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Adam Fishman (author of a top business newsletter on Substack with 11K+ subscribers) interviews executives, entrepreneurs, and company leaders in technology companies who are also fathers. They discuss the tough aspects of work, parenting, family, the mistakes made and lessons learned along the way. All episodes at www.startupdadpod.com.
Especially the court system can
get you drawn into the conflict.
This desire to win, the
desire to make right.
You know, your attorney might
even say, well, you can go after
this and this, and you should
do this, and you'll, you'll win.
And you know, at the end of
the day, there is no winning.
And just if you remind yourself of
that, that sometimes it's okay to let
the other side win, if it meant that
you could spend an extra set of weeks
with your kids, right, just in presence
rather than in the court system.
Welcome to Startup Dad, the podcast.
We dive deep in the lives of
dads who are also leaders in the
world of startups and business.
I'm your host, Adam Fishman.
Parenting can be hard enough,
but navigating divorce and
separation, then co-parenting.
Is something people usually
don't want to discuss.
To talk about life as a co-parent,
I sat down with Saul Kennedy.
Saul is the founder of Best
Interest, a product he's built
to help co-parent navigate the
messiness of that relationship.
He was inspired by his own
challenges with co-parenting.
Saul is a serial founder who is
built and sold multiple companies.
He's also been a head of product at
Dropcam, product manager at Google,
and an angel investor in companies
like Coinbase, GitLab, and Instacart.
In addition to being a serial
entrepreneur, he's also a single
halftime dad of two kids and a co-parent.
In our conversation, we spoke about
navigating divorce and co-parenting,
important lessons that Saul has
learned from that experience.
The emotional rollercoaster of
halftime parenting as a single
dad and his experience taking
time off to be a full-time dad
when his daughter was very young.
Saul shared a mistake he made as a
parent and how that experience has
helped him grow into the dad He is today.
I hope you enjoy today's
conversation with Saul Kennedy.
Welcome, Saul Kennedy to startup
Dad, Saul, it's a pleasure
having you here with me today.
Thanks for joining me.
Thank you, Adam.
It's great to be here.
So for folks who don't know much about
you professionally, we're obviously
gonna get into your parenting journey,
but tell me a little bit about you and
what you do for work and what you've been
doing for the last couple of decades.
Yeah, I've always been an
entrepreneur and that's how I
identify, is I start companies.
And I started my first company
when I was 15, kind of did that
whole thing, and I've always been
attracted to creating software.
So my first app was a popup on
your Windows or Mac computer.
Way back in the old days on startup,
and it would be an inspirational
message that would pop up.
And that's my career is I
love starting companies.
I love starting from scratch,
learning how to do it all myself,
and then growing a team out of that.
And so, yeah, that's what's
brought me to today, being a dad
and also running best interest.
Cool.
I can't wait to talk about best interest.
This is gonna be really, really
fun and a unique conversation we've
never had on this show before.
So tell me about your family now.
You are a single dad.
I am, yeah.
I have two kids.
They're six and eight.
Great little kiddos.
We live in Northern California and
yeah, I am a halftime dad, so I have
custody, joint custody with their
mother, and I have them half the time
and typically during the weeks we split
it 2, 2 5, which means they're kind of
shifting back and forth during the week.
And then the, in the summertime
we do week on, week off.
That's how we split up the custody.
And I have a, a wonderful partner,
Louise, who's really actively
involved in the kids and helping
out and yeah, that's the family.
How old
were your kids when you went
through the divorce process?
And tell me a little bit
about that experience.
Yeah, so the process of our marriage
unraveling started pre covid, and
fortunately in hindsight, actually
a week before the lockdowns of Covid
was when we decided to separate.
And it was definitely a challenging
time to be shifting from being married
to then being single and not being
able to meet anyone, not really
being able to socialize, having
lockdowns negotiating, how do you
manage kids when there are lockdowns?
That sort of thing.
It was definitely an intense time to
be learning the ropes of co-parenting.
Yeah.
And your kids were, I mean,
pretty young then, right?
Like if I, yeah, if I'm thinking
about back like five years ago,
they were like one or two and three.
One and a half,
and three and a half.
Yeah.
Yeah.
So how do you have that
conversation with kids at that age?
Like they understand.
So little it would seem, so
I'm curious, like what is that,
like, how do you approach that
with like really little kids?
Yeah.
Or how did you, I guess?
Yeah, that's a really good question.
And yeah, I don't have
all the answers for sure.
You know, but what's interesting
when they're getting started on
this journey themselves so young, it
just becomes their normal, you know?
And we kept it really simple.
Daddy's getting a new house, mommy's
getting a new house and we're moving
and then we're gonna each have
houses and you're gonna go back.
It was very simple and it just,
like I said, it became their normal.
And these kids are so flexible, you know,
I think divorce is hard on kids for sure.
But in the case of our kids.
They're like very just
okay with this dynamic.
They don't complain about it and
they just have their systems.
And what's also really interesting
is that their relationship is even
closer than they are with each of
their parents because they're always
spending time together, transitioning.
And I really love that, that they're
such good buddies in this process.
Yeah, that's sort of interesting that
the only constant for them is each other.
Yeah.
So, yeah.
Wild.
Yeah, it really is.
So you went through this divorce
process and now you're co-parenting.
And you mentioned to me that co-parenting
and the reason you've built this company
best interest co-parenting has been
more challenging, more challenging
even than the divorce process.
So tell me a little bit about
that and what have you learned in
navigating this process so far?
Yeah.
You know, I never thought that I would.
Get divorced, I don't
think anyone ever does.
Of course.
And facing the idea of divorce and
co-parenting, I was really terrified,
you know, about starting over.
And the divorce process actually
in hindsight and now knowing what
I know about what other people go
through, ours was pretty simple.
Like you mentioned.
It was fairly straightforward.
We mediated most of it,
and so I have a lot.
I thank us both for being able to
take the high road in that situation.
Afterwards though the co-parenting
was the most challenging thing for
us, and what ended up happening was
that I noticed we were just constantly
getting engaged with one another,
especially around communication.
This was actually when I started
getting back into dating.
My first girlfriend at the time
made just this nice, gentle
acknowledgement and observation
that I was texting my ex a lot.
Mm-hmm.
And I, at that time thought that
was normal, you know, to be texting
five to 10 to 15 times a day.
And then I realized actually
that's not the right way.
It's not the right way to move on.
There's a certain amount of communication
that's necessary, obviously as a
co-parent and there's some that isn't.
And a lot of times the messages were
taking me outta the process of being
a dad, you know, being present with my
kids and also moving on with my life.
And so that.
Became the spark, as you mentioned,
of the business that I'm building
now, which is helping co-parents
communicate with one another.
Yeah.
And you described to me just the, this
sort of adversarial system that exists.
Tell me what you meant by that.
Well, yeah, so the family court
system, I'm not a big fan of it.
As a co-parent, I have experienced what
I would describe as the underbelly of the
family court system where a very, very
simple matter became incredibly complex.
I was on the stand for many hours in a
situation that really could have just
been solved with a simple conversation.
And in the family court system, it's
rooted in the court systems of this
country and that there are winners
and losers and there's good and bad,
and we have to assign blame and we
have to decide who is right and.
When it comes to families and
kids, honestly there are no
winners in this type of battle.
And so I ended up walking away having
won the decision, but feeling like I
had lost because it was such a time
consuming and awful process for everybody.
And so some of the impetus and the desire
and the prayer of my current company is
that we can save other co-parents from
going down that path and ending up in the
arms of the family court system, which
I don't think always protects people.
Yeah.
Oh, I hadn't even thought about that.
That you know, we have this system
that's de that's really designed
for punishment and we're trying to
figure out something that's supposed
to be equitable and like, you know,
it's partnership even in separation.
And so that's really challenging.
Yeah.
And there are no criminals here, right?
We're all trying to do the best we can.
We're all trying to be the
best parents we know how to be.
And you know, really at the end
of the day, a system like this
takes people away from their kids.
Yeah.
And in the court system, you hear the
term best interest, always referring to
what is in the best interest of the kids.
And so when I was coming up with the
name for my business, I thought, oh,
that would be a pretty good name.
To remind people that it's
really about the kids.
Yeah.
Oh, that's really interesting.
I was wondering how you
came up with that name.
That's good.
If you had like one piece of advice
having navigated the court system and
just generally with co-parenting kind of
broadly, what would you tell someone who's
like going into this journey themselves?
You know, learning how to take the
high road and also specifically
learning how to drop the rope.
And I'm not always the best at this, but.
Especially the court system can get you
drawn into the conflict, this desire
to win, the desire to make right.
You know, your attorney might even say,
well, you can go after this and this and
you should do this and you'll, you'll win.
And you know, at the end of
the day, there is no winning.
And just if you remind yourself of that,
that sometimes it's okay to let the other
side win if it meant that you could spend
an extra set of weeks with your kids.
Right.
Just in presence rather
than in the court system.
Yeah.
So I think that that is the key
is just learning how to not win
and to just allow and accept
and move on.
It sounds like just not even
getting into the battle that the
court system or the lawyers want
you to have is a good piece of
advice too.
Oh, totally.
And you know, that's, uh, again,
that's just really what I believe
best interests purpose is, is
that for me, it started with.
Communication breakdowns and, you know,
blaming each other and getting defensive,
and then, you know, 30 texts or later
you're, you're up in arms, right?
And, and that's not helpful for anyone.
But learning how to communicate
effectively with one another
to ensure that your message
gets across that conflicts are
deescalated, that can really help.
Because in a co-parenting dynamic,
it's a such a weird relationship.
If you've never been a co-parent,
you don't really know how
uniquely challenging this is.
Here is this person that you literally
decided you don't wanna be in relationship
with any longer for whatever reason.
You know, there might have been something
really traumatic too, in that there
might even have been emotional abuse
or whatnot, and yet now you're forced
into a relationship with them that.
Isn't any better.
You both are the same people and now
you're having to navigate and make
really important decisions, highly
emotional decisions with one another.
It's one of the most challenging
human relationships that
I think anyone can have.
Yeah.
Wow.
That framing is really interesting.
You, like, you've knowingly
decided that we don't wanna
spend time together anymore.
Yeah.
And yet you have to, right?
Yeah.
You like have to negotiate and navigate
all this stuff that's challenging.
So you're a si, you're a
single dad, halftime parent.
Tell me about that experience.
What kind of feelings,
like, what's that like?
Yeah.
I appreciate that question.
You know, it's a unique thing
to be a halftime parent.
You have this experience or
I have this experience of.
When I'm with my kids, especially
when it's just me and it's two on one,
honestly, that can be really challenging.
The ages, my kids are like, it's
getting a little bit better,
but man, there's so many demands
and it's overwhelming at times.
And so a lot of times I have
this feeling like, oh, I need
a breather, I need a break.
I need some adult simulation.
You know, especially during covid.
It's like, where are my adults?
I'm surrounded by kids,
and gosh, I need a break.
And then you get your break and you're
like, oh man, I really miss my kids.
Oh, this is awful.
Like I can't see them,
I can't talk to them.
I have to pretend like
they don't exist in a way.
That's hard.
It's weird to go from this.
It's like a black and white kind of
experience of, okay, now you're single,
you're back to hanging out with adults.
Oh no, you're back to being a
dad, you know, and back and forth.
Oh, the kids are sick now.
The schedule's adjusted.
You know?
Yeah.
So it can be really, it
can be really challenging.
It can be really lonely to be doing that.
You know, post Covid, obviously
it's changing, but we live in a
culture that we're not tribal.
We're all living in our own homes,
and we're all doing the parenthood
thing pretty much solo, unless
we're making extra effort to get
everyone together and do play dates.
So it can be pretty
isolating to have kids.
Yeah.
That.
What you described is like a
rollercoaster ride of like, I'm
on, oh, I'm off, I'm off, I'm off.
I'm on, I'm off.
What a wild feeling.
Yeah.
Yeah.
There's like a splitting that happens too,
where like I almost feel myself putting
on the daddy cap when it's like that day
I, I know that they're gonna come and
my personality shifts subtly, you know?
Yeah.
Probably even hormones get ready,
you know, like I'm ready to get in my
daddy mode from being a single guy.
Yeah.
The thing too that you mentioned is,
you know, six and eight, you know,
it's not newborns so you know, you're
not changing diapers and things like
that, but six and eight year olds,
and I think you have two boys, right?
A girl and boy.
Boy girl.
A girl and a boy, okay.
Yeah.
But still since that age, you have to be
on all the time when they're around, like
they wanna do stuff, which is amazing.
You know, I hear stories about like
the teenage years when they don't
want to see you at all, but it's also.
Like, I think it's okay to also
admit like, it's also exhausting.
Oh yeah.
I wanna admit those sorts of things
because, you know, I know it's not
normal to, you know, like a lot of people
won't admit to being bored when they're
around their kids, but honestly it can
be really, you know, boring to keep
playing the same game over and over again.
That can be really hard.
You know, six and eight is a
unique time where especially my
8-year-old, she's starting to be
a lot more independent, you know?
And like, she dresses herself
now and that's been a while.
But, you know, she'll get up on her own.
She'll come in on her own, like
there's kind of this independence.
She'll be doing her art projects,
she's a great artist and she has
her own life that's developing.
Whereas my son, he's still very much
in, like, he wakes up, he comes to me,
he wants to play a game, he wants, he's
like dictating what we're gonna do next.
And as his dad, I'm learning, well,
how do I. Set boundaries with him so
that I ensure that I have my own time.
And there's also this guilt of being a
co-parent knowing that, well, actually
I will be getting my own time because
you're going back to your mom's today.
So then I feel guilty even
setting those boundaries.
So that's also an interesting
aspect of being a co-parent, is how
do you maintain those boundaries
with your kids?
So it's hard enough to maintain boundaries
with a 6-year-old and then, you know,
he doesn't get to see you all the time.
And so it's probably like very
intensely, like, I wanna do all
the things with you right now.
Have you developed any strategies for that
or stumbled through figuring this out?
Stumbled through is a great way to put it.
I think, you know, in
terms of being a dad, I.
I like to just be really calm
with them and I'm just, I'm
generally a pretty grounded guy.
That's just the way I show up in
life and that extends to my kids.
And you know, sometimes you have
this experience as a co-parent that
sometimes the other house is a black box.
You don't really know what's going on per
se, depending on the communication level.
And then they just arrive and then they're
just filled with energy and you hear a lot
about like, oh, they come back so crazy
from their dad's house or their mom's
house and what's going on over there.
Sometimes the kids are just really
excited, you know, they're really
excited to see you again after.
And that's the way they're
expressing their excitement is
by being absolutely bonkers.
And so for me it's about
creating those rituals.
So I do a, a little ritual with
them when they come back home
where, yeah, it's a little woo
woo, but I'm a kind of a woo guy.
We do a little ritual where we gather
and they each pick out a crystal in
our object from, you know, the room.
And we get together and we just
talk a little bit about what
happened and you know, what we're
gonna do the rest of that week.
And as a way to just kind of ground
into each other, welcome them back, and
then, you know, say you're here now.
I think that's important to have
that ritual so they are able to
like say, okay, we're here now.
We're all
together.
It sounds a little bit like I. The circle
time that they do in school to kind of
set their intentions for the day and like
to talk about what are we gonna do today?
You're doing it, you know,
what are we gonna do this week?
Or whatcha are gonna do while you're here?
But that seems to work
pretty well in school, so.
Totally.
Yeah.
Yeah,
that's a very similar approach.
And I also just, you know, when
it comes to being with them, I
just really like to be patient.
You know, they might be going through
a lot that I'm not even aware of.
Right.
And so it's about being patient
with them and taking things slow and
just listening to what they wanna
do and just being there with them.
That is one of the benefits of being a
co-parent, is that I do have the benefit
of being able to be a little bit more on,
because I've had sometimes a week off.
Where I've been able to, you know,
really focus on me time and renewing
myself, and then I can show up with my
full energy and I'm not so worn down.
So that is another benefit
of being co-parent.
I actually, I wish that more married
couples would give each other time off.
I think that would be very beneficial
to marriage to allow each individual
to remain independent from their
kids sometimes, because it can be
a slog when it's the two of you all
the time with the kids all the time.
Yeah.
Yeah.
I am curious, you were in the fairly
fortunate position of being able to take
some time off to be a full-time dad.
Oh my gosh.
For, for a period of time.
Yeah.
And then you went back and started a
company, which is like the polar opposite.
So I'm curious about both
ends of that spectrum.
Why did you decide to be
a full-time dad or maybe.
That decision was made for you
and then, you know, what made
you take the leap back into
company building?
Gosh, I mean, the company building
first, just to say, I mean,
it's a bit of a compulsion and
we'll return to that, right?
And just to be honest here, but the
taking the time off, you know, the
way that my career had gone, I've
always been a small startup guy.
That's what I really like doing.
It's the most fun for me being able to
put out the fires and put on the hats and
not really worry about politics and stuff.
Well, I ended up through an acquisition
and then another acquisition at a
big company at Google, and I thought
going into it, this is my dream.
I'm at big company, great healthcare,
and sure enough, you know, great
healthcare, I meant kids and all that.
Like it felt like the right time and,
but I really didn't like the job.
It wasn't my cup of tea.
Like it was very political
as a lot of companies are.
You know, no dis in Google.
They're a great company.
But it was difficult for me
to be in that environment.
I was not being an entrepreneur
in that moment in my career, and
I've always known that I wanted to
be a dad always since I was a kid.
I just had that dad vibe.
Just always had that.
So when I knew I wanted and
I was ready to be a dad.
I knew I wanted to jump in and have that
experience and just do it wholeheartedly
like I do all my other projects, like make
that my startup basically was the idea.
Yeah.
So I decided to quit my job after
my daughter was born, you know,
eight and a half years ago now.
And I thought that was gonna be
maybe a year sabbatical, and then I
was gonna get back, get re-inspired,
and that inspiration didn't come.
You know, I, I was so focused on being a
dad, that was my inspiration and honestly
very overwhelming being a full-time dad.
I developed some very good empathy towards
people that choose to do this towards my
mom who did this for my whole childhood.
It's a lot of work, it's very demanding,
and yet I wouldn't take it back.
All the memories that I had just
being with her during the day and
like having that connection of, I.
Being able to see her wake up in
all of her stages of development.
It was just, it was so beautiful to have
experienced that, and I didn't expect
that that would become another kid.
And then divorce and then
co-parenting, you know, as it went.
And that became like
its own midlife crisis.
And then through that process
of co-parenting and seeing the
challenges there, feeling so
challenged myself Also knowing
that deep down, I'm a technologist.
I love technology, I love building, and
knowing that I was a little rusty, you
know, from all those years of just being a
dad, I decided though that it was my duty
to wipe off the dust and get back in there
and solve this problem with software.
Yeah.
And you
did the.
I don't wanna say the classic
thing that founders do, but you did
the thing where you're like, I am
experiencing this problem myself.
I know that probably plenty of other
people are experiencing this problem.
I'm gonna build something that
helps people alleviate this problem.
Totally.
And you know, I would say I've
not ever had quite this experience
of feeling so mission-driven.
Like it's, to me, this feels
like I've found a vocation.
I really wanna help co-parents in
these situations cope and find peace.
It's like through my core, I've done
startups before and I felt really good
about what I built, but this is the
first time where I saw a need, I heard
what people needed, and then I built it.
And I feel so inspired
every day to wake up and.
Keep building for them.
Yeah.
And the mission here, like these are
like very real human problems that you're
solving, like, and you live through it.
And so it almost feels like
more meaningful as a result
maybe.
And Adam too.
I would say that for me it was a hidden
problem before I became a co-parent.
I had no idea.
In fact, honestly, I think a lot
of people who are married don't
want to even think about divorce.
Right?
They don't want to even talk to
divorce people or interact with
them because they don't want to
admit that could be a possibility.
Mm-hmm.
And so what I am trying to do with this
company is say, Hey, you know what?
Like this is a real problem
that people are facing.
This is a really difficult
relationship and there are not a
lot of good solutions out there.
And so, yeah, I'm jumping in and helping
bring light to what can be a really dark
and lonely situation for a lot of people.
So this.
This is a little bit of a funny
question here, but have you onboarded
your own family onto best interest,
or is that like a bridge too far?
I, I'm gonna keep that one a trade secret.
Uh, okay.
I can only imagine how
that conversation would go.
So we'll just move on.
What are some of the most surprising
things that you've discovered as a dad?
Oh,
wow.
What a good question.
You know, I think the first one
is just how challenging it is.
I think I.
Everyone on some level walks into
it thinking, oh, I'll be great.
I'll do it better.
And then you become a dad and you realize,
oh man, this is bringing up a lot of shit.
Oh, wow.
Like, so the things that I didn't
heal from my childhood at this
age are gonna start coming up.
It's almost a magical portal of healing
being a dad, especially when you're
really open towards and oriented
towards personal growth and healing.
It can be such a rich and challenging
experience to, to become a dad.
You know?
And I think, like I mentioned
earlier, one of the things I didn't
anticipate was the loneliness.
That it is being a parent, let
alone a co-parenting parent.
And I just, I really love advocating for
a shift in the way that we look at, I.
Parenting and co-parenting towards more
of a tribe and more of a community,
bringing more people together to help out.
I think kids benefit when grandparents
participate, friends participate,
other people, neighbors, right?
When they can look up to multiple
adults and they're not just relying on
one parent for all of their attention.
I think that that is really beneficial.
I
had
someone else on the show who said
one of the most isolating places
on the planet is being a dad on
the playground with your kids.
'cause you're often the only dad there.
Or you know, you're, especially if
it's during the work week, you know?
Oh my God.
So a, a anyways, that, that resonated
with me, what you just said about
the like kind of loneliness and
the, you know, the isolation.
I'll echo that.
Yeah.
I think especially early on when
my kids are really young and.
You know, going out to the playground
specifically, it was challenging as a
dad because there's this really weird
subtext in our culture about men and
children and relationships and like
questioning and doubting and that's so,
it's so problematic because the dads I
know are really good dads and they just
want help and they wanna be involved and
the kids benefit from their involvement.
And I've noticed that over the years
as a dad who shows up field trips,
you know, other places where other
kids are, they gravitate towards me
probably because their dad probably
is working or not as involved.
Right.
Like they feel that energy and
they're like, oh, you know, kids just
really, they wanna have a involved
dad, they wanna have an involved mom.
They wanna be part of that.
Yeah.
You
mentioned a minute or so ago
about, you know, having kids
brings up a whole bunch of.
Stuff about your relationship with
your own parents and things like that.
I, I can certainly appreciate that myself.
But I think one of the things you also
mentioned to me is that your kids helped
you heal relationships with your parents.
So tell me a little bit more about that.
Well, I mean, you talk about it
like past tense and I would say
that it's an ongoing process.
Um, you know, it, it brings up a lot and
I don't know what this life is all about.
Still trying to figure it out.
Probably will never figure it out.
But one of the orientations that I have
now that I didn't when I was younger, is
that I believe that life is about growth.
I think that, you know, we've come here
on a journey and we're learning things and
we're learning things about ourselves and
we're trying to get stronger and better,
and we're navigating relationships.
I know one of the themes in my life has
been how to unravel my own codependency
and stick up for myself more, to shine
my life rider to be more visible.
I was a very shy kid and
you know, very codependent.
I'm still unraveling codependency
and my kids have really helped me
because the one thing that having
kids does is it does force you
into connection with your parents.
Because they wanna be involved
and they're great with the kids.
They might have been really
challenging parents not saying
anything about mine, but they
might have been really challenging.
But they wanna be great grandparents
and usually for whatever
reason, that's how it works out.
They're great grandparents and so you
want them to be around, you need the help,
and so they create this kind of forced
bond where anything that's unresolved
in that relationship between you and
your parents is being brought to light
and you're having to work on that so
that it's not constantly triggering you.
It's wild how that works.
Yeah.
I've had some other
conversations with folks
where they're like, you know.
My own parents when I was a kid, you
know, they were okay, but like wow.
As grandparents, they're like off
the charts like what clicks, you
know, when they become grandparents.
So I don't wanna say that that's your
lived experience, but it sounds like
you got some great grandparents now.
So, oh, they
are the best.
They are so into that position and
it's such a sacred position, like being
able to jump in, relieve the parent
for a little bit, and just provide a
very different experience for the kids.
You know, just being super present as
a parent, you're filled with all these
other obligations and things in your mind
and things you gotta do and your work.
And especially as a startup dad,
man, there's a lot going on up there,
but they don't have that right.
So they're able to just be really
present and just get down on the
floor with them and just be with them.
And that's such a beautiful gift that
they can give to their grandkids.
Yeah.
So you have now an eight and a 6-year-old.
Yeah.
And I want to get in the time machine
for a second and go back to, you know,
before your oldest was born, right?
Before you had your first kid and you
bump into younger Saul in the time
machine, which I think is actually
not allowed based on the laws of
physics, but let's say you do.
What would you tell your
younger self about being a dad?
What advice would you give yourself?
Are you sure about this?
I mean, I would never take back
becoming a dad that I think that it's
important to not take it for granted
as something that everyone has to do,
or it's something that you gotta tick
the box and it changes your life.
Like becoming a dad.
It is a new chapter no matter what you do.
Like your focus changes for me.
It was pronounced because I
decided to become a full-time dad.
Right?
So like that, it's even different than
having a career and also being a dad.
But even when you're still
employed, like you suddenly realize,
oh, it's not about me anymore.
Like biologically or whatever.
You start being much more oriented
towards their life, what they're up to,
and realizing that if it really came
down to it, you would absolutely protect
them and allow your life to be taken so
that they could like, that just becomes
almost overnight and that shift is such a
big shift in the way you view the world.
And so would I say don't do it.
No, but just like it's a big deal.
It's an important decision.
And just make sure you,
you think it through.
Appreciate the gravity of the
situation for all of its, you know,
challenges and opportunities and
excitement, but appreciate it.
Totally.
Yeah.
What about in the transition
from one to two kids?
Like what have you learned as a dad?
What would you tell yourself about
maybe what you do differently with
your oldest kid than you know you did?
Yeah.
Well, there's definitely a few things.
I think going from one to two in
terms of like daddy responsibility,
it's not two x, it's like 20
x, like it's, it's ridiculous.
It just becomes so much harder, but.
Also, one of the things that
it taught me was that you just
don't sweat the small stuff.
I look now at products that are
sold to first time parents and I'm
like, oh, that's, hmm, that's awful.
Like you see those baby cameras
that are attached to the bassinet
and it's like $2,000 and you're
gonna use it for three months.
And yet it's being sold like hotcakes
because they're selling to the fear.
And when you're a first time parent,
especially when you hold your child for
the first time and you look in their eyes,
you're like, oh my, this is important
and you're ready to buy anything.
And also, I remember just
being terrified at every noise.
It was crazy.
Like she, her just her
breathing, I thought, there
must be something wrong there.
There must be I, we
have to call the doctor.
You know, like I was so hyper-focused.
Common experience.
By the time my son was born, like
I had been through the ringer, I'd
known that everything is totally okay.
Kids are very resilient.
They're built like a tank.
It's fine.
They're gonna survive
through pretty much anything.
Yeah.
And so for him, like obviously
that was a lot easier.
I. And I didn't buy all that
crap that you don't need.
Yeah.
You said two things
there that I really appreciate.
One is the loud breathing is a sign of
imminent death, and I just remember when
my dau, my, my oldest is also a girl.
Just like the noises that babies
make when they're sleeping.
They're like grunting and
like, and they're totally fine.
It's just very normal,
but they're not quiet.
They're like, you know, they're like, no,
what I would imagine like an 80-year-old
man is making the noises of in his sleep.
So that's one.
And then the idea that, you know, the
kids are gonna be okay, I always tell
people like, ah, kids are pretty much
made of rubber, you know, they'll be fine.
Totally fine.
Yeah.
And second kids get a different
treatment because of that.
You know, there's, I think a lot
more flexibility that they're given.
There's maybe even less expectations.
You're kind of, in some ways, overall
that stuff, and it's good and it's bad.
It's just a different experience.
Yeah.
So you talked about, you know.
Life being about growth,
personal growth and learning.
And I'm curious if you've developed any
frameworks or guardrails for parenting
or like how you've grown in thinking
through what it means to be a dad.
Yeah.
A lot of parents, when they approach
parenting, they do the Gogos and Gagas
and they like kind of, I've always wanted
to treat my kids with the same level of
respect as if they were adults, right?
I think that we talk down to our kids
sometimes thinking that maybe they
don't understand or they're not ready.
And I'm not necessarily saying like use
big words and be eloquent, but I just
really wanna respect them and respect
their personhood in the same way that I
would with an adult, if that makes sense.
And.
In addition to that, I tend to like
allowing them to do it on their own when I
can and to even give them responsibilities
that are way above their pay grade,
because I think that's really fun.
I'm not afraid of giving my kids a
hammer or a power drill, you know?
I figure if there's really a problem
then you know, we can take care
of it and I watch them closely.
But I think I just love seeing the
eyes of my daughter light up when
she knows that she can hold the drill
that daddy uses to build something.
I think that it just gives her like
this added weight and responsibility
and like feeling of freedom.
My kids are amazed by power tools.
That's really.
That's
really a thing I've learned.
Yeah.
I mean, I haven't always been a builder.
Actually, that was something that
evolved after my daughter was born.
I was always a coder and sat
behind my computer and I had
this experience actually one day
of wanting to get a garden bed.
We were living in San Francisco at the
time, so the idea of having a garden
was like this exotic, crazy idea.
And so I went down to Home Depot and
I said, do you have any garden beds?
And I said, oh, you know, like it
looks like they're sold out, right?
So he said, oh, well it's just wood.
And I'm like, what do you.
Oh, oh, it's just wood.
Like I could build it myself.
There was, there was something
that clicked that I didn't
realize I didn't have to buy it.
Of my kit.
Yeah.
I could just build it.
And so I have since then, built
a lot of really great things.
I love working with my hands.
I've developed quite a tool collection
and I love passing that down to my
kids, knowing that they can build it
themselves, they can repair it themselves.
We love repairing things
instead of buying new things.
That's a big thing around here.
I like teaching them that stuff.
Yeah.
And also very empowering
for them to feel like.
I can do this.
You know, it's just wood,
you know?
It's just wood.
Yeah.
That's build it ourselves.
Doesn't power ourselves.
I think in this culture we have this
outsourcing mentality where everything
is assigned to a professional to do.
Mm-hmm.
You can't really do a lot yourself
these days because it's a professional's
job to do it, and I think that's
actually a really big disservice as
we're facing a very uncertain future.
I want my kids to know
how to build things.
I want them to be helpful members of
their community and I want them to
be able to operate independently, run
their own house and, you know, fix
things around the house without needing
to employ someone for everything.
Yeah.
Speaking
of building, you have built a lot
of technology products in your life.
Your entire career has been
building things like starting
companies and building products.
You know, your kids are getting to the
age where, and society is getting to
the place where like technology is.
Deeply ingrained in our lives.
And I'm curious what you want your
kids' relationship with technology
to be as they're getting older.
You know, we're, we're watching
the airplane being built while
we're flying in it, right?
And I think this AI change is so
much bigger than we really can fully
grasp 'cause we're in the soup.
And so I definitely have my
mind on that when I am seeing
what they're learning in school.
Obviously the public school system's
not adapting very quickly to this.
Education in general is not
adapting very quickly to this.
And I'm really uncertain what the
future's gonna look like for them.
You know, when they are old enough
to get a job, will there be jobs?
Right?
What will the jobs look like?
How are we going to define
what productive work is?
Is it going to be just being really
good at managing a bunch of AI agents?
Maybe I think that there's a
lot of, let's wait and see and
let's just find out what happens.
My daughter is an amazing
artist, and we did this great
thing with the new chat, GPT.
I don't even know if
there's a brand on it.
Oh, the new image, the new cartoon tool.
Yeah.
Image Generat.
Image Generator,
yeah.
Oh
my gosh.
Such an amazing tool.
I was a mid journey guy for a long
time, and this is just miles beyond.
So what we did is she's super creative.
She's just started drawing these
amazing animal cups, I think
could be an A to a product.
Absolutely.
And she draws them and she's like,
we'll get requests on Facebook.
And she draws on requests
and it's really fun.
I thought, what if we popped this
image that she drew into Chachi
PT and asked, make it real.
Right.
And sure enough, it made this amazing.
I. Plastic in, you know, in a real cafe.
And it just, it was so, I could tell it
was so inspiring to her to be able to
see the reality of what she's making.
And I can see that as being something that
will be very helpful in the future as the
humans being the spark of the inspiration
that leads to the product, right?
That it's all about ideation,
individual creation.
And so for me, when I am thinking about
that future, I really hope and would love
to inspire my kids to be entrepreneurs
themselves and to be thinking about
what they wanna put into the world,
the reasons why, how to come up with
a good idea, how to be a self-starter.
And also, honestly, I think being
an artist is really important.
And I think that is perhaps going to be
the way that we are communicating with.
These machines and understanding them
is through art, through storytelling.
And we'll see.
We'll see where it goes.
Yeah.
You're echoing is something that
I've heard from, you know, a growing
number of dads on this show, which
is using technology as an active
participant and as a tool for that
growth that you describe, right?
Yeah.
And so how amazing at some point for
your daughter to be able to go from
like I drew a picture to maybe this
thing can be produced physically.
Now, this picture that I
made, what a cool concept
AI is going to make it so that
you can have an idea and you
can make a real version of it,
literally in an hour or less, right?
And it's gonna come up with a
marketing plan and it's gonna know
where to distribute and it's gonna
make the connections and your AI
agents, it's going to be such an
incredibly explosive time of creation.
And so then my question is.
What is that world gonna
be like to live in?
Right.
That's where my fear is, is just
being overwhelmed by all the
great products and ideas and apps.
It's like, how are we gonna be
able to consume all of that?
Yeah.
If I succeed in this parenting
thing and launching them, I really
hope to launch them into being a
little entrepreneurs themselves.
Hmm.
That's awesome.
On the flip side, what would you say
is a mistake that you made as a dad?
I've made several, so I think the biggest
one that I have the most regret about,
honestly, you know, it's interesting
to admit this in a public setting,
but I like to live my life openly.
I think.
It's this memory I have of when my son
was three, he was like deeply into that
three-year-old energy of feeling the
frustration of the world, not conforming
to your wishes, and then not being
sure what to do with that energy and
channeling it into aggression and anger.
And as his father, it was
pretty frightening and
overwhelming to experience that.
And he would start punching on his
sister and punching on me and like being
able to produce a fair amount of pain.
And so that I knew wasn't gonna
stand and I didn't know what to do.
And so I remember.
In one of my iterations of trying,
I tried to holding him so that he
couldn't like, but then that felt like
weird, like I was restraining him and
it didn't seem to help him at all.
He just got worse.
And then one day I thought,
well, I'll put him in his room.
Well, we're in a house
with two doors on his room.
So that didn't really work very well.
He just ran outta the other
door, so, whoops, dad.
And so I thought, okay, well maybe if
I just, 'cause I had this notion maybe
from when I was a kid, I don't know, go
to your room when you're upset, right?
And so I thought, well maybe I'll
just put him in this closet and you
know, maybe that'll calm him down.
Well, it calmed him down immediately
and I opened the closet and the look on
his face was just like, it was so sad.
Like, I feel sad even relating that.
They're thinking about that image.
He was so sad.
And so in that moment I thought,
oh, I'm never doing that again.
That's not something
that I'm ever gonna try.
And what I have learned since is
that it's really about, I don't
wanna ever push my kids away or
even create separation, right?
Because kids are, they're governed
by wanting association with you.
That's how they feel.
Safety.
So if you're pushing them away and
saying, you're now disconnected
from the tribe, go, you know, that's
the worst feeling in the world.
That's like, as an adult,
that's torture for a kid.
So I try to never do that.
But what I do is I help show
him ways to use and manipulate
that energy in productive ways.
And so I try to redirect it.
And so what we started doing was I would.
Take him to a different room with
me, I'm there with him, and then
showing him and doing it myself too.
But like punching, punching a
pillow, something safe, right?
Allowing him to push against
me while I hold him, right.
And just being okay with that
energy being directed at me.
And that really helped, honestly.
And I think that, I would imagine
that is helping him learn how to be in
relationship with that energy, those
emotions that are so strong, that
honestly will be part of his whole life.
And so I want him to have a
good relationship with his
anger, with his sadness.
So yeah, that was, yeah.
Wow.
A mistake in learning.
Yeah.
And I mean, thank you
for sharing that story.
I would imagine it's more common
than we might think to have
something like that happen.
And it sounds like you've
learned a good lesson about not.
Trying to quiet the energy,
but just redirecting it into a
different, more productive place or
allowing it to be there, but away
from harm or anything like that.
Yeah.
I love what, uh, it's allowing the
energy to be present, but directing
it into a place that's more productive
and safer for everyone, including
it, rather than excluding it.
Yeah.
Well, that sounds like a great thing
to end on, a great lesson to end on,
so I appreciate you sharing that.
How can people follow along or be
helpful to you on your journey?
For any of your listeners that are
co-parents themselves, you can look me up.
I run a podcast called Co-Parenting
Beyond Conflict, where we specifically
talk about how to cope with and thrive
in this sometimes very challenging
situation of being a co-parent.
So you can look us up on Apple Podcasts
wherever you get your podcasts,
and also if you're interested in
co-parenting with best interest.
Best interest allows you to create peace
and can be a very difficult situation.
Using AI as a tool to moderate all
communication between co-parents,
you can experience peace.
So you can look us up on
best interest app.com.
Okay.
Well thank you for those.
We'll link to both of those
places in the show notes.
So appreciate you sharing that.
Are you ready for our lightning round?
Sure.
No one is ever officially
ready for lightning round.
I
thought I was off.
Shoot.
Okay.
Okay, here we go.
What is the most indispensable
parenting product that you have
ever purchased?
This one's great.
So it's a little bug catcher that has
a little sliding trap door and whenever
you find a bug in the house, you can
go and just take it safely outside.
And I think that that is such a great
image or a great experience for the kids.
Not only do they get to look
at the bug, 'cause it has a
nice magnifying glass in it.
They can learn about bugs, but
it also teaches them that it's
better not to kill things.
We love it every time we see a bug.
Get the bug catcher, dad.
There's no panic.
It's just like, go do this thing.
Yeah.
That'ss.
Awesome.
What is the most useless
parenting product that you've
ever purchased?
Earlier in the interview I was
talking about these products that
are sold to first time parents.
Honestly, I think it's pretty awful.
As a first time parent, I would
highly encourage you, get only
used things, don't buy new stuff.
Definitely don't buy technology.
Your baby's not gonna die.
I mean, SIDS is a real thing, absolutely.
But not at the level
that you're afraid of it.
Right now, don't buy that fancy
$200 sock that I'll monitor.
It's just gonna go on the waistband.
You know?
It's like not, not helpful.
So just keep it simple
and get all your stuff.
Hand me down.
This
is the second time, probably in
a week or two, that somebody has
said that the, that baby sock,
that monitors is a terrible idea.
The last person said it's because
the baby sock makes you think
that your kid is always dying.
I never used the baby sock, but I
definitely thought about buying it and
yeah, I now know in hindsight, no, it's
not a good use of your time or money.
All right.
What is your signature Dad's superpower?
Yeah, I mentioned it earlier.
I think it's my, my calm, my grounding.
I tend to be able to navigate all
situations with my kids with like
calmness and I really like to
help them redirect that energy.
Now in your household, are you
team swings or team slides?
I really, I love doing things together
with my kids and I think I like slides and
I think my kids really like slides too.
We don't have a slide.
We have a swing.
Swings are cool because
you can do it together.
I love pushing my kids on a swing.
It's like the best thing.
I'll be so sad when they sob
ask me to push him on a swing.
Yeah.
Yeah.
If your kids had to describe you
in a single word, what would it be?
Is it the first word
that comes to my head?
I don't know.
Maybe nice daddy.
I actually don't know.
Yeah, that, that checks out.
That's probably good.
What is your go-to dad wardrobe?
I am all about efficiency,
as you can tell.
I love hoodies.
I love warmth, and honestly, I've
never been fashionable, but I was a
little bit more fashionable than now.
Now I'm just like, ah, whatever.
Yeah, just put it on.
I don't even care about my hair
when I drop off the kids at school.
Like who am I trying to impress?
No, it's
all about convenience.
Yeah.
Yes.
What is your go-to bribe for good behavior
with
the kids?
Well, we do this thing here
that is actually really cool.
It's worked pretty well, so we have a
token system, and I have somehow trained
them that tokens are the reward and
that they can use the tokens for things
that they want, and so we have this.
System that's set up where, you know,
if they do something good, like clean
their room, then they get a token.
And then if they wanna do something like
watch on the tv, it costs a couple tokens.
And so it's like an early introduction
to chores and we're starting to adapt the
token system to be convertible to money.
So there's kind of a mapping
to money and they were able
to buy something with tokens.
And so there's kind of that going on.
But I really like disintermediating
reward with like work.
I never liked the idea of like,
okay, if you do this thing,
I'm gonna give you this candy.
Like that's just not, and
oftentimes the reward doesn't.
Always follow.
So I like this idea that they have a
duty to clean their room, and that's not
always gonna map to them watching right
after, but they know that when they're
building up those tokens and later
they're gonna be able to get the reward.
Yeah.
Maybe when they're older,
you could build a little
app for them that they could
keep track of their token.
Don't,
no, don't get me started.
I'm already busy.
Another company.
Another company.
Okay.
Speaking of rewards and purchasing
things, what is the most absurd
thing that one of your kids has
ever asked you to buy for them?
Well, okay, it's not exactly absurd,
or at least it didn't start that way.
My son got a stuffed piggy.
I don't know if it was like a
gift or I don't really know how
it came into our lives, but he
loved that stuffed piggy so much.
And this would've been probably
almost two years ago now.
Loved it so much that the
piggy started going back and
forth between the two homes.
My kids aren't like big into
bringing things back and forth.
Well, somehow that's actually pretty good.
It's pretty easy.
But this pig would go back and
forth in his backpack and it
was like on the order of being a
little too big for his backpack.
So, but then I think I may have made
the mistake of buying him another piggy.
And then that piggy became
three and suddenly three piggies
were going back and forth.
And that was when daddy put his foot
down, said, no, you can't do that.
That's too many piggies for school.
So I made the ingenious decision to
tell him, okay, I'll buy you three new
piggies and then you can have, keep those
three piggies at the ones you have at
your mom's house and keep three piggies
at my house and we're good, right?
We're good.
You don't have to take 'em back and forth.
And he's like, yeah, good.
And I thought that was it.
I. So now we have 36 pigs.
He's proud to tell you, 36
pigs and it didn't work.
They go back and forth.
They're, we have pigs everywhere.
I don't know what's going on,
but that was not a good solution.
You need a separate vehicle
just to transport the pigs.
It's like moving a football
team back and forth.
We have moved pigs in boxes before.
Yes.
This is my, this is the equivalent
of my son with penguins.
Same thing.
He doesn't have to move him back
and forth, but he does like to
bring a penguin or two on a trip.
So, yeah, you know, I
don't know what it is.
I think it might have
something to do with like.
He feels known by his
association with Piggie.
Obviously he likes 'em, but this is
like the piggy king of his school.
Like all the other kids know that he
loves pigs and they barter pigs with
him, like they give them their stuff,
pigs that they don't want, like this
guy's got, he's got piggy games swimming
and swimming in pigs.
He's got real riz when it comes to pigs.
So yes, as the kids say, what
is your favorite kids movie?
You know, there's a lot of crap out there.
I think what I like the best is
sitting down with them with Pixar.
I think Pixar is pretty much
always good and I love how it's
entertaining for me and for them,
and it just works for everything.
Yeah, that's my go-to.
Okay.
All things Pixar.
What
is the worst experience
that you've ever had?
Assembling a kid's toy
or a piece of furniture?
My kids are very lucky because
they have a dad who is quite handy.
My grandfather actually growing
up, I remember he was so handy and
was able to do anything and build
anything for me when I was little and
I would always looked up for that.
And so I, I love being able to be
that for my kids, but also teaching
them how to build stuff too.
And like incorporating that in.
I'm not gonna do it all for them,
but I'm gonna teach them how to
do it so they can do it with me.
And so, yeah, I wouldn't say that I've
ever had any struggles with building
anything and I love building things with
them and making my own stuff and yeah.
Awesome.
And an amazing rarity in a
dad I find these days, so.
Really?
Oh, that's surprising.
It's so fun how?
It's just wood.
It's just wood.
I love that.
That's gonna be the title of this episode.
How long can a piece of food sit on
the floor and you will still eat it?
Oh, I don't know.
I mean, uh hmm.
I am pretty sensitive to my digestion
and I'm actually fairly critical
of not eating things that, you
know, when in doubt, throw it out.
That's
okay.
All right.
I think it's a good rule to live by.
Yeah.
Okay, two more for you.
What nostalgic movie can
you just not wait to force
your kids to watch with you?
Star Wars.
We're still waiting on that one.
Yeah, I think maybe about a year ago,
like I, I opened it up a little bit
too early and like there was some
fear that I sensed, so we stopped it.
But God, I can't wait.
Can't wait to show them Star Wars.
Yeah.
Hmm.
Now will you go, so
there's nine of them now.
Will you start at the very beginning
or will you go like the original
order that they were released?
What do you think?
I think original order.
You got to.
I think so.
I don't even, I think I'll just pretend
like the other ones don't exist and
let them discover them on their own.
One, two, and three.
Not worth it.
I'll let them disappoint themselves.
Yeah.
Yeah.
Okay.
Finally, only have two kids,
but you do have a lot of pigs.
So what is your take on minivans?
Well, you know, I'll tell
you, it's a complicated take.
I think that there is a choice you get
to make as a parent when choosing cars.
You can either be the parent that drives.
Every single kid around,
everywhere all the time.
If you wanna do that, get the mini band.
If you wanna have a little bit more
peace and less responsibility and
have your kids be driven around,
then get the normal five seater.
Yeah, that's what I chose.
Mini Cooper.
Yeah, right.
Motorcycle.
All right.
Sidecar.
Right.
I love that sidecar.
Just for the pigs actually,
so, yes, that's right.
Okay.
Well, Saul, it has been my absolute
pleasure having you on Startup Dad today.
Thank you so much for joining
me and best of luck to you, your
family, and your burgeoning app.
Best interest.
I'll have to go check it out.
Thank you, Adam.
I really appreciate it.
Thank you for listening to today's
conversation with Saul Kennedy.
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I.