What's up, everyone?
This is Cortland from IndieHackers.com, and you're listening to the Indie Hackers podcast.
On this show, I talk to the founders of profitable internet businesses, and I try to get a sense
of what it's like to be in their shoes.
How did they get to where they are today?
How did they make decisions both at their companies and in their personal lives?
And what makes their businesses tick?
Today I'm talking to Dr. Sherry Walling, the creator of ZenFounder.
Sherry is an academic and professional powerhouse with multiple master's degrees, a PhD in clinical
psychology, and she's also worked as a professor at multiple universities.
She has extensive experience researching and treating the victims of post-traumatic stress
disorder.
And in recent years, she's taken her skills and her learnings in that area and applied
them to help entrepreneurs and their mental health.
So this is going to be, I think, a very different conversation than we're used to having on
the podcast, but this is fundamental, important stuff that I don't think it's talked about
often enough.
So Dr. Walling, I'm excited to have you here, and thanks so much for coming on the show.
Hey, thank you, Cora, and I am super excited to be here and talk with you.
Let's talk about this path that you took from studying trauma and PTSD and working with
patients to working with entrepreneurs.
I know that trauma is a very serious issue.
I think it's hard to overstate how much of an effect it can have on a person.
What if anything is the relationship between being an entrepreneur and being a victim of
trauma?
That's a really interesting question, and I gotta be honest, I don't think that many
people have asked me that before.
I think they assume that I've made a shift, but I really haven't made that much of a shift.
One of the things that I bump up against a lot in my conversations with entrepreneurs
is that I think many, many founders have their own significant stories of early loss or traumatic
experiences that in some ways have shaped their path towards entrepreneurship.
Many of the founders that I work with are themselves survivors of very difficult early
life experiences, and I think the kind of life or death or the high intensity of those
experiences in some ways prepares them to be founders.
I will also say that the capacity to cope with a lot of intensity is something that
a lot of trauma survivors have to get comfortable with.
I think that's really common in the founder space as well.
Lots of entrepreneurs have to learn to navigate high highs and low lows and a lot of anxiety
and stress.
When people are resilient in the aftermath of trauma, that's often one of the skills
that they walk away with, which serves them very well in the founder space.
That's interesting.
That the set of skills you develop in order to cope with being a trauma survivor happened
to overlap with the set of skills that you need to be a successful and a skilled founder.
To some extent, yeah.
Of course, there's exceptions to all of this, but it was this interesting bridge that I
took.
My work in post-traumatic stress disorder was largely with people who were professionals
in the military, so lots of officers, lots of medics, lots of folks who had important
jobs in the military and then experienced either sexual trauma in the course of their
deployment or combat-related trauma while they were in the military.
From that early career specialty, I worked a lot with physicians, so another set of professionals
who in many cases have just really hard, hard things happen in their jobs.
It was this stair step to yet another group of folks, and I'm not saying that folks who
are building businesses are seeing kids die or experiencing assaults.
I'm not making that comparison, but I will say that I've always worked with really intense,
intelligent, high-functioning, really amazing professionals who are also trying to cope
with some significant pain in their lives.
It's definitely not black or white.
You either have trauma or you don't.
There's definitely degrees and shades of gray, and I think it can be difficult for people
who haven't read about this stuff or haven't seen a professional to even know if the levels
of stress they've been through earlier in their lives are contributing to issues or
challenges that they're facing today.
What are some, I think, indicators or some things that can happen to a professional that
might, I guess, give them mild cases of trauma?
One of the studies that I talk a lot with founders about is the Adverse Childhood Experiences
study, which was a study that was done about 10 years ago, maybe a little more than that
now, that looked at 17,000 people.
It was conducted as a partnership between the Centers for Disease Control and Prevention
and Kaiser.
They looked at all these health records and they interviewed people and asked them about
10 categories of early life experiences, adverse childhood experiences.
Exposure to physical abuse, sexual abuse, physical neglect, emotional neglect, having
a family member incarcerated, having a parent who does drugs.
There's this whole list of things.
One of the things that was on the list was parental divorce, which is not necessarily
a trauma with a capital T, but can be quite adverse, can be a pretty troubling experience
for a child, depending on when and how that happens.
They looked at these 10 categories of things and the research results are very compelling
in terms of the relationship between early life adversity and later health outcomes.
These are not just things like PTSD, although certainly depression, suicide attempts, substance
abuse, all were highly, highly related to the number of adverse childhood experiences
a kid reported or an adult reported retrospectively.
Things like heart disease, certain kinds of cancer, obesity, kidney problems, all of these
preventable to some extent, health outcomes were related to these early life experiences.
I think sometimes when people hear trauma, they think about a sexual assault.
Of course, that's one of the most traumatic experiences that someone can have in their
lives, but there's these whole host of other things that can shape the developmental trajectory
of a kid, who of course later becomes an adult in this case of founder, and shape the way
that their body processes stress, shape the kinds of choices that they make to try to
regulate their emotions in reaction to being upset.
There's this tower of dominoes that gets set into play that happens both on a psychological
and a physiological level that's very much shaped by hard things that happen to us early
on in life.
Of course, this is all very situationally and contextually dependent.
Kids who have a really hard upbringing do really well if they have a couple of great
important supportive adults.
In absence of any supportive adults, those kids of course struggle much, much more both
psychologically and physically.
Let's say that you're listening to this and you've had just a golden childhood.
Your parents were supportive, they were present, you didn't deal with any of this stress or
trauma inducing events early in your childhood.
Do you still need to worry about mental health?
Is any of this relevant at all or are you pretty much good to go?
Also, are you at somewhat of a disadvantage compared to founders who've been through
these things?
Sorry, you're not good to go.
I mean so much of the conversation about mental health, at least the way that I like to have
it is about prevention.
It's about knowing that to be honest, any of us have our own vulnerabilities, whether
that's in our personality, in the way our body responds to stressors, in our own history
of our psychological hurts or the bumps that we've experienced along the way, very few
people have an absolutely pristine life experience.
If you have had that golden child experience, in some ways you might be ill-equipped for
things that founders experience all the time, like a lot of criticism, like disappointment,
like failure.
If you haven't had a scrappiness to your upbringing, there might actually be some skills
that leave you vulnerable to mental health problems because you might be maybe less resilient
in the face of adversity.
I think one thing that can be hard for founders is when we're making bad decisions based on
these sometimes very subtle emotions or psychological issues.
A good example is I talked to Saranya Barak.
She's the founder of Code Newbie and she had this great insight a few years into her business
where she realized that in a lot of the decisions that she was making, she was optimizing for
making herself feel better and making herself feel more accomplished rather than optimizing
for making her business more successful.
Another example is if, say, you're a programmer, you might focus on programming tasks because
at least you know what you're doing in that realm and you can feel good about it and you
get these little shots of positivity and you might end up avoiding all these other important
tasks for running your business like sales and marketing.
If you don't even realize that you're making decisions this way, it can be really hard
to fix.
Is there anything that we as founders can do to be more aware of these underlying emotions
that drive our ability to make good decisions?
I think it's such an important conversation to have to recognize the deep entanglement
between who you are as an individual and who your business is as an entity.
For most founders, those things are not easily separated and that means that as your business
rises and falls, as there are highs and lows, so goes your emotional life, so goes your
sense of yourself and your identity.
I think the ability to be very carefully self-reflective about the things that you're avoiding, about
recognizing the difference between what your business needs and what you need, about sort
of counterbalancing that deep relationship that many founders have with their business
to try to diversify a little bit, to try to sort of buffer yourself from the roller coaster
so that your value as a human being isn't exclusively tied to the bottom line of your
business.
I know it can be pretty easy to underestimate all this stuff as a first-time founder, but
in your experience working with more experienced founders, do they struggle just as much or
do they naturally get better at dealing with it over time?
I think it's really hard to get a grasp on that.
I think even really well-established founders have a difficult time really appreciating
the depth of that relationship.
I usually see people really battling with it when they are approaching an exit, so highly
successful founders who are ready to sell their business and ride away into the golden
sunshine are realizing how very hard it is to extricate themselves from who they've become
in relationship to their business.
They and their business sort of become one, and so when you sell the business, it can
cause this pretty deep crisis of identity.
Yeah, we're talking a lot about the risks of you as a founder identifying too closely
with your business, but I think some might say that's actually a good thing, that it
helps you become more successful.
So what are your thoughts on that?
I think in some ways, it's fantastic, right?
You found something that you're pouring yourself into.
There's actually a research study that looked at the neurological activation that happens
in a founder's brain when they are looking at a picture of their child versus when they're
looking at an image of their business, and the neurological activation is really similar.
The areas of the brain that regulate positive emotion, sort of the blissfulness of love
are both highly active in both scenarios, the kid scenario and the business scenario,
and then the parts of the brain that are responsible for critical assessment for critical evaluation
are pretty inactive, they're repressed.
So both as parents and as founders, we're super biased towards our business.
We have sort of that love is blind phenomenon happening.
And I think that it's great in that it's fun, it feels good, it feels good to be attached
to something that you're making and to put yourself out there in the world.
I think it has a lot of benefits, but I also think that when you have limited resources
within yourself, and you put all of those resources in one activity, that does become
somewhat fairly psychologically dangerous, because of course, our businesses don't always
work out well, they do rise and fall.
And if we don't have other parts of us that can also be important and meaningful, then
we give a little too much power to our business to regulate our sense of worth and well-being
as a human.
And I love my business, but I need to have a separateness from it in order to be well.
Let's talk about that.
Because I love that not only are you an expert on these psychological issues, but you also
have your own business and you're a founder yourself.
So what is ZenFounder exactly and what made you decide to start it?
Yeah, so ZenFounder is a combination of different things.
It began with a podcast that I co-host with my husband, Rob Walling.
And we started doing that after...
So I gave a couple of different conference talks about mental health in entrepreneurs,
mental health in founders, and they were really, really well received.
And I gave those talks in response to a couple of high-profile suicides within the founder
community.
So Rob and I both observed that we had a number of friends in our entrepreneurial circles
who seemed to not be doing well, who were struggling with depression or having difficulty
in their marriages or their key relationships.
And we thought, okay, I'm a psychologist, I know a little bit about this, maybe I can
be helpful.
So from that thought, I gave some talks from the talks we started the podcast, which really
addresses more traditional mental health topics as well as prevention, how to stay well and
healthy in your family as you're running a business.
So we try to be fairly holistic with that.
And then that has created opportunities to do one-on-one consulting.
So I meet with founders individually, usually by Zoom, and try to come alongside and help
them solve mental health problems in their lives.
So it's not exactly therapy, but it's more consulting like, hey, keep an eye out for
this, or hey, have you noticed this pattern in your relationships with the people on your
team?
And we recently published a book called The Entrepreneur's Guide to Keeping Your Shit Together,
which is a culmination of a lot of that material, things that we've developed in the podcast,
things that I talk with founders a lot, that I talk with about one-on-one.
We've tried to pour that into the book.
So it's like this easily accessible things to think about as a founder related to mental
health and well-being.
That's a lot of stuff.
It's so much stuff.
I also do some group consulting, and we can talk about my unfocused business, but basically
I want to have as many conversations as possible about how to stay sane and well and still
kill it in your business.
Was there a point during this process where you decided this is more than conference talks,
this is more than a podcast, but this is an actual business that I want to be profitable
and that I want to make my living through?
I think that transition really happened about two years ago.
So my story runs somewhat in parallel to my husband's.
Obviously he was the co-founder of Drip, and Drip was sold about two years ago.
And as part of the acquisition arrangement, we moved from California to Minnesota.
So I left my clinic job and my teaching job in California.
And that was just a nice natural transition for me to have space and time to sort of build
ZenFounder and to make that more of the focus of how I was spending my time and energy.
And because I've been living with a founder for the last 18 years, I realized that as
much as I love academic work and loved a lot of what I was doing, I also caught the founder
bug a little bit and wanted a little bit more freedom and a little bit more decision-making
power over what my life looked like.
So it's been about two years that ZenFounder has been my primary focus and vocation.
Yeah, I think that goal of wanting to have control over your income and wanting the freedom
to work on the things you want at whatever pace you want or whatever schedule you want
is pretty much universal, at least among people who decide to become founders.
What was your initial vision for ZenFounder as a business?
Did you expect to generate revenue through advertisements on your podcast or through
speaking engagements?
Or did you just sort of let your business model fall into place over time?
Oh, I'm not even sure I have a grand plan now, but I think I do a lot of going where
I feel like I'm needed, which is not the best business model.
But I think there's a little bit of like a missional focus to ZenFounder that is maybe
different than a SaaS business or something like that.
So I knew that I wanted to write a book that's been on my bucket list for a number of years.
So that was something that was central.
And I think part of the end game is just growing as an authority and as someone who's the go-to
when folks are like, wow, I'm really having a hard time or someone on my team seems depressed.
Like where do I go?
How do I figure out information from someone who gets the founder life, but is also well
trained, not just like my wise aunt, Nancy or something.
So it's more I think about building a brand and the recognition of you want to talk about
mental health in the tech space.
I'm your person.
I know how to do that.
Let's talk about that because a lot of people start a business and they launch it and nobody
shows up because they haven't taken the time to really build an audience or a following
first.
And they really don't know what that process looks like.
So I'm curious how you've gone about doing that for yourself.
How do you think about making sure that people who've never heard of Dr. Sherry Walling find
out about you and come to associate you with the things that you want to be associated
with?
I do a lot of conference presentations these days.
And so that's a great way to have kind of a high impact interaction with a large number
of people.
I think when you see someone speak or when you meet them at an event, there's a kind
of quicker, deeper connection that you have the potential to build.
Guessing on podcasts, talking to folks, it's definitely like a word of mouth business.
And I think everyone that I work with individually as a founder, I've either met in person or
has been a referral from someone else who I work with.
So you're doing it right now.
You're marketing by coming on the podcast.
Right now, this is a marketing activity, I guess.
Great.
But I think so much of this conversation is about trust.
Like can I trust you with the things that I am nervous about?
So many people in our communities don't talk to a mental health professional because they
are worried about stigma, or they're worried about people thinking that they're crazy,
or they're worried that if they have a problem that feels unsolvable to them, that they're
a failure in some way.
I mean, there's so many barriers to having a hard conversation with someone you don't
know.
And so part of my job is to kind of be out there in lots of different ways and establishing
trust with as many people as I can to make it easier.
If people don't come talk to me, that's absolutely fine.
But to know that there are mental health professionals who are not crazy, who are actually approachable
and helpful and interesting, that's a big part of what we're trying to accomplish with
SendFounder as well.
Yeah.
I see a lot of this with indie hackers too, because part of the mission for indie hackers
is to get founders talking to each other about all sorts of business challenges.
And it's not just limited to very practical things like how do you market and find your
first customers, but a lot of it is psychological as well.
And some of my favorite conversations that happen online on the indie hackers forum are
when somebody says, hey, I just wanted to write a post and let you guys know that this
is really hard.
I've been struggling with my business for weeks or months or years, and I haven't gotten
anywhere.
And it's tough.
And I love when people make posts like that and others come in and say sort of words of
support.
What is the appropriate reaction when somebody shares that kind of information?
And how can founders do a better job helping each other?
I think one of the things that we all need to be probably better about is just really
listening.
Just because someone is coming to a group and saying, hey, I'm struggling.
It's really important to listen first.
And all of us have lots of good ideas, but one of the most powerful experiences that
is most helpful to people is the experience of being known and being heard.
So I would like to see that be a little bit better in a lot of the communities that I
bump up against.
It's not so much like, hey, are you exercising?
Are you backing off the caffeine?
Are you sleeping well enough?
Have you talked to a therapist?
I mean, all of those things are really great things to suggest.
But first you want the person who's like, hey, this is hard to know.
Yes, absolutely.
It's hard.
You're not alone in that.
And I really hear you.
I get what you're going through.
I've heard similar advice in relationship therapy and counseling, or if someone comes
to you and says, hey, this is my feeling, just how effective it can be to just repeat
back to them what their feeling is so they know that you heard them and you understand
them and they can feel validated in that way.
And sometimes that's all it takes.
Yeah.
And I think if you're going to give great advice, it's best to ask, to be like, hey,
I have a couple of suggestions for you.
Do you want my suggestions or is it more important that I just listen to you right now?
I think that's a question that we don't ask enough.
People are quick to dole out strategies and advice and it's not often the right time.
You mentioned that you had always wanted to write a book.
As part of your business, you were actually able to do that.
And in your book, you sort of distilled a lot of the lessons, a lot of the conversations
that you've had doing one-on-one consulting and then doing your research as well.
What are some of the biggest issues that founders deal with?
I think one of the biggest issues is really, in some ways, what we're talking about right
now is loneliness.
I think people feel really isolated.
Whether they're just starting out and they're working in their basement or whether they
are leading a team of 45 people, I think when you are the person who's making the decisions,
when you are the person who holds a vision for the company, it's very lonely.
And I think that there are lots of barriers to trusting other people with your journey
and with what you're really thinking about and worried about.
So I would say loneliness is a top one.
I think another thing that I end up talking a lot with folks about is fractured attention.
And this can be going through a day where you are simultaneously trying to respond to
Slack and email and watch for something that you've just posted on Product Hunt.
I feel like a lot of founders are cognitively all over the place in a way that over time
causes some significant damage to our ability to focus and be present and just do one thing
well.
Some of this is nicely articulated in Cal Newport's book, Deep Work, which many of my founder
friends seem to really struggle with.
One thing that's interesting is that if you look at what entrepreneurs are talking about,
if you go to the IndieHackers forum or if you go on Twitter, a lot of it is psychological
in nature.
But none of us are psychologists.
None of us really know what we're talking about.
So for example, one of the big topics that comes up over and over again is motivation.
How do you stay motivated?
How do you keep working on your business when the going gets tough, when you get busy, when
things get hard, or when you lose interest?
And it's a big one because ultimately, I think most businesses fail because their founders
quit working on them because they lose motivation early on.
How do you think about motivation in your own business and what do you see that works
well for the entrepreneurs that you spend your time talking to and counseling?
I'm a fan of habits and just good old fashioned like self-discipline.
And I think some things that help with forming good work habits are what we call context cues.
So you have workspace, you have work times, you have kind of a work ritual that helps
your mind know it's time to shift, it's time to focus on these particular topics and this
kind of question.
As opposed to like working in your bed first thing in the morning when you're not quite
awake or trying to work on your phone while you're waiting for your kid to finish up their
basketball practice, but really giving, carving out time and space that is a work time.
And people have different approaches to this, of course, but I think in some ways the more
structured the better, like putting your email time on your calendar so that it doesn't,
it's not amorphous, it's not always an option that you check email from 11 to 12 or a couple
times a day, you have a schedule and a routine and that you can, your brain and your body
sort of know what it's supposed to be doing at any given time because it's habitual.
It's also helpful to shift those habits every now and then.
So it's not like you set one pattern and that's the case for the rest of your work life, but
to have seasons where you work in the same place, you maybe listen to the same soundtrack,
you have these cues that say, okay, it's work time.
The environment around me as well as the environment within me are focused on work, which kind
of takes your emotional motivation out of it to some extent.
Yeah, I think one of the things that I've used myself tangential to this is this concept
of external pressure.
So when I first started Indie Hackers, what I would do every single week is I would email
my mailing list and I wouldn't just say, you know, here are the new interviews, but I would
also talk about what I'm doing with my business, what my plans are, what I accomplished in
the last week and it became this incredibly stressful exercise.
I eventually stopped doing it, but it was a lot of pressure every week to make sure
that I had accomplished something that was good enough to write to my newsletter about.
And I think on one hand, it was effective because I ended up doing a lot more work that
I otherwise would have done, but on the other hand, it was incredibly stressful.
How do you think about the balance between doing these things and making you more effective
as a founder, but that also takes some sort of a toll on you?
I love that kind of practice, especially for a time limited segment, like where you're
emailing your list every day, or I'm sorry, every week for three months and then you shift
to sort of a different external pressure.
I think sometimes we develop these structures that are designed to help us stay motivated,
but we hold on to them maybe too long and we don't give ourselves the space to sort
of renegotiate.
Actually, what am I really after right now, right here?
How am I growing or am I still just doing the thing that sort of got me to this point?
Sort of that, what got you here won't get you there phenomenon.
So most people function well with a significant amount of stress.
There's this old psychological finding called the Yerkes-Dotson principle, which is like
your standard bell curve or your normal distribution curve that looks at the relationship between
stress and performance.
And for tasks that we're pretty proficient in, a medium amount of stress is linked to
high performance.
I mean, that's the pinnacle of our performance.
So too little stress, no stress, no pressure.
It's like nobody cares.
You're not motivated.
Nobody's watching.
There's no fire under you to get things done, but your performance quickly drops significantly
once that amount of stress crosses over that sort of middle point and it becomes so much
stress that your performance just rapidly declines because the system is flooded with
stress essentially.
So you have to be super savvy about being able to read how much stress is the right
amount of stress for you, and then making a shift when it's becoming too much or too
little.
Yeah, this is why it's hard to be a founder, because you have to not only be savvy about
your business and the decisions you're making and whether or not they make financial or
marketing or product sense, but also manage your own psychology and understand, like you
just said, how much stress am I under?
Is this the optimal amount of stress?
Is it too much or is it too little?
And is that hindering my performance?
And it's a moving target, right?
You can figure it out one way for like six months and then you have to change.
Exactly.
On that note, what do you think are some of the differences between being an early stage
founder and a later stage founder?
Because I know that as an early stage founder, very often nobody knows what you're up to.
It's only you who's sort of motivating and pushing yourself along, whereas as you mentioned
earlier, if you're a founder trying to negotiate an exit or maybe if you have a large team,
everything you're doing is very public and people depend on you and it's a different
sort of job.
Yeah, I think early stage folks.
There's like a high scrappiness quotient, like just high energy, high excitement, lots
of passion, somewhat impervious to disappointment.
Hopefully at that phase, if you are able to do some really good long-term planning, you
have a good plan, but I feel like early stage founders are like surviving on adrenaline
and excitement and good ideas.
And then as you mature as a founder, that decreases a little bit.
You have some wins, hopefully, that keep you in the game, but you also have some discouragements.
You have more of a community that supports you, that understands what you're doing, but
you also have time to develop some competitors and some frenemies and some people that you
have more complicated relationships with as you go on in the founder circles.
So I think each sort of developmental phase of being a founder has its unique strengths
and its unique weaknesses, and you have different assets at one point in the journey than you
do at the other points in the journey.
When you're operating early on, you might not have much money to play with, especially
if you're bootstrapping, but later on in the journey, maybe you have more funds and you
can hire more people, but that of course introduces more and just different problems and challenges
to your work life.
Let's talk about some of the psychological challenges and hurdles that you've had to
get over and running your business.
Have you ever encountered any of these problems that you spent your time counseling other
founders about?
Oh, absolutely.
Yeah.
One of the times when I really felt my own, I don't know, I don't know how to say it,
when I was like, wow, I needed me to talk to me about this.
So when I finished the book, I got up the nerve, the gumption, whatever.
I had a moment where I was like, I wonder if Seth Godin would write an endorsement for
this book.
Wouldn't that be cool?
So I emailed Seth and I give him a couple of sentences about the book and he responds
right away and he's like, send it to me.
I was like, are you serious?
I was so excited and he wrote a really lovely quote that's on the back of the book, just
a very amazing endorsement.
I was riding high.
I was like, oh my gosh, I'm going places in the world, this is so exciting.
And then we get to book launch day and I'm so excited about the book and both Rob and
I emailed our list.
Rob's the second author on the book.
And so the email about the book goes out to more than 20,000 people.
And despite our best careful efforts, the link to the book, to go by the book was broken
in the original email.
And I was like, I have no business here.
I should not be doing this.
I can't even write an email accurately.
Who is ever going to take me seriously as an entrepreneur?
So it was just this really high and really low and all the voices in my head that went
from this is so awesome to you need to go crawl in the closet and hide from the world
because clearly you don't know what you're doing and you're really terrible at this.
So I don't get to be an exception to those highs and lows.
And I also definitely, I feel like I really read people well and understand people.
But the more that I work with other people and grow my team, the more that I learn that
I'm actually not very good at communication that I, you know, I'm not super detail oriented
in my instructions.
And so I'm learning all kinds of things about my own self as I grow as a founder and learn
how to try to put together a thriving business.
What are some of the things that you think you started out bad at that you've gotten better at?
I've definitely gotten a lot better at doing things in public.
That's hard at the beginning.
I remember the first few podcasts that I recorded, I went and rerecorded things.
And I was just like completely neurotic about making sure that everything was mapped out.
And now I, that's okay now, like I'm confident about just getting out there and trying.
That's become a lot easier.
So doing things in public is definitely something that started out hard and is much easier.
Well, let's dive into that for a second because I think a lot of entrepreneurs are in a situation
where they've maybe built something.
And the only thing holding them back is that they're afraid to put it out there.
They're afraid about how it's going to be received.
And they convince themselves that it just needs one more feature or just one more redesign
and then it'll be good enough.
Because they just are worried about what's going to happen when they start talking about
what they've done in public.
And obviously, this is terrible for your business because you need to be able to promote yourself
and promote what you're working on if you really want to get the word out there.
You're not just going to build it and have people magically show up.
How do you get over that hurdle?
And how do you get to the point where you're psychologically comfortable sharing what you've
done with the rest of the world?
I think the best way to do that is to just practice as much as you can.
And that means starting at local meetups.
And it means pushing yourself to whether it's speaking at your local WordCamp, which if
you do anything with WordPress or there are places to kind of get some practice that are
lower stakes, lower dollar investment.
And then I think you've got to have a feedback loop.
You have to have a couple of people who you ask to give you careful, thoughtful, constructive
feedback who you really trust.
And one thing that continues to be hard for me that I know is important is actually going
back and watching a lot of videos of me talking.
Or I do listen to my own podcast so that I can do some self-assessment.
That still feels somewhat awkward, but I do think it's important because every time I
hear mannerisms or I see things that I'm like, oh, this would be more polished if I didn't
say that particular catchphrase or if I didn't have that particular space filler.
So practice, practice, practice, have a feedback loop that you trust.
And then I think growing in your ability to take risks and be creative over time.
So I give very different kinds of talks now than I gave when I first started, when I memorized
everything and was like really, really careful. Now I'm much more comfortable just speaking
off the cuff for better or for worse.
But it allows me to accomplish a lot more in less time. Not because I don't plan or
don't think ahead, but because I'm just more comfortable with what I know is already in
my mind and my ability to recall it.
Yeah, I'm a huge perfectionist with anything that I put out publicly and it definitely
slows me down. It's a really difficult habit to get over.
Yeah. And I don't know, I don't know how much it matters. I mean, I think if you were to
really look at the body of my work, the podcast, anything I've written, talks that I've given,
things that Rob and I have done together, you're going to see a lot of consistencies.
You'll see the same message show up. You'll see the same, I think, sort of human approach,
the things that I value come across in my work.
And you'll probably see some of the same mistakes or foibles or inaccuracies in some ways. And
I got to hope that at the end of the day, there's some benefit of the doubt when you
just keep showing up and you try to be in as many places as you can that hopefully people
are gracious enough to overlook your ums or your slight mistakes to really hear the heart
of your message. Maybe I'm an optimist in that way, but that's what I'm banking on at least.
My stuff is not perfect, not by any stretch.
Yeah, I don't think anybody's stuff is perfect, even the perfectionists out there. So what
are some of the other challenges that you faced psychologically with your business?
Because I kind of stopped you after this first one.
I will say that a lot of the process of selling is challenging for me. Self promotion is hard.
That's not easy. I think, like many founders, my work is closely tied to me, to who I am
as a human. So hearing criticism is hard. It's still hard. And I think I'm still finding
my place in the world in the sense that I bridge these two disciplines. I'm a psychologist
who works a lot with tech folks, but I'm not a technologist. So I always feel a little
bit like I'm the outsider, which has its benefits for sure.
So I guess I'll say, Cortland, like, I don't feel like I've come to this point in my career
with like, lots of boxes checked off. I feel like the thing that I have done by this point
is to be self reflective enough to know when a particular vulnerability or sensitivity
is getting activated, and hopefully faster at catching it and knowing what to do about
it than maybe I was earlier on.
How do the rest of us do that? Because I think it could be very easy for these feelings to
sort of exist below the point of perceptibility and then to just sort of magically appear
one day. It's easy to not know that you're burning out until you're burned out. It's
easy to not know that you're afraid to launch until six months have gone by and you haven't
done anything. How can the rest of us develop the same sort of psychological sensitivity
that you have and catch these things before they start to get really bad?
I think there are two sort of areas where you want to collect data. One is to really
pay attention to your physical body. Sometimes our emotions exist in our bodies before they
exist in our minds in a way. So if you're someone who sleeps pretty well but you're
not sleeping well, then it's a really good indicator that your anxiety is too high or
you're bothered by something. If I'm in a conversation and I find that my throat is
tight, like I'm not breathing very well, like that the muscles in my throat and chest seem
to be contracted, then that's a sign that like, oh, something is funky here. I'm either
having some complicated feelings or I'm stressed out. So each of us have our own physiological
indicators that something is not well. And again, for most people that sleep it's muscle
tension, it's constriction in our throat or soreness in our shoulders. It sort of says
like, wow, I'm clenched. I'm holding something too tightly. So paying attention to those
kinds of things can be super helpful. I also think that paying attention to your own emotional
nuance. I generally like people. I don't feel particularly defensive or judgmental.
I generally like people, but when I'm finding myself having some negative thoughts and feelings
about someone else, I have to sort of pause and ask myself like, why am I bothered? What
am I reacting to in this person that is causing me to think or to feel this way? So you become
the sort of investigator of your own inner world, but first you do have to pay attention
to the cues that sort of signal little tiny red flags. Once you see those red flags, then
you can do some investigation. And that's where something like a journal is a really
powerful tool to write on a piece of paper, like why am I bothered by my conversation
with Cortland? What am I holding onto? And just give yourself some kind of free emotional
space to try to sort through why you might be feeling the way that you feel about that
particular incident or event.
Dear journal, that Cortland guy is a real asshole.
I got to go journal. I also think that that's another place where having a coach or a therapist
or a very like learned listener in your life can be a really important asset for you to
just open a conversation and say like, I'm feeling a little funky, I'm feeling off and
I'm not sure why. And they can kind of help you try to unpack why you might be feeling
that way.
So let's talk a little bit more about your particular business. Do you ever worry about
the scalability of what you're doing? I know you said you're not a traditional SaaS business.
You're a little bit more mission driven. And you're providing a lot of personalized help
to people, which I think is very high in terms of impact. But also, there's only one of you
there's only so much Sherry to go around. How do you think about balancing the number
of people you want to reach with their business and the level of impact you have on each individual
who comes into contact with the Zen founder?
Yeah, it's something I think about a lot because, you know, at the end of the day, I don't want
to spend my life trading, you know, hours for dollars, like I'd like to have something
that can that it has some scalability. And so I kind of think about it like a pyramid,
the one on one consulting being at the top, that's like the highest dollar, it's also
the highest impact, but it's time limited, it's limited only by what resources I have
available to give to someone.
And then underneath that is some group consulting, leading a retreat, doing an event that impacts
more people, but it's still a big draw on my time. And then you go kind of down the
cycle and down there is blogging, it's the podcast, it's writing, it's things that aren't
necessarily like deep high impact between me and one person or me and a small group
of people. But it's putting the word out there, it's getting good material out there to a
much broader audience than I could, you know, ever hope to interact with one on one or...
So I think as we are moving forward, we're also thinking about some ways to develop some
courses and things that are easily accessible to folks that don't require, you know, the
cost and time intensity of doing a round of one on one consulting with me.
Yeah, I think that's an interesting approach because a lot of founders come into this with
the end goal in mind right from the beginning. And so on day one, they're trying to launch
some sort of infinitely scalable SaaS app that's going to, you know, make money on its
own while they sleep. And that's hard to start off with. I think the path that you've taken,
which is a lot more hands on, a lot more sort of hourly, at least at the beginning and then
gradually shifts towards something that's more scalable is probably the more realistic path.
So are there any bumps in the road, any sort of unexpected challenges you've run into there
that you would advise other founders to watch out for if they decide to follow in your footsteps?
And also, is there anything that's good about the way you've done things you think others
should copy?
Yeah, I'll speak to the second question first, at least for me. And, you know, this is, I
think, highly dependent on the kind of work that I do. I mean, the day that I stop doing
one on one consulting entirely is probably the day that people should stop listening
to me. That my deep expertise comes from the practice of really going deep with founders
and listening well. And if this becomes too academic, and I am so much about product that
I don't have time or energy to do a deep dive with at least some people, I think that that
will severely decrease my authority and my ability to be effective. It puts me too detached
from my customer, so to speak, which again, for my business, for what I'm trying to do
is deeply important. So and I know that can look different in different businesses, but
it's the CEO who occasionally takes a support call because you just have to be able to be
in a place where you can really hear the deep needs of your customers and appreciate the
challenges that they're experiencing. So it's like you never want to get so removed from
where you started, that you really forget about the thing that started you off in the
first place, or the needs of the people that you're serving. So I feel really strongly,
I don't need the income, so to speak, but I feel really strongly that the consulting
piece continues to be really important to who I am and what I'm able to provide.
I think that's something that should be universal to every founder, and every business, you
always want to stay very close to understanding who your customers are, and what it is that
they want. And I guarantee you that if your business is successful, there was a point
where you understood that stuff very well in the beginning. But it's easy to lose track
of it over time, because, you know, the realities of your company start to build, right, you've
got urgent bugs that need fixing, you've got features that you need to take care of, you've
got all sorts of things that have a very obvious and immediate payoff if you work on them,
whereas talking to your customers and staying in touch with their needs and their desires
doesn't seem to have this immediate payoff, and so you can neglect it. But then over time,
the world can change. And, you know, you look up two or three years later, and what your
customers want is different, or, you know, your skills and your knowledge have deteriorated
and you're making these asinine decisions for your company and your business. So it
takes a lot of discipline to do, I think, what you've done and make sure that you stay
in touch with your customers and you keep talking to them, even when your business is
pretty mature.
It also keeps me really close to the heart of what I love. You know, I always feel for
the designers that are so successful that they like move out of actually designing anything.
And often they're fine with that, right? It's a calculated choice. But for me, I think running
the business without the kind of deep connection with a couple of folks, or at least a handful
of clients would take me too far away from my personal superpower and what it is that
kind of gives me life in my work.
So what are some of the things that are perhaps difficult about trying to transition from
a more consulting-based business and do something that's more scalable?
Oh, I'm kind of all over the place. Like, I think that's the challenge is like there
are so many things that I'm trying to hold up at one time. So do writing, promote a book,
keep up with, you know, I just blog like twice a month, keep up with a weekly podcast. I
mean, it's just sort of the number of things that I have my fingers in and in any given
week is definitely a case for not being particularly focused or not being particularly awesome
at anything.
So add to that, of course, like parenting children and being a wife and like trying
to have friends and stay in shape and all that stuff. So I think, you know, in some
days if I could just like do one thing, if there's only one component to my business,
it would be so much better for my sanity. But alas, that's not how it's going to work
for me as I add different components and build out different things.
There's just a lot of growing pains. And I think for me, as with many founders, that
growing pain looks like fragmentation. Like it's just not as focused as I would ideally
like it to be.
Okay, so you're trying to get your business moving in the right direction to make it more
scalable so you can, I guess, make more money by doing less work to any of the activities
that you're doing. I mean, you're doing public speaking, consulting, you got a podcast, you've
written a book, you're doing retreats. Any of these things stand out? Are there any outliers
where they're disproportionately effective? Or maybe they're disproportionately time consuming
and you wish you hadn't done them?
Yeah, I think I loved doing retreats. The last retreat that I did, I planned with some
co-facilitators and none of us were professional retreat founders or sort of retreat planners
or event planners. And I will never do that again. I will only have an event planner do
any future events that I do because it was just so much bandwidth and time and energy
like picking menus and working out room spaces. And it's like, oh, this is not, I'm not good
at that kind of level of detail. And I'm not, it doesn't excite me like I don't like it.
So it took a lot of energy to put that together. And really, it was a case where I should have
just hired someone who is way more efficient and has more expertise than me to do it for
me.
On that note, why don't we talk a little bit about hiring? I know you've got people helping
you with SendFounder. How many people are helping you exactly? And how did you go about
finding them and convincing them to join your team?
Yeah, we have kind of a cast of characters that help us. And most of them have come on
board through word of mouth, like our audio editor for the podcast, for example. I have
an assistant that we just found on ODesk and I've been trying out and increasing her sort
of authority over my life as I work with her more. And I would say that hiring has been
something that has been harder than I thought, especially because, so in my previous work,
I hired junior clinicians who worked at the clinic where I was a director. And so I have
a lot of experience interviewing and hiring, but the job was always pretty well defined
and didn't require a lot from me. It was sort of like, here are new psychologists, here
are your clients, go and do your work. There was more to it than that, but they were experts
who sort of knew what their job was. And here I'm bringing in folks where I am practicing
how to explain the details of exactly how I want the podcast to be done and what I want
the tags to be and the categories to be and all of the things. And I'm learning that,
again, my attention to detail in communication is not awesome. It's a whole skill set that
I've had to learn in hiring, which has been somewhat of a surprise for me.
I think it's interesting that you're doing a lot of things that can be immediately profitable.
It's not this long, slow revenue ramp up that many people with SaaS businesses have. If
you're doing public speaking or you're doing retreats, people pay you immediately, which
means you have the funds to hire immediately if you really want help. You've been hiring
a lot of Odesk and things like that. What have you learned about this hiring process
that other founders could learn that could help them hire more effectively and find the
right people and do a good job communicating with them?
Yeah. So one of the challenges that I experienced and maybe one of the cheats that I use is
the fact that I'm operating at a level of success that's probably more commiserate with
my life as a psychologist than my life as a founder. And so there's a lot of things
that I don't know and I'm not good at that are more technical, which means I bring in
a lot of help. I bring in help from my friends who are founders. I was talking with someone
about doing some SEO help for my site and I'm like, honestly, I really don't understand
this very well. But I have friends that do. I have friends that are experts in this. So
they reviewed the person's content material and they looked it over and they said, oh,
this doesn't sound quite right. Ask about this or ask these questions. So in a way when
I'm hiring, I have a first pass with someone who I know who I'm friends with who is deeply
successful in whatever content area it is because there's a lot about being a technical
founder that I know nothing about that I'm not good at at all. So I have an acute sense
of my weaknesses and am really good about asking for help, which I know is not the case
for everybody. But because I have kind of a deep network at this point, I've been grateful
for people to review a lot of the potential hires that I've had. And of course, my husband
Rob is great at that. And so he does a lot of this with me. He's also involved in Zen
founder alongside me. So we do some of that together.
A lot of people who listen to the podcast are not programmers. They're not technical.
And as a result, they have a lot of trouble building sort of a reputation and credibility
and also practical things like a website for themselves. You're also not technical. And
yet you've been able to build a huge presence for yourself, a big audience, and a beautiful
website. What are your tips for non-technical people operating in the web space? How can
they do what you've done?
I think having good help is important. Having a lot of people review your site, for example,
I think I'm amazed at how people see things that I don't see, whether it's in the copy
or in the design or in the functionality. And I have found it hard sometimes, but really
important to just be humble enough to say, hey, what do you think of this? How does this
look to you? What bothers you about this?
And it's not always great to hear that feedback, but important. So I'm in a couple of mastermind
groups with people who are more technical than me. And they'll look at my stuff and
give me two pages of feedback. And it's painful sometimes because I feel really stupid, but
they do. They see things that I don't see. So I think asking for help, being humble enough
to take feedback, realizing that you can't possibly see or know everything about your
work is really helpful.
And then again, that practice of just getting yourself out there over and over and over
and being on podcasts, asking people to be on your podcast, guest writing on things,
asking people to write for you. One of the things that happened recently that I was really
excited about was I got asked by Stripe Atlas. So many of your listeners are probably familiar
with Stripe. They have Atlas, which is a series of resources for people who are starting online
businesses. But they asked me to write a guide to stress management.
And it's a really nice little way to get my name out there for a lot of folks who come
across Stripe's work. But the only reason that that happened is because seven years
ago at a conference, I met patio 11 or Patrick McKenzie. And I've seen him a couple of times
and I follow up and we're friends on Facebook. And when you show up over and over for a long
time, people notice. Also a part of that is showing up well is making sure that as you're
building your network, you're paying attention to who people are and being good to them,
being curious that you're not a jerk at a dinner, that you're not entitled in a conversation
that when you're meeting people, you're always on, you're always gracious, you're always
listening well.
I know this sounds like maybe a tangent from your question, but the way to grow an audience
is to be someone who's engaging and connectable, someone who people want to connect with. And
that takes a long time.
I think all of that's great advice for everybody, not just non-technical founders. One thing
that's interesting that I've seen on Indie Hackers is somebody will come onto the show
or they come on the website, they'll do an interview, and they'll just talk about what
it is that they're doing with their business. And very often I hear these same founders
come back and say, Coraline, you won't believe what happened. We closed this deal, or we
made this sale, or we made this hire, or we got acquired, or we got this great advice
because somebody reached out after reading our interview.
And I think half of what's going on is that if you come out and you share your story and
people find it helpful, then they want to help you back. They want to reciprocate.
But the other half of what's going on is that if you tell your story and you share all these
details, then people know how they can help you. They don't have to guess. I mean, you've
written it down exactly what you're trying to do. And so they're like, oh, I'm good at
that. Let me help Sherry with that problem that she's having.
So I think in addition to helping other people, it's a good thing to get in the habit of just
talking about what you're doing in public so others can see. Anyway, we're approaching
the end of our time here. Sherry, is there anything from your book or from your work
that we haven't touched on that might help fledgling founders become more successful
with their companies and be a little bit more psychologically healthy while they do it?
Well, I think hopefully the folks that are listening to this have connection beyond just
listening to the podcast. But being part of a forum like IndieHackers, being somebody
who goes to events every now and then, being someone who's cultivating a couple of friendships
with other founders, I think is really, really important.
When we think about the going back to the trauma literature, maybe where we started
coming full circle, if you in your life are going to go through a terrible thing, traumatic
bereavement, the loss of someone, an assault, just something terrible, the one thing that
has consistently been shown to be the most important protective factor, so the thing
that helps decrease the likelihood that you'll have a bad mental health outcome, the one
thing, the one asset that you want available to you is a couple of good relationships.
You don't have to be the bell of the ball. You don't have to be the person with the biggest
network, but you want a couple people that care about you, that know the details of what's
going on in your life, that will bring you a sandwich at the hospital or will fly across
the country to attend your dad's funeral with you if that's what you need.
Those people are not always easy to find, but when you put yourself in communities like
Indie Hackers or other places where you're bumping up against people who have similar
interests and similar goals, that's a great place to develop those kind of deep lifelong
friendships with folks who are going to see you through the ups and downs of whatever
your journey ends up being as a founder.
I couldn't agree more. Well, thanks so much, Sherry, for coming on the podcast. Can you
tell listeners where they can go to learn more about what you're up to personally and
about ZenFounder as a business?
Absolutely. I live on the internet at zenfounder.com. That's where you can find out about the podcast
and the book and articles that I'm writing and whatever else. I also have sherrywalling.com,
which houses my therapy practice and information about my background and work in the psychology
world.
It's been such a pleasure, Courtland. Thanks for having me on. I'd be happy to be a resource
for any of your listeners as they have questions or mental health kinds of needs.
All right. Thanks again, Sherry.
Take care.
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