July 28, 2025 • 27 mins
🎧 Episode 20: Daring Greatly
In this penultimate episode of our Wholehearted Parenting Manifesto series, we reflect on one of the most courageous lines in Brené Brown’s manifesto:
“The greatest gift that I can give you is to live and love with my whole heart and to dare greatly.”What does it mean to dare greatly as a parent? For Danielle, it’s reclaiming personal ambition and giving herself permission to live a full life outside of motherhood—without apology. For Greg, it’s stepping into deeper emotional vulnerability, particularly around his role as a dad.
We talk about:
- Why daring greatly looks different for everyone
- Climbing our own mountains while still being present with our kids
- Releasing guilt, comparison, and the myth of doing it all
- Letting our children witness us pursuing meaningful goals
- How family can be a base camp, not the entire expedition
- Our personal experiments in emotional honesty, outsourcing, and intentional presence
Whether you’re building a business, raising a family, or figuring out what lights you up outside of both, this episode is a heartfelt permission slip to live with more courage, truth, and fullness.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Welcome to The Most Important Thing.
I'm Danielle DeMarco Neufeld. And I'm Greg Neufeld.
Together, we're exploring how ambitious busy families can
build culture at home. Because after all, family is the
most important thing. Hey teammate friends.
Hi everyone, welcome to episode 20. 20 That's right, XXXX.
(00:21):
And the 10th in our wholeheartedParenting Manifesto series.
The penultimate episode, if you will.
For those of you joining us, forthe first time, we've been
taking Brene Brown's Wholehearted Parenting
Manifesto, breaking it down lineby line, and re parenting
ourselves with each line. That's right, it was like a
(00:42):
Trojan horse. It really was.
Yeah, it was a Trojan horse. I thought we were going to be
exploring other people's things.We explored lots of my things
and your things, but lots of people have reached out saying
that they explored their things too.
That's right, things worth exploring.
It's pretty cool and we've been doing some experimentation this
summer. We've had a couple of interview
(01:04):
episodes with some of our friends.
We call them teammate, teammates.
So hope that you've been joiningfor those.
And if you know a teammate, teammate, or if you are a
teammate teammate, we'd love to have you on.
That's right, it takes a village.
It does so. The Wholehearted Parenting
Manifesto is Brene Brown's ode to new children, in a way.
I think it the way she has described it, if I may use her
(01:27):
words instead of yours, sure is that she wrote it and didn't
know if she would ever publish it, but that it's her own
compass towards parenting. Yeah.
And so Brene, this is our ode toyou.
And we are now one more from today away from finishing.
Yes. So the second to last line in
the manifesto, the one that we will be talking about today, is
(01:49):
about Daring Greatly, which she later wrote a book on.
That's right. Yeah, as you begin your
wholehearted journey, the greatest gift that I can give
you is to live and love with my whole heart and to dare greatly.
Shall we talk about in her definition what it means to dare
greatly? And then maybe we can talk about
(02:11):
how we are each daring greatly right now.
Let's do it. OK, cool.
So Brene defines daring greatly as the courage to be vulnerable,
to show up and be seen when you have no control over the
outcome. It comes from Theodore
Roosevelt's famous speech Man inthe Arena.
So she uses this to under score the idea that daring is not
(02:34):
about winning and losing. It's about having the courage to
step into the arena of life, knowing that you might fail, but
choosing to engage with your whole heart anyway.
Is it a weird time to bring up Chamath?
Never. Chamath Poly Hypatia, yes.
Chairman, dictator. I always think of the man in the
arena with Chamath when he was doing all of his Spacs and
(02:58):
everyone was losing money and he's losing money and like he
was just going horribly wrong. And he was like, I'm just in the
arena trying stuff. That's his rhetoric.
So niche, Greg, tell us everybody would love to know the
crossover between team at listeners and all in listeners.
Definitely one there. One me.
I mean, I'm sure there's more. There's probably a few.
There's probably a few. I think we've got a couple that
(03:18):
are that are working in the DC industry that are parenting and
running investment firms and or maybe running venture backed
start-ups. I'd say the crossover is
actually pretty big, and after this episode maybe even bigger.
Yeah, come off, come listen. Sure, anyway.
Where are we going here? OK.
So where are we going here? This.
(03:39):
The greatest gift that I can give to you is to live in love
with my whole heart and to dare greatly.
I This line is a breath of freshair for me.
And it might just be the way I'minterpreting it, but let's go
with it. Yeah.
Because what comes up for me when I hear this is that life is
about climbing our own mountains.
And this idea that we've talked about before as family, as a
(04:01):
base camp. And there's a specific quote
that comes to mind from Carl Jung where he says nothing has a
stronger influence on their children than the unlived life
of a parent. And I love this because I feel
like it gives me license to go and live my life as a potential
(04:24):
way of avoiding putting my children in the therapy chair.
As opposed to so much of what I feel today, which is this mom
guilt, if you will, around. If I want to live my own life,
it will somehow detract from my children's life.
Does that make sense? Of course it does.
(04:46):
So I feel as though I, I guess Itake Renee's words in the
broadest sense, the courage to be vulnerable and the courage to
try new things and the courage to be myself, which is so much
more than just a mom. I love being a mom.
(05:07):
It has been the most transformational experience of
my life, but it is not my whole life.
If I'm being really honest, it'snot even the foundation of my
life. And it feels a little verboden
to say that, but it's the truth.And when I think about daring
greatly, particularly where we are with our family out of the
(05:29):
blocking and tackling years, as I like to call them, and more of
the family as a democracy years,I feel like I'm I'm declaring my
independence, if you will. And I've been thinking a lot
lately about what that looks like.
And it's hard. It is hard in the world of
(05:50):
gentle parenting. It is hard in the world of
social media with trad wives andmoms on Instagram telling me to
lean into the chaos of three different travelling sports
teams on the weekends. And I'm kind of like, I'm trying
not to curse right now. You're allowed.
I'm kind of like, fuck you, that's not what I want to do.
(06:14):
I love my children with my wholeheart and I have no intention of
following them around for the next 15 years.
Let me just tell you emphatically, I will not follow
them around for the next 15 years.
And this is what I really feel in my heart, and I hope that I'm
not alone and I hope to make space for those that are with me
(06:39):
to say that that's OK. There it is.
I guess it is my hope that by living a full life and daring
greatly, I also authorize our children to dare greatly in
their lives as well. Amen.
That said, it does mean that I am going to be outsourcing a lot
(07:02):
of the day-to-day of parenting life.
I'm not going to be the one taking them to ballet or soccer
practice, because while they're exploring their own interests, I
am exploring mine. And it also means that on the
one hand, while I do believe that deeply fulfilling my own
personal life will bring me morecapacity for presence and joy
(07:23):
and meaning when I spend time with them, it also means that
sometimes Maverick is screaming his head off 10 minutes before I
have a very big important clientcall.
And not only do I lead from my not best self, but I go berserk.
I go absolutely nuts because of the stress of it all.
But I guess that's human, you know, it is human.
And 'cause sometimes I think, wow, if I didn't have my hand
(07:46):
and so many different things, maybe I wouldn't freak out at
Maverick for screaming. But it's OK that I want them to
know that Mommy is a whole person with a lot of really
important pursuits that are close to my heart.
The most important thing people typically have been ending their
sentence on podcasts when talking about family with those
(08:08):
words. Family is the most important
thing. And then not going into why.
We set out to explore what thereis beneath those words in this
podcast, and it's interesting because it takes us through this
journey of what it means to be ameaningful participant and
climbing your own mountain at the same time.
(08:31):
And I think the best entrepreneurs can get too
focused on climbing that mountain without letting their
family see them along the way. Because having our kids bear
witness to us climbing those mountains and understanding what
it means, not just closing the door on them, is the difference
between a great entrepreneur anda great entrepreneur that's also
(08:53):
a great parent and role model. Is it crazy that I really want
to be both? No, in fact, Jack Altman,
yesterday Tiffany Zong sent me this tweet, as you know, from
Jack Altman, which I thought wasa little bit simplistic.
But now that I reflect on it, the people I look up to most are
(09:15):
equally amazing at work and withtheir family slash kids.
I don't think that's too much toask for, but I don't think that
it means that you take them to all of their soccer games and
run a business. And that is the trap.
I think a lot of people are trying to fall into or are are
unintentionally falling into, which is trying to have it all
(09:37):
by doing it all. And I think what you're naming
is what a lot of people are feeling, which is I can't, I
have to put on my oxygen mask first.
I have to climb my own mountain and let my kids bear witness.
My children are not my legacy. They are fill in the blank.
(09:58):
My my witness. My witness, Yeah.
I guess it's just, you know, different philosophies.
I don't want to be judgmental towards any other philosophy,
right? But I can tell you that when I
was watching Real Housewives of Miami over the weekend, I guess
it was. And Larsa Pippen said I am
investing in my kids so the fruits of their labor better
(10:18):
come back and take care of me someday.
I was like, heck no. Like that is just not me.
That and I understand that that is a mindset and I hope that it
works out for her. But if anything, I am the
complete opposite. I am the one that is wanting to
live in the here and now. Like, I don't know how much
longer I'm going to live, honestly.
(10:39):
Maybe it's a mortality thing, who knows.
But like, I'm not willing to putoff my dreams until they've left
the nest. Of course not.
And I guess I I'm hoping that there are benefits to climbing
my mountain as our children are growing.
And what that really has meant is that I do need to outsource a
lot of the more time intensive, more rote tasks like carpooling
(11:03):
and doing the laundry and cooking dinner.
But I still try to be involved in holding space for their
feelings and spending intentional time with them.
You know, the first two hours every morning in the last two
hours before bed at night. But it's more of a side by side
activity these days, especially as they grow.
(11:25):
It's you're doing your morning chores.
Well, I'm doing my morning chores and we're talking and
we're interacting as humans about our day as opposed to I'm
waking you up and I'm helping you get dressed and I'm cooking
you breakfast and I'm washing your clothes.
Those are not in our first arc of episodes.
(11:46):
If you think about The Most Important Thing, episodes one
through 8, none of them are taking them to school or picking
them up from school or doing their laundry or putting their
clothes away. None of those things.
And I want to say that on the one hand, these are first world
problems because we can afford to have a nanny to do that and
that is not the case for everyone.
On the other hand, I want to acknowledge that that is a
(12:08):
financial sacrifice. Like there is a world in which I
do not climb my own mountains right now and we don't hire a
nanny that makes umpteen dollarsan hour and we have a different
financial picture. By the way, I would love to be
paying umpteen dollars. An hour.
If there's a way to pay umpteen.Anyway, you understand what I'm
trying to say there. There is a different world where
(12:30):
of course I put my mountain climbing aside and do all of the
things for the children and thenhaving a nanny is not the
largest expense that we have. I saw one of your girls videos
on Instagram, this mother of four boys that you have been
following and she says, you know, taking care of four boys
is this many hours. At this rate, it's $180,000 a
(12:52):
year or something like that. I'm on the clock from this hour
to this hour and the family knows that.
I thought that was pretty cute because it is putting a price on
not having extra help. It is putting a price on what
that means for the family, and hopefully the family can the
benefits of those extra dollars saved.
But in this family, we're spending the money to climb our
own mountain, so we better, well, climb them.
We'd be doing ourselves an injustice if we weren't.
(13:13):
Right. But I want to make clear though
that for us this is, this is nota financial gain goal, no.
Right. No, This is a fulfillment.
This is a personal fulfillment. Who do you want to be?
Goal. Yes, because nannies don't come
cheap. Especially good ones.
This is a push myself to the things that I know I'm capable
of without the constraint of thethings that I know will create
(13:36):
tension and make me feel resentment.
Sure. I just want to say that I have
friends who are amazing stay at home moms and a lot of them had
moms who were amazing stay at home moms and I would just like
to honor that while saying and Ideeply respect that as well.
So I honor and deeply respect that.
That is not me. Like I would go insane.
(13:59):
I would be resentful. So it's just not a skill set
that I possess. And I'm really grateful that you
have seen that in me, accepted that in me and kind of pushed me
out the door at times to say no.We there is no space for you to
do that here. Correct.
Yeah. Well, when in fairness, when we
(14:19):
met, you weren't like, oh, I can't wait to get out of this
9:00 to 5:00 so I can have babies and like that, that was
never going to be you. So I just, I'm trying to honor
the person that I met and remember.
Three weeks before we started trying to have a baby, I was
like, EW, babies are gross. Yeah, yeah, I do.
Hormones are real. They are.
(14:40):
So Darren greatly means to each of us something different.
To you, this clearly means climbing your own mountain right
now. Yeah.
Can I just also say that I thinkit has a bit to do with family
of origin as well, so. What doesn't?
I know, right? But like my mom definitely did
(15:00):
not live for me in a really goodway.
Like in a really good way. She had her own life.
And I guess so, I guess you know, to kind of liken it to
what I said about I have friendswho really appreciated that
their mom was a stay at home momand took care of them in that
way. I really appreciate that mine
didn't and that is one thing that I would like to continue.
(15:23):
Yeah, yeah, there's a lot of story wrapped up in everyone's
own next for them once they havekids, right?
Like the family of origin component, what they were doing
before, you know what they always aspired to do.
I think the the most important thing about climbing your own
mountain is that you're not afraid to just try things.
(15:43):
Yes, and that is the license that I feel that I have in this
family and I hope you feel as well.
Yeah, that is probably it's the lynchpin.
It's the most important thing. So thanks for letting me talk
about Aaron greatly. It's something that.
I not just talking about it, you're doing it.
Thank you. I feel a little, I feel a little
nervous talking about. This.
(16:04):
Honestly, like I said, it feels verboten.
It it feels like something I shouldn't be talking about.
I think you're going to finds that there's a lot of people
here for it and that are doing it.
I think there are a few. I've definitely met a few that
come to mind. I just want to make in the same
way that I, I guess this is thisis the episode where in the same
way that we started this podcastbecause we want family culture
(16:26):
to be spoken about more. This is where I am saying that I
want moms who are daring greatlybecause they really are
passionate about it. I want to hear from them more
too. OK.
And what about you, Sir? What about me?
Yes, what about me? What about you?
Chilling. No, you're many things chilling
(16:47):
is. That What About Me, Daring
Greatly for me has been following the arc of this
podcast. Not necessarily in the creation
or the production, though those are new challenges too, but I
would say in the experimentationand most of all the
introspection. So we started really nice and
(17:11):
soft and gentle with some thingsthat as a family we can do to
get behind. It's so funny you call that arc
soft and gentle, because it's not.
It's actually crisp, clear linesof routines and rituals.
Like actionable things, right? But it felt safer.
Way safer for me. I mean, starting family meetings
it like, you know, it was basically business family.
I'm like, oh, OK, I can do business family.
Dad, that's a guy that I can call up.
(17:34):
He's he's very available. It's been a lovely way to
connect more with our children with you and to build habits and
routines that I think are compounding family meetings,
especially, you know, cannot sayenough good things about family
meetings. I think the problem solving that
our kids are showing up with allows us to be witnesses and
(17:55):
not necessarily like just solving problems for them all
the time, which has been really great.
Now getting into the whole heartof Parenting manifesto topics, I
didn't realize how much work I still had to do in naming a lot
of my unspoken behaviors or habits or patterns or things
(18:17):
that I have just been on my internal narrative that I've
never said out loud. And to share those with you,
that's just called marriage. But to share them with you in a
format where I don't know whose ears they land on and that I'm
OK with that. That for me has been, it's not
just interesting or a little uncomfortable, but it's actually
(18:38):
been really exciting. I think the most exciting part
of that is knowing that I have this path in front of me to do
it more often. And so I think a lot of the
early work that I did was just seeing what showed up and
getting on the mic and talking about it.
I think the work to do is going to be digging a little bit
deeper because I owe it to myself.
(18:59):
You know, I owe it to you. I owe it to the listeners, but I
owe it to myself. I, I owe it to the dads like me
that are climbing in the charts.I think it's like 40% of the
audience actually are dads, which which is, which is pretty
sweet. I owe it to the dads to show
that vulnerability is a masculine trait, to show that
(19:21):
being vulnerable as a dad doesn't mean that I lose my
perspective on what still matters.
Doesn't mean you're going to fall apart.
Doesn't mean I'm going to fall apart.
Doesn't mean you're not still going to be our rock.
Exactly. Yeah.
Can I just say, if I may, this is so this idea of daring
greatly, really showing up vulnerably with courage and
(19:45):
being in the arena is something that I feel that I have done in
my personal and emotional life for a long time now.
And I think it is something thatyou have done in your
professional life for a long time now.
You have been an entrepreneur for how long?
Oh God. Since you were how old?
Since I was 1312, yeah. Yeah.
(20:06):
And showing up vulnerably, courageously, starting your own
business, starting your own venture capital firm with very
little experience, to put it mildly to.
Put it mildly. Right, with two partners who
really wanted to start it with you.
Yeah, right. That is daring greatly, truly,
(20:30):
and you've been doing it every day for more than a decade now.
And so you have really shown up professionally in a courageous
and vulnerable way. And now while I am transitioning
to professionally daring greatly, you are transitioning
to personally and emotionally daring greatly.
So we're kind of like crossing paths, if you will.
(20:51):
Yeah, no, thanks for framing it that way.
For context, I, I started Value Stream in my 20s.
Before that, I worked a little bit in software and started a
couple of fledgling app companies, worked in sales a
little bit. Never really had a large
organization. That gave me probably some of
(21:13):
the lessons that I would have learned a little bit faster had
I worked in a large organization.
But I found my own way and I found my own way into an
industry that I always wanted tobe in, which was tech investing.
It's been going, you know, it's,it's had its ups and downs, but
it's been going overall pretty darn great.
Definitely better than I could have imagined, especially
looking back only 13 years ago when when I started the firm.
(21:36):
Yeah, but who starts a venture capital firm at 27?
Not too many people. Mostly people that have worked
in venture model before. For three years.
Yeah, if, if that right. So yeah, most.
People that start a venture capital firm are in their 50s
and have worked. 30s or 40s, sure, but it but yeah, have
worked in venture capital for more than an hour.
(21:58):
I just, I didn't start a venturecapital firm.
I started a firm that I wanted to run that did tech advising
and investing in startups, and that was a venture capital
organization, which is what we turned into.
You created it out of thin air, audaciously and daringly.
Daringly and audaciously. Yeah, in a good way.
(22:19):
In a good way. And, and now it's a thing.
So why am I here on the mic? Because there's always been a
little bit of resistance around doing the personal work.
And that includes like, it's easier for me to work than it is
for me to be a dad. I like being a dad and I and I
like the person that I am when Iam a dad, but I also really like
(22:42):
the person that I am when I'm building business.
And so outsourcing comes easy tome when it comes to the
children. But to circle back on family
being the most important thing, you know, I grew up in a, in a
household where I feel like I wasn't bearing witness to my
parents daring greatly. I was the product and they dared
greatly to build a great family,but they kind of neglected
(23:05):
themselves and they lost themselves in the process or.
Maybe they chose to. Or maybe they chose to and did I
overcorrect? I don't know.
Jury's still out on that. One jury's still out, but I
think I'm AI think I'm a darn good dad too, and I think that I
think that I really like being. I like having it all and I
believe that I can if I choose the things that I'm good at and
(23:28):
focus on those across all areas of life.
So working hard now on the personal and the self
exploration isn't just for me. It's for creating a family
album, if you will, a collectionof family stories, if you will,
(23:49):
a reason beyond what's inside ofme that drives me to work.
It's creating a reason to share all of my learnings and my
challenges with the world, but also for my kids.
And I'm sharing all that so thatthey know what it means to dare
greatly to build something. And hopefully they will dare
greatly on their own path and the mistakes they make will be
(24:11):
different than the ones that I did.
How's that land? That sounds like we're, we're
pretty simpatico on this one. Yeah, for different reasons.
And I think we've come at it. Like I said, I am working more
towards staring greatly professionally and you're
working more towards staring greatly personally because you
have the professional kind of figured out.
But we are aligned. I always come back to this one
(24:34):
story. So when I was a kid, I never had
a job. I fixed computers around town as
my as my way of making money. And I did that until I went to
college. And it was a great time to be
fixing computers. Everyone was getting one.
No one knew how to use them. So I would always have this
(24:54):
request that I turned away, thatI turned down.
And the request was, you can probably guess it.
Can you teach me slash my kids slash, you know, my husband,
whatever, how to do what you do.And it's funny because I had a
computer tutor when I was three years old.
Hey, David Frost. But I never wanted to sit down
(25:14):
with somebody and enable them togo through the steps.
I just didn't have it in me. I didn't have the fuse.
I didn't have the patience. And that's come back as a theme
that I think if I can work on togive others the tools, not just
to be doing it and to be covering my work, but actually
to be opening up, sharing the tools, sharing how I think about
(25:36):
things. That seems to be the work that
I've left on the plate to do at a later date that I'm starting
to think about and starting to lean into now.
So. So I guess we have our
experiments then. I think we do OK.
So the most important thing about Darren greatly, I believe
it is remembering that life is about climbing our own mountains
(25:58):
and that can look like many different things.
It doesn't have to be a billion dollar company.
It could be that I'm the head ofthe PTA, but that whatever it
is, that we view our family as abase camp where we are nurtured,
protected and guided in chartingthe course for those next
mountains. What do you think?
(26:19):
I love it. The one thing I'll add that's
particularly important in my case is that we let others see
it, both the good parts, the messy parts and comfortable
parts and the I don't want us and share those.
Great. I love it.
(26:39):
Well, thank you for being here with me today.
Thank you to everyone listening.Yeah, I'm really grateful that
we had this conversation. Me too.
Love you, Goosey. Love you.
Hey, guys, if you're still here,you're definitely our kind of
person. Thanks for spending this time
with us on the most important thing.
If this episode resonated with you, we'd love for you to follow
us wherever you get your podcasts and share it with
(27:01):
someone else. Building family culture on
purpose.
Welcome to The Most Important Thing.
I'm Danielle DeMarco Neufeld. And I'm Greg Neufeld.
Together, we're exploring how ambitious busy families can
build culture at home. Because after all, family is the
most important thing. Hey teammate friends.
Hi everyone, welcome to episode 20. 20 That's right, XXXX.
(00:21):
And the 10th in our wholeheartedParenting Manifesto series.
The penultimate episode, if you will.
For those of you joining us, forthe first time, we've been
taking Brene Brown's Wholehearted Parenting
Manifesto, breaking it down lineby line, and re parenting
ourselves with each line. That's right, it was like a
(00:42):
Trojan horse. It really was.
Yeah, it was a Trojan horse. I thought we were going to be
exploring other people's things.We explored lots of my things
and your things, but lots of people have reached out saying
that they explored their things too.
That's right, things worth exploring.
It's pretty cool and we've been doing some experimentation this
summer. We've had a couple of interview
(01:04):
episodes with some of our friends.
We call them teammate, teammates.
So hope that you've been joiningfor those.
And if you know a teammate, teammate, or if you are a
teammate teammate, we'd love to have you on.
That's right, it takes a village.
It does so. The Wholehearted Parenting
Manifesto is Brene Brown's ode to new children, in a way.
I think it the way she has described it, if I may use her
(01:27):
words instead of yours, sure is that she wrote it and didn't
know if she would ever publish it, but that it's her own
compass towards parenting. Yeah.
And so Brene, this is our ode toyou.
And we are now one more from today away from finishing.
Yes. So the second to last line in
the manifesto, the one that we will be talking about today, is
(01:49):
about Daring Greatly, which she later wrote a book on.
That's right. Yeah, as you begin your
wholehearted journey, the greatest gift that I can give
you is to live and love with my whole heart and to dare greatly.
Shall we talk about in her definition what it means to dare
greatly? And then maybe we can talk about
(02:11):
how we are each daring greatly right now.
Let's do it. OK, cool.
So Brene defines daring greatly as the courage to be vulnerable,
to show up and be seen when you have no control over the
outcome. It comes from Theodore
Roosevelt's famous speech Man inthe Arena.
So she uses this to under score the idea that daring is not
(02:34):
about winning and losing. It's about having the courage to
step into the arena of life, knowing that you might fail, but
choosing to engage with your whole heart anyway.
Is it a weird time to bring up Chamath?
Never. Chamath Poly Hypatia, yes.
Chairman, dictator. I always think of the man in the
arena with Chamath when he was doing all of his Spacs and
(02:58):
everyone was losing money and he's losing money and like he
was just going horribly wrong. And he was like, I'm just in the
arena trying stuff. That's his rhetoric.
So niche, Greg, tell us everybody would love to know the
crossover between team at listeners and all in listeners.
Definitely one there. One me.
I mean, I'm sure there's more. There's probably a few.
There's probably a few. I think we've got a couple that
(03:18):
are that are working in the DC industry that are parenting and
running investment firms and or maybe running venture backed
start-ups. I'd say the crossover is
actually pretty big, and after this episode maybe even bigger.
Yeah, come off, come listen. Sure, anyway.
Where are we going here? OK.
So where are we going here? This.
(03:39):
The greatest gift that I can give to you is to live in love
with my whole heart and to dare greatly.
I This line is a breath of freshair for me.
And it might just be the way I'minterpreting it, but let's go
with it. Yeah.
Because what comes up for me when I hear this is that life is
about climbing our own mountains.
And this idea that we've talked about before as family, as a
(04:01):
base camp. And there's a specific quote
that comes to mind from Carl Jung where he says nothing has a
stronger influence on their children than the unlived life
of a parent. And I love this because I feel
like it gives me license to go and live my life as a potential
(04:24):
way of avoiding putting my children in the therapy chair.
As opposed to so much of what I feel today, which is this mom
guilt, if you will, around. If I want to live my own life,
it will somehow detract from my children's life.
Does that make sense? Of course it does.
(04:46):
So I feel as though I, I guess Itake Renee's words in the
broadest sense, the courage to be vulnerable and the courage to
try new things and the courage to be myself, which is so much
more than just a mom. I love being a mom.
(05:07):
It has been the most transformational experience of
my life, but it is not my whole life.
If I'm being really honest, it'snot even the foundation of my
life. And it feels a little verboden
to say that, but it's the truth.And when I think about daring
greatly, particularly where we are with our family out of the
(05:29):
blocking and tackling years, as I like to call them, and more of
the family as a democracy years,I feel like I'm I'm declaring my
independence, if you will. And I've been thinking a lot
lately about what that looks like.
And it's hard. It is hard in the world of
(05:50):
gentle parenting. It is hard in the world of
social media with trad wives andmoms on Instagram telling me to
lean into the chaos of three different travelling sports
teams on the weekends. And I'm kind of like, I'm trying
not to curse right now. You're allowed.
I'm kind of like, fuck you, that's not what I want to do.
(06:14):
I love my children with my wholeheart and I have no intention of
following them around for the next 15 years.
Let me just tell you emphatically, I will not follow
them around for the next 15 years.
And this is what I really feel in my heart, and I hope that I'm
not alone and I hope to make space for those that are with me
(06:39):
to say that that's OK. There it is.
I guess it is my hope that by living a full life and daring
greatly, I also authorize our children to dare greatly in
their lives as well. Amen.
That said, it does mean that I am going to be outsourcing a lot
(07:02):
of the day-to-day of parenting life.
I'm not going to be the one taking them to ballet or soccer
practice, because while they're exploring their own interests, I
am exploring mine. And it also means that on the
one hand, while I do believe that deeply fulfilling my own
personal life will bring me morecapacity for presence and joy
(07:23):
and meaning when I spend time with them, it also means that
sometimes Maverick is screaming his head off 10 minutes before I
have a very big important clientcall.
And not only do I lead from my not best self, but I go berserk.
I go absolutely nuts because of the stress of it all.
But I guess that's human, you know, it is human.
And 'cause sometimes I think, wow, if I didn't have my hand
(07:46):
and so many different things, maybe I wouldn't freak out at
Maverick for screaming. But it's OK that I want them to
know that Mommy is a whole person with a lot of really
important pursuits that are close to my heart.
The most important thing people typically have been ending their
sentence on podcasts when talking about family with those
(08:08):
words. Family is the most important
thing. And then not going into why.
We set out to explore what thereis beneath those words in this
podcast, and it's interesting because it takes us through this
journey of what it means to be ameaningful participant and
climbing your own mountain at the same time.
(08:31):
And I think the best entrepreneurs can get too
focused on climbing that mountain without letting their
family see them along the way. Because having our kids bear
witness to us climbing those mountains and understanding what
it means, not just closing the door on them, is the difference
between a great entrepreneur anda great entrepreneur that's also
(08:53):
a great parent and role model. Is it crazy that I really want
to be both? No, in fact, Jack Altman,
yesterday Tiffany Zong sent me this tweet, as you know, from
Jack Altman, which I thought wasa little bit simplistic.
But now that I reflect on it, the people I look up to most are
(09:15):
equally amazing at work and withtheir family slash kids.
I don't think that's too much toask for, but I don't think that
it means that you take them to all of their soccer games and
run a business. And that is the trap.
I think a lot of people are trying to fall into or are are
unintentionally falling into, which is trying to have it all
(09:37):
by doing it all. And I think what you're naming
is what a lot of people are feeling, which is I can't, I
have to put on my oxygen mask first.
I have to climb my own mountain and let my kids bear witness.
My children are not my legacy. They are fill in the blank.
(09:58):
My my witness. My witness, Yeah.
I guess it's just, you know, different philosophies.
I don't want to be judgmental towards any other philosophy,
right? But I can tell you that when I
was watching Real Housewives of Miami over the weekend, I guess
it was. And Larsa Pippen said I am
investing in my kids so the fruits of their labor better
(10:18):
come back and take care of me someday.
I was like, heck no. Like that is just not me.
That and I understand that that is a mindset and I hope that it
works out for her. But if anything, I am the
complete opposite. I am the one that is wanting to
live in the here and now. Like, I don't know how much
longer I'm going to live, honestly.
(10:39):
Maybe it's a mortality thing, who knows.
But like, I'm not willing to putoff my dreams until they've left
the nest. Of course not.
And I guess I I'm hoping that there are benefits to climbing
my mountain as our children are growing.
And what that really has meant is that I do need to outsource a
lot of the more time intensive, more rote tasks like carpooling
(11:03):
and doing the laundry and cooking dinner.
But I still try to be involved in holding space for their
feelings and spending intentional time with them.
You know, the first two hours every morning in the last two
hours before bed at night. But it's more of a side by side
activity these days, especially as they grow.
(11:25):
It's you're doing your morning chores.
Well, I'm doing my morning chores and we're talking and
we're interacting as humans about our day as opposed to I'm
waking you up and I'm helping you get dressed and I'm cooking
you breakfast and I'm washing your clothes.
Those are not in our first arc of episodes.
(11:46):
If you think about The Most Important Thing, episodes one
through 8, none of them are taking them to school or picking
them up from school or doing their laundry or putting their
clothes away. None of those things.
And I want to say that on the one hand, these are first world
problems because we can afford to have a nanny to do that and
that is not the case for everyone.
On the other hand, I want to acknowledge that that is a
(12:08):
financial sacrifice. Like there is a world in which I
do not climb my own mountains right now and we don't hire a
nanny that makes umpteen dollarsan hour and we have a different
financial picture. By the way, I would love to be
paying umpteen dollars. An hour.
If there's a way to pay umpteen.Anyway, you understand what I'm
trying to say there. There is a different world where
(12:30):
of course I put my mountain climbing aside and do all of the
things for the children and thenhaving a nanny is not the
largest expense that we have. I saw one of your girls videos
on Instagram, this mother of four boys that you have been
following and she says, you know, taking care of four boys
is this many hours. At this rate, it's $180,000 a
(12:52):
year or something like that. I'm on the clock from this hour
to this hour and the family knows that.
I thought that was pretty cute because it is putting a price on
not having extra help. It is putting a price on what
that means for the family, and hopefully the family can the
benefits of those extra dollars saved.
But in this family, we're spending the money to climb our
own mountain, so we better, well, climb them.
We'd be doing ourselves an injustice if we weren't.
(13:13):
Right. But I want to make clear though
that for us this is, this is nota financial gain goal, no.
Right. No, This is a fulfillment.
This is a personal fulfillment. Who do you want to be?
Goal. Yes, because nannies don't come
cheap. Especially good ones.
This is a push myself to the things that I know I'm capable
of without the constraint of thethings that I know will create
(13:36):
tension and make me feel resentment.
Sure. I just want to say that I have
friends who are amazing stay at home moms and a lot of them had
moms who were amazing stay at home moms and I would just like
to honor that while saying and Ideeply respect that as well.
So I honor and deeply respect that.
That is not me. Like I would go insane.
(13:59):
I would be resentful. So it's just not a skill set
that I possess. And I'm really grateful that you
have seen that in me, accepted that in me and kind of pushed me
out the door at times to say no.We there is no space for you to
do that here. Correct.
Yeah. Well, when in fairness, when we
(14:19):
met, you weren't like, oh, I can't wait to get out of this
9:00 to 5:00 so I can have babies and like that, that was
never going to be you. So I just, I'm trying to honor
the person that I met and remember.
Three weeks before we started trying to have a baby, I was
like, EW, babies are gross. Yeah, yeah, I do.
Hormones are real. They are.
(14:40):
So Darren greatly means to each of us something different.
To you, this clearly means climbing your own mountain right
now. Yeah.
Can I just also say that I thinkit has a bit to do with family
of origin as well, so. What doesn't?
I know, right? But like my mom definitely did
(15:00):
not live for me in a really goodway.
Like in a really good way. She had her own life.
And I guess so, I guess you know, to kind of liken it to
what I said about I have friendswho really appreciated that
their mom was a stay at home momand took care of them in that
way. I really appreciate that mine
didn't and that is one thing that I would like to continue.
(15:23):
Yeah, yeah, there's a lot of story wrapped up in everyone's
own next for them once they havekids, right?
Like the family of origin component, what they were doing
before, you know what they always aspired to do.
I think the the most important thing about climbing your own
mountain is that you're not afraid to just try things.
(15:43):
Yes, and that is the license that I feel that I have in this
family and I hope you feel as well.
Yeah, that is probably it's the lynchpin.
It's the most important thing. So thanks for letting me talk
about Aaron greatly. It's something that.
I not just talking about it, you're doing it.
Thank you. I feel a little, I feel a little
nervous talking about. This.
(16:04):
Honestly, like I said, it feels verboten.
It it feels like something I shouldn't be talking about.
I think you're going to finds that there's a lot of people
here for it and that are doing it.
I think there are a few. I've definitely met a few that
come to mind. I just want to make in the same
way that I, I guess this is thisis the episode where in the same
way that we started this podcastbecause we want family culture
(16:26):
to be spoken about more. This is where I am saying that I
want moms who are daring greatlybecause they really are
passionate about it. I want to hear from them more
too. OK.
And what about you, Sir? What about me?
Yes, what about me? What about you?
Chilling. No, you're many things chilling
(16:47):
is. That What About Me, Daring
Greatly for me has been following the arc of this
podcast. Not necessarily in the creation
or the production, though those are new challenges too, but I
would say in the experimentationand most of all the
introspection. So we started really nice and
(17:11):
soft and gentle with some thingsthat as a family we can do to
get behind. It's so funny you call that arc
soft and gentle, because it's not.
It's actually crisp, clear linesof routines and rituals.
Like actionable things, right? But it felt safer.
Way safer for me. I mean, starting family meetings
it like, you know, it was basically business family.
I'm like, oh, OK, I can do business family.
Dad, that's a guy that I can call up.
(17:34):
He's he's very available. It's been a lovely way to
connect more with our children with you and to build habits and
routines that I think are compounding family meetings,
especially, you know, cannot sayenough good things about family
meetings. I think the problem solving that
our kids are showing up with allows us to be witnesses and
(17:55):
not necessarily like just solving problems for them all
the time, which has been really great.
Now getting into the whole heartof Parenting manifesto topics, I
didn't realize how much work I still had to do in naming a lot
of my unspoken behaviors or habits or patterns or things
(18:17):
that I have just been on my internal narrative that I've
never said out loud. And to share those with you,
that's just called marriage. But to share them with you in a
format where I don't know whose ears they land on and that I'm
OK with that. That for me has been, it's not
just interesting or a little uncomfortable, but it's actually
(18:38):
been really exciting. I think the most exciting part
of that is knowing that I have this path in front of me to do
it more often. And so I think a lot of the
early work that I did was just seeing what showed up and
getting on the mic and talking about it.
I think the work to do is going to be digging a little bit
deeper because I owe it to myself.
(18:59):
You know, I owe it to you. I owe it to the listeners, but I
owe it to myself. I, I owe it to the dads like me
that are climbing in the charts.I think it's like 40% of the
audience actually are dads, which which is, which is pretty
sweet. I owe it to the dads to show
that vulnerability is a masculine trait, to show that
(19:21):
being vulnerable as a dad doesn't mean that I lose my
perspective on what still matters.
Doesn't mean you're going to fall apart.
Doesn't mean I'm going to fall apart.
Doesn't mean you're not still going to be our rock.
Exactly. Yeah.
Can I just say, if I may, this is so this idea of daring
greatly, really showing up vulnerably with courage and
(19:45):
being in the arena is something that I feel that I have done in
my personal and emotional life for a long time now.
And I think it is something thatyou have done in your
professional life for a long time now.
You have been an entrepreneur for how long?
Oh God. Since you were how old?
Since I was 1312, yeah. Yeah.
(20:06):
And showing up vulnerably, courageously, starting your own
business, starting your own venture capital firm with very
little experience, to put it mildly to.
Put it mildly. Right, with two partners who
really wanted to start it with you.
Yeah, right. That is daring greatly, truly,
(20:30):
and you've been doing it every day for more than a decade now.
And so you have really shown up professionally in a courageous
and vulnerable way. And now while I am transitioning
to professionally daring greatly, you are transitioning
to personally and emotionally daring greatly.
So we're kind of like crossing paths, if you will.
(20:51):
Yeah, no, thanks for framing it that way.
For context, I, I started Value Stream in my 20s.
Before that, I worked a little bit in software and started a
couple of fledgling app companies, worked in sales a
little bit. Never really had a large
organization. That gave me probably some of
(21:13):
the lessons that I would have learned a little bit faster had
I worked in a large organization.
But I found my own way and I found my own way into an
industry that I always wanted tobe in, which was tech investing.
It's been going, you know, it's,it's had its ups and downs, but
it's been going overall pretty darn great.
Definitely better than I could have imagined, especially
looking back only 13 years ago when when I started the firm.
(21:36):
Yeah, but who starts a venture capital firm at 27?
Not too many people. Mostly people that have worked
in venture model before. For three years.
Yeah, if, if that right. So yeah, most.
People that start a venture capital firm are in their 50s
and have worked. 30s or 40s, sure, but it but yeah, have
worked in venture capital for more than an hour.
(21:58):
I just, I didn't start a venturecapital firm.
I started a firm that I wanted to run that did tech advising
and investing in startups, and that was a venture capital
organization, which is what we turned into.
You created it out of thin air, audaciously and daringly.
Daringly and audaciously. Yeah, in a good way.
(22:19):
In a good way. And, and now it's a thing.
So why am I here on the mic? Because there's always been a
little bit of resistance around doing the personal work.
And that includes like, it's easier for me to work than it is
for me to be a dad. I like being a dad and I and I
like the person that I am when Iam a dad, but I also really like
(22:42):
the person that I am when I'm building business.
And so outsourcing comes easy tome when it comes to the
children. But to circle back on family
being the most important thing, you know, I grew up in a, in a
household where I feel like I wasn't bearing witness to my
parents daring greatly. I was the product and they dared
greatly to build a great family,but they kind of neglected
(23:05):
themselves and they lost themselves in the process or.
Maybe they chose to. Or maybe they chose to and did I
overcorrect? I don't know.
Jury's still out on that. One jury's still out, but I
think I'm AI think I'm a darn good dad too, and I think that I
think that I really like being. I like having it all and I
believe that I can if I choose the things that I'm good at and
(23:28):
focus on those across all areas of life.
So working hard now on the personal and the self
exploration isn't just for me. It's for creating a family
album, if you will, a collectionof family stories, if you will,
(23:49):
a reason beyond what's inside ofme that drives me to work.
It's creating a reason to share all of my learnings and my
challenges with the world, but also for my kids.
And I'm sharing all that so thatthey know what it means to dare
greatly to build something. And hopefully they will dare
greatly on their own path and the mistakes they make will be
(24:11):
different than the ones that I did.
How's that land? That sounds like we're, we're
pretty simpatico on this one. Yeah, for different reasons.
And I think we've come at it. Like I said, I am working more
towards staring greatly professionally and you're
working more towards staring greatly personally because you
have the professional kind of figured out.
But we are aligned. I always come back to this one
(24:34):
story. So when I was a kid, I never had
a job. I fixed computers around town as
my as my way of making money. And I did that until I went to
college. And it was a great time to be
fixing computers. Everyone was getting one.
No one knew how to use them. So I would always have this
(24:54):
request that I turned away, thatI turned down.
And the request was, you can probably guess it.
Can you teach me slash my kids slash, you know, my husband,
whatever, how to do what you do.And it's funny because I had a
computer tutor when I was three years old.
Hey, David Frost. But I never wanted to sit down
(25:14):
with somebody and enable them togo through the steps.
I just didn't have it in me. I didn't have the fuse.
I didn't have the patience. And that's come back as a theme
that I think if I can work on togive others the tools, not just
to be doing it and to be covering my work, but actually
to be opening up, sharing the tools, sharing how I think about
(25:36):
things. That seems to be the work that
I've left on the plate to do at a later date that I'm starting
to think about and starting to lean into now.
So. So I guess we have our
experiments then. I think we do OK.
So the most important thing about Darren greatly, I believe
it is remembering that life is about climbing our own mountains
(25:58):
and that can look like many different things.
It doesn't have to be a billion dollar company.
It could be that I'm the head ofthe PTA, but that whatever it
is, that we view our family as abase camp where we are nurtured,
protected and guided in chartingthe course for those next
mountains. What do you think?
(26:19):
I love it. The one thing I'll add that's
particularly important in my case is that we let others see
it, both the good parts, the messy parts and comfortable
parts and the I don't want us and share those.
Great. I love it.
(26:39):
Well, thank you for being here with me today.
Thank you to everyone listening.Yeah, I'm really grateful that
we had this conversation. Me too.
Love you, Goosey. Love you.
Hey, guys, if you're still here,you're definitely our kind of
person. Thanks for spending this time
with us on the most important thing.
If this episode resonated with you, we'd love for you to follow
us wherever you get your podcasts and share it with
(27:01):
someone else. Building family culture on
purpose.
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