The Secret Art of Finding Work You Love and Funding the Life You Want | Chris Hutchins

I think I've gone through the exercise of what does my life cost?

What do I think it would cost in an ideal version?

And what do I think it will cost once I don't have kids and once we've paid off our mortgage?

And what does that need?

When you don't know what the money's for, you know, you need more.

Hello, friends.

This is Tyler Gardner welcoming you to another episode of your Money Guide on the Side, where it is my job to simplify what seems complex, add add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing.

So let's get started and get you one step closer to where you need to be.

Today's guest is someone I've been looking forward to having on the show for a while now, as whenever I google just about anything worth Googling, re practical finance strategies, his name seems to pop up.

Chris Hutchins is is the host of the wildly popular podcast, All the Hacks, where he explores how to optimize every area of life, from money to travel to health, without spending a fortune.

He's been featured in the New York Times, The Wall Street Journal, and CNBC, and his work in the financial independence space even landed him in the documentary Playing with Fire.

But Chris's story goes deeper than hacks.

He's someone who's built an incredible career and life.

Head of new product strategy at Wealthfront after they acquired his company Grove, investor at Google Ventures, co-founder of Milk acquired by Google, and creator of Laid Off Camp.

Along the way, he's managed to collect over 10 million points and miles, which gives him more than enough credibility to call himself a financial optimizer.

But what excites me most is not his ability to optimize.

It's that Chris has reached a point where joy, curiosity, and purpose guide his daily decisions.

He's not waking up every day trying to squeeze one more penny out of his portfolio.

He's living a life designed around meaning, and the money serves that vision.

That's a powerful shift, especially for those of us in our 40s and beyond who want to invest wisely, but also actually live well.

In this episode, we'll dig into practical tools, rethinking the 9 to 5 grind, why we might have it wrong when buying health insurance, and even why pre-paying for things can bring way more joy than paying as we go.

Well, at least for some of us.

But more than that, Chris is here as an example of what it looks like to align wealth with life and not the other way around.

So grab a notebook because this conversation is full of hacks, but it's also also full of perspective.

And it is my absolute delight to give you this week's show with guest, Chris Hutchins.

And before we get into it, if you do enjoy today's conversation, the best way you can help me grow the show is by leaving a quick review on Apple Podcasts.

It takes less than a minute.

It helps others understand what this show is about, and it really does make a difference in reaching more people who want to build wealth and meaning.

Thank you so much, and I appreciate it more than you know.

But I want to start where you and I have left off in a previous conversation, not to get too incredibly existential and philosophical right from the get-go, but you and I both produce lots of content for people to think through wealth and meaning and intentional living.

So I'm wondering if you could start us off by sharing just a little bit about what that has looked like for you throughout your life.

In other words, just to ask the big question, why why are we doing this, Chris?

What's the meaning of life or wealth to you?

So wealth to me started as a way to just keep up in a way.

I went to a boarding school and every other kid had a credit card from their parents or like unlimited money and I didn't.

And so I was like, how do I get pizza?

I don't have the cash to buy the pizza.

So I try to buy pizzas and sell slices so that I could have a little profit to eat.

So wealth to me early on was money that allowed me to do the things that other people could do.

I honestly was one of the people who had no idea what I wanted to do.

So I just asked around and I was like, what are really good jobs?

And a lot of my high school friends were like, oh, really good jobs are investment banking and management consulting.

And so I was like, well, I guess I got to go do those things.

I bought those books, the Vault Guide to Investment Banking, the Vault Guide to Management Consulting.

And I applied for some jobs and I got a job at a management consulting firm and an investment bank.

And I went kind of through that path for a few years.

And I was like, this sucks.

Like, this is life.

There were parts of it I enjoyed, but it was definitely not a meritocracy where it's like, oh, if you had a good idea or you could work a little harder, someone might view you as someone with good ideas.

No, you were just doing the work that someone else didn't want to do.

Straight up, I remember a night where someone said, we've got all this work to be done.

Is it okay if you're here till like five in the morning?

And I told my boss, I was like, well, if you have time to help, we could both go home by two.

And he's like, no, not interested in chipping in.

This is not a team project.

This is a, you're going to pull an all-nighter and I'm going to go home and do something more fun.

Can you unpack a little bit, just the idea of what you didn't like about kind of the first roles that you had, right?

And what it was about some of the other jobs that you ended up liking?

Like, what does it mean to like work versus the things you really did not like initially?

Yeah, it's funny how in hindsight these things can be clear.

I was definitely very entrepreneurial and I liked making things.

And I don't mean making things like in a wood shop, just like turning nothing into something, whether that is a product, an idea.

And I remember in the management consulting firm, we were working for a client that was trying to justify why they should bundle all of the things together to try to charge a higher price.

And I remember we came to this conclusion that like, maybe it wasn't actually a better deal.

Maybe it was actually a worse deal.

And the person in charge was like, yeah, I'm trying to make a case that it's a better deal.

So let's find some data that shows that it's a better deal.

And I was like, this is just performance.

We're not here to try to make the company better.

We're here for like a mid-level executive VP to try to justify a thing so they can keep their job and look good to the senior executives at the company.

And that's not to say all management consulting was like that, but I was on a project that felt like that.

What prompted the actual shift?

And I ask that because I know countless people, right?

Many, many listeners too, who have probably been in roles like this, not just a couple years out of college, but for 30 to 40 years and have just kind of put up with it.

Now, whether that's for the points or staying in the fancy hotels or the nice travel, I don't know.

But what is it that got you out of that grind initially and said, I'm out, I'm trying something different?

Well, the short answer is that it wasn't my choice and I got laid off.

Good answer.

But that came from an attitude that I think just didn't work in that environment.

We were working on this client.

My boss said, how you feel about this work?

And I told her, I was like, yeah, this project's not as fun now that this thing changed with the client.

And she was so worried that I was going to quit as if that was even an option.

It doesn't matter if you don't like the work, you're still going to do it.

One and a half, two years out of college, you're grinding.

But she came from this nonprofit world and she was like, oh my gosh, if he doesn't like it, he's going to leave.

It's like, sure, a nonprofit where you're getting underpaid and like you might need to keep people motivated.

Here, the motivator was, I'm traveling, I'm getting paid well.

And so she just went to the director of the San Francisco office and said, I think Chris is going to quit.

I don't want him on my project.

And so I went into an office with a person I didn't know who told me I was getting laid off for reasons that didn't make sense, but had no answers because I'd never met them and they knew nothing about me.

You know, it was November 2008.

And I was like, okay, well, I guess I don't have a job.

I got to figure something else out.

And I probably knew the industry I wanted to work in, but I still had no idea what I wanted to do and whether doing it would be something I enjoyed.

And did that chapter of your life scare you or excite you or a combination of both?

So about

maybe six, seven months before that moment, I was living in New York and there was this event called Startup Weekend.

And this was kind of, let's say 2007, 2008.

And I drove up to Boston and I spent the weekend sleeping on the couch of this office where they had an event where from Friday night to Sunday afternoon, people built companies.

Not necessarily companies that would take off and be successful, but to kind of go through the exercise of how could you build a thing?

And I thought, I loved the internet, but it had never crossed my mind that the internet and a career were kind of the same thing.

So I went to this event.

And in a weekend, we built an app that you could run on a Windows computer that would remind you to get up and stretch and give you some examples of stretches that you could do so that you weren't just sitting at your desk all day.

It went nowhere.

I think my mom maybe installed it on her computer, but that was kind of it.

But I left that weekend thinking, oh my gosh, like this is a thing people do?

Why am I not doing that?

And everyone's like, well, everyone in San Francisco does that.

That's where you got to go.

So I went to my girlfriend who is now my wife and said, I'd really love to go to San Francisco.

What do you think?

My office has a job there.

I've got this great stable job, which of course I got laid off from a month after moving to San Francisco.

She didn't love what she was doing and she was open to it.

And so the goal of moving to San Francisco was to get into the tech world.

I just thought it would be a little bit later than one month after arriving that, you know, in the middle of a financial crisis that I would make that decision.

But and did you already have a sense of what you wanted to build after that first app?

No idea.

I just wanted to build.

Like I had a sense that I wanted to be a part of making things on the internet.

I loved it.

Now, the reality was I didn't have a skill that necessarily made sense.

So when I ultimately tried to get a job at these startups, I was just, hey, can you hire me?

I will do anything.

Slowly but surely over the next four or five years, it kind of all came together.

How did you go about, so I'm actually going to challenge you on this one in a good way of you say that you had no skill and yet it sounds like you were very good at marketing yourself.

And I think right now we're, especially with Gen Alpha, you you know, going through a relatively difficult phase of like trying to crack into some of these industries, especially tech, like one of those skills that so few people are focusing on in traditional undergrad degrees right now is marketing the self.

How did you go about doing that?

Like you're in San Francisco, you know you're going to need another paycheck and you say, look, like I don't necessarily know what the skill is I'm bringing to the team, but I'm confident that I'm excited about it and I want to sell myself.

What were some of the the techniques you used?

As someone hiring an employee at a small company, let's assume they have to have the ability to do the job.

But assuming they have the skills to do the job, there is no better second skill than just an extreme amount of passion for what your company does.

Now, I didn't know that at the time.

I thought this was crazy, but I looked at all the startups out there.

I went to every event.

I talked to every person I could, trying to understand the lay of the land, what companies were hot, what were they doing?

I'm I'm fast forwarding probably a couple years.

So I spent a couple of years doing freelance work, like helping people build financial models that relied on my investment banking background.

My wife and I traveled around the world for six months, but I'd identified, I went to South by Southwest, which at the time was a kind of small interactive tech conference.

The tech part of it was small.

And I was just meeting companies and I was like, wow, there's this company called Simple Geo.

Everything was firing on all cylinders.

They were trying to take advantage of location.

The iPhone 3GS had just come out.

I was a nerd about mobile phones.

I was someone with like a Treo Windows phone in college.

I thought something cool could happen here.

And they had assembled a team that was just going to build all the infrastructure to make the future of location-based apps possible.

So I put together a PowerPoint presentation of everything I could gather about that industry.

And I had met one person who was an investor in this company.

And I said, I put together this presentation.

I'd love to deliver it to the founders.

If there's any way you could make it happen and he was like well there's a board meeting in our office next week and I'll ask them if they'll stick around for five minutes if you want to stop by and I walked in and I was like here's my presentation here's here's why this is going to be an amazing industry here's what's going on and they were like yeah we know all this this is silly but who is a person that would take a dozen hours to put together a report on an industry they don't even have the job and they ended up hiring me to do what was called business development i didn't know what that was you know it was probably six months before I even figured out what it was.

But at the end of the day, it was try to figure out how you could take a product and sell it, which it turns out overlapped a little bit with my skill of trying to figure out how I could take a product myself and sell it.

And so that company didn't end up working, but I realized that the role of business development and then ultimately while working there, I did a bit of product management.

The kind of bridge between the technical and the consumer seemed to be a skill that I had, given that I had enough technical understanding that I could sit down with an engineer and understand what we could build.

But I spent enough time thinking about it from the consumer side that we weren't building things that just didn't make sense.

And did you have a good team of mentors there?

Or were you largely self-motivated?

Because it obviously sounds like a lot of this is self-motivated, self-taught.

How did you go about learning what is business development?

Like, what are the things I actually need now that I'm in this role?

Because obviously we, you know, we've all heard of fake it till you make it.

And so did you scramble once getting the job?

And what resources did you find, whether that was people or apps or systems that you then utilized to give you some added credibility in this space?

I had one friend who I'd met who was basically on the exact same career path I was, but a year before.

But at the end of the day, it was, I'm going to do everything I can to learn.

I'm going to ask all the questions of everyone.

I'm going to go to every event.

I'm going to talk to everyone I can in the spirit of learning and adding value.

And that turned into

a reputation, I guess, of like, Chris will just do anything, like whatever it takes to get done.

And so when that company stopped growing and ultimately didn't work out, another person in the industry reached out to me and said, Hey, I'm looking for someone to join this company.

We're six people.

And I just need someone that could do all the things.

They had asked around through their network and people were like, Chris is willing to do anything.

And it turns out that if you're really excited about what you do and you put in a lot of energy, almost anything is possible.

Like you can't make the company successful if it, if it doesn't work, but you sure can stand out in an industry.

And where does, to loop this back, where does money now kind of come back into this conversation of, I can even just tell by the way you're answering these questions that there was clearly an excitement joining this type of spirit, right?

And joining this entrepreneurial group that was building something that you were interested in.

But at the same time, you're now living in San Francisco on first one income and now hopefully more.

But how did that fit in with the world of new and young companies?

Were you just getting a lot of stock options or were you actually getting enough to live in the Bay Area and not feel terrified that at any moment your passion is not going to fund the plumbing and the heat and the rent?

Yeah, I think I was making enough between my wife and I that we weren't worried about paying the bills.

None of the companies at this point in my life had been successful, so the stock options weren't worth anything.

Honestly, I think a reflection that I haven't really thought about until this moment is for a few years,

money wasn't a thing.

I wasn't thinking about building wealth.

I wasn't thinking about saving.

In the old world, I was, how do I make enough money so I never have to do this terrible job?

In the new world, I just loved what I was doing.

Like I didn't care.

I wanted to get paid as much as I could, but if it was less than I wanted, I I took the job because I thought I could accelerate my learning by joining a small company and figuring it out.

And if it was successful, you know, sure, I knew that there was upside in having equity, but it almost doesn't matter how much you're making as long as you can pay the bills and save a little if you love what you're doing.

But then the flip thing happened, which was none of the companies were working.

You know, it was a series of, well, I love this industry, but I keep joining these startups and the startups fail.

And we ended up working at Google for a bit.

And Google felt a bit to me more like the old version of companies where it was like you're just building the vision of a person and no one, you know, you don't get a lot of opinions.

I tried a hand at venture capital and I, I don't know if it was imposter syndrome, but I just felt like, well, I'd never actually been successful building a company.

How could I be an investor helping other people build companies?

What was the first one that you worked on where you said this is actually, this has got some traction?

It's going to work.

Obviously, we know what the story of Google, but that didn't feel like the corporate grind.

Like, was there any happy medium where there was something that ended up working out, but that didn't inevitably have to go down some road of, you know, obviously I hyperbolize a little bit, but soul-sucking corporate work, you know, that could be successful and still carry on this fun entrepreneurial.

We don't have to talk to our employees about raises because they don't care and they just love the work.

I think I worked at two startups and then Google, and then I started a company.

And all three of the startups felt like such a fun venture, but none of them worked out.

So I never had the experience of this thing's going to work forever.

I could do this forever.

It felt like, well, I could shuffle between companies that don't work.

But it kind of now I'm starting to get a little bit older in my career.

And I went to Google.

I was like, wow, you know, you get paid well at Google, but I didn't love the work.

Going back to the startups, like you weren't getting paid well enough, at least back then, that it felt like it was the best place to be for a long-term family, at least in my level.

And then I started a company.

I was like, well, this is perfect.

I can control it all.

But then the company also didn't work.

And then when that company didn't work, we found a home for some of the team at Wealthfront.

And this was a late enough stage company that it felt like the company was working, but it valued creativity and innovation.

And the role I came in at was senior enough that I could own those projects.

And I remember telling everyone, they were like, oh, how long do you have to stay?

Because we kind of marketed it as an acquisition, but in all reality, no one made any money.

I definitely got some Wealth Front shares that I hope will be valuable someday, but it's not like they deposited a bunch of money in my bank account, I didn't get a signing bonus.

So, people would say, How long do you have to stay?

And my answer was, Honestly, I could see working here for the next 50 years.

It felt like I could just do this forever.

Well, so now the obvious, why did you leave?

So, while at Wealth Front, I was having a good time,

and I don't know

what made me start a podcast.

I just, I wanted to for reasons that I can't quite put my finger on.

I asked Wealthfront, hey, this could be a really good marketing channel for you.

Do you guys want to own this podcast?

And they said, no, we don't want to own it.

Wow, missed opportunity.

And only

after doing that enough did I realize it could actually be a job.

And so I just, I felt like I had to take that leap.

I went and decided I think it's at the point where the salary of the job and the salary of the podcast were similar.

And I just felt like I had to see it through.

And you reflect a little bit here on the fact that your podcast became, for all intents and purposes, sustainable financially, but also potentially successful when others might not be.

And all we need to do is look at the numbers and realize that, correct, the majority of the 4 million live podcasts today are not lucrative enough to allow people to pivot, especially with a child, especially Bay Area, et cetera, to make it full-time.

If you feel comfortable answering this, obviously, can you reflect on some of the things that you believe you bring to this space or the content brings to this space that answers necessary questions for people that makes it successful?

Like, why do people want to tune into your show more than someone else's and listen to what you have to say more than somebody else?

I'm happy trying to answer this question.

I have no concerns answering it.

I don't know if I know the answer.

My hypothesis when I started the show was

there are a lot of people out there that like to live an optimized life.

They want to find the best deals.

They want to travel for free.

They want to sleep better, eat better.

And in order to get that information, it was very siloed at the time.

So if you wanted to tackle frequent flyer miles and credit card points, there were podcasts for it, there were blogs for it, but you had to commit really deeply to that space.

Personally, I didn't want to necessarily go that deep in all those areas, and I kind of valued the Pareto principle of the 80-20.

And so I thought, what if I made a show where I could go spend a week going deep on sleep and find an expert and do some research, produce an episode, but this wasn't a sleep podcast?

And I would say the core tenet of it is spending less and saving more when it comes to travel points, miles, investing, and personal finance.

But I still get the chance to talk about health, talk about about sleep, gut health.

Like I get the ability to go into these areas that it turns out the average, maybe slightly older millennial who has a family or doesn't and is thinking, I've saved some money, I want to do better, but I don't necessarily want to go down every rabbit hole.

But I sure would love if someone who loves to do research could go down that rabbit hole and share the 80-20 of what they learned.

And so that ended up being the show.

Yeah, because going through the content, obviously, I think you're obviously speaking pure truth, which is you hit on so many topics.

And rightfully so, the podcast is called All the Hacks.

I'm wondering, are there any specific ones that you have hit on in, let's just kind of limit it to the last year that have really deeply resonated with listeners, where you get some feedback where you go, oh my gosh.

I just hit a potential pain point or something that people do need to learn more about or that they're really struggling with right now.

You know, obviously you bring up insurance and part of me, the second I even hear that word, I go, oh my gosh,

not only am I stressed about that daily and think through all the different types of insurance, but I know many of my listeners are, but are there any specific topics that you say like, this is one that resonates right now?

It's interesting.

I would say every episode I do, I probably get three to five people that email me and they're like, I needed this one.

Sometimes that's an episode that is not the most popular, but it seems like every single one has that answer.

And we did this survey once about a year and a a half ago where I said, you know, what was one of the most memorable episodes that was the most meaningful to you?

And at the time, I think we'd done 150 episodes and we got about a thousand responses.

But it was like 130 of 150 episodes were one person's favorite.

Wow.

Someone emailed me the other day.

I did an episode and we talked about negotiation.

And they said, I was in the middle of a really big business negotiation.

I didn't feel great about it.

I used some of these tactics.

Those tactics made me half a million dollars.

That negotiation episode, it didn't perform as well as some of the others.

But for one person, it's really, really meaningful.

And so that keeps me going on all the topics.

Every now and then you have someone who says something kind of controversial or kind of wildly mindset changing.

We've both done an episode with Bill Perkins, and I think the Die with Zero philosophy really made me think differently about how I'm saving.

And your episode on the 4% rule made me push back on all my kind of inner frugality and financial independence roots.

Why do you think I made that one?

I made that one so I'd challenge myself on all that, my frugality.

I did do an episode earlier this year that was, I reflected on about 200 something episodes.

I just tried to pull out my top 50 takeaways.

And so that would be a good place to start, but I don't have a perfect answer.

That's a great answer.

And I know that one of the ways that I always learn myself, and this is a very selfish component of doing a podcast, is I learn through teaching others and I learn through talking through ideas, right?

One of my favorite old Oscar Wilde quotes is, and I'm paraphrasing here, but it's something along the lines of, until I have contradicted my own thoughts three times, I have not thought deeply enough about a topic.

So are there any topics that have evolved for you?

One that you reference is obviously Bill Perkins and kind of the art of living more in the moment potentially.

But are there any other topics that have evolved for you over the years and that you now process differently than you might have a year or five years ago?

First off, while I love that quote, I will advise people that it is not always the best for a healthy relationship with a partner because my wife will often say something and I'll be like, well, let's challenge this.

Let's really make sure this is right.

And I'll challenge her completely from one side.

And then she'll be like, I totally see you.

Let's do it that way.

And then I flip sides and I'm like, no, no, no, that was a terrible idea.

And it leads to a lot of annoying arguments.

Given that you just mentioned that a lot of your audience thinks about health insurance and how it makes sense, I think I'd always thought that the best health insurance was the premium plan that covered everything.

And if someone had asked me for advice during open enrollment, and I guess open enrollment at a company is different where you're maybe not footing the entire bill, but I'd always thought that that was the smart move.

And maybe if you're not going to use a lot of insurance in the year, which obviously we never know what's going to And then I ran the numbers.

And this is speaking mostly to the policies available on the exchanges in California.

But it turns out that the annual cost of the premiums for a family of four, at least for us, looking at the highest best plan and the lowest cheapest plan are about $2,000 extra a month.

So you'd be spending $24,000 a year more to have the best plan than the worst plan.

Now, the worst plan has an out-of-pocket out-of-pocket maximum that was like $16,000.

So if you get the worst plan, the maximum in the worst, worst case scenario, you'd pay is less than what you would pay for the best plan without ever using it.

The only reason that that plan is not good is it's really about your psychology.

And so the reason I bring this example up is because we did this experiment this year and we went on the high deductible PPO plan that had you know high deductibles, high out of pocket maximums, but was the lowest monthly cost.

And we did it as an experiment because we knew the hardest thing was going to be, I think we had to spend, I don't remember how many thousands of dollars before any insurance kicked in, which meant that if our daughter was coughing and we thought, hmm, do we take her to the doctor?

It's going to cost $800.

And anyone listening with kids knows that like nine out of 10 times that doctor's visit is like, nope, all good.

But we knew going into it that every single month we were saving

some astronomical amount of money.

So if we went to the doctor three times in a month, we were still coming out ahead, but it was still painful in the moment.

The reason I bring this up is it really pushes back against this idea of I really like prepaying for things because it takes away the psychological pressure of, do I go to the doctor's visit now?

And I'll give a quick anecdote.

Back when I lived in New York, I would always prepay for the monthly subway pass because I was so frugal that I was like, I'd rather walk than pay $2 to take this subway ride, even if it was like a 45-minute walk.

I was like, the $2 just seems crazy when I could walk.

And then it went to $2.25.

It's like, oh, I'm never going to take a subway, you know.

But if I just paid the $70 one time, then every time I got on the subway, I didn't have to think about it.

Like, I knew that paying in advance would take away all this, you know, analysis paralysis, which most people listening are like, for $2, you're crazy.

Yes,

hopefully, some people can sympathize.

But somehow

it worked.

I don't know what we did differently, but we just went to the doctor.

We were like, and maybe the fact that it's your child and they're sick just gets over that.

It helped that early on in the year, my daughter fractured her leg and basically blew through a lot of that deductible quickly.

You know, genuinely, I wish she didn't do that, but it's sure made like going to the doctor now,

I already hit the out-of-pocket maximum.

So like, you know, do I want to go to the ER?

Not going to cost me anything.

Yeah.

No, you're speaking my language with the prepayment.

That is probably the number one thing that both I've heard from you, but also have employed in my own practice.

And same thing, it's probably the only way that I actually allow myself to spend what I'd like to spend is by prepaying.

And then everything somehow seems way more affordable if I just rip the band-aid once.

Right.

But one thing you just said in that answer about insurance is that a lot of people are driven towards kind of getting the lower deductible plans and the premium plans because we never know.

And I'm really intrigued about that overarching psychological wiring and how it

informs so much of what we do on a daily basis, whether it's investing, accumulating, insurance, premiums, et cetera.

How do you feel like that applies to our desire for more money, just to keep accumulating money?

Like this idea of we never know.

How does that relate?

I feel like I'm going to regurgitate things that you've told me, but

when you don't know what the money's for, you know, you need more.

I had a conversation with a friend yesterday.

He's like, I don't know why my target net worth number is this number.

I just feel like it is.

And I asked him, I was like, have you done the exercise of how much money you actually need to live the life you want?

And he's like, no.

And I'm like, oh, okay.

Well, guess what?

When you do that, you'll probably realize that that number is way too much.

You mentioned when you were on my show that, you know, you experimented once flying business class and it wasn't, you know, all it was cracked up to be.

Big letdown.

Big letdown.

Yeah,

you had a poor experience.

I will push back and say, especially if you can figure out how to do business class at a free or very much lower cost strategy, flying internationally in a bed instead of a chair, right?

Like when you're doing that for the same cost as economy with points, I don't know.

It's hard to go back.

But

we always think we need all these things or we might one day want them.

The number of people I know, they're like, well, I need more money because one day, what if I want to fly private?

It's like, if you just take that off the table, that's like $10 million you don't need, you know, like, and it's really stretching.

And so, I think I've gone through the exercise of what does my life cost?

What do I think it would cost in an ideal version?

And what do I think it will cost once I don't have kids and once we've paid off our mortgage?

And what does that need?

That's a lot more in reach than the number that I would want if you looked at my net worth and said, what do I want to get to?

Because it's probably 2x what I have, right?

Like intrinsically, I have this desire for more.

And it's hard, right?

Like I know with the income we have today, we're kind of in a place where we're okay.

And then I find myself making decisions about the business, about our life that are completely irrational.

Something I've learned about myself.

It's way easier for me to think about spending tens of thousands of dollars to buy all the furniture in the house than it is for me to think about spending $1,500 on a bed.

I don't know why, but in this case for my wife, it's the opposite.

So my wife and I were talking about getting some new furniture because we honestly, I don't think we've ever bought nice furniture.

We've graduated from IKEA.

We're in the same boat on that one.

I think we've graduated from IKEA, but we've, you know, barely.

And so I was like, you know what?

Why don't we just come up with a number that it costs to buy all the furniture?

And I'm happy to give you opinions on individual pieces.

Just don't tell me how much they cost.

Like, I don't even want to know.

Like, I've understood myself that I'm almost, like we talked about earlier, pre-buying the furniture by just saying, let's commit to this one total amount.

And then I don't have to think about it on an item by item basis.

And so I don't need to make all the individual decisions on prices because it'll drive me nuts.

And really, it'll drive her nuts when I talk about it.

Well, I want to, I want to shift just in kind of the closing minutes here.

I want to shift a little bit because, again, I mean, I could, I could talk to you for hours and pick your brain about the hacks, but I'm going to go into something that I did a couple of weeks back with a guest, Tess Waresmith.

We did a lightning round, and I would love to get just your quick take on a couple hot topics.

Don't think about them, we don't need to elaborate on them, but just a yes or no, what would you do, or what was the experience like?

Because again, I know how much you have to offer and how much you've thought through all of this.

So, to start it off, best purchase under a hundred bucks you've made recently and why

an ultrasonic cleaner for my final trays for my Invisalign that I wear every night.

And it's like just the hassle of throwing it in a cup with a little cleaning thing or brushing it with a brush.

Just so great.

I bought one for my wife and she loved it.

And then I bought one for myself.

I didn't buy the fancy brand dental pot.

I bought the Amazon one that was 40 bucks, but awesome purchase.

Most overrated piece of financial advice you've ever heard.

I think the most overrated financial advice is all the tax advice that's floating around TikTok and Instagram right now.

Employ your kids and, you know, go buy a G-Wagon and do all these things.

And if you own a small business, there are a lot of things that in the right circumstance are good business deductions.

And in every way, I see them being talked about online, they are not.

And I think the, I am one who absolutely loves.

to minimize my taxes, right?

Every year, at the end of the year, I do an episode on all the things to try to minimize taxes, but not at the expense of committing fraud.

Like, not at the expense of breaking the law or breaking the tax code.

See, and that's why you need to get into social media so you can be a voice of reason amongst all of these 20-year-olds who don't know what taxes are yet.

One money app you can't live without.

For me,

oh, it's a tie between Coubera and Copilot.

What do they do?

So, Coubera, I think, is the best net worth tracking, portfolio tracking app.

and co-pilot if you're on iOS is for me the best designed spending tracking biggest waste of money you see people in their 40s and 50s making now and to be fair I don't know if I have answers to most of these questions

I just came out and go these are good these are fun but if I were put on the spot I don't know I don't know if this is a fair answer, but I have both friends and people I see online that are spending money on things that I'm not necessarily against.

I'm just wondering whether they've taken the time to think about the impact of those purchases.

I don't care if you want to buy $800 shoes, but when you talk to me about the apartment you want to rent being like $300 a month too expensive and you really wish you could afford it for your family, and you're buying the $800 shoes, I just wonder whether you just haven't taken the time to think about your priorities.

And so I don't care if you want to spend money on whatever it is that you love and what brings you joy, but I often feel like people are doing that without taking the time to think about what are the things that actually bring them joy.

And so the people who are buying things that they think will bring them joy without taking the time to think about it, I think are the most overrated or waste of money.

Then this is the perfect last one for you.

What's your guilty pleasure spend that you'll never cut no matter how much the screaming heads tell you not to and that it's a waste of money?

It's probably credit card annual fees.

I think right now, between my wife and I, we probably have, I had to guess like $10,000 of credit card annual fees.

And everyone I know is like, this is crazy.

And I play the game and I enjoy the game and I don't recommend this to everyone, but I know so many people who are, who hate credit card annual fees.

And I think, for the most part,

If you play the game right, you can make up for almost all of them.

There are a few where I'm like, no, that fee is not worth it.

But for the most part, I will gladly pay an $800, you know, $900 annual fee.

I don't know if there's a $900 one yet.

I think Amex is going to launch one before the end of the year.

But it keeps creeping up.

I'll pay whatever the annual fee is if I've taken the time to know that I can get the value out of it.

But on the flip side, I know so many people who pay the $695 annual fee for an Amex Platinum card and don't use any of the benefits.

And that card, by the way, is not a card for spending.

Like the Amex Platinum card is one of the worst spending cards out there, but a great benefits card.

My wife and I each have between the personal and the business, I think we have five Amex platinum cards.

And that's a story for another day, but we don't put money on them because it's a terrible way to earn points and get rewards.

But the benefits of having them, the signup bonus from opening them were worth getting them.

Well, now you've obviously prompted me to want to ask about 10 follow-up questions, but I'm going to save them because I want you back on the show very soon where we're going to unpack $10,000 worth of credit card fees and what you get for $10,000.

That's awesome.

I love it.

Please do tell me though, in the meantime, if people can't wait to hear you back on this show, obviously you do tons of incredible work.

Where can people kind of find more about how you think and some of the shows you're currently working on?

Yep.

If you just search for all the hacks on whatever podcast, video, player you're on right now, you'll find our show.

We release an episode every wednesday that's a deep dive into something and i think if you want a good place to start go back to june and look for the episode on the top 50 lessons or just scroll till you see something that's a challenge in your life if you need a mini retirement if you're trying to think about how to save some money on hotel stays if you're trying to think about retirement you know, accounts, there's an episode for almost any area of your life you want to optimize.

And so find one that speaks to you and send me a note what you think.

There's a form on the website.

I read every email that comes in.

And I can emphasize that no matter who you are and what you're looking for, I promise Chris has the answer somewhere on one of these episodes.

So definitely worth the time.

Chris, thanks so much for being on the show and I'm looking forward to connecting with you soon.

Yeah, thanks for having me.

Thanks for tuning in to your money guide on the side.

If you enjoyed today's episode, be sure to visit my website at tylergardner.com for even more helpful resources and insights.

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Until next time, I'm Tyler Gardner, your money guide on the side, and I truly hope this episode got you one step closer to where you need to be.