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The Thing We Never Talk About is an educational podcast about personal finance for creatives and other weirdos. We'll discuss managing cash flow with a lumpy income, when to save & when to invest, and how to reduce stress & build confidence when it comes to your money. No hot stock tips, no complicated strategies, and no finance bro jargon. We'll hear from artists, musicians, creative professionals, and other weirdos about how they navigate these questions for themselves. The Thing We Never Talk About is hosted by Timothy Iseler, CFP®, a former recording & touring audio engineer with 18 years experience in the music industry.
Timothy Iseler: Mike, I finish up every
show with a question from my guest.
Yours was regular IRA, Roth IRA or SIMPLE?
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 in Durham, North
Carolina, helping musicians, artists,
and other people with weird jobs make
smarter decisions with their money.
You can learn more 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.
And if you enjoy this podcast, you should
also check out my Keep It Easy Newsletter.
I write about exactly this kind of
stuff and share it there weekly ish.
You can subscribe
Iselerfinancial.com/newsletter.
Today I'm talking with
self-employed writer Michael Perry.
Mike is a former registered nurse
who decided to take a chance
on himself and pursue being a
professional writer full-time.
In the 30 plus years since he made
that decision, he has supported himself
solely through writing and creative
work, and has written over 20 books,
some of them New York Times best sellers,
as well as countless essays, profiles,
and other less glamorous writing gigs.
Mike shares a lot of lessons he
learned through that career in his
new book called Improbable Mentors
and Happy Tangents, which is out now.
Mike is also a volunteer firefighter
and still keeps his nursing
license up to date, just in case
this writing thing falls through.
We had a great conversation about
managing the financial side of a gig
based job, the ups and downs of working
for yourself, and how learning to manage
his money has helped him continue to
do the job he loves for over 30 years.
All right, here we go.
Michael Perry (Mike): Hey, Tim.
Timothy Iseler: How you doing, Mike?
Michael Perry (Mike): Good.
Timothy Iseler: Cool.
Thanks for being here today.
Michael Perry (Mike):
I am happy to be here.
Looking forward to the conversation.
Timothy Iseler: Great.
What do you tell people
you do for a living?
Michael Perry (Mike): Well, it's
funny, I struggle with that a little
bit because I'm, I mean, I don't
mean to be overdramatic with the term
struggle, but I have a hard time just
coming right out and saying what I do
because I was raised very blue collar.
I grew up on a farm.
I grew up logging.
I worked on a ranch in Wyoming.
And although I, I loved books as a kid,
the idea of saying that you're a writer...
on the one hand, it, it's all
about having soft hands and not
lifting their stack and stuff.
But also there's that, and part of
it's Midwestern, but part of it is blue
collar, that there's this almost implied
pretension with saying you're a writer.
And I just, so I, I do tell people
I'm a writer 'cause that is everything
I do, no matter how it manifests.
It, it, it doesn't happen unless
I sit down alone and write.
But yeah, at the end of the day, I
say I'm a writer, although I admit
that I have a tick where I do tend
to say that I a, I am a self-employed
Timothy Iseler: Ah,
Michael Perry (Mike):
'cause where I come from.
That does carry some weight.
Timothy Iseler: yeah.
Michael Perry (Mike):
it happens to be true.
I, I've been a self-employed
writer for a long, long time.
Timothy Iseler: How long have you
been self-employed at this point?
Michael Perry (Mike): I quit my last job
where I actually got a paycheck in 1992.
Timothy Iseler: 1992.
Congratulations.
Michael Perry (Mike): Yeah.
Timothy Iseler: what was that last job?
Michael Perry (Mike): So I have
a nursing degree and I had a,
a great job working as a nurse.
I worked for a surgeon and then I worked
on a neuro rehab unit taking care of
folks with traumatic brain injuries,
spinal cord injuries, that sort of thing.
But I very accidentally
developed an interest in writing.
And I, I wanted a job where I could just
put in the hours, do a good job, I was
conscientious, but, but not have to put
in a lot of thought outside that work.
And I also wanted to do something that
had to do with words because I, I didn't
have any background in that I was a nurse.
And so I took a job as a proofreader
for a company that, a company that
put on legal seminars for attorneys.
And I literally proofread
brochures eight hours a day.
But it, it, it was work.
I was working with words and
I was scanning and, and, and I
was learning to correct things.
And then also I got to a
point where I was doing...
the attorneys had to submit bios
and they were only allowed, I don't
remember, let's just say 300 words.
Well, they, of course, being attorneys
would submit 15 page bios with
everything they'd ever done, and I was
the guy who got to cut their bios down.
And so what I didn't realize at the
time was it was a great experience
in learning how to be ruthless
in editing and dealing with egos.
So I learned how to condense and edit.
And so it just was a way for me,
what I would do is I put in my hours
and I was very conscientious, but
man, when I clocked out, I went
home and I wrote until, you know,
midnight and I just wrote and wrote.
And I was writing poetry and
I was writing, used car ads.
I was writing whatever
it took to pay the rent.
and I was sending out essays, and I
literally went to the library and I got a
book on how to be a writer, and I read it
because I didn't know how to be a writer.
So I'd go home and write and, and
then finally, and I, I think it was
the spring of 92 or something like
that I just, I quit on very good
terms and went out to be a writer.
And the phrase I always use is that
I jumped out of the airplane and, and
just knit my parachute on the way down.
Timothy Iseler: Yeah.
Michael Perry (Mike): Yeah.
Timothy Iseler: So that was gonna be
my follow up was like, did you have a
thing where you were like, okay, I'm
leaving my job, but I have this thing.
Michael Perry (Mike): Yes.
And I, and I need to be
really upfront about that.
So I had many years early on where,
you know, when you go back and look
at your social security statement,
I had a lot of four figure income
years between 1992 and 96 7.
But I was a single guy
living in rural Wisconsin.
I had a house payment
of 167 bucks a month.
You know, so I don't ever want
to plead that I really struggled.
And then the biggest
thing was I had no money.
I had no idea what I was doing, but I
had a nursing degree and a, a license
in my back pocket, and I could go get a,
a good paying job, literally in a day.
So that was a huge help to me, just having
that and, you know, I've always joked my
plan was, I figured it would never work
and I would just go back to nursing.
And I always say 30 years
later, that's still the plan.
I still renew my nursing
license every two years.
Yeah, so I, I definitely had had
some things in my back pocket.
Timothy Iseler: Since then, you've
been doing this over 30 years,
working for yourself over 30 years,
you've published a lot of books.
What do you think are the biggest
differences between what people
think the life of an author
is and what you actually do?
Michael Perry (Mike): It's interesting,
and by the way, I just go off on
tangents 16 different directions
every question I get, which I guess
is how I've made a living as a writer.
So I'm already thinking of
three different answers.
But the first thing is it's amazing
and I think, you know, musicians,
artists of all sorts deal with this.
The average person, and even a lot of
people who love writing and want to
be a writer and want to get published,
they're envisioning an industry
that ceased to exist 50 years ago.
Timothy Iseler: okay.
Michael Perry (Mike): Even me,
I mean, my first book deal with
a major publisher was in 2002.
And I remember at the time there was
this little company called Amazon,
kinda wondering what they were up to.
So I think there is this vision
that, you know, I'm just sitting
around thinking thoughts with my
cup of tea and being reflective.
And guess what?
That I do get to do that.
And I love that and that's why I'm
still in it after all these years.
And that's why I'm in it,
despite all the changes.
I got up this morning and I made coffee
'cause I like coffee better than tea.
But I had my coffee and I've
been working on an essay that
may or may not ever find a home.
But I also did QuickBooks
Timothy Iseler: Uh.
Michael Perry (Mike): and I
also checked to make sure that
the quarterlies had been filed.
And so one of the other things I've
always said is that I, I love going
to the coffee shop and sitting
there and, and acting like a writer.
But at the end of the day, I also
have to just make sure that business
gets taken care of because that's
what allows me to keep doing this.
So I think it's, it's, it, it's, I,
and I think people also have this
idea that if you write something
amazing or heartfelt, that it will
automatically find an audience.
Timothy Iseler: Hmm.
Michael Perry (Mike): And the
cold hard truth is that no.
No.
I hear people every day who want
to write books or tell stories that
are moving and deeply personal.
And the fact is you still
gotta find eyeballs.
But I'm stubborn and I love
what I do and keep doing it.
So.
Timothy Iseler: yeah,
Michael Perry (Mike): I dunno if
I even answered your question.
This, there's gonna be a lot of this.
Timothy Iseler: all right.
That's perfect.
Perfect.
You said something there, and it, it
reminded me of like certain musicians
that I've worked with who I certainly
won't name, where they managed to go
very quickly from just starting out to
having a significant amount of success.
And it seems like they kind of go
from like, I don't have any money
to, I have enough money that I just
pay people to think about it for me.
And they miss that middle period
of kind of slugging it out and
maybe not learning how to do
QuickBooks, but learning, learning
somewhat of the business side of it.
And I, I, I think that's so important.
Even if somebody wants to hire someone
to be their business manager or be their
accountant or whatever, to at least have
a cursory understanding of if you're
self-employed, whether you called a,
a business or not, like some cursory
understanding of is how my business works.
Michael Perry (Mike): I had so
many things that were lucky breaks
for me, and one of the main ones
was, because I was a farm kid...
i, again, I loved books.
I grew up reading voraciously, but to
me, authors, that was a capital a word.
They were people in the distance
who you never met, and you, they
worked in this mysterious place.
So despite the fact that I was a
very bookish kid, I was a football
playing, pickup truck driving, deer
hunting knucklehead, and in all other
respects, and it just never occurred
to me that I could be a writer.
So when I did come to writing, I didn't
come at it with the idea that the
world was breathlessly awaiting my art.
I just wanted to do it.
And so that really excused me from
a lot of the self-imposed artistic
constraints that people put on themselves.
You know, and we can get into later, you
know, about being businesslike, about
promoting your stuff, about being very
aggressive about selling your work.
I was spared that because I
just didn't know any other way.
And then the other thing that really
helped me, I had a father who was a
farmer who taught me about multiple
revenue streams, even though he didn't
call it that he was a tiny dairy farmer
with a big family, and you didn't
survive if you just relied on one thing.
And so he milked cows and we logged and
we sold hay, and we had a flock of sheep
because, uh, on a good year, the lambs and
the wool would cover the property taxes.
You weren't ever gonna get rich,
but you had, so you weren't
depending on just one thing.
That helped a lot.
But the, the, the other thing that
really helped me, and I, I mentioned
not thinking of myself as a capital
A author or a capital W writer,
which I still maintain to this day, I
didn't have really any expectations.
And so like when people say My dreams
came true or I achieved my goals,
I've never dreamed about doing this.
I never set a goal in my life.
I just believe in forward motion.
And I'm not denigrating
that way of thinking.
It works very well for a lot of people.
But I was just always just get up
and milk the cows, get up and clean
the, you know, shovel the manure.
And you can extend that metaphor
to my writing as far as you like.
Um, But because I just came at it
with that attitude, I didn't have
goals and dreams and, and what really
helped me is that I, what the phrase
I came up with the other day is that
everything that I've ever achieved, I
achieved 10 years after I hoped I might.
Timothy Iseler: Yeah.
Michael Perry (Mike): And I
achieved it about 40% of what
I might have dared dream.
Timothy Iseler: Yeah.
Michael Perry (Mike): And, and
so I haven't become wealthy and
famous, but I also, by the time
good things happened to me...
So when I signed my first book
deal with a major publisher,
I'd been writing for nine years.
I was in my thirties.
And when it did better than any of us
in expected, including the publisher,
I was fortunate enough to not fall into
the trap of believing that A, it was
successful because I was brilliant.
It's a really good piece of work.
I worked really hard on it, but
I also caught some lucky breaks.
There was timing, there were all these
other things that I was old enough
and seasoned enough to recognize
that, that really helped me a lot.
And then also just, I had also had
enough friends in the arts or in in music
especially, where I was not so naive as
to think that the next book was gonna
do as, as, as good as the first book, or
that there would even be a second book.
And so that has really helped me, I think.
It's not so much low expectations,
it's just pleasant surprise that
anything good is happening at all.
Timothy Iseler: Yeah.
Yeah, yeah, yeah.
Michael Perry (Mike): And by the
way, they've never gotten huge
with me, but they got big enough
that I can't handle it myself.
And again, we can get into this as much as
you want, but you know, then I do have an
accountant now and I do have a part-time
manager, and I, and I do have QuickBooks.
You know, I was able to, to move into
that stuff slowly and in increments
Timothy Iseler: yeah.
Michael Perry (Mike): I think that
was one of my biggest advantages.
Don't get me wrong, I would love for
Oprah to call and just give me $5 million.
And I'm ready to deal with
all the problems that, that,
that, that could precipitate.
In the meantime, there's just been
this very steady, gradual, sometimes
growth and sometimes just maintaining
that has helped me to just kind of surf
the waves as they come in, I guess.
Timothy Iseler: So you mentioned
Oprah and that anecdote comes up
in your new book called Improbable
Mentors and Happy Tangents.
And you share the story of when you,
you wrote an essay, and Oprah wanted to
have you on the show and you said No.
mentioned several times in the book
how as a freelance writer you just felt
like you had to say yes to everything.
So here's an opportunity to
potentially have like an easy
ride to the top, and you said no.
So how do you think about saying
no in a world where getting the
next opportunity is so important?
Michael Perry (Mike): Yeah, because as
you mentioned as a freelancer, and, and
I know that musicians, especially like
session musicians and folks like that,
when someone calls and says, can you,
you, you don't even let 'em finish.
You just say Yes.
And as a freelance writer,
I do that all the time.
I, in the book, Improbable Mentors, I
talk about, you know, how I spent 10
years writing about music and mostly
country music and that it was a complete
accident because I had written one
thing about country music and then
an editor of a major country music
publication called me and said, are you
the guy who writes about country music?
And I said, yes, I am.
And you know, it's your lucky day.
Timothy Iseler: Yeah.
Michael Perry (Mike): So, yes, I
do say yes almost all the time,
but no has become very important in
two respects with the Oprah thing.
So I had a, I've been a volunteer EMT and
Firefighter for years, and I was headed,
up to northern Wisconsin for a recording
session with some musician friends,
and I came across a gentleman who'd
been horribly injured in an accident.
The very consolidated version of the story
is in, in caring for him I was exposed to,
he was HIV positive and, and so I wrote,
and, and this was back in a time when.
Folks really didn't know a lot
about that and, and there was
a lot of negativity about it.
And I was just trying to do my
best to explain that, you know, I
myself have to learn about this.
And it doesn't matter what you think
about the origins of the disease
or whatever your issue is with
it, it's here and these are our
neighbors and we need to help them.
And so I wrote this essay about that
and then Oprah's folks called and
they said, we want you to be on Oprah.
And of course that's gigantic.
But then the first next thing
they said is, it's a show
about heroes and you're a hero.
And I said, well, I'm not a hero.
I was really, felt really
uncomfortable with that.
I said, that was not the
purpose of this essay.
And so I declined.
I said, no, if you're gonna
have me talk about being a
hero, I'm not gonna be on there.
And in the book I say, you
know, it might've been the
biggest mistake of my career.
Who knows?
But I don't think it was
because I wasn't ready.
I was not very seasoned at that point.
I think I maybe had one or two
books, but they were self-published
and they were, they weren't awful,
but they were nowhere near where I
was headed, even in terms of craft.
And so if I had said yes, I'd
have probably been on there,
had a brief little exposure, and
everything would've gone away.
Instead, 10 years later,
you know, I get a book deal.
Or I guess it was five years
later, but, and then I was ready.
So in that case, saying no,
I think was the right thing.
The other thing, this is a tangent,
I didn't mean to go on to, but
since this is the finance show...
I got a thousand dollars for that essay.
I had never gotten more than $75
for anything I'd written in my
whole, at that time, brief career.
And I went, at the time I was right,
I had a buddy who used to play in
the NFL, he used to play for the
Packers and he was very well off.
And when, whenever we went to lunch,
he'd always pay and, and I got this check
for a thousand dollars from Newsweek.
And I remember joking with him, he took
me to lunch and I was joking with him.
I said, yeah, I'm gonna invest
it all in a mutual fund.
And he said, well, you should.
And I remember going, oh wait, what?
And he literally took me across the street
to, I think it was an Edward Jones rep.
And he said, this is my guy.
Just, you know.
And so I took a thousand dollars and
I put it in some mutual fund that
I don't even remember now, and then
of course didn't have any more money
to put in for another five years.
I watched that grow and then from, you
know, and I'm not with them anymore and
I, you know, there are other changes,
but that was a huge, pivotal moment
in that I, I joked about it because
I came from, I didn't, I had parents
who were very frugal but didn't trust
investing or anything like that.
That was, again, for rich
people in big cities.
Thank goodness that guy had
me do that because it made a
huge difference down the road.
Now to get back to the theme of
saying no, what I do have learned
to do now is you gotta get paid and
you gotta get paid in a manner that
is, will support your endeavor.
And I'm pretty unapologetic about that
because we can get into the whole idea.
Are you selling out?
Should you be a peer artist?
Well, here's the bottom line.
Every time I get paid to, to do my
art, it allows me to do more art.
And I'm not beholden to anybody.
I'm working on my own time.
And to be clear, my manager, who's also
my booker, we, we have a sliding scale.
You know, if it's a little local library
and there's just no other way they can
rate, you know, we're gonna work with 'em.
But I get asked all the time to do free
stuff, and I feel bad all, every, I mean,
I have a huge amount of post Calvinist
Midwestern guilt about saying, well, but
you simply, I, you know, I have kids, and
they had braces and there's still college
tuition and, and, and being, buying your
own health insurance since 1992, I mean, I
can go on and on where I just, I can't say
yes every time if that number isn't right.
And also it's.
This is gonna maybe get me in a little
bit of trouble, but there's an irony
in that often the people who ask you
to work for free are the same people
that are always complaining that no
one can make a living in the arts,
Timothy Iseler: Uh,
Michael Perry (Mike): arts community
is, is and, and some, some of these
people are, my dear, dear friends,
and, and many of these people are doing
work that I believe is very important
and I try to support it however I can.
But the number of times that
you're asked to do something for,
you know, the arts, and they say
the arts just are undervalued.
We need to promote the arts.
And by the way, you know,
we'll give you this key chain.
Well, this is inimical
to the endeavor, I think.
And it, it's very tricky.
It's hard because I, I understand,
especially in these times, you
know, support for the arts.
And, but in, in, in my experience
also, if you get paid professionally,
you get treated professionally.
Timothy Iseler: Yeah,
Michael Perry (Mike): Here's
another thing, so I'm, I don't
know how old the average person is
you're interviewing, I'm 60 now.
I feel like I'm 25, but I'm 60.
And I'm now, I've now lived long enough
to watch some of my true artistic heroes,
people that I thought had it made and that
were amazing and that change in my life.
And then now they've hit an age where
they don't have health insurance
and they're, and they're sick, or
they've lost their house, and you
all of a sudden you realize, oh...
what is that trade off?
Where's that balance?
You know, they were this amazing
artist that really inf influenced
me, but now they're in a terrible
state or their family needs help.
And so there's also been a very
pragmatic part of me that has tried
to make sure that if something
happens to me tomorrow, that my
family doesn't have to just freak out.
And again, that's a tricky thing.
'cause I'm not trying to say
I've got it all figured out.
I'm not trying to say I'm in any
way superior because I'm not.
But it is a reason to go beyond the
idea of what is a pure artist as and
extend it to the idea of actually
taking care of your situation
so that you can make more art.
Timothy Iseler: So you've mentioned
a few things that you've picked
up to try to manage your business
better, understand your money better.
What's something that you started doing or
a tip that just was so much more valuable
than you thought it would be at the time.
Michael Perry (Mike): Keep
track of your mileage.
Timothy Iseler: Yeah,
Michael Perry (Mike): Yeah, I mean,
I drive a 2002 Toyota van on tour and
like every mile is money in my pocket.
Timothy Iseler: yeah.
Michael Perry (Mike): I'm very
legitimately claiming that mileage.
And when I get home from a 300
mile gig, like I can take a big
chunk of money, very, you know...
legally and with, with
a free conscience...
and it's little things like that.
Like I'll have, I do sometimes have
artist friends, like, oh, I don't know.
I just, I hate keeping
track of that stuff.
I'm like, dude, it's, it's cash.
Timothy Iseler: Yeah.
Michael Perry (Mike): So some
of the little things and keeping
track of my business expenses.
That was an early one.
And I learned, thank goodness again,
because I didn't know anything.
I just started reading and I,
I learned about tax deductions
and I'm super, super honest.
I mean, I keep paper trails 'cause
my whole thing is, you know, if
someday I get the audit, I want to be
able, if they say you can't do this.
I wanna say, okay, that's fine.
But you notice I didn't hide it.
I mean, we're, I'm very, and,
and my, I have an accountant
now and that's our rule.
It's, I said, get me every break.
You can, but don't break any rules
and let's keep a paper trail.
So those little things helped.
The other biggest thing that happened
to me was I lived, as I said, on pretty
much nothing for years, and then I
signed a book deal with Harper Collins.
And I didn't get life changing
money, but I got more money in a
one chunk than I had gotten in, in
a long, long or ever in my life.
Of course, you had to divide that
check by three to four years because
that's what it was gonna be for me.
That was my income.
So it wasn't that number.
It was very much smaller
than that over time.
Well, what happened is, of course I
learned a lesson about taxes and what
happens when you get a chunk of money.
And so my accountant at the
time said, you need to form.
An S corporation.
And by the way, I listened to your
great episode on LLCs versus Scorp,
and I've gone back and forth on whether
I should have done one or the other.
And I'm very happy now, 20 some
years in that I did an S corp
. But that was a huge step because if this
is gonna be your life, your income, people
can't see this, i'm making my hand go
up and down like a rollercoaster, but
that is also part of the freelance life.
You're gonna have good years and
then you're gonna have years where
your, your sub poverty level income.
And so that was a huge lesson.
However, you can smooth things out.
And now we're back to that thing
about, well, I don't wanna spend
time with QuickBooks, or I don't
wanna learn about tax code.
And it's like, yeah, but that
lets me write more essays.
Timothy Iseler: Yeah.
I wanted to throw this in here.
A person I know did a webinar or not?
No, it was a, it was an in-person
event called Income Tax for Weirdos.
I, I totally stole that.
And I told her I was gonna steal.
I'm like, can I steal
that "for weirdos" thing?
Because that just sums up my audience.
But one of the things she said
was, keep track of your mileage.
Don't make it up.
Right.
If you
Michael Perry (Mike): right.
Timothy Iseler: you know, you might
get away with it this year and next
year and the year after, but at some
point if you don't have the evidence...
and she said, just keep a piece of paper
your glove box and every time you're
taking a trip for work, just pull it out
right down the mileage, put it back in.
And it's, it can be that low
tech of just a notebook or a
piece of paper in your car.
like you said, if you have that paper
trail, everything is above board and
you can tell your CPA, just go nuts.
Every deduction you can find, do it.
Michael Perry (Mike): I think the, yeah,
like for my mileage, I used to do, you
know, had the thing in the car and stuff.
Well, now QuickBooks just has a mileage
tracker and you can do an automatic
one, but I don't, I don't like that
because you're, it's just tracking you.
And it's also, I remember to turn it on
and, but what I do is when I get home,
I did it this morning 'cause I, I'm
actually not home and I, I went to the
Minneapolis airport to get where I am now.
This morning I went into QuickBooks,
opened the mileage thing, and I put
down the mileage from my house to the
shuttle, because I'm out here on business.
And so, I, I just wrote it down
and a quick little note about where
I was going and what I was doing.
It took me less than 15 seconds probably.
That stuff really adds up.
Timothy Iseler: Like to tell this
to people, just there's, this is
like just a little PSA that when
people ask me about taxes, like I
had to learn a lot about taxes to get
licensed to do the job I do, and to
become a certified financial planner.
But I'm not authorized to
represent anyone in tax court.
Okay.
That your CPA is authorized to
represent you in tax court, and any
question about is this legal and your
CPA should be the person you go to.
That's to say like, I want to do this.
Can I do this?
And they'll tell you like, yes,
that is either legal under tax
code or not legal under tax code.
But yeah, you shouldn't anyone else,
your financial advisor, your friend,
anyone else, you should not trust what
they say as being word of the law.
Michael Perry (Mike): The other thing
that I've found that accountants
or CPA does for me is just...
So I did, I'm, I, I mentioned
before that I'm super conscientious,
or at least I try to be.
And I did a gig in, in Montana one
time and I sold probably $72 worth of
merch, but I reported it and I paid
my Montana sales tax that, whatever
it was, it, like $3 or something.
But I, I reported it very conscientiously.
A year later I received an email from the
mon, the Montana, IRS, whoever they are.
And they said that I had not paid
my sales taxes for that year,
and therefore they were forced to
estimate what I owed the state.
And they estimated that
I had generated $1.67
million sales in Montana that year.
And there was this whopping tax bill.
Well, I just went ice cold.
And, but then of course I, I immediately
called my accountant and he just said,
just send me a copy of the letter.
I'll take care of it.
And within 24 hours, it's all done.
It's gone.
It's, whereas I would've
just freaked out for a week.
I'd have made all kinds of calls.
I've been on hold, I've been, and so
there are, there are a little benefits
to having someone professionally as well.
Timothy Iseler: Yeah, yeah, yeah, exactly.
Can you give an example of someone
or something that provided you with a
little inspiration to keep betting on
yourself when there was maybe not the,
not the tangible evidence that you should
keep doing that because you did have
that nursing license in your pocket.
At some point you had to make that
decision of like, yep, one more, one
more day, one more month, one more year.
Michael Perry (Mike): Yeah, I
can think of the, I can see the
moment with absolute clarity.
It was my grandfather.
My grandfather grew up dirt poor,
lived in a box car, moved all over
the country, wound up in the Navy
in World War ii, went ashore in Iwo
jima was in the worst of the worst.
Came back home, wound up working
for national Presto Industries.
So if you ever used a fry baby or a
fry daddy, or he was part of that.
And he, he rose to, well, there's two
interesting things that I'm reminded of
that affected my career with my grandpa.
He rose to, he was in charge of
national sales and became not wealthy,
successful, but very stable, well
off, you know, squarely upper middle
class They tried to promote him above
where he was and he said he declined.
He said, I like what I'm doing.
I'm good at my, what I'm doing.
And I remember later I was too young to
realize at the time, but he had a book
called The Peter Principle beside his bed.
And if you know what the Peter principle
is, it's that people tend to get promoted
one level above their area of competence.
And I think he just kind of thought,
you know, I'm where I need to be.
So that was an important lesson
because there are times when I've been
encouraged to reach for something where
the payoff could be good, but I also
just, I just don't feel right about it.
And I think of my grandpa and going,
he had a rich, wonderful life and
he, because he didn scratch and
claw for everything, which kind
of goes against the American way.
But the moment that I remember with
great clarity is that I had, I had
gotten my nursing license, I was
working as a nurse making decent,
I mean, good money for a single guy
in Wisconsin working as a nurse.
My mother was a nurse.
It meant a lot to her that I was a nurse.
My father is a very practical farmer,
with not a lot of patience for you
know, a guy quitting and going off to
pursue a career in the so-called arts.
But my grandpa, I remember standing in
his yard and saying, grandpa, I'm thinking
about quitting nursing and, and quitting
my regular job and going to be a writer.
And he, I just remember him just
very matter of fact, this guy who
had lived through so many things,
just saying, "there'd never be a
better time for you to do this."
And so he, that was the moment where
someone just gave me permission
to, to go ahead and do that.
Someone who was eminently sensible,
Eminently ethical and moral and
upstanding and sensible, said,
yeah, go do the crazy thing.
Timothy Iseler: Yeah.
I correct, did I understand
this correctly from your book?
That your dad started that farm,
it wasn't a family farm or was it,
Michael Perry (Mike): Well
it was a farm, but it was not
a a, it wasn't a dairy farm.
And my dad was a city kid.
Yeah, a city.
Timothy Iseler: that's what I
Michael Perry (Mike): Yeah.
Timothy Iseler: background
was not farming.
Michael Perry (Mike): Right.
He was a city kid with a,
with a chemistry degree.
But he and my mom.
All her life from the time she was
a little girl through high school
into college said she didn't care.
She too was from the city.
She said she didn't care who she married
as long as she didn't marry a farmer.
She married my father, a city kid with
a chemist, chemical engineering degree,
who about two years into the marriage,
decided he wanted to be a farmer.
Now as it turns out, she loved the farm.
She was, she, she died in our
farmhouse, the one I grew up in.
And that's where she wanted to be.
So the story had, despite the fact
that she didn't wanna marry a farmer,
she wound up in a place she loved.
But yeah, he, he didn't know
what he was doing, frankly.
And he bought this farm.
And what was neat was, this was still
back when you could kind of make it on
a small family farm, but the old timers,
and I, I referred to this a little
earlier, the old timers told him, you milk
cows, you log and you raise some sheep.
And as I said earlier in, in our
interview, that those were, that
was multiple revenue streams.
They just wouldn't call it that.
And so that was very helpful to me
to watch how dad went about things.
The other thing I learned from my dad
is that whole just keep shoveling thing.
You know, in one of my books I say
people ask, well, how did a kid with
no writing degree from rural Wisconsin
make a living as a freelance writer?
And I just say, I learned
everything you ever needed to know
from cleaning dad's calf pens.
You just keep shoveling till you got a
pile so big that someone has to notice.
And you don't wait for applause.
You just, you just do the work.
And so between that, that work ethic
thing, and then also just watching how
he didn't rely on one single thing.
That's why when I was starting
out, as I said, I wrote used car
radio scripts, radio ad scripts.
I wrote brochures.
I edited things.
I helped people with PhD papers and
things like that, whatever it took out.
I also wrote heartfelt awful
poetry and did open mic poetry
readings, and it was all part of
this wonderful learning process.
Timothy Iseler: Yeah, , I have a few
tangents I want to go on related to this.
The first is just to share like a
little bit of my background, which
is that I also grew up on a farm.
My dad grew up on a farm and the way
he grew up was much more like how you
describe where they had, they had cows,
but they also raised different animals.
At one point they had mink, they
raised mink so they could sell
the pelts and things like that.
So he grew up very much in
that sort of what we think of
as like a small family farm.
And then when I grew up,
it was just a dairy farm.
It was owned by my dad
and some of his brothers.
And one thing that I think seeped
through to me, even though it was
clear to me fairly young that I didn't
want to be a farmer, was that having
your own independence was valuable
if you still had to go to work.
So I wanna, I wanna put that out there.
But before I get any further, this
comes up with me all the time.
When I grew up, I felt like
there was no choice, right?
Like the cows get out, it's
the middle of the night, you
get up, you go chase the cows.
You know, there is no choice and down to
like, this is the food we have for dinner.
There's no other dinner.
If you don't like this, this is the food.
And that, that kind of a has really
helped me a lot kind of every
iteration of my life of just like,
this is the work that there is to do.
You just have to do it because
there's not another thing.
And then the piece of the independence,
like it's, for whatever reason, it's
very important to me to be independent.
And it's not often easier
to be independent, but it
is rewarding in its own way.
So that's sort of like, some
things that you were saying coming
to me and I wanted to get your,
your, reflect that back to see if
Michael Perry (Mike): Yes.
Timothy Iseler: any
Michael Perry (Mike): Um, make
sure you bring me back to that.
Um, just wanna quickly say, you did remind
me though of one other thing my father
taught me on how to survive as a writer.
One other thing my dad did was he stayed
small, he bought old equipment, and he'd
never got in over his head with debt.
And of course, that's what killed
most of the farmers around us.
And that's not a moral judgment, that's
just, you know, they were forced into a
system and he was able to do avoid that.
He also had a chemistry degree and he
took on some part-time work outside
of the farm where he was making
probably decent money for that area.
So I do get asked sometimes,
what's the secret to making a
living as a freelance artist?
And I say low overhead.
Timothy Iseler: Yeah.
Yeah.
Yeah.
Michael Perry (Mike): and, and it's
kind of a joke, but not really.
And it's, again, I keep feeling the
need to say, I'm also privileged.
You're privileged, I'm privileged to
even have nothing and low overhead.
So I realize most, some, a lot of people.
Don't arrive at the scene
even with that privilege.
But yeah, the low
overhead was a big thing.
The independence thing, that's absolutely
part of why my dad was farming.
He wanted to live a
life that was different.
He didn't, he didn't dislike having
a boss, but it wasn't his dream gig.
And I remember sitting
around with a young musician.
I learned so much from musicians because
I wrote about them, I went on tour
with them, I observed what happened
to their industry and it really helped
me prepare for my own career, even
though I wasn't a musician per se.
But I remember sitting around with a
young musician one time who was trying to
decide, you know, what he should do next.
And he was going through some
turmoil because he was pondering
making some big changes.
And, and I remember working with him
one day and he, he, he was kind of
being a little unhappy and I just
said, dude, you understand what we're
doing here is we're staying, we're
keeping ourselves out of the cube.
Timothy Iseler: Hmm.
Michael Perry (Mike): And I said,
we're not in the cube today, are we?
We're, we're in this cool studio.
And yes, things are uncertain, but
we're free and we're doing our thing.
And so I always think of it in those
terms, you know, keeping, keeping yourself
out of the cube and you're willing to
take some risk and it may not pay off.
But, so that's my reflection on that
is that yes, I, I joke that I'm just
terminally unemployable is what it is.
I just, even when I worked as a nurse,
I really enjoyed the work, but man,
even on days when I don't know where
the next check is coming from, I'm
happy that it's up to me to find it.
Timothy Iseler: just talking the other
day with my wife about this of like, I
realized at some point in my life that
if I was gonna complain about how people
one rung up from me were making all the
bad decisions, like I ought to figure
out how to make the decisions myself.
And that's really that point
in my career, that's when I
started being a tour manager.
I was on tour running audio for bands,
but I used to always, I had this
terrible affliction where I was smarter
than the tour manager all the time.
And, and I, it just hit me.
I was like, if I'm gonna complain
about all this stuff, I ought to
figure out how to do it for myself.
And you learn really quickly that
when you're at the top, like you
get to make all the decisions, but
then you get, you also get all the
blame and you get all the complaints,
and you get all the everything.
So I, I kind of, in this new career, this
new life that I have, get to be the boss.
And there's nobody to complain to me.
'cause I have a one person shop, but like
I get all of the freedom and I get all
of the responsibility at the same time.
And that's been one thing that's been
really helpful for me in this new chapter
is to keep reminding myself that it...
i'll just to clue you in, like,
I launched my business six
months before the pandemic.
So like my first two
years were very, very bad.
And the thing that I kept coming back to
is like I also have this amazing autonomy
that I wouldn't have if I had a more
secure job where if I don't have any
meetings and it's a beautiful day and I
want to be in the garden, I can do that.
That's available to me always.
And that is worth...
in a lot of ways, that's
worth more than money.
And just keep reminding myself that
independence matters in a lot of ways.
Michael Perry (Mike): Yeah, and
I can speak to the, you know,
the pandemic thing you mentioned.
There's another thing that reminds
me about autonomy, but also survival.
So I still, I have a contract
right now with Harper Collins for
a book, and I have a contract with
another legacy publisher for a book.
But when the pandemic
hit, it was the same deal.
It was about half of my income comes from
live performance speaking and one man
shows and stuff derived from the books.
You know, that, as you know, that stopped.
And I know many musician friends
who everything just came to
a complete and utter halt.
And one of the things that I did is I
started to get back into self-publishing.
And there's a stigma attached to
some self-publishing because it's
often associated with vanity presses.
And, but honestly, having again watched
my musician friends, we have tools
now, and that means we have options.
And I have certain types of writing.
Like I wrote a newspaper
column for almost 10 years.
Well, Harper, I'm not famous
enough for big enough that Harper
Collins has any interest in doing
a, a, a collection of my columns.
But I have my own mailing list and I
have enough people on that mailing list
that I know they'll, a certain percentage
of them will buy that collection.
And so we, we pivoted uh, I hate to say
pivot 'cause that just sounds, we put a
pin in it and we'll circle back and pivot.
anyway, we just, I told my and
my manager, I said, we're just
gonna publish these columns.
Gonna get 'em together
and, and, and put 'em out.
And that's another example
of, it's a combination of work
ethic, but it's also survival.
It's perseverance and it's also freedom.
It, I didn't have to wait for the
New York City publisher to take
me through the whole process and
negotiate and do all this stuff.
And by the way, get six to 12%
every six months hoping that the
accounting was somehow accurate.
We literally self-published
within a couple of months.
We had a product out and it
was a product we're proud of
that we're, we're happy with.
And it spackled the gaps,
as I always like to say.
It got us through that stretch.
The other thing I should mention
is when I say that, you know,
when, when COVID hit, it absolutely
made a huge impact on our income.
The one thing I wanna say is that,
having said that, I wasn't as scared
as I would've been 20 years earlier
because we've just been slowly
putting money away and investing
and just there's a long stretch
where you feel like it's not worth it.
Timothy Iseler: Right,
Michael Perry (Mike): then you hit a point
where you go, am I ever glad I did this?
Timothy Iseler: right.
Michael Perry (Mike): one of the things
that's really helped me is that for
whatever reason, I'm no financial genius
guy, and I'm filled with anxiety and
dread and sort of manic depressive like
a lot of artistic folks, but one thing
that I've been just rock solid ice cold
on is if the market goes down 25%, I
don't give a rip because I've lived
through three of those now, and each
time it's been breathtaking, but each
time within a year to four, five years,
you're just like, well, thank goodness
I didn't freak out and yank everything
Timothy Iseler: right.
Michael Perry (Mike):
we'd be starting all over.
So that let's just, if I give one piece
of concrete advice today, that's it.
The other thing was about the
appreciation of the independence.
I think the one thing I, I always
am careful not to overdo the whole
by gosh blue collar background, grew
up eating some government cheese.
It's all true.
But I know plenty of people who
grew up in those circumstances
and are also ungrateful.
And I know plenty of very wealthy
people are trust fund people
who are gracious and thoughtful
and acknowledge their privilege.
But having said that, I
do remember one time...
one of the things I like about having this
background is that, you know, my brother's
a logger and I remember I was out on book
tour and I was in San Francisco and they,
and they had put me in the Cliff Hotel.
I mean, I didn't even know
how to use the silverware.
And I was doing this event with a very
prominent New York based, very privileged
novelist, no names still out there.
And we were at this event in the
green room and there was this spread,
like chocolate covered strawberries
and what you name it, right?
And, and this guy's sitting there and
he goes, what do you think of your room?
I said, well, it's amazing.
And he goes, yeah, I don't,
I don't really like my room.
He goes, and this food, he goes, and
I was like, dude, in Wisconsin, it's
20 below and my brother is logging.
Timothy Iseler: Yeah,
Michael Perry (Mike): I think we're fine.
I'm gonna go ahead and have a
chocolate covered strawberry.
Timothy Iseler: yeah, yeah.
Michael Perry (Mike): So I think there
is that, if you can realize what I,
what I realize that my brother likes
logging, but I, I realize the privilege
in being there may be uncertainty
in what I do, but there's a lot
of uncertainty in logging as well.
Timothy Iseler: That's right.
That's something I say also...
you can make every safe choice, not that
logging is a safe choice, but you can make
every safe, conventional, conservative
choice about your career, your money.
Your life, everything.
And it can still go wrong.
People still get divorces.
People die, the homes burn, like
everything can still go wrong.
Michael Perry (Mike): There's, so
you've made me think of two things.
Number one, that that's why
I never get cocky about this.
And I, again, I keep saying
asterisks on everything I say,
everything could go wrong tomorrow.
You know, uh, for instance, we
are one of those families that's
very vulnerable to a major health
issue with the way things are.
I don't need to explain
how our health system is.
But, but one of the things
that you just reminded me of
is the advantage of this life.
I remember, was it 2008, as they
say in financial circus circles.
Circus works too.
The GFC, the great
financial crisis of 2008.
And it was really bad, but I remember
having a conversation, it was the
first time I, that I'd been through
something that big, And I was talking
to a buddy of mine who, of all things
installs, alternative energy systems,
and he's been self-employed forever.
And we're like, everyone was
freaking out and everything.
And I remember he and I just
going, how are, how are you doing?
We're going, I don't know.
Doing all right.
And we both realized that being
self-employed for this long, he
and a pretty standard business, me,
as an artist, you learn to surf.
You, you, you don't count on anything.
You've never had a paycheck
coming in every two weeks.
And so again, please, this is not
being said with an air of superiority.
It's just saying there, the built-in
advantage to being a self-employed
artist is you, you're surfing every day.
Timothy Iseler: Mm-hmm.
Michael Perry (Mike): watching
for the waves every day.
And so when the big stuff hits,
you're already kind of pretty, I
dunno if you're comfortable on your
board, but you know how to pick it.
Timothy Iseler: Yeah.
Yeah, yeah, yeah.
I wanted to circle back to this so we
don't forget, is the thing that you
were mentioning of how you started
investing when you sort of made a
joke about a mutual fund and then,
you know, for a long time it kind of
didn't matter, and then at some point
you were like, oh, it matters now.
Right.
Michael Perry (Mike): Yeah.
Timothy Iseler: that is a tricky
thing I, it's, it's not just
tricky in like, some people think
the stock market is risky, right?
It's tricky in the sense
that of like evolution.
Like we evolved to be really good at
making judgements on linear equations.
Like how fast is that thing
running and can I run faster?
That's a linear equation.
But the way that investment works or
the way that interest on debt works,
is it compounds, it's exponential.
And humans are really bad at
thinking in those terms, even when
they understand what it means.
And so if you're investing, like let's
say just putting money a hundred bucks
a month into an account for a long time,
it doesn't look like much of anything.
But then if you can wait and you
can wait, then it's, you know, that
little bit that it goes up every
year, it really kind of snowballs.
Michael Perry (Mike): Being patient
and, and not thinking you're that smart.
So here's what I'll say.
Timothy Iseler: There you go.
Michael Perry (Mike): My investing,
as I said early on was that a
thousand dollars in sometime in
the nineties, and it went into some
very mundane vanilla mutual fund.
And then I really didn't have anything
to invest probably for several years.
And then over time, a little
bit more here and there.
And then at some point I went to some
very general, one of these companies
you'll see advertised that, you know,
I, I'm trying not to name anybody, but.
You know, I got a rep and they're fine.
And, and you'll, you're always gonna have
someone who says, oh, they're working
on commission and they're doing this,
and they're doing that, and they don't.
I'm like, I understand,
but, you know, at my level.
Well, then I got to a point where
I had enough that I, I had it
spread out a few too many places,
so I wanted to consolidate.
And then there was, and I'll just
be very frank about this, there
was a financial advisor that I
happen to know is very trustworthy.
He, he works with some big
business people I know.
And it's one of those places where
you can't get in the door unless
you have a certain amount of money.
And we were near that.
But he liked my books.
Oh, we'll be at, we'll take you on.
You know, so, so I do have, the
bulk of our stuff is with, you
know, someone who's looking it over.
And I like that.
I want someone independent of my
emotions looking over and who can
make some general projections.
But the, the counter to that is I also do
have, I have a little Robinhood account
and I have a little E-Trade account.
I throw a little money in there now
and then, and when I read something
where I think that it's really gonna
go, I allow myself to buy some.
And then about once a year I compare
how much money, what percent might
Robinhood and E-Trade accounts are
compared to what my very middle
of the road 25 years is doing.
And of course, I'm an idiot.
You know, I don't, I can't even come close
to the performance of the boring stuff.
And so I think it's okay if, if you
hit a point where you have a little
bit of that extra money to, to go ahead
and have your little account where you
make all your wise smart insider info
investments, usually about one stock,
you know, one share or something small.
And it's just this little
reminder for me that yeah, you
really need to just step aside.
Timothy Iseler: Yeah.
Michael Perry (Mike): Yeah.
Timothy Iseler: the statistic, which is.
Essentially unchanged every single
year that 85% of professional fund
managers, active fund managers, I
should say, where they're, they're
not just following an index.
They're trading in and out of stocks
or bonds or whatever, that 85%
of the professional fund managers
underperform their benchmark.
And so I, I am totally on board with you.
Like I, I think the best that I can
do is park my money somewhere where
I can essentially stay forever.
But I also like saying like,
I believe in this company.
I'm gonna buy some individual shares.
Right?
I do both.
But the, the idea that somehow,
because I've got a good feeling I'm
Michael Perry (Mike): Yeah.
Timothy Iseler: you know, all of
these professionals who can't.
And, and there's not dumb people.
They're smart people who spend
their whole lives trying to do it.
It's just that it's really hard to do
the same way that it's really hard.
To be on a, on a an NB, A
team that wins the finals.
Like it's very hard.
Even if you're a top elite,
you're probably not gonna
be on that team this year.
Michael Perry (Mike):
Yeah, no, it's, it's good.
I think my, I think my E-Trade
account is currently, I haven't
made some something like, uh, 0.7%
over the last 15 years, you
know, and you go, oh, yeah.
I'm definitely the guy that, that
has the inside track on this.
Timothy Iseler: yeah,
Michael Perry (Mike): I think it, it's
okay in the sense too, though, like
if you do hear like, well, I bought
some Bitcoin just because I was like,
well, I'm gonna buy a very small
amount, and if for some reason it goes
to the moon forever, well then fine.
And I won't feel like I missed out.
But I also, I heard you in another podcast
advising someone on this like, but it's
not the place to take your family savings.
Timothy Iseler: Right, Right, totally.
I did the same thing, uh, what was it?
It was 2017 or 2018.
And it was, it was still pretty
niche, but not that niche.
And I
Michael Perry (Mike): Right.
Timothy Iseler: I'll, I'll
take a thousand dollars
Michael Perry (Mike): Yeah,
Timothy Iseler: and if it goes
to zero, then whoops, like...
that.
That's, I I wanna be clear,
like a thousand dollars is
an expensive mistake for me.
You know, I'm not,
Michael Perry (Mike): yeah,
Timothy Iseler: I'm not comfortable
making a thousand dollar mistakes often,
but I was like, I'm just gonna see,
Michael Perry (Mike): yeah,
Timothy Iseler: I check
that account twice a year
Michael Perry (Mike): yeah.
Timothy Iseler: and it's up.
But like, I'm not, I'm not
banking my future on that.
I'm just
Michael Perry (Mike): Yeah.
Timothy Iseler: if it works, that's cool.
And I also know that I have a high risk
tolerance for those kinds of things.
So if, you know, for some people
the idea of making an investment
that goes to zero is terrifying,
so if that's, you don't do it.
Michael Perry (Mike): I, I have
a, you know, I did ask, I remember
asking a computer buddy of mine back
when Bitcoin, I was like, think $12.
What is this Bitcoin thing?
I'm kind of thinking about getting some.
And he said, I don't understand it and
I don't buy things I don't understand.
So I let it go and,
Timothy Iseler: Yeah.
Michael Perry (Mike): then I bought, like
bought the same as you very, you know,
modest amount when it was mid-range.
And it, whenever I feel bad about not
buying the $10 Bitcoin, I just think
of another friend I have who was in
Seattle and kind of hip to the whole
thing and he bought Bitcoin at 10 or
$12 and put it on a flash drive and
Timothy Iseler: I lost it.
Michael Perry (Mike): The flash drive.
So I go, I may regret not getting
in at the floor, but at least I
don't regret getting in on the floor
and then losing the flash drive.
Oh, gosh.
Yeah.
Timothy Iseler: you mentioned earlier
that you, you've kept your overhead low.
What are, well, what's one other
thing that you think you do
well in your personal finances?
Michael Perry (Mike): Boy,
I don't, I don't know.
I, I, I have hit that point where, you
know, you read the things about if you're
poor, if you're still struggling, you're
trying to build, you know, you shouldn't
be buying a $5 cup of coffee at Starbucks.
I'm kind of a, there's a guy named Nick
Maggiulli, maybe you've read him and
I've kind of agree with him where he is
like, you're, you're not staying poor
because you're buying a $5 cup of coffee.
It's like you do have
to, you do have to live.
And I'm, the $5 cup of coffee's
a bad example because that means
more to some people than others.
But it's more about the long-term
things we've been talking about.
And so I will say that in the past
few years, I have gotten to the
point where if, if I think something
is a is val of value or quality,
I'll go ahead and spend some money.
And then also, I'm not really
answering your question.
I, I mean, the low
overhead is a big thing.
I think also I, I, I remember not buying
a house for a long time and then when
I did, I wished I'd had done it sooner.
Now that's a, that's become a
little trickier, keeping in mind,
I bought my first house probably
25 years ago and had very, as I
said, $160 a month house payments.
'cause I, it was in northern Wisconsin in
a place where not many people wanna live.
But that is another thing that we haven't
talked about is that because of how,
because of the low overhead, I was able
to do some investing, but also, you
know, I bought that first house and then
I was able to buy a little bit of land.
And then, and then when I got
married, we bought a house and we
have some land now and we've dutifully
kept paying that down and down.
And having that, that land, like I
always think of, this is very amateur
of me, but as a self-employed artist,
we have three legs on our little
financial stool and one is the investing.
The other is we do keep probably
a little more cash on hand than a
financial investor would advise.
But I don't care because to
me, that's about sleeping.
Timothy Iseler: Yeah.
Michael Perry (Mike): go to bed at
night and know that if I don't wake
up, my wife and daughters are, they,
they have out, they're not fine, but
they have what I call a glide path.
Timothy Iseler: Mm-hmm.
Michael Perry (Mike): They don't have to
make critical decisions in 20 minutes.
And then the third thing is that I, I
have always, because of starting out
with a very cheap house in a place that
wasn't that popular, and then I bought
a little bit of land with one part of
an advance I got once and then turned
around and flipped it without trying.
I did.
That was not my intent.
I just wanted a place
to put my deer stand.
But then some guy from Minneapolis saw
it and offered me too much money for it.
And then.
So like now we have a modest, at least
where we're from, you know, we have, we
live in an old falling down farmhouse
that really needs to be torn down, but
it's attached to 37 acres, and that is
something that I will hang onto as long
as I can because it's the third stool.
It's this thing that has, it's not liquid,
Timothy Iseler: Mm-hmm.
Michael Perry (Mike): turn it into
cash tomorrow, but it's near a, a city
of about 60 to 70,000 that's growing.
It's beautiful land in the hills, and
we know that if push comes to shove
and we're in a bind, we can unload
that and that is not gonna lose value.
That's another, I guess, form
of diversification, just trying
to have those three things.
If, if, if you're listening to
this and you're just starting
out and you can't even imagine,
please understand, man, I had...
i'm nothing.
And this, this has been so incremental.
Timothy Iseler: right.
Michael Perry (Mike): I'm, I'm 60,
so this has been super incremental.
And I, and the other thing is that, and
I'm so fortunate, here's a bit of advice.
My wife and I, we've
been married 21 years.
I got married late, but
we've been married 21 years.
And it's like any marriage, we have to
work on it and not every day is daffodils.
But the one thing that we have
agreed on from day one is money.
Timothy Iseler: Hmm.
Michael Perry (Mike): She came from
a very tough farm, rural background.
And we are both frugal.
Not in it.
We don't, we both believe in
travel, like our children.
We, we spent money to travel.
We spent money to go to rural
Panama so our kids could see other,
that to us had a, had a value.
But to be in a relationship with someone
where you might have disagreements about a
ton of things, and my wife and I don't see
everything the same, but on finances...
rock solid.
And I believe you'll back me up on
this, that's like one of the top causes
of relationship issues is finances.
You, you wanna think it's
love, it's it's money.
Timothy Iseler: Yeah.
Michael Perry (Mike): And so I
have a wonderful partner in that
she's willing to live in a house.
You know, we're at the point where
we gotta do something, but she's
willing to live in that house.
She's, we buy used cars 'cause
we don't feel the need to be
seen in some fancy vehicle.
And I'm, the reason I'm bringing this
stuff up is to circle back again,
if you're listening to this and you
don't have, you're starting out and
you can't imagine owning 37 acres.
Dude, I, I, I couldn't
have either back then.
And I'm not a wealth, we're not wealthy,
but, but we have built a comfort zone.
Timothy Iseler: Yeah.
Yeah, yeah.
You are 100% correct about, I, I
don't have a statistic to back it up,
but like the financial difficulty in
the home being one of the number one
things that causes trouble in couples.
It reminds me of this
thing, which is like...
gosh, how do I wanna say this?
That people tend to think that money is
math, and that if you get the numbers
right, you can unlock it somehow.
But in almost every way, money is much
more like politics or religion, where it's
like, it's a belief and you believe if you
have money or whatever, you think having
money makes you one kind of a person.
That's a belief that's not a function
of the numbers adding up because
there's lots of people that have
lots of money who are unhappy.
There's lots of people that don't have
much money at all, who are plenty happy.
So like in terms of a relationship,
it really is the same as, or, or very,
very similar to like, if people have
different political beliefs and they're
trying to convince the other one that
they're wrong, like it won't work.
It's not fact, it's belief.
Michael Perry (Mike): We've both lived.
I know a little bit about your background.
We both know folks who, artists
who have become Grammy winning
famous, made millions of dollars.
And it sounds cliche, but
the troubles don't go away.
Timothy Iseler: Right.
Michael Perry (Mike): There are a lot of
problems that you can solve with money.
Let's not fool ourselves.
Timothy Iseler: Right.
Michael Perry (Mike): And as I said
earlier in the interview, I'm more
than happy to deal with the problems
that come from having millions of
dollars so far, haven't gotta do that.
But it's, it's not just a cliche, it it,
that is not where your happiness lies.
You know, the other thing I was thinking
about, this is tangential, but one of
the things that helps me too is that,
yes, I've made it to the point where
we have what I call the glide path.
We do have savings and investments.
We do have 37 acres.
But you know what, I had a gig last week.
And I drove, took my turn driving
the van and I was up in my little
room above the garage, that's my
office with the old school cash box,
counting out the cash, doing the
QuickBooks, doing the merch sales.
And, and two things come to mind.
One is it's a great time to be an
independent artist in that here we
were in the middle of nowhere doing a
show with, you know, taking people's
credit cards and tapping their phones.
So, you know, we can do business
in places and in ways...
I remember when I got my first old
credit card swiper, the clunk, clunk
thing with, and yet send in the
carbon copies and wait for the money.
So we have all these wonderful tools,
but I'm still grateful that even though
I may have 37 acres and some savings.
I still see the money come through
and I have to keep track of it.
And I know if that, you know, our merch
sales at this last gig were low enough,
but they were enough to cover the merch
sales, pay the person who does the merch,
and we made a little bit of profit.
So it's like, well, okay.
And then I think having some sort
of, again, this is getting back to,
do you want to be a pure artist who
never thinks about these things?
In my case, I prefer to literally
count out the cash and take it to the
bank and to do the QuickBooks so that
I know that no, this is, we're okay.
I can go, I can take tomorrow and
write and, and create some more things.
That, that tangible connection to
the business side of your art, I
think in my case, only energizes me
Timothy Iseler: Mm-hmm.
Michael Perry (Mike): to keep at it.
Timothy Iseler: Yeah.
Yeah.
That's a theme that I've heard in a
few different private conversations
and, and sometimes on the show is.
I think there's a feeling that if you
get, is gonna sound weird, but get really
into your money, in the sense of like
get really on top of managing your money,
that somehow it becomes consuming, it
becomes your life to always pay attention.
And it does the opposite.
It takes away all this ambient
stress because you know the
reality of the situation.
And if you're okay, then it's like, all
right, I don't have to worry about that.
Michael Perry (Mike): Plus, I
think again, this gets back to...
I had a friend who became very successful
in the music business and I had had
some very, very modest success with
my first book at that point, enough
that I needed to get an accountant
and I told this person, I said, man,
you, you know, you've, now you've
hit a level and you're headed for a
level that I I'm of no use to you.
You're getting way bigger than
anything I've ever dealt with.
But I had spent a lot of time with country
musicians, including some really well
known ones, and studied them and wrote
about them and watched them in action.
And I said, the best advice I can
give you at this point is just get
someone to do the grownup work.
And that is get you a good
accountant and a good lawyer.
And I said, because I said, and this,
let me be clear, this was a joke, but
I said, we can get you outta rehab, but
I can't get you outta federal prison.
Timothy Iseler: Right, right, right.
Yeah.
Michael Perry (Mike): Oh yeah.
So, and, and the, the
circle back there is.
Ultimately it's peace of mind.
It gives me, I don't count that money
'cause I'm going, how much did we make?
Are we, am I gonna get rich?
I'm going, okay, I know where we're at.
I know exactly what the numbers
are going forward tomorrow and
now I can quit thinking about
that and go back to writing an, an
introspective essay, believe it or not.
Timothy Iseler: That's great.
Mike, I finish up every show
with a question from my guest.
Yours was regular IRA, Roth IRA or SIMPLE.
Michael Perry (Mike): Well I'm
never, it's, it's always confusing.
So because we have an S corp,
Timothy Iseler: Right,
Michael Perry (Mike): do have a SIMPLE,
Timothy Iseler: right.
Okay.
Michael Perry (Mike): and the
advantage to you artists out there
of having a SIMPLE is you can, unless
I'm completely misinterpreting it,
you can plow a lot more in there.
And then also the advantage to becoming 60
as you get older, they let you put in more
Timothy Iseler: let you put in more.
Yeah.
Michael Perry (Mike): the
old catch-up as they call it.
Timothy Iseler: Yeah.
I.
Michael Perry (Mike): of course,
from way back I have some Roths
and I have some regulars, and then
my wife too has a couple of those.
So I'm always, maybe it's just
an excuse for you to explain
the cons and the differences.
I'm also always wondering about converting
Timothy Iseler: Yeah, well, as
long as you're still self-employed,
you should keep that SIMPLE.
Michael Perry (Mike): Yes.
Timothy Iseler: there's an so a SIMPLE
IRA, it's, you can think of it as
sitting somewhere between a 401k, which
is very complicated and requires a
lot of paperwork, a lot of overhead,
a regular IRA, which is owned by
an individual and is not related to
your employer, but controlled by you.
So a SIMPLE is an employer sponsored plan.
It's less paperwork a 401k.
It allows you to put in a lower
total maximum contribution, but
it also is just much easier.
There's also a thing called
a SEP IRA, which is also a
very easy thing to implement.
It's got even fewer
regulations than a SIMPLE.
So that's just to give some context,
the SIMPLE is related to employment,
and if you're self-employed, it's
the kind of thing that you can do.
So with a regular IRA, what might be
called traditional IRA, what happens is
the amount that you contribute reduces
your taxable income for that year.
That's the plus.
The downside is that whenever you
take the money out, there's taxes
owed on all of it, regardless of
what your original contribution is.
So you, you save on taxes,
now you pay taxes later.
With a Roth IRA, you don't get
any tax break when you contribute,
but then when you take the money
out later, it's all tax free.
So all of the growth is tax free.
And a SIMPLE, with very few exceptions,
I don't think you can do a Roth simple.
I think it has to be traditional,
so it reduces your taxable income.
And the reason that something like that,
or a SEP IRA or even a solo 401k is good
for a self-employed person that when you
are both employer and employee, those
accounts let you put in a lot more money.
So on those years where your business
is doing fantastic, you can take a
bigger part of your income income
and transfer it to yourself and
have no current year income tax.
And of course the downside that
you have to pay taxes later.
So if you're balancing these things,
the way to do it would be so that.
In the future, when you start
drawing down those accounts, you
can plan on the tax consequence.
know, you can sort of decide this
year, this is how big of a tax
consequence I want because this
is how much I'm gonna take out.
all that make sense?
Michael Perry (Mike): Yep.
You mentioned the, the other thing
about the SIMPLE, if I understand
it right, the nice thing there too
is that there's an employer match.
Timothy Iseler: Right,
Michael Perry (Mike): And so if you own
the company, the employer match is you.
And so you're actually paying
in two ways completely.
Again, legally above
board within the rule.
Timothy Iseler: Yep.
You have an S-corp.
So then you also have this extra
distinction where some of your
money is compensation and you owe
employment tax, and when you have an
S corp that's FICA, and some of that
money flows through and skips that.
So you're getting a lot
of tax advantages there.
And I, I, and I should also clarify
for all of these, there's a minimum
age that before that age, if you take
money out, there will be penalties.
So just keep that in mind.
That age is 59 and a half,
which is a stupid age.
They should make it age 60 'cause
everyone can just remember that.
But 59 and a half is the age.
If you take money out before that you, you
will owe penalties and potentially taxes.
With a Roth IRA, because the
government's never going to get
any more tax money from that, they
don't care when you take it out.
So with your Roth money, you can think
of that as basically forever money.
with your traditional accounts and
your simple, there's an age at which
you will, the government will force
you to take money out and those are
called required minimum distributions,
'cause they want their taxes.
But with that Roth, they don't care.
They're never getting that money or
they're never getting taxes on that money.
About that as is my uh, nursing home
money, or you could think about this as
like, all of this is going to the kids
and the rest of it I'm gonna spend down.
And so if you wanted, you could be
more aggressive in that account, more
conservative in your other accounts.
And, and the reason I say more aggressive
in your Roth is 'cause in theory it has a
much longer horizon, much longer timeline.
And the sooner you need your money, the
more conservative you should be with your
investments, the longer until you need
your money, the more risk you can take
because it's got more time to recover.
So that's one way to, to contextualize it.
In terms of combining accounts, this
is just my, the way I see it, I don't
necessarily believe this is right or
wrong, but it's the way I see it that
as long as you still are employed, it
makes sense to keep that SIMPLE account.
I don't personally think it makes
sense to take your traditional
IRA and roll it into your SIMPLE.
I don't think there's actually
a big advantage there.
This is something I don't know, I will
look into this and actually tag on a
note at the end, 'cause I don't know
this off the top of my head: it may
be possible that with SIMPLE accounts
they're protected from creditors
because they are employer accounts.
In which case that would mean that if you
got sued, that account would be protected,
which is not the case with an IRA,
know 4 0 1 Ks protected from creditors.
So that's one advantage there.
I will look up whether SIMPLE accounts
are protected from creditors and
I'll add a little note at the end.
Did I answer your question?
Does that help?
Michael Perry (Mike): yes, it helps.
You, you also remind me, and I'll,
I'll try to be so brief with this, but
we really started this conversation
talking about the pros and cons of
business as it relates to art and
finances, as it relates to art.
And I reiterate all the
asterisk and privileges that
I acknowledge in my situation.
But there's another reason
that I like being businesslike.
I do, I have a band and we formed a
separate LLC for the music events.
And I hire the band members as employees.
We only do 10 or 15 shows a a
year, but I hire them as employees.
And I have people constantly telling
me, pay them as subcontractors.
And I said, no, if you actually,
at least in the state of Wisconsin,
they don't qualify as subcontractors.
And also there's a, you
know, I pay workers' comp.
And when, when COVID happened,
actually one of my band members
was able to, it was an extremely
modest amount, but I just remember
going, well, this is why we do this.
But the other thing is a liability thing.
If, if, if someone falls off the
stage playing for me, I've got,
at this point in my life, I do
have things I don't wanna lose.
I'm not, I understand if you've got
nothing, you know, like I, A, I can't
afford to do it that way, and B, what
are they, how are they gonna hurt me?
But again, so much of what I do is
predicated, not on some grand theory,
but simply on what helps me sleep
at night the best and formalizing.
Portions of your art
just engenders more art.
Timothy Iseler: Mm-hmm.
Yeah.
think you, you brought up a great
point about treating people as
subcontractors versus employees.
And I actually, I know someone who
something like that happened where she
hired a contractor who then claimed
there was an injury this person thought
that claim was slightly dubious, but
because of the contractor status was
there was no workers' comp, and it
became this very complicated legal
hassle that ultimately got resolved.
But, you know, even if you have to pay
an hour a lawyer for a few hours of time
to get that resolved, it's like it's,
it's not necessarily worth the headache.
Do you think that's a
good place to wrap up?
Michael Perry (Mike): Yeah.
I think we've worn people out.
No, I really appreciate it, and
I just appreciate, you know, I do
tons of podcast interviews, but
this is one of the most unique ones
I've done in a long, long time.
And then I think it's, I, I, I hope
I've made it clear that I don't, I'm
not putting myself up as the expert,
or, and I'm also acknowledging, you
know, if you're a, a single mom trying
to, you know, make it as an artist
or a musician or if you come from
a completely different circumstance
than I did, I know that some of this
advice is superfluous and privileged.
But I also know that there are
plenty of folks out there that just
avoid it and, and don't want to
talk about it, and when in fact, it
is the one thing that can actually
help your art survive and blossom.
Timothy Iseler: Yeah.
I think that's a great
place to end it today.
Thank you so much.
I appreciate your time.
Michael Perry (Mike): Yeah, man.
My pleasure.
Timothy Iseler: My thanks to Mike
for sharing so much about his
life as a self-employed writer.
I really wanna underscore again how
important it is to at least have a basic
understanding of money and business.
If you want to work for
yourself in a creative field.
It's slightly paradoxical, but learning to
manage your money actually helps you think
about money way less because you remove
this sort of ambient stress that comes
from knowing that you should be doing
things differently but not knowing how.
And to follow up on that thing
about SIMPLE IRAs: yes, SIMPLE IRAs
are protected from creditors in
bankruptcy, but protection outside
of bankruptcy depends on state law.
And the same applies to SEP IRAs, which
is another type of employer-sponsored
retirement account that can be
great for self-employed people.
So even though the risk of bankruptcy
for most people is extremely small,
that is one upside to having those kinds
of self-employed retirement accounts.
FYI, traditional and Roth IRAs are
protected from creditors at the federal
level, but only up to a certain amount.
And of course, the treatment at
the state level varies by location.
Okay, that is it for today.
I'll be back next week
with another solo episode.
But first:
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