April 30, 2025 • 46 mins
Diana Miller, a Benefits Pro 2025 Advisor of the Year finalist, shares her remarkable journey from growing up in Bogotá, Colombia to becoming one of America's top five benefits advisors through grit, analytical thinking, and cultural perspective.
• Benefits advising requires wearing multiple hats to serve employers, HR professionals, and employee populations
• An advisor's true value is revealed during challenging times when problems need solving
• Diana's "secret sauce" includes grit developed through childhood adversity, strong analytical skills, and cultural empathy
• Growing up in Bogotá during the drug cartel wars required constant security protection from armed guards
• Attended an English immersion school that prepared her for global opportunities
• Earned a scholarship to study in the US, choosing Dubuque, Iowa primarily based on weather expectations
• Experienced culture shock including a memorable incident trying to bribe a police officer
• Transitioned from marketing representative to advisor by going beyond expectations and providing strategic input
• Frustrated by seeing employees walk out of enrollment meetings due to poor benefits, sought better healthcare solutions
• Motivated by creating positive healthcare experiences for her community and designing better systems for future generations
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Transcript
Episode Transcript
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Speaker 1 (00:01):
You're listening to Risk and Resolve, and now for
your hosts, ben Conner and ToddHufford.
Welcome back to another episodeof the Risk and Resolve pod.
I'm your host, ben Conner, andtoday our special guest is
Deanna Miller, benefits Advisorat Conor Insurance and drumroll
(00:27):
2025 Advisor of the Year,finalist that's recognized by
Benefits Pro, one of the topfive advisors recognized in the
entire country.
Deanna, how are you doing today?
Speaker 2 (00:41):
Hey Ben, I'm doing well.
It's an honor to be here.
I'm very excited to be a partof the podcast, so thanks for
having me.
Speaker 1 (00:48):
Yeah Well, congrats to you on the recent recognition
of your long-term efforts iskind of how I view it.
This has been something that'sbeen on your professional bucket
list for a little bit of time,hasn't it?
Speaker 2 (01:04):
Yeah, it sure has.
It's one of those things where,you know, we kind of see all
sorts of colleagues and advisorsacross the country being
recognized for the efforts andtheir hard work, and it's one of
those things that, when Istarted in the benefits industry
, I thought you know what, oneday I'm going to be on the cover
(01:27):
of that magazine, because Ibelieve that hard work deserves
recognition.
And I'll definitely say that Ihave a pretty strong work ethic
when it comes to that.
And just seeing people like you, you know, following your, your
footsteps on that, and nowseeing my name within the
recognition, is definitely anhonor that I don't take for
(01:47):
granted.
So pretty excited to see one ofmy dreams come true.
Speaker 1 (01:51):
That's awesome and it's been fun for me to be able
to watch that occur.
So you talked about motivationand work ethic as like kind of
some of the main things.
I'm sure there are othercharacteristics that go into
play, but what's kind of thebehind the scenes of like what
does that hard work look like tobecome an advisor of the year
(02:12):
finalists?
Like what does that look likeon a day-to-day basis?
Speaker 2 (02:16):
It's an advisor role.
I feel like it's wearingmultiple hats because you do
have to tend to many differentstakeholders.
So of course, you have theemployers that you work with,
and within that employer setup,there's also different types of
parties as well.
(02:36):
I mean I have my CFOs, my CEOsand my HR professionals, who I'm
working with from a strategicperspective day in and day out
to understand their companyobjectives and help accomplish
those objectives through themanagement of the benefit
programs that they offer,partnering with us.
But in addition to that, wehave their employee population,
(02:58):
who also has very specific needs, and it is my responsibility
and I take that very seriouslyin helping our team.
So everybody who supports ourclients, including account
managers as well as membersupport individuals, understand
what sort of needs that employeepopulation has and help serve
(03:19):
those needs as best as we can.
Speaker 1 (03:22):
That's not an easy task.
Speaker 2 (03:23):
No no.
Speaker 1 (03:25):
At the same time.
Speaker 2 (03:26):
Yeah, but it's also one of those things where I feel
like the advisor is also thefirst line of defense if
something goes wrong, and so wehave to be prepared to be that
problem solver.
That can come from manydifferent aspects of a plan
again, or stakeholders withinthat employer, and so sometimes
(03:47):
too, from an advisor hard workperspective.
Advisors don't get a lot ofrecognition when it comes from
clients, because usually youknow if things are going well,
things are quiet and things arenot going well.
That's when we really hear froma specific employer and
something that's not going well,and so I do feel like the
advisor role for it to deserveor to receive recognition.
(04:09):
It doesn't happen very often,and so when it happens, you got
to take on it, but it's a lot ofhard work.
You got to wear a lot ofdifferent hats as being an
advisor.
Speaker 1 (04:19):
Yeah, I always kind of found that, or at least I
feel like I've learned over thelast many years that our clients
should actually look at inthose hard times, like when
things are like a little diceyor problems occur, like that's
when they get to find out likeif they actually hired the right
advisor, because it's easy foreveryone to look great when it's
going well, but it's like youfind out what your advisor is
(04:42):
made of and how good they are ontheir feet and how well they
think and all those sorts ofthings.
When things go wrong, whenthere's problems that occur,
yeah, you're 100 percent right.
Speaker 2 (04:52):
I feel like it is in times of pressure that a
character of a person reallycomes through the advisor, vice
versa, back and forth.
Seeing how those problems getresolved will really be a test
to you know.
Are they the right fit or arethey not the?
Speaker 1 (05:11):
right fit.
So don't they say like pressure, like obviously pressure can
crush things right, like justgeneral, like science, but also
pressure is what createsdiamonds, right?
So, there's opposite thingsthat can occur from an event
like pressure.
So what would you say?
Is your like secret sauce foryour personal craft of advising?
(05:31):
Like what is the thing thatyou're like?
You know what like thesecharacteristics to my approach
is how I accomplish what I canaccomplish with my clients on a
daily basis.
Speaker 2 (05:42):
That's a very good question.
Well, I think that a lot of mysuccess is attributed to my
personal experiences in life andhow I have been able to face,
you know, adversity, challengesand be able to come through
successfully from those.
I think one of those skills isgrit.
(06:03):
I think that's a characteristicthat, from my childhood, was
something that I always saw inmy parents, my father especially
.
He was a man of all sorts oftricks.
He's an accountant, he alsowent to law school and then he
also participated in thepolitical sphere in Columbia,
(06:26):
and he was always busy, but notthe busyness of like timing, but
more the busyness of helpingacross multiple organizations,
across multiple people.
I just always saw him advisingand helping others.
And my mom was the same way.
She's a teacher, former teacher, but at the same time like just
(06:50):
very hard worker, alwayslooking out for how she could
improve herself and be better inthe role that she was
performing.
And even in those likesituations where I truly saw
they were being challenged, theypersevered.
They always persevered andpursued what was right, what was
the right outcome.
(07:10):
And so I think that grit issomething that I see as a big
skill where, just because of thelife circumstances that I have
been through.
When there's challenges thatcome to me as an advisor, as I
work with my clients, I don'tlose sight that there's always
going to be a solution.
So even though problems can bevery complex at times, we will
(07:34):
always find an outcome for thatspecific challenge.
And then I would say, anothercharacteristic too is I'm very
analytical.
It's one of those things that,from a math perspective at
school, I always did great atmath.
I loved math classes honestly,like anything from algebra to
(07:56):
calculus.
I've been a huge math geek myentire life.
And then like bringing thatinto using things like Excel.
I'm an Excel nerd, I willconfess to that.
I love anything that has to dowith Excel.
But those analytical andtechnical skills that have
really served me well when itcomes to understanding all of
(08:17):
the numbers and budgeting andjust strategic calculations and
projections for the benefitprograms, again, that my clients
and I partner with Deploy towork on, that technical slash
analytical skill has served mereally, really well.
And I would say the last one isI come from a different culture
(08:39):
and I definitely had to learn alot of new things when I came
to the US in terms of what'sacceptable and what's not
acceptable, which was differentfrom my upbringings.
This challenge, coming from youknow what, perhaps, is coming
from a place where this specificCFO, ceo, even an employee, you
(09:09):
know, based on the situationthat they're going through,
there's an emotional response toit and there's a reason for
that.
And just being able to see thathuman side of the situation and
empathize with it in order tocome up with a solution has
really helped me develop a lotof trust with the employers that
I work with.
Speaker 1 (09:29):
That's awesome, I've seen.
Definitely in watching youperform your craft and succeed
in that way, I can definitelysee those three things of
culture.
Grit I also call toughness.
You have a toughness about youand then you're just analytical
nature.
I mean numbers is the languageof business, right, and
understanding that really well,and how the numbers within a
(09:51):
health plan like pervadesthroughout a business, is really
important for sure.
Well, two of the three of thoseare going back and like talking
about your roots and obviouslyyou have a, you know, one of my
favorite pictures behind youBogota.
One of my favorite picturesbehind you, bogota.
Obviously, your journey startedvery uniquely from others in
the benefits realm, growing upin Bogota and then coming to the
(10:13):
United States.
Can you share with us just kindof like what it was like
growing up in Bogota and thenwhat were the circumstances
around, what brought you to theUnited States and how that
played out the first, maybe even48 hours while you were here,
what that was like?
Speaker 2 (10:32):
Yeah, we can go down memory lane a little bit.
So, growing up Bogota.
For those who don't know,bogota is the capital of
Colombia.
Bogota is a city currently.
I think we just crossed the 11million people mark, so it's a
very large city.
Speaker 1 (10:50):
That's like New York City style, right there, yes.
Speaker 2 (10:53):
Yeah, it is a very large city, all sorts of
ethnicities and backgrounds andyou know, there's just a lot of
people, a lot of people withinthat city.
And growing up I would say thatwas interesting for me because,
you know, as a kid I mean yougo through kind of what we
(11:14):
consider the traditional aspectsof childhood of like taking
vacations and going to school.
I went to an all girls schoolbut the school that I went to
was a program that's like anEnglish immersion program.
So it was started by,technically, sisters from the
(11:34):
Franciscan community thatactually resided in Rochester,
minnesota, and their intent wasto develop a system from
kindergarten through 12th grade,senior year in high school,
where these girls were immersedfully in learning English and
learning all sorts of subjectsin English to make them fluent
(11:56):
and be able to speak Englishwhen they graduated.
So all that is pretty normal.
Bogota is a busy city.
I mean you do have lots oftraffic.
It's to get from point A topoint B you do have to plan well
in advance, and this was priorto the day and age of Waze or
MapQuest or anything like that.
So just growing up in a citylike that, but for me
(12:18):
specifically, I think one of thethings that made my childhood a
little bit different was mydad's involvement in politics.
I definitely witnessed thingsthat I love to share, because I
know that not everybody wentthrough the same experiences
that I did, and I would say acouple of things that I like to
share are so my dad was heavilyinvolved when the drug cartels
(12:41):
in the 90s were fighting forafter Pablo Escobar died, were
fighting to take over histerritory and his market share
and his routes to ship cocaineto different parts of the world,
and so my dad was heavilyinvolved in the anti-narcotics
task force.
So with that comes a lot ofsafety concerns for him and for
(13:04):
his family.
That comes a lot of safetyconcerns for him and for his
family, and so that definitelymade my childhood a little bit
different.
Just because from again,vacations, going to the park,
going to school, we always hadguards that were behind us in an
SUV.
So you can picture like JasonBourne or James Bond movies
where you have like the blackSuburbans or you know whatever,
(13:27):
as you leave kind of behind youat all times making sure that
you and your family are safe.
So that was a little differentgrowing up A little yeah, a
little bit.
But from that point on I wentthrough school and, luckily for
me, my mom and dad really pushedme to be one of the best
students in the class andactually that played out
(13:49):
excellent for me because I wasawarded a scholarship to come to
the US and go to school herefor college.
It was a fully coveredscholarship.
Speaker 1 (13:59):
Real quick before we go to like going to college in
the United States.
Why do you think going to likean English immersion school was
like really important to yourparents to have you do that?
Speaker 2 (14:12):
Yeah, that's a very good question.
I've asked that question myselfto my parents because you know
it's a decision that technicallyI didn't make.
They made the decision for me.
And they have two big reasonsfor that.
The first one was in the late90s, early 2000s.
Globalization was starting tobe a trend where countries were
(14:35):
starting to trade, you know,create trading agreements with
each other.
Dad started identifying that.
He understood that in order forhis kids to go far, it could
open a lot of doors if they knewor learned a second language at
least, if not more.
And so yeah to your point, likegoing to that school.
(14:59):
Right now, nowadays there's alot more schools that teach a
second language, but at thatpoint in time when I went
through that school, there werea handful of schools that wanted
in Bovita to attend to do that.
So that's one of the reasons.
But the second one too, wasbased on kind of some close
calls.
I'll leave it at that that mydad had, from a livelihood and
(15:22):
safety perspective, a livelihoodand safety perspective.
He really thought that it wasprobably a better way to keep
his kids safe if they went to adifferent country and started
their life that way.
So there's part of that as wellthat he potentially considered
asylum for us in a differentcountry to protect us from some
of the unsafe things that werehappening.
Speaker 1 (15:44):
So there's like a globalization, like trade and
how the world operated, as wellas like.
My children probably need tograduate out of Columbia and
head somewhere, and so I need toget them set up in a way that
can happen more seamlessly.
Speaker 2 (16:00):
Yeah.
Speaker 1 (16:01):
Wow.
So you got a scholarship, yougot awarded a scholarship.
Speaker 2 (16:06):
I did.
I got awarded that scholarshipand I will never forget that day
, because it was my mom, and Iattended the school meeting
where we had been hinted thatthese scholarships were going to
be granted.
So the sisters, the Franciscansisters, are reading the names
and they read my name as DianaCarolina, which technically the
(16:27):
way you say my name properly inSpanish is Diana Catalina.
So there's a little bit ofdifference there and my mom just
like elbows me and she's likeis that you?
Speaker 1 (16:41):
And I'm like, yeah, I'm pretty sure that's me.
Speaker 2 (16:43):
So, like they pronounce it wrong, we're so
confused and we just kind oflooked at each other and we're
like, yeah, pretty sure that'sme.
So I went up and, effectively,yeah, it was me who I was
awarded a scholarship.
So, anyway, get the scholarship.
And I have three schools tochoose from.
First one is in Iowa, secondone is in Wisconsin and third
(17:08):
one is in Iowa.
Second one is in Wisconsin andthird one is in Minnesota.
And I had never been to any ofthose states in the US
previously.
So we literally pulled, oncethey told us the options, we go
back home my dad's not home, heis at work and we pull up a map
on the computer and just like,like, where are these schools
located at and in the map?
I'm like, well, I know thatwinter is pretty bad in the
(17:29):
northern part of the country, soI'm thinking Iowa being closer
to the south, it's got to be waybetter than the other two.
And uh, of course there were,you know, a lot of meetings that
took place as well to make suremy major and all of that
aligned.
But ultimately picked the aschool in Iowa Loris College in
Dubuque mostly because weexpected more favorable weather,
(17:51):
which now, 20 years later, notreally the case, but that's how
we based on what are the reasonsof the decision.
But yeah, attended.
Loris, I definitely had some,like you said, some cultural
things that I had to learn.
I would say one of the funniestone that I can recall was
getting my first car paid bymyself, and I was so proud of it
(18:15):
.
It was a Pontiac Sunfire.
It was like a 1990 dark bluePontiac Sunfire.
It was a rattling thing onwheels, but I was so proud of it
.
I think I paid 1200 bucks forit.
And one of the first time I'mdriving through Dubuque streets
and I see this police car rightbehind me with the lights on.
(18:36):
Well, in Bogota, whensomebody's getting pulled over
for speeding or whatever thecase might be, the sirens are
also going off within thatpolice car.
So I kept driving.
I'm like, okay, this is not forme, it's definitely not for me
to pull over.
So I keep driving and thepolice car keeps getting closer
and closer and closer to my car.
So now I'm starting to thinkmaybe this is for me, maybe I
(18:59):
should pull over.
What should I do here?
And I'm just by myself there.
So I pulled over to a parkinglot and I remember it was a
church parking lot and thepolice guy comes right behind me
and he comes over to you knowroll down the window because it
was rolling down the window inthose days, and he's like
license and registration please.
And then, you know, I pulled youover and I said no, I don't
(19:22):
know, but I'll, I'll get you mystuff.
So I got my light, my driver'slicense, my car registration,
and I put a twenty dollar billin between those two and I gave
it to the officer and he looksat that and just kind of lifts
his eyes and just says do youknow what you're doing?
What is this for?
And I said, no, it's totallyfine, you can keep that, that's
(19:45):
no problem.
Because again, back in myhometown nothing that I'm super
proud of, but you know ithappens where people avoid
tickets by providing a littlebit of a payout to the cops or
to the police and they're justlet go.
Speaker 1 (20:01):
There's I mean cultural difference, right.
Speaker 2 (20:04):
Yeah, absolutely.
So I thought that wascompletely okay here and I said,
no, it's fine, you can keep it.
Just, you know, go forward withwhatever you need to do.
And he's like, do you reallyknow what you're doing right now
?
And he was getting kind ofupset and so I pulled another
twenty dollar bill and I gavehim that one as well and I said,
ok, this should do it.
(20:26):
This should take a while.
Speaker 1 (20:28):
Doubling down.
Speaker 2 (20:29):
Yeah, Doubling down, yeah, doubling down my odds.
And I think at that point hekind of chuckled and he's like
where are you from?
So I explained what I was from.
I'm an international student, Igo to Loras College I'm a few
blocks away and he totallyunderstood at that point.
Okay, this girl really does notknow that this is not something
(20:50):
that's appropriate.
So he explained, he gave me theclass, he explained to me that
that was completely wrong and Iapologized.
I didn't get a warning or aticket.
I think he saw my panickingface of like, oh my goodness,
what am I getting myself into?
I could go to jail for this.
And he let me go.
But that was one of the veryfirst shocks that I experienced
(21:11):
when I came to the US.
Speaker 1 (21:15):
Oh my gosh, that's so good.
I also think that just kind ofreveals like the beauty in
different places and thecultural norms and like just the
things that make differentplaces like home to different
people, right, it's just that'sjust like a small revelation of
that.
So you came from Bogota,columbia of 11 million people,
(21:36):
which we just recently did ageography lesson on Bogota.
It's like a mountainous area,right, yes, and you went to
Dubuque, iowa.
Speaker 2 (21:46):
Population in Dubuque is what I think we're at about
90,000.
Speaker 1 (21:52):
90,000 people.
So 11 million to 90,000 people.
I would say it was actuallysurprising to me when I first
went to Dubuque, which was onyour first day.
Is it's actually pretty likehilly around Dubuque?
It's not like Midwestern flatlike Indiana, is it's actually
fairly hilly next to theMississippi River?
(22:15):
But 11 million to 90,000 people, mountains to hills.
What was the first couple ofweeks like, when you showed up
and you realized my goodness,it's not necessarily terribly
warm in Iowa and like where areall the people?
Speaker 2 (22:36):
I love that question this is such a fun question
because I do get asked that alot and to give you a visual.
So Dubuque, iowa, has anairport.
So I did have to, you know,make a couple of stops before
arriving to Dubuque.
But as I'm flying into Dubuque,there's no buildings,
(22:57):
everything I can see.
This is August, so August 19 of2005.
I'm flying in with two giganticsuitcase where my try to bring
as much as I could of my lifewith me, with weight limitations
, and we paid for overweight,but anyway I'm flying in and I
see cornfield after cornfield,because, of course, at that
(23:18):
point in time in August, thecorn is already starting to
tassel.
It's tall, you know, it's lotsof grain and I'm like where are
the, you know, kind of like theskyscrapers or any sort of
apartment buildings or anythinglike that?
Don't see anything, for thatmatter.
So we land in Dubuque andthere's two other students of my
(23:42):
school as well, so three of uscame to school and we arrive at
the airport and this airport hasone runway.
So again we're like where?
Speaker 1 (23:53):
are we now?
Speaker 2 (23:54):
What's happening here .
Grab our bags and we aremeeting our host family.
So I'm very blessed that I didhave an individual who worked at
Laura's.
Him and his wife welcomed threeof us into their home to live
for the time that we were incollege, which I will be
(24:16):
eternally grateful for.
But they pick us up.
They have a Chevy Impala.
At the time I remember thatwe're struggling to get all of
our bags in that car for thethree of us and get us there.
And they have a son too, too,and he came to welcome us and we
start driving on this likecounty roads and again we're all
looking at each other likewhere are we?
(24:38):
What kind of setup is this?
And they live in a very woodedarea as well, so we're not even
seeing anything.
Dubuque wise yet as it relatesto like the actual town.
Speaker 1 (24:51):
Right, this is the outside, you went straight to
the country yes, straightstraight to the country.
Speaker 2 (24:57):
You're seeing cattle, corn, cattle, corn, cattle,
corn.
That's kind of a the landscape.
And uh, I just remember askingthat night to Steve, my host dad
, like is this Dubuque, or arewe going to have to drive, you
know, 30 minutes or whatever toget to Dubuque?
(25:18):
And he said, no, this is, theseare the outskirts of Dubuque.
Dubuque looks, you know, prettymuch like this.
I mean, all you're going to seeonce we get into the actual
downtown is, you know, thecollege buildings and additional
like city buildings and whatnot.
But this is Iowa.
Welcome to Iowa.
And we all knew at that pointthat this was definitely going
(25:40):
to be a much differentexperience than we expected, but
I wouldn't have it any otherway.
Speaker 1 (25:47):
Yeah Well, at least in August you got tricked into
thinking that it was warmweather oh absolutely months yes
, that is for sure, because thatfirst winter was, uh, actually
what?
Speaker 2 (25:59):
it was?
One of the highest, uh, one ofthe snowiest winters on record,
the 2005 winter.
So I welcomed us with all ofits strength and mightiness when
winter came around.
Speaker 1 (26:13):
That's epic.
So you went to Loras and thenyou start your professional
career in Dubuque.
So tell me a little bit aboutthe professional journey right
out of school.
Speaker 2 (26:23):
Yeah, sure, so went to Loras, graduated Loras.
I did have a couple ofexperiences.
We talk about sales right and,like being an advisor, I pick a
lot from those two experiencesthat I had as it related to
sales.
The first one was I went toCalifornia for a summer because
(26:43):
I had a family member there thatworked for the Archdiocese of
Los Angeles and they wereworking with the Archdiocese on
selling cemetery plots, morespecifically for Latino members
of the community.
So we were speaking Spanish andhelping people understand how
to prepare and plan ahead forthat specific need.
(27:05):
And a lot of the time was spentat parish festivals, just
different events and communitieswhere we could seek a space to
talk to Hispanic families andthen be able to make
appointments with them and, youknow, get them educated on the
options and get them paying forthis specific type of planning.
So that was interesting.
(27:26):
I mean learning to sell andtalk about death, which I know
is kind of a topic that peopleare not super comfortable
talking about, was hard.
But I think that again, thatHispanic component really helped
relate values and culture withthe people that we were talking
to.
And then the next, the othersales experience that I went
through, was another summer Iwas recruited by a book selling
(27:51):
company an encyclopedia and bookselling company and so for that
it's all college kids we droveto Tennessee, to Nashville, for
training, so drove from Iowa toTennessee to get trained on how
to do this.
And then we drove to Californiato pick a neighborhood where we
(28:16):
had to get everything we needed.
So we had to ask for a place tostay, because they didn't have
a place to offer for us to stay.
We got started with some basecash, but everything else was
based on your book sales.
So, like to eat if you don'tsell, you're not eating.
Or you better have good friendsthat are with you there that
can lend you, you know, a peanutbutter and jelly sandwich,
(28:38):
because some of us, like myself,are not very good at selling
books, and so I had a lot ofgood friends that lend me their
hand.
Speaker 1 (28:46):
That wasn't your jam, huh.
Speaker 2 (28:48):
No, definitely not my jam, no, especially.
I mean the internet was aroundalready, and so that was a big
competitor and a big reason tosay no.
So those were my two like kindof sales experiences.
Post-college I got started.
I graduated during 2008.
So it was like the recessionthat was taking place in the US,
and so the job market was tough.
(29:10):
Lots of interviews, spent sometime unemployed and then I
finally was able to get aposition with a financial
institution in Dubuque and fromthere I kind of just worked my
way up through different roleswithin that institution and
eventually, in 2013, I made mytransition into benefits with a
(29:33):
local agency in Dubuque, andthat was 2013 on.
Have been in benefits sincethen excellent.
Speaker 1 (29:40):
I think it's one thing to note too.
We haven't said it yet, butyour husband owns his
chiropractor practice, so solike you've also had like an
experience with that of likebeing a business owner alongside
with him and running thebusiness with him, which is a
just another education in and ofitself.
Speaker 2 (30:01):
Yeah, that has been awesome.
I will say that.
You know, I always believethere are certain marriage tests
as part of being a couple, andI think that having kids is one,
but owning or starting abusiness together is definitely
another one, and we've had our.
You know, I heard Todd speak alittle bit about this in another
(30:22):
podcast, but peaks and valleyswe've had those as well.
I mean, there's a lot of stressthat comes from understanding
the financials of business planand getting the bank to lend us
some money to get started andthen trying to develop some
marketing to make sure that wecan get patients in the door
(30:43):
right.
That's how his business operatesis.
He's a chiropractor, so hetreats patients and if he does,
then he gets compensated for it.
So we have a lot of stressfultimes, but we always look back
and it's one of those thingsthat we're the most proud of.
It's like our marriage.
We've been married for 15 yearsand, through the good and bad
and the ugly we've made itthrough and we feel like we were
(31:06):
in a pretty good spot.
We have a successful businessfrom that perspective.
Speaker 1 (31:09):
So yeah, that's awesome.
I have a couple of good friendsthat are in business with their
spouses and described as abeautiful cobblestone road.
Obviously, no, cobblestoneroads are beautiful, but we also
know that they're bumpy attimes.
So, but I know, just like whatyou said, they said it too.
They wouldn't have it any otherway, so it's really cool.
So, 2013, you get into thebenefits world, you get
(31:33):
introduced.
What was your first role inbenefits?
And then?
Where did it progress fromthere?
Speaker 2 (31:39):
Yeah.
So I started as a benefitsmarketing representative and
this was from an agency whoseowner whose company owner I was
the last person that heinterviewed and then he passed
away.
He hired me and then he shortlyafter passed away.
So it was one of thosesituations where, like, I fell
(32:00):
in love with the mission, I fellin love with what he wanted to
accomplish with me and my role,and then he was gone and it was
a pretty quick transition to adifferent manager that I worked
with.
But from a benefits marketingrepresentative I learned from
scratch benefits.
I had to learn.
I had no clue how deductibleswork.
(32:22):
I had no clue what anout-of-pocket maximum was,
deductibles work.
I had no clue what anout-of-pocket maximum was
because, luckily enough, fromcollege through that time, my
husband and I had been prettyhealthy.
We never really had to use thehealth insurance.
So I had to learn a lot ofthose terms from scratch.
And then my primaryresponsibilities were to
spreadsheet Every single quote,every single proposal that came
(32:46):
in from a carrier.
I was putting them together ina spreadsheet in a comparison
and then giving those to theaccount manager as well as the
advisor to present to the client.
Speaker 1 (32:59):
And then, real quick, you mentioned marketing when we
have some listeners that aren'tnative to the insurance or
benefits space.
Most people, when they think ofmarketing, they think of like
marketing a product to an enduser.
But insurance is a funny thingwhere we like to use normal
words and give them differentdefinitions.
What does marketing mean in theworld of benefits?
Speaker 2 (33:23):
Yeah, that's a great question in the world of
benefits.
Yeah, that's a great question.
So marketing in the world ofbenefits is very well used for
the research and comparison ofpricing of various solutions or
various vendors or insurancecompanies, and then really that
is what is presented toemployers as the options that
(33:46):
are on the table for theirbenefits program.
So there's a lot of negotiationthat's involved in that, as
well as relationship managementand, of course, the technical
part of it, the analyticalskills.
Speaker 1 (33:58):
Yeah, very different than that, right?
We're going on gettingproposals and then figuring out
how to get it to a place whereit's presentable to a client.
So you started out learning thebasics.
You're in the marketing realm.
What did it look like to growinto that role?
Speaker 2 (34:14):
Yeah.
So as I got more experiencewith the terminology and showing
the producers or the advisorsthe options, I started adding my
touch to it and saying here'swho I would recommend, here's
who.
I think makes a lot of sensebecause I got to know all of the
vendors and all of the carriersextremely well.
We were having conversationsday in and day out and of course
(34:36):
you know they want to pitchtheir best to you so that they
become your recommendation.
So as I started providingrecommendation to producers and
advisors, I think that wasnoticed within the members of
the management team and so Istarted getting more opportunity
to participate in salesconversations with prospects as
(34:57):
well as with existing clients.
There was a lot of trust put inme to, also from a producer, to
take the front seat and presentthe options to the client.
So thankfully I did get a lotof exposure on how to maneuver
and how to navigate aconversation with CEOs, cfos and
(35:18):
HR professionals that way.
Speaker 1 (35:20):
So you could have just grown in that role of plug
and play I'm supposed to do thistask, so I'm going to do this
task and complete it.
But you leaned in further andsaid I'm going to add strategy
to this, how can we improve whatwe're doing?
And ultimately you startedadvising the advisor.
(35:41):
Right, so the producer istechnically the advisor to the
client.
You started advising theadvisor on hey, I think you
should do this, that or theother, and because you're so
technically sound on the productand everything else, that
advisor just kind of got out ofthe way because you knew it
better and wanted you to presentthat to the client.
It's pretty fascinating.
Speaker 2 (36:02):
Yeah.
Speaker 1 (36:02):
What was that motivation like of just hey, I
just don't want to sit here andgive you the proposal, Like I
want to get involved here.
Speaker 2 (36:09):
I have been a true believer that ever since again
since I got the opportunity tocome to the U?
S that there's gotta be areason why I'm here, you know,
because it's really hard notevery day, because it's really
hard not every day, but a lot ofdays it's hard to be away from
home.
But I also think that God hasput me in this position because
(36:37):
there is a mission that I needto fulfill where I'm at, and so,
with every single job that Ihave held that is how I hold
myself accountable is am I doingthe best that I can in the
position that I have held?
That is how I hold myselfaccountable.
Is am I doing the best that Ican in the position that I have,
with the resources that I havefor the people that I work with
and I think, some people.
I remember being calledunsettled many different times
(36:57):
because I was looking to getbetter and ask for opportunities
for professional development,personal development, always
looking for that.
I'm always asking thosequestions, but it's it comes
from a place of more likeambition and wanting to continue
to be better and conduct mycalling here where I'm at today.
(37:18):
So I think that's what hasalways inspired me and motivated
me to do more than what it isasked of me is because there is
a higher calling for me here.
Speaker 1 (37:30):
That's awesome.
Well, that calling led you to aconference 2021, right, that's
where I got to meet you.
Speaker 2 (37:36):
That's right.
Speaker 1 (37:37):
So sat at the same table talk shop a little bit,
but talk about attending thatconference and then kind of what
transpired after that.
Speaker 2 (37:45):
Yeah, so, part of giving recommendations to the
producers that I was workingwith, I started getting a sense
of frustration from clients,getting a sense of frustration
from employees because of theharsh reality of our healthcare
system.
Just as ways to control costs,employers were raising
(38:07):
deductibles as a way to do soand maintain or keep costs down,
but then delivering those newsto employees was really tough.
I remember very vividly beingat employee enrollment meetings,
helping with those and havingemployees walk out because they
were so disappointed at thebenefits that were being offered
at those companies and I had tofigure there's got to be a
(38:29):
different way to do this,there's got to be a better way
to do this, and thankfully,social media was a great way to
do that.
I literally hopped on LinkedInand started following people
like Dave Chase and startedreading information about like
David Contorno, and I rememberalso following Nelson Griswold.
(38:51):
In fact, I had started to set upmeetings with him to see if I
could learn about, you know, abook that he had just come out
with, and how he was advisingand coaching agencies into a
different way of doing benefits,a better way, and so that
conference in 2021 was, I think,my first step towards saying I
(39:17):
need to become savvy on whatelse is out there and then be
able to bring that to my regionwhere I'm at today, because I
know that from a Midwestperspective.
I think a lot of the times theMidwest region is considered
kind of a late adopter ofcertain things that may be
cutting edge, that are moreearly on adopted in, like the
(39:39):
East Coast or the West Coast,and that's totally fine.
But I wanted to be one of thefirst ones to bring it to the
region.
But I needed to understand itas best as I could.
Speaker 1 (39:49):
Yeah, totally agree.
So similar story from myperspective.
Yeah, you get tired of it.
I think probably a lot of theadvisors that we've become
friends with we all have thesame like catchphrase of like
what went through our heads isthere's got to be a better way.
Like literally those exact samewords there's got to be a
better way.
This is so terrible.
This healthcare delivery modelis disgusting and you can see it
(40:13):
crushing employees that you'restanding in front of and it's
ridiculous.
But yeah, so we met at theconference and then you followed
up and you decided to come onboard at Conor Insurance and
that's been awesome.
You've done a great job.
So I'm really proud of you andwhat you've done.
This award is certainlydeserved from what I've seen.
So top five broker of the yearor, I guess, advisor of the year
(40:35):
.
That's right, I'm so old I knowit as broker of the year, but
now it's the advisor of the yeartop five across the country.
So we'll find out soon who isthe winner.
But what we really know is allfive of you are winners, because
five out of the entire countryis incredible.
So congrats to you.
Before we get into our finalquestions I wanted to get into
(40:57):
just real quick I want to askyou like you look back.
You've almost been at Connorfor three years and you've had
the experience that you've had.
What do you hope for the nextthree years in your advising
career Like?
What are your aspirations for?
What that looks like.
Speaker 2 (41:16):
That's a really good question.
I think that one of the thingsthat I still am working towards
is being able to bring change tomy backyard like that, my
community here.
You know I've been within thiscommunity for 20 years.
Actually, this year marks my20th year of being here and I
(41:37):
know so many people just becauseI went to college here and now
I have three kids that areattending, you know, local
schools here and so I'm startingto get to know the parents of
other kids that are in theirclass and it's like kind of that
saying of like loving yourneighbor.
I want to love my neighbors bybeing able to provide affordable
(42:01):
health care to them, Because Ihave been a health care user
again, had three kids, so, ofcourse, you know I had to
deliver my kids in hospital, soI understand very much how it
works now and thankfully, withConnor and having my third child
, I was able to experience abetter way of doing so and
within my community.
Speaker 1 (42:21):
So I know it's possible, I know it can be done,
and so for the next you know,three, five, 10 years, I really
want to help bring thatexcellent experience that I had
to other people in my community,Because I know, go, I'm trying,
yeah, now then in yourcommunity is lucky to have you,
(42:44):
and I'll be fun to watch themrealize that as you continue to
grow your client base in thatgreater area Cause really, like
Dubuque, is right on the borderof Wisconsin, so your market
really is Iowa, wisconsin,illinois, I mean, they're all
right there and even up inMinnesota where we have clients
already.
It's a great state.
So we have two questions thatwe ask everyone that comes on
(43:06):
the pod.
So the first question is andyou probably have several to
choose from actually what is therisk you have taken that has
changed your life?
Speaker 2 (43:16):
Oh, that's a yeah, definitely have several ones.
I think the risk that propelledeverything that I've been doing
here was the risk of coming toa different country, like that
is.
It was a hard decision at 17 toleave home.
I know it was super hard and Iunderstand it now as a parent
(43:37):
like letting your children goand pursue their dreams, but
much further, into anothercountry, another culture and a
very different setting.
It's hard, but it's also adecision that has opened so many
doors.
So many doors met fantasticpeople, being able to have some
of the best memories in my lifemeeting my husband.
(44:00):
That would have never happenedif I wouldn't have come to the
US.
We met in college, and so Ithink that just making the leap
of faith and deciding to buildmy dreams in the US has been one
of the best risks I could haveever taken.
Speaker 1 (44:16):
I think that is an absolute fascinating story of
trying to put myself in yourshoes, of being an immigrant and
going somewhere new.
And you mentioned, like 17years old, hopping on an
airplane and going to adifferent country to live and go
to school.
And there's probably severalparents, maybe even listening
right now, that like haveheartburn about their 17 year
old driving on the interstate.
(44:37):
You know like just theincredible risk.
I mean, it is an incrediblerisk, so that's awesome.
So the second question is moreabout like, maybe future dreams,
but what's unfinished for youthat you have the resolve to
complete in the near or not sonear future?
Speaker 2 (44:57):
That's an excellent question too.
I think that you know kind ofwhat I mentioned before about
being able to make an impact inmy community is so significant,
and especially because I do wantlike my kids are my motivation
every day when I wake up and goto work, even when I'm having a
(45:17):
bad day, I just think of themand think of they deserve better
healthcare experiences.
They deserve to get taken careof by high quality physicians
that have the best outcomespossible for whatever health
challenges they face, and so thework that I'm doing now, even
(45:39):
though it's one teeny tiny pieceof sand in this gigantic
behemoth of a healthcare system,I'm hopeful that it will help
make their experience better,and so I have the resolve to not
just make an impact in mycommunity, but also to help
design a better healthcaresystem for my kids.
Speaker 1 (45:59):
That's awesome.
I don't think there's a betterplace to end than that.
De Diana, thanks for joining metoday on the pod.
Congrats to you on the 2025Advisor of the Year finalist
Super well-deserved and thanksto the audience for joining us
for another episode of the Riskand Resolve pod.
(46:20):
Thanks for tuning in to Riskand Resolve.
See you next time.
You're listening to Risk and Resolve, and now for
your hosts, ben Conner and ToddHufford.
Welcome back to another episodeof the Risk and Resolve pod.
I'm your host, ben Conner, andtoday our special guest is
Deanna Miller, benefits Advisorat Conor Insurance and drumroll
(00:27):
2025 Advisor of the Year,finalist that's recognized by
Benefits Pro, one of the topfive advisors recognized in the
entire country.
Deanna, how are you doing today?
Speaker 2 (00:41):
Hey Ben, I'm doing well.
It's an honor to be here.
I'm very excited to be a partof the podcast, so thanks for
having me.
Speaker 1 (00:48):
Yeah Well, congrats to you on the recent recognition
of your long-term efforts iskind of how I view it.
This has been something that'sbeen on your professional bucket
list for a little bit of time,hasn't it?
Speaker 2 (01:04):
Yeah, it sure has.
It's one of those things where,you know, we kind of see all
sorts of colleagues and advisorsacross the country being
recognized for the efforts andtheir hard work, and it's one of
those things that, when Istarted in the benefits industry
, I thought you know what, oneday I'm going to be on the cover
(01:27):
of that magazine, because Ibelieve that hard work deserves
recognition.
And I'll definitely say that Ihave a pretty strong work ethic
when it comes to that.
And just seeing people like you, you know, following your, your
footsteps on that, and nowseeing my name within the
recognition, is definitely anhonor that I don't take for
(01:47):
granted.
So pretty excited to see one ofmy dreams come true.
Speaker 1 (01:51):
That's awesome and it's been fun for me to be able
to watch that occur.
So you talked about motivationand work ethic as like kind of
some of the main things.
I'm sure there are othercharacteristics that go into
play, but what's kind of thebehind the scenes of like what
does that hard work look like tobecome an advisor of the year
(02:12):
finalists?
Like what does that look likeon a day-to-day basis?
Speaker 2 (02:16):
It's an advisor role.
I feel like it's wearingmultiple hats because you do
have to tend to many differentstakeholders.
So of course, you have theemployers that you work with,
and within that employer setup,there's also different types of
parties as well.
(02:36):
I mean I have my CFOs, my CEOsand my HR professionals, who I'm
working with from a strategicperspective day in and day out
to understand their companyobjectives and help accomplish
those objectives through themanagement of the benefit
programs that they offer,partnering with us.
But in addition to that, wehave their employee population,
(02:58):
who also has very specific needs, and it is my responsibility
and I take that very seriouslyin helping our team.
So everybody who supports ourclients, including account
managers as well as membersupport individuals, understand
what sort of needs that employeepopulation has and help serve
(03:19):
those needs as best as we can.
Speaker 1 (03:22):
That's not an easy task.
Speaker 2 (03:23):
No no.
Speaker 1 (03:25):
At the same time.
Speaker 2 (03:26):
Yeah, but it's also one of those things where I feel
like the advisor is also thefirst line of defense if
something goes wrong, and so wehave to be prepared to be that
problem solver.
That can come from manydifferent aspects of a plan
again, or stakeholders withinthat employer, and so sometimes
(03:47):
too, from an advisor hard workperspective.
Advisors don't get a lot ofrecognition when it comes from
clients, because usually youknow if things are going well,
things are quiet and things arenot going well.
That's when we really hear froma specific employer and
something that's not going well,and so I do feel like the
advisor role for it to deserveor to receive recognition.
(04:09):
It doesn't happen very often,and so when it happens, you got
to take on it, but it's a lot ofhard work.
You got to wear a lot ofdifferent hats as being an
advisor.
Speaker 1 (04:19):
Yeah, I always kind of found that, or at least I
feel like I've learned over thelast many years that our clients
should actually look at inthose hard times, like when
things are like a little diceyor problems occur, like that's
when they get to find out likeif they actually hired the right
advisor, because it's easy foreveryone to look great when it's
going well, but it's like youfind out what your advisor is
(04:42):
made of and how good they are ontheir feet and how well they
think and all those sorts ofthings.
When things go wrong, whenthere's problems that occur,
yeah, you're 100 percent right.
Speaker 2 (04:52):
I feel like it is in times of pressure that a
character of a person reallycomes through the advisor, vice
versa, back and forth.
Seeing how those problems getresolved will really be a test
to you know.
Are they the right fit or arethey not the?
Speaker 1 (05:11):
right fit.
So don't they say like pressure, like obviously pressure can
crush things right, like justgeneral, like science, but also
pressure is what createsdiamonds, right?
So, there's opposite thingsthat can occur from an event
like pressure.
So what would you say?
Is your like secret sauce foryour personal craft of advising?
(05:31):
Like what is the thing thatyou're like?
You know what like thesecharacteristics to my approach
is how I accomplish what I canaccomplish with my clients on a
daily basis.
Speaker 2 (05:42):
That's a very good question.
Well, I think that a lot of mysuccess is attributed to my
personal experiences in life andhow I have been able to face,
you know, adversity, challengesand be able to come through
successfully from those.
I think one of those skills isgrit.
(06:03):
I think that's a characteristicthat, from my childhood, was
something that I always saw inmy parents, my father especially
.
He was a man of all sorts oftricks.
He's an accountant, he alsowent to law school and then he
also participated in thepolitical sphere in Columbia,
(06:26):
and he was always busy, but notthe busyness of like timing, but
more the busyness of helpingacross multiple organizations,
across multiple people.
I just always saw him advisingand helping others.
And my mom was the same way.
She's a teacher, former teacher, but at the same time like just
(06:50):
very hard worker, alwayslooking out for how she could
improve herself and be better inthe role that she was
performing.
And even in those likesituations where I truly saw
they were being challenged, theypersevered.
They always persevered andpursued what was right, what was
the right outcome.
(07:10):
And so I think that grit issomething that I see as a big
skill where, just because of thelife circumstances that I have
been through.
When there's challenges thatcome to me as an advisor, as I
work with my clients, I don'tlose sight that there's always
going to be a solution.
So even though problems can bevery complex at times, we will
(07:34):
always find an outcome for thatspecific challenge.
And then I would say, anothercharacteristic too is I'm very
analytical.
It's one of those things that,from a math perspective at
school, I always did great atmath.
I loved math classes honestly,like anything from algebra to
(07:56):
calculus.
I've been a huge math geek myentire life.
And then like bringing thatinto using things like Excel.
I'm an Excel nerd, I willconfess to that.
I love anything that has to dowith Excel.
But those analytical andtechnical skills that have
really served me well when itcomes to understanding all of
(08:17):
the numbers and budgeting andjust strategic calculations and
projections for the benefitprograms, again, that my clients
and I partner with Deploy towork on, that technical slash
analytical skill has served mereally, really well.
And I would say the last one isI come from a different culture
(08:39):
and I definitely had to learn alot of new things when I came
to the US in terms of what'sacceptable and what's not
acceptable, which was differentfrom my upbringings.
This challenge, coming from youknow what, perhaps, is coming
from a place where this specificCFO, ceo, even an employee, you
(09:09):
know, based on the situationthat they're going through,
there's an emotional response toit and there's a reason for
that.
And just being able to see thathuman side of the situation and
empathize with it in order tocome up with a solution has
really helped me develop a lotof trust with the employers that
I work with.
Speaker 1 (09:29):
That's awesome, I've seen.
Definitely in watching youperform your craft and succeed
in that way, I can definitelysee those three things of
culture.
Grit I also call toughness.
You have a toughness about youand then you're just analytical
nature.
I mean numbers is the languageof business, right, and
understanding that really well,and how the numbers within a
(09:51):
health plan like pervadesthroughout a business, is really
important for sure.
Well, two of the three of thoseare going back and like talking
about your roots and obviouslyyou have a, you know, one of my
favorite pictures behind youBogota.
One of my favorite picturesbehind you, bogota.
Obviously, your journey startedvery uniquely from others in
the benefits realm, growing upin Bogota and then coming to the
(10:13):
United States.
Can you share with us just kindof like what it was like
growing up in Bogota and thenwhat were the circumstances
around, what brought you to theUnited States and how that
played out the first, maybe even48 hours while you were here,
what that was like?
Speaker 2 (10:32):
Yeah, we can go down memory lane a little bit.
So, growing up Bogota.
For those who don't know,bogota is the capital of
Colombia.
Bogota is a city currently.
I think we just crossed the 11million people mark, so it's a
very large city.
Speaker 1 (10:50):
That's like New York City style, right there, yes.
Speaker 2 (10:53):
Yeah, it is a very large city, all sorts of
ethnicities and backgrounds andyou know, there's just a lot of
people, a lot of people withinthat city.
And growing up I would say thatwas interesting for me because,
you know, as a kid I mean yougo through kind of what we
(11:14):
consider the traditional aspectsof childhood of like taking
vacations and going to school.
I went to an all girls schoolbut the school that I went to
was a program that's like anEnglish immersion program.
So it was started by,technically, sisters from the
(11:34):
Franciscan community thatactually resided in Rochester,
minnesota, and their intent wasto develop a system from
kindergarten through 12th grade,senior year in high school,
where these girls were immersedfully in learning English and
learning all sorts of subjectsin English to make them fluent
(11:56):
and be able to speak Englishwhen they graduated.
So all that is pretty normal.
Bogota is a busy city.
I mean you do have lots oftraffic.
It's to get from point A topoint B you do have to plan well
in advance, and this was priorto the day and age of Waze or
MapQuest or anything like that.
So just growing up in a citylike that, but for me
(12:18):
specifically, I think one of thethings that made my childhood a
little bit different was mydad's involvement in politics.
I definitely witnessed thingsthat I love to share, because I
know that not everybody wentthrough the same experiences
that I did, and I would say acouple of things that I like to
share are so my dad was heavilyinvolved when the drug cartels
(12:41):
in the 90s were fighting forafter Pablo Escobar died, were
fighting to take over histerritory and his market share
and his routes to ship cocaineto different parts of the world,
and so my dad was heavilyinvolved in the anti-narcotics
task force.
So with that comes a lot ofsafety concerns for him and for
(13:04):
his family.
That comes a lot of safetyconcerns for him and for his
family, and so that definitelymade my childhood a little bit
different.
Just because from again,vacations, going to the park,
going to school, we always hadguards that were behind us in an
SUV.
So you can picture like JasonBourne or James Bond movies
where you have like the blackSuburbans or you know whatever,
(13:27):
as you leave kind of behind youat all times making sure that
you and your family are safe.
So that was a little differentgrowing up A little yeah, a
little bit.
But from that point on I wentthrough school and, luckily for
me, my mom and dad really pushedme to be one of the best
students in the class andactually that played out
(13:49):
excellent for me because I wasawarded a scholarship to come to
the US and go to school herefor college.
It was a fully coveredscholarship.
Speaker 1 (13:59):
Real quick before we go to like going to college in
the United States.
Why do you think going to likean English immersion school was
like really important to yourparents to have you do that?
Speaker 2 (14:12):
Yeah, that's a very good question.
I've asked that question myselfto my parents because you know
it's a decision that technicallyI didn't make.
They made the decision for me.
And they have two big reasonsfor that.
The first one was in the late90s, early 2000s.
Globalization was starting tobe a trend where countries were
(14:35):
starting to trade, you know,create trading agreements with
each other.
Dad started identifying that.
He understood that in order forhis kids to go far, it could
open a lot of doors if they knewor learned a second language at
least, if not more.
And so yeah to your point, likegoing to that school.
(14:59):
Right now, nowadays there's alot more schools that teach a
second language, but at thatpoint in time when I went
through that school, there werea handful of schools that wanted
in Bovita to attend to do that.
So that's one of the reasons.
But the second one too, wasbased on kind of some close
calls.
I'll leave it at that that mydad had, from a livelihood and
(15:22):
safety perspective, a livelihoodand safety perspective.
He really thought that it wasprobably a better way to keep
his kids safe if they went to adifferent country and started
their life that way.
So there's part of that as wellthat he potentially considered
asylum for us in a differentcountry to protect us from some
of the unsafe things that werehappening.
Speaker 1 (15:44):
So there's like a globalization, like trade and
how the world operated, as wellas like.
My children probably need tograduate out of Columbia and
head somewhere, and so I need toget them set up in a way that
can happen more seamlessly.
Speaker 2 (16:00):
Yeah.
Speaker 1 (16:01):
Wow.
So you got a scholarship, yougot awarded a scholarship.
Speaker 2 (16:06):
I did.
I got awarded that scholarshipand I will never forget that day
, because it was my mom, and Iattended the school meeting
where we had been hinted thatthese scholarships were going to
be granted.
So the sisters, the Franciscansisters, are reading the names
and they read my name as DianaCarolina, which technically the
(16:27):
way you say my name properly inSpanish is Diana Catalina.
So there's a little bit ofdifference there and my mom just
like elbows me and she's likeis that you?
Speaker 1 (16:41):
And I'm like, yeah, I'm pretty sure that's me.
Speaker 2 (16:43):
So, like they pronounce it wrong, we're so
confused and we just kind oflooked at each other and we're
like, yeah, pretty sure that'sme.
So I went up and, effectively,yeah, it was me who I was
awarded a scholarship.
So, anyway, get the scholarship.
And I have three schools tochoose from.
First one is in Iowa, secondone is in Wisconsin and third
(17:08):
one is in Iowa.
Second one is in Wisconsin andthird one is in Minnesota.
And I had never been to any ofthose states in the US
previously.
So we literally pulled, oncethey told us the options, we go
back home my dad's not home, heis at work and we pull up a map
on the computer and just like,like, where are these schools
located at and in the map?
I'm like, well, I know thatwinter is pretty bad in the
(17:29):
northern part of the country, soI'm thinking Iowa being closer
to the south, it's got to be waybetter than the other two.
And uh, of course there were,you know, a lot of meetings that
took place as well to make suremy major and all of that
aligned.
But ultimately picked the aschool in Iowa Loris College in
Dubuque mostly because weexpected more favorable weather,
(17:51):
which now, 20 years later, notreally the case, but that's how
we based on what are the reasonsof the decision.
But yeah, attended.
Loris, I definitely had some,like you said, some cultural
things that I had to learn.
I would say one of the funniestone that I can recall was
getting my first car paid bymyself, and I was so proud of it
(18:15):
.
It was a Pontiac Sunfire.
It was like a 1990 dark bluePontiac Sunfire.
It was a rattling thing onwheels, but I was so proud of it
.
I think I paid 1200 bucks forit.
And one of the first time I'mdriving through Dubuque streets
and I see this police car rightbehind me with the lights on.
(18:36):
Well, in Bogota, whensomebody's getting pulled over
for speeding or whatever thecase might be, the sirens are
also going off within thatpolice car.
So I kept driving.
I'm like, okay, this is not forme, it's definitely not for me
to pull over.
So I keep driving and thepolice car keeps getting closer
and closer and closer to my car.
So now I'm starting to thinkmaybe this is for me, maybe I
(18:59):
should pull over.
What should I do here?
And I'm just by myself there.
So I pulled over to a parkinglot and I remember it was a
church parking lot and thepolice guy comes right behind me
and he comes over to you knowroll down the window because it
was rolling down the window inthose days, and he's like
license and registration please.
And then, you know, I pulled youover and I said no, I don't
(19:22):
know, but I'll, I'll get you mystuff.
So I got my light, my driver'slicense, my car registration,
and I put a twenty dollar billin between those two and I gave
it to the officer and he looksat that and just kind of lifts
his eyes and just says do youknow what you're doing?
What is this for?
And I said, no, it's totallyfine, you can keep that, that's
(19:45):
no problem.
Because again, back in myhometown nothing that I'm super
proud of, but you know ithappens where people avoid
tickets by providing a littlebit of a payout to the cops or
to the police and they're justlet go.
Speaker 1 (20:01):
There's I mean cultural difference, right.
Speaker 2 (20:04):
Yeah, absolutely.
So I thought that wascompletely okay here and I said,
no, it's fine, you can keep it.
Just, you know, go forward withwhatever you need to do.
And he's like, do you reallyknow what you're doing right now
?
And he was getting kind ofupset and so I pulled another
twenty dollar bill and I gavehim that one as well and I said,
ok, this should do it.
(20:26):
This should take a while.
Speaker 1 (20:28):
Doubling down.
Speaker 2 (20:29):
Yeah, Doubling down, yeah, doubling down my odds.
And I think at that point hekind of chuckled and he's like
where are you from?
So I explained what I was from.
I'm an international student, Igo to Loras College I'm a few
blocks away and he totallyunderstood at that point.
Okay, this girl really does notknow that this is not something
(20:50):
that's appropriate.
So he explained, he gave me theclass, he explained to me that
that was completely wrong and Iapologized.
I didn't get a warning or aticket.
I think he saw my panickingface of like, oh my goodness,
what am I getting myself into?
I could go to jail for this.
And he let me go.
But that was one of the veryfirst shocks that I experienced
(21:11):
when I came to the US.
Speaker 1 (21:15):
Oh my gosh, that's so good.
I also think that just kind ofreveals like the beauty in
different places and thecultural norms and like just the
things that make differentplaces like home to different
people, right, it's just that'sjust like a small revelation of
that.
So you came from Bogota,columbia of 11 million people,
(21:36):
which we just recently did ageography lesson on Bogota.
It's like a mountainous area,right, yes, and you went to
Dubuque, iowa.
Speaker 2 (21:46):
Population in Dubuque is what I think we're at about
90,000.
Speaker 1 (21:52):
90,000 people.
So 11 million to 90,000 people.
I would say it was actuallysurprising to me when I first
went to Dubuque, which was onyour first day.
Is it's actually pretty likehilly around Dubuque?
It's not like Midwestern flatlike Indiana, is it's actually
fairly hilly next to theMississippi River?
(22:15):
But 11 million to 90,000 people, mountains to hills.
What was the first couple ofweeks like, when you showed up
and you realized my goodness,it's not necessarily terribly
warm in Iowa and like where areall the people?
Speaker 2 (22:36):
I love that question this is such a fun question
because I do get asked that alot and to give you a visual.
So Dubuque, iowa, has anairport.
So I did have to, you know,make a couple of stops before
arriving to Dubuque.
But as I'm flying into Dubuque,there's no buildings,
(22:57):
everything I can see.
This is August, so August 19 of2005.
I'm flying in with two giganticsuitcase where my try to bring
as much as I could of my lifewith me, with weight limitations
, and we paid for overweight,but anyway I'm flying in and I
see cornfield after cornfield,because, of course, at that
(23:18):
point in time in August, thecorn is already starting to
tassel.
It's tall, you know, it's lotsof grain and I'm like where are
the, you know, kind of like theskyscrapers or any sort of
apartment buildings or anythinglike that?
Don't see anything, for thatmatter.
So we land in Dubuque andthere's two other students of my
(23:42):
school as well, so three of uscame to school and we arrive at
the airport and this airport hasone runway.
So again we're like where?
Speaker 1 (23:53):
are we now?
Speaker 2 (23:54):
What's happening here .
Grab our bags and we aremeeting our host family.
So I'm very blessed that I didhave an individual who worked at
Laura's.
Him and his wife welcomed threeof us into their home to live
for the time that we were incollege, which I will be
(24:16):
eternally grateful for.
But they pick us up.
They have a Chevy Impala.
At the time I remember thatwe're struggling to get all of
our bags in that car for thethree of us and get us there.
And they have a son too, too,and he came to welcome us and we
start driving on this likecounty roads and again we're all
looking at each other likewhere are we?
(24:38):
What kind of setup is this?
And they live in a very woodedarea as well, so we're not even
seeing anything.
Dubuque wise yet as it relatesto like the actual town.
Speaker 1 (24:51):
Right, this is the outside, you went straight to
the country yes, straightstraight to the country.
Speaker 2 (24:57):
You're seeing cattle, corn, cattle, corn, cattle,
corn.
That's kind of a the landscape.
And uh, I just remember askingthat night to Steve, my host dad
, like is this Dubuque, or arewe going to have to drive, you
know, 30 minutes or whatever toget to Dubuque?
(25:18):
And he said, no, this is, theseare the outskirts of Dubuque.
Dubuque looks, you know, prettymuch like this.
I mean, all you're going to seeonce we get into the actual
downtown is, you know, thecollege buildings and additional
like city buildings and whatnot.
But this is Iowa.
Welcome to Iowa.
And we all knew at that pointthat this was definitely going
(25:40):
to be a much differentexperience than we expected, but
I wouldn't have it any otherway.
Speaker 1 (25:47):
Yeah Well, at least in August you got tricked into
thinking that it was warmweather oh absolutely months yes
, that is for sure, because thatfirst winter was, uh, actually
what?
Speaker 2 (25:59):
it was?
One of the highest, uh, one ofthe snowiest winters on record,
the 2005 winter.
So I welcomed us with all ofits strength and mightiness when
winter came around.
Speaker 1 (26:13):
That's epic.
So you went to Loras and thenyou start your professional
career in Dubuque.
So tell me a little bit aboutthe professional journey right
out of school.
Speaker 2 (26:23):
Yeah, sure, so went to Loras, graduated Loras.
I did have a couple ofexperiences.
We talk about sales right and,like being an advisor, I pick a
lot from those two experiencesthat I had as it related to
sales.
The first one was I went toCalifornia for a summer because
(26:43):
I had a family member there thatworked for the Archdiocese of
Los Angeles and they wereworking with the Archdiocese on
selling cemetery plots, morespecifically for Latino members
of the community.
So we were speaking Spanish andhelping people understand how
to prepare and plan ahead forthat specific need.
(27:05):
And a lot of the time was spentat parish festivals, just
different events and communitieswhere we could seek a space to
talk to Hispanic families andthen be able to make
appointments with them and, youknow, get them educated on the
options and get them paying forthis specific type of planning.
So that was interesting.
(27:26):
I mean learning to sell andtalk about death, which I know
is kind of a topic that peopleare not super comfortable
talking about, was hard.
But I think that again, thatHispanic component really helped
relate values and culture withthe people that we were talking
to.
And then the next, the othersales experience that I went
through, was another summer Iwas recruited by a book selling
(27:51):
company an encyclopedia and bookselling company and so for that
it's all college kids we droveto Tennessee, to Nashville, for
training, so drove from Iowa toTennessee to get trained on how
to do this.
And then we drove to Californiato pick a neighborhood where we
(28:16):
had to get everything we needed.
So we had to ask for a place tostay, because they didn't have
a place to offer for us to stay.
We got started with some basecash, but everything else was
based on your book sales.
So, like to eat if you don'tsell, you're not eating.
Or you better have good friendsthat are with you there that
can lend you, you know, a peanutbutter and jelly sandwich,
(28:38):
because some of us, like myself,are not very good at selling
books, and so I had a lot ofgood friends that lend me their
hand.
Speaker 1 (28:46):
That wasn't your jam, huh.
Speaker 2 (28:48):
No, definitely not my jam, no, especially.
I mean the internet was aroundalready, and so that was a big
competitor and a big reason tosay no.
So those were my two like kindof sales experiences.
Post-college I got started.
I graduated during 2008.
So it was like the recessionthat was taking place in the US,
and so the job market was tough.
(29:10):
Lots of interviews, spent sometime unemployed and then I
finally was able to get aposition with a financial
institution in Dubuque and fromthere I kind of just worked my
way up through different roleswithin that institution and
eventually, in 2013, I made mytransition into benefits with a
(29:33):
local agency in Dubuque, andthat was 2013 on.
Have been in benefits sincethen excellent.
Speaker 1 (29:40):
I think it's one thing to note too.
We haven't said it yet, butyour husband owns his
chiropractor practice, so solike you've also had like an
experience with that of likebeing a business owner alongside
with him and running thebusiness with him, which is a
just another education in and ofitself.
Speaker 2 (30:01):
Yeah, that has been awesome.
I will say that.
You know, I always believethere are certain marriage tests
as part of being a couple, andI think that having kids is one,
but owning or starting abusiness together is definitely
another one, and we've had our.
You know, I heard Todd speak alittle bit about this in another
(30:22):
podcast, but peaks and valleyswe've had those as well.
I mean, there's a lot of stressthat comes from understanding
the financials of business planand getting the bank to lend us
some money to get started andthen trying to develop some
marketing to make sure that wecan get patients in the door
(30:43):
right.
That's how his business operatesis.
He's a chiropractor, so hetreats patients and if he does,
then he gets compensated for it.
So we have a lot of stressfultimes, but we always look back
and it's one of those thingsthat we're the most proud of.
It's like our marriage.
We've been married for 15 yearsand, through the good and bad
and the ugly we've made itthrough and we feel like we were
(31:06):
in a pretty good spot.
We have a successful businessfrom that perspective.
Speaker 1 (31:09):
So yeah, that's awesome.
I have a couple of good friendsthat are in business with their
spouses and described as abeautiful cobblestone road.
Obviously, no, cobblestoneroads are beautiful, but we also
know that they're bumpy attimes.
So, but I know, just like whatyou said, they said it too.
They wouldn't have it any otherway, so it's really cool.
So, 2013, you get into thebenefits world, you get
(31:33):
introduced.
What was your first role inbenefits?
And then?
Where did it progress fromthere?
Speaker 2 (31:39):
Yeah.
So I started as a benefitsmarketing representative and
this was from an agency whoseowner whose company owner I was
the last person that heinterviewed and then he passed
away.
He hired me and then he shortlyafter passed away.
So it was one of thosesituations where, like, I fell
(32:00):
in love with the mission, I fellin love with what he wanted to
accomplish with me and my role,and then he was gone and it was
a pretty quick transition to adifferent manager that I worked
with.
But from a benefits marketingrepresentative I learned from
scratch benefits.
I had to learn.
I had no clue how deductibleswork.
(32:22):
I had no clue what anout-of-pocket maximum was,
deductibles work.
I had no clue what anout-of-pocket maximum was
because, luckily enough, fromcollege through that time, my
husband and I had been prettyhealthy.
We never really had to use thehealth insurance.
So I had to learn a lot ofthose terms from scratch.
And then my primaryresponsibilities were to
spreadsheet Every single quote,every single proposal that came
(32:46):
in from a carrier.
I was putting them together ina spreadsheet in a comparison
and then giving those to theaccount manager as well as the
advisor to present to the client.
Speaker 1 (32:59):
And then, real quick, you mentioned marketing when we
have some listeners that aren'tnative to the insurance or
benefits space.
Most people, when they think ofmarketing, they think of like
marketing a product to an enduser.
But insurance is a funny thingwhere we like to use normal
words and give them differentdefinitions.
What does marketing mean in theworld of benefits?
Speaker 2 (33:23):
Yeah, that's a great question in the world of
benefits.
Yeah, that's a great question.
So marketing in the world ofbenefits is very well used for
the research and comparison ofpricing of various solutions or
various vendors or insurancecompanies, and then really that
is what is presented toemployers as the options that
(33:46):
are on the table for theirbenefits program.
So there's a lot of negotiationthat's involved in that, as
well as relationship managementand, of course, the technical
part of it, the analyticalskills.
Speaker 1 (33:58):
Yeah, very different than that, right?
We're going on gettingproposals and then figuring out
how to get it to a place whereit's presentable to a client.
So you started out learning thebasics.
You're in the marketing realm.
What did it look like to growinto that role?
Speaker 2 (34:14):
Yeah.
So as I got more experiencewith the terminology and showing
the producers or the advisorsthe options, I started adding my
touch to it and saying here'swho I would recommend, here's
who.
I think makes a lot of sensebecause I got to know all of the
vendors and all of the carriersextremely well.
We were having conversationsday in and day out and of course
(34:36):
you know they want to pitchtheir best to you so that they
become your recommendation.
So as I started providingrecommendation to producers and
advisors, I think that wasnoticed within the members of
the management team and so Istarted getting more opportunity
to participate in salesconversations with prospects as
(34:57):
well as with existing clients.
There was a lot of trust put inme to, also from a producer, to
take the front seat and presentthe options to the client.
So thankfully I did get a lotof exposure on how to maneuver
and how to navigate aconversation with CEOs, cfos and
(35:18):
HR professionals that way.
Speaker 1 (35:20):
So you could have just grown in that role of plug
and play I'm supposed to do thistask, so I'm going to do this
task and complete it.
But you leaned in further andsaid I'm going to add strategy
to this, how can we improve whatwe're doing?
And ultimately you startedadvising the advisor.
(35:41):
Right, so the producer istechnically the advisor to the
client.
You started advising theadvisor on hey, I think you
should do this, that or theother, and because you're so
technically sound on the productand everything else, that
advisor just kind of got out ofthe way because you knew it
better and wanted you to presentthat to the client.
It's pretty fascinating.
Speaker 2 (36:02):
Yeah.
Speaker 1 (36:02):
What was that motivation like of just hey, I
just don't want to sit here andgive you the proposal, Like I
want to get involved here.
Speaker 2 (36:09):
I have been a true believer that ever since again
since I got the opportunity tocome to the U?
S that there's gotta be areason why I'm here, you know,
because it's really hard notevery day, because it's really
hard not every day, but a lot ofdays it's hard to be away from
home.
But I also think that God hasput me in this position because
(36:37):
there is a mission that I needto fulfill where I'm at, and so,
with every single job that Ihave held that is how I hold
myself accountable is am I doingthe best that I can in the
position that I have held?
That is how I hold myselfaccountable.
Is am I doing the best that Ican in the position that I have,
with the resources that I havefor the people that I work with
and I think, some people.
I remember being calledunsettled many different times
(36:57):
because I was looking to getbetter and ask for opportunities
for professional development,personal development, always
looking for that.
I'm always asking thosequestions, but it's it comes
from a place of more likeambition and wanting to continue
to be better and conduct mycalling here where I'm at today.
(37:18):
So I think that's what hasalways inspired me and motivated
me to do more than what it isasked of me is because there is
a higher calling for me here.
Speaker 1 (37:30):
That's awesome.
Well, that calling led you to aconference 2021, right, that's
where I got to meet you.
Speaker 2 (37:36):
That's right.
Speaker 1 (37:37):
So sat at the same table talk shop a little bit,
but talk about attending thatconference and then kind of what
transpired after that.
Speaker 2 (37:45):
Yeah, so, part of giving recommendations to the
producers that I was workingwith, I started getting a sense
of frustration from clients,getting a sense of frustration
from employees because of theharsh reality of our healthcare
system.
Just as ways to control costs,employers were raising
(38:07):
deductibles as a way to do soand maintain or keep costs down,
but then delivering those newsto employees was really tough.
I remember very vividly beingat employee enrollment meetings,
helping with those and havingemployees walk out because they
were so disappointed at thebenefits that were being offered
at those companies and I had tofigure there's got to be a
(38:29):
different way to do this,there's got to be a better way
to do this, and thankfully,social media was a great way to
do that.
I literally hopped on LinkedInand started following people
like Dave Chase and startedreading information about like
David Contorno, and I rememberalso following Nelson Griswold.
(38:51):
In fact, I had started to set upmeetings with him to see if I
could learn about, you know, abook that he had just come out
with, and how he was advisingand coaching agencies into a
different way of doing benefits,a better way, and so that
conference in 2021 was, I think,my first step towards saying I
(39:17):
need to become savvy on whatelse is out there and then be
able to bring that to my regionwhere I'm at today, because I
know that from a Midwestperspective.
I think a lot of the times theMidwest region is considered
kind of a late adopter ofcertain things that may be
cutting edge, that are moreearly on adopted in, like the
(39:39):
East Coast or the West Coast,and that's totally fine.
But I wanted to be one of thefirst ones to bring it to the
region.
But I needed to understand itas best as I could.
Speaker 1 (39:49):
Yeah, totally agree.
So similar story from myperspective.
Yeah, you get tired of it.
I think probably a lot of theadvisors that we've become
friends with we all have thesame like catchphrase of like
what went through our heads isthere's got to be a better way.
Like literally those exact samewords there's got to be a
better way.
This is so terrible.
This healthcare delivery modelis disgusting and you can see it
(40:13):
crushing employees that you'restanding in front of and it's
ridiculous.
But yeah, so we met at theconference and then you followed
up and you decided to come onboard at Conor Insurance and
that's been awesome.
You've done a great job.
So I'm really proud of you andwhat you've done.
This award is certainlydeserved from what I've seen.
So top five broker of the yearor, I guess, advisor of the year
(40:35):
.
That's right, I'm so old I knowit as broker of the year, but
now it's the advisor of the yeartop five across the country.
So we'll find out soon who isthe winner.
But what we really know is allfive of you are winners, because
five out of the entire countryis incredible.
So congrats to you.
Before we get into our finalquestions I wanted to get into
(40:57):
just real quick I want to askyou like you look back.
You've almost been at Connorfor three years and you've had
the experience that you've had.
What do you hope for the nextthree years in your advising
career Like?
What are your aspirations for?
What that looks like.
Speaker 2 (41:16):
That's a really good question.
I think that one of the thingsthat I still am working towards
is being able to bring change tomy backyard like that, my
community here.
You know I've been within thiscommunity for 20 years.
Actually, this year marks my20th year of being here and I
(41:37):
know so many people just becauseI went to college here and now
I have three kids that areattending, you know, local
schools here and so I'm startingto get to know the parents of
other kids that are in theirclass and it's like kind of that
saying of like loving yourneighbor.
I want to love my neighbors bybeing able to provide affordable
(42:01):
health care to them, Because Ihave been a health care user
again, had three kids, so, ofcourse, you know I had to
deliver my kids in hospital, soI understand very much how it
works now and thankfully, withConnor and having my third child
, I was able to experience abetter way of doing so and
within my community.
Speaker 1 (42:21):
So I know it's possible, I know it can be done,
and so for the next you know,three, five, 10 years, I really
want to help bring thatexcellent experience that I had
to other people in my community,Because I know, go, I'm trying,
yeah, now then in yourcommunity is lucky to have you,
(42:44):
and I'll be fun to watch themrealize that as you continue to
grow your client base in thatgreater area Cause really, like
Dubuque, is right on the borderof Wisconsin, so your market
really is Iowa, wisconsin,illinois, I mean, they're all
right there and even up inMinnesota where we have clients
already.
It's a great state.
So we have two questions thatwe ask everyone that comes on
(43:06):
the pod.
So the first question is andyou probably have several to
choose from actually what is therisk you have taken that has
changed your life?
Speaker 2 (43:16):
Oh, that's a yeah, definitely have several ones.
I think the risk that propelledeverything that I've been doing
here was the risk of coming toa different country, like that
is.
It was a hard decision at 17 toleave home.
I know it was super hard and Iunderstand it now as a parent
(43:37):
like letting your children goand pursue their dreams, but
much further, into anothercountry, another culture and a
very different setting.
It's hard, but it's also adecision that has opened so many
doors.
So many doors met fantasticpeople, being able to have some
of the best memories in my lifemeeting my husband.
(44:00):
That would have never happenedif I wouldn't have come to the
US.
We met in college, and so Ithink that just making the leap
of faith and deciding to buildmy dreams in the US has been one
of the best risks I could haveever taken.
Speaker 1 (44:16):
I think that is an absolute fascinating story of
trying to put myself in yourshoes, of being an immigrant and
going somewhere new.
And you mentioned, like 17years old, hopping on an
airplane and going to adifferent country to live and go
to school.
And there's probably severalparents, maybe even listening
right now, that like haveheartburn about their 17 year
old driving on the interstate.
(44:37):
You know like just theincredible risk.
I mean, it is an incrediblerisk, so that's awesome.
So the second question is moreabout like, maybe future dreams,
but what's unfinished for youthat you have the resolve to
complete in the near or not sonear future?
Speaker 2 (44:57):
That's an excellent question too.
I think that you know kind ofwhat I mentioned before about
being able to make an impact inmy community is so significant,
and especially because I do wantlike my kids are my motivation
every day when I wake up and goto work, even when I'm having a
(45:17):
bad day, I just think of themand think of they deserve better
healthcare experiences.
They deserve to get taken careof by high quality physicians
that have the best outcomespossible for whatever health
challenges they face, and so thework that I'm doing now, even
(45:39):
though it's one teeny tiny pieceof sand in this gigantic
behemoth of a healthcare system,I'm hopeful that it will help
make their experience better,and so I have the resolve to not
just make an impact in mycommunity, but also to help
design a better healthcaresystem for my kids.
Speaker 1 (45:59):
That's awesome.
I don't think there's a betterplace to end than that.
De Diana, thanks for joining metoday on the pod.
Congrats to you on the 2025Advisor of the Year finalist
Super well-deserved and thanksto the audience for joining us
for another episode of the Riskand Resolve pod.
(46:20):
Thanks for tuning in to Riskand Resolve.
See you next time.
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