March 19, 2025 • 40 mins
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In this episode, Bekim is joined by Shubha Dasgupta. Shubha is the Co-Founder, President, & CEO of Toronto-based Pineapple, a leading mortgage industry disruptor. Since joining the mortgage industry in 2008, Shubha has focused on leveraging technology while prioritizing customer experience to transform the sector. As an award-winning executive, his unique vision and expertise have been instrumental in building and growing Pineapple, which boasts over 700 brokers in its network today. Shubha is also a philanthropic leader who actively engages with various non-profit organizations in the Toronto community, and his reputation as a mortgage industry thought leader makes him a highly sought-after public speaker and media expert.
Shubha is here to discuss: → How his family values have shaped his business values, how there's more than one right way to get to a destination, and why they took Pineapple public. → If regulators or brokerages are responsible for a broker's mortgage education, why brokers should think like athletes, and his overall vision for elevating Canadian brokers. → The fundamental impact brokers have on the lives of Canadians, multiple ways brokers positively impact the Canadian economy, and how the broker community should be measuring success.
Pineapple Mortgage Website: www.gopineapple.com
Pineapple Mortgage LinkedIn: @PineappleMortgage
Pineapple Mortgage Instagram: @pineapplemortgage
Pineapple Mortgage YouTube: @PineappleMortgage
Shubha Dasgupta's LinkedIn: @ShubhaDasgupta
Shubha Dasgupta's Instagram: @shubs88
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Thank you for listening to thisepisode of Leading Thoughts,
(00:01):
sponsored by Rocket Pro.
Today, I'm joined by Shuba
Dasgupta, the CEO of PineappleMortgage.
We have a great conversationranging from how his family values
shaped his business values.
We talk about the importance of
helping people and helping themortgage broker industry as a
whole.
And we talk about his overall
vision for mortgage brokers andhow important what we do is to
(00:25):
this industry.
You're not going to want to miss
it.
Thanks for listening in.
Shuba, thanks for joining me.
Oh, thank you so much for having
me, man.
It's my honor.
Absolutely.
So I always like to start with the
same question, which is, can youtell us your life story in 60
(00:45):
seconds or less, please?How do you tell a life story in 60
seconds, Fakim?But yeah, give it a shot, man.
Born and raised in Toronto.
Two loving first generation
immigrant parents came here fromIndia.
I was actually raised by mygrandmother as I had two very
hardworking parents.
And my grandmother lived with me
from the time I was born.
So I had that.
very grandmotherly touch for thevery large early part of my
(01:06):
formidable years.
And around the age of 14, she was
diagnosed with cancer and passedaway, unfortunately, actually in
my arms while I held her as shetook her last breath, which was a
very pivotal moment in my life andkind of created a flurry of
emotion as well as an ability forme to see a little bit clearer
into what I wanted to do in thefuture, which was to help people.
(01:28):
And that kind of got me involvedinto cancer charities.
a lot of philanthropic work.
And it led me to the world of
entrepreneurship, where I startedmy first business at the age of
21, transportation logisticscompany, sold that business in my
mid -20s, started a biodegradablepackaging business, which
unfortunately came to an untimelyend due to another life incident,
and then got into the mortgageindustry and haven't looked back.
(01:48):
Two lovely kids along the way.
Got married in 2008.
Been with my wife for a very longtime now.
What is it?This is our 17th wedding
anniversary.
We've been together over 20 years.
Love biking, love hiking, loverunning.
And I love people.
I mean, mean, that's the way to do
it in 60 seconds.
Very well done.
There's so much to unpack there.
(02:08):
Maybe I'll start on the story that
you felt like was important, whichwas your grandmother being a
formidable part of your growing upin your life.
Now, in some ways, it sounds likeyou halfway credit a lot of your
entrepreneurship journey to thelessons that you learned through
your grandmother.
Why do you think that is?
Do you think that is a part of thegrandmother story?
Do you think that's a part of theparents' story?
(02:30):
Because you said your parents wereworking a lot too.
Yeah, I mean, I think it'sdefinitely a part of both stories.
But, you know, my grandmotherinstilled in me many of the values
that make me who I am today andtaught me many of life's lessons
that have gotten me to where I amtoday.
And along the course of myjourney, I've explored medicine as
a possible career path in my earlydays.
And I thought, hey, maybe I wantto be a doctor.
(02:52):
And after my grandmother passed,and it was right around that time
when you kind of got to make thatdecision if you're going that way,
right at 14, you got to startchoosing the courses and really
buckle down on school andeducation and that commitment
towards, you know, pursuing thatpath.
I kind of thought to myself inthat moment, you know, based on
the values that she's instilled inme.
What do I want to be a doctor for?And after some self -discovery and
(03:13):
reflection, I realized it wasn'tabout a love of medicine or
science, certainly wasn't aboutthe money or the work hours, but
it was about my desire to helppeople because that's what my
grandmother always was.
She was just, she didn't speak
English.
She came to this country and just
every step she turned, she wastrying to help somebody, help
another immigrant, help, you know,a neighbor, help a student
(03:35):
classmate that I might have.
had a relationship with.
And I realized that you can helppeople in so many other ways.
And that's what kind of led me tobusiness.
Because if you really think aboutit, that's what businesses are all
about.
Businesses are about helping
people and fixing problems withsolutions, right?
So yeah, I do believe thatalthough she's not an
entrepreneur, and neither one ofmy parents were, that it was that
(03:58):
life lesson of helping that kindof guided me towards
entrepreneurship.
Yeah.
So why transportation logistics asa starter?
You said you got into that whenyou were 21 years old.
Did you fall into that?Was it a passion?
No, I think everything in lifehappens by accident for the most
part for me anyways.
You know, the same reason why
we're all here in the mortgagespace is never because we planned
(04:20):
for it.
It just kind of fell into it by
accident.
But the same with transportation
logistics.
So my dad started his career.
My dad's an accountant and hestarted his career with Sony Music
where he spent basically his life.
He spent over 20 years at Sony
Music as an accountant in the 90s.
You know, difficult times,
difficult economy.
change in leadership caused him to
(04:41):
lose his job.
And the next job he got was with
Loomis, the armored car company,but also a very big courier
company and transportationcompany.
So he was working there as anaccountant.
And in the summers, I would go andhelp out summer jobs.
I would spend time at Loomis.
I was understanding kind of
logistics back end.
I was working, you know, right at
(05:02):
the front level with the driversand the delivery people.
So I got to see it from a lot ofdifferent aspects.
And I began to really understandthe importance of logistics, which
I think the whole world takes forgranted.
I mean, you know, food.
our table goods in our stores
clothes on our back like it allcomes from this world of
transportation and logistics and ithought it was just so interesting
(05:24):
and such an impactful way to makea difference in the world and
contribute back to the world soYeah, I kind of fell into it by
accident.
And, you know, with that
entrepreneurial spirit, I waslike, well, if I'm going to do it,
I'm going to do it on my own.
I'm going to make it better.
And I'm going to improve some ofthe challenges that I saw along
the course of my time working inthat industry.
(05:46):
And that's how it all started andstarted small.
You know, we had a couple oftrucks and we had a couple of
facilities.
And so I remember the early days
of that business.
My partner would drop me off in
industrial areas, Toronto,Markham.
you know, Richmond Hill areas.
And he would just kind of drop me
off there.
And I would spend the day knocking
on bay doors and, you know,knocking on companies' doors and
saying, hey, do you guys need anyhelp with your transportation
logistics?And like every business, you know,
(06:08):
people say no more often than theysay yes.
It just took that one.
Right.
And that first person that saidyes.
And, you know, we started shippinggoods for Zeller's stores across
southern Ontario.
And then we got some GM contracts
and we're shipping car parts intoDetroit.
Then we got this Disney Worldcontract and we're shipping baked
goods into Florida.
And then from Florida, we started
picking citrus fruit back up andshipping it into Ontario.
And then it just kind of turnedinto something special.
(06:29):
And along the course of that, Irealized that.
Maybe it was a little too earlyfor me in my life just to be in
that business, in that industry.
It's a tough place, man.
There's a dark side to it.
It was just a grind.
And I learned that I probablydidn't have the level of maturity,
experience or knowledge that Ineeded to probably get to the next
(06:50):
level.
So kind of made a wide decision.
My partner was much moreexperienced in it.
He had a lot more experience andmaturity.
So I said, hey, listen, like maybeit's time for me to find another
path in my career.
try some new things.
I'm still in my 20s and heappreciated that and bought me
out.
So, you know, made a bit of money
along the way, learned a lot oflessons, failed a lot, which is
(07:13):
very helpful and on to the next.
Yeah.
So you have a middle in there andthen you find your way into the
mortgage business.
How did you discover the mortgage
business?Where did you start at and what
has it evolved into today?You know, like the transportation
logistics, you know, by accident.
So the middle portion was actually
very critical to finding my wayinto the mortgage space.
In the middle section, kind of inbetween that business and getting
(07:35):
into the mortgage space, I kind ofnavigated a few different
opportunities, spent some time inLondon, England, lived there for a
little bit, where I learned thatbusiness is global and I learned
that opportunity is global.
But I began to kind of... see
things, look at things from adifferent light.
And I always used to like to lookahead and, you know, not what did
the world need today, but whatwill the world or what might the
(07:59):
world need tomorrow or what mightpeople need tomorrow?
And that kind of led me to thisworld of biodegradable packaging
back in 2006.
And I thought that, hey, you know
what, this might be a really coolway to help.
the world, help Earth.
You know, we have this problem or
this potential huge problem comingon the horizon with plastics and
packaging.
And, you know, I wasn't obviously
(08:20):
prepared for how big the world ofconsumerism would become through
online at that time.
That wasn't the topic of
conversation so much, but thelevel of biodegradable discussions
were just starting to boil to thesurface.
So I thought, hey, let me getinvolved in something that I had a
passion for.
So I had a... manufacturing
process out of India, where we'reconverting a fiber into 100 %
sustainable biodegradablepackaging product, almost like
polypropylene, like a plastickylike material, but it was made out
(08:43):
of a natural fiber.
Right about the time I was getting
ready to sign a distribution dealfor North America, my mom got into
a life threatening car accident.
And very similar to, you know, how
my grandmother's moment waspivotal in my life journey.
This moment with my mom was aswell, because I had to make a
choice at that time on caring formy mother or caring for my
(09:06):
business.
And to me, there wasn't really a
decision to make.
My mom was on life support.
I stayed by her bedside for 18days.
We nursed her back to health,incredible hospital and care
system here, saved her life.
And, you know, we were able to get
her back to where she needed tobe.
And during that time, theopportunity in that business had
passed, unfortunately.
So when I was looking for the next
(09:28):
opportunity, like accidents, I wastalking to a family member very
shortly after.
He was just asking me, hey, what
are you going to do next in yourcareer, in your business, in your
life?And I said, I don't know.
And he said, hey, you ever thoughtabout the mortgage business?
And, you know, my background ofeducation is actually in
(09:48):
economics, love real estate,always have as a side passion,
never thought it would become.
kind of the full -time passion.
And I took a look at it and I waslike, you know, I can get in love
with this and I can change thelives of a lot of people doing
this.
And it was like a month later I
was in and here we are, man, 17years later.
(10:09):
Man, when you jump, you leave, eh?You just go right in and figure it
out.
In my life, I don't think there's
any other way.
I think if you're going to do
something, you just go for it,man.
And, you know, you're going tolearn along the way.
figure it out.
Yeah, that's fantastic.
So when you say you got into themortgage business, how did that
start?Did you start as a mortgage agent?
Started as a broker, you know, atthat time, I wanted to learn at
(10:34):
least one of the lessons that Ilearned from my time running the
transportation logistics businesswas that You know, coming in with
a little knowledge is going to setyou back a lot more than coming in
with a little more knowledge.
So I wanted to make sure that I
can come in as knowledgeable aspossible.
So I took the broker course, whichat the time was very robust.
It was a year long.
We had to do a two month
internship stint in the middle ofthat year long full time course,
by the way, was like a nine tofive, 16 university credits.
(10:56):
It was offered here through Senecavia the University of British
Columbia.
So we learned a lot.
I mean, we learned about realestate law.
We learned about fundamentals.
We learned about economics.
We learned about appraisals.
We learned about real estate math
and mortgage math right down toits core.
Learned about securitization ofloans and how, you know, mortgages
are really structured here inCanada.
And I thought that knowledge wasvery helpful to me in the early
(11:17):
part of my career until I got intothe business.
Then I quickly learned that itdoesn't matter how much you know
when you don't have anyone toshare it with.
So I learned that all of thattechnical knowledge that I had
gained coming into this industry,which I thought was going to be
very helpful and has beenthroughout various aspects of my
career path.
But I learned a hard lesson on day
one, which is it doesn't matter ifthere's no one in front of you.
(11:38):
So I quickly started to educatemyself on people, sales,
marketing, you know, all thosethings that I had kind of done
naturally in other businesseswithout having fundamental
knowledge, but became very wellversed in those areas.
And now I like to think of myselfmore as a sales and marketing
executive than a mortgageexecutive.
Yeah, that's really interesting tothink about that story that way.
There's a lot of talk in ourindustry these days that, you
(12:00):
know, a lot of agents just simplyaren't educated enough to be
advising consumers.
I see those conversations from
time to time.
And obviously, getting a license
today is much easier than it wasback then.
So do you think that we shouldlive in a world where mortgage
agents have to spend significantlymore time, energy, money to get
into the business the way that youdid?
Is the most important thing justgetting in, starting to talk to
(12:22):
people and learning while doingessentially?
I'll give you a couple ofdifferent perspectives on it, a
couple of different perspectiveson it, and then I'll give you my
answer.
When we started this company, I
was very challenged as to why theregulatory requirements had
changed so much.
And people were coming into this
industry and coming into thisbusiness with very little
knowledge about.
both like mortgages and people
like very little knowledge aboutfundamental mortgage rules and
(12:42):
information that they probablyneed to know in order to help
their clients make the bestdecisions.
But also on the flip side, like,you know, inability to communicate
and articulate complex informationthat we work with on a very daily
basis.
So I was kind of struggling with
that.
So I did a lot of kind of
reflection as to like, why wouldthe industry do this?
Like, why would the regulatorswant to make it easier versus?
(13:04):
is harder.
Obviously, I don't have the end
answer to this because it wasn'tme who made that decision.
But when I thought about it, Ithought, you know what, look, the
country is growing, the economy isgrowing, and the need for this
industry is growing.
The need for what we do as
mortgage agents, as brokers, assolution providers, the Canadians
(13:24):
was growing as our population was,and the need for housing became
more required.
So I thought to myself, okay, you
know what, maybe it's not a badthing that we have more people in
this industry because these peopleneed to help Canadians.
It all came back to helping,right?
We need to help Canadians achievetheir dreams of homeownership, put
(13:47):
a roof over their head, helpcreate that security where they
can raise a family, where they canfeel safe, where they can build
financial wealth through investingand other home buying strategies
or other real estate strategies.
Then it became, OK, maybe it's
justified, but what do we do?Because you do need that
knowledge.
So then as an industry, we have to
get better at raising the bar oninternal education and providing
(14:07):
the resources and the knowledge tothe agents as they're coming in to
make sure that the correctinformation is being articulated.
Now, I said I was going to give acouple of different perspectives.
The other perspective is, andsomething I believe very heavily
in, is I believe in the gym and Ibelieve in.
game time.
And I always use the analogy of
athletes when I give this example.
Athletes don't go into game time.
(14:28):
not taking that three -point shot100 times or not taking that free
throw 100 times in the gym.
They're in there practicing plays.
They're in there practicing whathappens in various circumstances
and situations.
Let's take, for our purposes, call
that objection handling, maybe.
They're going through different
scenarios multiple times in thegym before the game ever happens.
They're strengthening muscles.
They're strengthening endurance.
They're watching film.
So do we do enough of the gym
(14:51):
time?question in the mortgage industry
because game time is when there'sa client in front of you you don't
have the ability to practice on aclient it's not fair to the client
it's not fair to you it's not fairto your business so where is the
gym is really the question so thegym could be in the classroom It
could be through more regulatoryrequirements of education, or it
(15:15):
could be on raising the bar ofwhat brokerages and organizations
like ours have to do to supportthe people that, you know, in the
end work for them and provideguidance based on the solutions
that they have to offer asorganizations.
So I think one way or another,Vakim, there needs to be a higher
bar of education.
I'm not.
certain on whether it needs to befrom the regulators forcing it
(15:37):
upon people or just raising thebar of what we need to do as
leaders in this industry, which ispart of the reason why we ended up
where we are and big supporters ofeducation here.
So how does Pineapple Today, whichyou're the leader and CEO of,
build its business aroundeducation, training, coaching?
Because it's my understanding thatyou guys put a lot of effort and
(16:01):
energy into A lot of timesbringing in agents who are very
new to the business and helpingthem become professional mortgage
agents.
Obviously, it's not as regulated
as it could be.
So it falls back on the brokerage.
How does Pineapple handle that?You know, from our perspective,
like what we did and what wealways ask ourselves is, what is
the purpose and what is theintent?
(16:21):
Anytime we're going to try totackle a problem, right?
And then you kind of begin toreally realize and dive into the
core of, you know, what theproblem is and how your solutions
are going to aid in that problem.
So when we asked ourselves purpose
and intent, you know, purpose,obviously, to support the
regulatory framework and, youknow, let's call it lack of maybe
(16:44):
necessary education that amortgage agent needs to be able to
properly serve the needs ofCanadians.
And the intent is.
Obviously, coming back to help,
helping mortgage agents andbrokers build more robust, strong
businesses, helping mortgagebrokers and agents provide more
accurate and knowledgeableguidance towards the Canadian
consumers.
And in the end, helping Canadian
consumers achieve their dreams ofhomeownership while building a
stable and strong economic fabric.
As we both know, the home buying
and real estate market in Canadaplays a significant role in the
(17:09):
strength of our overall economy.
So then when we kind of really
realized that, so we began tobuild it into everything that we
did.
So, you know, training for us
transcends beyond just training,you know, which we have a lot of.
We have, you know, live training.
We have recorded sessions.
(17:30):
We have an LMS platform that webuilt.
I will call that more likefundamental training.
But then let's take training astep beyond, right?
So, you know, when we built ourunderwriting department, internal
processing, which most brokerageshave, you know.
Training got layered into thatbecause what we believed was that
new mortgage agents coming in thatmaybe lacked the experience to be
able to provide solutions to theirclients needed a resource to be
(17:51):
able to get that guidance.
And then when we built our
systems, we built it withvisibility so that our agents
could see what our underwriterswere doing, back and forth
conversations with the lenders,document collection with the...
So they were seeing, hey, whatquestions are they asking?
What problems are they tackling?Why is this being asked?
So they were kind of learning asthey were going through the
(18:13):
process without impacting thecustomer in game time.
Right.
Very similar to like marketing.
You know, a lot of our marketingcommunications, we do a lot of
internal marketing on behalf ofour agents out to their consumers
and provide knowledge andeducation.
But before a marketingcommunication goes out, we
actually educate the agent on thatcommunication.
(18:34):
So if we're going to talk about aspecific item, let's just say
hypothetically we're going to talkabout the role of tariffs on
interest rate fluctuation, then wewill make sure that our agents are
educated on that topic prior tothat communication going out.
So they have talking points andthey have the ability to discuss
it when the reaction comes in,right?
And the reaction is responses tothose emails with questions about
(18:54):
that subject matter.
So we began to see that training
had to transcend.
just training as a pillar of our
company and have an impact or havea touch point in every aspect of
everything we did.
So that's where we built like
agent onboarding.
That's where we built succession
planning and how to elevate yourcareer to become a team leader,
(19:16):
eventually become a broker owner,if that's the succession plan or
if that's the path that you're on,how to navigate various aspects
from technical to sales andmarketing to maybe even
philanthropy, which we have.
actually talk a lot about giving
back to the community and how toserve them, right?
So it became this whole robuststructure that evolved into every
aspect of our business focused oneducating, whether large or small,
(19:38):
like whether we're teaching youabout one thing through an email
that's going out or through awhole program through a two -hour
session or even a whole path ofyour career through a five -week.
course, right?It just became a part of who we
are is the short answer.
Yeah.
I'm curious of how much of whatyou are today was part of the
original vision versus how muchhas been an evolution as you've
(20:01):
had to pivot, adjust, remakeourselves in this industry.
When you think back to the earlydays of starting Pineapple, to
where you are now, what do youthink was your truest assumption
in hindsight?And what do you think was maybe a
false assumption in hindsightcompared to what you are now?
I think what a lot of people maybeforget or don't think about as
often, maybe they don't forget, isthat there's more than one right
(20:23):
way to get to that destination.
You know, if I'm coming to visit
you right now, you know, I cantake the 401.
There might be a truck flippedover.
There might be bad weather and Ican detour.
And I can take a side road.
I can stop and wait.
I can rest and sleep for thenight.
(20:44):
There's more than one way for meto get to that same destination.
And that's what's happened hereover my time at Pineapple.
We've come to learn that the goalhas always been the same.
But the way that we're going toget there has evolved and changed
significantly year to year, monthto month, sometimes even day to
day, right?But the goal has been fundamental,
right?We started this business on the
(21:06):
premise of we want to give back tothe community of mortgage
brokering.
We want to make sure that we are
helping mortgage brokers andagents build strong, successful
businesses that they are then inturn to translate to their
consumers and helping consumersbuild strong, you know, real
estate portfolios or real estatejourneys.
And it started with three pillarsof support, training and culture.
(21:28):
And today, those three pillarsstill live.
all rounded out throughtechnology, but they still live
very strong.
And although maybe not the same
road that we had envisioned fromday one, maybe not just a straight
shot on the 401, but we hitdetours, right?
We hit obstacles, we hit trucksflipped over, we hit bad weather,
we hit flat tires, we ran out ofgas.
(21:52):
And we just had to find solutionsto those problems and realize,
hey, if we stay focused on the endgoal, which is to uplift our
industry, then we'll still be ableto get there by taking detours and
different routes.
So I think that we're right on
course to where we had to be, butprobably not just on the same road
that we thought we would havebeen.
I like that analogy.
(22:13):
I wonder how much of that comes
from your background in logistics.
I guess part of your journey that
makes folks curious is goingpublic as an organization, which
is a rarity in the mortgage world,but you guys did that.
Was that a part of the originaljourney or was that another one of
these sort of detours that helpsyou get to the eventual
destination and just a part of theoverall journey and story?
(22:37):
Yeah, that was definitely adetour.
You know, it wasn't in thebusiness plan on day one that we
said, hey, you know what, let'sbuild a company, grow it to a
stage, raise some capital, take itpublic, IPO, you know, all those
kind of things, as some businessesdo very successfully.
For us, it was more of stayingtrue to our goal.
And as we got to a point, and Iremember the point, it was in and
(22:59):
around 2020, where we hadrealized, hey, you know what?
We're funding just around abillion dollars a year in
mortgages.
We're growing at an incredibly
fast rate.
We had wonderful user adoption and
feedback for the solutions and thetools and the resources that we
were providing.
We had a great culture, but we
were only operational in Ontarioat that time.
(23:22):
And we said to ourselves, we said,hey, listen, we have something
special here.
Maybe it's time.
Maybe it's time for us to put ourfoot to the gas and see if we can
accelerate this across Canada andreally leave a lasting footprint
on the industry and on the market.
So that's when we decided in order
for us to do that, we had to raisesome capital.
(23:44):
We could have continued to go theorganic path, which we had done
for the first four years of thebusiness, completely bootstrapped,
completely profitable and growingat an incredible pace.
But we said, well, hey, look, wehave a moment in time right now.
We have an opportunity where wecan accelerate and where we might
be able to do something reallyspecial that we otherwise would
not have been able to do.
So we raised our first round of
capital, which closed in 2021, $9.3 million.
(24:07):
And with that, began to tackle.
those goals.
So we expanded nationally today,represented in every province.
You know, we doubled our agentcount.
Well, actually, we tripled ouragent count now since that initial
moment.
We've almost tripled our funded
volume.
So we started to do the things
that we set out to do.
But when we took in that capital,
we did realize that when you bringshareholders in and when people
(24:28):
invest in your business, you haveto give them a clear path and you
have to give them a path ofliquidity at some point in time.
And going public for us was acouple of different reasons.
I don't know if anybody's everasked me publicly the reasons, so
I appreciate you asking.
Part of it was industry related
and part of it was businessrelated.
From an industry -relatedperspective, which is very
(24:50):
important to me and somethingthat's often not talked about, was
that we wanted to elevate thisbrand of Canadian mortgage broker.
We wanted to be able to show theworld the impact that mortgage
brokers have on Canadians, notjust like a Canadian buying a home
and being able to source a propermortgage rate or the right
solution to meet their needs.
That, for sure.
(25:10):
But beyond that, the impact thatmortgage brokers play in the
overall economic landscape andhealth of Canada, like how
impactful are we that we helpconstruction financing and
development and people along thejourney of their home buying?
We help people with refinances anddebt consolidations.
We help with commercial financingand help funding all of these, you
know, now large scale logisticscenters like Amazon and other big
distribution hubs that have becomesynonymous with.
(25:31):
you know, the landscape ofdistribution and with, you know,
goods and services getting intothe hands of Canadians.
Well, I mean, a lot of it startsright here in this industry.
And we wanted to elevate.
what we do as mortgage brokers i
don't think that canadian mortgagebrokers because we didn't have as
much market share as u s mortgage brokers or european
mortgage brokers or australianmortgage brokers at that time you
(25:52):
know we're often an underthoughtright you think of mortgages and
you think about the bank but no wehave an incredibly vibrant
community here and we wanted toshowcase that so that was a big
reason why we took this step.
We did it on behalf of all of us
to be able to raise the brandequity of what we all do as an
(26:15):
industry.
And the second part of it was
business related.
The second part of it was access
to public treasuries, access tocapital, which helps our business
grow, helps our business continueto have the funding requirements
that we need to run deficitbudgets or non -deficit budgets,
depending on what our goals are orwhat our objectives are at that
time.
allows our shareholders to have
liquidity options so if you wantto invest into the business you
(26:36):
know how you're going to get outversus a private buyout so there's
the business side of it and thenthere's the industry side of it
and both of those converged intous making the decision to do it
and we knew we were going to do itwith tough times ahead for certain
aspects of it, but we knew thatcertain aspects of it were going
(26:58):
to be great.
It's a catch -22, right?
There's no right decision ever.
There's the decision that makes
the best sense for you, yourorganization, and your company.
And we felt that that was theright decision for us, and we
still do today.
That was going to be my next
question, was the hindsight biasaround this, which is looking back
(27:19):
and trying to make the decision,was this the right thing to do?
for you as an organization.
So it sounds like you answered
that.
I do want to ask you, how does
being a public company and being apublic CEO change the way the
company operates?Does it have any effect at all
(27:40):
other than obviously the reportingneeds of being such a business?
Or is it much the same in terms ofthe operations and the goals?
I remember when we started thisjourney.
to do an IPO.
And, you know, obviously an IPO
involves a lot of external supportfrom bankers and underwriters,
like capital market securitiesunderwriters, lawyers and
auditors.
There's so many people involved in
this process.
And one consistent in that journey
(28:02):
was that when we met withsomebody, they always said, you
guys are a private company runningas a public business.
And, you know, I didn't fullyunderstand what they meant at the
time because I've never been apublic company.
executive until now, but I beganto learn as I became public.
And that was, you know, withopenness and transparency and
organizational reporting andcorporate governance and, you
know, all of those things that Ithink all great businesses have,
(28:23):
whether by accident or by design.
And, you know, some of ours was by
accident, some of it by design,but we were always running our
business with.
high regard for the people
involved in it.
So we didn't start the business as
pineapple.
But in the early days of our
company, we had a saying where,you know, when a mortgage agent
(28:44):
and broker entrusts us withsomething as valuable as their
career, we have the responsibilityto treat it with the utmost
respect.
And every single day, we'd all
come into work, all of us, myselfincluded, all of our staff, all of
our employees, and we would holdourselves to that standard that We
work on behalf of all of thesepeople, hundreds of people that
trust us with the greatest gift.
Like, I mean, you know, this is
(29:05):
their career.
This is how they pay their bills.
This is how they feed theirfamilies.
And we have a responsibility totreat it with that respect.
And that responsibility is whatled us to the governance and to
the transparency and to theopenness, some by accident, some
by design, but then led us to theIPO.
In some ways, sure, the businesshas changed, you know, a lot more
reporting, a lot more shareholderengagement, different calls for me
(29:27):
sometimes throughout the day thanwhat I was used to.
But in some ways, the business hasjust always kind of been running
this way, right, where we justwanted to run a really proper,
ethical, organized company.
Well said.
So there was something you saidearlier I want to go back to,
which was about elevating themortgage broker in Canada
specifically.
And I'm curious, this is something
(29:47):
I think about often.
I had the privilege of watching
that journey transpire throughoutthe United States.
I mean, at one point, mortgagebrokers were a huge part of the
market.
You have the crash, mortgage
brokers, a lot of them just getout of the industry entirely.
And then you had the period fromroughly, I want to say 2014 to
(30:08):
today where mortgage brokers arethriving over there.
able to do.
Even in the time that I've been
operating in the Canadian marketgoing back to 2020 now, I think we
went from 20 % to roughly 40 %mortgage broker market share.
And that number fluctuatesdepending on the number of
renewals going on at any giventime.
And of course, rates play afactor.
But one thing I've often talkedabout is we don't have a got milk
(30:34):
question mark for Canadianmortgage brokers.
Like there is no trueorganizational structure, and it
feels very siloed in the mortgagebroker community.
And I don't think the publicunderstands the true value of
mortgage brokers.
So when you say that, I get
excited.
But I do also question for myself
sometimes, and I want to pose itto you, which is like, how do we
measure success outside ofmortgage broker market share in
(30:56):
this industry for mortgage brokerssuch that we can elevate the
entire broker community?Such a great way to think about
it, right?Because, you know, we often think
about like market share or revenueor volume as kind of, you know,
the key indicator, right, ofsuccess of what anybody does.
But as we all know, like there'sso many more layers and there's so
much more that goes into it.
I think one of the things that is
(31:19):
often not talked about is, youknow, what you just shared about
just the elevation of marketshare.
And I know that's not the specificquestion, but I just want to touch
on it quickly.
So, yeah, we went from 20 percent
to 40 percent.
We peaked over 50 % at a certain
point a couple of years ago.
We've kind of dipped back below.
But I'm very certain that we willbe in and around that 60%, 70 %
(31:44):
range within the next few years.
And I don't know exactly what the
next few years means, whether it'sone year, two year or five years.
But I think within that next nearfuture, mortgage brokers certainly
do have the majority market share.
But what does that then mean,
right?And what does that mean to what
we're talking about?Well, now we're talking about how
(32:04):
many Canadian small businessowners that are now contributing
back to the economy.
in multiple different ways.
So how many mortgage brokers do weknow that hire multiple assistants
and social media managers andmarketing firms and sales managers
and, you know, infrastructuralsupport, admin teams, payroll,
compliance that are needed tooperate these businesses?
So now we have small businessesthat turn into, you know,
(32:25):
employers and, you know, what weresolo entrepreneurs are now
funding, you know, tax dollarsback into the economy.
They're funding other ways ofsupporting Canadian job growth and
other ways of us kind of givingback towards what I referred to as
this economic fabric.
So I think that's one way of
looking at the success of it.
(32:46):
I think another way of looking at
the success of it is...
The fundamental impact that we
have on the lives of Canadians.
And, you know, I always talk about
my parents as immigrants cominginto this country and leaving
their homeland in search of betteropportunity for us.
And the responsibility that wehave that I believe I have as kind
of this next generation, firstgeneration born son of immigrants.
(33:14):
I believe that if they lefteverything behind for more
opportunity for me, I better seesome of that opportunity and kind
of do everything I can in mypower.
to achieve that for them becausethey sacrificed a lot.
The reason I bring that up is howbig a part was that dream of
homeownership for them?And how big a part was that
(33:35):
ability to have a roof?A safe roof, let me refer to that
actually, a safe roof over theirfamily's head.
Because a lot of people that comeinto this country, which sometimes
we take for granted, might have aroof over their head where they
come from, but it's not safe forthem.
Or they don't feel it's a placewhere they feel safe and secure,
where they can raise their kidswith freedom and expression and
(33:56):
happiness and memories andlaughter and tears and all of
those things that we remember whenwe think about our time in our
homes.
I think that's another way to
measure success is like when welook at, you know, my parents that
bought their first home in the 80sfor.
less than $100 ,000 and recentlydownsized and sold it for over a
million.
That ability for them to find
financial success, but not justfinancial success, they found life
success.
They raised their kids.
(34:16):
My grandmother passed away in thathome.
That's where I held her in myarms.
Like that was a safe place forher.
So where I learned to ride mybike, it's where I came when I
proposed to my wife.
It's where my daughter was born
when my house was being built andI had nowhere to go.
And my parents said, come stay.
My daughter was raised her first
year in that house amongst hergrandparents.
(34:38):
I think there's so many ways forus to think about success in life
outside of just dollars and centsand volume and revenue.
And I think that's what themortgage broker industry.
for me anyways, needs to elevateis that impact that we have, the
impact on the lives of otherbrokers, on the lives of our
(35:02):
staff, of our employees, of ouragents, of Canadians that we
impact every single day.
And if we take their money aside
for a second, I think that we areincredibly successful as an
industry in what we achieve andwhat we accomplish.
That's really well said.
And I couldn't agree more when I
think about the impact thatmortgage brokers have on
(35:24):
homeownership as a child ofimmigrants myself, being able to
own a home in the West and raise afamily around that compared to
other parts of the world.
It's just an incredible impact
that we get to make.
So I want to wrap up by just
asking you about impact.
what you want to build when you
you know jump out of bed every dayand presumably you're somebody who
(35:44):
leaps out with a bit of enthusiasmgiven how much you talk about
helping people and helping theindustry as a whole what do you
want your impact to be on thismortgage industry So truthfully
for me, I have a great admirationfor those that came before me.
And I think that we are all aproduct of our predecessors, just
as other companies and otherindividuals and other people have
(36:07):
laid groundwork for companies likeours to be able to thrive and
succeed and build off of andimprove.
What I hope is to leave that samepath.
I hope to be able to leavesomething.
and help others realize that theyare the future of this industry
and they can pick up where we leftoff and they can take what we've
done and improve upon it and fixit and make it their own.
(36:28):
And I think if we all have thatnatural insight that generations
will continue to progress and ourjob as an industry today in the
generation that we live is to takefrom our predecessors and give to
our successors.
then I'd be happy.
So that's the impact I want toleave.
I want to be able to leave mysuccessors something that they can
take and run the ball with andmake it their own and make it
(36:50):
bigger and better than I couldhave ever dreamed of and imagined.
Yep, totally get it.
We have been past the torch and we
will have to pass that torch.
And that's really well said.
So thank you for joining me today,Shuba.
Keep up the fantastic work withyou and your team at Pineapple and
keep pushing this industryforward.
(37:10):
It's greatly appreciated.
The honor has been mine, man.
And, you know, I have greatadmiration for you and so many
other colleagues around thisspace.
So I say the same to you as wellas our peers.
Thank you.
Thank you for listening to thisepisode of Leading Thoughts,
(00:01):
sponsored by Rocket Pro.
Today, I'm joined by Shuba
Dasgupta, the CEO of PineappleMortgage.
We have a great conversationranging from how his family values
shaped his business values.
We talk about the importance of
helping people and helping themortgage broker industry as a
whole.
And we talk about his overall
vision for mortgage brokers andhow important what we do is to
(00:25):
this industry.
You're not going to want to miss
it.
Thanks for listening in.
Shuba, thanks for joining me.
Oh, thank you so much for having
me, man.
It's my honor.
Absolutely.
So I always like to start with the
same question, which is, can youtell us your life story in 60
(00:45):
seconds or less, please?How do you tell a life story in 60
seconds, Fakim?But yeah, give it a shot, man.
Born and raised in Toronto.
Two loving first generation
immigrant parents came here fromIndia.
I was actually raised by mygrandmother as I had two very
hardworking parents.
And my grandmother lived with me
from the time I was born.
So I had that.
very grandmotherly touch for thevery large early part of my
(01:06):
formidable years.
And around the age of 14, she was
diagnosed with cancer and passedaway, unfortunately, actually in
my arms while I held her as shetook her last breath, which was a
very pivotal moment in my life andkind of created a flurry of
emotion as well as an ability forme to see a little bit clearer
into what I wanted to do in thefuture, which was to help people.
(01:28):
And that kind of got me involvedinto cancer charities.
a lot of philanthropic work.
And it led me to the world of
entrepreneurship, where I startedmy first business at the age of
21, transportation logisticscompany, sold that business in my
mid -20s, started a biodegradablepackaging business, which
unfortunately came to an untimelyend due to another life incident,
and then got into the mortgageindustry and haven't looked back.
(01:48):
Two lovely kids along the way.
Got married in 2008.
Been with my wife for a very longtime now.
What is it?This is our 17th wedding
anniversary.
We've been together over 20 years.
Love biking, love hiking, loverunning.
And I love people.
I mean, mean, that's the way to do
it in 60 seconds.
Very well done.
There's so much to unpack there.
(02:08):
Maybe I'll start on the story that
you felt like was important, whichwas your grandmother being a
formidable part of your growing upin your life.
Now, in some ways, it sounds likeyou halfway credit a lot of your
entrepreneurship journey to thelessons that you learned through
your grandmother.
Why do you think that is?
Do you think that is a part of thegrandmother story?
Do you think that's a part of theparents' story?
(02:30):
Because you said your parents wereworking a lot too.
Yeah, I mean, I think it'sdefinitely a part of both stories.
But, you know, my grandmotherinstilled in me many of the values
that make me who I am today andtaught me many of life's lessons
that have gotten me to where I amtoday.
And along the course of myjourney, I've explored medicine as
a possible career path in my earlydays.
And I thought, hey, maybe I wantto be a doctor.
(02:52):
And after my grandmother passed,and it was right around that time
when you kind of got to make thatdecision if you're going that way,
right at 14, you got to startchoosing the courses and really
buckle down on school andeducation and that commitment
towards, you know, pursuing thatpath.
I kind of thought to myself inthat moment, you know, based on
the values that she's instilled inme.
What do I want to be a doctor for?And after some self -discovery and
(03:13):
reflection, I realized it wasn'tabout a love of medicine or
science, certainly wasn't aboutthe money or the work hours, but
it was about my desire to helppeople because that's what my
grandmother always was.
She was just, she didn't speak
English.
She came to this country and just
every step she turned, she wastrying to help somebody, help
another immigrant, help, you know,a neighbor, help a student
(03:35):
classmate that I might have.
had a relationship with.
And I realized that you can helppeople in so many other ways.
And that's what kind of led me tobusiness.
Because if you really think aboutit, that's what businesses are all
about.
Businesses are about helping
people and fixing problems withsolutions, right?
So yeah, I do believe thatalthough she's not an
entrepreneur, and neither one ofmy parents were, that it was that
(03:58):
life lesson of helping that kindof guided me towards
entrepreneurship.
Yeah.
So why transportation logistics asa starter?
You said you got into that whenyou were 21 years old.
Did you fall into that?Was it a passion?
No, I think everything in lifehappens by accident for the most
part for me anyways.
You know, the same reason why
we're all here in the mortgagespace is never because we planned
(04:20):
for it.
It just kind of fell into it by
accident.
But the same with transportation
logistics.
So my dad started his career.
My dad's an accountant and hestarted his career with Sony Music
where he spent basically his life.
He spent over 20 years at Sony
Music as an accountant in the 90s.
You know, difficult times,
difficult economy.
change in leadership caused him to
(04:41):
lose his job.
And the next job he got was with
Loomis, the armored car company,but also a very big courier
company and transportationcompany.
So he was working there as anaccountant.
And in the summers, I would go andhelp out summer jobs.
I would spend time at Loomis.
I was understanding kind of
logistics back end.
I was working, you know, right at
(05:02):
the front level with the driversand the delivery people.
So I got to see it from a lot ofdifferent aspects.
And I began to really understandthe importance of logistics, which
I think the whole world takes forgranted.
I mean, you know, food.
our table goods in our stores
clothes on our back like it allcomes from this world of
transportation and logistics and ithought it was just so interesting
(05:24):
and such an impactful way to makea difference in the world and
contribute back to the world soYeah, I kind of fell into it by
accident.
And, you know, with that
entrepreneurial spirit, I waslike, well, if I'm going to do it,
I'm going to do it on my own.
I'm going to make it better.
And I'm going to improve some ofthe challenges that I saw along
the course of my time working inthat industry.
(05:46):
And that's how it all started andstarted small.
You know, we had a couple oftrucks and we had a couple of
facilities.
And so I remember the early days
of that business.
My partner would drop me off in
industrial areas, Toronto,Markham.
you know, Richmond Hill areas.
And he would just kind of drop me
off there.
And I would spend the day knocking
on bay doors and, you know,knocking on companies' doors and
saying, hey, do you guys need anyhelp with your transportation
logistics?And like every business, you know,
(06:08):
people say no more often than theysay yes.
It just took that one.
Right.
And that first person that saidyes.
And, you know, we started shippinggoods for Zeller's stores across
southern Ontario.
And then we got some GM contracts
and we're shipping car parts intoDetroit.
Then we got this Disney Worldcontract and we're shipping baked
goods into Florida.
And then from Florida, we started
picking citrus fruit back up andshipping it into Ontario.
And then it just kind of turnedinto something special.
(06:29):
And along the course of that, Irealized that.
Maybe it was a little too earlyfor me in my life just to be in
that business, in that industry.
It's a tough place, man.
There's a dark side to it.
It was just a grind.
And I learned that I probablydidn't have the level of maturity,
experience or knowledge that Ineeded to probably get to the next
(06:50):
level.
So kind of made a wide decision.
My partner was much moreexperienced in it.
He had a lot more experience andmaturity.
So I said, hey, listen, like maybeit's time for me to find another
path in my career.
try some new things.
I'm still in my 20s and heappreciated that and bought me
out.
So, you know, made a bit of money
along the way, learned a lot oflessons, failed a lot, which is
(07:13):
very helpful and on to the next.
Yeah.
So you have a middle in there andthen you find your way into the
mortgage business.
How did you discover the mortgage
business?Where did you start at and what
has it evolved into today?You know, like the transportation
logistics, you know, by accident.
So the middle portion was actually
very critical to finding my wayinto the mortgage space.
In the middle section, kind of inbetween that business and getting
(07:35):
into the mortgage space, I kind ofnavigated a few different
opportunities, spent some time inLondon, England, lived there for a
little bit, where I learned thatbusiness is global and I learned
that opportunity is global.
But I began to kind of... see
things, look at things from adifferent light.
And I always used to like to lookahead and, you know, not what did
the world need today, but whatwill the world or what might the
(07:59):
world need tomorrow or what mightpeople need tomorrow?
And that kind of led me to thisworld of biodegradable packaging
back in 2006.
And I thought that, hey, you know
what, this might be a really coolway to help.
the world, help Earth.
You know, we have this problem or
this potential huge problem comingon the horizon with plastics and
packaging.
And, you know, I wasn't obviously
(08:20):
prepared for how big the world ofconsumerism would become through
online at that time.
That wasn't the topic of
conversation so much, but thelevel of biodegradable discussions
were just starting to boil to thesurface.
So I thought, hey, let me getinvolved in something that I had a
passion for.
So I had a... manufacturing
process out of India, where we'reconverting a fiber into 100 %
sustainable biodegradablepackaging product, almost like
polypropylene, like a plastickylike material, but it was made out
(08:43):
of a natural fiber.
Right about the time I was getting
ready to sign a distribution dealfor North America, my mom got into
a life threatening car accident.
And very similar to, you know, how
my grandmother's moment waspivotal in my life journey.
This moment with my mom was aswell, because I had to make a
choice at that time on caring formy mother or caring for my
(09:06):
business.
And to me, there wasn't really a
decision to make.
My mom was on life support.
I stayed by her bedside for 18days.
We nursed her back to health,incredible hospital and care
system here, saved her life.
And, you know, we were able to get
her back to where she needed tobe.
And during that time, theopportunity in that business had
passed, unfortunately.
So when I was looking for the next
(09:28):
opportunity, like accidents, I wastalking to a family member very
shortly after.
He was just asking me, hey, what
are you going to do next in yourcareer, in your business, in your
life?And I said, I don't know.
And he said, hey, you ever thoughtabout the mortgage business?
And, you know, my background ofeducation is actually in
(09:48):
economics, love real estate,always have as a side passion,
never thought it would become.
kind of the full -time passion.
And I took a look at it and I waslike, you know, I can get in love
with this and I can change thelives of a lot of people doing
this.
And it was like a month later I
was in and here we are, man, 17years later.
(10:09):
Man, when you jump, you leave, eh?You just go right in and figure it
out.
In my life, I don't think there's
any other way.
I think if you're going to do
something, you just go for it,man.
And, you know, you're going tolearn along the way.
figure it out.
Yeah, that's fantastic.
So when you say you got into themortgage business, how did that
start?Did you start as a mortgage agent?
Started as a broker, you know, atthat time, I wanted to learn at
(10:34):
least one of the lessons that Ilearned from my time running the
transportation logistics businesswas that You know, coming in with
a little knowledge is going to setyou back a lot more than coming in
with a little more knowledge.
So I wanted to make sure that I
can come in as knowledgeable aspossible.
So I took the broker course, whichat the time was very robust.
It was a year long.
We had to do a two month
internship stint in the middle ofthat year long full time course,
by the way, was like a nine tofive, 16 university credits.
(10:56):
It was offered here through Senecavia the University of British
Columbia.
So we learned a lot.
I mean, we learned about realestate law.
We learned about fundamentals.
We learned about economics.
We learned about appraisals.
We learned about real estate math
and mortgage math right down toits core.
Learned about securitization ofloans and how, you know, mortgages
are really structured here inCanada.
And I thought that knowledge wasvery helpful to me in the early
(11:17):
part of my career until I got intothe business.
Then I quickly learned that itdoesn't matter how much you know
when you don't have anyone toshare it with.
So I learned that all of thattechnical knowledge that I had
gained coming into this industry,which I thought was going to be
very helpful and has beenthroughout various aspects of my
career path.
But I learned a hard lesson on day
one, which is it doesn't matter ifthere's no one in front of you.
(11:38):
So I quickly started to educatemyself on people, sales,
marketing, you know, all thosethings that I had kind of done
naturally in other businesseswithout having fundamental
knowledge, but became very wellversed in those areas.
And now I like to think of myselfmore as a sales and marketing
executive than a mortgageexecutive.
Yeah, that's really interesting tothink about that story that way.
There's a lot of talk in ourindustry these days that, you
(12:00):
know, a lot of agents just simplyaren't educated enough to be
advising consumers.
I see those conversations from
time to time.
And obviously, getting a license
today is much easier than it wasback then.
So do you think that we shouldlive in a world where mortgage
agents have to spend significantlymore time, energy, money to get
into the business the way that youdid?
Is the most important thing justgetting in, starting to talk to
(12:22):
people and learning while doingessentially?
I'll give you a couple ofdifferent perspectives on it, a
couple of different perspectiveson it, and then I'll give you my
answer.
When we started this company, I
was very challenged as to why theregulatory requirements had
changed so much.
And people were coming into this
industry and coming into thisbusiness with very little
knowledge about.
both like mortgages and people
like very little knowledge aboutfundamental mortgage rules and
(12:42):
information that they probablyneed to know in order to help
their clients make the bestdecisions.
But also on the flip side, like,you know, inability to communicate
and articulate complex informationthat we work with on a very daily
basis.
So I was kind of struggling with
that.
So I did a lot of kind of
reflection as to like, why wouldthe industry do this?
Like, why would the regulatorswant to make it easier versus?
(13:04):
is harder.
Obviously, I don't have the end
answer to this because it wasn'tme who made that decision.
But when I thought about it, Ithought, you know what, look, the
country is growing, the economy isgrowing, and the need for this
industry is growing.
The need for what we do as
mortgage agents, as brokers, assolution providers, the Canadians
(13:24):
was growing as our population was,and the need for housing became
more required.
So I thought to myself, okay, you
know what, maybe it's not a badthing that we have more people in
this industry because these peopleneed to help Canadians.
It all came back to helping,right?
We need to help Canadians achievetheir dreams of homeownership, put
(13:47):
a roof over their head, helpcreate that security where they
can raise a family, where they canfeel safe, where they can build
financial wealth through investingand other home buying strategies
or other real estate strategies.
Then it became, OK, maybe it's
justified, but what do we do?Because you do need that
knowledge.
So then as an industry, we have to
get better at raising the bar oninternal education and providing
(14:07):
the resources and the knowledge tothe agents as they're coming in to
make sure that the correctinformation is being articulated.
Now, I said I was going to give acouple of different perspectives.
The other perspective is, andsomething I believe very heavily
in, is I believe in the gym and Ibelieve in.
game time.
And I always use the analogy of
athletes when I give this example.
Athletes don't go into game time.
(14:28):
not taking that three -point shot100 times or not taking that free
throw 100 times in the gym.
They're in there practicing plays.
They're in there practicing whathappens in various circumstances
and situations.
Let's take, for our purposes, call
that objection handling, maybe.
They're going through different
scenarios multiple times in thegym before the game ever happens.
They're strengthening muscles.
They're strengthening endurance.
They're watching film.
So do we do enough of the gym
(14:51):
time?question in the mortgage industry
because game time is when there'sa client in front of you you don't
have the ability to practice on aclient it's not fair to the client
it's not fair to you it's not fairto your business so where is the
gym is really the question so thegym could be in the classroom It
could be through more regulatoryrequirements of education, or it
(15:15):
could be on raising the bar ofwhat brokerages and organizations
like ours have to do to supportthe people that, you know, in the
end work for them and provideguidance based on the solutions
that they have to offer asorganizations.
So I think one way or another,Vakim, there needs to be a higher
bar of education.
I'm not.
certain on whether it needs to befrom the regulators forcing it
(15:37):
upon people or just raising thebar of what we need to do as
leaders in this industry, which ispart of the reason why we ended up
where we are and big supporters ofeducation here.
So how does Pineapple Today, whichyou're the leader and CEO of,
build its business aroundeducation, training, coaching?
Because it's my understanding thatyou guys put a lot of effort and
(16:01):
energy into A lot of timesbringing in agents who are very
new to the business and helpingthem become professional mortgage
agents.
Obviously, it's not as regulated
as it could be.
So it falls back on the brokerage.
How does Pineapple handle that?You know, from our perspective,
like what we did and what wealways ask ourselves is, what is
the purpose and what is theintent?
(16:21):
Anytime we're going to try totackle a problem, right?
And then you kind of begin toreally realize and dive into the
core of, you know, what theproblem is and how your solutions
are going to aid in that problem.
So when we asked ourselves purpose
and intent, you know, purpose,obviously, to support the
regulatory framework and, youknow, let's call it lack of maybe
(16:44):
necessary education that amortgage agent needs to be able to
properly serve the needs ofCanadians.
And the intent is.
Obviously, coming back to help,
helping mortgage agents andbrokers build more robust, strong
businesses, helping mortgagebrokers and agents provide more
accurate and knowledgeableguidance towards the Canadian
consumers.
And in the end, helping Canadian
consumers achieve their dreams ofhomeownership while building a
stable and strong economic fabric.
As we both know, the home buying
and real estate market in Canadaplays a significant role in the
(17:09):
strength of our overall economy.
So then when we kind of really
realized that, so we began tobuild it into everything that we
did.
So, you know, training for us
transcends beyond just training,you know, which we have a lot of.
We have, you know, live training.
We have recorded sessions.
(17:30):
We have an LMS platform that webuilt.
I will call that more likefundamental training.
But then let's take training astep beyond, right?
So, you know, when we built ourunderwriting department, internal
processing, which most brokerageshave, you know.
Training got layered into thatbecause what we believed was that
new mortgage agents coming in thatmaybe lacked the experience to be
able to provide solutions to theirclients needed a resource to be
(17:51):
able to get that guidance.
And then when we built our
systems, we built it withvisibility so that our agents
could see what our underwriterswere doing, back and forth
conversations with the lenders,document collection with the...
So they were seeing, hey, whatquestions are they asking?
What problems are they tackling?Why is this being asked?
So they were kind of learning asthey were going through the
(18:13):
process without impacting thecustomer in game time.
Right.
Very similar to like marketing.
You know, a lot of our marketingcommunications, we do a lot of
internal marketing on behalf ofour agents out to their consumers
and provide knowledge andeducation.
But before a marketingcommunication goes out, we
actually educate the agent on thatcommunication.
(18:34):
So if we're going to talk about aspecific item, let's just say
hypothetically we're going to talkabout the role of tariffs on
interest rate fluctuation, then wewill make sure that our agents are
educated on that topic prior tothat communication going out.
So they have talking points andthey have the ability to discuss
it when the reaction comes in,right?
And the reaction is responses tothose emails with questions about
(18:54):
that subject matter.
So we began to see that training
had to transcend.
just training as a pillar of our
company and have an impact or havea touch point in every aspect of
everything we did.
So that's where we built like
agent onboarding.
That's where we built succession
planning and how to elevate yourcareer to become a team leader,
(19:16):
eventually become a broker owner,if that's the succession plan or
if that's the path that you're on,how to navigate various aspects
from technical to sales andmarketing to maybe even
philanthropy, which we have.
actually talk a lot about giving
back to the community and how toserve them, right?
So it became this whole robuststructure that evolved into every
aspect of our business focused oneducating, whether large or small,
(19:38):
like whether we're teaching youabout one thing through an email
that's going out or through awhole program through a two -hour
session or even a whole path ofyour career through a five -week.
course, right?It just became a part of who we
are is the short answer.
Yeah.
I'm curious of how much of whatyou are today was part of the
original vision versus how muchhas been an evolution as you've
(20:01):
had to pivot, adjust, remakeourselves in this industry.
When you think back to the earlydays of starting Pineapple, to
where you are now, what do youthink was your truest assumption
in hindsight?And what do you think was maybe a
false assumption in hindsightcompared to what you are now?
I think what a lot of people maybeforget or don't think about as
often, maybe they don't forget, isthat there's more than one right
(20:23):
way to get to that destination.
You know, if I'm coming to visit
you right now, you know, I cantake the 401.
There might be a truck flippedover.
There might be bad weather and Ican detour.
And I can take a side road.
I can stop and wait.
I can rest and sleep for thenight.
(20:44):
There's more than one way for meto get to that same destination.
And that's what's happened hereover my time at Pineapple.
We've come to learn that the goalhas always been the same.
But the way that we're going toget there has evolved and changed
significantly year to year, monthto month, sometimes even day to
day, right?But the goal has been fundamental,
right?We started this business on the
(21:06):
premise of we want to give back tothe community of mortgage
brokering.
We want to make sure that we are
helping mortgage brokers andagents build strong, successful
businesses that they are then inturn to translate to their
consumers and helping consumersbuild strong, you know, real
estate portfolios or real estatejourneys.
And it started with three pillarsof support, training and culture.
(21:28):
And today, those three pillarsstill live.
all rounded out throughtechnology, but they still live
very strong.
And although maybe not the same
road that we had envisioned fromday one, maybe not just a straight
shot on the 401, but we hitdetours, right?
We hit obstacles, we hit trucksflipped over, we hit bad weather,
we hit flat tires, we ran out ofgas.
(21:52):
And we just had to find solutionsto those problems and realize,
hey, if we stay focused on the endgoal, which is to uplift our
industry, then we'll still be ableto get there by taking detours and
different routes.
So I think that we're right on
course to where we had to be, butprobably not just on the same road
that we thought we would havebeen.
I like that analogy.
(22:13):
I wonder how much of that comes
from your background in logistics.
I guess part of your journey that
makes folks curious is goingpublic as an organization, which
is a rarity in the mortgage world,but you guys did that.
Was that a part of the originaljourney or was that another one of
these sort of detours that helpsyou get to the eventual
destination and just a part of theoverall journey and story?
(22:37):
Yeah, that was definitely adetour.
You know, it wasn't in thebusiness plan on day one that we
said, hey, you know what, let'sbuild a company, grow it to a
stage, raise some capital, take itpublic, IPO, you know, all those
kind of things, as some businessesdo very successfully.
For us, it was more of stayingtrue to our goal.
And as we got to a point, and Iremember the point, it was in and
(22:59):
around 2020, where we hadrealized, hey, you know what?
We're funding just around abillion dollars a year in
mortgages.
We're growing at an incredibly
fast rate.
We had wonderful user adoption and
feedback for the solutions and thetools and the resources that we
were providing.
We had a great culture, but we
were only operational in Ontarioat that time.
(23:22):
And we said to ourselves, we said,hey, listen, we have something
special here.
Maybe it's time.
Maybe it's time for us to put ourfoot to the gas and see if we can
accelerate this across Canada andreally leave a lasting footprint
on the industry and on the market.
So that's when we decided in order
for us to do that, we had to raisesome capital.
(23:44):
We could have continued to go theorganic path, which we had done
for the first four years of thebusiness, completely bootstrapped,
completely profitable and growingat an incredible pace.
But we said, well, hey, look, wehave a moment in time right now.
We have an opportunity where wecan accelerate and where we might
be able to do something reallyspecial that we otherwise would
not have been able to do.
So we raised our first round of
capital, which closed in 2021, $9.3 million.
(24:07):
And with that, began to tackle.
those goals.
So we expanded nationally today,represented in every province.
You know, we doubled our agentcount.
Well, actually, we tripled ouragent count now since that initial
moment.
We've almost tripled our funded
volume.
So we started to do the things
that we set out to do.
But when we took in that capital,
we did realize that when you bringshareholders in and when people
(24:28):
invest in your business, you haveto give them a clear path and you
have to give them a path ofliquidity at some point in time.
And going public for us was acouple of different reasons.
I don't know if anybody's everasked me publicly the reasons, so
I appreciate you asking.
Part of it was industry related
and part of it was businessrelated.
From an industry -relatedperspective, which is very
(24:50):
important to me and somethingthat's often not talked about, was
that we wanted to elevate thisbrand of Canadian mortgage broker.
We wanted to be able to show theworld the impact that mortgage
brokers have on Canadians, notjust like a Canadian buying a home
and being able to source a propermortgage rate or the right
solution to meet their needs.
That, for sure.
(25:10):
But beyond that, the impact thatmortgage brokers play in the
overall economic landscape andhealth of Canada, like how
impactful are we that we helpconstruction financing and
development and people along thejourney of their home buying?
We help people with refinances anddebt consolidations.
We help with commercial financingand help funding all of these, you
know, now large scale logisticscenters like Amazon and other big
distribution hubs that have becomesynonymous with.
(25:31):
you know, the landscape ofdistribution and with, you know,
goods and services getting intothe hands of Canadians.
Well, I mean, a lot of it startsright here in this industry.
And we wanted to elevate.
what we do as mortgage brokers i
don't think that canadian mortgagebrokers because we didn't have as
much market share as u s mortgage brokers or european
mortgage brokers or australianmortgage brokers at that time you
(25:52):
know we're often an underthoughtright you think of mortgages and
you think about the bank but no wehave an incredibly vibrant
community here and we wanted toshowcase that so that was a big
reason why we took this step.
We did it on behalf of all of us
to be able to raise the brandequity of what we all do as an
(26:15):
industry.
And the second part of it was
business related.
The second part of it was access
to public treasuries, access tocapital, which helps our business
grow, helps our business continueto have the funding requirements
that we need to run deficitbudgets or non -deficit budgets,
depending on what our goals are orwhat our objectives are at that
time.
allows our shareholders to have
liquidity options so if you wantto invest into the business you
(26:36):
know how you're going to get outversus a private buyout so there's
the business side of it and thenthere's the industry side of it
and both of those converged intous making the decision to do it
and we knew we were going to do itwith tough times ahead for certain
aspects of it, but we knew thatcertain aspects of it were going
(26:58):
to be great.
It's a catch -22, right?
There's no right decision ever.
There's the decision that makes
the best sense for you, yourorganization, and your company.
And we felt that that was theright decision for us, and we
still do today.
That was going to be my next
question, was the hindsight biasaround this, which is looking back
(27:19):
and trying to make the decision,was this the right thing to do?
for you as an organization.
So it sounds like you answered
that.
I do want to ask you, how does
being a public company and being apublic CEO change the way the
company operates?Does it have any effect at all
(27:40):
other than obviously the reportingneeds of being such a business?
Or is it much the same in terms ofthe operations and the goals?
I remember when we started thisjourney.
to do an IPO.
And, you know, obviously an IPO
involves a lot of external supportfrom bankers and underwriters,
like capital market securitiesunderwriters, lawyers and
auditors.
There's so many people involved in
this process.
And one consistent in that journey
(28:02):
was that when we met withsomebody, they always said, you
guys are a private company runningas a public business.
And, you know, I didn't fullyunderstand what they meant at the
time because I've never been apublic company.
executive until now, but I beganto learn as I became public.
And that was, you know, withopenness and transparency and
organizational reporting andcorporate governance and, you
know, all of those things that Ithink all great businesses have,
(28:23):
whether by accident or by design.
And, you know, some of ours was by
accident, some of it by design,but we were always running our
business with.
high regard for the people
involved in it.
So we didn't start the business as
pineapple.
But in the early days of our
company, we had a saying where,you know, when a mortgage agent
(28:44):
and broker entrusts us withsomething as valuable as their
career, we have the responsibilityto treat it with the utmost
respect.
And every single day, we'd all
come into work, all of us, myselfincluded, all of our staff, all of
our employees, and we would holdourselves to that standard that We
work on behalf of all of thesepeople, hundreds of people that
trust us with the greatest gift.
Like, I mean, you know, this is
(29:05):
their career.
This is how they pay their bills.
This is how they feed theirfamilies.
And we have a responsibility totreat it with that respect.
And that responsibility is whatled us to the governance and to
the transparency and to theopenness, some by accident, some
by design, but then led us to theIPO.
In some ways, sure, the businesshas changed, you know, a lot more
reporting, a lot more shareholderengagement, different calls for me
(29:27):
sometimes throughout the day thanwhat I was used to.
But in some ways, the business hasjust always kind of been running
this way, right, where we justwanted to run a really proper,
ethical, organized company.
Well said.
So there was something you saidearlier I want to go back to,
which was about elevating themortgage broker in Canada
specifically.
And I'm curious, this is something
(29:47):
I think about often.
I had the privilege of watching
that journey transpire throughoutthe United States.
I mean, at one point, mortgagebrokers were a huge part of the
market.
You have the crash, mortgage
brokers, a lot of them just getout of the industry entirely.
And then you had the period fromroughly, I want to say 2014 to
(30:08):
today where mortgage brokers arethriving over there.
able to do.
Even in the time that I've been
operating in the Canadian marketgoing back to 2020 now, I think we
went from 20 % to roughly 40 %mortgage broker market share.
And that number fluctuatesdepending on the number of
renewals going on at any giventime.
And of course, rates play afactor.
But one thing I've often talkedabout is we don't have a got milk
(30:34):
question mark for Canadianmortgage brokers.
Like there is no trueorganizational structure, and it
feels very siloed in the mortgagebroker community.
And I don't think the publicunderstands the true value of
mortgage brokers.
So when you say that, I get
excited.
But I do also question for myself
sometimes, and I want to pose itto you, which is like, how do we
measure success outside ofmortgage broker market share in
(30:56):
this industry for mortgage brokerssuch that we can elevate the
entire broker community?Such a great way to think about
it, right?Because, you know, we often think
about like market share or revenueor volume as kind of, you know,
the key indicator, right, ofsuccess of what anybody does.
But as we all know, like there'sso many more layers and there's so
much more that goes into it.
I think one of the things that is
(31:19):
often not talked about is, youknow, what you just shared about
just the elevation of marketshare.
And I know that's not the specificquestion, but I just want to touch
on it quickly.
So, yeah, we went from 20 percent
to 40 percent.
We peaked over 50 % at a certain
point a couple of years ago.
We've kind of dipped back below.
But I'm very certain that we willbe in and around that 60%, 70 %
(31:44):
range within the next few years.
And I don't know exactly what the
next few years means, whether it'sone year, two year or five years.
But I think within that next nearfuture, mortgage brokers certainly
do have the majority market share.
But what does that then mean,
right?And what does that mean to what
we're talking about?Well, now we're talking about how
(32:04):
many Canadian small businessowners that are now contributing
back to the economy.
in multiple different ways.
So how many mortgage brokers do weknow that hire multiple assistants
and social media managers andmarketing firms and sales managers
and, you know, infrastructuralsupport, admin teams, payroll,
compliance that are needed tooperate these businesses?
So now we have small businessesthat turn into, you know,
(32:25):
employers and, you know, what weresolo entrepreneurs are now
funding, you know, tax dollarsback into the economy.
They're funding other ways ofsupporting Canadian job growth and
other ways of us kind of givingback towards what I referred to as
this economic fabric.
So I think that's one way of
looking at the success of it.
(32:46):
I think another way of looking at
the success of it is...
The fundamental impact that we
have on the lives of Canadians.
And, you know, I always talk about
my parents as immigrants cominginto this country and leaving
their homeland in search of betteropportunity for us.
And the responsibility that wehave that I believe I have as kind
of this next generation, firstgeneration born son of immigrants.
(33:14):
I believe that if they lefteverything behind for more
opportunity for me, I better seesome of that opportunity and kind
of do everything I can in mypower.
to achieve that for them becausethey sacrificed a lot.
The reason I bring that up is howbig a part was that dream of
homeownership for them?And how big a part was that
(33:35):
ability to have a roof?A safe roof, let me refer to that
actually, a safe roof over theirfamily's head.
Because a lot of people that comeinto this country, which sometimes
we take for granted, might have aroof over their head where they
come from, but it's not safe forthem.
Or they don't feel it's a placewhere they feel safe and secure,
where they can raise their kidswith freedom and expression and
(33:56):
happiness and memories andlaughter and tears and all of
those things that we remember whenwe think about our time in our
homes.
I think that's another way to
measure success is like when welook at, you know, my parents that
bought their first home in the 80sfor.
less than $100 ,000 and recentlydownsized and sold it for over a
million.
That ability for them to find
financial success, but not justfinancial success, they found life
success.
They raised their kids.
(34:16):
My grandmother passed away in thathome.
That's where I held her in myarms.
Like that was a safe place forher.
So where I learned to ride mybike, it's where I came when I
proposed to my wife.
It's where my daughter was born
when my house was being built andI had nowhere to go.
And my parents said, come stay.
My daughter was raised her first
year in that house amongst hergrandparents.
(34:38):
I think there's so many ways forus to think about success in life
outside of just dollars and centsand volume and revenue.
And I think that's what themortgage broker industry.
for me anyways, needs to elevateis that impact that we have, the
impact on the lives of otherbrokers, on the lives of our
(35:02):
staff, of our employees, of ouragents, of Canadians that we
impact every single day.
And if we take their money aside
for a second, I think that we areincredibly successful as an
industry in what we achieve andwhat we accomplish.
That's really well said.
And I couldn't agree more when I
think about the impact thatmortgage brokers have on
(35:24):
homeownership as a child ofimmigrants myself, being able to
own a home in the West and raise afamily around that compared to
other parts of the world.
It's just an incredible impact
that we get to make.
So I want to wrap up by just
asking you about impact.
what you want to build when you
you know jump out of bed every dayand presumably you're somebody who
(35:44):
leaps out with a bit of enthusiasmgiven how much you talk about
helping people and helping theindustry as a whole what do you
want your impact to be on thismortgage industry So truthfully
for me, I have a great admirationfor those that came before me.
And I think that we are all aproduct of our predecessors, just
as other companies and otherindividuals and other people have
(36:07):
laid groundwork for companies likeours to be able to thrive and
succeed and build off of andimprove.
What I hope is to leave that samepath.
I hope to be able to leavesomething.
and help others realize that theyare the future of this industry
and they can pick up where we leftoff and they can take what we've
done and improve upon it and fixit and make it their own.
(36:28):
And I think if we all have thatnatural insight that generations
will continue to progress and ourjob as an industry today in the
generation that we live is to takefrom our predecessors and give to
our successors.
then I'd be happy.
So that's the impact I want toleave.
I want to be able to leave mysuccessors something that they can
take and run the ball with andmake it their own and make it
(36:50):
bigger and better than I couldhave ever dreamed of and imagined.
Yep, totally get it.
We have been past the torch and we
will have to pass that torch.
And that's really well said.
So thank you for joining me today,Shuba.
Keep up the fantastic work withyou and your team at Pineapple and
keep pushing this industryforward.
(37:10):
It's greatly appreciated.
The honor has been mine, man.
And, you know, I have greatadmiration for you and so many
other colleagues around thisspace.
So I say the same to you as wellas our peers.
Thank you.
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