June 24, 2025 • 64 mins
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Tessa Whittaker had the career, the relationship, the apartment. On paper, everything made sense. But inside, something was quietly breaking.
After years of high performance and holding it all together, she made the call to walk away from it. Her engagement. Her country. Her old sense of self. What followed wasn’t a clean pivot. It was a full system reset.
In this conversation, Tessa opens up about the slow drift into burnout, the cost of abandoning your inner signals, and what it takes to build a life that actually feels like yours. It’s about nervous system awareness, boundaries that hold, and redefining success without self-betrayal.
This one isn’t about burnout recovery tips. It’s about waking up.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:01):
In the following interview, I sit down with Tessa Whitaker,
the VP of Rev OPS at Zoom Info and Chapter Head of Pavilion in
Miami. We talked through using
workaholism as a distraction tool and trying to process and
navigate grief in a high paced environment that never slows
down. Grief brought on from the end of
(00:24):
long term relationships and fromdeath and losing loved ones and
folks that are really really close to you.
And then we chat about checking all of those boxes that we
believe will bring us happiness,but somehow still feeling empty.
And then having the courage on the other side of that to start
(00:44):
all over and completely reinventyourself from the ground up.
And before we get into it, I do want to give a quick shout out
to our partners optimizing dot AI and Dream Fuel for bringing
this project to life. You know, most of us are heading
into a new quarter staring down the barrel of yet another big
(01:05):
quarterly target and goal for ourselves and our teams.
Dream Fuel gives leaders and their teams the tools,
practices, and mindset to achieve seemingly impossible
goals. I know it did for me personally.
Their team of elite performance coaches can give you an edge
when everyone is counting on youto win.
(01:26):
And as of now, they are giving listeners of the wake up call a
complimentary 1 to one coaching session.
Now of course they can't do thisfor everyone.
I have forever. So I would run and join the wait
list as soon as possible. And optimizing that AI gives you
the ability to finally stop guessing how your users are
(01:48):
feeling. Almost sounds like sci-fi.
But we can now use AI through a webcam to monitor vital signs,
emotions and stress levels. You can build true real time
emotional intelligence into yourdigital experiences.
You can find out more about bothof our partners in the show
notes below. Please go support them.
(02:10):
They are great teams doing greatwork and making our physical and
digital realities a better place.
This conversation you're about to listen to really hit home
with me, and I know it will resonate with many of you as
well. Please enjoy it.
(02:34):
Miss Tessa Whitaker, welcome. Hello, I'm excited to be on this
Scott. I'm excited to have you excited,
nervous. You know, these conversations
are so different. You know, I've had a podcast for
the greater part of like 6 years, but you know, really
diving into it with people, it'slike a whole other energy.
(02:58):
And hey, you never know what you're going to expect, you
know? Yeah.
I mean, I, I probably am more more nervous for having this
conversation than any podcast I've ever done.
I think back to like the very first one that I did.
And I would say this is pretty equitable to that.
(03:19):
Well, thank you for being brave enough to to come on and, and
share some of your, your story. And you have a podcast of your
own now. Like you're out there, you're
doing all these podcasts. So I'm like almost honored that
you're actually nervous for thisone.
Yeah, well, I mean, I think it'seasier to talk about Vita Visa
sometimes than it is about yourself.
(03:41):
But I've always been an open book and authenticity is one of
my top values. And so if I can share a little
bit more about my journey and maybe help people, I think it's
worth the the feeling of uncomfort.
Totally, totally. I know you know, in the past
when I've been going through it,it can feel really lonely when
(04:05):
you flip open social media, whether it's Instagram or
LinkedIn and you're just having like the worst day.
You're going through all of these things and you flip it
open and everything's up and to the right.
Everyone somehow had a Unicorn company and everyone's happy and
there's, you know, photos with their beautiful families and
(04:26):
you're like, what is what is wrong with me?
You know so. Why is everyone in the South of
France but me? Right where's?
Where's my flight to Mykonos? Yeah, and I think like, I mean,
I'm guilty of it as much as as much as anyone.
I mean, I'm posting the photos where I'm at an event or, you
(04:48):
know, my outfit and hair is perfect and I'm surrounded by
all these incredible people and I'm in different cities.
But I think that's just, you know, the highlights You're,
you're posting all of those incredible moments, but there's
so much that's in between. For sure.
And you're just actually straight off of the GTM fund
(05:11):
AGM. How was that in New York?
Great. It was great.
It's funny how so many people that you meet over the years
just truly become your real friends and like the community,
especially from GTM fund or now that I'm doing Pavilion or Zoom
info folks like they are all part of my not all, but a lot of
(05:32):
them become a part of my inner circle.
So it feels like a lot of fun and when you are in your
day-to-day life, there's a lot of people that maybe aren't
focused on the same things that you're focused on or don't care
about the same things you care about.
So when you're in a room full ofpeople that are excited about
the same things, it's just a different kind of energy that
you absorb and it's motivating and inspiring.
(05:53):
So it was a really, it was a good couple of days.
New York is exhausting. I when I'm there, I don't sleep.
It's like meeting after meeting or going to see friends and then
being in rooms full of people. And so when I get back to Miami,
it's always nice to just relax. I hear that, I spent like 2-2
(06:16):
months in New York last year andnot a good city for me.
Turns out it's a lot of fun. I just, I just don't know how
people do it. Like there's the hustle culture
in work, but it also permeates like everything, like social
life is heightened, fitness is heightened.
(06:36):
Like somehow people are working 12 hour days and then going out
and then they're at like a Berry's class at 7:00 AM.
Oh my God. I can do this for a short period
of time, but not much after that.
Yeah, I did it for, I think it was a little like maybe like 7
or 8 weeks last summer and you just don't sleep.
Like you work the 12 hour day, you do your workout, you get
(06:57):
your steps in, you go to happy hour, you go to dinner, you
repeat. There's a lot of alcohol and
it's just exhausting and you just keep doing it.
But like, I'm definitely not my best version of myself in that
environment. And it's funny because people
think about Miami as being this like, party hub and go out all
the time, which certainly there are a lot of people that do
(07:19):
that, but it's also this huge community of people that are
really focused on Wellness and biohacking and fitness and just
being the absolute, you know, most healthy version of
yourself. And so what's funny is I moved
to Miami not even realizing thatwas such a big part of the
culture or a subculture that existed here.
And I feel like I'm absolutely now the best version of myself
(07:41):
because of it. I love to hear that.
Yeah, it's been, I think that's a really good segue into talking
a little bit about your, your story and your your
transformation. You know, I've been incredibly
fortunate that you became an LP in the fund I got to meet you at
a few years back and it was kindof at this for both of us really
(08:04):
transitional phase of our our lives.
To that's so funny. No, I, I remember that retreat.
So that was right after I becamean LP and I was, you know,
flying out from Toronto. So I lived at Toronto, in
Toronto at that time, and I showed up in San Francisco and
it was three days after calling off my engagement.
(08:27):
And so I get there and I think it was even, it was the weekend
before Dreamforce. And I remember, you know,
showing up at this thing. I didn't know anybody.
And I think maybe I was still inshock of everything that I was
going through that I kind of just like introduced myself and
I was like, hi, I'm Tessa Whitaker and I work at Zoom Info
and I called off my engagement three days ago and I'm not
(08:49):
wearing a ring. And, you know, it's funny is I
think probably the reason I havesuch great friends that have
become LP's was because in that moment, like, it was straight
vulnerability. Like I was my most authentic
self. Like I had no ability, no
energy, no capacity to like havesome sort of professional shell.
(09:09):
It was what you see is what you get.
And I need so many incredible friends that I know will be
lifelong friends because of thatweekend.
But I mean, I was living a completely different life at
that time. Yeah.
So tell me a little bit about, you know, that that life like
that's super intense going through a a breakup like that.
(09:33):
And you know, for the listeners at that same time period, mine
was a little bit later, it was about 3 months.
I had the same thing, you know, happened to me.
So we kind of bonded over that and I I know the intensity of of
feelings that that come with that, but walk me through kind
(09:54):
of that that time period becauseof.
Course. The craziest part to me and and
sorry, it was like, oh shit, like nothing stops like I'm
supposed to go to work right now, like I'm what is going on?
Like I needed A at least a monthjust to like try and process
(10:14):
what was happening and like there's no space for that in
this kind of modern really fast moving world.
Yeah, no, it's just business as usual.
And you're kind of going throughthis grieving period.
Well, it's funny. So, you know, I grew up in
Michigan, and I moved out to California like a week after I
turned 18. And I went to school in Southern
(10:36):
California, went to UCLA, and then shortly after graduating, I
moved up to San Francisco. And within about a year and a
half, I fell into a tech job in San Francisco at Salesforce.
I was there for almost a decade and they moved me to London.
And so this is relevant kind of to this part of the story
because when I was in London, I met a Canadian and I always joke
(10:58):
with, you know, you Scott or Paul about, you know, my
feelings about Canada, which I'msure this Canadians listening.
So I'll be nice, but I'm still traumatized.
And I, I was there for three years and it was like the most
incredible time. Like I was in so in alignment in
London, you know, I was obsessedwith fitness.
(11:18):
I had a really great job. I traveled all the time.
And my, my ex fiance at the timeneeded to come back to North
America. And I remember saying like, I
don't want to move to Toronto. I'm not interested in living in
Canada. Like for me, where I live, it's
so important. Like it is, it is one of the
most important things to me is being in alignment.
(11:38):
Like I, I've never understood why someone wouldn't want to
live where they want a vacation because then you get to like
wake up every day and your surroundings are in alignment
with the things that you love. And so we kind of made this
agreement. We moved to New York.
So I moved to New York. I was living in West Chelsea, he
was in Toronto coming back and forth and going through this
process of getting the paperworkto move to New York.
(12:03):
And then it was March 2020 and the borders were shutting and we
kind of had to make this decision.
Salesforce was like, yeah, we'llfigure it out.
We'll get your work permit, likefeel free to go to Canada.
And next thing I know, I'm living in Toronto.
And what was meant to be a few months ended up being almost
four years. And so I was living in Toronto.
(12:26):
And, you know, I think like, youknow, the person I was engaged
with, he's a great guy. We're still friends.
We're still friendly, like he's a wonderful person.
But I think really living together for the first time,
being in the pandemic, being in Toronto, dealing with like those
winters that never ended, I was completely out of alignment with
myself. And I even look at pictures from
(12:47):
that time, like I look like a complete different person.
I have friends that say I was almost like a muted version of
myself. And, you know, I have a very
social person. I didn't really make that many
friends in Toronto, maybe like one or two.
And I just dealt with it by throwing myself into work.
And it wasn't like the healthy way that I work now, which is
(13:10):
like it gives me energy and I, Ilove it.
It was all I care about. All I think about, all I want to
do is work because that's what I, that's what I felt.
That's the only thing I felt that I had.
And I remember being there and being like, OK, if my career is
going well, then I can be happy.And then it was funny.
(13:31):
I started going down, I think, this path that a lot of people
do when they start to become successful for the first time.
And I was like, OK, if I get thecar that I've always wanted,
I'll be happy. And then I got the car.
And then it was like, all right,if I get this dog, I've always
wanted a dog, then I'll be happy.
(13:51):
I want to get a Cabapoo. And then I remember it was OK if
I buy a house South of Queen in the Beaches and I can walk on
the boardwalk every day. Like I couldn't do that in any
other city. Like if I do that, I'll be
happy. And I remember sitting there and
I'm like, in this house and I'vegot this dog and I've got the
fiance and I've got the ring andI've got the car and I was this
(14:17):
shell of a person and I was, I was terrified.
I didn't know what to do. I didn't know how to get out.
And I just kept thinking like, this can't be my life like that.
This can't be my life. But maybe if I make more money
and I buy more things or I, you know, I, I hired A stylist, I
got all new clothes. Like I was doing everything.
But it was funny. It was like, throw myself into
(14:38):
work to distract myself and thenmaybe buy these things and maybe
I'll be happy. And it's just none of it was
working. And I, I didn't realize it even
myself. Like I was so numb to it at that
point that it took two friends visiting that summer.
So this would have been, you know, a month or two before I
(14:59):
met you. Scott and my first friend came
to visit from the UK and we wentout to dinner and she said, I
think you, I think you've got a leave your partner.
And it what was funny about thatis like she's very British and
very proper and British. My British friends probably
wouldn't overstepped that boundary ever before.
And I was like, wait, what are you talking about?
(15:22):
And then it was like instant I started looking around and I was
like, Oh my gosh. But it like she was the first
person and the only person that said something to me.
And then coincidentally, 2 weekslater, my other best friend from
London came to visit and we're up at a lake, we're in Muskoka,
or in Port Carling. And I say to her, you know, this
other friend said this thing andshe's like, Oh my God, thank
(15:42):
God. She's like, you're miserable.
And I was like, I am, I didn't know.
And it was funny. We finished out that week and I
was really quiet and not entirely myself.
And we dropped them off at the airport.
We went back to our house in Toronto and I was like, hey, so
think we should call this off? And it was like the most like,
(16:04):
nice and lovely conversation. Canadians are like, very, very
nice. And we didn't even fight.
We just agreed. And then, I don't know, three
days later I was on a flight to San Francisco.
Wow, wow. I mean, yeah, I'm almost,
there's so many parallels between our our journeys that
(16:27):
it's kind of like scary to, to listen to that.
And I guess also kind of beautiful because you do feel
like, oh, this is only happeningto me or something's wrong with
me. And it's interesting, you know,
as I was listening to that, I had a very, very similar
experience of like, you get in these positions where you sort
(16:51):
of like strip away your own identity or you lose yourself a
little bit. And I think that is when you
have to really be on the watch for what you're attaching your
identity to. And, you know, for me, like you,
it was success. It was the fund.
If the fund was doing well, I was doing well and nothing else,
(17:13):
you know, mattered beyond that. And then it also made every
sacrifice that I was making in my mental or physical health,
whatever it may be, it was worthit because it I would look at
this thing and make, OK, that isme.
And that's going well. So I must be OK.
And you can sort of delude yourself into doing this for
(17:36):
really long periods of time. So you're so lucky to have those
two, you know, great friends, you know, if there's someone
who's listening to this that maybe doesn't have a great
support system around them rightnow, but maybe they feel like
(17:59):
that muted version of themselves.
And I think it's a really good way of, of putting it.
I think I was a a muted version of myself for about four years,
heightened in some ways that I would over almost overcompensate
in some of the other areas of mypersonality, but certainly muted
in like who I actually believe II am.
(18:19):
What would you say to that person or what would you say to
Tessa before your friends, you know, came and and acted as a
mirror for you? Oh.
My gosh, what a great question. I think like it sounds so cliche
or cheesy, but it's just, it's, it's never too late to start
(18:43):
over. And I think about I was so
afraid that I would be too old to ever meet anyone again or
like, I can't imagine dating someone or you know, or want
someone wanting to date me. I was 32.
I'm like 4 years old. I mean, I'm 36 now and, and I
(19:08):
remember because I, you know, I had those thoughts over time and
I was, and so it was just this fear of like, I'm too old to
start over. And now from when I started
having those thoughts to now, like I feel so young and I
actually feel younger now than Idid then because I'm living a
more authentic life. But I think the thing even
(19:33):
outside of that, I would tell myself is when you start
negotiating with yourself in your head, that means you're not
listening to your gut. And like, I spent a lot of time
negotiating with myself and or trying to convince myself that
the feelings that I was having weren't valid.
(19:55):
But really, that was that was mygut, that was my inner self
telling me that it was time to make a change, but I wasn't
ready to hear it. And so I have this big thing
that I think about all the time because I don't negotiate with
(20:15):
myself anymore. And that can be when I'm
negotiating with myself about a relationship or negotiating with
myself about a job or the big one would just be like a
day-to-day negotiating with myself of like, if you don't
work out now, you can work out later.
Like I just don't have those conversations anymore.
I just do what I want to do in that moment and not try to talk
(20:41):
myself out of something because it'll be hard.
It's interesting that you you bring that up.
It's very, very coby of you, this, this mentality, but it's
something I've been, I've been thinking about, like I have more
kind of free time now. And you know, I'm thinking about
where I want to spend it. And I'm really focused on health
(21:01):
and Wellness and, and spirituality.
But if you know, I'm honest withmyself, I'm still pretty fucking
burnt out and my nervous system is pretty shot.
And, and so, you know, I, I havethese negotiations with myself
all the time and coming from theworld of sales and BC what's
frustrating is I'm a pretty damngood negotiator, including with
(21:24):
myself. And so that is something I'm
trying to, to integrate more, talk me through that, that
mentality. So let's say you have a really
hard decision to make. You have a tough conversation at
work or it's 6:00 AM. You don't want to go to that
class. Like what is the process?
Because you're human. You're going to have this little
(21:45):
voice in your head when you don't want to do something.
Walk me through the the process in your mind because I think
it's something I need to learn right now.
Sure, I think that I've gotten better with it through cold
plunging, which sounds like so like tech founder, like cold
pledges solve everything. But no, this practice of like
(22:06):
you go in and you instantly haveto get centered and focus and
clear your mind. It's it's really practicing
mindfulness. And so the thing, it's like when
I that alarm goes off at 5:30 and I'm getting out of bed and I
have to go for a run. So I'm training for a marathon
right now. I'm running New York in
November. Congrats.
(22:27):
Thank you. I don't well.
Congratulate you after. And I don't want to go on that
run. And I'm like starting to go
through, OK, well, if I don't run now, I can run later.
And I start to identify that negotiate negotiation that's
starting to happen. It's like, I'm just going to
practice mindfulness and quit thinking about it and just get
(22:50):
really present and just keep moving forward.
So like, I'm not going to think about when I, like, I'm not
going to even entertain a conversation with myself.
I'm just going to keep putting 1foot in front of the other and
stop thinking about what I'm about to do until I'm out front
and starting the run. And it's funny, I, it like
(23:10):
reminds me so much of like the first time I've gone skydiving.
The first time I went skydiving,I've gone twice and it was, you
know, me getting in a plane, I'mlike, I'm not thinking about
what I'm about to do. I'm like scooching forward in
the plane. I'm like, I'm not thinking about
what I'm about to do. Like just not allowing myself to
even think about what was next. Just continuing to go forward
(23:32):
until like you're hanging out ofthe plane and you're, you're
like, OK, well, actually I'm doing this and I think about
just not allowing yourself to even think about an alternative.
And it's just like being presentand moving forward.
I like that I there's this quoteand I'll probably say it way too
much on this podcast, but I really like it and it's the
(23:55):
quote is discipline is the highest form of self love.
And I really, really resonate with that because you're, you're
basically sacrificing your, you're now for a better version
that your, your future self getsto live.
So like what a beautiful thing to do.
And I would say making that harddecision going back to kind of,
(24:21):
we'll call it the wake up call of, of leaving your partner and
your whole life and your dog andall these things behind like
that was an act, a really deep act of self love.
And I want to like commend you for for doing that and for how
(24:44):
did you get the courage to do that.
You know, it's so funny because it's so similar to what I just
said. It was, you know, the friends
that were there. This is all within a three-week
period. And it was, we dropped them at
the airport and then an hour later I did it.
It was almost like I made the decision and I didn't allow
(25:09):
myself to think about all the things that were going to happen
next. I was just moving forward to
what I knew was the next step. And I think sometimes, so often
people think of, OK, I know I need to do this thing, but that
this, I have to figure this out.I have to figure this out.
I have to figure this out, and the truth is, is you don't need
(25:31):
to figure out absolutely everything if you're going to
make a decision to change your life.
You just have to make the decision to change your life and
then figure it out as you go. Do you think you've got better
over the years and through this transformation of like trusting
your gut? Yes.
(25:52):
I mean, I still, I feel like I still get tested.
There's certainly been things inthe last year where I definitely
was ignoring my gut, but I, I think now I listen to it even
more. The more that you lean in and
you make decisions based on yourgut that are in alignment with
(26:15):
who you are and your values or, or who you want to be, the
easier it gets. And if we're honest with
ourselves, I think we know when we're out of that alignment.
And I almost think of it as likethis heightened consciousness
that through making really hard decisions that were in alignment
with truly who I am, you know, I've raised my consciousness
(26:39):
quite a bit. But of course, there's still
things where I'll, I'll do something or, or ignore myself
and then I can feel it. And then maybe eventually I get
to the point where I make the right decision and then I'll be
looking back and I'll be like, I, I knew, I knew exactly what I
was doing and I was completely out of alignment and I was
ignoring, ignoring my gut. But I think following your gut
(27:03):
really it's just following, you know, being in alignment is so
important. And I think a lot of people live
out of alignment. And when you're in, when you are
in alignment, like work doesn't burn me out anymore.
It gives me energy because I, I love what I'm doing.
And not only am I doing things, you know, with my job during the
day, but then outside of work, Ido a lot of things that are
(27:26):
considered work. But it doesn't feel that way
because I'm being pulled. I'm not pushing because I'm in
alignment. That alignment is such a crucial
piece and I definitely don't want listeners of this podcast
to walk away with like ambition is bad or like, you know, don't
don't go do hard things. Like that is not the message I'm
(27:48):
I'm trying to push at all. It's more exactly what you said.
Like if you can find your alignment, your true calling,
your purpose, your why, all of you know, these cliche things
like the activities are going tofill your cup.
They're not going to to drain it.
And you talked about raising consciousness has would you
(28:09):
consider yourself like a a spiritual person, a religious
person? Has that played an aspect into
this, this growth you've had? Yeah.
I I would say I probably am morespiritual, but I wouldn't label
myself as anything. The last year and a half, I've
spent a lot of time trying to understand myself, you know,
(28:34):
reading like every book there isaround attachment theory or, you
know, going to therapy consistently for the very first
time to, you know, like having crazy conversations with
spiritual advisors and soul readers in Tulum.
Like I've tried it all, but justreally trying to figure out how
(29:01):
I live the most authentic version of myself and that I
wake up every day excited to be doing what I'm doing because I
never want to feel like I'm not waking up every day living the
life that I want to live again. And I lived that life and I was
miserable. And so, you know, I think
getting to know myself better has been so important, that
(29:25):
journey, but there's still so much that I need to figure out,
but I have no idea what to do. So things are going really well
at work. And I, you know, I think like my
ambition is fueling me. It's pulling me.
I'm excited right now. Like it is not burning me out.
And I work way more now than I even did then, but it's all the
(29:46):
things that I want to be doing and thinking about.
And so it's really exciting in terms of dating or anything
else. Like I have no idea what to do
there, how to figure that out. But the work stuff is great and,
and being healthy and, you know,living in Miami and being in the
(30:06):
sun every day, training for a marathon, you know, cool plunge,
sauna practice. There's so much that that is
going really great. But I designed the life that I
wanted and surrounded myself with the people that are really
filling the cup. I love, I love to hear that.
And I think, you know, when you go down this path of like
(30:30):
alignment, you know, you talk about still figuring it out.
Like I don't think that path, there is no end goal, there is
no outcome. You know, we're, we're all going
to be figuring it out hopefully deep into our, our 90s and
staying curious and exploring new things.
You mentioned therapy. That's been a big part of kind
of my, my growth. I think I fired like 6
(30:53):
therapists at one point. I had like a spiritual teacher,
a therapist and like a performance coach going because
I was losing my mind. How, how has your experience
with therapy been going for the first time in your 30s?
Because it reminds me of what you said earlier.
It's like it's, it's never too late.
(31:14):
And I think there's people that write off therapy simply because
it's never been part of their life.
So they're like, oh, I'm good. Like I've always dealt with
stuff. Why do I need to do this thing?
That's such a great question. So I think people feel, and I
guess maybe I'm projecting, I felt that starting therapy would
be too hard because there was somuch context like, Oh my gosh,
(31:35):
like, how am I going to fill, you know, fill in this woman or
man with 36 years of my life? And there's no way that they can
help me unless they have every single detail of everything I've
been through forever. And I just don't think that's
right. And in fact, when you start
(31:56):
going, you realize quickly that like certainly they'll be themes
that you bring up or, or certainthings that you talk about, but
it doesn't have to be in order of every year and everything
that you've ever done to get to this point.
It can really just be what you're working through in that
moment or that week or that month that they can really help
(32:17):
you get through by asking you questions that make you look
within yourself or even challenge how you're thinking
about something that you're not capable of challenging yourself.
And so just getting started. Yeah, I would urge everyone to
to get started if it's not part of your practice.
(32:37):
And yeah, I'm, I'm with you on this idea.
I think that's part of why I've drawn to traveling so much.
So like, if you meet a new therapist, let's say they're
meeting the Tessa, that is that person, you know, you, you want
to explain all this context, butthey don't really like care.
You can dive into that later. They're seeing you for you and
(32:59):
where you're at in that moment. And similar when you're meeting
new people on the road, it's kind of like this brand new
mirror that shows you who you are in that present moment,
which can be incredibly powerful.
I'm like, oh, maybe I have made some headway or, oh, shit, that
that's not how I wanted to show up.
Maybe I haven't made some headway.
(33:21):
So yeah, that's, that's big. OK, I want to.
Yeah, go ahead. I was going to say something
that you said about how people that meet you where you are or
where you are now, they are seeing who you are, you know, as
you become like who you, not whoyou were five years ago or 10
years ago. And you know, I've, I've moved
(33:43):
quite a bit every three or four years.
And I'm so fortunate that I've made a lot of friends every time
I've moved. But it is funny how people that
have known you before almost hold you to a standard of who
you were before. And they're not always
comfortable with that change or that growth.
And that's been something that'sbeen very interesting for me to
to witness. Yeah, I've seen it first hand.
(34:06):
One of my really, really dear friends party pretty hard when
he was younger, I guess we all did.
But he, you know, especially did.
And, you know, he grew out of that phase, became, did a ton of
work on himself. He's the best guy ever, but a
lot of people would mirror that person back to him.
(34:29):
And so it was almost like a selffulfilling prophecy because this
is how all the people saw him. So sometimes when he was out, he
would like just go into that character again.
And it it took him changing his environment to fully flourish
and now he's like killing it andmuch more kind of aligned.
But it is interesting. You kind of have to help people
(34:54):
update their software of you, You know, it's like, here's
here's who I'm trying to be. This is like the new vision.
And sometimes that's even a conversation, you know it, that
you can't just expect everyone to, you know, catch up with all
these things that that you're doing.
Yeah. I agree.
OK. So I want to go maybe to an
(35:15):
uncomfortable period, which and and this is maybe projecting,
but you make this huge decision.You know, you build this life
that you thought you always wanted.
You get it. You realize this is not the
thing you walk away when that big moment happens.
(35:36):
I know for me when my breakup happened, also leaving, you
know, the fun stepping down. There's this moment where you
get a bunch of chemicals in yourbrain and you're so excited and
you're like, I, this is like, this is new and this is
exciting. And then there's kind of this
valley that comes and it's filled with self doubt.
(35:59):
Oh my God, what did I do? Why did I do this?
You start like very much a grieving process of this old
life and this old identity. And it can be really, really
painful. Is that something that you went
through as you were rebuilding? It's funny.
(36:21):
So initially no. But when I, I went through the,
the process, moving to Miami from Toronto, getting the condo,
starting, you know, this new life in Miami, I was living my
absolute best life. And I remember I never even
(36:42):
cried. Like there was no emotion.
I was so relieved. I was so excited.
I just was moving fast and really eager to see what kind of
life that I would build. I was just so excited to be
moving forward. And it was funny as I had this
really short relationship last summer.
(37:03):
I mean, it must have been, I don't know, 10 weeks long, maybe
last 8 weeks, and it ended pretty badly.
And I remember after that, like it was the most devastated that
I have ever been. But of course, it wasn't, you
know, about that breakup. It was that for whatever reason
(37:25):
that I had turned this faucet off on having any emotion and
going through this kind of shortbut fun and intense relationship
forced me to almost wake up and turn on those emotions.
And so September, October, and like even into November of last
(37:45):
year, I remember I woke up everyday and I cried.
I remember I started grieving mymom who had passed away three
years prior that I had never really grieved before.
And I feel like I started processing all of these emotions
and I think as maybe a survival instinct of everything I was
(38:07):
going through before, I had justturned that all off.
And for whatever reason, maybe the intensity or the feelings
that I felt over the summer and having that come to an end, it
just allowed me for the first time to open up.
And so it was like 3 months of grieving my past life, grieving
lost parents, grieving all of the person I was before,
(38:30):
grieving the past version of myself that I went through.
And that's when I really intensely got into therapy.
That's when I started journalingevery single day.
That's when I went to any and every spiritual advisor or tarot
card reader or anything like silly that I thought I wanted to
try. And that's when I felt like the
(38:51):
most transformation happened. And I just after that point kind
of decided I was going to completely change my life.
And I've always been motivated and worked hard and fitness
oriented. But then when I got into kind of
January 2025, so we're in June now.
So it's been a few months. I, I thought what would happen
(39:12):
if I put my all into everything I'm doing right now and try to
live my fullest life. And that's what I've been doing
in the last five months and my entire life has transformed.
But I had to go through that grieving period.
It just was, I mean it was like 8-9 months delayed, 10 months
delayed if not more. Thank you for for sharing that,
(39:36):
that story. And I think a lot of people can
resonate with that, you know, a smaller scale for me.
But even this, you know, the AGMwe had last week, I didn't
grieve much about like the fund and this whole thing I built and
I walked away from. And then I saw a lot of those
photos and I was like, fuck, like, what did I do?
I wanted to be there and it was a really weird, weird process.
(39:58):
And it's, it's funny how these seemingly smaller events can
trigger some really deep feelings if you, if you don't
process them and you don't create that space.
You, you talked about sort of turning off your emotions.
And, you know, I used to say oneof my superpowers was my ability
(40:21):
to compartmentalize, which turnsout I don't think it's a
superpower. It can get you.
To be very productive, but when you suppress feelings for me,
it's going to just come out in other ways, you know, whether
that's, you know, drinking too much or, you know, having a
(40:43):
panic attack for seemingly no reason.
You're like, why, why is this happening and you just haven't
processed this. Do you think you've you've
gotten better at kind of turningthat emotional nozzle back on
and, and why do you think you turned it off in the first
place? That's a great question.
I think that I have for the mostpart most my life have had that
(41:10):
turned off. I I remember feeling a lot of
pride that there was like 5 or 6years.
I never cried like I was not a crier.
I didn't feel much and I think then going through it was like a
period of time where I lost a lot of people.
My my dad died and then shortly after I had two grandparents die
(41:35):
and then my mom died and then I was living in Canada and I think
it was just too much and I just completely kind of shut down.
And then I think, I don't think I really even realized that I, I
didn't have that emotional part of myself anymore.
(41:58):
And I, I think back to last summer and like going through
again, like so funny. Like I can call off a six year
really meaningful relationship, but like 2 months with someone
who I kind of liked. Could, you know, force me into
this awakening where I started processing emotions probably
(42:19):
from years and years and years that that I had suppressed.
And, and now I think like, I can't even imagine how I would
turn that back off again becauseit's just so now present in my
life. And I think like when I start to
(42:39):
feel that way, instead of like swallowing that or bottling that
back up, I just like, I like letmyself start to feel those
feelings and, you know, tell myself that that's all right.
But I definitely feel like for the longest time, I felt like it
was like weak to cry or, you know, I couldn't have these
(43:00):
emotions, which I think that's not really the case anymore.
And I think finally allowing allof that to come out, especially
with losing both my parents in ashort amount of time, like I
think that I, I have, you know, accelerated my happiness so much
by finally, you know, releasing so much of that that trauma that
I was carrying. And I think that my superpower,
(43:27):
which I didn't really realize until recently, is this ability
to alchemize my pain into progress.
And now that I also feel that pain, and I'm not just bottling
it up, that progress is accelerating even more quickly
than I ever did before. I want to just acknowledge, you
(43:49):
know, and, and I appreciate you for, for sharing that.
That is incredibly intense. I could not imagine losing 2
parents in a, in a short period of time.
Do you feel comfortable going a little bit deeper there?
Yeah, sure. Thank you.
I feel like we're getting to this age now.
(44:12):
I guess people of all ages will listen to this.
But but you and I, you obviouslywent through it before.
Many people have to, but I thinka lot of us are dealing with
aging parents illness. You know, we can see that
they're not going to be around forever.
Do you have any sort of advice for people who may have lost
(44:38):
their parents recently or maybe they're they're still around?
What would you say to kind of both of those camps?
Great question. I always tell my friends like
you got to call, call your parents, spend time with them.
I mean, really, especially if you kind of live far away, if
you think about, you know, they're, if you're going home
(45:00):
once or twice a year and you know, your parents are older,
like that might mean you only see them 10 or 20 more times.
Like if you really do the math on it, if you don't live near
your parents and you live far away.
So it's just really important I think to, I think spend that
time and making sure that you talk to them more.
Because after I think it's the thing that you miss and maybe
(45:25):
regret the most because they'll be something that happens or an
event that happens and you just want to call them or you go to
call them. You forget and it's just
devastating and heartbreaking. And you know, there's been so
many times that I've been going through things.
I mean, I've completely transformed my life.
Like I, I don't even think I look the same.
(45:47):
And I think about like when things are really hard, like you
just you just like want to call and talk to your mom and, and
you just, you can't do that. And so it becomes really hard.
And so I think, you know, I wishI had spent more time.
I wish I had taken more photos. I wish that I had more videos,
(46:11):
like watching videos of my mom. Like, it's sad.
That brings me so much peace. Like recording little things are
so important. And so just making sure that
you're making those memories. And I have friends that really
struggle with their parents. And I'm not going to discount
that. Like, I've definitely struggled
with both my parents my whole life.
We had our ups and downs, but just making sure that you
(46:33):
continue, even sometimes if it'suncomfortable to maintain that
relationship and spend time withthem like I wish I had, even
when we weren't getting along. And then just like pure advice.
If you have recently lost a parent, I think, you know, I was
so fortunate to be at Salesforce.
(46:55):
I was at Salesforce for almost adecade and they had a lot of
really great benefits. And they gave me a month off of
bereavement after my mom died. And I took it.
And so I really, you know, took some time for myself.
And so many people I know, you know, they take two or three
days and then they just go back to work and they throw
themselves into it. But if you can take some time,
(47:17):
even if you're not quite to the point where you're feeling or
grieving it yet, like go spend some time or do something with
yourself, it's just so important.
Great advice and thanks for for diving into those, you know,
hard, hard conversations. And again, I, I appreciate the,
(47:37):
the bravery of, of sharing that.But shifting kind of gears a
little bit, you know, I have to give you just a massive Congrats
for just this life you've built.You know, like you're now VP at
incredibly hot company publicly listed.
(48:00):
You're down in Miami. Seems you know, you're you're
taking your mental and physical health so seriously and you're
now the chapter of Pavilion downthere.
So you're bringing people together, you're building
community. Talk me through, I guess like
the other side, because that's the point of this podcast too.
(48:21):
It's not just like, oh fuck, crazy shit happens in life.
It's like, no, you can go through incredibly painful
experiences and still go on to build a beautiful, aligned,
healthy life. Yeah, I can't believe my life is
my life. No, I really.
You built it so. I know I, I did really hard
(48:41):
things. So much gratitude.
Like I love where I live and I love my job.
I love my boss, like so important.
And even like the friends that Isurrounded myself with down
here, like they, they're doing similar things, they have the
same goals. They are focused on growth and
building. And so it's just so fun, but I,
(49:05):
I really feel like it's been thelast like 7 or 8 months.
So maybe about a year after the big change where things started
building momentum. Someone said to me recently,
like where you are right now is the results of the effort that
you started to put in like 3 to 6 months ago.
And so I'm starting to look around and everything is
starting to click into alignment.
(49:26):
And it's, it's been really exciting.
And I, I've gotten, I've been very fortunate actually through
GTM fun that I met someone in Miami who introduced me to his
girlfriend who has become one ofmy best friends and another
woman who he invited to a pavilion happy hour and she's
become one of my best friends. And we're coach after heads of
pavilion. And so I'm surrounded with
(49:48):
people that are obsessed with running and obsessed with
building and love community and want to live a happier lifestyle
or healthier and happier lifestyle.
And it's just been so rewarding,but also a lot of it is been,
you know, not spending time doing things or with people that
no longer serve me and just realizing that my most valuable
(50:09):
resource is time. And I don't spend my time doing
anything I don't want to do anymore, which has been huge.
And also like, you know, I've been really focused on goal
setting and I was on a differentpodcast and I talked about this,
but I had, you know, I've had this really intense running
schedule. And I remember there's a friend
(50:30):
that was trying to get me to like blow off a long run to go
to brunch. And it was like almost a no
brainer. I was like, I'm not going to be
friends with this person anymorebecause I don't want to align
myself with people that aren't supportive or encouraging of me
to like hit these goals that arereally hard.
I like that that that part of reinvention can be can be tough
(50:53):
of like letting go some of thoserelationships that that don't
serve you because I think there is a lot of fear too.
I think we hold on to unhealthy relationships sometimes for the
same reason that you described about your romantic
relationship. Be like, oh, am I going to be
able to make new friends now? Like I'm older?
How do people even make friends anymore?
(51:14):
And, and how did you approach that?
Like you built a whole new circle of people in a short
period of time. And I'm sure there's people
listening to this that that feels like a daunting task,
especially in this like more digital world.
Walk me through kind of the the process of building a brand new
(51:36):
community around you. Well, I'm very lucky.
I'm still very close with my friends like San Francisco
friends and London friends and New York friends.
And so I've definitely had to prioritize like a system, the
true Rev OPS person, a system about making sure that I'm
frequently reaching out and keeping the relationship warm
tell. Me the system I need this.
(51:57):
I need this system spreadsheets.But I think like whenever you're
try, I think people think like, OK, I need to go out and make
new friends. Like how am I going to do that?
Where should I go? What's the easiest path to do
that? But I think what I did was what
do I want to do? What makes me happy?
How do I want to spend my time? And then by spending my time
(52:20):
where and how I want to spend it, you meet people that are
spending their time similar to you.
And so it's funny like a lot of my friends are in tech, which
it, I've always had friends thatwere in tech, but it's funny,
like so much of my network down here is from the tech community.
And then I would say I've started making a lot new friends
(52:40):
through running. And it's funny like run clubs
are a big thing down here. So that used to be like
recreational sports or people goplay kickball or stop or
whatever. Like there's a lot of running
clubs and track clubs. We go to a track and I started
going to this track club, it's called the Flamingo Run Club and
it's at 4:40 AM on Wednesdays and we go and you we run like 5
(53:04):
and a half, 6 miles of like interval before like even the
track lights come up. And there's like amazing people
through that. I've met a lot of people from
through my gym. And so it's, it's funny, it's
like, OK, if I live in alignmentand I spend my time doing the
things that I'm that I already want to do and I'm open and I'm
willing to have conversations with anybody.
(53:25):
All of a sudden you start surrounding yourself with people
that are very like minded to you.
And if you get really good with your discipline and build in a
routine, next thing you know, you're seeing the same people
when you're in your routine. And next thing you know, you're
surrounded by people that like to do the things that you like
to do. And they're actually this
(53:46):
incredibly positive and, you know, influence in your life.
To so you've mentioned a lot of different like practices that
you've incorporated into your life in this new.
So 1 of it is like surrounding yourself from, with people who
are aligned with the version of you that you want to live.
(54:08):
You mentioned, you know, going to therapy, running these like
really tactical things, cold plunging is, is part of your
routine. Anything else that you've
incorporated? You mentioned journaling.
Anything else you've incorporated that has had a big
impact on kind of your overall mental health and awareness?
(54:28):
I think before I never prioritize sleep.
It wasn't something I thought about as being the most
important thing. And I think sleep has become
probably the the number one thing that I think about what in
terms of my mental health, I bought an 8 sleep and it's
amazing and I love it. And it's like temperature
(54:50):
controlled and it gets really cold in the night.
So I don't wake up anymore. And that has been huge And
through like the eight sleep through, you know, all of the
tracking. I wear an aura ring.
I'm obnoxious. I have an Apple Watch.
I've got all the wearables. I think being really in tune to,
am I getting enough sleep? It does that, you know, do I
(55:10):
wake up and I feel refreshed andmentally strong.
It gives me, you know, the capacity I need to go do all
these things like sleep has become really important.
And then what's funny is becauseI'm prioritizing sleep, I've
definitely deprioritized alcoholbecause if I drink, then I sleep
terribly. And then of course, the running
in that practice. So I think, you know, the amount
(55:31):
of alcohol I drink is so much less than it's ever been in my
entire life before. And so I think sleep has
actually become such a positive influence in my life.
It allows you to say no a lot more.
So there's a lot of good podcasts on on Sleep and I
listen to all of them. I'm a terrible sleeper and it's
(55:53):
not that like I don't try like I'm I'm in bed for 8 hours a
day, but I'm I'm just terrible at it.
Is there anything and I know theimportance of it, like I'm sold
sleep. I'm sold.
I just can't shut off my brain. I think is the is the issue.
Do you, what was your process like for integrating sleep and
(56:18):
making it a priority? Do you have like a nightly
routine? Yeah, I I would say my, my
morning routine is much more dialed into than my night
routine. I think making sure like the the
temperature control was really important.
I take Asha Gwanda probably saying that wrong magnesium and
(56:38):
I try to not take any work callsafter 8 because if I'm getting
into bed by 9 or 930, like if I'm on the the phone with anyone
I work with past eight, my mind is racing.
So, you know, I try to sign off earlier than that.
But 8:00 PM is like a firm line and sand.
And then also, you know, going to dinners earlier or meeting
(57:00):
friends, you know, during like on the weekend for like brunch
instead of dinner. Like I just try not to do things
that late and and other than that, like, I mean, I, I just
watched Seinfeld in that every night.
That's hilarious this fall. Fall the Fall the Fall asleep to
(57:21):
Jerry Seinfeld. My good buddy who might actually
be editing this podcast, so Trueif you're listening is going to
laugh at that part because we were just talking 2 days ago.
He does the same thing and he's like been in relationships and
he's still just a non negotiable.
You're just going to have Jerry Seinfeld in the in the
background. Maybe.
Maybe there's something to it. 10 years at least.
(57:43):
I love that I'll have to give ita a shot and eight sleep.
If you want to sponsor this pod and send me one, I'm I'm all for
it. The and then you mentioned no
alcohol. So that's been part of my no but
limited, limited. Yeah, it's been part of my my
journey too. And it feels like a lot of
(58:04):
people are just at least re evaluating their relationship
with alcohol. Certainly the younger
generation. I think I'm on like almost day
80 of of no alcohol at all. And we'll see how how has that
been for you? Have you found it difficult or
just, you know, now that you've got these other priorities?
It's just not as exciting I guess.
(58:26):
I think it's so much easier whenI'm at home because I, I don't
need to go out. Like I like to wake up early and
you know, I like to go for my runs.
And like when I'm in Miami, I'm actually really disciplined and
like every once in a while, likeI Saturday is like my one day
that I usually take to kind of like have fun, don't think about
(58:48):
work. And I'll go on a long run and go
to the beach. And like, you know, but I would
say like it's easy when I'm at home.
I think it's really hard when I'm travelling, like being in
New York last week or, you know,in London next week.
I find when I'm on the road and I'm socializing, it's just so
(59:09):
much easier. I think as like the social
lubricant. And I think I realized,
especially as I cut back on alcohol, that I definitely have
a little bit of social anxiety that I didn't realize I ever had
before. And so when I'm going in rooms
full of people, I mean, a lot oftimes I'm one of, you know, a
(59:32):
very small group of women. Like, it is a little bit easier
when you have a glass of wine tofeel a little bit more
comfortable. But you know, especially for
work, like I'm still 1 of, you know, the only women in the room
most of the time. Is that that's still the case?
Hey, that's crazy. We've been trying to work on
that for for years. But particularly, yeah, where
(59:54):
you have kind of gone to VP level, it's still primarily men.
Do you think that is impacted how you show up to the world?
I think that it 100% right. I think that there is there is
(01:00:20):
something to be said about getting more comfortable feeling
uncomfortable. It's weird to even say like, oh,
it's uncomfortable. Like I think I used to not even
allow myself to say, oh, it's uncomfortable.
I just like, oh, I'm fine. I grew up with Big Brothers.
Like I have no problem being theonly woman in the room.
But I think as I've gotten, you know, more conscious and more in
(01:00:42):
tuned, like you definitely feel it and you, you know, you are
not always the most, you know, authentic version of yourself
because you're you're playing a part.
Like I'm really good at like playing part of the boys club
and flexing the masculine and holding my own and being bold
(01:01:03):
or, or even projecting that confidence.
But you have to dig deep And it's I can I I don't mind it.
I like it, I'm good at it, all of those things, but it takes
more energy, certainly like it it, you know, walk out of those
situations like depleted and exhausted for sure.
Yeah, I wonder if that I didn't think of that, but I wonder if
(01:01:26):
that played into part of your turning off emotions because I,
I feel like I've certainly seen in workplace environments
because wrongly women are are labeled as more emotional in a
workplace. I think many executive women
that I've worked with kind of swing the other way and like
(01:01:48):
show very, very little emotion in order to like combat that
that stereotype. Yeah, I, you know, I don't know,
I think you're definitely how you act or how you show up or
how you how you talk is I think definitely judged more.
I can't imagine it's not. I think that I have to be very
(01:02:10):
careful, like of, you know, you,you watch people all the time,
like, you know, men will get in like a fight in a meeting or
disagree. And like, if I were to do the
same thing, like, I'm sure I'd be labeled as difficult.
And that's not like just my company, that's anywhere at any
company or, you know, in my pastlives.
But I definitely think that, youknow, you feel this need to be
(01:02:32):
in control of your image at all times.
You know, you want to show up a certain way and dress a certain
way and make sure you're perceived in a certain way.
And like, there's not a lot of women at the top.
Like, I wish there was more, butthere's not.
And so I think just making sure that you play the part, like,
(01:02:53):
becomes part of it all. You know, you don't see a lot of
women in a lot of these. Yeah, well, the next generation
is going to be able to see you and near after you, which is
pretty cool. And all the stuff you're doing
with Pavilion certainly to the photos and things I see more
female representation. So I think that's really cool
(01:03:15):
that you're you're focused on that.
Well, Tessa, I want to thank you.
I know again, this is not the most comfortable thing to do on
the middle of like a Thursday. You've got to probably go to
some, some meetings and talk about ARR and lowering CAC and
marketing attribution and all that, that good stuff after a
(01:03:36):
pretty intense conversation. But I commend your bravery for
what it's worth. I'm very proud of you in your
journey. It's been it's been cool to
witness. So thank you and I'm.
Proud of you too. This is amazing.
Like I'm so excited to see whereyou go next and what you do with
this and what you're doing is soimportant and a lot of people
(01:03:57):
aren't brave enough to do this either.
So thank you for thinking of me and letting me be a part of it.
Of course. Thank you so much and to all our
listeners. We will see you all next week.
In the following interview, I sit down with Tessa Whitaker,
the VP of Rev OPS at Zoom Info and Chapter Head of Pavilion in
Miami. We talked through using
workaholism as a distraction tool and trying to process and
navigate grief in a high paced environment that never slows
down. Grief brought on from the end of
(00:24):
long term relationships and fromdeath and losing loved ones and
folks that are really really close to you.
And then we chat about checking all of those boxes that we
believe will bring us happiness,but somehow still feeling empty.
And then having the courage on the other side of that to start
(00:44):
all over and completely reinventyourself from the ground up.
And before we get into it, I do want to give a quick shout out
to our partners optimizing dot AI and Dream Fuel for bringing
this project to life. You know, most of us are heading
into a new quarter staring down the barrel of yet another big
(01:05):
quarterly target and goal for ourselves and our teams.
Dream Fuel gives leaders and their teams the tools,
practices, and mindset to achieve seemingly impossible
goals. I know it did for me personally.
Their team of elite performance coaches can give you an edge
when everyone is counting on youto win.
(01:26):
And as of now, they are giving listeners of the wake up call a
complimentary 1 to one coaching session.
Now of course they can't do thisfor everyone.
I have forever. So I would run and join the wait
list as soon as possible. And optimizing that AI gives you
the ability to finally stop guessing how your users are
(01:48):
feeling. Almost sounds like sci-fi.
But we can now use AI through a webcam to monitor vital signs,
emotions and stress levels. You can build true real time
emotional intelligence into yourdigital experiences.
You can find out more about bothof our partners in the show
notes below. Please go support them.
(02:10):
They are great teams doing greatwork and making our physical and
digital realities a better place.
This conversation you're about to listen to really hit home
with me, and I know it will resonate with many of you as
well. Please enjoy it.
(02:34):
Miss Tessa Whitaker, welcome. Hello, I'm excited to be on this
Scott. I'm excited to have you excited,
nervous. You know, these conversations
are so different. You know, I've had a podcast for
the greater part of like 6 years, but you know, really
diving into it with people, it'slike a whole other energy.
(02:58):
And hey, you never know what you're going to expect, you
know? Yeah.
I mean, I, I probably am more more nervous for having this
conversation than any podcast I've ever done.
I think back to like the very first one that I did.
And I would say this is pretty equitable to that.
(03:19):
Well, thank you for being brave enough to to come on and, and
share some of your, your story. And you have a podcast of your
own now. Like you're out there, you're
doing all these podcasts. So I'm like almost honored that
you're actually nervous for thisone.
Yeah, well, I mean, I think it'seasier to talk about Vita Visa
sometimes than it is about yourself.
(03:41):
But I've always been an open book and authenticity is one of
my top values. And so if I can share a little
bit more about my journey and maybe help people, I think it's
worth the the feeling of uncomfort.
Totally, totally. I know you know, in the past
when I've been going through it,it can feel really lonely when
(04:05):
you flip open social media, whether it's Instagram or
LinkedIn and you're just having like the worst day.
You're going through all of these things and you flip it
open and everything's up and to the right.
Everyone somehow had a Unicorn company and everyone's happy and
there's, you know, photos with their beautiful families and
(04:26):
you're like, what is what is wrong with me?
You know so. Why is everyone in the South of
France but me? Right where's?
Where's my flight to Mykonos? Yeah, and I think like, I mean,
I'm guilty of it as much as as much as anyone.
I mean, I'm posting the photos where I'm at an event or, you
(04:48):
know, my outfit and hair is perfect and I'm surrounded by
all these incredible people and I'm in different cities.
But I think that's just, you know, the highlights You're,
you're posting all of those incredible moments, but there's
so much that's in between. For sure.
And you're just actually straight off of the GTM fund
(05:11):
AGM. How was that in New York?
Great. It was great.
It's funny how so many people that you meet over the years
just truly become your real friends and like the community,
especially from GTM fund or now that I'm doing Pavilion or Zoom
info folks like they are all part of my not all, but a lot of
(05:32):
them become a part of my inner circle.
So it feels like a lot of fun and when you are in your
day-to-day life, there's a lot of people that maybe aren't
focused on the same things that you're focused on or don't care
about the same things you care about.
So when you're in a room full ofpeople that are excited about
the same things, it's just a different kind of energy that
you absorb and it's motivating and inspiring.
(05:53):
So it was a really, it was a good couple of days.
New York is exhausting. I when I'm there, I don't sleep.
It's like meeting after meeting or going to see friends and then
being in rooms full of people. And so when I get back to Miami,
it's always nice to just relax. I hear that, I spent like 2-2
(06:16):
months in New York last year andnot a good city for me.
Turns out it's a lot of fun. I just, I just don't know how
people do it. Like there's the hustle culture
in work, but it also permeates like everything, like social
life is heightened, fitness is heightened.
(06:36):
Like somehow people are working 12 hour days and then going out
and then they're at like a Berry's class at 7:00 AM.
Oh my God. I can do this for a short period
of time, but not much after that.
Yeah, I did it for, I think it was a little like maybe like 7
or 8 weeks last summer and you just don't sleep.
Like you work the 12 hour day, you do your workout, you get
(06:57):
your steps in, you go to happy hour, you go to dinner, you
repeat. There's a lot of alcohol and
it's just exhausting and you just keep doing it.
But like, I'm definitely not my best version of myself in that
environment. And it's funny because people
think about Miami as being this like, party hub and go out all
the time, which certainly there are a lot of people that do
(07:19):
that, but it's also this huge community of people that are
really focused on Wellness and biohacking and fitness and just
being the absolute, you know, most healthy version of
yourself. And so what's funny is I moved
to Miami not even realizing thatwas such a big part of the
culture or a subculture that existed here.
And I feel like I'm absolutely now the best version of myself
(07:41):
because of it. I love to hear that.
Yeah, it's been, I think that's a really good segue into talking
a little bit about your, your story and your your
transformation. You know, I've been incredibly
fortunate that you became an LP in the fund I got to meet you at
a few years back and it was kindof at this for both of us really
(08:04):
transitional phase of our our lives.
To that's so funny. No, I, I remember that retreat.
So that was right after I becamean LP and I was, you know,
flying out from Toronto. So I lived at Toronto, in
Toronto at that time, and I showed up in San Francisco and
it was three days after calling off my engagement.
(08:27):
And so I get there and I think it was even, it was the weekend
before Dreamforce. And I remember, you know,
showing up at this thing. I didn't know anybody.
And I think maybe I was still inshock of everything that I was
going through that I kind of just like introduced myself and
I was like, hi, I'm Tessa Whitaker and I work at Zoom Info
and I called off my engagement three days ago and I'm not
(08:49):
wearing a ring. And, you know, it's funny is I
think probably the reason I havesuch great friends that have
become LP's was because in that moment, like, it was straight
vulnerability. Like I was my most authentic
self. Like I had no ability, no
energy, no capacity to like havesome sort of professional shell.
(09:09):
It was what you see is what you get.
And I need so many incredible friends that I know will be
lifelong friends because of thatweekend.
But I mean, I was living a completely different life at
that time. Yeah.
So tell me a little bit about, you know, that that life like
that's super intense going through a a breakup like that.
(09:33):
And you know, for the listeners at that same time period, mine
was a little bit later, it was about 3 months.
I had the same thing, you know, happened to me.
So we kind of bonded over that and I I know the intensity of of
feelings that that come with that, but walk me through kind
(09:54):
of that that time period becauseof.
Course. The craziest part to me and and
sorry, it was like, oh shit, like nothing stops like I'm
supposed to go to work right now, like I'm what is going on?
Like I needed A at least a monthjust to like try and process
(10:14):
what was happening and like there's no space for that in
this kind of modern really fast moving world.
Yeah, no, it's just business as usual.
And you're kind of going throughthis grieving period.
Well, it's funny. So, you know, I grew up in
Michigan, and I moved out to California like a week after I
turned 18. And I went to school in Southern
(10:36):
California, went to UCLA, and then shortly after graduating, I
moved up to San Francisco. And within about a year and a
half, I fell into a tech job in San Francisco at Salesforce.
I was there for almost a decade and they moved me to London.
And so this is relevant kind of to this part of the story
because when I was in London, I met a Canadian and I always joke
(10:58):
with, you know, you Scott or Paul about, you know, my
feelings about Canada, which I'msure this Canadians listening.
So I'll be nice, but I'm still traumatized.
And I, I was there for three years and it was like the most
incredible time. Like I was in so in alignment in
London, you know, I was obsessedwith fitness.
(11:18):
I had a really great job. I traveled all the time.
And my, my ex fiance at the timeneeded to come back to North
America. And I remember saying like, I
don't want to move to Toronto. I'm not interested in living in
Canada. Like for me, where I live, it's
so important. Like it is, it is one of the
most important things to me is being in alignment.
(11:38):
Like I, I've never understood why someone wouldn't want to
live where they want a vacation because then you get to like
wake up every day and your surroundings are in alignment
with the things that you love. And so we kind of made this
agreement. We moved to New York.
So I moved to New York. I was living in West Chelsea, he
was in Toronto coming back and forth and going through this
process of getting the paperworkto move to New York.
(12:03):
And then it was March 2020 and the borders were shutting and we
kind of had to make this decision.
Salesforce was like, yeah, we'llfigure it out.
We'll get your work permit, likefeel free to go to Canada.
And next thing I know, I'm living in Toronto.
And what was meant to be a few months ended up being almost
four years. And so I was living in Toronto.
(12:26):
And, you know, I think like, youknow, the person I was engaged
with, he's a great guy. We're still friends.
We're still friendly, like he's a wonderful person.
But I think really living together for the first time,
being in the pandemic, being in Toronto, dealing with like those
winters that never ended, I was completely out of alignment with
myself. And I even look at pictures from
(12:47):
that time, like I look like a complete different person.
I have friends that say I was almost like a muted version of
myself. And, you know, I have a very
social person. I didn't really make that many
friends in Toronto, maybe like one or two.
And I just dealt with it by throwing myself into work.
And it wasn't like the healthy way that I work now, which is
(13:10):
like it gives me energy and I, Ilove it.
It was all I care about. All I think about, all I want to
do is work because that's what I, that's what I felt.
That's the only thing I felt that I had.
And I remember being there and being like, OK, if my career is
going well, then I can be happy.And then it was funny.
(13:31):
I started going down, I think, this path that a lot of people
do when they start to become successful for the first time.
And I was like, OK, if I get thecar that I've always wanted,
I'll be happy. And then I got the car.
And then it was like, all right,if I get this dog, I've always
wanted a dog, then I'll be happy.
(13:51):
I want to get a Cabapoo. And then I remember it was OK if
I buy a house South of Queen in the Beaches and I can walk on
the boardwalk every day. Like I couldn't do that in any
other city. Like if I do that, I'll be
happy. And I remember sitting there and
I'm like, in this house and I'vegot this dog and I've got the
fiance and I've got the ring andI've got the car and I was this
(14:17):
shell of a person and I was, I was terrified.
I didn't know what to do. I didn't know how to get out.
And I just kept thinking like, this can't be my life like that.
This can't be my life. But maybe if I make more money
and I buy more things or I, you know, I, I hired A stylist, I
got all new clothes. Like I was doing everything.
But it was funny. It was like, throw myself into
(14:38):
work to distract myself and thenmaybe buy these things and maybe
I'll be happy. And it's just none of it was
working. And I, I didn't realize it even
myself. Like I was so numb to it at that
point that it took two friends visiting that summer.
So this would have been, you know, a month or two before I
(14:59):
met you. Scott and my first friend came
to visit from the UK and we wentout to dinner and she said, I
think you, I think you've got a leave your partner.
And it what was funny about thatis like she's very British and
very proper and British. My British friends probably
wouldn't overstepped that boundary ever before.
And I was like, wait, what are you talking about?
(15:22):
And then it was like instant I started looking around and I was
like, Oh my gosh. But it like she was the first
person and the only person that said something to me.
And then coincidentally, 2 weekslater, my other best friend from
London came to visit and we're up at a lake, we're in Muskoka,
or in Port Carling. And I say to her, you know, this
other friend said this thing andshe's like, Oh my God, thank
(15:42):
God. She's like, you're miserable.
And I was like, I am, I didn't know.
And it was funny. We finished out that week and I
was really quiet and not entirely myself.
And we dropped them off at the airport.
We went back to our house in Toronto and I was like, hey, so
think we should call this off? And it was like the most like,
(16:04):
nice and lovely conversation. Canadians are like, very, very
nice. And we didn't even fight.
We just agreed. And then, I don't know, three
days later I was on a flight to San Francisco.
Wow, wow. I mean, yeah, I'm almost,
there's so many parallels between our our journeys that
(16:27):
it's kind of like scary to, to listen to that.
And I guess also kind of beautiful because you do feel
like, oh, this is only happeningto me or something's wrong with
me. And it's interesting, you know,
as I was listening to that, I had a very, very similar
experience of like, you get in these positions where you sort
(16:51):
of like strip away your own identity or you lose yourself a
little bit. And I think that is when you
have to really be on the watch for what you're attaching your
identity to. And, you know, for me, like you,
it was success. It was the fund.
If the fund was doing well, I was doing well and nothing else,
(17:13):
you know, mattered beyond that. And then it also made every
sacrifice that I was making in my mental or physical health,
whatever it may be, it was worthit because it I would look at
this thing and make, OK, that isme.
And that's going well. So I must be OK.
And you can sort of delude yourself into doing this for
(17:36):
really long periods of time. So you're so lucky to have those
two, you know, great friends, you know, if there's someone
who's listening to this that maybe doesn't have a great
support system around them rightnow, but maybe they feel like
(17:59):
that muted version of themselves.
And I think it's a really good way of, of putting it.
I think I was a a muted version of myself for about four years,
heightened in some ways that I would over almost overcompensate
in some of the other areas of mypersonality, but certainly muted
in like who I actually believe II am.
(18:19):
What would you say to that person or what would you say to
Tessa before your friends, you know, came and and acted as a
mirror for you? Oh.
My gosh, what a great question. I think like it sounds so cliche
or cheesy, but it's just, it's, it's never too late to start
(18:43):
over. And I think about I was so
afraid that I would be too old to ever meet anyone again or
like, I can't imagine dating someone or you know, or want
someone wanting to date me. I was 32.
I'm like 4 years old. I mean, I'm 36 now and, and I
(19:08):
remember because I, you know, I had those thoughts over time and
I was, and so it was just this fear of like, I'm too old to
start over. And now from when I started
having those thoughts to now, like I feel so young and I
actually feel younger now than Idid then because I'm living a
more authentic life. But I think the thing even
(19:33):
outside of that, I would tell myself is when you start
negotiating with yourself in your head, that means you're not
listening to your gut. And like, I spent a lot of time
negotiating with myself and or trying to convince myself that
the feelings that I was having weren't valid.
(19:55):
But really, that was that was mygut, that was my inner self
telling me that it was time to make a change, but I wasn't
ready to hear it. And so I have this big thing
that I think about all the time because I don't negotiate with
(20:15):
myself anymore. And that can be when I'm
negotiating with myself about a relationship or negotiating with
myself about a job or the big one would just be like a
day-to-day negotiating with myself of like, if you don't
work out now, you can work out later.
Like I just don't have those conversations anymore.
I just do what I want to do in that moment and not try to talk
(20:41):
myself out of something because it'll be hard.
It's interesting that you you bring that up.
It's very, very coby of you, this, this mentality, but it's
something I've been, I've been thinking about, like I have more
kind of free time now. And you know, I'm thinking about
where I want to spend it. And I'm really focused on health
(21:01):
and Wellness and, and spirituality.
But if you know, I'm honest withmyself, I'm still pretty fucking
burnt out and my nervous system is pretty shot.
And, and so, you know, I, I havethese negotiations with myself
all the time and coming from theworld of sales and BC what's
frustrating is I'm a pretty damngood negotiator, including with
(21:24):
myself. And so that is something I'm
trying to, to integrate more, talk me through that, that
mentality. So let's say you have a really
hard decision to make. You have a tough conversation at
work or it's 6:00 AM. You don't want to go to that
class. Like what is the process?
Because you're human. You're going to have this little
(21:45):
voice in your head when you don't want to do something.
Walk me through the the process in your mind because I think
it's something I need to learn right now.
Sure, I think that I've gotten better with it through cold
plunging, which sounds like so like tech founder, like cold
pledges solve everything. But no, this practice of like
(22:06):
you go in and you instantly haveto get centered and focus and
clear your mind. It's it's really practicing
mindfulness. And so the thing, it's like when
I that alarm goes off at 5:30 and I'm getting out of bed and I
have to go for a run. So I'm training for a marathon
right now. I'm running New York in
November. Congrats.
(22:27):
Thank you. I don't well.
Congratulate you after. And I don't want to go on that
run. And I'm like starting to go
through, OK, well, if I don't run now, I can run later.
And I start to identify that negotiate negotiation that's
starting to happen. It's like, I'm just going to
practice mindfulness and quit thinking about it and just get
(22:50):
really present and just keep moving forward.
So like, I'm not going to think about when I, like, I'm not
going to even entertain a conversation with myself.
I'm just going to keep putting 1foot in front of the other and
stop thinking about what I'm about to do until I'm out front
and starting the run. And it's funny, I, it like
(23:10):
reminds me so much of like the first time I've gone skydiving.
The first time I went skydiving,I've gone twice and it was, you
know, me getting in a plane, I'mlike, I'm not thinking about
what I'm about to do. I'm like scooching forward in
the plane. I'm like, I'm not thinking about
what I'm about to do. Like just not allowing myself to
even think about what was next. Just continuing to go forward
(23:32):
until like you're hanging out ofthe plane and you're, you're
like, OK, well, actually I'm doing this and I think about
just not allowing yourself to even think about an alternative.
And it's just like being presentand moving forward.
I like that I there's this quoteand I'll probably say it way too
much on this podcast, but I really like it and it's the
(23:55):
quote is discipline is the highest form of self love.
And I really, really resonate with that because you're, you're
basically sacrificing your, you're now for a better version
that your, your future self getsto live.
So like what a beautiful thing to do.
And I would say making that harddecision going back to kind of,
(24:21):
we'll call it the wake up call of, of leaving your partner and
your whole life and your dog andall these things behind like
that was an act, a really deep act of self love.
And I want to like commend you for for doing that and for how
(24:44):
did you get the courage to do that.
You know, it's so funny because it's so similar to what I just
said. It was, you know, the friends
that were there. This is all within a three-week
period. And it was, we dropped them at
the airport and then an hour later I did it.
It was almost like I made the decision and I didn't allow
(25:09):
myself to think about all the things that were going to happen
next. I was just moving forward to
what I knew was the next step. And I think sometimes, so often
people think of, OK, I know I need to do this thing, but that
this, I have to figure this out.I have to figure this out.
I have to figure this out, and the truth is, is you don't need
(25:31):
to figure out absolutely everything if you're going to
make a decision to change your life.
You just have to make the decision to change your life and
then figure it out as you go. Do you think you've got better
over the years and through this transformation of like trusting
your gut? Yes.
(25:52):
I mean, I still, I feel like I still get tested.
There's certainly been things inthe last year where I definitely
was ignoring my gut, but I, I think now I listen to it even
more. The more that you lean in and
you make decisions based on yourgut that are in alignment with
(26:15):
who you are and your values or, or who you want to be, the
easier it gets. And if we're honest with
ourselves, I think we know when we're out of that alignment.
And I almost think of it as likethis heightened consciousness
that through making really hard decisions that were in alignment
with truly who I am, you know, I've raised my consciousness
(26:39):
quite a bit. But of course, there's still
things where I'll, I'll do something or, or ignore myself
and then I can feel it. And then maybe eventually I get
to the point where I make the right decision and then I'll be
looking back and I'll be like, I, I knew, I knew exactly what I
was doing and I was completely out of alignment and I was
ignoring, ignoring my gut. But I think following your gut
(27:03):
really it's just following, you know, being in alignment is so
important. And I think a lot of people live
out of alignment. And when you're in, when you are
in alignment, like work doesn't burn me out anymore.
It gives me energy because I, I love what I'm doing.
And not only am I doing things, you know, with my job during the
day, but then outside of work, Ido a lot of things that are
(27:26):
considered work. But it doesn't feel that way
because I'm being pulled. I'm not pushing because I'm in
alignment. That alignment is such a crucial
piece and I definitely don't want listeners of this podcast
to walk away with like ambition is bad or like, you know, don't
don't go do hard things. Like that is not the message I'm
(27:48):
I'm trying to push at all. It's more exactly what you said.
Like if you can find your alignment, your true calling,
your purpose, your why, all of you know, these cliche things
like the activities are going tofill your cup.
They're not going to to drain it.
And you talked about raising consciousness has would you
(28:09):
consider yourself like a a spiritual person, a religious
person? Has that played an aspect into
this, this growth you've had? Yeah.
I I would say I probably am morespiritual, but I wouldn't label
myself as anything. The last year and a half, I've
spent a lot of time trying to understand myself, you know,
(28:34):
reading like every book there isaround attachment theory or, you
know, going to therapy consistently for the very first
time to, you know, like having crazy conversations with
spiritual advisors and soul readers in Tulum.
Like I've tried it all, but justreally trying to figure out how
(29:01):
I live the most authentic version of myself and that I
wake up every day excited to be doing what I'm doing because I
never want to feel like I'm not waking up every day living the
life that I want to live again. And I lived that life and I was
miserable. And so, you know, I think
getting to know myself better has been so important, that
(29:25):
journey, but there's still so much that I need to figure out,
but I have no idea what to do. So things are going really well
at work. And I, you know, I think like my
ambition is fueling me. It's pulling me.
I'm excited right now. Like it is not burning me out.
And I work way more now than I even did then, but it's all the
(29:46):
things that I want to be doing and thinking about.
And so it's really exciting in terms of dating or anything
else. Like I have no idea what to do
there, how to figure that out. But the work stuff is great and,
and being healthy and, you know,living in Miami and being in the
(30:06):
sun every day, training for a marathon, you know, cool plunge,
sauna practice. There's so much that that is
going really great. But I designed the life that I
wanted and surrounded myself with the people that are really
filling the cup. I love, I love to hear that.
And I think, you know, when you go down this path of like
(30:30):
alignment, you know, you talk about still figuring it out.
Like I don't think that path, there is no end goal, there is
no outcome. You know, we're, we're all going
to be figuring it out hopefully deep into our, our 90s and
staying curious and exploring new things.
You mentioned therapy. That's been a big part of kind
of my, my growth. I think I fired like 6
(30:53):
therapists at one point. I had like a spiritual teacher,
a therapist and like a performance coach going because
I was losing my mind. How, how has your experience
with therapy been going for the first time in your 30s?
Because it reminds me of what you said earlier.
It's like it's, it's never too late.
(31:14):
And I think there's people that write off therapy simply because
it's never been part of their life.
So they're like, oh, I'm good. Like I've always dealt with
stuff. Why do I need to do this thing?
That's such a great question. So I think people feel, and I
guess maybe I'm projecting, I felt that starting therapy would
be too hard because there was somuch context like, Oh my gosh,
(31:35):
like, how am I going to fill, you know, fill in this woman or
man with 36 years of my life? And there's no way that they can
help me unless they have every single detail of everything I've
been through forever. And I just don't think that's
right. And in fact, when you start
(31:56):
going, you realize quickly that like certainly they'll be themes
that you bring up or, or certainthings that you talk about, but
it doesn't have to be in order of every year and everything
that you've ever done to get to this point.
It can really just be what you're working through in that
moment or that week or that month that they can really help
(32:17):
you get through by asking you questions that make you look
within yourself or even challenge how you're thinking
about something that you're not capable of challenging yourself.
And so just getting started. Yeah, I would urge everyone to
to get started if it's not part of your practice.
(32:37):
And yeah, I'm, I'm with you on this idea.
I think that's part of why I've drawn to traveling so much.
So like, if you meet a new therapist, let's say they're
meeting the Tessa, that is that person, you know, you, you want
to explain all this context, butthey don't really like care.
You can dive into that later. They're seeing you for you and
(32:59):
where you're at in that moment. And similar when you're meeting
new people on the road, it's kind of like this brand new
mirror that shows you who you are in that present moment,
which can be incredibly powerful.
I'm like, oh, maybe I have made some headway or, oh, shit, that
that's not how I wanted to show up.
Maybe I haven't made some headway.
(33:21):
So yeah, that's, that's big. OK, I want to.
Yeah, go ahead. I was going to say something
that you said about how people that meet you where you are or
where you are now, they are seeing who you are, you know, as
you become like who you, not whoyou were five years ago or 10
years ago. And you know, I've, I've moved
(33:43):
quite a bit every three or four years.
And I'm so fortunate that I've made a lot of friends every time
I've moved. But it is funny how people that
have known you before almost hold you to a standard of who
you were before. And they're not always
comfortable with that change or that growth.
And that's been something that'sbeen very interesting for me to
to witness. Yeah, I've seen it first hand.
(34:06):
One of my really, really dear friends party pretty hard when
he was younger, I guess we all did.
But he, you know, especially did.
And, you know, he grew out of that phase, became, did a ton of
work on himself. He's the best guy ever, but a
lot of people would mirror that person back to him.
(34:29):
And so it was almost like a selffulfilling prophecy because this
is how all the people saw him. So sometimes when he was out, he
would like just go into that character again.
And it it took him changing his environment to fully flourish
and now he's like killing it andmuch more kind of aligned.
But it is interesting. You kind of have to help people
(34:54):
update their software of you, You know, it's like, here's
here's who I'm trying to be. This is like the new vision.
And sometimes that's even a conversation, you know it, that
you can't just expect everyone to, you know, catch up with all
these things that that you're doing.
Yeah. I agree.
OK. So I want to go maybe to an
(35:15):
uncomfortable period, which and and this is maybe projecting,
but you make this huge decision.You know, you build this life
that you thought you always wanted.
You get it. You realize this is not the
thing you walk away when that big moment happens.
(35:36):
I know for me when my breakup happened, also leaving, you
know, the fun stepping down. There's this moment where you
get a bunch of chemicals in yourbrain and you're so excited and
you're like, I, this is like, this is new and this is
exciting. And then there's kind of this
valley that comes and it's filled with self doubt.
(35:59):
Oh my God, what did I do? Why did I do this?
You start like very much a grieving process of this old
life and this old identity. And it can be really, really
painful. Is that something that you went
through as you were rebuilding? It's funny.
(36:21):
So initially no. But when I, I went through the,
the process, moving to Miami from Toronto, getting the condo,
starting, you know, this new life in Miami, I was living my
absolute best life. And I remember I never even
(36:42):
cried. Like there was no emotion.
I was so relieved. I was so excited.
I just was moving fast and really eager to see what kind of
life that I would build. I was just so excited to be
moving forward. And it was funny as I had this
really short relationship last summer.
(37:03):
I mean, it must have been, I don't know, 10 weeks long, maybe
last 8 weeks, and it ended pretty badly.
And I remember after that, like it was the most devastated that
I have ever been. But of course, it wasn't, you
know, about that breakup. It was that for whatever reason
(37:25):
that I had turned this faucet off on having any emotion and
going through this kind of shortbut fun and intense relationship
forced me to almost wake up and turn on those emotions.
And so September, October, and like even into November of last
(37:45):
year, I remember I woke up everyday and I cried.
I remember I started grieving mymom who had passed away three
years prior that I had never really grieved before.
And I feel like I started processing all of these emotions
and I think as maybe a survival instinct of everything I was
(38:07):
going through before, I had justturned that all off.
And for whatever reason, maybe the intensity or the feelings
that I felt over the summer and having that come to an end, it
just allowed me for the first time to open up.
And so it was like 3 months of grieving my past life, grieving
lost parents, grieving all of the person I was before,
(38:30):
grieving the past version of myself that I went through.
And that's when I really intensely got into therapy.
That's when I started journalingevery single day.
That's when I went to any and every spiritual advisor or tarot
card reader or anything like silly that I thought I wanted to
try. And that's when I felt like the
(38:51):
most transformation happened. And I just after that point kind
of decided I was going to completely change my life.
And I've always been motivated and worked hard and fitness
oriented. But then when I got into kind of
January 2025, so we're in June now.
So it's been a few months. I, I thought what would happen
(39:12):
if I put my all into everything I'm doing right now and try to
live my fullest life. And that's what I've been doing
in the last five months and my entire life has transformed.
But I had to go through that grieving period.
It just was, I mean it was like 8-9 months delayed, 10 months
delayed if not more. Thank you for for sharing that,
(39:36):
that story. And I think a lot of people can
resonate with that, you know, a smaller scale for me.
But even this, you know, the AGMwe had last week, I didn't
grieve much about like the fund and this whole thing I built and
I walked away from. And then I saw a lot of those
photos and I was like, fuck, like, what did I do?
I wanted to be there and it was a really weird, weird process.
(39:58):
And it's, it's funny how these seemingly smaller events can
trigger some really deep feelings if you, if you don't
process them and you don't create that space.
You, you talked about sort of turning off your emotions.
And, you know, I used to say oneof my superpowers was my ability
(40:21):
to compartmentalize, which turnsout I don't think it's a
superpower. It can get you.
To be very productive, but when you suppress feelings for me,
it's going to just come out in other ways, you know, whether
that's, you know, drinking too much or, you know, having a
(40:43):
panic attack for seemingly no reason.
You're like, why, why is this happening and you just haven't
processed this. Do you think you've you've
gotten better at kind of turningthat emotional nozzle back on
and, and why do you think you turned it off in the first
place? That's a great question.
I think that I have for the mostpart most my life have had that
(41:10):
turned off. I I remember feeling a lot of
pride that there was like 5 or 6years.
I never cried like I was not a crier.
I didn't feel much and I think then going through it was like a
period of time where I lost a lot of people.
My my dad died and then shortly after I had two grandparents die
(41:35):
and then my mom died and then I was living in Canada and I think
it was just too much and I just completely kind of shut down.
And then I think, I don't think I really even realized that I, I
didn't have that emotional part of myself anymore.
(41:58):
And I, I think back to last summer and like going through
again, like so funny. Like I can call off a six year
really meaningful relationship, but like 2 months with someone
who I kind of liked. Could, you know, force me into
this awakening where I started processing emotions probably
(42:19):
from years and years and years that that I had suppressed.
And, and now I think like, I can't even imagine how I would
turn that back off again becauseit's just so now present in my
life. And I think like when I start to
(42:39):
feel that way, instead of like swallowing that or bottling that
back up, I just like, I like letmyself start to feel those
feelings and, you know, tell myself that that's all right.
But I definitely feel like for the longest time, I felt like it
was like weak to cry or, you know, I couldn't have these
(43:00):
emotions, which I think that's not really the case anymore.
And I think finally allowing allof that to come out, especially
with losing both my parents in ashort amount of time, like I
think that I, I have, you know, accelerated my happiness so much
by finally, you know, releasing so much of that that trauma that
I was carrying. And I think that my superpower,
(43:27):
which I didn't really realize until recently, is this ability
to alchemize my pain into progress.
And now that I also feel that pain, and I'm not just bottling
it up, that progress is accelerating even more quickly
than I ever did before. I want to just acknowledge, you
(43:49):
know, and, and I appreciate you for, for sharing that.
That is incredibly intense. I could not imagine losing 2
parents in a, in a short period of time.
Do you feel comfortable going a little bit deeper there?
Yeah, sure. Thank you.
I feel like we're getting to this age now.
(44:12):
I guess people of all ages will listen to this.
But but you and I, you obviouslywent through it before.
Many people have to, but I thinka lot of us are dealing with
aging parents illness. You know, we can see that
they're not going to be around forever.
Do you have any sort of advice for people who may have lost
(44:38):
their parents recently or maybe they're they're still around?
What would you say to kind of both of those camps?
Great question. I always tell my friends like
you got to call, call your parents, spend time with them.
I mean, really, especially if you kind of live far away, if
you think about, you know, they're, if you're going home
(45:00):
once or twice a year and you know, your parents are older,
like that might mean you only see them 10 or 20 more times.
Like if you really do the math on it, if you don't live near
your parents and you live far away.
So it's just really important I think to, I think spend that
time and making sure that you talk to them more.
Because after I think it's the thing that you miss and maybe
(45:25):
regret the most because they'll be something that happens or an
event that happens and you just want to call them or you go to
call them. You forget and it's just
devastating and heartbreaking. And you know, there's been so
many times that I've been going through things.
I mean, I've completely transformed my life.
Like I, I don't even think I look the same.
(45:47):
And I think about like when things are really hard, like you
just you just like want to call and talk to your mom and, and
you just, you can't do that. And so it becomes really hard.
And so I think, you know, I wishI had spent more time.
I wish I had taken more photos. I wish that I had more videos,
(46:11):
like watching videos of my mom. Like, it's sad.
That brings me so much peace. Like recording little things are
so important. And so just making sure that
you're making those memories. And I have friends that really
struggle with their parents. And I'm not going to discount
that. Like, I've definitely struggled
with both my parents my whole life.
We had our ups and downs, but just making sure that you
(46:33):
continue, even sometimes if it'suncomfortable to maintain that
relationship and spend time withthem like I wish I had, even
when we weren't getting along. And then just like pure advice.
If you have recently lost a parent, I think, you know, I was
so fortunate to be at Salesforce.
(46:55):
I was at Salesforce for almost adecade and they had a lot of
really great benefits. And they gave me a month off of
bereavement after my mom died. And I took it.
And so I really, you know, took some time for myself.
And so many people I know, you know, they take two or three
days and then they just go back to work and they throw
themselves into it. But if you can take some time,
(47:17):
even if you're not quite to the point where you're feeling or
grieving it yet, like go spend some time or do something with
yourself, it's just so important.
Great advice and thanks for for diving into those, you know,
hard, hard conversations. And again, I, I appreciate the,
(47:37):
the bravery of, of sharing that.But shifting kind of gears a
little bit, you know, I have to give you just a massive Congrats
for just this life you've built.You know, like you're now VP at
incredibly hot company publicly listed.
(48:00):
You're down in Miami. Seems you know, you're you're
taking your mental and physical health so seriously and you're
now the chapter of Pavilion downthere.
So you're bringing people together, you're building
community. Talk me through, I guess like
the other side, because that's the point of this podcast too.
(48:21):
It's not just like, oh fuck, crazy shit happens in life.
It's like, no, you can go through incredibly painful
experiences and still go on to build a beautiful, aligned,
healthy life. Yeah, I can't believe my life is
my life. No, I really.
You built it so. I know I, I did really hard
(48:41):
things. So much gratitude.
Like I love where I live and I love my job.
I love my boss, like so important.
And even like the friends that Isurrounded myself with down
here, like they, they're doing similar things, they have the
same goals. They are focused on growth and
building. And so it's just so fun, but I,
(49:05):
I really feel like it's been thelast like 7 or 8 months.
So maybe about a year after the big change where things started
building momentum. Someone said to me recently,
like where you are right now is the results of the effort that
you started to put in like 3 to 6 months ago.
And so I'm starting to look around and everything is
starting to click into alignment.
(49:26):
And it's, it's been really exciting.
And I, I've gotten, I've been very fortunate actually through
GTM fun that I met someone in Miami who introduced me to his
girlfriend who has become one ofmy best friends and another
woman who he invited to a pavilion happy hour and she's
become one of my best friends. And we're coach after heads of
pavilion. And so I'm surrounded with
(49:48):
people that are obsessed with running and obsessed with
building and love community and want to live a happier lifestyle
or healthier and happier lifestyle.
And it's just been so rewarding,but also a lot of it is been,
you know, not spending time doing things or with people that
no longer serve me and just realizing that my most valuable
(50:09):
resource is time. And I don't spend my time doing
anything I don't want to do anymore, which has been huge.
And also like, you know, I've been really focused on goal
setting and I was on a differentpodcast and I talked about this,
but I had, you know, I've had this really intense running
schedule. And I remember there's a friend
(50:30):
that was trying to get me to like blow off a long run to go
to brunch. And it was like almost a no
brainer. I was like, I'm not going to be
friends with this person anymorebecause I don't want to align
myself with people that aren't supportive or encouraging of me
to like hit these goals that arereally hard.
I like that that that part of reinvention can be can be tough
(50:53):
of like letting go some of thoserelationships that that don't
serve you because I think there is a lot of fear too.
I think we hold on to unhealthy relationships sometimes for the
same reason that you described about your romantic
relationship. Be like, oh, am I going to be
able to make new friends now? Like I'm older?
How do people even make friends anymore?
(51:14):
And, and how did you approach that?
Like you built a whole new circle of people in a short
period of time. And I'm sure there's people
listening to this that that feels like a daunting task,
especially in this like more digital world.
Walk me through kind of the the process of building a brand new
(51:36):
community around you. Well, I'm very lucky.
I'm still very close with my friends like San Francisco
friends and London friends and New York friends.
And so I've definitely had to prioritize like a system, the
true Rev OPS person, a system about making sure that I'm
frequently reaching out and keeping the relationship warm
tell. Me the system I need this.
(51:57):
I need this system spreadsheets.But I think like whenever you're
try, I think people think like, OK, I need to go out and make
new friends. Like how am I going to do that?
Where should I go? What's the easiest path to do
that? But I think what I did was what
do I want to do? What makes me happy?
How do I want to spend my time? And then by spending my time
(52:20):
where and how I want to spend it, you meet people that are
spending their time similar to you.
And so it's funny like a lot of my friends are in tech, which
it, I've always had friends thatwere in tech, but it's funny,
like so much of my network down here is from the tech community.
And then I would say I've started making a lot new friends
(52:40):
through running. And it's funny like run clubs
are a big thing down here. So that used to be like
recreational sports or people goplay kickball or stop or
whatever. Like there's a lot of running
clubs and track clubs. We go to a track and I started
going to this track club, it's called the Flamingo Run Club and
it's at 4:40 AM on Wednesdays and we go and you we run like 5
(53:04):
and a half, 6 miles of like interval before like even the
track lights come up. And there's like amazing people
through that. I've met a lot of people from
through my gym. And so it's, it's funny, it's
like, OK, if I live in alignmentand I spend my time doing the
things that I'm that I already want to do and I'm open and I'm
willing to have conversations with anybody.
(53:25):
All of a sudden you start surrounding yourself with people
that are very like minded to you.
And if you get really good with your discipline and build in a
routine, next thing you know, you're seeing the same people
when you're in your routine. And next thing you know, you're
surrounded by people that like to do the things that you like
to do. And they're actually this
(53:46):
incredibly positive and, you know, influence in your life.
To so you've mentioned a lot of different like practices that
you've incorporated into your life in this new.
So 1 of it is like surrounding yourself from, with people who
are aligned with the version of you that you want to live.
(54:08):
You mentioned, you know, going to therapy, running these like
really tactical things, cold plunging is, is part of your
routine. Anything else that you've
incorporated? You mentioned journaling.
Anything else you've incorporated that has had a big
impact on kind of your overall mental health and awareness?
(54:28):
I think before I never prioritize sleep.
It wasn't something I thought about as being the most
important thing. And I think sleep has become
probably the the number one thing that I think about what in
terms of my mental health, I bought an 8 sleep and it's
amazing and I love it. And it's like temperature
(54:50):
controlled and it gets really cold in the night.
So I don't wake up anymore. And that has been huge And
through like the eight sleep through, you know, all of the
tracking. I wear an aura ring.
I'm obnoxious. I have an Apple Watch.
I've got all the wearables. I think being really in tune to,
am I getting enough sleep? It does that, you know, do I
(55:10):
wake up and I feel refreshed andmentally strong.
It gives me, you know, the capacity I need to go do all
these things like sleep has become really important.
And then what's funny is becauseI'm prioritizing sleep, I've
definitely deprioritized alcoholbecause if I drink, then I sleep
terribly. And then of course, the running
in that practice. So I think, you know, the amount
(55:31):
of alcohol I drink is so much less than it's ever been in my
entire life before. And so I think sleep has
actually become such a positive influence in my life.
It allows you to say no a lot more.
So there's a lot of good podcasts on on Sleep and I
listen to all of them. I'm a terrible sleeper and it's
(55:53):
not that like I don't try like I'm I'm in bed for 8 hours a
day, but I'm I'm just terrible at it.
Is there anything and I know theimportance of it, like I'm sold
sleep. I'm sold.
I just can't shut off my brain. I think is the is the issue.
Do you, what was your process like for integrating sleep and
(56:18):
making it a priority? Do you have like a nightly
routine? Yeah, I I would say my, my
morning routine is much more dialed into than my night
routine. I think making sure like the the
temperature control was really important.
I take Asha Gwanda probably saying that wrong magnesium and
(56:38):
I try to not take any work callsafter 8 because if I'm getting
into bed by 9 or 930, like if I'm on the the phone with anyone
I work with past eight, my mind is racing.
So, you know, I try to sign off earlier than that.
But 8:00 PM is like a firm line and sand.
And then also, you know, going to dinners earlier or meeting
(57:00):
friends, you know, during like on the weekend for like brunch
instead of dinner. Like I just try not to do things
that late and and other than that, like, I mean, I, I just
watched Seinfeld in that every night.
That's hilarious this fall. Fall the Fall the Fall asleep to
(57:21):
Jerry Seinfeld. My good buddy who might actually
be editing this podcast, so Trueif you're listening is going to
laugh at that part because we were just talking 2 days ago.
He does the same thing and he's like been in relationships and
he's still just a non negotiable.
You're just going to have Jerry Seinfeld in the in the
background. Maybe.
Maybe there's something to it. 10 years at least.
(57:43):
I love that I'll have to give ita a shot and eight sleep.
If you want to sponsor this pod and send me one, I'm I'm all for
it. The and then you mentioned no
alcohol. So that's been part of my no but
limited, limited. Yeah, it's been part of my my
journey too. And it feels like a lot of
(58:04):
people are just at least re evaluating their relationship
with alcohol. Certainly the younger
generation. I think I'm on like almost day
80 of of no alcohol at all. And we'll see how how has that
been for you? Have you found it difficult or
just, you know, now that you've got these other priorities?
It's just not as exciting I guess.
(58:26):
I think it's so much easier whenI'm at home because I, I don't
need to go out. Like I like to wake up early and
you know, I like to go for my runs.
And like when I'm in Miami, I'm actually really disciplined and
like every once in a while, likeI Saturday is like my one day
that I usually take to kind of like have fun, don't think about
(58:48):
work. And I'll go on a long run and go
to the beach. And like, you know, but I would
say like it's easy when I'm at home.
I think it's really hard when I'm travelling, like being in
New York last week or, you know,in London next week.
I find when I'm on the road and I'm socializing, it's just so
(59:09):
much easier. I think as like the social
lubricant. And I think I realized,
especially as I cut back on alcohol, that I definitely have
a little bit of social anxiety that I didn't realize I ever had
before. And so when I'm going in rooms
full of people, I mean, a lot oftimes I'm one of, you know, a
(59:32):
very small group of women. Like, it is a little bit easier
when you have a glass of wine tofeel a little bit more
comfortable. But you know, especially for
work, like I'm still 1 of, you know, the only women in the room
most of the time. Is that that's still the case?
Hey, that's crazy. We've been trying to work on
that for for years. But particularly, yeah, where
(59:54):
you have kind of gone to VP level, it's still primarily men.
Do you think that is impacted how you show up to the world?
I think that it 100% right. I think that there is there is
(01:00:20):
something to be said about getting more comfortable feeling
uncomfortable. It's weird to even say like, oh,
it's uncomfortable. Like I think I used to not even
allow myself to say, oh, it's uncomfortable.
I just like, oh, I'm fine. I grew up with Big Brothers.
Like I have no problem being theonly woman in the room.
But I think as I've gotten, you know, more conscious and more in
(01:00:42):
tuned, like you definitely feel it and you, you know, you are
not always the most, you know, authentic version of yourself
because you're you're playing a part.
Like I'm really good at like playing part of the boys club
and flexing the masculine and holding my own and being bold
(01:01:03):
or, or even projecting that confidence.
But you have to dig deep And it's I can I I don't mind it.
I like it, I'm good at it, all of those things, but it takes
more energy, certainly like it it, you know, walk out of those
situations like depleted and exhausted for sure.
Yeah, I wonder if that I didn't think of that, but I wonder if
(01:01:26):
that played into part of your turning off emotions because I,
I feel like I've certainly seen in workplace environments
because wrongly women are are labeled as more emotional in a
workplace. I think many executive women
that I've worked with kind of swing the other way and like
(01:01:48):
show very, very little emotion in order to like combat that
that stereotype. Yeah, I, you know, I don't know,
I think you're definitely how you act or how you show up or
how you how you talk is I think definitely judged more.
I can't imagine it's not. I think that I have to be very
(01:02:10):
careful, like of, you know, you,you watch people all the time,
like, you know, men will get in like a fight in a meeting or
disagree. And like, if I were to do the
same thing, like, I'm sure I'd be labeled as difficult.
And that's not like just my company, that's anywhere at any
company or, you know, in my pastlives.
But I definitely think that, youknow, you feel this need to be
(01:02:32):
in control of your image at all times.
You know, you want to show up a certain way and dress a certain
way and make sure you're perceived in a certain way.
And like, there's not a lot of women at the top.
Like, I wish there was more, butthere's not.
And so I think just making sure that you play the part, like,
(01:02:53):
becomes part of it all. You know, you don't see a lot of
women in a lot of these. Yeah, well, the next generation
is going to be able to see you and near after you, which is
pretty cool. And all the stuff you're doing
with Pavilion certainly to the photos and things I see more
female representation. So I think that's really cool
(01:03:15):
that you're you're focused on that.
Well, Tessa, I want to thank you.
I know again, this is not the most comfortable thing to do on
the middle of like a Thursday. You've got to probably go to
some, some meetings and talk about ARR and lowering CAC and
marketing attribution and all that, that good stuff after a
(01:03:36):
pretty intense conversation. But I commend your bravery for
what it's worth. I'm very proud of you in your
journey. It's been it's been cool to
witness. So thank you and I'm.
Proud of you too. This is amazing.
Like I'm so excited to see whereyou go next and what you do with
this and what you're doing is soimportant and a lot of people
(01:03:57):
aren't brave enough to do this either.
So thank you for thinking of me and letting me be a part of it.
Of course. Thank you so much and to all our
listeners. We will see you all next week.
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