The Thing We Never Talk About

Timothy Iseler: Well, Ryan, end every
episode with a question from my guest.

Here's yours: what was the
biggest obstacle you faced

during your career transition?

Hi everyone.

Welcome to The Thing We Never
Talk About, a podcast about

personal finance for weirdos.

My name is Tim Iseler.

I'm a Certified Financial Planner™ and I
run my own independent financial advisory

business helping musicians, artists,
and other people with weird jobs make

smarter decisions with their money.

You can learn more at iselerfinancial.com.

And if you have a question about money
or personal finance, please send it to me

by visiting iselerfinancial.com/podcast

and I will answer it in a future episode.

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Today I am speaking with Ryan Isaac.

In a former life, Ryan worked in
professional baseball with both the San

Diego Padres and the Arizona Diamondbacks.

These days, Ryan works as an education
fundraiser and, after leaving the baseball

industry for several years, he has
rekindled his love of the game through

his newsletter Warning Track Power, which
you can find at warningtrackpwr.com.

I will also link to
that in the show notes.

We talk all about his journey from
writing about food and wine to

his career in baseball, to leaving
baseball, and all points in between.

So thanks for being here and I hope
you enjoyed this conversation with

education fundraiser and baseball
newsletter writer ryan Isaac.

Ryan Isaac: Hey, Tim, how are you

Timothy Iseler: I'm well.

How are you?

Ryan Isaac: doing?

Fine, thanks.

Timothy Iseler: Yeah, good to see you.

Ryan Isaac: You likewise.

Good to see you.

Thanks for, uh, thanks for
reaching out and connecting.

Timothy Iseler: Yeah, no problem.

Thanks for making the time.

What do you tell people
you do for a living?

Ryan Isaac: I am a fundraiser.

I work in fundraising, uh, for a pre
pre-K through 12th grade, so ages

three to grade 12, independent school.

That's relatively new for me though,
so there's a little hesitation

when I say that just 'cause I
don't have a lot of practice in

telling people that's what I do.

Been in this role for
about a year and a half.

Uh, and it fits well now, fits
my lifestyle and who I am today.

Uh, but it's been a long
journey to end up here.

Timothy Iseler: Yeah.

Yeah.

So I first became aware of you and your
newsletter, Warning Track Power, after I

spoke with Franz Nikolai on this podcast.

And he's a big baseball fan, and so
that's how I found out about you, and

we'll talk a lot about that today.

But before we do, can you describe
how you got to where you are

now from your previous life?

Ryan Isaac: Sure.

There are a few lives here, so,
make my way through it as quickly

and painlessly as I can here.

But I came outta school
wanting to be in journalism.

and been a writer and just enjoyed
writing in middle school, high

school, and ended up landing what
really saw the dream gig at the time.

Uh, an editorial role, editorial
assistant job at Wine Spectator

Magazine in New York City.

So I was 22 years old, working for a
Manhattan based glossy magazine and

got to eat and drink my way around
the city for most of my twenties.

That was a lot of fun.

We probably come back to that
one as we talk about, um, you

know, things we don't talk about.

But,

but I, baseball was my passion and
I played baseball in college, always

followed as a fan, and I was at that
right age of let's just oversimplify

it and call it the Moneyball era.

When suddenly someone who didn't
play the game at, at the professional

level or at the major league
level, had a chance of getting in.

Uh, and it was actually through wine
that I got my foot in the door, uh, in

baseball and left Wine Spectator to move
out to San Diego, take a leap of faith.

Uh, so move from New York City to
San Diego and put myself in the right

place to have things break my way.

Uh, I got lucky.

I, I remember sleeping in my new
apartment in Pacific Beach in San Diego.

I just signed the lease
like a week before.

Had done the best I could, saving
money to prepare for the move.

But living in New York City, working
in journalism, there wasn't a

whole lot of opportunity to save.

And I really, I, I think I was one night
away from no longer sleeping well at all.

I got a call from the person who became
my boss friend, uh, was my mentor.

And he told me that, uh, his executive
assistant had just retired pretty much

on the spot during spring training.

And she wasn't coming back and he
needed somebody at least to answer

the phones for a little while.

And it was a way to get
my foot in the door.

And honestly, it was way
better than an internship.

It was a, became a full-time job pretty
quickly and got me on the inside.

So I was in baseball for a while.

I was in in baseball for about 13 years.

And along the way, I met my wife,
got married, we had moved, we bounce,

she moved out to Arizona with me.

I ended up going from
San Diego to Arizona.

Things ended as they do sometimes
when you don't win enough games.

Uh, and things ended for us in Arizona
after the 2014 season and we moved back

to New York where my wife was from,
where she lived, where her job was based.

Then at that point I was
scouting in 2015 while my wife

was pregnant with our daughter.

And I started to reexamine the
way I was gonna go about things.

Didn't want to spend too much
time parenting by FaceTime.

And one thing led to another.

Uh, we ended up moving back to San Diego.

I had a couple jobs just trying
to get my feet on the ground.

And here we are now.

So I, I think, I think the way that
I came to connect with Franz, I've

been in journalism before, I was
a writer, I worked in baseball.

I never had wanted to marry the two.

Timothy Iseler: Uhhuh.

Ryan Isaac: No interest
in writing about baseball.

Then, then COVID happened and you know,
we, I think we all found ourselves a

little more alone, a little more isolated.

And I just got an itch to do something
creative and started writing.

Started writing about baseball
'cause I had baseball energy

that needed to go somewhere.

Timothy Iseler: Yeah . I wanna pull
at something or clarify something.

So you moved to San Diego just because
you thought it would be a good place,

not because you had job lined up.

You just thought like, this is
the place where putting myself,

where there's the opportunity.

Ryan Isaac: Um, back in
the first time when I left.

Yes, yes.

So I had made the connection with
Kevin Towers, the person who ultimately

hi, hired me, who was the general
manager of the Padres at the time.

I had made that connection, we built that
relationship, I spent some time with him,

and he knew what I was looking to do.

But no, there was no job here for me.

It just reached a critical mass
for me where it was do or die.

And I had gotten tired
of the New York City

scene, the, you know, the, the
hustle and just like the, the

daily grind, the monthly grind
to, to pay rent, to, to survive.

My, I feel like my lifestyle
frills came during work when I

got to go to nice restaurants for
lunch and drink, drink good wine,

and get exposed to those things.

But it didn't help pay rent.

And at a certain point, I, I think I was
just itching to get out of New York City.

And just had this, this fire in me
for a couple years of wanting to work

in baseball and felt like this was
the best chance I was gonna have.

So, like, what the hell?

I was 28 and had nothing
really holding me back.

So, yes,

sold some stuff, packed some stuff,
got a one-way ticket, and, uh, landed

in San Diego in early March of 2005.

Timothy Iseler: yeah.

Do you think you would have, had
the Diamondbacks continued winning,

do you think you would've stayed in
baseball or do you think there was

something else where there was another

Ryan Isaac: Well,

Timothy Iseler: it was time

Ryan Isaac: probably

Timothy Iseler: on?

Yeah,

Ryan Isaac: no, probably, and uh,
I appreciate that question 'cause

it gives me a chance to clarify
there, there are plenty of good

parents who work in baseball still.

Timothy Iseler: course,

Ryan Isaac: Um,

Timothy Iseler: I'm not

Ryan Isaac: you know, no, but I, sometimes
I feel like I'm coming off that way,

like, ah, you know, it's fine for you
though, but not for me and my kids.

Timothy Iseler: Yeah.

Ryan Isaac: Uh, it, it reached a
point where I tried to get back

in, I scouted for a couple years.

Ultimately, there's gotta
be a job there for me.

There's gotta be somebody interested
in bringing me back in certain roles.

And, and the game changed a lot in the
last 10 years as analytics have been

more and more, uh, a critical part of it.

Um, really the job I had in Arizona
that I loved as director of baseball

operations, I don't think that role
exists as it did 10 years ago anymore.

Timothy Iseler: Hmm.

Ryan Isaac: Not to say there aren't
other things I could do and would've

loved to have done, but once I got out,
I think, uh, I mean it was harder to

get back in, but also I was mentally
preparing for life outside of baseball.

Um, probably in a way too that
when I initially flew out to

San Diego 20 years ago without
a job, it's a different mindset.

By the time I pulled the plug on,
on the baseball, uh, pursuit, we had

one child and a second on the way.

So it was time to be a little more
responsible and, and certainly not,

not even, not in a career specific way,
but in a way that I had to move on.

Timothy Iseler: How did you find
your way into this fundraising job?

Ryan Isaac: Um, that's a good question.

Uh, my previous role, I was doing
something different, but I had

started right before COVID, um,
probably some time around the same

time that you launched your, your
career, uh, in financial planning.

And the, in retrospect, the benefit
to being in that environment was

we, the staff became thinner and
thinner, so those who remain had

to take on more responsibilities.

So I started doing more fundraising
than I thought I would be doing.

Uh, so it got me introduced to the field.

And gave me enough of a background
to be able to transition into a

full-time fundraising role in a,
with a different organization.

Timothy Iseler: Yeah.

Do you think you're good at it?

Ryan Isaac: Yes.

Uh, my daughter asked me the same
question last night, actually,

dad, dad, are you good at your job?

Uh, and, and I told, I'll
tell you what I told her.

I said, yeah, I'm good,
but I can get a lot better.

Timothy Iseler: Yeah.

Ryan Isaac: And part of it's just having
an understanding of the lay of the

land, of, of the school where I work
and getting to know people, spending

time, uh, getting to know families.

Some of it also is pushing
myself out of the comfort zone.

Um,

Timothy Iseler: Mm.

Ryan Isaac: making, making more
phone calls, not being for,

like, nothing is a cold call when
it's within a school community.

Timothy Iseler: Right,

Ryan Isaac: So I, I think part of it is
just being a little more, uh, rigorous

and persistent with, with my day and.

Timothy Iseler: right.

Ryan Isaac: So, yes, I'm good, but
I also see a path to be better.

Timothy Iseler: Yeah.

Well, the thing that, the reason I
ask that, and the thing that stood

out to me is when you're fundraising
is obviously you have to be talking

to people all the time, and a lot
of those people maybe wish you very

well, but are gonna turn you down.

So you have to be like very
resilient in the face of rejection.

Do you feel like part of your previous
led you to that position where you're

like, I can deal with people telling me
no and I'm gonna pick up the phone again?

Ryan Isaac: Yes.

And in fact, I was just cleaning out a
closet, a little area in, in my house,

and came across the rejection letters
I received, uh, from, from various

baseball teams when I first made a really
mediocre effort to get into baseball.

With 2000 I'd been in, I'd been outta
school for a year and a half, two years

or so, and just, I, I sent, I had whatever
the guide was, the Baseball America

guide or, or whatever the publication
was that listed all of the key people

in teams, front offices and the address.

And I sent pretty much, I
sent three letters to, to 30

teams, sent out 90 letters.

And even as I was sending them,
I realized I don't really know

if anyone's gonna be compelled to
respond to what I'm sending here.

I'm not doing anything proactively
to set myself apart, kind of

going through the motions.

But I'm not sure what else...

I might have been sure, I just,
maybe I wasn't really ready to

make the leap and to understand
what I was getting myself into.

But you know, a couple weeks after I sent
out the first batch of letters, like.

I got a postcard in the mail.

It was a rejection postcard,
but it had a team's logo on it,

and I thought it was so cool.

Timothy Iseler: Yeah.

Ryan Isaac: then, and then the actual
letters started coming in and I

was flipping through 'em and I've
got quite a collection of people I

ended up working with or getting to
know, my job or just one, you know,

one way or another encountering it.

I just thought like, it's a collection
of rejection letters from, you know,

a couple of 'em, i, I, I actually
took a couple pictures and sent them,

texted them to people I now know.

I'm like, Hey, look what
happened 25 years ago.

Timothy Iseler: When you were
working in baseball, did you run

into those people and tell them, or

Ryan Isaac: yes, I, I, I, at some point
I dug up a couple of those letters,

you know, 15 years ago or so, and

Timothy Iseler: I.

Ryan Isaac: realized what had happened.

So that was, I mean, it was fun.

It was also a good way
to build resilience.

And I think I just always....

I don't wanna say I took the rejection
in stride, 'cause like I wanted

the jobs, whatever I was getting
rejected from was something I wanted.

So it's not like I didn't get
upset over it and fueled me,

motivated me in one way or another.

But I didn't take it personally.

I didn't let it stop me.

And that's, that's been helpful
throughout my, throughout my life.

Timothy Iseler: Yeah, that's great.

So you have a career dramatic career
pivot and then COVID hits and you've

got this base, like you said, all this
baseball energy and it has nowhere to go.

How did you get started
with Warning Track Power?

Ryan Isaac: I had been thinking
about doing something along

those lines for a couple years.

When I was, after my daughter was born,
uh, my wife had her three month maternity

leave and went back to work after that.

I stayed home and was, uh,
full-time dad for, for that

one year and it was incredible.

Took incredible bonding
time with my daughter.

It was also challenging from a
professional standpoint, from

a intellectual standpoint.

And I wrote a couple baseball
stories for other outlets.

I wrote one piece for The Ringer, uh,
wrote a couple things for Baseball

America or Baseball Perspective.

So I was kind of training that
muscle and figured it's good

to keep my name out there.

I was concerned probably to my own,
hindrance, concerned that if I started

writing baseball, then people would
think that I'm back to writing and

wouldn't think about me as, you know,
in a baseball executive role again.

I was probably the only person who even
thought about that or considered that.

It's one, one of those moments
where you realize like, nah, no,

no one's thinking about you at all.

Good, bad or indifferent or otherwise no.

That's get outta your own
head and, and keep doing it.

Um.

So it was just one night I was sitting
at my computer and, you know, during,

during COVID for so many of us,
like we weren't working from home.

We were living at work

Timothy Iseler: Yeah.

Ryan Isaac: and there was, there
was no real boundary between work

and home and forget about work life
balance and anything like that.

But I had my work laptop and
I had my personal laptop.

Personal laptop was nearby and at
a certain time at night, I would

just shut down the work laptop and
open up my personal one just to

like, I think without even knowing
it, that was my line, that was my

boundary between work and, and home.

And a friend of mine had put something
out on LinkedIn about make that leap,

do that, that, that, that whatever
that is you're thinking about, do it.

It was towards the end of the year.

It's between Christmas and New Year's,
so it was in that resolution season.

And I replied, I just remember typing
some sort of reply to him on LinkedIn

and thinking as soon as I hit send or
publish or go whatever, I'm accountable.

Timothy Iseler: Yeah.

Ryan Isaac: So I did it and I was
like, I just kind of remember the rush,

the visceral feeling of it thought,
okay, we're, we're doing this now.

and that sparked it.

I must have had a backlog of ideas
of things I wanted to write about,

and just took it from there.

And it was a, it was an incredibly
healthy outlet and I had no idea

that's what it was gonna become.

But especially, you know, late 2020 and
the 2021 when we were still, um, somewhat

remote, uh, it was just a great way to,

to connect with people, uh, when we
weren't doing that more traditionally.

Timothy Iseler: Yeah.

How important is the audience
for you when you write?

Ryan Isaac: It's a good question.

What exactly do you mean by that?

Timothy Iseler: Well, I guess there's
maybe one version where you have hundreds

of essays you've written on your laptop
that nobody sees and you just do it 'cause

you love writing or, or maybe you have
an idea you're gonna collect them into

a book; versus when you're putting out
a newsletter, you know, part part of it

is that somebody's reading it and you're
writing so that those people can continue

reading what you have to, you have

Ryan Isaac: Right.

Timothy Iseler: it.

Ryan Isaac: I, I, I think when I'm in
the act of writing, it's for myself

Timothy Iseler: Yeah.

Ryan Isaac: and it feels good and,
and I can get lost in there and

chase after whatever ideas I have.

It's kind of the, the benefit of
doing it myself, being self-published,

it's, there's no editor.

I don't have to answer to anybody.

I don't have any formal deadlines or
specific talking points I have to get to.

Timothy Iseler: Yeah.

Ryan Isaac: And I've got a, a lot
of experience and stories from, from

baseball, and some of them are fun
stories to tell what happened some

point many years ago and some really
very well to a contemporary issue.

Something that happened in a game
yesterday that I can shed some light on.

And I, I can stay up really
late doing that and realize that

I, yes, I do that for myself.

What I notice is when I am out
of my publishing routine and even

my writing routine, I get cranky.

I get angry.

And, uh, there've been a couple other
writers, full-time writers, who I've

heard talk about, like, it's just
like their daily writing exercise

is a critical part of their mental
health and, and their happiness.

And I feel that, and there are plenty
of times like this is a side hustle

and I love to take more seriously and
more seriously and more seriously.

But there's only so many hours in the day.

And I definitely had moments, this is four
and a half years into it now, the first

year or two I was publishing like we,
Thursday morning, it was in your inbox.

And Wednesday night, if I was up
at two 30 in the morning to finish

something, I was doing that.

Uh, as my kids have gotten older and
stay up later and, and wake up with,

with greater demands and needs, I,
I've had to go to bed sometimes.

That it is really that simple where I
have feel that tug and I hear voices

of like, if you really want it, you
gotta keep writing, you gotta fight on.

And I think that's ridiculous.

I have a job, like I have a day job.

I, I have a full-time job.

Uh, I'm responsible to show up at a
hundred percent as best I can every day.

So sometimes I gotta go to bed.

, And it's not to mention I have a
wife and children who also need

me, so I can't get lost in it.

Especially if I could, in the earliest
days of it when we were coming on

COVID still in COVID, and, and again,
the kids were younger and going to

bed earlier and not, you know, waking
up, not needing another glass of water

or a snack or something like that.

So that's, that's been
interesting to navigate.

And I think from an audience standpoint,

I consider my audience in those moments.

And what I've learned, and it's really
no great surprise, is that when I am

writing, when I'm publishing regularly,
more predictably, the engagement is

much better and the feedback is better.

And, you know, I said talk about audience.

There were a couple times early on
where I, you know, there were a hundred

subscribers and trying to read the
engagement and see what's happening,

whatever metrics Substack has.

And I think like, is anybody reading this
at all other than like my mom and dad,

you know, like anyone really doing this?

And I get that one email from,
from a stranger commenting

or just saying Hi, whatever.

It was like, oh, cool, i'm shouting out
into the abyss and it's shouting back.

There's an echo here.

Like there's, there's life.

And that those little pieces that,
that seem to come whenever I want

one or need one feel like I need
one, they, they're motivating.

And that's the, the piece of, I think
audience interaction, especially

when it's digital and remote.

That's a piece that's, that's helpful.

Timothy Iseler: Yeah.

So you're on substack , I
assume, because you're, you

mentioned this is a side hustle.

Is it, are you monetizing that or is it

Ryan Isaac: I did, I
monetized it a few years ago.

Wasn't sure what I was really

Timothy Iseler: mm-hmm.

Ryan Isaac: supposed
to do or wanted to do.

And then I realized I used
to be a full-time journalist.

Timothy Iseler: Yeah.

Ryan Isaac: I still freelance from time
to time, freelance throughout my life.

I haven't done it a couple
years since like this, really,

but in Substack that is.

But like I worked in
baseball for 12, 13 years.

I'm a professional where I
was a professional writer.

I'm, I'm entitled to charge for this.

I don't need to give it all away.

Um, does bring in a little more
accountability, a little more guilt some

nights when I can't turn it out as much.

But I think those who do support me
with paid subscription understand

that more or less and, you know, are
supporting independent journalism

more so than paying for, you know,
some special late breaking news on,

Timothy Iseler: yeah.

Ryan Isaac: a, on a team or a trade.

Like they, they, my readers know what
they're getting from me in terms of

content and tone and general, you
know, general flavor, general style.

Timothy Iseler: When you were making
that decision, how did you think

about how much you should charge or
how much would be fair to charge?

Ryan Isaac: I looked at what
others were doing on Substack.

Substack, especially back, I was there in
the earlier days before they became the

kind of behemoth independent publishing
platform and more that they are now.

And, and they had some guidelines
and I think I probably like, looked

at the guidelines and went right
in the middle, like, ah, you know,

like $5 a month, $8 a month, 50 or
60 bucks for the year somewhere.

Okay, sure.

That sounds fine.

And it is not enough money to make
a difference, at least not today.

So like when somebody subscribes and
hits the paid button and does that, I,

that's a huge rush to, I remember the
first time I got first paid subscriber

who I didn't know, like, man, here we go.

This is, this is good.

But then I realized that I, I
could sell some of these stories

to other outlets and just get paid.

And that would be it.

I, I enjoy this connection.

The connection has value too, just
to, to owning those relationships

and them being able to drive them.

Timothy Iseler: How valuable is it to
you that you get to, I know you, you

feel like you have a deadline, but
it's your, you're, you're setting the

deadline, you're choosing the topics.

How much, how valuable is that
to you compared to cranking out

freelance articles that maybe you
could get paid the same or more,

but it's you setting the rules?

Ryan Isaac: At this point in my
life, it's just easier to be the

one setting the rules where I will
bite off more than I can chew.

And I think I'm finally getting
to that point where I realize,

stop, don't, don't do that.

It is, it's, it's, I, I know I
don't like the way, you know there,

there's nothing good comes from that.

So I've had a few ideas that I've
wanted to send to some people I know

who be in that position to let me
write for a, you know, a public outlet.

And I just think when,
when am I gonna do this?

You know, just more

it fits in my life right
now with how it is.

I think that's probably
the best way to put it.

Would I like to do more, and yes.

But that's just not where we are.

And I think, I think that's been a
big realization and a big part of

the evolution of it for me, because
I would like to swing back to being

a little more consistent, a little
more, I don't wanna say regimented,

but just more rigid with myself in,
in terms of a publishing cadence.

But at the same time, when my kids
wanna go outside and play whiffle

ball or ride bikes or whatever, like,
I, I'm not gonna say no, I'm gonna

lock myself up in my room right now.

And, and write, you guys go, go have
fun and go, go find mom instead.

Like,

Timothy Iseler: yeah,

Ryan Isaac: you know, it is so, it,
it, it's, it's where I am right now

today, and I can say that to you

and act like I believe it.

You know, there's still that, there's
still that part of me though, that

that's like, I've gotta find an, an
extra hour somewhere, but I'm not

waking up at 4:00 AM you know, I'm,
I'm, I'm not, I'm not doing that.

So,

Timothy Iseler: Yeah, I want
to share something and you tell

me if this resonates with you.

That, uh, my background is in the music
business and I found that the longer

I was in that business working with
bands, the less I enjoyed music as

recreation and I had taken the thing
that I loved and it became my career

and, and it stopped being my recreation.

Did you have like when you stopped
working in baseball, were you able to

enjoy it in a way that you had, you
know, before it became your career?

Ryan Isaac: It took a while.

Timothy Iseler: Yeah.

Ryan Isaac: It took a, and the first
layer to kind of breakthrough was

the, the hurt, the the hurt feelings
from having been let go by the DBacks.

And before that I worked for the Padres
and so it was fun to move from one

team to a division rival, and then
during the four years in Arizona, have

greater success for the most part.

And where in 2015, 2015 I ended
up scouting for Tampa Bay.

I was based in New York City
and but scouting for Tampa.

Um, and I can remember when the
Diamondbacks who played the Padres,

I, I, you know, what do you do when
you're rooting for both teams to lose?

And it, it was miserable.

It is no way to live.

It was no way to live at the time.

I think I just had to process
it and go through it that way.

And having kids, and having
kids interested in baseball

and, and also having kids I wanted
to have grow up in a healthy, well

adjusted home, I couldn't be that way.

And it took a couple years to process
some of it, but, uh, now I watch baseball.

My wife and I watch baseball with my
kids, and we all just do it as fans.

So, and part of my writing had been
to kind of recon, rekindle that

relationship with the game as a fan.

Timothy Iseler: Mm-hmm.

Ryan Isaac: So, but while it
was in the game, it didn't

dampen any of my enthusiasm.

In fact, I think it, it elevated it
just from, from the access and, and from

the understanding behind the scenes.

It, it made it even more exciting for
me, which I think made it even more

difficult to leave it and to be, you
know, on the other side of the fence now.

But through my kids especially,
it's just been fun to, to watch

games and root root for baseball
and, and have fun with it that way.

Timothy Iseler: Yeah.

That's great.

What's something That you that seemed
like a really good idea initially

and ended up not working out for you?

And then the sort of the counterpoint
to that is what's something that

seemed like it didn't matter at the
time that ended up being a really

good idea, really good decision?

Ryan Isaac: That's a great question.

I mean, moving back to San Diego
seemed like a really good idea in 2018.

Uh, and it's worked out fine, but I,
in my mind thought, well, my, my wife

was pregnant, baby number two for us.

We were in New York City.

It was time not to be in New York.

We didn't really have an ideal
destination, but I never wanted

to leave San Diego after the
first time moving out here.

And she liked it in our times
when we visited and she thought,

let's, let's do it here.

It's a quality of life move.

And I had a good network
here, so I thought.

And after about a month
here, I realized, oh crap.

Everybody I know is either in
baseball or a degree removed from it.

And I'm trying to find a normal job.

Really was not, I was not prepared
to market myself the right way.

It took a while.

It was, it was difficult.

I thought I would hit the ground
here and be turning down jobs,

uh, wasn't exactly that way.

Now that we're settled and landed.

It's, it's worked.

It's great.

It's good.

But, there was, there was that
first, you know, first year or

so where it was, it was rough.

It was rocky.

And so that was, uh, that was interesting.

I think I once asked, when I was
still at Wine Spectator and trying

to get into baseball, I once asked
somebody inside the game, I knew inside

the game of baseball that is, Hey,
should I, should I go to law school?

And I think I was, for the same
reason that I sent letters out to,

to every team, but didn't really
have any mustard behind them.

I was just kind of feeling, searching,
wondering what my next step would be.

And he said to me, do
you wanna be a lawyer?

And I said, no.

So then don't go to law school.

Terrible advice.

Timothy Iseler: Oh

Ryan Isaac: And, and I'm not
saying that I would've gone to

law school if he had said yes.

You know, it's, it's law school.

It's not that quick of a, it's
not that easy of a commitment.

There were several times during my
baseball career where I thought,

damn, that, you know, the law degree
would really be helpful right now.

And in

Timothy Iseler: Hmm.

Ryan Isaac: really a lot of
ways in which it's intertwined.

I just think about contracts
and financial side of it.

So that was, when I think about it, every
now and then, I can laugh at it now that,

you know, it was, uh, something that
happened 20 plus years ago and hasn't,

it isn't changing anything right now.

But I think about that sometimes.

Uh, Just in terms of who you ask for
advice and, and how, how you filter it.

Timothy Iseler: something that seemed
like it didn't matter at the time,

but ended up being really important?

Ryan Isaac: That's a good, good question.

I, I, what, what I'm, where my mind is
going with that is just relationships.

And, and it's not like I thought
of things that they didn't matter,

but the way you show up every day
and friends you make along, along

the, you know, along the journey.

I, I think I can look back on baseball
now and reach out to some people.

I have a, you know, I have a, like
a contact list full of people I used

to speak to regularly, and I don't
have a reason to talk to 'em much.

And it's fun seeing people who are
still in baseball, seeing 'em in

that space and being welcomed warmly.

And realizing that, for the most
part, I left things in, in pretty

good shape and, and built some, some
real relationships that transcend just

whatever our day-to-day was in the moment.

So it, it's not that I thought it didn't
matter, it was just something that I

never gave any thought to, because for a
while, at least while I was in baseball,

I figured I'd be in baseball forever.

Timothy Iseler: Yeah.

Yeah, it just seemed like regular life.

Ryan Isaac: Yeah.

How about you?

You have an answer to that question?

That's a, that's a.

Timothy Iseler: Oh, oh gosh.

I hadn't really thought
about it for myself.

I would say there's probably dozens of
things relationship-wise, where there's

certain different times in my life where,
uh, decisions I made didn't work out.

And, uh, in that way where you
find out which people were better

friends than you thought, you know,

Ryan Isaac: Yeah.

Timothy Iseler: I would say in that of
like, maybe I would, I don't wanna say

like people I was taking for granted,
but like when I, when I needed friends,

like the people who showed up, like
realizing like, oh, you know, when I met

this person 10 years ago, 15 years ago,
20 years ago, I didn't think about this,

but like, you know, now it's so valuable.

Sometimes I think too that the
things you turn down end up being

so much bigger because there was the
next thing that you know then, then

the next thing and the next thing.

So sometimes I think that there's probably
dozens of those of like little things

that I didn't pay attention to at all.

But you let them snowball
and it means a lot.

Ryan Isaac: Right.

Timothy Iseler: Do you think, or,
or let me say this a different way.

How do you think about success as
it relates to Warning Track Power?

Is it already successful or do you have a
vision for the next thing, next iteration?

Ryan Isaac: That's a good question,
and it's one of those questions that

sometimes I force myself to stop
thinking about it and go back and

go back to, and go back to writing.

That's all, you know.

There's no, I think in a certain
way it's already successful,

selfishly what it did for me,
especially that first year.

And again, to, to go deeper on
that, when I think I, I will think

of some, some people will come up.

I'll be watching a game or talking
baseball with a friend and something pops

up and it reminds me of somebody who I
had worked with at some point in the past.

Text the person, call the person, have a
conversation, end up with a story over it,

just chasing down whatever idea it was.

The fact that I have a reason to
reach out to these people who, to

people who I enjoyed being around and
enjoyed learning from and listening

to, that's hugely successful for me.

That that's, you know, it's more
than just scratching a an inch.

I think it's kind of like foundational,
to, to who I am or who I want to be.

Just having those voices, uh,
remain a presence in my life.

I think there's the other side of it to
it from a financial standpoint where,

you know, what's, what's the goal?

Would it be, would it be great to
be able to do nothing but write?

Like Yeah, probably.

If, if, if we found a way to
that eventually I would not be

complaining, that's for sure.

I also know though, it's
not happening today.

Like there's...

I don't have enough time and space.

Sometimes I get myself in trouble 'cause I
realize, oh, the idea I'm chasing is that

of a beat writer or a full-time writer
who can, who's at the ballpark every

day, who has access to easy access to
people on most days, and then has plenty

of time and space to write afterwards.

I think in the, in the time
that I have for Warning Track

Power, now we're doing fine.

But I I, we could come back to this
in, in 10 years and still writing it

in 10 years, it could have taken us
to a different level and I'm guessing

I'd still have, uh, ideas to make
it successful or more successful.

So.

Timothy Iseler: Do you think that the
like sort of post pandemic or like post

zoom world people are happier to just
get a phone call kind of out of the blue?

Ryan Isaac: I hope so.

Um, I, because, and I've started doing
that there, there have been a couple

friends I've spoken to in the last
month who I, I think we now colloquially

or ally use the word spoke to or talk
to when we're actually just texting.

Timothy Iseler: right.

Ryan Isaac: And

Timothy Iseler: Yeah.

Ryan Isaac: like to make that distinction.

I, I've lately just been thinking
about how can I be less digital in,

in all things and work in life, in
parenting and marriage and so forth.

And sometimes it, it's actually, I
think the answer must be really simple.

Just pick up the phone.

And then of course pick up your,
your iPhone and not get distracted

by anything else that's on there
to make the call to the person.

And you know, like we,
we used to make a call.

Now I feel like there's so much, like,
before I'm gonna call you, Tim, I'm gonna

text you to see if you're available to
receive this call as if you couldn't

just ignore me if, if you, if it wasn't
a good time, uh, as if, as if we ever

had that kind of choice 30 years ago.

So, uh, I think people are, I hope
I, yeah, I think people are more

excited to make more, I don't know,
I don't wanna call it authentic or

genuine connection, but it's simpler.

I actually, I have a, an
idea, I've got the story idea.

I just need some time to, to
talk to people and write it.

But I wanna publish an, an
edition of Warning Track Power.

I want to just get one

Timothy Iseler: publication.

Ryan Isaac: A, like a, you know,
four page folded newspaper or.

Leaflet or pamphlet or
whatever we wanna call it.

Just 'cause I ha like, I
don't know, just experiment.

See how people like it.

But don't send it out in an
email, don't have it digitally.

Figure out how to get addresses, like that
hardest part is getting addresses and,

you know, throwing the stamp on there.

But I've been thinking, I've got the
idea, I've been thinking about it

for a few months and will be very
excited when it comes to fruition

and actually print something and put
in the mail for people to, to hold.

You know, there, there's
that tangible nature of,

you know, the art of, you know, music.

Whether it's, you know, holding the, the
vinyl album versus the the digital thing

on, on iTunes or Spotify or whatever.

And I used to read magazines all
the time as like a teenager and

young adult when it was like, that's
why I worked at Wine Spectator.

I love magazines.

So to be able to return to that a little
bit, and do so in part, uh, because of a

motivation to take things off the digital
space and put them into the, into the

print to the slower, slower space of Yeah.

Something I think about.

Timothy Iseler: I, don't know
your audience, but it seems like

if you have an audience paying to
receive your newsletter, if there

was like a, the deluxe physical
copy, I think a lot of people would

be very excited to pay for that.

Ryan Isaac: I hope so.

I think like, look at The Onion.

Look what The Onion's done
in, in the last few months.

I think it's so cool that
they're back in print.

And I used to take a certain route from my
apartment in New York to the office where

I knew there was an Onion box on whatever,
you know, publication day it was to

make sure I could grab one on my way in.

Timothy Iseler: I feel very, very similar.

Like, I feel like there's some
part of getting like a daily

newspaper that's wasteful.

you, you see it, it just piles up.

You end up with a lot of newspapers in
the trash or the recycling or the compost.

But, At the same time, I engage
with it completely differently.

The reading news on my phone is
but it's so unsatisfying, and when

you're reading it on a physical
newspaper, the experience is so

different and the way the information
is prioritized is so different.

And you're not con like constantly
prodded to get to the next thing and

the next thing and the next thing.

It's, it's such a more
enjoyable experience.

It's like not, not efficient,
but it's more enjoyable.

Ryan Isaac: No, it's true.

I also, I don't know about you, but
I like where my mind wanders when I'm

reading either off the page of a book
or magazine or newspaper that it just

doesn't happen the same way on the screen.

Timothy Iseler: Yeah.

It, I feel the same way about
music, very much the same way.

Even if I'm listening on iTunes, I will
often play an album start to finish

rather than to pick out songs that I
like because whenever I start picking

out songs that I like, as the song I
wanted to hear is playing, i'm already

thinking like, okay, what's next?

What's next?

You know, and that, that's fine if you're
like a DJ and you're trying to impress

people or something, but it as a, a form
of recreation for me, I don't like it.

Ryan Isaac: Yeah, I, I get that.

I get that.

Not to take it too far down, down
this tangent, but last week I did,

did the same thing just with albums
and just started with the first Black

Sabbath album after Ozzy passed away.

Timothy Iseler: did the same thing.

I did the same thing.

Ryan Isaac: And, and I realized like,
damn, I, I, like, I, I know all their

hits, but I never listened to any
album start to finish and I thought.

I found a new favorite album of mine.

It came out 50 years ago.

Like, this is incredible.

And, and I think it's probably a little
over exaggerating the, the point here,

but just hitting play and leaving it
alone gives you a chance to experience

things in a different way and, and
see things, hear things that you

wouldn't have otherwise experienced.

Timothy Iseler: Yep.

Excellent.

something you think you do really
well in your own financial life?

Ryan Isaac: I have a realistic view
of, of where we are or what we do.

The best answer is probably defer to
my wife for, for bigger decisions.

Uh, she's always been
on top of her finances.

I think when we met, she was definitely
better organized and, uh prepared to, to

become a full fledged adult and parent.

I think I learned how to make it work for
the most part with whatever I was doing.

and that still at times came with the
help of, you know, parents or, you

know, open the mail and get $20 from
grandma on that day and be like, oh God,

nice, now I can, now I, now I can do
whatever I was hoping to do or whatever.

So that's, I, I, I think I was able
to kind of navigate career and some

career changes through re again,
resilience and also just kind of

getting by with, with what I could.

I certainly changed once I was married,
once other people relied on me.

Timothy Iseler: What's something
you love to do that's cheap or free?

Ryan Isaac: I take my kids to the beach.

Timothy Iseler: Oh

Ryan Isaac: Um, yeah, I mean
that's, that's an easy one.

And certainly paying for it in
other ways here in California,

Timothy Iseler: uhhuh.

Ryan Isaac: you know, the,
the, the beach is always good.

Just being, being in a, in San Diego where
the weather is generally cooperative,

there's so many things you can do outside.

Timothy Iseler: Yeah.

almost no time of year where
it's not pleasant in San Diego.

Ryan Isaac: Correct, correct.

And having grown up in Baltimore, I,
you know, I, I appreciate the humidity

and appreciate being out of it.

Timothy Iseler: Yeah, yeah, yeah, yeah.

What's something you love to do
that's expensive but totally worth it?

Ryan Isaac: Ah...

dine

out at nicer restaurants.

Certainly love that.

I, I, I, I enjoy, I, I've become, I,
I think since I started writing more

regularly for myself, I've gotten
more in touch with the creative side

and I certainly see Kitchen Life,
kitchen work as a creative endeavor.

Uh, so I like going out and eating
and seeing what's happening?

I think you can learn a lot about the
city and the area through the food.

And having worked at Wine Spectator,
that was, you know, a big part of it too.

And just to kind of tie it back in here
with food, wine, and money, I, I can

re can remember telling my grandfather
many years ago when I was still at Wine

Spectator 25 years ago or so, like, here's
the deal, grandpa, when the day comes

that I no longer work at Wine Spectator,
I can't drink wine anymore because

my taste now far exceeded my budget.

Timothy Iseler: Yeah.

Ryan Isaac: And, you know,
that was certainly a perk in

the job at the front of it.

And then I moved to San Diego to work
in baseball and just drank IPAs all the

time 'cause they were, you know, two or
$3 The bar on the bar on the special.

Timothy Iseler: yeah, yeah.

Are you, are you able to get back
into wine now or are you still an

Ryan Isaac: yeah, I, I, I did that
and that's like my two passions,

my two biggest passions, baseball
and wine, were both careers for

a while, uh, which is great.

But then, like you were saying,
with music at a certain point, I

think for me, at a certain point,
what the hell do I do for fun now?

If, if fun and professional endeavors
are intertwined, like balance that,

like that's, this is my own making
any, any kind of lack of, lack of

boundaries and balance here is my fault.

But I did, I, I wrote, uh, started
writing a little more about wine

again, and I'm actually in the
process of merging the baseball in

the wine worlds into, into something.

I don't know if there'll be a
couple one-off things or it's own...

like I don't have, I, I wish
I had more time for all of it,

Timothy Iseler: yeah,

Ryan Isaac: uh, but I did that, like I
ended up in baseball because of wine.

And built a lot of strong
relationships through the two, finally

realizing like, this is who I am.

Might as well own it.

Timothy Iseler: Baseball players...

it could be like broadly or, or just
even specifically, are they into wine?

Because I know that's really taken off
in basketball in the last 10 or 15 years

of athletes being really into wine.

Ryan Isaac: Yes.

Uh, they are, and I think probably
more so today than when I was around

them more often, 10, 11, 12 years ago.

I think as all sports, all, all
athletes salaries have, uh, risen,

so have some of their tastes
and, and access and expectations.

I think in the, in the early states
of my exposure to baseball players

and some of those finer things, it
was easy to watch where somebody would

grab the wine list and just boom,
go to the bottom, but whatever that

bottom one was the most expensive.

Yeah.

We'll have, we'll have a couple of those.

And I could then see it evolve where guys
showed up and actually knew what they were

looking for, what they were talking about.

Uh, so the, the answer is yes.

Uh, I think a lot of coaches and
managers have gotten into it too.

And you know what, it's,
it's a good way to talk about

something that's not baseball.

It's a good way, I think
to, and, and especially like

players have limited windows.

You know, you get on a plane, you
fly from one city to another, perfect

amount of time to open a bottle
of wine, have a glass of wine, you

know, on, on the plane, share it with
people, people like, and most of the

guys are, they're good teammates.

They like to share, they like
to expose their teammates

and friends to other things.

So wine provides that medium.

Timothy Iseler: Yeah.

Well, Ryan, end every episode
with a question from my guest.

Here's yours: what was the
biggest obstacle you faced

during your career transition?

I would say, aside from the
timing of it, like , I made

this transition before COVID.

I, I opened for business six months before
the pandemic, so that was just difficult

to be starting over new career, working
for myself, and then everybody I thought

I was gonna be working with had no income.

So that was certainly
tremendously difficult.

I think though, what I would answer
is that the biggest obstacle is kind

of what you mentioned of when you're
inside the industry, you have all

this access you're around the people.

And, and I don't know that I
took that access for granted, but

I kind of assumed that my peer groups
would remain more or less the same.

And then when I was not no longer working
in music, I, it was like I, the people...

i, I've, it's something I've had to
work on for myself to find the nice

way to say about it, but, you know,
I'm not there working with them,

so they're not thinking about me.

And, and that was sort of
hard of like having to,

to, in some ways like my network
and in some ways just accept that

like some of the people that I
thought of as friends were not.

You know, it was, it was more
circumstantial and, and not to

assign negative intent to that, just,
that's how it happens, you know?

So I, I would think it's, for me, the
biggest obstacle was, was stepping

stepping out of that community and
then realizing that the consequence of

that is that I'm, you know, don't have
that direct connection like I used to.

Does that make sense?

Ryan Isaac: It makes a lot of sense.

I think it's a big part of
tying identity to what you do.

Timothy Iseler: Yeah, totally.

Ryan Isaac: you know, when you're,
when you're in the clubs at live

shows every night when you're at
the ballpark watching game, like at,

at least for me, I was happy to tie
my identity to, to my credential.

Uh, so it's about, you know,
finding, finding that value

elsewhere, that self-worth.

And, and I think the social network
also, like you're saying, it is, while,

while my job, I know a lot of the people
you've had on are independent contractors

are working for themselves, hustling
it in a different way, while my job in

baseball was a salaried job and on paper
just like, you know, a nine to five gig

wherever, when the game starts, most of
the time it's seven o'clock at night.

Timothy Iseler: Yeah.

Ryan Isaac: It's a different cycle.

So when, whether you're, you know,
I'm far away from being on the field

playing, but still the adrenaline
at first pitch, you're peaking

at 7:05 PM that's not normal or
natural or healthy in a lot of ways.

So, and, and same thing
being, being at live shows.

Those aren't happening at 10:00 AM Uh,
so just coming off of that lifestyle,

learning to try to go to bed at a
reasonable hour and, you know, not

have a few beers at 1:00 AM 'cause it
seemed like the right thing to do when

everybody else was, you know, it's

Timothy Iseler: yeah, yeah.

Ryan Isaac: of it.

Timothy Iseler: Yeah.

It's, uh, that you're spot on with that.

Like, it would, it would be not unusual
to be finishing my workday at midnight

and then, you know, you wanna knock
back a few after work and then, you

know, go to bed at two three and get
up in the morning and do it again.

It's, it seems like a great
lifestyle when you're in it.

so hard when you're out of it.

Ryan Isaac: Yes, indeed.

Timothy Iseler: But, I guess also I
would add this to your, to, your question

to me is think, I think it would've
been much easier, in some sense, it

would've been much easier for me to
change careers and get a job versus

changing careers and starting a business.

And it, it's tough for, I don't
think I could recommend what I did

for most people, but at the same
time, after so many years of working

outside of the mainstream, I also
didn't like I could necessarily

stomach it to go in and, and get like
my first straight job in 20 years.

I didn't know if I could do that or,
or, you know, start at as an entry

level position at whatever, you
know, get a job at Fidelity as the

Ryan Isaac: Yeah.

Timothy Iseler: at the front desk when
somebody wants to talk about investments.

I just didn't think I could do that.

So

Ryan Isaac: It's like getting
released from Shawshank.

You just might not make it on the outside.

Timothy Iseler: yeah.

Yeah.

So it would have been easier if I had
not started my own business, but I also

don't know that that was possible for me.

Ryan Isaac: I get it.

Timothy Iseler: Yeah.

Cool.

Well, do you wanna share where
people can your newsletter?

Sign up for your newsletter?

Ryan Isaac: Sure.

Uh, it's WarningTrackPwr.com.

Uh, power is PWR: WarningTrackPwr.com.

And you can find me there.

And, uh, that's the easiest way.

Timothy Iseler: Killer.

Well, thanks so much.

I really appreciate you doing this.

Ryan Isaac: Thank you, Tim.

It was great being with you.

Great talking to you.

Timothy Iseler: Yeah, man.

Take care.

Ryan Isaac: Thank you.

Thanks.

Timothy Iseler: A big thanks to Ryan for
talking with me today and for opening up

so much about the challenges of starting
over after leaving a career that he loved.

As a career changer myself, I can totally
relate to a lot of what he shared.

Again, you can find Ryan's
baseball newsletter, Warning Track

Power, at warningtrackpwr.com.

Okay, that is it for today.

I will be back next week to talk
about the pros and cons of paying a

professional to manage your investments.

That is, of course, something that I
do professionally and, even though it's

easier than ever for you to manage your
own investments, I've seen firsthand the

difference it can make when you offload
that responsibility to a professional.

That's next week, but first:

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