#10: The Founder's Dilemma with Diane Jones: Insurance tech Industry Leader

In this episode, we dive deep into the world of the Super Unemployable with Diane Jones from InsurTech. We explore the challenges faced by founders who sell their companies and find it difficult to adjust to being employees again, often leaving money on the table. Diane shares her personal journey of selling her family insurance business and her subsequent experiences working for a larger conglomerate.

We discuss the concept of job autonomy and what it means to Diane, as well as her transition from being an entrepreneur to working within a structured organization. Diane opens up about her struggles with micromanagement, the loss of creative control, and how she eventually found her way back to a role that aligns with her values and need for flexibility.

Diane also touches on her current role at a tech firm, her thoughts on future entrepreneurial ventures, and the legacy she hopes to leave for her children.

Whether you're an entrepreneur, a professional seeking autonomy, or someone navigating career transitions, this episode offers valuable perspectives on embracing the Super Unemployable life.

 

Show notes:

Approximately 40% of startup founders leave their companies before completing their buyout or reaching an initial public offering (IPO). This is often due to various reasons, including differences in vision with new owners, personal choices, or simply because the founders are no longer the right fit for the company as it scales under new leadership​(

Knowledge at Wharton Kruze Consulting

 

Additionally, around 33% of employees, including founders, tend to leave within the first year of a company's acquisition, often due to organizational mismatches or cultural differences with the acquiring company​(

MIT Sloan

Episode Transcript

(00:00):
40% of founders who sell their company to someone else leave before the buyout terms are complete.
That means that they often leave money on the table, stock, options,
all kinds of perks, because they simply cannot survive as the employable.

(00:24):
I think once you've had a taste of the super unemployable life,
it is very, very hard to go back.
And of course, when another company buys you, they have a different vision.
They have a different direction.
There's other places that they want to go with the company, and it doesn't necessarily
jive with the way that you originally saw that company progressing,
but you've handed them the keys and they,

(00:46):
for whatever reason, have decided to keep you on or require you you to stay on,
whether that be to avoid having you join the competition or to not lose your
knowledge base in that very crucial transitionary period.
But founders walk away. And that is exactly the experience that our next guest,

(01:08):
Diane Jones from InsureTech had when she and her family sold their insurance
company to a larger conglomerate.
Diane Jones joins me on the podcast today, and we talk about all kinds of topics.
But the one that we probably didn't explore enough was that period in her life

(01:31):
whereby she was asked to stay on with another company after they had sold their
entrepreneurial venture.
And I remember speaking to her and saying, you're not going to make it a year.
And I can't remember. I think I was fairly close on that estimate,
but we'll dive deeper that into that in this podcast.
I'm very excited to bring to you today, Diane Jones.

(01:54):
So just as a preamble, I do all the pre-recording like your intro and an outro later.
Okay. It's based on the conversation that we have and no editing.
So if you screw up, just keep talking.
There's, I don't do a single piece of edit on a
program there's no point and just

(02:15):
have fun with it and feel free to ask questions engage like it's your hour so
that's the funny thing is i was i was talking to the producer of our podcast
earlier and i was like oh man you know how much editing you have to do for me
so this is going to be interesting when i don't get edited we'll find out yeah all right.
What does the term super unemployable mean to you? So it's funny because I'm

(02:40):
saying this as somebody who works for somebody right now.
I'm, you know, I've always classified myself to be super unemployable.
And I was told at an early age, I will never be able to work for anybody.
Yet I'm perfectly content and happy with my role right now working for somebody.
So I feel like it's not necessarily the fact that you aren't employable, but it's this,

(03:02):
entrepreneurial spirit that you have within that makes you want to guide your
own career, have the autonomy to gauge how your career is going,
your role is going, be able to make changes, be fluid.
You're not micromanaged.
You have your values aligned with the organization, whether it be your own or

(03:24):
somebody else's, the direction it's taking, and that you really believe in it.
I feel like I have worked at organizations
where I didn't feel the same alignment, and I shut right down.
The second I'm not feeling like I'm helping move that needle or having a sense

(03:45):
in what's happening, it doesn't work.
So super unemployable to me might be different than some people because I have
now been in all different aspects, running my own company working for somebody
that was horrible and then working for somebody that I really respect and I see.
I see some, some similarities in all of them, but, but yeah,
definitely just having that flexibility and having your own job autonomy.

(04:09):
Yeah. You mentioned autonomy a couple of times. What does that mean to you?
I think autonomy is a, a self-defined word, but what do you,
where does that, how does that relate for you?
For me, it's, for me, it's like, I don't want to be, I don't want to be a cog
in a machine. I want to know everything about the machine and I want to be able

(04:31):
to dictate where I fit and what I do and also how I balance my own life.
I have never been able to just, you know, walk into a company and be like,
I clock in at this time, I clock out at that time and you tell me what I do in those hours.
I want to be able to dig deep and dictate what I can do, but also jump out when I need to.

(04:53):
I want to have balance for my life. I want to have balance for my family.
And I see job autonomy as everything that's outside of a paycheck you receive
twice a month, everything that guides my day.
If I wake up and if I'm feeling passionate about what I'm doing,
if I'm, if I'm growing in a way that's somewhere different than just I'm getting

(05:17):
paid, then that to me is job autonomy.
It's interesting. So going way back, have you ever been fired from a job?
I'm not sure if I even know this. Have you ever been fired?
Yeah. So tell us about that first. Cause I think that's the first taste.
I think we all go into our first jobs and we're excited and we think I'm going to be so great at this.

(05:39):
Yeah. And for some people, it doesn't work out that way.
Yeah, yeah, I'm trying to think. So I can think of one instance that I've been
fired, there might be others, but one sticks out.
And it's where I, I mean, I'm not good at just having leaders or managers that
demand respect just due to their title or position.

(06:02):
And if they're, if they treat people below them as subordinates,
and just like people that just have to say yes to everything they say,
I don't react well. So my one time being fired, I worked at World Health Club,
and I was the receptionist.
And it was something so little as not aligning with the manager that worked
there who treated the staff as his own little kicking bags.

(06:26):
And one individual at the company was he treated her poorly,
and I, for some reason, always feel the need to jump in.
So i told him how
i felt about it i'm not you know if if respect
is deserved i am right there i respect is
earned and you know i can definitely work for somebody who i respect i don't

(06:48):
just give respect blindly for somebody who is in a position of power or power
that they deem they have so yeah i got canned you got canned so you got canned
for standing up for another team member yeah okay Okay.
That happens. I've heard of that happening many times.
Not one of the many reasons I've been fired for, but, but it,

(07:09):
so then you also mentioned that you were told that you were not employable. Yes.
Where did that come from? Who, who told you that? A professor.
And I wish I could remember his name, but so I took, I don't know if you remember,
I took a minor in entrepreneurship and enterprise development at UFC.

(07:30):
Yeah. We had a class together.
Yeah, that's right. I think we did other things other than the classwork, but yeah.
Yeah, that's, but so we, I did, I was in this one course and we were supposed
to, we were supposed to build an enterprise that we would have loved if we had
no, you know, no blocks, no financial blockades.
What would I have created as a company at that time?

(07:52):
And I, and I was in this course with this professor and I don't even remember
the context that it came up, but he pointed me out in the class and he goes,
you will never be able able to work for somebody.
And at first, the way he said it, I thought, oh my gosh, is he insulting me?
And then I turned it around and go, no, I'm okay with that.
He views me as somebody who needs to be the boss, not work for somebody.

(08:16):
And again, I don't take it as a negative for working for somebody or not working
for somebody. I see pros and cons to both.
But yeah, after I I kind of changed the way I heard that in my head.
I realized, yeah, he's right.
Yeah, I probably will just need to run my own show at some point.
And I actually remember, do you remember when I, my company got purchased and

(08:39):
I went to go work for the purchasing company and you told me,
yeah, I give you a year or two tops. You're not, you're not doing it.
Yeah. I remember having that conversation. And then I remember having the conversation
that followed that said, yeah, I quit. I left. Couldn't do it. It's very common.
Founders that get bought out oftentimes for there to be a larger package,

(09:00):
the company wants you to stick around for obvious reasons. reasons,
but the number of founders who make it, I can't remember what the percentage is.
I'll, I'll link to it in the show notes because I know that there are studies
out there, but I think it's more than 50% do not make it the entire term.
And we actually have guests coming up, Alan Albert, who sold to Apple and he
didn't make it and he didn't make it in his, in, in the terms.

(09:23):
And he can tell the story better than I can, but very common.
And so let's go back. So you, you worked for a few different companies.
I remember, I think at one time you worked at the tanning salon and then,
you know, we worked at Jacob together and you worked at a fitness club,
all the kinds of things that you do when you're in high school,
right? You work odd jobs.
Then it was shortly after high school that you joined the family business, right?

(09:46):
Well, actually, the very first family business you joined was the coffee shop
that your mom purchased. Yeah. Yeah.
So tell us, walk us through that. You've been in a couple of family businesses
starting at what, 16 or something? Well, I think we were in grade 12.
So yeah, 17, 18. I call that my mom's midlife crisis. And she's going to listen

(10:09):
to this and she'll agree.
She got burnt out in her insurance career and decided to buy a coffee shop.
And while that was a financial drain, and I mean, definitely different than
what she was used to in the corporate world, it was the ignition that made it
possible to start the next venture, which was the big success.

(10:30):
So we had coffee and cake, which was a dive. And I think we had it for like eight months.
It was phenomenal for a group of grade 12 students who needed a place to hang
out. So it was wonderful for us and our friends.
But for my family- Some of the best times. I was just talking about that a couple of days ago.

(10:53):
I remember driving down McLeod trail. This is in Calgary and looking to see
if anybody's car was parked out back.
And if they were, you'd quickly spin around and we'd go have a party at coffee and cake.
Cause it closed it, I don't know, eight or nine or something.
And then that was our time where we would go and drink and play music and eat the sandwiches.

(11:13):
And I don't know if I ever paid for any
of those i probably owe a tab at coffee and cake
that's long outstanding i'm not sure if anybody stew probably
paid more friends probably yeah that's probably
why our financials didn't work out so well because
we literally used it as our hangout and ate and drank all of the supplies so

(11:34):
you know what it's the equivalent it's the equivalent of that 70s show basement
that was coffee and cake for what you see right and we had the dirty couches and And yeah, yeah.
I mean, great memories. I loved it.
And it gave my mom the reset she needed.
So after getting rid of that place, we graduated from high school in what you

(11:59):
graduate in June and Silvercrest Insurance started December of that year.
So what happened was I applied to university.
For the computer engineering program, and I got declined. And I remember thinking,
well, what am I going to do? I have no other backup plan. That was it.
And my mom said, I'm going to start a brokerage. You want to do it with me?

(12:21):
I was like, all right, fine. I got nothing else to do until I get into engineering.
So Silvercrest Insurance started in their house.
We used the spare bedroom in my parents' house at the time.
We stayed in our pajamas, watched soap operas. was very, very low-key starting,
very little tech, very little resources.

(12:45):
We started with zero clients, so it was really ground up.
And we just enjoyed... My mom and I have a great relationship.
We enjoyed working together.
It spanned over almost 20 years, and many people couldn't do that with their
parent or sibling or any family member.
It takes a special relationship relationship to make it that long.

(13:06):
And we worked amazing together.
Like we actually had a really great working, really. Well, you worked at Silvercrest for three months.
I did. Yeah. I was a summer fill in. Yeah. Yeah. I work in the reception desk.
Yeah. I was not very good at it. I remember I should, that would have been a
job I would have been fired from for sure if I didn't know the owners.

(13:27):
But I remember I was handwriting the outside of the letters that,
you know, you You send letters to clients.
And at one point it was either you or your mom came up and said,
yeah, we're going to need you to use the label maker or the address because
your handwriting is not. You have the worst handwriting ever.
In another world, I was a doctor that would have handwriting matches that.

(13:51):
But now I decided to become an entrepreneur who gets fired a lot.
So there you go. Yeah. It Silvercrest was a really neat space.
You guys had a great office. When I joined, you had, I think there was about
five or six employees at that time.
Probably, yeah. Yeah, and we got to, I think at max, we were 13,

(14:11):
14 was the level we got to, which was a great, you know, we ran the company for 18 years.
It was super successful. I loved every minute of it. And I actually,
when we sold Silvercrest, I had an idea of what the next step was going to be.
But I think I was very misaligned with how that was going to work.

(14:36):
I thought it was going to be an elevation of Silvercrest within this other company.
It was going to take us to a next level because we were going to be,
you know, part of this bigger organization and they were going to have all these resources.
And I just, I saw, I saw an evolution of it.
And I saw us going to the next stages. And what actually happened was we got

(14:59):
bought by a company that was just very archaic and.
You know, far behind where we were in a lot of ways and had no interest in changing that.
So all of the work I had done, all of the ideas I had were just kind of squashed.
And yeah, and I just, it wasn't, it no longer made sense because I just felt

(15:21):
trapped within this very very political, micromanaged organization.
And the second I felt that way, I completely withdrew.
Your autonomy was gone. You lost that autonomy.
Work hours, as I recall, went down. So in some ways you had a lot more freedom,

(15:44):
but that wasn't your definition of autonomy.
You know what's funny? They gave me a corner office. They gave me a free car.
I had a company car, which was beautiful.
Everything I wanted to do, they were like, no, that's probably not going to happen.
So I would sit in my office and make my Christmas gifts on Shutterfly.

(16:06):
Once I shut off and I was done, I was done. I went on seven trips in a year.
I was like, well, if you're not going to let me do anything,
I'm not going to do anything, if that's how this is going to roll out.
But I just couldn't. I was not mentally engaged in it.
I wasn't growing. I wasn't learning. I wasn't being challenged.
My days were just dragging on and it was not, you know. In the end,

(16:31):
though, one thing is I didn't quit. They asked me politely to leave.
That helps with the buyout, doesn't it? Yeah. It's usually in a contract if
you quit, you lose something.
Oh, I remember thinking like, yeah. Yeah.
I remember thinking like they, they're going to like, I am not giving in to the quitting.
I will, I will be. So you were like George Costanza when he walls himself in

(16:55):
that office in the Seinfeld episode, because he's not quitting.
They hired him under the false pretenses.
We're dating ourselves here with the Seinfeld reference, but.
We're old. There's no secret. It's so it's fascinating.
If we go back, you mentioned not getting into the engineering program and have,
I know that I didn't get into the business program three times trying.

(17:19):
It was my fourth go that I finally got in, but in a way, not getting into a
program is almost like getting fired.
Isn't it? You have a direction that you're meant to take, or you think you're
meant to take somebody takes that away or by your own circumstances,
you don't achieve it and you end up down a different path.

(17:40):
And I think that's really a, that's that fork in the road moment that a lot of people face.
And my curiosity is, is that what makes somebody more super unemployable when
they look at the fork in the road and they go, well, I'll do something for myself then.
Or is that an inevitable outcome? I don't really know.
I only know my own path, which is every time that I'm faced with a fork,

(18:04):
I go down the route of, let's do it yourself and just make it that much more
complicated and difficult. But was that your experience as well?
You know, it's interesting because I feel like when I was told no,
when I remember the letter, I actually, I have a horrendous memory,
but I do remember that letter holding it in my hand. I mean,

(18:24):
like you were not accepted.
And I have always been the smart kid.
I was always, you know, in the advanced classes, I was always the nerdy kid. That was my thing.
I was going to engineering. When I got the no, it was like, what do you mean no?
What do you mean you're not letting me in? I'm the smart one.

(18:45):
And I feel like I wallowed for a little bit, but then I almost get to the point
where I'm like, no, no, you're not telling me that I'm not doing this.
Like I get very defensive, but like most defiant of people telling me that I'm
not going to get what I want.

(19:06):
So doing you know switching gears and just
finding a new path became my mission you know
I just said oh I'll help my mom out I'll just help
her on this venture that she wants to do but I tried
to find other ways to get in so that's when I went to the Mount Royal College
at the time path and did the university transfer program into engineering so

(19:27):
I'm like well if they're not gonna let me in the front door I'm gonna find a
way to get in on the side and I'm gonna you know make it my mission because
I'm just not good at being told no.
And that's, there's this concept of committing to a losing cause, right?
We are so invested and committed to something that even if it's the wrong decision,
we will pursue it anyway for the sake of pursuing it. Yeah.

(19:50):
Do you feel as though you committed to a losing cause or was getting that engineering
degree something that really became valuable to you in your long term?
That's a funny question because I actually, it took me eight years to get the
degree. And within those eight years, I did it part time.
There were many times I'm like, I don't like this anymore. I am.
I'm really not going to be a computer engineer. And I under,

(20:13):
you know, I very quickly realized I was not suited to be a computer engineer in the end.
But I had told myself that I was going to do it. So come hell or high water,
I was finishing that degree.
And and then everyone laughed at me because I
went in insurance for 20 years after that and didn't use
my engineering degree but now I

(20:35):
look at it and I'm in a tech firm that does insurance so it's
kind of a great blend I'm using both of things but yeah for the bit of the time
I was almost like determined to get it just because I had said I would do it
not because I wanted it not because it was like my desired path because I had
decided I was going to do it I got into it, so I was going to do it.

(20:57):
So do you feel as though the current company that you're with,
you wouldn't have been able to get the position if you didn't have that degree?
Yeah. Yeah. It's when I was going back into the workforce after being off for
two and a half years, I honestly had zero idea what I was going to do because
I had only had success running my own company.

(21:20):
I had just spent two and a half years away from working.
I mean, it was through COVID. It was, and I had just come off of a bad experience
prior to that where working for somebody did not work out well.
So I went in going, I'm not sure what I'm suited for.
I don't know what I would excel at. I don't know what I want to take on,

(21:42):
but I knew I wanted to find something that I was passionate about and something
that would make it worth leaving my children,
make it worth not being at home with my kids, which I also learned I was not suited for.
I'm not a stay-at-home mom And it goes both ways.

(22:04):
I think we've gotten so wrapped up with what people should be doing and not
enough wrapped up with what are people meant to be doing.
Exactly. There are some women I know that are phenomenal stay-at-home moms.
They thrive in it. They do fantastic things with their kids and they,
you know, they excel in that. I don't.
And that's okay too. I have three children and I love them, but I also like

(22:27):
having, you know, my work.
I like using my brain in different ways. it's just the way I'm wired.
So I knew I wanted two and a half years being at home and I needed to figure out my next thing.
And I met with somebody that I had known in my past because he had owned a brokerage
and he now had this tech company where I was actually a client of way back when.

(22:51):
And we just met for lunch and he was like, could you come work for us?
And I was like, doing what?
What would I be doing? He's like, I don't know, but let's find something. then.
And so I didn't apply. And I just told him, I said, I have a seven month old at home.
Find me something that brings me passion, and I will say yes.

(23:12):
Find me something that gives me both sides of my brain, and I've always used that.
You know, I've got my insurance side is one side. My analytical computer side is the other.
Find me something that will spark both ends, and I can thrive in,
but really be passionate when I wake up every morning to do it.
Because I will not, you know, put my kids in daycare to drudge to an office that I hate.

(23:36):
So and it's been great you know
the education thing so now without
that degree you think you still wouldn't have had this it sounds
like you would have got the job anyway he came to you looking for a
fit your degree wasn't the reason that he came to
you but i don't know the the fit is that
i have that computer background i mean yes i don't code at the company but i

(23:58):
can talk to developers and understand what they're saying you know like there's
a side of of my brain that translates between the insurance clients we have
and the technical developers that we have making the products.
And that is a block in a lot of companies, I think, not to just,
you know, like put myself up there, but like, it is a hard language barrier between the two ends.

(24:24):
Insurance people are traditionally not very tech savvy.
And the industry can be very archaic. There there are some that are excelling,
but a lot that are really stuck in their ways and don't know tech talk.
And then you get a developer and you, I mean, you've talked to engineers,
that's, that's a whole different type of person.
So being able to translate the differences and just having,

(24:47):
even though I'm not using my degree in a sense of like, I'm not building the
products, I was able to learn the way to, to communicate in code. I can, I can code.
And so when they, when I'm discussing things with the development team and the
engineers, I have that knowledge.
I have the ability to understand what they're saying and can kind of be the bridge.

(25:10):
Yeah. I, Mike, see, the thing is I battle when I think about how to advise my children,
right it's you you mentioned
eight years of part-time work and i ask myself
as an entrepreneur and and anybody what
could you do with eight years of part-time work so that's four
years full-time work cumulative what could have been done with that time that

(25:33):
might have progressed further i don't know and it's a question that obviously
comes up a lot more now that we talk about ai and our ability to have access
to information and even a teacher on your phone who can teach you literally anything.
I'm learning AI and Python and all these things that I would never have touched before.
I just coded a WordPress app because I worked with AI to do it.

(25:56):
And I knew just enough to be dangerous, but not enough to actually code it myself.
And so what would you tell your children as they become, what is the value of
a degree to your children?
It's interesting because I love education. Like I actually am very pro-education.
I've always loved school. I love books.

(26:18):
I love learning. You know, if I could go back and get another degree at some
point, that's probably going to happen.
But I don't think the actual subject matter or the, you know,
the pure education piece is all you gain from it.
I think there's so much that comes out of being in school.
Like, yes, eight years I did part-time school,

(26:42):
but I balanced that with working downtown full-time and rushing to the university
on lunch breaks in a suit and being that weird kid who, you know,
peeled in just in time for class and didn't go to the parties in the dorms because
I was, you know, going back to my office and,
or I was there on the weekends or like I did it very unfraditionally and I learned

(27:02):
so much more than just the content.
I learned, you know, life balance, which I wasn't capable of achieving.
I just learned that I could try to do it. I learned how to, you know, manage my time.
I learned that I was, I learned that I was capable of learning, right?
It's not even that I was able, like there were some classes in engineering that I completely bombed in.

(27:27):
And if anyone is listening to this, that was in school with me,
like I was never getting the highest grades or I wasn't top of my class,
but I was capable of learning and ingesting that information.
And I found, I find that to be super important.
I do find education in anything. So I think for my kids, I would say,

(27:47):
learn something, learn anything, always learn, never stop learning,
whether that be in a formal education.
Whether that be in a, you know, I don't know, a trade school, even travel,
travel is learning, like there's, there's different ways to learn and explore,
but just never, never stop growing and ingesting new things into your brain

(28:10):
and never stop asking, you know, why is that?
Or finding out new things. Like I find I'm always, I'm always looking into new ways to learn.
New new things to grow my brain i don't know
if that makes sense it does and it comes up a lot
actually talking to having done this podcast and the people that i've been speaking
to the one common theme that i found amongst the super unemployable is this

(28:35):
craving to learn to grow to continue to push yourself and it's not to say that
the highly employable don't always already and also have that trait,
but it's the one truly defining thing that I found so far in this journey is
that every single person I've talked to who deems themselves on super unemployable

(28:57):
or relates to the super unemployable has this thirst for knowledge that there's,
there can never be enough.
So let's talk about that. How do you, where do you get your information from?
Where are you where are you keeping up with your learnings right now i i'd read
a lot i've been you know i have six books on the go right now it's and i'm always

(29:20):
just kind of jumping in between.
Different topics or different what do
you read is it everything industry related or what's your
genre a bit of both so in my
podcast we are women in insurance and
yeah do a little name drop your podcast is called
and where can people find it yeah so the podcast is risk takers

(29:42):
and trailblazers the women in insurance podcast i'm
one of four amazing co-hosts and we have guests on that are just excelling in
the industry either in insurance or insure tech and we talk about everything
we talk about like you know exceeding in a very male-dominated industry are,

(30:04):
traditionally, the insurance is a very, very boys club. Like,
it's just, it always has been that way.
We make sure, I mean, we're not slamming men in the conversations.
We're just elevating women and working for, you know, equality and getting them
to look into how do they balance life during, you know, baby years?

(30:24):
How do you balance working and getting to that next level when you're also trying
to raise a family? How do you deal with stress and burnout?
How do you deal with your mental health when you're when you are trying to achieve new things?
How do you ask for those promotions? How do you get further in the industry? How do you.
Excel. And we talked to a ton of different guests that have achieved those things.

(30:47):
And we just, we asked them, you know, it's a, it's a very casual conversation.
I always say it's like coffee with your girlfriends or, you know, like the talk show.
I was going to say, is it like the view for the insurance industry?
Pretty much, pretty much.
But we just talk about like, how, you know, how did they do it?
What did they do? Well, what did they find successful?
And, and just mentor people coming into the industry and give them,

(31:10):
give them an avenue that,
they can watch women really, really succeed and then reach out or learn from.
So we actually are interviewing a doctor this week who focuses on resilience
and stress management and mental health.
And she goes to companies, whether in our industry or outside,

(31:34):
but works on, specifically with women, how to balance it all.
Which the imbalance is a unicorn that doesn't exist but
how to you know just how to get through
and there's just a lot of topics that we that we
dive into it's been it's been amazing so
i read a lot of books based on who we're interviewing who are or what they recommend

(31:56):
we've got guests that come on we're actually starting a risk takers book club
to talk about the different books that we've been reading to get ready for each
podcast what's the best book we've read so far.
Sorry? What's the best book you've read so far?
Oh, I'm reading The Power of Habits. Have you read that one? I haven't. No?

(32:17):
So I'm trying to, I mean, in my own world, like I just said,
balance is not achievable.
I don't believe in balance because if anyone's striving for balance,
they always are going to feel like they fail.
So I believe in, I've heard of it as like integration, you know,
work-life integration. integration, but I am constantly behind on everything.

(32:39):
I'm constantly trying to figure it out and make it look like I've got it all
figured out. But without...
Without faking it. And so I'm trying to read a bunch of those like,
you know, self-help or self-improvement or books.
I find the power of habit to be a good one that I'm reading right now.
That's like how to just make positive habits in your normal days that just get

(33:01):
you to where you want to be.
The best piece of advice I ever got was actually in Perth, Australia,
when we were asked to come over and work a bar, a very big, busy bar on the coast.
And I remember I was going like a bat out of hell trying to serve everybody.
I was sweating, just pouring sweat 30 minutes into this, like my mad rush of

(33:24):
trying to just get everybody at the bar served with the drink.
Finally, one of the managers comes over and he says, look all night long,
no matter what you do, you're going to be 30 people deep, no matter how fast you go.
And all you're going to to do is burn yourself out. Just relax.
And I took that advice and I've carried it with me because I always have 30
more projects that I could do. It doesn't matter how quick I do them.

(33:47):
And so now I'm trying to just enjoy the process and let myself check out at
the end of the day when I'm just tired and say, I'll pick it up tomorrow.
Yeah. Cause then you're going to come back. Like if you take that break,
you're going to come back refreshed and probably get it done better and faster
than if you had tried to struggle through it when you were tired and burnt out.

(34:09):
Right. So I think, you know, if you think about your entrepreneurial journey,
when you were working with your mom, building up the insurance company,
building up Silvercrest, there was a lot of life changes for you.
You graduated high school, you graduated university, you eventually went on
to get married, to have a child. There's this...

(34:30):
I fear, I think, for a lot of people when they think about a super unemployable
journey in that there's no stability, right? You never really know.
As one of my friends says, you eat what you kill. How did you manage that process?
Were there times that you found yourself scared, depressed, fearful?
What did that look like for you as you went through that 20-year journey?

(34:54):
See, it's interesting because I don't know if I ever felt that way.
I honestly, when I, so I'm going to backtrack it one step.
When I graduated from university, we were eight years into our company. So we started in 2000.
I graduated from university in 2008.

(35:14):
And I remember I took a six month period right after graduation and I weighed
out everything because I had a really big choice to make.
Do I stick with the company that I had been building with my mom for eight years
that I had grown to love and become literally like a family member?
It felt like it was so ingrained in us.

(35:36):
Or do I now take my newfound degree and go get an engineering job and look into,
you know, working for a company and totally switching gears? Become the employable.
Yeah. Yeah.
But it took me a while because I, you know, I thought, well,
this is what I worked for. This was the plan.

(35:57):
This was always the, the goal was that I was going to graduate from engineering.
I was going to go get a cushy job and that was what I was going to do.
But because I had taken that other fork and that, you know, we had decided to
make the company, which I, I literally started with, it was my mom's goal.
I was helping her. It was not, it was not a me thing. You know,

(36:18):
I was, I was 18 when we started. I made her bagels while she worked.
I went and did photocopies. Like, let's be real here.
I was the assistant for the first little while.
And in those eight years, I had become quite an integral part of the company
and it had become so important to me that I couldn't imagine leaving.

(36:39):
And I also weighed out because at that time, I was just about to to get married
and I hadn't had my first child yet.
And I thought, what am I going to do in a few years down the road when I have
a child and they have an event at school?
Am I going to be somebody who has to request time off and try to like balance?

(37:01):
Do I go to, you know, can I get the time off to be at the thing?
Do I want to take a day off to do this?
Or do I stay in the company that I had complete flexibility?
I had complete determination of what my day and my weeks and my year looks like
that I could balance being a mom in the way I wanted to, but also working my butt off.

(37:24):
And I didn't that was actually really big deciding
factor I mean yes I love the company and I decided I
wanted to stick with insurance but I wanted
that flexibility I thrive on that flexibility and I you know what even in my
even when I had lunch with my friend when he asked me to come work for the for

(37:44):
the company I'm currently with I said it at the lunch I said don't expect me
to clock in and clock out. That's not how I roll.
Like I will work when work needs to get done and I will give it my all.
And, and to that effect, I spend a lot of evenings after the kids go to bed,
catching up on work or, or, or putting in extra time because I don't work in a structured day.

(38:09):
I don't do, it just, it never has worked for me. I feel that's confining.
So it was a really big decision to stay with the insurance company after getting
that, you know, piece of paper that said I made it through those eight years
and feeling like that was the best decision for me.
And in all honesty, I felt like if it failed, if I made a bad decision, I was...

(38:36):
I had a degree that I could always fall back on. I had a lot of experience in
the insurance industry. I would go do something else. Yeah.
It's interesting because you had to go through that journey at Silvercrest to
be in a position where now you can negotiate your terms.
You have to have done the hard work. And I think a lot of people that I meet,

(38:58):
especially younger people,
there's an assumption that you can, and I don't want to be the guy that kids
these days, but there's an assumption
that you can negotiate terms without having earned your stripes.
And that I find challenging because whether you do it through your own company
or you do it through somebody else, you have to prove you have the skills,

(39:21):
the knowledge, the ability, right.
To be reliable, to be trustworthy, to, to get things over the line,
to help the company grow. Yeah.
And that's a fascinating place.
And I think there's a privileged spot that the super unemployable get whereby
if you did that time and you built something that's valuable to a lot of people, that's a currency.

(39:44):
Yeah. No, I totally agree.
And I know because I have gone through it all and because I have,
you know, done the two decades of working through it, I know my self-worth when
I go into, like when I went into that conversation.
I know what I'm bringing to the table. I know, you know, I have to be my biggest

(40:06):
cheerleader and I have to advocate for what I can bring.
And I knew that. I was just being completely honest because in,
you know, for them to get the best of me, I also need to get the best for myself.
And if I'm in an environment that really feeds into, going back to that word,

(40:28):
but my job autonomy and feeling that I have with flexibility is a big thing.
Especially as a mother that's a huge huge thing and
then I if I get that from a company or get that from
an employer I'm going to give my best
self and you're a fully remote company the
new company that you're with so I actually I'm it's hybrid so our yeah our head

(40:51):
office is in Calgary and I go in over the summer one day a week and now we're
going back to two days a week so it's kind of a nice blend of getting that time
with our colleagues and our teams and also having the days where we are at home.
Like today I'm t-shirt and jogging pants and comfy and started my day super
early because I didn't have to commute.

(41:12):
But we also, we have, most of our employees are out in Egypt.
So with the time difference, it does cause for some really early mornings and
some, you know, balancing of, of their time as well.
So yeah, Yeah, the hybrid model works amazing.
I have a theory that in about 10 years, the pendulum will swing and people will

(41:34):
be demanding to have an office to work from again.
I think the work from home will lose its flair after a little while.
If I think of the early years when I had a career, I loved going in to an office,
not for the office, for the lunch and for the after work drinks,
everything in between. I despised.
Do you think that like, do you think your viewpoints changed though,

(41:55):
since you've had a child? I could never go back into an office.
Actually. I love being at home. I love being at home at eight.
So I work on Eastern standard time, but I live in, in Vancouver.
So it's three hours difference. So my workday starts five 36 o'clock.
My daughter gets up at seven and around seven 30, she comes waltzing into the

(42:16):
office and says, hi daddy.
And then tells me about whatever dream she had or whatever in her baby garble.
And I love that. I love it so much. And for me, I could never go back to an
office environment because I find an office like a noose.
I had a great office. One of my first jobs was at Telvent Energy in Calgary,

(42:37):
and they gave me this big, beautiful office.
And I just remember just hating every minute of it. And back then,
it was because it wasn't my office.
And I thought, well, if it's not my building, then I'm just walking into somebody
else's, like you said, cog in the machine, right? Marxists. But...
But now it feels like a noose, the idea of having to go somewhere.

(43:00):
We can afford it. We could do it. Some of the people that I work with are asking
for it, but it's not something I'm ready to commit to.
The deal I actually made with our manager is if we do get an office,
you're just going to have to expect that I won't be there and you would have to manage morale.

(43:20):
It's just you know the
way my brain works i just do better outside in
a way yeah so for my super unemployable journey
i could never even go back to working
directly for somebody who has
rules and restrictions around that because it just wouldn't work but
maybe it'll change i don't know i do miss after work drinks

(43:42):
and that is one of the best parts
about having an office right is the camaraderie and
and a lot of people are not getting that see and it's funny
because that's the only piece i don't have i go downtown
once or twice a week but i
book it out of there at four o'clock because there's three kiddos so there's

(44:03):
daycare pickups or school pickups or homework or dinner and even even with two
parents we're outnumbered there's just too much so it's a And I hate driving.
I hate the commute. That is probably my least favorite thing.
If I could just teleport to the office, I would be super, super happy.

(44:23):
But I've been trying to get into podcasts that can keep me entertained while
I'm driving so I don't get road rage.
Stage but trying to deal with you know
dropping kids off and getting somewhere it's
it that's my biggest stress i don't mind being at the office i don't
mind the balance of a couple days here a couple days there i just wish i didn't

(44:46):
have to drive that's all yeah that's the the self-driving cars i cannot wait
until those arrive there's a million other things i'd rather do a car is a a
rather productive space i i used to uber until we got a car finally because we have a kid,
But in the Uber days, it was a 30-minute ride where I could just get stuff done.

(45:07):
I loved it. Loved it. And podcasts.
The funny thing is, is yesterday, I literally said to my boss,
I'm like, all right, I'm done.
I'm putting in a request for a driver. I need the company to buy me a driver
because I'm in this box for 40 minutes each way.
And I feel like I could do better things with my time.
So I got denied. So that's an interest that you mentioned driver and people

(45:30):
as they become more successful in their career can afford things like a personal driver, right?
Private Jet, the CEO of Starbucks, who was just hired is commuting.
I don't know if you've heard of that article via private jet from his home down
in Newport, California, up to Seattle.
But he gets to write his own terms.

(45:52):
Hey, the rich get to write their own rules, right?
There's a rule for the rest of us and there's a rule for the rich.
But on that note, don't we want to become part of that class of rich?
Now, again, I've spoken to a lot of entrepreneurs who money is not their definition
of success and wealth is just a small measure of what they're trying to accomplish.

(46:14):
I think in my journey, I've always said to myself, I've got a billion dollar
idea in me. I've just got to get it out.
So I know where my definition of success lies. Where does it lie for you?
Do you feel in your current role now, unlike in Silvercrest where growth was
at your fingertips, right now you've got a whole company deciding the growth

(46:36):
trajectory and you're now a smaller piece of that.
Where do you see yourself fitting in and how long does that last for?
So that's an interesting question because we do talk about this quite a bit
because our company is in what's always been in a little influx where it's rapidly changing.
I've been now in the company for three years and it's going from a small, small little tech firm.

(47:04):
And every day it feels like we're just blowing up to this next level.
So there's so much change. And I do honestly feel like I have a voice in where
it's going and some of the decisions.
And if I wasn't able to provide that, it wouldn't have worked.
I need to feel like I am part of the path and where we're going.

(47:26):
But I do, I say this, you know, consistently to, to Sharif, our CEO,
and I will, you know, he will agree that I'd say this, but I said,
I'm like, you know, I believe in the company, I will do what I can to make this
company as successful as possible. But I am not doing it.
As a martyr, I expect to be insanely wealthy and very successful.

(47:51):
And I'm only here because I see that happening with this company.
So, you know, we've got very lofty goals and PrivateJet is one of them.
So we're just working because I see that potential.
I do see that happening until it gets potentially bought by somebody.
And then we're, you know, it's an employee owned company.

(48:14):
I'm a shareholder. So success for the company is always inevitably going to
be success for me as well.
And then I go find a new adventure. chair. And then I go figure out what happens next.
I find that to be exciting rather than nerve-wracking.
I think a lot of people, when layoffs are coming through their company or deciding

(48:37):
what to do or what's happening,
I think a lot of people go to worry and nerves where I look at it as, what can I do next?
What's the next path I get to take? And maybe that's Maybe that's not a great
way to look at it as somebody who has a mortgage and has mouths to feed,
but I never worry that I'm going to not be successful.

(48:58):
I just have that ingrained in my head.
Do you have a seat at the table at your current company? Mm-hmm.
So you get to guide the decisions. I have many teams that report to me of growing
quite a big area under me.
And I definitely feel like we've got a very good leadership team.

(49:24):
And I'm part of that. So it's a great feeling to be a part of that company and where it's going.
So up until now, most of your entrepreneurial journey or all has been with a
partner, your mom first with the first two companies and then a company that existed.

(49:47):
Do you see yourself going out on your own? I could. Maybe.
I'm not scared of that. I do like having, you know, I guess I like working with
somebody who is aligned with me.
So if I had a partner that we butted heads on things, I would have a very hard time dealing with that.

(50:09):
It's not a great answer, but yeah, I could do it. I could. Sometimes I think
about starting things again.
You know, would I want to start another insurance brokerage? Maybe.
Know, I keep my license because I never want to close any doors.
I never want to shut any opportunities off.
So I keep in touch with the industry. I have, I'm still licensed and I kind

(50:30):
of just feel like the, it's going to sound so cheesy, but like the world is my oyster.
I can, I feel like I just do whatever. I don't know why I, I credit that to my mom, I guess.
She always told me wanted and whatever I wanted to work for,
I could do. So that's just in my brain.
So if you could start any company tomorrow, what would it be?

(50:52):
Hmm. That goes back. I go back and forth on that. You know, when I was in that
course, that was the entrepreneurship course.
I always wanted to do corporate event planning.
I don't know why. I love it. I love the thought of, would that make me insanely successful?
Probably not. But it would definitely get this other side of my brain,

(51:13):
you know, the creative piece that doesn't get always tapped into.
And I feel like that would be fun. That'd be my fun job.
So that was back in university, you had that idea. What's held you back from doing it?
Maybe just the feeling of it not being a sustainable income.

(51:33):
I definitely thrive on all of the other aspects of my job that give me the flexibility
and the balance and all those feelings.
But I also want to make a lot of money. I also want to be very successful.
I also want to be very, you know, I want to give my kids a life that just have
no, you know, no struggles or not that anyone's not going to have struggles,

(51:56):
but I want to be able to travel and I want to be able to, to live in a certain way.
And I want to be successful.
Would you carry on that same journey with your children? Work with them like
your mom did with you? Yeah.
Yeah, for sure. You've got three kids. Any standing out as the next CEO of your company?

(52:18):
It's going to be recorded. I don't want to throw any of them under the bus.
They're going to look back at this. Don't answer.
A non-answer is the right answer. Yeah. Yeah.
I have one in diapers still. I mean, really, time will tell. Okay. Okay.
What legacy do you want to leave behind, personally and professionally?

(52:40):
So when we talk about my kids, I think about, you know, what do I want them to think of their mom?
And what kind of things do they want? If somebody asks them,
what's your mom like? Or what does your mom do? do.
I want them to be so proud of me in that I'm going out there,

(53:01):
that I'm trying my hardest, that I'm doing things that make me happy and motivated.
I'm not, you know, I'm not coming home and being like, ugh, another day at the office.
You know, I want them to see a passion in me and know that, you know,
moms can go out there and do that.
Dads can go out there and do that. Anyone can go out there and do whatever they want.

(53:22):
And I want them to see that I'm doing something and I'm always striving for the next thing.
I listened to, I should have gotten this quote ready, but I listened to Chandra
Rimes do a commencement speech at a university where she said.
See a world where a land is named after their mother, because I'm out there

(53:43):
doing what makes I'm, you know, I'm, I'm giving them a happy mom because I am
fulfilling what makes me passionate.
And I, I totally misquoted that.
It's probably completely different, but it always stuck with me that the talk
that she gave about just doing whatever makes you fulfilled will give your kids the best mom possible.

(54:10):
And that looks different for everybody, right?
So I want my kids to see a mom that's just doing what makes her happy and being driven.
Like just that drive, the ambition. I want my kids to be ambitious because that's ingrained in them.
They've grown up with that and they've learned it by association, right? Right.

(54:32):
And ambition can be in any avenue.
It doesn't have to be down a path that is that is guided for them.
It doesn't have to be can be whenever ambition strikes or whatever gives them.
Yeah, I use passion a lot, I feel like, but just gives them that drive to love
what they're doing and love the the life they're making.

(54:55):
What about professionally? No, you got it. It was great. So what's your professional legacy?
Professional legacy. is I would like to, I want to be looked at as somebody
who is, you know, crushing whatever glass ceiling goes in my way.
If there is that, you know, still in my world or I want to be known as somebody who is,

(55:21):
I try very hard when I'm at work to be very empathetic and also give a lot of
care into either my clients or my employees.
Employees I want to be known as somebody who is is
successful without smashing other
people you know I want to rise up with people and bring people
with me I want to be a mentor I would love it if I could

(55:42):
mentor new people coming into the industry we've actually
heard so much positive feedback from our podcast on how
it's helping people and that makes me extremely happy
I would love to continue with that
work and and also be potentially on boards
for different you know i'm part

(56:02):
of different organizations that do charity work and just
have my hand in so many different things that
make me you know happy and just being known that i'm that i'm out there and
i'm a kind person i don't know in the industry i would love to just be known
as that somebody did it right not the wrong way mentorship comes up a lot when we chat on this podcast.

(56:29):
What is your journey right now? Where are you at in your mentorship journey?
In either receiving or giving. Either. I guess both.
Both. I think it's lifelong, isn't it? Aren't we always seeking somebody to
mentor us and eventually somebody to mentor?
But yeah, probably already happening in tandem.
Well, it's funny because we talk about it on our podcast, how you find mentorship

(56:51):
in so many different ways. Always.
People always think of mentorship as like the person who is your manager or
somebody that's above you in the company.
But you can be mentored by somebody, you know, that's aligned with you in the
company, a coworker that you just you find you find something that they do that

(57:12):
that challenges you or helps you or brings you up.
Like you can find mentorship in many different places. So, I definitely,
I mean, my mom, first and foremost, has always been my guiding mentor in everything
I have done up until this point.
And I wouldn't be in this industry without her and what she's taught me.

(57:33):
I definitely, my podcast co-hosts, we are all each other's mentors.
And we always talk about that, how we're guiding each other through everything
that we're learning right now.
And I feel like we are receiving so many messages of people saying that they
have found the podcast to be a great space for them and they feel like we're,

(57:56):
you know, an avenue for them to get mentorship from or we're linking people together.
It has been actually quite fascinating, the following we've already received.
And we've actually had a company reach out to us to say they'd like to hire
us or have our podcast as their training material for females in their industry.
It's a national company.

(58:17):
Just this little idea that we had about bringing a voice to a topic that maybe
doesn't get discussed enough and where it's going, it's been amazing.
So yeah, my thing is I just, I, I have a lot of people that report to me right
now and I try really hard to show them that I do care.
And I think in that sense, it will help. I hope it helps.

(58:41):
And I want them to know that they can always, I'm open and I'm open book.
I never, I never feel that there's
not enough to give. I feel like when we all help each other, we all,
higher. So if everyone had that thought, there wouldn't be so many political
competitiveness and all those bad things that come into offices.

(59:02):
It's a really nice thing about the podcast space, isn't it?
It's a safe space to converse, to share ideas, to mentor, to be mentored.
I've been saying that it's kind of like the cockroach in the apocalypse.
This is talk radio that's existed for over a hundred years and it just keeps

(59:24):
changing format but humans,
are still as ever engaged in this radio talk show format that and it's just
never gone away what i love about podcasts though is it's not restricted by
time just like this conversation could be a half an hour could be three hours
we we go where the conversation takes us and we get to explore are topics that,

(59:46):
like you said, other people aren't addressing.
And if it's one or two listeners who hear it and say, that's me. Oh my God, that's me.
That's all it's there for, right? It's to give that mentorship.
I mean, it really, it does go back to mentorship. Yeah. Well,
we talk a ton about imposter syndrome and do you know how many people have reached

(01:00:08):
out to us and have said like, oh, wow, I listened to your podcast and I have imposter syndrome.
I connected with that. I'm battling with that.
It just sheds a light and it lets people discuss and know they're not dealing
with stuff by their self.
It really does bring a community together.
And yeah, I love it.

(01:00:31):
One of my favorite parts about podcasts, you get to explore all the wonderful
things that you've done in your life, but you also get to explore some of the darker times.
And so when you think back about your career, and we just talked about the legacy
you want to leave behind, what do you fear most along that journey, past or future?

(01:00:51):
I think, like right when you said dark times, I instantly went to the time when
I was leaving, or when I was trying to go back into the workforce after having a break off.
Off and just the mental struggle that I went through of feeling not good enough or feeling like,

(01:01:13):
you know, two and a half years off was going to be a detriment to me looking
like an attractive candidate to go back into an office or back into a company.
I went, you know, I really...
I really shut myself down in my confidence and for just a, just,
you know, a little bit of feeling like, well, maybe nobody's going to want to hire me.

(01:01:33):
And that, I never want that to be something that, I don't know,
just the mental health of, of a lot of things, the mental health of work,
the mental health of trying to achieve balance.
And just that, the confidence feeling, I guess I, I don't want my kids to ever
feel, if we're thinking back to, to legacy, I always go right back to like,

(01:01:54):
what are my kids going to think?
And I don't want them to ever feel that way about themselves.
So I'm trying to like backtrack the coin of, okay, now as a three and four and
10 year old, how do I instill a strong enough confidence that they don't get to that point,
that they don't retreat to a dark space and think negatively of themselves.

(01:02:16):
And they go in the world and just think, you know, I'm here. I'm awesome.
Let's do this. so it's interesting what i've
gleaned out of this podcast and it's been a really interesting episode
is this interplay in your life
where you've dipped between the employable and the super unemployable and for
very clear motivations have gone to either side my prediction here now with

(01:02:40):
my magic envelope is that something will come to a head in the next five maybe
ten years with With your current company, there'll be a direction.
There'll be a conflict of pursuit.
And if your employer is listening, I hope I'm not creating conflict by saying
this. You can just tell them when to stop.

(01:03:00):
And you're going to be, again, faced with that question of employment or super unemployment.
Where do you go? And usually it's from that parting that we say to ourselves,
God, I'm never going to work for somebody ever again.
And you've already had a taste of both sides.
When you think about that future journey, do you fear that inevitable fork in the road?

(01:03:23):
Am I wrong in my prediction that that fork will appear?
No, you're not wrong, which is annoying because you usually are right.
I don't like admitting that, but no, that doesn't fear me at all.
I feel like I will take that as just a chance to make a new adventure.
It doesn't scare me in the slightest. I love it.

(01:03:45):
And what a perfect way to end this episode on the idea that when that fork appears,
if you see that as an exciting opportunity,
to me, that is one of the biggest indicators that you are super unemployable
and that you do not have to fear your future.
I think it's when I think a lot of people get paralyzed by the fear that somebody

(01:04:10):
else's decision is going to negatively impact your life and you'll be without options.
But what you see is somebody else's decision opens up options because now there's
new avenues to explore. And I think that's,
the most exciting way to live. Yeah, I agree.
So as we always do at the end of every podcast, I ask this question,

(01:04:34):
Diane, who else do you know that is super unemployable that you believe would
be the next great guest for this podcast?
You know, it's funny when going through the show notes, I actually blanked at that question.
And I was like, I need to spend some time thinking Thinking about that because
nobody, not that I don't have anybody in my, you know, in my circle,

(01:04:58):
but I have to think about that.
So, yeah, I'm going to have to circle back to you on that one.
Oh, no, this is a live podcast with no edits. We're going to wait. Oh, fantastic.
Yeah, we're going to wait. Nobody gets to defer a question on the super unemployable.
You've been presented with a fork.
You could try to delay, but then we'll just sit in silence, which is fine.

(01:05:22):
I was listening to a podcast the other day, and he was mentioning he was listening
to a Buddhist podcast where they would ask a question and ponder for two or
three minutes in silence before the next person would answer.
And he said it was just wonderful being stuck in that silence.
And I must admit, I'm very uncomfortable with silence. So maybe we should test it out right now.

(01:05:43):
All right. I got to. I got to. I got to. Oh, no. I was looking forward to the
silence. No, I'm not giving you that. Give us the best one.
Okay, I have met a fascinating...
Woman recently. And she, her name is Dr. Christy Lane.
And I will warn her that I'm shouting her out here, but she has been in so many

(01:06:07):
different, like she has started a wearable technology lab at Stanford University.
She works for a venture capitalist firm in New York. She has just started a
fascinating company called Flora, and it is a fertility insurance company,
which I am just bust, all interested in because I have had my own fertility

(01:06:31):
struggles along the way.
And I know what that can do to a woman.
She's an advisor on Trufla's board. So that's how I met her.
And she will be a speaker at our Tech Fest in Calgary in September.
And I just find her to be one of the most fascinating people ever.
So I'm going to put up my recommendation is Dr. Christy Lane. Dr.

(01:06:54):
Christy Lane, you have been called out on the Super Unemployable podcast.
And I am really fascinated to somebody who's in fertility.
Having been through our own journey, we've got one child and one on the way,
and you had three, and we've shared quite a bit of information back and forth about that.
And the one thing I realized, and I got very engaged in the pregnancy process

(01:07:17):
and, you know, fertility, obviously, all the way through to the hospital system and everything.
And what I can say is, A, the information that doctors are working off of,
and all of them are in agreement, is decades old, some of which is 60 plus years old.
The medical system is geared towards medical intervention versus prevention

(01:07:40):
and, you know, allowing the woman's body to be and do what it naturally does.
And I have never seen a system that's also the vast majority of research having
been conducted by men, which also makes no sense.
Men telling women what to do with their bodies, what else is new, right?

(01:08:01):
But I was flabbergasted in the first journey, having our first child,
watching this system completely fail.
Myself, my wife, obviously our child.
One of the things that we ended up with our midwife team talking about is how
birth is actually a negotiation with the hospital. Like-

(01:08:22):
business negotiation as to how things are going to go and what you're going
to get and what interventions they're going to take. And you literally have to negotiate.
And we did that along our journey. And had I not known that you can negotiate,
which a lot of women don't know, you end up down tracks that you didn't need to go.
This is a, for another episode, it's not quite super unemployable,

(01:08:44):
but I really want to explore it in a meaningful way.
And I And I'm so happy. I really do hope Dr. Christy Lane, I'm getting that
right, Christy Lane, does join us because hopefully we can venture down that
topic as well. But it's really near and dear to my heart.
And for anybody listening and for the people who've been through it,

(01:09:05):
just like with your employer, just like starting your own company,
just like with anything life, everything is negotiable.
And I want people to know that. And it's your life, right?
I mean, you mentioned that. Advocate for yourself. Advocate.
Advocate, advocate and do that in every aspect. You mentioned that with your current employer.
Yeah. You mentioned that with the companies that you've been involved with that were startups.

(01:09:28):
And of course, we just talked about birth and fertility, but,
but advocate. Yeah. Yeah.
Well, I'm going to send you the link for Flora, the company that she just started. It's fascinating.
And I will connect the two of you. That is fantastic.
Well, Diane, it has been an absolute pleasure having you join us.
I know you're very enthusiastic when I reached out, which I just love.

(01:09:49):
And this was a really enlightening conversation.
What I've loved so much about doing Super Unemployable is you meet people with
such vastly different views on what this world looks like. And isn't that the best part of it all?
So from the bottom of my heart, thank you so much.
And I hope that you'll come back. We're going to hope to do a big guest panel
in the future. And I hope you'll be part of that.

(01:10:11):
I would be more than happy to. Thank you so much for having me.
That was Diane Jones of InsureTech. She is also the producer and host of the
podcast, Risk Takers and Trailblazers.
My key takeaway from that conversation was that maybe I don't really know what
the super unemployable is.

(01:10:32):
In all respects, and I've known Diane for 30 years now, it's 30,
right? Yeah, about 30 years.
And I would not consider her the employable.
I think she can be very successful at being employed, but I don't know if that
is what satisfaction looks like.

(01:10:54):
That's my takeaway. And I think we all know people like that, right?
There are people in our lives and we look at them and we say,
you know, you're just not cut out to be told what to do day in and day out.
Some people enjoy it. A lot of people actually really do enjoy knowing what their job is.
They exist very well in the black and the white. I've often told people,

(01:11:17):
and I remember this from job interviews when I was trying to be gainfully employed,
I would always tell people I exist very well in the gray area.
I actually don't like getting up every day and dealing with questions that I
know the answers to. I want to be presented day in and day out with problems
that I have no idea how I'm going to solve.

(01:11:40):
And I've got to find a way to overcome those challenges and be successful.
I think that's why entrepreneurship has always been the more favorable path,
if not the more profitable path.
But I respect this other journey.
We've got many guests who are going to be coming on the show who arguably do
not consider themselves super unemployable,

(01:12:01):
some of whom have told me they They are highly employable and I look forward
to going down that road with them because the one thing as I dig deeper,
they all tell me, yes, I am highly employable. I just choose not to be.
That's kind of a fascinating concept, isn't it? I could be employed,
but I choose not to be employed.

(01:12:23):
I choose my own path. I choose my own autonomy, as Diane so eloquently defined in our talk.
I'll leave that with you. Autonomy, super unemployment, employable,
highly employable. What does it mean?
If you are highly employable, does that make you super employable?

(01:12:45):
I really don't know, but I look forward to chatting with more of you about it.
As a reminder, we are always looking for great guests. If you would like to
join the Super Unemployable podcast, please do reach out to me on LinkedIn.
You can find me at Dean Horsfield.
There aren't many of us out there, so you'll definitely be able to find me.
Or you can look us up on our website, superunemployable.com.

(01:13:05):
And until next time, we'll chat with you then.