speaker 1 (34:04):
If I'm buying stuff you otherwise wouldn't have purchased, yeah,
that's not worth it. Right.

Speaker 3 (34:08):
Maybe if you're trying to create a reselling business, it
could be worth it, but that can be a little tricky.
I think where it's interesting is every time I'm looking
to buy something on the internet, I think everyone's like, okay,
I want to find a good deal. It's like, okay,
that's fair. So I have like a checklist in my
head that I should probably write down everything I do.
So I'm like, one, if it's on Amazon, I'm just
gonna look at I have this browser extension, KIPA, and

(34:30):
it just shows like the historical price. I'm just looking like,
does it happen that this thing that's fifty dollars is
always forty dollars and like in the last day it's
been fifty then, So that's one. I'm always looking at
cash back monitor to see if there are places that
I can earn points or cash back on the purchase.
A lot of times there are partnerships. So I went
through a lot of them in this episode, so I

(34:51):
won't mention all of them. But like Verbo and Airbnb
and Uber and Lyft and Starbucks, they all have partnerships
with different airlines and hotel groups. So it's like, oh,
link your jet Blue or book your Verbo on jet
Blues website and get extra Jet Blue points. Or if
you're flying jet Blue, I believe you get somewhere between
one and three Jet Blue points per dollar if you

(35:12):
shop on Amazon from your jet Blue Wi Fi. So
if you ever happen to be about to spend a
lot of money on Amazon and you have a Jet
Blue flight coming.

Speaker 2 (35:20):
Out, make sure you're doing sure you spend it while
you're on Jet.

Speaker 1 (35:22):
Blue while you're in the air. Yeah wow, And so
you can go to that.

Speaker 3 (35:26):
If you use Rakotin, which is like a major cash
back portal, you can link it with your Amex account
and convert all those all that Amex or all that
cash back into Amex points. There are just countless programs
that earn cash back when you're shopping. There are portals
that are like get a mortgage through this thing. Now,
I wouldn't get a mortgage that's a worse deal than

(35:47):
another mortgage, right, But if there's a portal you can
book your mortgage through and get points on it, why not.
And so I'd say, I'm always looking around for what
are these things? And I tried to make like a
full list of them so people can go one. But
I would not encourage people to spend more money than
they're already spending. I would encourage them to get creative.

Speaker 2 (36:07):
Would you encourage them to go ahead and buy the
silk underwear, the silk boxers if.

Speaker 1 (36:13):
That, I mean, if you've got sax credit to burn.

Speaker 2 (36:15):
If they're otherwise like one hundred percent cotton kind of guys.

Speaker 1 (36:17):
But I don't know, you do look very comfortable right now,
incredibly relaxed.

Speaker 2 (36:22):
I'm curious, Like it seems a lot of the best
card sign up offers that are out there are for
business credit cards, and so talk to us about what
it takes to qualify as a business. I think there's
a lot of folks who are thinking, well, you know,
like I've thought about starting something official like business off
on the side.

Speaker 1 (36:40):
But I mean, yeah, like speak to that.

Speaker 3 (36:42):
I mean that is a business in the eye there is.
In the United States, you can have a legal entity
of a business, but you also have a sole proprietorship.
And many of the businesses that people run in this
country are sole proprietorships, which means all the business revenue
and expenses live on your tax return. You didn't create
a legal entity for it. Even if you did, like
an LLC is not a tax entity. It's a legal entity.

(37:05):
But if you don't have a business, and you don't
have an EIM that you've created with the irs for
your business, you might still have a business.

Speaker 1 (37:12):
If you have a thing.

Speaker 3 (37:14):
That you think one day will generate revenue, that's a business.

Speaker 1 (37:17):
Right.

Speaker 3 (37:17):
You do some freelance work, you've driven for Uber, you've
been a task grabit, you've sold some art at a
market like there's almost like if you've generated money from
almost any place except your W two employment job, you
probably have a business. And if you have a thing
that you think could become a business, your blog, your Instagram,

(37:38):
like I would say, show me a person who doesn't
do at least one thing some could be qualifying them
as a business, and I would be surprised. Yeah, So,
and you're right, A lot of the business cards not
only have better offers, great earning rates, and often lower
annual fees.

Speaker 1 (37:55):
So there's a whole.

Speaker 3 (37:56):
Lineup of business cards with you know, ninety to one
hundred thousand point sign of bonuses with zero to one
hundred dollars annual fees.

Speaker 2 (38:05):
Is that typically because the issuers are the banks are
expecting you to run more expenses through it with it
being a potential Yeah, I mean I only fledged business.
And they're like, well, this holds the potential of you know,
of them racking up hundreds of thousands of dollars of expenses.

Speaker 3 (38:18):
Businesses spend more money than people. Yeah, that's just the reality.
And so if if you might start a business, and
if bank can get your credit card business and that
business grows, you're gonna probably put a lot more through
your business than your personal I know, I do. I
probably I put a lot on both sets of cards,
personal and business. I don't know what the it's not

(38:40):
a problem, Like, it's not a legal problem. If you
put a personal expense on a business card or a
business expense on a personal card, you have to keep
track of it. So, like the argument for keeping them
completely separate is more of a bookkeeping and accounting argument,
sure than anything else. But people sometimes ask me like, Oh,
I got this business card, and I'm not sure if
I'm going to be able to spend the three thousand

(39:01):
dollars to get the bonus from this business. It's like, well,
you could put groceries personal expense on it and have
the personal pay off the business card.

Speaker 1 (39:10):
That's not the intent of the card, but it's something
that could happen. Yeah, what are the biggest misconceptions about
credit card rewards points? I don't know. Part of I
guess part of my hesitancy at times is I like simplicity,
and I'm like, how many websites am I going to
have to log into? How many account balances am I
going to have to keep track of? How many credit
cards am I gonna have to have in my wallet?

(39:31):
That's one thing I guess for me is like, is
this just going to overcomplicate my life? Granted, if I
get a free trip to the Seychelles, I don't know,
maybe it's worth it, but tell me, what is that
A common of these myths, So one, how many cars
you need in your wallet? I would argue that my
wallet probably carries less credit cards than both of your wallets.
Could be wrong.

Speaker 2 (39:51):
I got pretty minimal as well to more than two.

Speaker 3 (39:55):
Okay, so with Apple pay, Google Pay, Samsung like, you
don't need a physical card for almost anything. I would
say that the only physical card I have. I keep
one card that's kind of blanket everything card just.

Speaker 1 (40:09):
In case someplace doesn't take Apple pay or whatever yep.
And then one card for dining.

Speaker 3 (40:13):
Whatever my card is for dining I keep with me
because some restaurants in the US don't have to have
to pay. And then one card for everything. You know,
you gotta pay for the ticket to get I actually
did that online for the mark.

Speaker 1 (40:25):
Here in Atlanta.

Speaker 2 (40:26):
Well, don't you also need to have your Costco membership
credit card on there as well in order to get
into the.

Speaker 1 (40:31):
Digital Do they really? Yeah? But do you have that?
I do.

Speaker 2 (40:36):
I don't use it though I don't even know exists.
I'm always carrying around because.

Speaker 1 (40:40):
Of the the emergency you need to go to tattoo
it on his and he just lives up his shirt.

Speaker 2 (40:46):
Why do they this is a side thing. Why do
they make you show your card to even get in?

Speaker 1 (40:50):
If there? If you can't do wander around aimlessly, but
they don't want you to think you don't need a membership.
People walk into Costco, fill up their card, get all
the way to check and you can gotcha. I think
they shake at that point. It's probably an easy got
them your committee. It's gonna be sixty bucks exactly. Yeah.

Speaker 3 (41:05):
Sorry, anyway, Yeah, you're talking about one misconcept. You don't
need to carry all these cards around. Yeah, that's not
that tough. I think knowing which one to use can
be tough if you were to jump from zero to sixteen, right,
But if you do it over time, I think that's okay.
There's an app called card Pointers that you know, you
kind of load in all your cards. They don't actually
sync to your bank, so you're not sharing any of

(41:26):
your personal information. You just say I have this card,
and then they say, great, this is your dining card,
this is your this card. So if you don't want
to figure that out yourself, their apps that will do
that for you.

Speaker 1 (41:34):
Nice.

Speaker 3 (41:35):
Let's see other misconceptions. The whole blackout date thing, I
think is something that kind of came up back when
airlines used to have really fixed prices. They'd say we
have miles flights and non milesflights. Now it's a little
bit more mysterious. Most of the airlines have these dynamic
pricing where they will give you a ticket with your
points on delta. Sometimes that ticket might be four hundred

(41:56):
thousand points for the same route, and then the next
day it might be fifteen thousand points. It's like you
have no idea what it's gonna be, which is a bummer,
but it means there's no blackout dates. But what has
come up in the last two or three years that
has made this so much easier is all of these
both free and paid award search tools. So I'll give

(42:16):
you an example of one that I really like. Points
Yeah dot com y e ah, And if you go there,
they have this thing called Daydream Explorer, and they'll just
show you great deals with your points, like incredible deals.

Speaker 1 (42:28):
I like that because then I can let let the
deal drive where I go, instead of being like trying
to find the square peg in the round hole of
like this date for that destination.

Speaker 3 (42:37):
Yes, now, to an extent, you don't want to necessarily
let the points decide what you do. Like, is the
trip deciding you? Are you deciding the trip? I'm not
gonna go to Antarctica just because it's cheap, you know,
I mean, I don't know Antarctic, but yeah. So from
a finding a great way to use your points, generally
you used to have to log into like seven or

(42:57):
eight different websites search on all of them. Now there
are a handful of tools. Another One's award tool, dot Com, Point,
dot me, seats, dot arrow if anyone listening wants to
kind of go down the rabbit hole, those are kind
of four that I use regularly for different reasons. I
did an episode going over like the ten of them.
But Points, he has a great place to start, and
you can find great options. I think if you're the

(43:18):
kind of person that says, oh, my family and I
we want to take a trip, and we want to
go to Barcelona this summer, and we really want this
one direct flight on this one day, you're gonna probably
just need to get lucky for your Points to ever
be a good deal. But if you're someone who says, gosh,
this summer, we've got two months and we're kind of
flexible to go somewhere in Europe and we're willing to
change planes no problem. Now the day you look, it

(43:40):
might not be there, but I'll set up an alert.
And this is how we ended up going to Paris
this past summer. We just set up an alert and
we said, hey, we need five tickets. We want to
fly from San Francisco. We'll go to one of these
six cities in Europe direct. We want to do it
in business class, and we want it to be under
I think it was like under eighty thousand points. We said,
just let us know when you find something, and then
it popped up. It was like we found something and
we're at great well bucket.

Speaker 1 (44:00):
Yeah that was points.

Speaker 3 (44:02):
Yeah, that was award tools alerts okay. Points Yeah also
has alerts.

Speaker 1 (44:06):
Okay.

Speaker 3 (44:08):
But so if you're willing to be flexible, you will
get an incredible value. If you're sitting on a few
hundred thousand points and you want to take a trip,
and I say a few hundred thousand, which might seem
like a lot, but everyone in this room has a
lot of family members in our old family. If you're
single by yourself, fifty thousand points can take you lots
of plasure.

Speaker 1 (44:25):
But if you're talking five or six seats, it's like
gets pricey real quick. It gets pricey.

Speaker 2 (44:29):
Chris, you want to loan me sixteen million points or
maybe not next next time we take.

Speaker 1 (44:34):
A tur he's got plans for those. Yeah, yeah, now.

Speaker 2 (44:37):
It might actually be a good time to take a break.
We've got more to get to. We're gonna talk more
about ways that you can redeem those points for even
more value.

Speaker 1 (44:44):
We'll get to that and more right after this. All right,
we're back. We're still talking with our buddy Chris Hutchins,
who's right here with us in person, which is so nice.
When did you meet Chris? By the way, do you
recall it was? It was at a fin con I
want to say, yeah, mutual friends. And it was before

(45:05):
you started the podcast. This was back when you had
an entrepreneurial startup. You were getting off the ground in
the midst of grove growth. Okay, I want to keep
talking about points for just a second. I'm curious you
talked about the sixteen but trillion points or whatever you have.
That's like the number my son would use. But we've
talked too about how over time your points become worthless. Right,
there's inflation in the points game too, So how do

(45:26):
you think about all the points you're holding? Does it
stress you out? Are they garning a hole in your pocket?
Are you like, I gotta go take some trips because
these are going to be worth less next year and
the year after.

Speaker 3 (45:35):
You are one hundred percent right, And if I could
go back in time, I don't know if I would
have done it differently. But I have more points than
I am using each year. I don't have as much
of a desire to do all these sign up bonuses,
so I will probably net burn points each year going forward,
or at least that's what I keep telling myself. But

(45:56):
I'm also we have two kids under five, and so
the last five years there's just been no great opportunities
to use lots and lots of points. This trip I
talked about in Paris, we finally got the five tickets,
and then we decided to cancel it because we're like,
what are we doing taking a two and a four
year old to Europe?

Speaker 1 (46:11):
Like, just this is if the deal's great. Even if
the deal is great, it sounds like it's not a vacation. Yeah,
And so I think that I would rather I know
the value I can get from them, and even if
I get a fraction of that a few years from now,
it's probably better than cashing them out for you a
penny a point.

Speaker 2 (46:28):
Would you take some some of the points off the
table where you're like, all right, well, I know if
I take this off the table, now it's converted to cash,
still have let's say eight million points sitting there.

Speaker 1 (46:36):
I think the trade off.

Speaker 3 (46:38):
I think, knowing what I can get from these points,
like using them in ways that I would use them,
I probably if I don't use them in the next
seven years, then it would probably not be worth keeping
them all because of how I think they'll devalue. Though,
when this recent merger between Alaska and Hawaiian sparked a

(46:59):
bunch of conversations in kind of regulatory agencies in the
United States, which one of which was one stipulation towards
Alaskan Hawaiian was if you are going to complete this merger,
you cannot devalue each other's points. And then this kicked
off this thing where I want to say to DOJ
but I can't remember. Sent a letter to United American
Delta and said, you need to justify why your points

(47:20):
are getting so devalued, as if it's like a cost
on the consumer. And so realistically, I think at domestic
US based airlines are probably going to be pretty hesitant
in the next twelve to eighteen months to devalue any points,
given everything that's happening about it now. But because the spotlight, yeah,
they're they're asking why are you doing this thing?

Speaker 2 (47:40):
And because of Leena Colon fails, probably the f DC.

Speaker 3 (47:44):
Yeah, so there is there is a bit of scrutiny
towards airlines for devaluing points. So I don't think you're
going to see as much of it in the next
eighteen months. But obviously that's just my speculation. And I said,
most of the points I use are in international carriers
and they're obviously not subject to any US oversight Noway,
so who knows, But I think I think that when
our kids. Right now, my wife and I both work

(48:06):
for the podcast, and so we have flexibility. We're years
away from our kids being a little bit easier to
travel with, and so it wouldn't surprise me if in
the next three years we took a couple summers and
did some real fun, slower but farther travel, and boy,
it would be nice to have all these points to

(48:27):
do that.

Speaker 1 (48:28):
That's true. Okay, we're getting close to the end.

Speaker 2 (48:29):
Here, do you have any I guess final thoughts when
it comes to just the average person out there who's
looking to you know, they're looking at some of the
different ways that they can maximize their their travel rewards.

Speaker 3 (48:39):
Chris, I think a lot of times you listen to
people on this podcast, on my podcast, and you're like, gosh,
those people are really dialed in. That seems so far
from where I am today. And that's true, but that's
not where I started. And so you know, this all
started with let's get one card and use that sign
up bonus to take one trip. And I was like, wow,
I took a trip in college to Mexico that I

(48:59):
couldn't otherwise afforded on American Airlines points that I got
from an American Airlines credit card opening is that literally
true story? And I was like a freshman and I
went with these like sophomores and juniors going to Mexico.

Speaker 1 (49:11):
I was like, this is the coolest trip ever, but
I literally didn't have the money to take that trip.

Speaker 3 (49:14):
Yeah, And all of a sudden, I was like, oh,
now I get how it works, and I promise that
this is the kind of thing where you do it
once you see how it works. You go on that
trip and then you're like, now I feel a little
bit more comfortable getting a second card.

Speaker 1 (49:26):
I'm not the bug. Yeah, I'm not telling people to go.

Speaker 3 (49:29):
Out there and go open sixteen credit cards. That would
be aggressive. I don't even do that. These are many
of these cards that I have. I've had for you know,
some even a decade or longer. So I think you
can get started slowly with the caveat that if you
can't pay the cards off in full every month, this
is not a game for you. Clear clear caveat, and
just keep an eye out for when really exciting offers

(49:50):
are coming out.

Speaker 1 (49:50):
I don't know if you guys talk about them on
the show.

Speaker 3 (49:52):
I sent out a newsletter each week, and if there's
something exciting, I'll put it in there. If there's not,
I won't. And that' one way. But you guys probably
have links to cards on the site also.

Speaker 1 (50:04):
Yeah, yeah, and we have a little tool if you
got to have the money dot com here the credit
cards buttons. There's literally a thing where you can click
and see which which credit card maybe makes the most
sense right now, based on sign up bonus, based on
how you spend, based on what sort of points you're
trying to based on an airlines. Yeah, yeah, I think
that's important to mention though, too, Matt or Chris, because
in I think, like let's say, in the Real Estate

(50:24):
Influencer game, there's so many people trying to sell something
that's like way more than most people want or can
get to can achieve. And I think the same thing
is true in the travel rewards points game so much
at the time too, it's blown up through this massive thing.
And I appreciate that kind of start small, ghost steady.
You'll get somewhere great and you might not need to
overcomplicate things in the process. You might just be able
to like crush, you know, in a small way, get

(50:47):
some free trips and enjoy your life and enjoy the
savings because of it.

Speaker 3 (50:50):
Yeah, and ask yourself, what what is your time otherwise
spent doing? Because I'm giving this talk at the end
of the week about the points of Miles game, is
it worth it? Which is where we start of this conversation,
And depending on what your time is otherwise doing, maybe
it's not worth it. Right if you're in the middle
of building a business and that business could be you know,
you could build a business that you know, your kids

(51:11):
and their kids and their kids could could own and
work for and all this stuff. Well, that's probably gonna
be way more impactful than getting a free trip this year.
But if you're working at a job and you got
a little time on the side, and you're not trying
to start a new projects, and you're not dealing with
you know, two to four kids running around the house,
maybe this is the way you can plan for a
free vacation. The easy version of this is not that hard, right,
You guys are both, in some way, shape or form,

(51:32):
playing the credit card game by just not using a
debit card. Like, if there's one thing you can take away,
it's use Like no matter which card you use, you
can earn no less than two percent back, Like you
should not be earning less than two percent back on
everything you spend money on.

Speaker 1 (51:47):
Yeah, and if you want to go beyond there, and
now with we talk trash about debit cards all the time.

Speaker 3 (51:52):
Yeah, now with the robinhood, maybe three percent you know
on everything, So like that's your threshold you want to
optimize beyond that? Great, you know, come talk to me
or come find any of the content I'm making but
you don't.

Speaker 1 (52:04):
That's okay too. I'm curious. So your your show's called
all the Hacks. You've talked to a lot of hackmeisters,
that's what I'm calling. That's the term on your show.
What is the thing maybe in all of those chats
that you've had that you've taken away into your own
personal life more than anything else.

Speaker 2 (52:19):
I would if okay, So this is this a way
for him to plug his most impactful episode that's impacted
him personally?

Speaker 1 (52:25):
Is that us? Okay?

Speaker 3 (52:26):
Oh, okay, that makes it easier because I know that
one and I don't know if you've had this conversation
on and just caution to anyone sensitive to inappropriate language.
My guest in this episode was full of it. But
Bill Perkins, Yeah, have you had Bill Perkins on this? No,
we haven't, Okay, So Bill Perkins wrote this book, Die
with Zero. We've talked about the book and the concept,

(52:46):
but we've never had them line. So for anyone who
wants to go get a like a crash course in
this concept, that episode was really really impactful for me
because what's the point of all this money?

Speaker 1 (52:56):
Right?

Speaker 3 (52:56):
Like you can just earn money endlessly and you know,
I'm here in Atlanta for a conference for a bunch
of financial content creators, and we had a conversation this
morning about like, oh, what new line of business are.

Speaker 1 (53:09):
You going to launch?

Speaker 3 (53:09):
How are you going to grow this? And I was like,
at what point do we stop spending our time trying
to make more money and start deciding how we want
to spend our money and so in our time and
our time, And so the book's premise is just don't
accumulate wealth for the soul's sake of accumulating wealth. Right,
there are times in life where it might make more

(53:30):
sense to spend money than to earn more money or
save that money. And especially when we're younger and we
can go on these one mile walks to the office,
we can go run around with all of our kids,
like there are things that you might wish that you
did or spend money on now twenty thirty forty years
from now. And every conversation to go back to the beginning,
you know, my relationship with my wife, it started with, Okay,

(53:53):
here's how much money we have. What's our next target?
What's our next target? Oh, we want to have this
many you know, dollars in the bank. What net worth
goal do we have? And after that conversation we went
to one of these like catchups with my wife. She
was like, this is the target and I was like,
i don't care about the target anymore, Like I'm no
longer focused on getting to a place, because maybe the
answer is we should actually not save money this year.

(54:14):
Maybe there's an opportunity to do something that's.

Speaker 2 (54:16):
Literally what I'm doing this year. It's not saving money, Yes,
I mean I'm saving money. I'm not investing it though,
because of other goals. Yeah, there's bigger, larger, more impactful,
loftier goals.

Speaker 1 (54:24):
To Matt loss and focus on all his treat credit.

Speaker 3 (54:26):
When you said that, and I think I left that
conversation with Bill Perkins and I was like, I have
a completely different mindset on how I want to use
my money in my life for the rest of my life,
which very rarely happens in a moment.

Speaker 1 (54:39):
And so I wass a powerful message. I'd say, in.

Speaker 3 (54:43):
Almost two hundred episodes, I've probably picked up hundreds of
tactics that I use all the time for various things,
but that one kind of hit me like a freight
truck in terms of the way I think about money
and how I want to use money.

Speaker 2 (54:54):
There's a paradigm shifting kind of conversation as opposed to, oh,
here's another new tip, yes and the tips.

Speaker 1 (55:00):
Yeah.

Speaker 3 (55:00):
I love saving money. I love learning how to optimize
everything in my life. Like you guys know this.

Speaker 1 (55:04):
The guys, I've always got some random, crazy thing I'm
doing to try to eat better, nutrition, you know, exercise,
health career points, miles, investing, Like I love all of it,
but at the end of the day, at the end
of the day, it doesn't matter. But I'll let's day.

Speaker 3 (55:21):
We all have children, and it's like, what is the
whole purpose of life?

Speaker 1 (55:26):
And I'm not going to go down that rabbit.

Speaker 3 (55:27):
Hole here, but you start going down that pathway, yeah,
you start thinking like how do I want to spend
my time? And you know, you probably had this conversation
here about people asking if they'd trade places with Warren Buffett,
and it's like, well, no, no one wants to trade
places to Warren Buffett, even though he has all his money,
because look how old he is. He's there, and look
at the cost it took him to get there. Like
my understanding is he didn't have a great relationship with

(55:49):
his kids and his wife. Like someone asked me, would
you trade places with and you can insert almost anyone
and if you look at what that person also has
in their life, right, not just you can't trade places
with someone and just get one aspect. So think about
it anytime you get jealous, anytime you get jealous of anyone.
And this happens a lot with money. I've been there

(56:09):
for sure, dozens of times. But ask yourself, oh gosh,
I'm so jealous this friend of mine just you know,
worked at this company, hit this lottery ticket, got all
this money. But if I'm jealous of them, I have
to be jealous of the whole them, And very rarely
am I actually.

Speaker 1 (56:22):
Jealous of it.

Speaker 3 (56:24):
Together, the toll on their family, you know, where they
had to live, what they had to do, the sacrifices
they made. And so I just learned to kind of
appreciate where I am and want what I can do,
and not want that much more. And not to say
I don't want to be ambitious. I want to go
do amazing things and build crazy projects.

Speaker 2 (56:42):
It's a hard balance to strike though, Yeah, you know,
like and I think we are all here trying to
achieve that So how much of that sort of lifestyle
philosophical shift do you think had to do with y'all
having kids.

Speaker 1 (56:53):
I think a good part of it had to do
with that. I think a good part of it had to.

Speaker 3 (56:57):
Do with this natural evolution in life where this other conversation,
if you asked me for two, would be a conversation
I have with a kind named Arthur Brooks who's a
professor on happiness, and we had talked about how when
you're young, there's these two curves and I'm going to
blank on them and they'll come back in one second,
where these two mindsets where you have different types of

(57:20):
work throughout your life, and you have this jump from
when you're young. It's all on its intelligence, crystallized and
fluid intelligence.

Speaker 1 (57:29):
I said it would come I knew it would come back.

Speaker 3 (57:32):
So when you're young, you have this fluid intelligence and
you can learn things, and you can try things out,
and you can just grind it out. And then there's
this happiness curve where when you get older and you know,
I'm forty, like it's starting to get there, you build
your career around crystallized intelligence, which is all the things
you've learned, the knowledge you have, you might be a
better manager or delegator than just a grinder. And people

(57:56):
who don't make that jump end up being really unhappy
in life because they're still trying to grind it out
like they did in their twenties. But that just doesn't
work with our brains when we're in our forties and
and for some people maybe it's fifties sixties. You know,
that's not the main point. But I think I got
to this point in life where it's like, wow, I've
seen a lot of things. I've gotten a little older,
and I've started to really reflect on what I want.

(58:19):
By the way, if you look at like life expectancy,
by the time you get to forty, you're like, Okay,
I gotta start like thinking about what I want to
do in life.

Speaker 1 (58:25):
Second half of life. Yeah, yeah, start looking down the road.
You know.

Speaker 3 (58:28):
We talked about Brian Johnson, maybe waalda forever and I'm
the youngest I've ever been.

Speaker 1 (58:32):
But at least in a vat of goo somehow. Yeah.

Speaker 3 (58:34):
But I think it's somewhere between kids and just realizing
that like I'm not a kid anymore, Like this is life,
Like there's only one of them and We're a decent
way through it, and I better be doing what I
care about. And it's just so hard to get caught
up chasing net worth goals and you know, earnings goals.
And if you've traveled at all anywhere, you know internationally,

(58:57):
you've probably met people who have way less than you
and you're like, wow, these people so happy. It's like,
there's just so much more to life. And the more
I talk to people, the more I learned that, and
the more I'm able to change my mindset, which is
not a hack like that, like no, which is part
of the reason I don't like the title.

Speaker 1 (59:11):
That's a slow roll, that's a slow burn, and that's
an intentional thing that takes a lot of time, intentionality, discussion,
I think, and introspection, and a lot of people they
are continuing along just the pure money metric because they
haven't taken the time to think about those deeper realities
of life and what they want out of life. And
I feel like we could this could be a.

Speaker 2 (59:31):
Whole nother podcast conversation shifting gears more philosophical side of things.

Speaker 1 (59:35):
Well, speaking of things we care about, Matt, we care
about craft beer, and craft beer goes beyond just satisfaction
of my taste buds. It warms my soul. And Chris,
you you enjoyed this beer with us? This was called
flash Cat. It's an imperial IPA by Creature Comforts. You're
not a huge IPA fan, But what were your thoughts
on this one?

Speaker 3 (59:50):
I was surprised. A lot of IPAs for me are
just like too much. Yeah, this one was I would
drink this thought. Would you really look at that a
ringing endorsement?

Speaker 1 (59:57):
See?

Speaker 2 (59:58):
I thought Joel was putting words in your mouth because
he's said, you enjoyed this one with us?

Speaker 1 (01:00:01):
Right, Chris? I would it? Yeah?

Speaker 2 (01:00:06):
This West Coast ip it's an imperial so it's a
little higher in the ABV. But yeah, did I say
West coast? It takes like a West coast. It takes
like a West Coast.

Speaker 1 (01:00:12):
Yeah, And so to me it was like the pithy
greapefruit bitterness going on. Yeah, but I guess I don't know,
not over the top. I don't have a lot of
ibas to compare it to.

Speaker 2 (01:00:20):
Yeah, well, glad you're able to join us here in
the studio, Chris, can you tell us where our listeners
can go to find out more about you, more about
your podcasts and all the stuff you're creating.

Speaker 3 (01:00:31):
Yeah, podcasts called All the Hacks. If you're listening to this,
you're in a place where you can search for it. Yep,
I'm Chris Hutchins. You can find me searching All the
Hacks or Chris Sutchions anywhere on the internet. Email and
podcasts are the best two places to see what I'm
doing each week.

Speaker 1 (01:00:45):
Perfect. We'll link to all that stuff in the show
notes too. Up on our side, I have to money
dot Com. That's gonna do it for this episode until
next time. Best Friends out and best Friends Out. That's

(01:01:07):
gonna make a joke about it. I want to be
your best friend. I