In this episode Paul discusses the tedious process of cleaning up his late father's yahoo mail. Rich and Paul talk about the creepy and private side of tech, which is the intense marketing behind newsletters that are just trying to get money out of subscribers. This podcast is sponsored by Aboard.

richard, how you doing I'm Yeah, me too.

Me too.

So look, I, I have a topic for us today, which is that my, uh, you, we talked

about it before my, my father passed away almost a couple months ago now.

Right.

And, uh, after you die, you leave a lot behind you've

bank accounts and a dresser and

Email boxes, email inboxes, all kinds of

Even when, I mean, his life was very constrained at the end.

He was in assisted living.

We'd taken over his finances for years and so on.

Even so, there's a lot.

He left a lot of manuscripts, which I scanned and put

online and so on and so forth.

So I'm down to one last task.

In the sort of saying goodbye, grieving, cleaning it all up, mess

files,

And, and if I may ask, you have a brother,

he has other family members.

Why did you get tasked

I, I got all the digital

Okay.

so that was

my wife took over the money.

My brother took all the physical stuff and some of the money stuff.

And so sort of like my brother was down there near him,

so he took on more of that.

Like

physical care,

Got it.

Most families don't work this stuff out when the person is still alive.

Yeah.

we had a, we did a good job, and this is, this comes down to my wife actually,

and I, I'll just say this as like complete advice for everyone listening.

Get one password and get all of their passwords into one password Get them on

your account, teach them how to use it.

Know they don't want to do it, they write it in a little book, et cetera, et cetera.

This, this podcast is not sponsored by one password.

Yeah.

I gotta tell you that it ma, it makes a world of difference, of

course, because what happens is you gotta get into the Gmail account

to get into the bank account, to get into the blah, to get into the

You don't wanna get in touch with Microsoft with the

No, you don't.

You really don't.

No.

It's just, so, anyway, uh, so.

Uh, the, the task I'm doing now, pretty much everything's done except for kind

of the long it actually takes, it's gonna take like a year to get all the

bank stuff settled cuz it goes through the courts and so on and so fine.

No worries.

So there's that, that's gonna linger.

But the last thing is I, I wanted to just like download all of his email and just

kind of archive it in a zip file in case we ever needed anything but not so Gmail.

No problem.

Here it is.

Got it.

Okay.

Google takeout.

All done.

Yahoo Mail, which was his dominant source of email.

boy.

Yeah.

Not so easy, right?

Yeah.

So this is

not about Yahoo Mail.

I want to talk about what I learned.

Going to clean up that account.

So you're seeing the emails, just to clarify forever, you're

not just getting a bulk zip file,

No, you can't.

You can, you can with Google.

So

do.

Google takeout

Got it all.

It's, it's downloaded.

It's in a folder and gonna zip it up and it'll, it'll, it'll sit on

a hard drive and then eventually, um, I will die and no one will care.

Like that's, that's gonna be around for 50 years and no one will look at it.

Yeah.

I have to ask why bother?

Uh, just sort of crossing everything off the list.

Okay, so it wasn't a wish that was

No.

What was the, the wish was that I would archive his

manuscripts and put them online.

I did that.

You can go to archive.org/details/frank b for, and there's 7,000 plus manuscripts.

Okay.

Good.

Good.

he was a writer.

That was his, that was his big request of me.

That

that was a request.

He asked me many times to

But he didn't care about spam emails?

Never talked about it.

Yeah, never talked about, but I'm just sort of like, you know, it's just

like, here's the record of the guy.

It feels wrong to just, I could just let the account sit there, but that's

This is a little bit of the librarian in you.

I just wanna get it done.

Okay.

I just wanna get it done.

And this is, and so like I said, Gmail and I sort of like, I had this list

in my head of like, let's archive his emails is clean up his footprint, cancel

the eBay account, like all that stuff.

Just like cut off the, the ways that people could exploit his identity

or you know, cuz you know what they do the minute you, you die and they

published your security, your social security number kind of gets retired.

yeah, there's like lists of dead people's social security numbers, but,

but identity theft like happens right?

The minute that obituary hits the website from the funeral

people try to hijack

Yeah.

Yeah.

So you're actually like, bank accounts get compromised and so what happens

is now, so it's doubly hard to unlock people's, like bank accounts after

they die because everything's fraud.

Like everything I

I see,

you know, like some, someone is so, and people were

trying to get in, they, they.

Didn't, you know, just like this, this just happens, like this is just a given.

Yeah.

So, so I just kind of wanna diminish the, the digital footprint, right.

So anyway, um, my, uh, so Yahoo mail, older product, not, not the most robust of

it's still around.

My mom still uses

Oh yeah.

A lot of moms, A lot of dads.

And, uh, so I get in there and I, you know, I, I, I use imap,

the classic thing to download it.

And it turns out you can only have.

So I'm like, I'll go get all that mail.

I'll be done, I'll zip it up, all done, say goodbye to dad on order life.

But no, you can only get, um, 10,000 messages at a time in a folder.

Okay.

That's like three weeks of messages

of, of especially if you're 90 and like to subscribe to newsletters.

Oh boy.

And so, uh, this has been a multi-week process, but

it's not like an active process.

What happens is I go in.

You batch a bunch,

you.

Literally, you scroll and it dynamically reloads, and I get like a couple thousand

messages listed in the window, and then you hit the button that says Select all.

Mm-hmm.

And then you wait like 45 seconds.

I usually go do something else.

Oh,

I come back.

Then you hit delete.

This

this is rough.

not great.

There are like 240,000 messages.

So I've had to do this a lot.

Takes a while.

So I was like, this is a grizzly task, and, and sort of why bother?

Right?

And, and then I was like, well, let's see what, you know, just

this is way my brain works.

Let's see what we can learn here.

And so I learned a lot.

I, I saw, you know, I didn't know great secrets fall out of my dad.

Right?

Like I knew him pretty well that way.

And so, like a lot of, you know, basketball emails with his buddy

mm-hmm.

And, you know, pictures that I sent him of the kids and

he would reply and he'd be like, looking good, you know, the.

So, so some sweetness there and put those into folders that we're saving

any of the photos, anything like that.

Okay.

And, uh, but then the newsletters and I started to actually see our entire

industry in a slightly different way as a result of this process.

Explain.

So I look at the newsletters and it's.

What you would expect for a left-leaning, 90 year old New

Haven guy who's now in Florida.

It is democratic, you know.

Debbie

Waserman Schultz needs you, Frank.

Ah, okay.

Okay.

A lot of like Joe Biden sending emails in 2015.

Like just one question,

Yeah, yeah, yeah.

A lot of direct first name basis

need that $20, you know, we're almost there.

Yeah.

And a lot of, and then those tend to devolve a lot of them

into like, It's intolerable.

That'll just be the subject

Yeah,

Or this can't keep happening.

And then, um, so that's the, that's the politics part.

And then there's the, uh, newsletters, the New York Times, the New Yorker,

Harper's Magazine, where I used to work, and so on and so forth.

Okay.

Then there's the Amazon stuff,

which is endless.

Legion.

Yeah.

And then there's like, Pills and medicine and health tips, and Dr.

Merkins, this and that and the other.

Yeah.

Um, and, and it's an absolute ti wave.

It's, it's, you know, maybe 150 a day.

Wow.

And I can see the read and unread.

He's reading one or two.

You would skim 'em really up until into his nineties.

Like he, he got his news that

it was email.

Someone emailed me.

And so I had this funny thought and it, it's really something

that is, I'm starting to process, which is there are two things going on.

One is,

Um, you know, I saw the messages from like Harper's Magazine and

I used to work there, right?

So I'm like, oh, that's cool.

You know, I mean, dad and I had that in common.

We talked

a connection.

It's a connection.

And, you know, long after I, I left way 10, 15 years ago at this point.

And, um, uh, so, okay, there we go.

And then I'm like, I'm the New Yorker.

Well, you know, I, I wrote for the New Yorker website and I know

people there, and then I'm like, oh, these Democratic emails.

And I'm like, yeah.

You know, the, we used to work a little bit with some of the people who worked

with the Obama Foundation and they used to use these systems for like mailing all

these people and then the New York Times, like we know them, we know their tech.

I'm, I'm looking at you as I'm saying this cuz you and I over our current,

there was a bank in there and that bank.

Actually approached us about buying something that we owned once, like yeah,

you know, that was his bank and it, it was this weird moment where I realized that

like by being in New York City and working in tech, We touched all these systems.

You know, we worked, Postlight had MailChimp as a client.

MailChimp, right.

powering all of that.

A lot of it,

So like it's, it was really weird to be on the, and

I get a lot of newsletters and unlike everybody else, right.

It was really weird to just see it in someone else's eyes and

Yeah.

The downstream of all that signal that we generate.

It really kind of looks like one thing.

And I don't think it does to you and me, I think we're like, oh, that's this.

And there's, you know, here's the, here's the democratic fundraising app, and we

kind of know the machines behind it.

Yeah.

And it's not like everybody sits down and works together, but you

might run into each other at a party.

Yeah.

Yeah.

But I think when I look at my dad's inbox, it was this monolithic fire

hose of people tapping on the shoulder and saying, I wanna tell you something.

And also I need 20 bucks.

Doesn't matter what, and it could be the New Yorker magazine cuz

they want that subscription and so

Sure, sure.

And I noticed, not that it got real profound, he wasn't like a

Fox News guy, but there was definitely like a kind of conspiratorial bent

as he got old.

Not like, not like intense, just sort of like, ah, those bastards.

Yeah.

Real normal on an older guy.

Sure.

I'm sure it'll happen to you and me.

Yeah.

But man, when I looked at that inbox, I'm like, yeah, of course.

That's how it would look like to me.

It looks like, it looks like that.

Yeah.

It looks like God these's bastard, everybody.

Them and them and them, and everybody wants something and

they're telling me about the other people who want to kill us all.

And you know, it's just like, it's this real just fire hose.

I, I, you know, it's interesting, I don't think anyone,

there's been a lot of attention given to, um, sort of public side of tech.

The, the, the toxicity of social media, the misinformation, all of that stuff,

which is frankly out in the open,

Um, the dynamics of creating critical mass around sentiment.

Turns into mob very often.

Mobs, you know, the thing I love to mention is, you know, oftentimes the

traffic is not because of the accident, just people watching the accident.

Right?

That's, that's, to me, the internet

like mm-hmm.

Mm-hmm.

and what you're talking about is something very different

and it's actually almost equally creepy, except it's not out in

the open, it's not adversarial.

It's just a guy in Florida getting pummeled.

Constantly because everyone is looking for that last bit.

Right?

That's right.

And, and, it's a strain.

Here's what people don't realize, and if anybody's listening outside of

the United States, poor people in the United States who are elderly oftentimes

have hundreds of thousands of dollars.

Middle class people, lower middle class people that have been kind

of pecking away their whole life.

Mm-hmm.

Have some money.

if they ever owned a home.

especially if they ever owned a home, and believe me, they know

and they profile and then what they hope is, uh, they can, uh, just get a little

bit, everyone's just trying to get a little bit, and what you end up with is

this channel that was a really designed for your kids' pictures, getting to him

Mm-hmm.

fully appropriated by a system.

That's right.

Right.

And that's a wild thing.

And, and you know,

and, and let's be clear, like he, Yahoo has a very easy interface

for unsubscribing, for newsletters.

One of the best I've seen.

It's like unsubscribe for newsletters and it shows you all

the newsletters with their icons.

Yeah.

And you one click.

And I, I un that was great.

It was excellent.

I unsubscribe from like a hundred newsletters just to stop the flow and,

why do you think he didn't, if you had to guess?

Obviously he's not here to explain himself,

but it's the newspaper he was when I grew up, he read the paper

every day and he would get the Sunday New York Times at the Wawa at the store

and he would read the Sunday New York Times.

Like that's, it was, you fill your brain, right?

You, you keep going and, and.

And, and the thing is, is like these are all, there's no scandal to this.

There were like,

no, it's junk mail,

but it's, but it's junk mail from like the Times in the New Yorker

and it's all, it's like, you know, the Borow witch report was in there.

That was, that was the most upsetting

Did

you, did you ever get mail that, um, is.

Really trying to trick you into opening it.

It says like open immediately

Yeah.

There's, there's, you've won and then there's like, these are your blood test

Yeah.

there's, they're trying to get you to just take that next step and then

sometimes when you open it, it's like handwritten ink that's dried, but

clearly it's a little too consistent.

So there's like startup, I know there's companies that, like they

have machines that write handwriting.

man.

When I used to work in magazines and that's how you market ma, like

the letter from the editor will often be that fake handwriting

Totally, totally.

And and the truth is, guess what?

That stuff, it's actually pricey.

There's a math

Yeah.

No, no.

Costs

you know, we're gonna spend $50 on this individual

in this, in this calendar year, and there's like a 3% chance.

But when they tap, when they tap in, we'll make thousands of dollars.

So we're

you don't, if you don't live in this world, right.

There's cost for acquisition, there's arpu, which is average revenue per user.

Like there's all these terms and, and concepts that vary

from industry to industry.

Exactly.

But I think what happens is the cost of uh, just pummeling you in your

email inbox is just way, way lower.

And so they're like, you know what?

Just carpet bomb, that shit

Go to town.

yeah.

I mean the state of Florida, the spam, the collective spam

inbox of the state of Florida.

it, it's, I just have seen it, man.

And it's, you know, Chan Channel six Orlando News.

Yeah.

Yeah.

Is it bad?

It's neither bad nor good.

It is fascinating.

So first of all, I, my father was, um, up until really

towards the end pretty with it.

Yeah.

And so he was opted in.

He was a technical person.

He used a laptop, like he had control

Did he hate it?

He didn't hate

Didn't hate it.

this is, I, I think I, I can give you a second data point.

My mom doesn't hate it either.

My mom, when I try to quote unquote clean up her machine, she tells me to stop.

No, that's on my free emails.

She's

my father, spent more time trying to get free

access to the New York Times.

It was like the number one goal in his life, and I wanted

to buy him a subscription.

Then I realized I would've taken away everything meaningful.

You know what?

It's motion and it's activity.

Yes.

And it's communication.

Even though it's a machine that's doing

well, there's also, there's no, hi,

Frank, get in touch.

Frank.

Frank, we need you.

Right?

Like when you see your first name in an email, right?

That's a I'm, I'm younger.

You're younger, you know, for years.

It's like, wow, look how annoying this is.

Look at this weird kind of overture they made on LinkedIn with me.

But when you're older, doesn't, nobody's calling you.

No.

And you know what the cl the idea of the cleaned up inbox has no meaning to him.

Right.

Like, that wasn't what he was going for.

It was just a s Yeah.

Well he's never scrolling back.

He's never scrolling back.

Exactly.

Exactly.

My mom, the idea of unread, like inbox zero, it doesn't

make any sense to her at all.

No.

Why?

She just, she just sees it as Tuesday's new stuff and she might get through it

or she might not, it doesn't matter.

To her

Gmail earlier and stuck with it.

Yeah.

I wouldn't have this problem cause I would just be able to get all the

email and I would never think about it

But I, I, you know, this sort of pushed me into think about it.

The other thing that made me realize too though is like, The effect is the

same as like the Facebook ad campaign and social like it's, you're getting all

this like huge fire hose of information.

Yeah, but it's disaggregated.

And it made me wonder, you know, we go, when we criticize and think

about tech, we go for the big targets because they have a lot of money.

There's people like Mark Zuckerberg in charge, and Cheryl Sandberg formerly and.

Uh, they're not necessarily acting in our best interests and they keep

telling us they are, and it's weird and it's bad, and we kind of go after,

and it's, and newspapers like to write about it, et cetera, et cetera.

Yep.

But the sum effect of everybody kind of having their saying, could

you get your wallet out just for a minute, no matter who it is, across

hundreds of different organizations.

Isn't that different, right?

It, it's sort of like, it isn't, we, we kind of revert to this form

as a society when we have cheap communication methods and older people

who still have money in the bank.

Yeah.

It isn't that different.

I, I think what is different though is that, um, unlike the

line between earnest, like genuine communication and marketing on.

Social media is much trickier to, to, to pin down.

Um,

it's true cuz all your friends are right there.

Yeah.

I think my mom knows that people are shilling stuff in her inbox

that she knows, like, and she's okay with it because she likes

to get a pile of mail every

it's like getting the penny saver in the mail,

Yeah.

She doesn't mind it.

I think online, you know, I think where it starts to get blurry is when

people have hidden agendas and they're either marketing something or they're

trying to trick you or frankly they're trying to misinformed you and you

can't tell the difference anymore.

I think the inbox is a funny thing.

The inbox is you saying, please read me, I am in your mailbox if you like.

Well, I think you and I just have utterly different

relationships cuz we're still working.

right.

That's right.

And it, it's so,

yeah, my mom doesn't get my mom as soon as she figured out.

Like chat and messaging never communicates with us through email.

No, that's right.

It's all one big

it's for

square, like madness,

it's for newsletters and it's for, um, sales and circulars.

That's right.

I'm gonna, oh wow.

You know Tiger Direct.

That's right.

Tiger Direct.

Love my

She doesn't need Facebook's notifications.

She goes to Facebook.

She's already in there, so she doesn't see it that way.

And she sees it as a place that tries to sell her stuff.

Now I will say there she, my mom, because she's.

Kind of generous with her information.

She's, they've attempted to scam her many times.

Like, they'll call her and say, listen, she's gotten letters of like, uh, debt

collectors of stuff that she didn't know.

Like it looked totally authentic.

This is the worst part when they're like, my dad especially has like

real sharp and then money was where he got real starting to, we took all of his

finances away from him at the end cuz he was so every time you get a bill panic.

Yeah.

My mom doesn't need to be in debt.

She has debt on like 20% credit cards.

Yeah.

Today.

And by the way, I was like, let's pay these

off and clip, clip the card.

They're big, colorful little little jewels in her wallet.

She doesn't wanna get rid of 'em.

She likes 'em.

She takes her friends out to lunch.

I'm like, mom, take her out to lunch.

But just pay with cash or a debit card?

No, I, I have the Capital One.

Golden Jubilee

Oh

card.

You know?

You know it.

tell you something.

We're about to launch this product aboard the sponsor of this podcast.

Speaking of like paid promotion sponsor

sponsor of the podcast.

This, everybody knows this is a marketing product

as well as, no, not really.

This is a, this is a sponsored podcast.

There is by a, sponsored by a company we co-founded.

So

It's on a board.com.

We are gonna start waving in tons and tons of people,

great time to sign up.

But, oh, I will say,

We're just getting started and we don't have this huge email strategy that

we were gonna pursue with the board.

Yeah.

But it did make me think it was just like, you know how you're right.

My father liked his emails.

Yeah, right.

But there wasn't a lot of utility and there was a lot of noise.

A lot of

And so I'm just like, I don't know how you solve this, but I'm like,

how do you make the one that he would want to open that would have the information

and the, and the bargains and the deals

it gets hard to find the good stuff.

Right.

Let me ask you this, we're a lot unread.

Oh, all of them.

All

like 99%.

That's what, so it was, it was

you're going back three months and they're on red.

Oh, so he's not even opening them.

no.

It's actually really easy to clean it up because all I did was I took all the red

ones, which goes to about maybe like 5%.

wow.

It's like my mom.

Yeah.

yeah, put those into a folder and now I'm just erasing the 95%

He didn't bother reading 'em anyway.

Yeah.

It doesn't matter.

There's, they're, they're

Right?

And then once that process is done, I'm down to about 19,000 messages.

I will have a reasonable intractable inbox that I can download and zip up.

So that will be the end of this process.

But yeah, no, no, no.

They are all nice and bold on the web browser screen completely untouched.

Um,

So we're gonna do that.

We're gonna, we're, we're gonna keep talking about how to create value.

One of the things about this product, and, and as you come in and

you're talking about a board.

We're talking

about a board, when you come into a board, you'll

see it's kind of for everybody.

Like, I would love for people like my dad or my mom to use it.

I,

I, mean, I, I think.

Buying gifts for people, collecting things, creating resources

is a very basic, universal

Here are the, this, a board is a good tool for sharing the,

the gifts that the kids really want.

Yeah,

The gifts,

g those two, right?

Yeah.

Um, and and so that granddad buys them something on Amazon they want.

That's right.

Or you can, you know, what does my mom do?

She's like, tell me what the kids like these days.

Right.

These books and so on.

And the kids could

We're being cryptic again Paul soon.

in.

Come in, yeah.

Oh, so soon.

We're gonna talk when a board is out there and you can go to a board.com

and not just see funny gifts, but actual product description.

Uh, we're gonna have a couple podcasts talking about it.

So if you want to get in touch, hello@ciford.com and uh,

check us out at CI ford on Twitter and uh, let's get back to it.

We got a product to lunch.

Yes, have a lovely week.