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May 5, 2025 • 24 mins

Ever wondered how pest control, landscaping, and janitorial companies are being transformed through innovative financial technology? Jacob Olins, SVP & GM of Fintech at WorkWave, takes us deep into the world where field service management software meets cutting-edge financial services.

WorkWave has positioned itself as the operating system for field service businesses, providing everything from customer acquisition tools to mobile apps for technicians. But what truly sets their platform apart is how they've revolutionized payments and financial services within these traditional industries. Olins walks us through their journey from payment reseller to full Payment Facilitator, giving them complete control over the customer experience and unlocking new revenue opportunities.

The most fascinating aspect of our conversation reveals how embedded financial services are solving real business problems. For companies struggling with customer retention, WorkWave's card-on-file and subscription capabilities have helped transform one-off service calls into recurring revenue streams. Their consumer financing partnerships make large emergency services affordable for homeowners. Perhaps most impressive, their earned wage access feature has increased employee retention by over 30% by allowing hourly workers to access earned wages before payday.

Ready to understand how the $13 trillion banking industry is being reshaped by innovative software platforms? Listen now and discover insights that might forever change how you view the intersection of software and financial services.

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
Welcome to the Leaders in Payments podcast,
where we talk to C-level leadersfrom across the payments
landscape.
We'll be discussing theproducts and services that
impact the payment space today,as well as trends and
predictions for the future ofpayments.
We will also hear stories fromour guests about their journeys
to the top.

Greg Myers (00:18):
Hello everyone and welcome to the Leaders in
Payments podcast.
I'm your host, greg Myers, andon today's episode we have a
very special guest, jacob Olins,the VP of FinTech at WorkWave.
So, jacob, welcome to the show.

Jacob Olins (00:29):
Hey, greg, it's a pleasure to be here.

Greg Myers (00:31):
Well, why don't we start out by having you talk a
little bit about yourself, maybewhere you grew up, where you
went to school, where youcurrently live, a few things
like that?

Jacob Olins (00:45):
Yeah, I would love to and yeah.
So I grew up in brookline,massachusetts, went to
university in in new york, movedto new york city after college.
Like a lot of people do, I sortof lucked into payments
innovation role at city bank,having, like you know,
absolutely no idea what thepayments industry was at that

(01:05):
time.
But it was super cool and justabsolutely set me on a path to
be in fintech and everythingthat fintech has become over the
past 15 or so years.
So that was Citibank's reactionto PayPal and eBay merging and
a lot of institutional clientsbeing like, hey, what is that

(01:26):
all about and how do we dosomething similar to that really
like high level big picturestrategy.
What's going on?
What is the new world of theinternet mean for payments and
payments?
Technology?
Gave me a bug about payments.
Gave me a bug about productmanagement and yeah, and so set
me on a path.
I spent a few years afterCitibank at Verifone, a big

(01:48):
payment terminal manufacturer.
I spent a few years at JPMorganChase, also doing fintech and
payments innovation more on theaccounts payable side, and kind
of the common thread throughoutthis was just seeing more and
more examples of paymentsgetting deeper and more embedded
into business applications andso, seeing that, loving some of
the examples of those use cases,I worked my way over to a

(02:11):
company called EPOS now, whichis a point-of-sale company, to
help launch their foray intopayments and ultimately a whole
suite of embedded financialservices.
And now I'm at WorkWave and weare a leader in field service
management software.
We're really like the operatingsystem for businesses that
specialize in landscape, pestcontrol, security, janitorial,

(02:35):
and so scaling out our paymentservices and looking to all
sorts of other opportunitieswhere we can add value to our
clients through fintechofferings.

Greg Myers (02:46):
Okay, well, let's talk a little more about
WorkWave.
So tell our audience a littlemore.
Obviously you kind of gave the50,000 foot level, but maybe a
little more detail around thecompany, maybe the size, the
different products and services,different audiences, a few
things like that.

Jacob Olins (03:01):
Yeah, yeah, absolutely so.
Workwave is.
We're about a thousand peoplein our company.
You know we're primarilyfocused on North America, but we
do have a presence in EMEA andAustralia as well, and our bread
and butter is building softwarethat helps field service
businesses.
And I get the.
The.
Really the real common threadis like is your business run a

(03:23):
fleet of service professionals,technicians, that go into the
field, either to commercialproperties or residential
properties, and perform servicethere?
And so the industry verticalsthat we are really the market
leaders in pest control, lawncare and landscape cleaning,
like janitorial, commercialjanitorial and security, and in
every one of these cases there'sa truck or a fleet that's

(03:46):
bringing technicians out to aplace to perform a service, and
that might be mowing a lawn, itmight be performing like a
termite prevention, it might besecurity guarding a stadium for
a big concert or an event, itmight be the nightly cleaning
operation that's happening at abig office building, and so,
like the biggest customers inthese areas use our software.

(04:08):
But we really scale from verysmall businesses to the largest
companies in these industriesand I say we're not super
focused on the micro merchants,the brand new businesses.
That's not really our bread andbutter.
But once you get to anestablished small business and
maybe you're doing half amillion in revenue a year,
that's when customers reallystart looking for a more
sophisticated offering.

(04:28):
And, yeah, those are really ourtarget customers and the
customers who find the mostvalue with all of the services
that we can offer them.

Greg Myers (04:35):
Okay.
And then those servicesobviously they use it for
scheduling, for communication, Imean, what are all the kind of?
I always describe Vertical SaaSas kind of the operating system
for the small business, right?
So maybe just discuss realquick some of the services that
you provide, other than payments, obviously, because we're going
to dive into that.

Jacob Olins (04:53):
Yeah, 100%.
Yeah, I mean it's the spectrumof the business.
We probably provide a service.
In many of the cases we're theowner of that, but in a lot of
cases we partner and becausewe're the operating system, as
you mentioned, we're thatprimary control point and real
estate, and so we can helpdistribute all sorts of things.
But it starts with customeracquisition.
We provide marketing tools thathelp our customers source new

(05:14):
clients, and then we provide CRMso that our clients can keep
track of the closed, one closed,lost, and then manage those
customer relationships.
And then there's a big aspectof dispatching right, so you're
routing these trucks in the verymost efficient way so that our
client can hit the most housesand have the most routes and
therefore run the most efficientbusiness that they can.

(05:34):
And then their technicians areusing our mobile app and so
that'll tell them exactly whatservices they need to provide.
Maybe there's certain chemicalson one lawn and then a mowing
treatment on another lawn.
Maybe it's a routine pestcheckup in a certain place, but
it's a termite prevention or arodent exclusion in another
place, and so all thatinstructions that the technician

(05:54):
gets is all in that mobile app.
A lot of these industries areregulated.
So we provide a lot of thecompliance requirements to make
sure that to give the consumercomfort yep, you're getting a
chemical treatment, but thisprovider is completely licensed
and here are the disclosures andwhatnot, and then all of the
invoicing is happening throughour platform.
So I think in a lot of wayswe're also, like, have been

(06:16):
responsible for some of thetransformation of these
industries.
Historically, like 10 years ago, a lot of these industries were
one service at a time right,you're calling because you've
got a problem, you're gettingtreatment for that problem, kind
of like how you'd use a plumberor an electrician today.
And we've been able to help alot of these businesses evolve
into recurring servicebusinesses and a lot of our

(06:37):
customers attribute that to,like the payments capabilities
taking that CRM, enabling thecard on file-file, enabling the
auto-pay capability, poweringthat auto-pay capability with
account updater so that theydon't have to chase customers
whose payment methods go expiredand whatnot.
Yeah, and then in some of theseverticals we provide accounting

(06:58):
services.
In some of these verticals weprovide payroll services, and
the payroll services extend intohow can we help our customers
with employee retention?
So we'll go into earned wageaccess.
If it's a big mobile workforce,it's primarily hourly, and a
lot of times, waiting two weeksfor your paycheck can put these
individuals in difficultsituations.
We try to do things that driveour customers' employee

(07:20):
retention and then just make iteasier for those employees to
live their lives in afinancially responsible way.
Yeah, and then in some of theseverticals we're like we're the
accounting system, the ERP, andso there's, you know, expense
management, and we've started tolaunch some bill payment
capabilities as well in ourFinTech suite.

Greg Myers (07:36):
Okay, Okay.
Well, let's talk about embeddedpayments for a minute.
Maybe describe how it'sembedded and maybe you know how
it got to this point.
Did you start as kind of theISO of the world?
You're now a Payfax, so maybetalk about that journey a little
no-transcript.

Jacob Olins (07:55):
Totally, yeah, I mean, I think it is like a very
common story.
You know how vertical SaaSplatforms like us moved to and
today we're a Payfax.
So we, you know, fully own therisk, the compliance, the
product, the onboarding, theselling.
But wasn't always like that inthe early days and it predates
my time at WorkWave, certainly.

(08:15):
But yeah, we started as areseller, so we were early on
the integrated payments offeringand then, as a reseller, we
were reselling, referring ourcustomers to payments providers,
and those payments providerswere setting up a merchant
account and it was usefulinsofar as you could attach that

(08:35):
customer to a card and youcould start to do some of that
recurring payments and there wasa level of integration.
But there was also a lot ofdissatisfaction with hey, why
are there so many differentsuppliers and why is there
inconsistency across the datathat I get from you and the data
they get from them?
And dissatisfaction just with Iget one level of service from

(08:56):
my vertical SaaS provider whichis fantastic, but then, like
payments which can some likeit's less critical until it's
more critical, right, like thesecond, that it's that the
settlement is late or that theauthorizations aren't working,
like that's when you sort ofrealize, wow, this is such, I
might argue, the most criticalpart of the platform that we

(09:17):
offer.
So, yeah, anyway, it was justit was customer feedback driven
that we started to exploreowning more of the solution
ourselves, and so we moved tothat PayFact model pretty early
on I think that was around 2019.
And that turned out to be aphenomenal strategy for us, a
real win.
Customers got a better product,it was easier for us to manage.

(09:37):
Obviously, it's a good businessmove for a vertical SaaS
platform.
So then we continued to scalethat we made a couple of
acquisitions.
We were able to deploy thatWorkWave payments really as a
common service to these newacquisitions that we were
bringing in.
So that really helped makethose acquisitions more
accretive to our business and itjust continues to be a key area

(09:58):
for us and a key part of theplatform and the value that we
provide to our clients.

Greg Myers (10:03):
Okay, and how do your clients typically use the
payment solution?

Jacob Olins (10:07):
So our clients will sign up for our software and
our payments product just comesincluded in the software.
And so most of our clients,because they're more established
, they understand credit cardprocessing is critical.
So most of our clients, becausethey're more established, they
understand credit cardprocessing is critical.
Obviously, the things thatwe're helping in our overall

(10:29):
sales process, the things thatwe want to make really clear to
our customers, is like you'retrying to run a business that is
as much as possible onsubscriptions, so you want to
get every one of your clientsonto subscriptions and then you
want to secure thosesubscriptions with a card on
file and with an auto payment,and so it's that combination.
It's like, yes, it's the CRM,it's the CRM that's adding the
card to that account, it'smanaging that customer account

(10:51):
and then it's billing thatcustomer account in a way that
you don't have to maintain thatat all.
So that's our sales process andthat's a really obvious value
proposition right, and that likeintegrated.
I think part of the beauty of itis when you're combining these
things, like you're not sellingpayments, you're just selling
business management and it'spart of the broader business
management value prop.

(11:11):
You move further up market andwe certainly have a lot of
enterprise clients and you haveto get into a lot more of the
payment specifics and we supportflat rate billing models and we
support interchange plus ratebilling models and we offer
things like network tokenizationand we have to get a lot more
sophisticated to support theneeds of the larger enterprises

(11:32):
who have payments, people whoare part of the buying process.

Greg Myers (11:36):
Do your customers take payments out in the field?
Do you have that option?

Jacob Olins (11:41):
Yeah, we do.
It's not a large percentage,most of it is card on file
subscription.
But absolutely and I kind ofbreak down in our customer base
like the oversimplified way tothink about one of these field
services businesses they'reprobably doing like 50% of their
business, 50 or 60% of theirbusiness is like a residential
subscription, and then 20, 50%of their business, 50% or 60% of
their business is like aresidential subscription, and
then 20%, 25% of their businessis a commercial subscription,

(12:05):
and then there's 20% to 25% oftheir business.
That is like a one-off service,a large ticket item, and so
certainly for those large ticketitems, we're doing some payment
acceptance in the field, and sowe've got a device, a physical
device.
But one of our big initiativesthis year that we're excited
about is moving that to atap-to-pay, because these
technicians are already on ourmobile app, and so we've got

(12:27):
tap-to-pay on our roadmap andwe'll be rolling that out.
Yeah, the other thing you see inthe field, like in these remote
settings, is if you've got aBluetooth device, it's an extra
device, you've got connectivityissues and so just the
convenience of tap to pay somestore and forward technology.
It'll probably increase theamount of percentage of card
present transactions that we'redoing.

Greg Myers (12:47):
Right, okay.
Well, moving beyond paymentsand under the fintech umbrella,
what other financial servicesproducts do you offer?

Jacob Olins (12:55):
Yeah, it's been a big part of my strategy since
joining WorkWave is just toextend further and further into
financial services and we've gotlike so many great
opportunities just where we arein that ecosystem as that
operating system.
So you know, the big one of ourmost exciting opportunities is
consumer financing and so I wastalking about that.
20 percent, 20 to 25 percent ofthese businesses.

(13:15):
That's one off.
Well, a lot of those big ticketjobs are their big ticket jobs,
so they're not alwaysaffordable with with what an
individual's got in the bank,but in the vast majority of
these cases it's a criticalservice.
You got a tree trimming, needbed bug, need something like
that.
So financing those consumers isone of our big initiatives this
year.
And we've got a greatpartnership with a company
called WiseTac.

(13:36):
That's been really, reallyappreciated by our customer base
.
We do a merchant cash advanceproduct, so that's a capital
lending product.
We do that with a companycalled ULend.
They're a fantastic partner.
Our base is more upmarket andthose products are all just
shared.
I had a previous company.
It was a point of sale companyand we were really focused on

(13:56):
the micro, SMBs and capital inthat market that's super, super
underbanked, was like one of thehighest attachment new products
that we launched and our marketis just a little bit different.
I think you always got to thinkabout, with the financial
products that you want to extendinto payments is kind of like
the most horizontal, Dependingon the types of lending needs or

(14:26):
banking needs that yourcustomers have, what they're
already getting from banks, whatthat ecosystem looks like.
Your strategy might go one wayor another.
So, to elaborate on that, we'vegot in our security and
janitorial industries.
We're a full ERP and a payrollprovider, and so earned wage
access is our biggest fintechopportunity in that space, is
our biggest fintech opportunityin that space, and so we've had
some real exciting early successin earned wage access, like
seeing employee retentionincreased by like north of 30%

(14:49):
for our customers who are on it,and so just building deeper and
deeper embedded capabilitieslike so employees can see that
earned wage access opportunity,Like again they're on our mobile
application right, so they cansee it as they clock out.
That's like a super powerfulway to drive that attachment and
to drive that satisfaction.
And then ultimately it's likethat's actually the employee

(15:10):
satisfaction with their employer.
So it's like a very virtuouscycle.
And then bill pay.
So power you know, as that ERPenabling our customers not just
to export a Notch file but toactually pay their bills using
WorkWave and WorkWave partners.
That's a big one for us as well.

Greg Myers (15:29):
Okay, and you mentioned some of these
partnerships.
Are they white-labeled?
Do they typically get fullyintegrated, like payments does,
or sometimes are they a littlemore like a referral kind of
thing?

Jacob Olins (15:38):
Yeah, I think it's a great question and, like you
know, for me like the kind ofstrategy archetype is the
payments progression that we'vekind of all seen over the past
10 years.
Right, it's like you might notknow, you might have a lot of
theories about like what goodopportunities could be, could be
even like it can beoverwhelming.
Right, and in mostorganizations, probably more and
more, we're all like kind ofresource constrained, so are you

(16:04):
going to invest a lot inbuilding something from the
ground up that you're not 100%sure is going to resonate?
Meanwhile there's like thistremendous network of fintech
partners out there who haveproducts and would love to
partner with a company that'sgot great customer distribution.
And so I sort of like mirror,at a certain level, the payment
strategy, like, hey, let's setup a referral partnership, let's
see if that works.

(16:25):
All right, is there some product?
Is there some obvious productmarket fit?
If there is, great, let's leaninto this a little bit more,
let's start to embed this and weeven go so far as to, in our
partner strategy, take on thefull go-to-market right.
And so we've got to try to makeit a more sophisticated partner
model where we can kind ofstand up a referral, really

(16:47):
lightweight, but also offer toour partners like hey, this can
be virtually a zero costcustomer acquisition channel for
you and then, if the economicslook good, then we're able to
really invest in go-to-market,really incorporate it into our
core sales pitch.
The same way payments is.
This is a core part of theproduct.
The other beauty of it is a lotof cases these are usage-based

(17:07):
models and so you get lesssticker shock.
So there can be a high degreeof interest and, okay, cool, I
can use it a little bit.
I can see if it works at thecustomer level.
I can see if it works for me.

Greg Myers (17:17):
Okay, I can see if it works at the customer level.
Right, I can see if it worksfor me, okay, okay.
Well, when you kind of stepback and look at the payments
and fintech industry as a whole,where do you see it headed in
the next, say, three to fiveyears?

Jacob Olins (17:28):
Yeah, I love that question and.
I think it's like so manydifferent things depending on
the market, like where I paintthe perfect future state picture
and I'm going to come back alittle bit.
It's colored by my experience.
I spent a lot of years at bigbanks doing financial innovation
and new products at big banksand the problem there was you

(17:52):
got to gather so much context asa bank to provide a tailored
fintech solution to a customer.
And the beauty of the positionthat these vertical SaaS
platforms like WorkWave are inis we've got all that data,
we've got all that context.
We've got a really strong pulseon what the real problems are.

Speaker 1 (18:11):
And so.

Jacob Olins (18:12):
I see more and more financial services getting
distributed through verticalSaaS platforms.
I think it's a common trendthat a lot of us are seeing.
But when I was at my previouscompany focused on micro
merchants, it was like, oh, thismarket is so underserved from a
commercial banking perspectiveand so we launched a mobile bank

(18:33):
account and day one, 25% of newcustomers were attaching to
that mobile bank account becausethey weren't even really it was
pretty much greenfield.
They weren't even really.
It was pretty much Greenfield.
They weren't even really usingcommercial banks.
They were like co-minglingfunds in their personal accounts
.
So you can see that like, hey,maybe this is disruptive to
commercial banking, orcommercial banks are really just

(18:56):
infrastructure and the verticalSaaS platform owns that.
I think as you move up market itbecomes a lot more like can you
solve really discrete cash flowproblems?
And so one example I love is taxbank accounts where you say,
hey, we're the merchant acquirer, we're the payments processor,
we're that integrated into thebusiness management system, and

(19:18):
so we know the sales tax onevery invoice that you're
sending out and so we can split,settle that sales tax into a
special bank account and then wecan file your taxes and pay it
for you and indemnify you forany late fees or issues with
your tax payments, and I thinkthat concept scales.
But you got to pick your spotsright.
Maybe you'll bank payrollbecause your customer base is

(19:41):
like ours, workforce managementright, and that is the number
one cost.
Or maybe you'll bank supplychain because you do e-commerce
and it's all in COGS and so Ithink when I think five years
out, and it's probably more like10 years out, just a lot more
banking and treasury activitiesare happening in the platform on
top of like.
I don't think that.

(20:01):
I think it's the rare casewhere the platform becomes the
bank, but the common case wherethe platform, you know, is using
a API, banking as a servicekind of platform for these
specific cash flows.

Greg Myers (20:12):
Right, right, no, that makes sense.
Well, let's switch gears alittle bit and talk about you.
So maybe you kind of gave usyour background from a career
perspective, but maybe talkabout why WorkWave, what was
attractive about WorkWave?
And they were doing that.
You wanted to join the company.

Jacob Olins (20:27):
Yeah, I reached out to the WorkWave CEO at the time
two years ago, and it wasbecause, like, they posted a
great job rec for what I've kindof found is my niche, which is
really establishing these andscaling these and transforming
these like payments and fintechbusinesses within these vertical
SaaS environments.
So, you know, I think you'reseeing more and more of that and

(20:48):
you're seeing more and more ofthese vertical SaaS companies
like realize what a majorstrategic opportunity investing
in payments and but reallybeyond payments, fintech is.
So, yeah, that was what got meinterested in WorkWave and I
looked at that job rec, listenedto some of the CEOs' podcasts,
read about the company and said,okay, this company is doing a

(21:10):
lot of cool stuff.
Field services is a superinteresting industry.
It wasn't one that I had a lotof exposure to, but it's
definitely like you could seethe financial services
opportunity and could tell like,hey, this is probably a more of
a lagging industry and there'sprobably a lot more
opportunities for somedisruptive innovation.

Greg Myers (21:30):
Gotcha Okay.
Well, what are some thingsyou're passionate about?
Maybe one work-related passionand one personal passion.

Jacob Olins (21:37):
All right the evolving on the work front like
the evolving fintech landscapeand just how financial services
is transforming, and I thinkthere's a roughly $13 trillion
banking industry out there and99% of it is flowing through
traditional channels, so I thinkthat gets bigger.
But also a lot of that goestowards platforms and fintech

(22:01):
providers in the coming yearsand just tracking that and
trying to stay one step aheadthat's a lot of fun.
Personally, I'm married andhave three young boys a couple
of twins and a two-year-oldbehind them, so we're getting
into skateboarding and skiingand just doing all sorts of fun
stuff with them.
So, yeah, the family and thelittle kids trying to keep up

(22:22):
with little kids.

Greg Myers (22:24):
They keep you on your toes right.
They absolutely do Great.
So one last question If someonecame to you and they're
interested in building a careerin payments or fintech and they
just said, hey, jacob, like whatdo I need to do to be
successful in this industry,what advice would you give them?

Jacob Olins (22:41):
For me, what's worked really well and where I
think that I've got someuniqueness is really good
exposure to both the bankingside and the software side.
I think that a lot of people,maybe in similar roles to mine,
come from one area or the otherand so being able to round out
that experience, like on thebanking side, you really

(23:03):
understand the risk managementaspect, you really understand,
like the fundamental cogs youknow, you really understand,
like what does it cost from arisk management and from just a
pure materials perspective tobuild these businesses and so
what the economics are.
And I think if you're all onthe software side, you probably
get tripped up when you talkabout things like interchange

(23:24):
and basis points.
And likewise, I think peoplewho are just pure play payments
and banking people really missthe importance of the user
experience.
And so if there's a way thatyou can round out that right,
that you can really appreciatethe value that the product is
providing and the importance ofthe user experience, but you

(23:44):
also understand the economicsand like banking and payments
business models, I think thatgoes a long way and I think it's
pretty unique Okay.

Greg Myers (23:53):
Okay, well, obviously, jacob.
We've covered a lot of groundalready, obviously, about you
and your background and thecompany and payments overall.
Is there anything else you'dlike to add before we wrap up
the show?

Jacob Olins (24:03):
This is a wonderful show, Greg.
I really appreciate you havingme.

Greg Myers (24:06):
Yeah, absolutely so.
Jacob, thank you so much forbeing on.
I know your time is veryimportant, so I don't want to
take more of it, but thank youso much for being on the show
today.
Thanks for having me Great, andto all you listeners out there,
I thank you for your time aswell, and until the next story.

Speaker 1 (24:20):
Thank you for joining us this week on the Leaders in
Payments podcast.
Make sure you visit our websiteat leadersinpaymentscom, where
you can subscribe to the showand where you'll find our show
notes.
If you enjoyed listening,please share on your social
channels as well.
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Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

Ridiculous History

Ridiculous History

History is beautiful, brutal and, often, ridiculous. Join Ben Bowlin and Noel Brown as they dive into some of the weirdest stories from across the span of human civilization in Ridiculous History, a podcast by iHeartRadio.

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