The Bootstrapped Founder

Few people had an impact on my founder journey as Dr. Sherry Walling — and she didn't even know. But I got to tell her! We discussed burnout, imposter syndrome, and stress among founders. Sherry explained the need for mental health professionals who understand the unique challenges of entrepreneurship and shared that burnout is a diagnosable issue. 

While entrepreneurs have more control over their work, long hours and hustle culture can still lead to burnout. Her book, "The Entrepreneur's Guide to Keeping Your Shit Together," helped me during a period of burnout while selling my business. 

Now, you get to learn from her and her deeply actionable insights into founder psychology.

00:00:00 Introduction to Sherry Walling
00:03:13 Mental health in the entrepreneur community.
00:09:17 Do entrepreneurs have control over their destiny?
00:15:22 How do you find good mastermind groups?
00:21:52 Mental health is not always called mental health
00:28:20 Grief is the emotional reaction to loss
00:34:06 You can have relationships with people who don’t get it.
00:40:24 Mental health apps are not a replacement for therapy.
00:45:59 Why aren’t more people talking about mental health?

The WIRED article about mental health apps:

My new podcast project: Arvid & Tyler Catch Up /

The blog post:
The podcast episode: 
The video:

You'll find my weekly article on my blog:

My book Zero to Sold:
My book The Embedded Entrepreneur:
My course Find Your Following:

This interview is sponsored by

Creators & Guests

Arvid Kahl
Empowering founders with kindness. Building in Public. Sold my SaaS FeedbackPanda for life-changing $ in 2019, now sharing my journey & what I learned.
Sherry Walling
Psychologist to entrepreneurs. Author 2x. Podcaster. Speaker. Advocate for psychedelic therapy. Contributor to @Entrepreneur. Lover of circus. In grief.

What is The Bootstrapped Founder?

Arvid Kahl talks about starting and bootstrapping businesses, how to build an audience, and how to build in public.

Arvid Kahl: Hello, everyone and
welcome to The Bootstrapped

Founder. My name is Arvid Kahl
and I talk about bootstrapping,

entrepreneurship and building in
public. Today, I'm talking to

Dr. Sherry Walling. She's a
speaker, author, and

psychologist. Her work had a
profound impact on my founder

journey. It was the book that I
was reading her book, The

Entrepreneur's Guide to Keeping
Your Shit Together, that really

helped me while preparing my own
business for an exit. And it

materially changed my stress and
anxiety levels for the better

after I was done reading it.
Unsurprisingly, I wanted to talk

to Sherry about mental health
topics that every founder

struggles with: burnout,
impostor syndrome and just being

stressed out of our minds. We
live through that every day.

There's a lot we have to deal
with as entrepreneurs. And it's

very useful to have a mental
health professional in our

ranks. And Sherry is that person
for so many founders. Before we

get started with a conversation
with Dr. Sherry Walling, let me

thank the sponsor for this show, Imagine this, your

founder who's built a solid SaaS
product, you acquired customers

and the products generally
consistent in its monthly

recurring revenue. The problem
is you're not growing for

whatever reason, lack of focus
or lack of skill or just plain

lack of interest and you feel
stuck. What should you do? Well,

the story that I would like to
hear is that you buckled down

and somehow reignited the fire
of get going and getting past

yourself and the cliches and
then started working on your

business rather than just in the
business. That would be great.

You start building an audience
and you move out of your comfort

zone and do sales and marketing,
all the things we don't like to

do. And in six months, you've
tripled your revenue. Well, the

reality isn't as simple as this.
Situations may be different for

every founder facing this
crossroad. But too many times

the story ends up being one of
inaction and stagnation until

the business becomes less
valuable or worse, worthless. If

you find yourself here or your
story is likely headed down a

similar road, well, let me offer
you a third option. Consider

selling your business on, capitalizing on the

value of your time is the smart
move here. is free

to list and they've helped
hundreds of founders already. So

go to and see for
yourself if this is the right

option for you. And now here is
Dr. Sherry Walling.

Awhile ago, I asked my followers
on Twitter if they ever

experienced burnout and 89% of
them said that they have been

experiencing it in the past or
that they are currently mid

burnout. That's 1 in 10 of my
audience on Twitter. And I was

extremely surprised by this. If
mental health is such an

incredibly common problem, 9 out
of 10 people experience it. Why

do we so rarely talk about it in
our communities? There's still a

taboo around it. What do you
know about this lack of

communication about this very
important topic?

Dr. Sherry Walling: I mean, I
talk about it all day, every

day. It's the thing I dug about
and there certainly are, I think

the conversation around mental
health in the entrepreneur

community has really opened up
quite a bit in the last 5 to 10

years. When I first started in
this space, in like 2015-2016,

it was really quite unusual. I
think one of the things that

makes it difficult to talk about
is that there aren't as much as

we would like there to be these
lovely clickbaity, five things

that you can do to solve
burnout, they're harder than

that. And so burnout,
prevention, burnout

identification, they're actually
sort of complicated processes.

And they don't lend themselves
super easily to a nice

clickbaity soundbite or a tweet.
So to talk about mental health

in a really meaningful way, it's
actually a pretty nuanced

conversation that sometimes
founders don't have the time and

energy for, don't make the time
and energy for.

Arvid Kahl: Yeah, I think it's a
priority problem for many

people, right? They see so many
other things that they need to

tackle that are more tangible,
maybe. Maybe solutions are more

apparent to these problems. So
they kind of dismiss the whole

conversation. It's unfortunate,
I feel. I wish people would talk

about it more and feel to be
more of a problem that they need

to actually address.

Dr. Sherry Walling: There's kind
of like a normalization of

burnout. Like you just don't
expect that if you're founder,

you're going to have burnout.
And that's not correct. And it's

actually very problematic
because burnout, which we can

get into in more detail if you
want to, but burnout, true

burnout is actually brain
damage. It's like, directly

observable on a functional MRI.
And so for us to normalize, oh,

we just do this to ourselves. We
just run our braids ragged,

that's just part of it, I think
is a pretty unacceptable way to


Arvid Kahl: Yeah, if it's
something real and that's, I

usually compare this to
something like imposter

syndrome, which isn't even a
syndrome, right? It's the

imposter phenomenon for many
people, at least apparently, in

the clinical world as much as I
know it. So that is something

that also exists, but it's by
far not as medically studied and

proven. And actually a problem
like a mental health issue as

burnout is. And I sometimes
wonder, people don't even go to

great lengths to talk to mental
health or any medical

professionals about it. They
self diagnose. That was the same

for me. Like, I think, I believe
I've experienced burnout twice

in my life. I have no medical
trail, like I never went to an

actual psychologist or just talk
to anybody in the field. I just

thought, oh, this is bad. I need
to take time away from this and

all that. So I kind of even
then, knowing that I had a

problem, I struggled to seek
medical help. Do you know why I

did that? Can you diagnose me
right now?

Dr. Sherry Walling: I do think
that people don't know that

burnout is a formal diagnoseable
problem. And I will also say

that often the psychological or
mental health community is not

super adept at dealing with
burnout. We often misdiagnose it

as depression or we often just
misdiagnose it as generalized

anxiety or something else. So I
think there's a both and problem

when it comes to really getting
good care for burnout when

people don't recognize that that
would be helpful. And two, it's

harder than it should be to find
mental health professionals or

medical professionals who really
understand burnout, especially

the context that comes with a
founder. To be honest, if you

looked at the psychological
profile of most founders, they

look a little bit like somebody
who's a little bit manic, has

maybe a little bipolar too going
on, is a little bit obsessive

and then has these sort of fits
of depression. And so I think

it's really easy for mental
health professionals to

pathologize founders and not
understand the context and the

amount of passion and drive and
energy that goes into growing a

business. And I think that's
where we miss each other a

little bit.

Arvid Kahl: Yeah, that was
exactly what I was wondering

when I saw my 89% of people
telling me and I think it was 10

ish or 20% that we're in burnout
right now as per their self

diagnosis. And I was thinking,
man, is that just an

entrepreneurial thing? Is that
just the founder, kind of people

just have an easier time having
a hard time? Does it hit

entrepreneurs harder than other
groups have? Have you

experienced this?

Dr. Sherry Walling: So it's a
little bit tricky because I

think burnout is also a nice
phrase to describe a number of

different things. So sometimes
people will say, I think I'm

burned out and then you dig into
their life and their situation.

And it's like, oh, you are in
very significant grief. Or

sometimes people will say, I'm
burned out and I dig a little

bit and I'm like, oh, wait,
actually you're like clinically

depressed like, just textbook
depression. But burnout is an

easier term to talk about even
though it is still stigmatized.

It's maybe less stigmatized than
some other things. So that's one

of the problems that I think is
happening. There was an

interesting study that came out
relatively recently that

suggested that entrepreneurs
actually have less burnout than

your nine to five employee. And
some of that is because there

are these key things that drive
burnout. Some of them are better

for founders, like, one of the
drivers of burnout is the

mismatch between what you think
is important and how you spend

your time. So at least
entrepreneurs are choosing,

right? They are deciding what
business they want to build.

They are giving their time and
energy towards something that

they're choosing. They're not
out of control. They're very

much in control. So that's a
protective factor that helps

prevent burnout that's not
present in you know, our

brothers and sisters who are
working in a cubicle coding for

a large company where they don't
have choice or control.

Arvid Kahl: That's such a great
point. Because as now, after

selling a business, I'm very
much in control of what I'm

doing. And I am my own boss,
really. And I'm telling myself

that I'm gonna do this and if
it's too much for me, I'm just

gonna step back a little bit. I
have nobody who's kind of

conflating this for me or
telling me to do stuff I don't

want to do so I feel extremely
at ease in what I do even

though, you know, being an
introvert, having conversations

with people is not like the most
enjoyable thing really, like I

think hanging out with my puppy
is a more enjoyable thing.

Dr. Sherry Walling: That's a
relationship for you.

Arvid Kahl: Yeah, really, it
really is. Because the puppy

doesn't challenge me, you know.
She does but in different ways.

But I know, obviously, that
having a conversation with you

is an important part of what I
can do to help other people. So

I know that there's meaning to
this. And it's what I want to

do, right? It's not the mismatch
between I don't wanna go with

this, but I actually want to do
this, so I get it. But I do

wonder sometimes with founders
in particular, who are building

their first business, people who
still have something to prove if

that is a phrase that we should
ever use in terms of building a

business. They often follow what
I would describe as hustle

culture or the grind set, right?
This kind of put all your energy

and all your time into your
business or else you'll never

make it. And that seems very
disjointed from this I have

control over my destiny
conversation we're currently


Dr. Sherry Walling: Yeah,
sometimes we say, oh, good,

you're an entrepreneur. You can
choose to work whichever 20

hours in a day you'd like. Like
you get control and choose.

Yeah, I mean, hustle porn,
hustle culture much of it is

based on a real sort of limited
understanding of how our brains

actually work. And so a little
bit of a scratch into some

basic, like neuroscience 101.
And I think most people will

come away feeling like, oh,
that's not the right strategy.

There's a difference between
doing a lot of work and doing

our best work. And I think
sometimes that's where founders

make maybe a less than ideal
trade is this sense that hours

logged leads directly to
outcomes. And, you know, there

are days when that's true, but
generally speaking, the quality

of your work time is a much
better predictor of your

creative thought and of your
ability to implement a new or

novel idea than just sort of
putting in the hours. And I do

think that it is sort of hustle
culture, hustle porn that is the

allure to believe that burnout
is not only normal, but like a

badge of honor, like sort of
like if you're not burnt out,

what are you doing with
yourself? You must not care

about your company. You must not
be motivated. And of course,

Arvid Kahl: Yeah, it often comes
from comparison, right? You

compare yourself to other
people's stellar performance,

those things are not true.

the things they choose to share,
and you see all these founders

crushing it, a phrase that I
personally hate a lot because

it's obviously just a reflection
on what they want to portray.

It's not the reality of their
lives, because no business is

ever without problems or
setbacks or anything like it.

And I wonder, I think it's human
nature to compare yourselves to

your peers to see where you
stand, because we want to see

that the social context in which
we operate, and if we're

conforming with the what people
expect us to be and you know,

there are many layers to this
but how can people avoid

comparing themselves to the
wrong people and then following

these hustle culture evangelists
who themselves probably even

operate in the way that they
give advice.

Dr. Sherry Walling: Right? I
think one of the really helpful

place of comparison is maybe not
the word that I would use. But a

helpful way to learn from and be
on the journey with other people

is to be in a mastermind group,
or something where you get a

deeper look into how another
business is truly functioning. I

think another way to do that is
to have a mentor, I mean, maybe

even someone that you pay, maybe
they're a business coach, but a

mentor who has truly done it
before, and you get the deep

dive gritty look into how they
function and how they work. So

anybody who is selling you
something, or anybody who is

proclaiming the benefits of
their strategies on social

media, you're just not getting a
deep enough dive into who they

are and how their business works
to know if it's at all relevant

to you. And relevancy is a
really key businesses are

different different sort of, you
know, industries and customer

bases are really different. And
so having a sounding board with

other founders that's tailored
and specific is most helpful to


Arvid Kahl: That's great. That's
why I'm such a big fan of

building and public because
people who Build in public and

share the ups and the downs with
a focus on the failures and the

struggle, the mistakes and the
learning set they have, they

paint a much more realistic
picture of what the business is

like and surrounding ourselves
with people who are honest

enough to build in public also
creates relationships with

honest people who will give you
their honest feedback. If you're

doing something you should
probably not be doing it. That's

why I'm a big fan of this. And I
guess a mastermind is privatize

building public group, if that
makes sense. You know, like a

little, little group of that
where people keep it to

themselves, but do share with
each other. And I think it's a

great step for people to start.
Do you have any ideas how people

can easily find them? Because
I've always found not maybe not

easily but reliably find good
mastermind groups? Because

personally, I've always had
trouble as an introvert, again,

talking to people to even get
into the door, right to get my

foot into the door, that always
was a challenge to overcome this

person. I don't know them. Why
would they talk to me? Like, I

would assume that a lot of
founders, particularly the ones

coming from a technical
background, have a little bit of

introversion in them. So how can
they overcome that particular

self blocking device?

Dr. Sherry Walling: I mean, not
to like promote by husband stuff

but MicroConf does have a
mastermind matching service at

this point. There's also another
one, that I'm not sure if it's

still going. But mastermind jam
was a service that a friend can

did for many years, I'm not
totally sure if that's still

happening. But the MicroConf one
is for sure. I think it's a

good, it's a good thing to even
crowdsource right to put out to

Twitter and to try to connect
with some people who are

interested in a mastermind, I do
find more value in ones that are

like externally organized and
have maybe a nominal or a

minimal fee, because that puts
skin in the game. The worst

thing is getting into a
mastermind group with people who

say they're committed and then
they don't show up, you know,

and it's, you're just chasing
them to get on their calendar

that it that's not good for
anybody. So some kind of like

base level of commitment is
really important in a mastermind


Arvid Kahl: Yeah, yeah. skin in
the game, I think is for any

relationship that has a business
connotation is an important

part. I love that. And by the
way, I give you blanket

permission to advertise whatever
your husband does. family

business, because honestly, if
it wasn't for MicroConf, I

probably wouldn't be here.
Right. MicroConf gave me the

first stage quite literally, for
what I had to say when I was

there in 2019 in Dubrovnik with
Danielle, we talked about having

sold our business on stage as an
attendee talk. And that was

essentially my foray into
talking about entrepreneurship.

And from there, all the way up.
So it's evening, it's due to

Rob, that is funny, because you
are also connected to our sale

in the way and I'll tell you in
a second, it's for Rob's

conference that I got my Twitter
situation going. But it was

mostly for you a book, the first
the first book that I ever read

of you, the entrepreneurs guide
to keeping a shit together. I

read this while we were selling
our business. And I was and that

was mid 2019. And that was in my
my own memory, which is kind of,

you know, a bit spotty, because
it was a weird and very intense

time. Intense time, right? It
was incredibly intense. even

thinking about it is a heart
rate increasing endeavor. For me

at this point, it really is I'm
noticing a physical sensation

right now. I was either at the
verge off or mid burnout, I

don't really know. It was it was
a strong I had high anxiety

levels, I was extremely
stressed, trouble sleeping,

physical reactions, gut health
was off. Like all of that kind

of stuff happened to me at the
time. It's one of the reasons

that we actually sold the
business at that point was

because I just couldn't really
handle all the responsibility of

being one of two people in a
business, Danielle and I never

hired anybody. And being the
only technical person in that

business, being tasked with
solving all the problems of our

five and a half 1000 customer
base. It was a lot. And your

book, I remember this still
very, very visually gave me a

lot of solace and hope for being
able to, to weather this time

and find the greener grass on
the other side of this eye. It

may not be as eloquent,
eloquently expressed as I would

like it to be. But I think
reading a book from somebody's

perspective, who understands how
stress and anxiety works in a

person and what it makes you do
and not do, just knowing that

I'm not alone, and that there is
a way out of this was incredibly

helpful. So thank you so much
for enabling me to go through

this process and holding my hand
a little bit right through the

magic of authorship throughout
this stressful time and enabling

me to just get rid of the my own
self inflicted and external

pressure and make my life
better. I'm happy at this point,

because in large part to your
guidance for this book,

Dr. Sherry Walling: Well,
there's no kind of words you

could give an author to say your
book mattered to me, not into my

life. So I'm very, very
delighted to hear that and glad

that it was a useful touch point
and sort of guidepost when you

were trying to sort out how you
needed to move on from your


Arvid Kahl: It was surprised at
that point that your work was, I

guess, the only book I could
find on this whole issue. I

mean, good positioning, I guess
for you, right? You get all the

sales, but in a way, it was
surprising. And it it still

feels surprising to me how few
works there are in the field,

intersecting the lives of
founders with the lives of

regular people, right, like
having regular people problems,

that that seems to be such a
rare thing to find. And I'm glad

you you took the time and effort
and actually codified it into a

book because I think I've been
recommending this for every

single founder that has asked me
about dealing with mental health

issues, or just stress and
anxiety in this whole process of

building and mostly exiting a
business, that my experience

kind of with this book has
helped me recommend it to other

people. And, yes, I think
there's, I don't want you to

have more competitors in your
field, obviously. But I think

there should be more helping
people get different

perspectives on the same issue,

Dr. Sherry Walling: Yeah. And,
yeah, I think I do think it's a

conversation that happens,
people don't always call it

mental health, sometimes they
call it mindset, sometimes they

call it you know, they kind of
package it under other things.

There aren't a lot of formally
trained mental health

professionals at this space,
which I think is a problem.

There's a lot of founders that
have ideas about it, which is

super, super valid. But I do
think that the professional

training is pretty helpful in
some of these conversations. So

and I think my next book is
going to be about exiting your

business. So perfect, maybe a
little late for your first

round. But

Arvid Kahl: honestly, it's, I
would rather have you write it

now than never write it. You
know, like, my whole mission

ever since I sold the business
was to kind of pay it forward.

So I feel whatever didn't exist
when I was dead. That's why I

wrote my first book, because I
would have liked to read it when

I needed it. And it's kind of
the the approach that I have to

media now. And let's talk about
the book that you just released,

maybe because while I haven't
read it, what I've seen, in your

very touching, really touching
marketing materials around it

has been something that I can
relate to, even though I haven't

read the book, and maybe I will,
I will give you the opportunity

to explain first what the book
is about. And then I will kind

of integrate my actual story
into this.

Dr. Sherry Walling: Yeah. So the
book is called touching two

worlds. And it is part memoir
and then part analysis as a

psychologist into the world of
grief. So the book was kind of

an accidental book, in that it
was written, I lost my dad to

esophageal cancer and my brother
to suicide within six months of

each other. That was in 2018,
2019. And so a big part of my

just personal process around
working through those

experiences was to write about
them, and was to begin talking

to people about grief. And I
think what's so interesting with

those of us who are founders are
high performing professionals

are, you know, we're the people
who are on the go the movers and

the shakers of the world, we
often don't give ourselves much

space for grief. You know, it
feels like I'm busy creating a

world I'm not going to mourn the
things that aren't around

anymore. And I really found that
to be a problem, especially in

entrepreneurs and in founders,
as they have, in many cases,

these really unprocessed losses
that shape them in ways that are

unexpected, but yet quite
powerful. So writing about it is

my attempt to work through it
myself and to sort of offer

offer some notes and guidance to
people who are coming after me

who've had similar losses.

Arvid Kahl: It's and that is why
I intersect with that story

because I think on Process loss
is something that I have

struggled with without knowing
for decades. At this point, I

lost my mother when I was 18, to
suicide as well. And that was a

for an 18 year old and an
processable moment, I feel I

remember that it was just a fact
I dealt with. And I then very

slowly, like a background
process, the height, everything

else I was doing, dealt with it
for the next decade. And it was

around 28, when I started to
actually become a programmer

before that, I was just like
hanging around University in

Germany, because it's paid for
by the Government. So might just

as well, I had a great time I
learned stuff, and I was coding

on the site. And but I really
only became a professional

software engineer 10 years after
that, and it took me that long,

I recognize that now being yet
another 10 years older, that

that was the time that because I
had no help, I had to deal with

it, and chunks, I had to just
deal with all the emotional

baggage of how it affected other
people around me how it affected

my life and my studies. And, you
know, essentially what was still

somewhat of a child growing into
an adult. All of this had to be

done kind of by figuring stuff
out. And I had really no

guidance there and no help. And
that impacted how long it took

me to even be able to
effectively work as a beat as a

human being right, it took me a
decade, which is like if I

hadn't had the support of the
country I lived in and the

people around me, that would
have been very troublesome for

me. So I definitely understand
not dealing with stuff for a

long time. And it's a problem,
right? It's a problem that

affected me for again, a decade,
and it shouldn't have. So I'm

very grateful that you reflect
on this in in public with what

the book is. And I love the idea
that this book is also memoir

slash self reflection method for
you. I think writing is such a

powerful tool to come to, to
your own thoughts and understand

your own thinking. That is that
is one way that I I feel very

strongly for the topic. And I'm
grateful that you wrote about

it. And the other one is now
entrepreneurship related. And

that is something that I might
want to touch on. Because the

idea of grief, to me was always,
from my own experience, a very

person related thing, right? You
grieve a person, and you grieve

the loss of a person. But when
we sold the business, and I'm

trying to be very careful here,
the business is not a person,

right? The business is a thing.
It's an entity you create, and

you set up and it runs and
you're operated. It's almost

more of a machine. But we felt a
very strong sense of grief when

we handed over the keys to the
business. Something we did never

expect. Even though my my
partner and I Danielle and I we

were life partners and business
partners at the same time. We

joked about it being our baby,
right? It's it wasn't obviously

because it doesn't love you back
babies do. But the business was

something that we gave over and
felt this incredibly intense and

mind altering state of grief.
And I think I would have liked

to be prepared for this. No,
that's why I'm

Dr. Sherry Walling: writing my
next book about exits. Because

your experience is not unusual.
And just to sort of clarify from

even, you know, the professional
psychologists perspective, grief

is the emotional reaction to
loss and loss has many forms. So

we think about it maybe most
often in reaction to the loss of

life. But I mean, I think the
the pandemic was so interesting,

because it created so much grief
around our loss of plans, our

loss of mobility, our loss of
travel, you know, these things

that are not human, but yet were
very significant things to lose,

and the loss of a business. You
know, you say your business is

not your baby, and I get it,
it's not. But there's a there's

a really interesting study that
looks at fMRI of entrepreneurs

brains when they're thinking
about their businesses. And the

activation in the brain is very,
very similar to the brain

activity that is in play when a
parent is thinking about their

child. So there is a deep level
of attachment and identification

with your business that is
undeniably this form of bonding.

And so to lose that attachment
to lose that connection, whether

it's by a sale or by a financial
crisis, implosion that results

in the closing of the business.
Grief is a really important part

of that process. And I think
people forget about that,

especially with an exit you know
that it's supposed to be the

happy story. It's supposed to be
your cry Passing the finish

line, it's everything you've
been working for, and people

expect that it's going to be,
you know, you're the envio. But

in reality, it's very
emotionally complicated. I think

maybe a fair comparison is sort
of what it feels like for

parents who are sending children
off to college, or out of when

they're launching their kids.
It's like everything you've been

working for, and everything that
you, you know, are ready for.

But then when you're walking by
their empty bedroom, it's

there's a desperate amount of
grief, it's very painful.

Arvid Kahl: Yeah, it's something
that I'm not a parent, so I did

not expect it in the slightest.
Like, I've never, never

experienced anything like it. If
I felt like my, my source of

passion was drained away from
me, I get that that was the

perception that I had, I was
doing this, not because it made

us money. But that was great.
But that was not the reason we

built the business. We wanted to
help these people. And in our

case, it was online English
teachers. And these people still

existed after we sold the
business. And I still wanted to

help them because that was what
I found so much joy and passion

and purpose, mostly purpose in
as well. And with giving away

the business, the purpose of
what my day was about, was not

something that I had any kind of
connection anymore. I was so

connected with the business that
it was kind of I was tethered to

it, that rupturing the tether
that had backlash. It was there

was a kind of tension

Unknown: artery. Yeah, exactly.

Arvid Kahl: And sometimes I
think that entrepreneurship is

all about balancing two
extremes. And this is one of

those examples to me, you have
the extreme connection that you

have with your business. And
then something that that I have

experienced myself, and that I
see so many other founders

experience, you have a lack of
connection with the people

around you that don't understand
what you're doing. That to me,

is a big, big entrepreneurial
problem as well. And I want to

talk to you about it, because
there's the story that a fellow

founder Dagoba Renouf, he tells
this, I think it's in his

Twitter bio as well, that his
father in law did not want him

to start the business with his
wife, right? The story is that

it didn't understand or condone
that the couple, the newly

married couple would start a
bootstrap business together, he

was not a fan of this. And that
must be super stressful. If the

people you need to support you
the most are disconnected from

you, because they just do not,
they don't support you, they

don't understand you. And at the
same time, you're building this

very intimate connection with
this inanimate being that is

your business, right? It kind of
pulls you to both sides, you

want to connect here, but
there's no response. And you you

do connect here, there's also no
response. Entrepreneurship is

hard, right? It's just such a
such a struggle. What do you

think about this? What do you
think about like family support,

when it doesn't exist? When
people don't understand what

you're doing? How can you deal
with this as a founder,

Dr. Sherry Walling: you don't
think it's the, it's the lot in

life for many creatives and
money. You know, I had dinner

with somebody last night, who's
a professional circus artist,

and she was like, Yeah, my
family cut me off. When I

decided to be a circus artist,
they were like, if you're gonna

do that, you're doing it by
yourself. And anytime that

someone is taking big risks that
feel scary and difficult to

understand, for those who love
them, there's a level of

distancing that happens, and it
happens fairly commonly. And

it's, in some ways your families
attempt to protect themselves

from the downside from your
failure, which is not pleasant

right into it. It's sort of
abandoning you and the risk. But

um, I think it's important. It's
tricky. And entrepreneurship,

because again, it is the center
of your world, and it's the

center of your life. But there's
also an argument to be made for

the fact that it can be kind of
a job. And you can have

relationships with people who
don't get it, they don't

understand. I mean, there were
times in Rob's professional life

when I really didn't quite
understand what he did. Like,

I'm not technical. I was just
like, I don't know what your

what are you doing all day? Are
you typing zeros and ones like

what is what is? So I'm at but
yet I loved him no matter what,

like I loved him, despite not
really being able to understand

similarly in my life as a
clinical psychologist, you know,

early on, I worked with post
traumatic stress disorder and

recently returned veterans and
he was like, that's a whole

other world. Like, I'd never I
couldn't think about how I would

do that. You know, it was just
the separateness was tolerable.

And so I think it's important
for entrepreneurs to recognize

you need a posse of people that
do get it you need that

mastermind you need that
community you need some people

that you can really talk shop
with. But you are not so special

in your life as a business
owner, that it's not also

important for you to have
meaningful and deep connections

with people who aren't
entrepreneurs, and just don't

care what you do during the day.
So those are also really

important relationships. And I
think sometimes entrepreneurs

sacrifice those relationships,
because they are so attached to

their business, that it's so
painful that they aren't

understood as an entrepreneur,
and it shouldn't be it's just a

part of you.

Arvid Kahl: Balance, right, you
need to balance the, the the

people who are on your level.
And I mean, there's not as a,

you know, ranking system, but
who aren't you frequency maybe

who vibe with what you do. And
you still need to have the

external, different the other
another group of people who are

different from you. So you can
kind of see, Am I overreacting?

Am I spending too much time with
this. And I think like lots of

founders, particularly
solopreneurs have this problem,

where they focus so much on the
business and they see the

opportunity, they see the
potential, right, they see oh,

wow, if I keep growing this,
this kind of harkens back to the

whole grain set thing from
earlier, if I spend more time

doing marketing, reach out to
more people get this going, then

this will be the wealth
generating thing that I want it

to be, and then I can finally
retire and buy a house for my

parents, right? They have this
dream that involves other

people, but the process does
not. And I think that's what

that's such a dangerous thing to
to consider. But it's also

apparently something that many
people assume to be the right

way, and that they don't need
help they have trouble asking

for help. Is do you see this in
entrepreneurs? Is this a founder

thing that they are taught that
they can do and should do

everything by themselves and
don't ask for help. And that

kind of transforms into the self
inflicted loneliness.

Dr. Sherry Walling: I mean, most
of us have a family story that

necessitates that, I mean, you
with the loss of your mom, are

really used to doing things
yourself and figuring out how to

do it by yourself. I mean, I
grew up with parents that had

really significant physical
medical problems, my mom was

disabled in a wheelchair. And so
that was part of my story to

just I needed to figure things
out myself, if I needed to get

something I need to get up and
go get it like there's nobody

going to do it for you. And a
lot of entrepreneurs have

stories like that, it's sort of
what qualifies us to believe I

can do that. So it's a it's a
strength, in a lot of ways. And

often, it's a way that we've
made sense of difficult

experiences in our lives. But of
course, the downside is the

isolation. And we believe that
just because, you know, someone

else isn't in the nitty gritty
of our business and isn't

pushing the business forward the
way that we are, we sort of

believe that they can't
understand or that they can't

care about us. And that's the
that's the isolationist mistake

that we make.

Arvid Kahl: How do we pull
ourselves out of this? Like, how

do we open up our lives? So we
can have these people in it

without risking not focusing on
up on on our business? Like,

where? Where do we balanced us?

Dr. Sherry Walling: You know,
one of the things that I think

is really, really helpful is to
have a hobby, where you have a

coach. So if you follow me on
social media at all, you know

that I have a funny hobby, which
is, I'm a circus artist. And I

came into that late in life, I
was 40 when I started. But it's

been a really, really important
part of life. For many of these

reasons. I regularly train with
other people, I regularly train

with a coach. So I get practice
being helped, being taught

listening, following directions,
going when somebody tells me to

go. And then I hang out with
this whole community of people

who does not care what my
monthly revenue is, or what my

churn was, or you know, they
just don't care. They just care

if I show up and do my stretches
and come on time and like, do

the thing. So having a hobby is
something that I think is a

really lovely offset to the
stresses of entrepreneurship,

especially if it gets you in
your body and sort of out of

your desk chair not looking at
your laptop, it just varies the

way that you're using your time
and your energy that can be

super, super valuable to our
neurological health. And then

we're also mixing up the
relationship dynamics. Like it's

really good for me to not be the
boss sometimes. You know, I'm

the boss of my kids, sort of.
I'm the boss of my team. I'm the

boss of my business. Yes. And so
to go somewhere and just be a

student, and be a learner is
really, it's really good.

Arvid Kahl: How you bring you
bring to mind something that I

just read. This week in Wired
magazine, I have a print

subscription to Wired Magazine.
That's how old I am. I read

things in print. And then there
was a writing letter to Wired

magazine was somebody asked the
column, this advice columnist.

I'm not ready to pay for
therapy. But I see these mental

health apps, these mindfulness
apps all the time, right? Is

this useful? That was the
question. And the answer was,

right, mental health apps. Yeah,
they're not a replacement for

therapy, definitely not. And
what they actually are, are like

a digitized version of self help
books or self the self help

approach. That was what it said.
And it had it ended with the

phrase, I don't want to talk
about the whole art whole

article, I'm gonna put it in the
show notes, because I think it's

on the web as well. But what it
ended with was, Hey, you are

when you use these apps, you try
to control your breathing, and

you track your pulse, and you
start this kind of biohacking,

try to interpret every single
data point from your body, you

don't want to get on the couch,
you need to get off the couch,

you need to actually hang out
with other people. Because if

you hang out with other people,
if you do collective sports, or

you engage in conversations with
other people, then you're not

focused on breathing anymore,
because your body is capable of

breathing all by itself, that
was kind of the answer to this

was stop focusing so much on
optimizing yourself, right and

self help self self care is
important. But it's not the

solution to all of your
problems, the underlying problem

might just as well that you
don't have enough exposure to

other people to put put you back
into the social context that you

live in. And I love this idea,
like do stuff with people and

your body will keep breathing,
just trust it to keep breathing.

That's what it reminded me of,
because you said you're the boss

of your family, your business,
you're also the boss of

yourself, right of your own
physical being. And if you start

micromanaging your physical
process of breathing of, you

know, when do I do this? When do
I do that? I don't think that's

necessarily a good way to deal
with with problems that you may

be having

Dr. Sherry Walling: was sort of
dissecting us into too many

different parts, I actually
think breathwork is very

helpful, and I practice it, I
have an app that I really like.

I think meditation is helpful
yoga is helpful, like these

practices do teach us the
capacity to regulate our bodies,

which many of us have sort of
lost those skills, but they

aren't the end result, like I do
breath work, so that I can

perform well on a flying
trapeze. You know, it's it gets

me where I'd like to go in my
life where I do meditation so

that I can prepare to give a
talk in front of hundreds of

people, and feel grounded and
connected to myself. So those

tools are tools and having a
bunch of them is great, but

don't glorify them as the
outcome or as the end all be all

of self care. I like a hobby
because it's about joy and play,

and lightheartedness and
laughter and connection. And

those are really good, juicy
parts of life that don't need to

be hacked or optimized, but they
do need time to take place.

Arvid Kahl: Does that is a
really nice and very nuanced

position on this. Because I also
I have found through Danielle,

thankfully, that meditation and
journaling and mindfulness and

breathing work is actually
helpful to me, I consider these

things in the past to be purely
esoteric, that to me was an

adult that was meant as an
insult at that point, right. And

now I consider them surprisingly
useful, which is something I've

tried it out I actually, again,
MicroConf story, the day that

Danielle and I were giving the
talk in Dubrovnik in Croatia

back in 2019. I was very
excited. First time I would ever

stand on stage in front of my
fellow founders, many of which,

at that conference I had have
been admiring for years, and

sharing a story that I with my
imposter syndrome at the time.

And it never really went away
thought I was just lucky to even

be in this place at this time
having done all these things,

standing on the shoulders of
giants really. And I was sitting

there in the morning of that day
in our little hotel room looking

at the Adriatic Sea, beautiful
place. And I was I was feeling

my anxiety. And what I did was I
just journaled for half an hour

I did a stream of consciousness
journaling, which I think is

called Morning pages by some
other people. Well, you just

Yep, exactly. And it was the
morning so it was adequately

described as morning pages, but
just me stream of consciousness

whatever was on my mind, I put
it on paper, and then I just

kind of threw it away. I never
looked at it again. It was not

meant to be read it was meant to
be written. So So I could take

those thoughts out of my mind,
give my mind the, the

understanding that it was
noticed somewhere. And now you

don't have to keep running
through the ideas. And in real

time, you could just put it in
the background and worked super

well. For me, it was such a
surprising thing. And I've been

doing it before that too. So I
knew it was going to work, which

is why I did it, that Danielle
introduced me to these concepts

while I was dealing with the
whole business side, right, the

burnout in feedback panda before
we sold it. And it really helped

me ground myself. And I never
thought before I met Danielle,

and with her had the
opportunities of a lifetime

building and selling your
business, which is great, she's

awesome. I never thought that I
would be the person that could

employ these techniques. So now
that we are talking about it,

how can technical people who
don't believe in this and

engineering backgrounds
solopreneurs approach these soft

topics like meditation and

Dr. Sherry Walling: I'm sorry, I
just love the like soft topic

quotation, because we have very
robust research from very

mainstream places like Harvard
Medical School, to really

understand what's happening in
our bodies, when we engage,

meditation, breathwork, or
journaling, let's just use those

as three. They're widely
accessible, they're available,

and they both have very
significant scientific support.

One of the things that I think
has happened to us as modern

humans is that we've really
separated our minds from our

bodies, and especially as
technical workers, we, we'd love

a big juicy mind. Like we like
being able to solve problems and

code and very nuanced ways to
stay focused for long periods of

time. But we've forgotten that
everything that happens in that

organ, is part of a larger body
system. And we do much better

when we can integrate our
physiological well being into

our neurological well being,
we're doing it all the time,

it's not a choice, it's how our
brain works. But things like

meditation, journaling breath
work, are very, very helpful to

keeping our physiological system
regulated, so that it can

optimize the functioning of our
brains. And so I would, anybody

who like doesn't believe in this
science, like, just do it, just

do a little lit review on a
medical journal, or like Google

it. And, you know, I think it's
fairly undebatable at this

point. And the good thing is
that these tools are very,

they're really accessible. Like,
you can do a five minute

breathwork practice and sort of
reset your body for a while, or

you can do a little meditation
app. And it's not a replacement

for exercise. It's not a
replacement for therapy. It's

not a replacement for
friendship, but it is a strategy

to help nourish your brain and
calm your body down when you

need to perform at a high level.

Arvid Kahl: Yeah, and that's why
I kind of put it in quotes too,

because it is obviously working.
Right. And it's obviously also

like, scientifically, not just
described, but proven and

integrated. I mean, if calm, the
app has such a wide range. And

honestly, if it has so much
success as a business, it must

be doing something right. Right.
Like even for, for somebody who

only wants to think in technical
terms, this is a very logical

conclusion that you have to come
to. And I'm kind of I'm talking

from a current perspective to
the person that I used to be

when I didn't believe in it. So
that's kind of where my phrasing

is coming from. But I still feel
a lot of people have trouble

with the way it is presented.
You know, like the way that

solutions to mental health
problems are presented for many

people are, I don't really know,
the let me think about this. How

would I phrase this in a very
wishy washy kind of way? Is that

a phrase that translates from
German? Because, you know, like,

people want like very discreet
methods. People want the quick

hack, that is the right people

Dr. Sherry Walling: That's kind
of where I started in our

conversation, right? Like, why
isn't why aren't more people

talking about this? And I'll
tell you, because the honest to

God, truth is that there's not a
lot of like, click Beatty,

things that you can say that are
going to make a big impact.

Because I can tell you and I can
show you research studies that

say if you meditate for 20
minutes a day, you're going to

improve your focus and
creativity and overall brain

health. But there's a whole lot
of complexity behind how you

create space for something like
that. What gets in the way of

you sort of disciplining
yourself to do that, do you

value wit, do you even really
care if your brain is I mean,

that's where we get pretty
complicated. So the problem

isn't so much whether or not
these tools work, the problem is

our human complexity around
implementing them effectively.

Arvid Kahl: Certain educational
problem too, like you think this

should be way more front and
center in the way we teach

people to be people.

Dr. Sherry Walling: Yeah. Again,
I think we've segmented the

brain and the body, or the mind
and the body. And that's, that's

a kickback from Decart. Like,
these are long held beliefs that

are that are fundamentally

Arvid Kahl: Yeah, to me, it
reminds me of this division that

we have between knowledge work,
and non knowledge work. Like as

if the person doing the
knowledge work wouldn't have a

human body that is acting
physically, it's often confuses

me to think like, just because
I'm not moving stuff around. I'm

still physically, like burning
energy to fuel the brain that

controls these things.

Dr. Sherry Walling: We got lots
of work to do with our

conversations around mental
health. But I'm glad we're

having this one.

Arvid Kahl: I am very glad we
were having this one too. And I

think I just wish it was easier
to talk about it in our

communities, I feel a lot of
people have this kind of notion

that if they share anything that
is potentially showing that they

are not at peak physical and
mental health, they're

vulnerable. And they're not
worthy of being surrounded by

all these other high performers.
I think that's such a such a bad

situation to start with. I

Dr. Sherry Walling: just think
that's increasingly not true.

Like we've had people like Gary
Vander Chuck talking about

depression, you know, within our
own technical people like Steli

Efti, in his podcast about inner
work, like, being quite open

about things that he's learning
and trying about his own inner

world. Most MicroConf, for
example, have some element of

mental health or mindset
present, if I'm not doing it,

somebody else's. But

Arvid Kahl: maybe the next one.
I know somebody who might be

there talking about these
topics. Yeah, it's it's, it's,

it's, I'm glad that this
happens. Because with every

conversation that we have around
the topic, we show other people

that it's Okay to have a
conversation about this topic.

Yeah. Right. That's, that's
just, which is why I'm, let me

bring this to a close, which is
why I'm so happy that you're

here today, and had this
conversation with me right now.

Because I hope that a lot of
people who are listening to this

will not just take something out
of it, but also encourage other

people around them who they see
struggling or not struggling

doesn't matter, you often don't
see people struggle, right? Even

though they do to, to listen to
it and find encouragement to

talk about these things
themselves. And to learn from

you again, like I'm, I'm not
going to push anything here, but

people should really read your
work. Because it was it was

quite really, yeah, they should.
It was quite helpful.

Dr. Sherry Walling: Yeah, a
couple of books. I have a

podcast, I just did a TEDx talk.

Arvid Kahl: Where can people
find you? Maybe let's let's

codify it like this? Where do
you want people to find you?

Dr. Sherry Walling: My
professional work is mostly on

Zen, which is also
the name of my podcast. And you

can see links and descriptions
of the books that I've written,

or the retreats or events that
I'm hosting. And then you can

also follow me on social media.
If you're curious about how a

psychologist also was a circus
artist, I do a lot of that on on

Instagram, and Twitter and
LinkedIn. So

Arvid Kahl: I highly recommend
that follow because it might

like if you're listening to
this, and you think, yeah, I

think I need to deal with a
couple of issues that I haven't

thought about much, following
Sherry's a very good idea. And

it will be it will make your
journey easier, and you'll come

out as a better person with a
better understanding of

yourself. So thank you so much
for being on today and talking

to me about all these
complicated and often heavy

things. It was a real eye
opening conversation. Thank you

so much.

Dr. Sherry Walling: Yeah, thank

Arvid Kahl: And that's it for
today. Thank you for listening

to The Bootstrapped Founder. You
can find me on Twitter

@arvidkahl. You'll find my books
and my Twitter course there as

well. If you want to support me
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Any of this will truly help to
show. So thank you so much for

listening and have a wonderful
day. Bye bye