KLM Podcasts – Episode 3 – The Total Collapse

KLM Podcasts – Episode 3 – The Total Collapse


it was a lovely busy workday afternoon
in Manhattan and Tina Kaplan top executive and face of the New York
startup scene was getting ready to cross the street so it would be maybe a 18 second walk
and I remember leaning against utility pole praying that the light would not
turn green because I didn’t think I could make it to the other side without
having a panic attack and I remember in that moment telling myself I have to get
out of here I just have to get out of here I need to live the exact opposite
life in the exact opposite way and I need to take action immediately and Dena took action immediately this
said her life on a journey the trip that changed everything hi i’m jonathan gruber and this is of
the journey the journey is an original podcast from
KLM Royal Dutch Airlines where we meet extraordinary people whose lives are
transformed by travel dina Kaplan’s story begins in the early 2000s New York
City back then Dina was the CE o Oh a top executive in a company she
co-founded an internet startup called blip TV blip TV had made Dina the it
girl of New York startup scene I got to do some really cool things I got to
spend a lot of time with Warren Buffett because I got named one of fortunes most
powerful entrepreneurs most powerful women entrepreneurs so there’s only ten
a year that are named I mean I just met everyone because I also started hosting
these events called founders club I wanted to bring together the New York
community to try to take on Silicon Valley a bit because there was no
community and no network in New York so she launched founders Club it’s easy to
see how Dena could be the center of a scene to look at her now more than a
decade later in her late 40s she’s super fit impeccably dressed and I’m looking
for the right word here engaged in a way that is both flirty and forceful Dina
and her Club attracted a who’s who of New York types Jimmy Fallon would come a
bunch of other celebrities we had the mayor co-hosted one with us Rupert
Murdoch came so it became a big thing and for a number of years Deena was
herself a big thing you just heard her say that fortune magazine called her one
of the and this is a quote from the magazine most powerful women and Trump
owners as well as Fast Company’s most influential woman of web 2.0
I could read you a whole list of accolades and magazine covers and
articles written about her but I think you get the point
Dena got to this position through grit ability and determination so you’d think
she would probably be feeling pretty good about herself right right so from
the outside you were the very definition of the young female internet and
trumpeter it’s fair to say a hundred percent I was held up as a role model
for founders and especially for women founders and yet how did you really feel
in the middle of I mean that irony of this is that I was completely playing a
role myself 100 percent what do you mean he was all an act because on the inside
I was a mess I was an absolute disaster an absolute disaster a few things were
going on first of all Dena wasn’t just a
workaholic she had a very acute case of impostor syndrome the idea that your
success is all a big mistake and at any moment everyone will realize it’s a
mistake and he’ll be publicly humiliated I think I wondered if I deserve to be
there so I had a lot of people looking at me and I just wondered are they
thinking that I don’t deserve to be where I am and so let me over compensate
for that by just working nan friggin stop so one of the big venture
capitalists that had put significant amount of money in the company I knocked
on my office door one day and said hey how’s it going and he said well I wanted
to talk to you of course everyone in the company thinks you’re doing an amazing
job your your work your quality is above rebuked but I am worried about somebody
meeting you at a conference and thinking that just based on your appearance that
you don’t look like what a CEO of a company of this size and stature should
look like so what I would like from now on is for you to drop your CEO oh tight
all keep doing your job exactly as you’ve done it before but just never use
that title again I wanted to punch him I wanted to scream
I wanted to slam either his head or mine into the wall I was so angry I hung my
hat on that title what did you do I just looked up at him and I said okay why why
did you just say okay because I didn’t want to cause any problems it was that
old pleasing instinct just wanted everyone to like me I just wanted to be
pleased saying the company couldn’t have existed without me at that time because
I was holding all the operations together and yet I was still so worried
about getting fired my name’s Patrick McKenna had the good fortune of
traveling all over the world and meeting people from so many different
backgrounds and have travelled extensively with Dina actually Patrick
McKenna is an entrepreneur himself i Skyped him at his home in California and
asked him how he remembers Dina from this period he says she was quite a mess
she was very very distracted running a million miles an hour trying to manage
every relationship inside and out trying to have total control of everything
around her I would go to New York and visit her in New York and she was very
famous for having ten things to do a night there’s a art event that starts at
6:00 and then we’re gonna go to this founder talk at 6:45 we’re gonna stop by
and say hi to some people at the Soho House for a few minutes and before you
knew it it was midnight and we have gone to six places and said hi to 30 people
but that was a normal Tuesday night it’s almost a sense of not being good at
saying no and why do you think she wouldn’t say no this is how you build
your kind of your ego your credibility your sense of self is by going to all
these different places you’re wanted you’re needed particularly a place like
New York where you had to have this never-ending loop of network
right people go to this but it is but it is good of this and they go to a million
things and you want to stay in that that cycle of external affirmation and Dena’s
problems were getting worse much worse I lost control of my personal life I mean
even to the point that I pushed away my best friend and my family and all I
could think about was that 10 to 20 million dollars that every founder wants
to have to never work again I was having panic attacks and I wasn’t telling
anyone I didn’t tell my best friend I didn’t tell my co-founder my doctor my
parents I just really didn’t even admit it to myself but at the height of one I
don’t know if you’ve ever had one but you feel faint you feel like you’re
about to pass out and it’s like tingles are shooting through your entire body
and you’re about 70 percent convinced that you’re gonna fall on the floor
within the next 10 to 20 seconds it’s terrifying and I was having them
constantly it makes you wonder how did we get here
how did this super capable super smart woman end up such a mess Deena grew up in a pretty well-to-do
family mostly in Pittsburgh Pennsylvania and it was mostly a happy childhood but
if you ask her about her worst moment growing up the event that really shaped
her in many different ways she tell you about her time at a fancy rich kid
summer camp you know that one kid who for whatever reason just can’t fit in
and ends up the butt of everyone’s jokes well that was I was the absolute reject
of the entire camp I mean the kids would steal my clothes when I was showering
and the shower tent was a real walk from where our bunk was and so they wanted to
make me walk naked which when you’re you know 8 9 10 years old is devastating for
a young girl they were threatening to beat me up
and there was one crushing blow my one friend this summer was my little stuffed
Snoopy doll who I absolutely loved and he had that cute big Snoopy nose so I
went on a camping trip for a couple nights hoping that people would be nice
to me because we don’t want to survive the camping on the mountain so I escaped
I mean when I came back Snoopy was hanging from the rafters in a noose and
it was so sad deena told her parents what was going on
but her dad a tough guy from the South Bronx was no real help so Dina decided
to help herself and at the end of that summer I remember telling myself that I
made a vow to myself that I would never be the reject again that I would hone my
social skills so finely that I would be popular for the rest of my life so I
watched the popular kids you could see that there were kids that other kids
wanted to be around and I watched how they would act I would watch their
facial expressions how much they spoke what they would say whether they would
use colloquialisms and expressions or speak plainly and I watched their
behavior and their gestures and I imitated that and then I just trained
myself on a very deep level to never say what I was actually thinking but
actually just to try to be pleasing to everyone around me and just hone did me
this instinct to say whatever I thought the person around me wanted to hear
rather than what was actually on my mind and it worked
Dena became popular and successful in college she even took time to work for
Bill Clinton’s presidential campaign which led to his stint working at the
Clinton White House as her first job after college my fellow Americans I mean
it was just the coolest thing in the world right at the time
young fresh guys right Al Gore Bill Clinton it was such a young vibrant
presidency and we took over DC we took over the restaurants and the clubs and
this and that and so to be in that kind of inner circle of that felt like an
incredible privilege Deena says the White House was great but dream job came
at MTV she worked the Rock the Vote campaign that inspired young people to
get involved in politics Deena covered the presidential campaign
traveled throughout the US and met many rock stars
she was on fire and hung out with the coolest people in the country after MTV
came in on air gig as a TV reporter Deena Kaplan is live on the west side
with the very latest good morning Deena all right Deena Kaplan reporting live
tonight Kaplan Ford weekend today and then came the call from an old
boyfriend who had an idea for a startup she signed on and together they created
blip TV if you’re a gamer you’re probably familiar with blip tv’s content
they host shows made just for the internet distribute it run the ads and
split the profits with the show’s producers this was cutting-edge stuff at
the time and venture capitalists were standing in line to invest blip TVs
success brought Dena a ton of public recognition and a deep private hell I
can’t walk down a street because I might have a panic attack crossing an
intersection and my fear was that a cab would roll over my body and I wouldn’t
even look good for the funeral so I did my hair great every day I did my makeup
perfectly I wear designer clothes and great shoes every single day and I
couldn’t walk so I just took cabs literally everywhere I went if I were
ever by myself everywhere for two years what was the absolute low point I mean
the low point I remember so clearly I mean such an image in my mind somehow I
don’t remember why got dropped off across the street from my office rather
than at my office so it would be maybe a 18 second walk and I remember leaning
against utility pole praying that the light would not turn green because I
didn’t think I could make it to the other side without having a panic attack and I remember in that moment telling
myself I have to get out of here I just have to get out of here I need to
live the exact opposite life in the exact opposite way and I need to take
action immediately so Dena Kaplan acknowledged entrepreneur
face of the New York startup scene and center of a founders movement simply up
and quit she didn’t just quit her job she quit New York till one day I just
had to book a flight to Bali and fly six days later did you know what you were
looking for I had no idea I knew I wanted to be able to walk again
I wanted to be able to cross the street I didn’t know anything else so it’s a
little nuts you can’t cross the street but you can book a flight to Bali I know
in fact they do remember and The Hague on the side of buildings what am i doing
like now I’m in a place where I’m less supported my community’s not here like
in New York but I just knew to get healthy I just needed to live the
opposite life her opposite life on the road wasn’t all that different from her
life back in New York networking fretting and planning things
down to the minute I’m talking to people constantly everywhere I am in Sri Lanka
I’m asking people where they’d come from into in Cambodia Bhutan Myanmar and you
end up with this massive list you know the former CEO Oh in me kept everything
on Evernote country by country and I just had this endless list of places to
go it was a frantic flurry of a world sampler that was so full of the kind of
networking and speed that was so very Deena still it was time away from the
pressures of her life in New York after three and a half months at her hotel’s
rooftop pool in Koh Samui Thailand she became aware that just maybe something
very small had changed it was war most beautiful of course because it’s
Thailand and I didn’t think much of it so I took off my bathing suit cover-up
and I had maybe eating shit on and I’m going swimming and I’m swimming at
sunset and all of a sudden I’m gonna get emotional telling this story I’m crying
because I feel I feel safe I feel safe not only walking but I feel safe
swimming in a pool by myself then I was so proud of myself that I’d /
I had overcome that fear of of walking at that point so strongly that I felt
comfortable swimming alone that sunset this small success encouraged ena to
face her fears head-on one of the biggest fears that I had for my whole
life was scuba diving as a teenager with my parents I’d gone on a scuba diving
trip in the Bahamas and a man that we knew we’d flown over with died on my
very first scuba dive ever it was horrifying it was horrific so I went to
the place that I’d heard was the best scuba changshan and I said hi my name is
Dena someone died on my first scuba diving trip ever and I have panic
attacks and I have trouble breathing above ground but I’d like to go for a
dive tomorrow and they just looked at me and said can
you pay and I said yeah I can pay so I went back I was very lucky cuz I got a
very good-looking instructor and B no one else signed up so I asked my
good-looking instructor if he could hold my hand as we went under the water and
he said yes and when we came up I I came up a different person
I’d conquered one of the biggest fears in my life this was one of the steps of
the trip that helped me gain my confidence to live my life as a normal
human being Patrick who you heard from earlier had
used meditation as a way to conquer his own fears and anxieties he’d been
advising Deena to try it all along he and Deena met on her travels in
Myanmar and frankly Deena may say she was getting better but Patrick he was
less convinced okay this was intense shall we were in
Myanmar we were standing on the side of a road and we need to cross the road
it’s like a five lanes when these big roads and there’s a crosswalk cars
aren’t coming and I say let’s go Deena let’s let’s run across the street it’s
clear opening and she starts to take two steps and completely freezes she’s just
locked in she can’t lose she’s completely paralyzed and I run across
the street I’m like where are you she’s like stuck then I’m saying run
back over I could grab him get back on his sidewalk
and she’s like trembling trembling and this is where we really started to
talk about some of her fear like this is a very specific fear that she had you
have these anxiety attacks that she was really good at hiding but in this case I
was right there with her it’s just maybe it’s more of a metaphor for bigger
things but she just at this moment couldn’t literally cross the street this
is when we really started talking about going inside and dealing with your fear
my recommendation was to find a teacher to find a pop Austin retreat to really
give a serious effort to training in mindfulness meditation Vipassana is a
silent form of meditation often practiced in a retreat for 10 days or
more Dena booked a flight to India the next day with no plans whatsoever I land
in Indiana I’m terrified that people get sick and then there’s crowded and it’s
hot and I’m a woman traveling alone so I land and there’s this cute guy walking
off the plane just behind me and he says so what are your plans for India and I
just looked at him and said I have no plans and I’m scared to be here and he
said oh I’m going on a 10-day silent retreat you want to come and so as
serendipity happens Patrick’s voice which was now less than 24 hours old in
my mind saying what he had told me the day before came to me and I just looked
at this guy and I said yes I’m in and he said what no I mean I’m really
going and I said no I am in I’ll go with you and I go and it changed
my life so I walk in and we have to take vows no
lying no killing no stealing no sexual misconduct even with yourself leave to
sign your name to alright whatever it’s ten days that’s fine little do I know
that there is no soap and no toilet paper and it’s going to be 120 degrees
the entire time no air conditioning hotter inside than outside it was India
to the most extreme degree that you could possibly imagine the conditions
were insane and then what happened and beginning on day 4 it was like I saw
this light at the end of a tunnel which was peacefulness the first three days
you just want to kill somebody or yourself at me it’s really really hard
the voices in your head are so loud and you can’t escape yourself there was no
one to be charming – there was no one to work it with there was no one to
distract myself from myself with beginning on day four your mind is like
glass there’s absolutely no thoughts you could look up at a tree and look at that
tree for three hours perfectly happy because there’s nothing in your head
telling you that you should be doing anything differently at that moment
beginning on day five you start doing open-heart surgery on your brain
essentially your personality and what I saw was this memory like the pond Steve
from Harry Potter like that Dumbledore has it was this memory of me as a little
kid at summer camp vowing to be popular for the rest of my life and I realized
for the first time as an adult in my whole life that I’d optimized my entire
life to just try to be pleasing to everyone at the cost of ever being
authentic or saying what was on my mind and in that moment I decided that that
piece of the jigsaw puzzle of my personality was no longer serving me and
I decided to literally take it out and put in this new piece that was authentic
and at the moment that that happened it was like this flash of lightning shot up
my foot loaded through my legs went through my
torso and then just had this firework explosion above my head and his voice
came to me that said you’re gonna come out of this retreat a better person and
everyone should have the chance to experience this but it doesn’t need to
be this hard so when you come out of this retreat you’ll start a company to
bring meditation to the mainstream you’ll make it beautiful and light huh
don’t be soap and toilet paper and you’ll call it you’ll call it the path Dinah’s ten days of silence really did
change everything she felt free to break her fix patterns of fear she no longer
felt like an imposter and most importantly she felt like if she could
do it others could do it too she kept on traveling and then finally booked one
final flight back to New York you guys ready for a little moment before all of
the input that we’ll have for the rest of the day let’s meditate and this is
Deena in 2016 she actually created a Center for
meditation called the path in New York there is soap and toilet paper and while
everyone is welcome the paths website shows a group of 30-something sitting
Lotus position in suits and business attire
this is Deena leading a group meditation at a tech conference at the path we say
that there are hundreds if not thousands of types of meditation in the world we
break them down into four categories and we teach all four mindfulness mantra
energizing and then meditation to help you accomplish a goal Patrick says that
while most people say they were transformed by a 10-day mindfulness
retreat Deena actually became a very different person when she said I am
going to create something around this experience this wasn’t about pleasing
anybody and that’s a big fundamental change the need for external validation
on what she was going to do in any given day or week or night had dissipated
significantly well when you would go to visit her in New York for example and
you guys would go for a night out how was that different from your previous
visits so different I was coming to New York and she says I’m gonna organize a
dinner for you bring a bunch of great people around the table and we’re gonna
have a dinner and we went to a place in the West Village beautiful little
boutique restaurant that doesn’t have a bunch of cash I had a table for 8:00 and
we had a two and a half hour dinner and every single person at the table was
engaged and talking and we had a depth of conversation this is literally the
first time after I visited her after she came back from this trip
this was how we kind of inaugurated our reconnection so that’s creating a very
different container for friendship Dena can now cross the streets
unencumbered by anxiety but if you’d look at Dena even now she’s not exactly
like a Buddhist monk full of calm gravitas she’s still a bundle of energy
ambition and you’ve probably noticed her tendency to use 20 words when 10 will do
so I asked her Dena after all you’ve gone through to get
where you are are you happy you do feel fulfilled I know my next
mission you’re right I am ambitious I’m ambitious and I know that I need to
write a book so that’s the next step are you happy I am happy I think literally
my skin looks better because I meditate I have a I get my validation much more
from within so I’m aware of my triggers now I still have this thing like hate to
be rejected it takes me back to that little kid and so I camp but we all have
moments where things happen and now my recovery time is less than half an hour
so maybe I’ll get upset we all have things so we’ll get upset about but I
have a huge resilience so yes I think she’s never been happier
I think she is truly truly satisfied I think that she’s feeling at with him
this I think that she is feeling satisfied and that she feels like she’s
doing the right things and so my bottom line answer is yeah I think she’s happy
the trip was the best thing I’ve ever done it was the most non-obvious thing
this super ambitious girl has ever done but it changed me a friend of mine said
you take the fish out of the water you learn a lot about the fish I learned so
much about myself by putting myself and all sorts of difficult and uncomfortable
situations and it is by far the best thing I’ve ever done in my entire life Dina Kaplan if you want to know more
about Dina or the path check out our website podcast KLM comm you’ve been
listening to the journey an original podcast brought to you by KLM Royal
Dutch Airlines to hear more stories about the trip that changed everything
goto podcast KLM comm and why not review us on Apple podcasts it helps other
listeners find the show thank you so much for listening
I’m Jonathan Gruber you

2 thoughts on “KLM Podcasts – Episode 3 – The Total Collapse

Leave a Reply

Your email address will not be published. Required fields are marked *