5/27/26

Carpool Consulting - Cyber Insurance with Kyle Nichols

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Kyle: a hacker will hack into their thermostat their IOT thermostat and they will crank up the heat and lock the owner out and

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they will say if you don't get us 

Sharon: Oh my God

Kyle: uh you know a Bitcoin or some sort of digital currency ransom payment we're going to

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cook your house, yeah.

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Sharon:  Okay so my next guest is a managing director at-risk Strategies. He's worked in the insurance industry for 25 years

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um and I see him so let's go see if we can get him in the car. Hey, you need a ride

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ride 

Kyle: hey Sharon fancy running into you 

Sharon: how are you

Kyle:  in my neighborhood 

Sharon: very nice to see you 

Kyle: or your neighbor our neighborhood

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Sharon: both our neighborhood and I have a ton of questions for you 

Kyle: fire away 

Sharon: Can you tell us what cyber insurance is 

Kyle: Cyber  insurance is a policy that comes with a

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suite of services to protect companies and individuals from cyber threats 

Sharon: okay

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Kyle: from hackers extortions accidental um release of information data all that

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good stuff um and they have a component of first party. So if there's a claim they write a check to you or third

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parties who who if they write a check it goes to not you, it goes to the Third third party who was injured or uh had

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the claim happen against them

Sharon:  so when we're talking about cyber Insurance most people think oh a cyber security

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incident occurred 

Kyle: right 

Sharon: would it still apply to something that was a privacy incident ? I'm talking more like um misuse

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of personal information by the company that was collecting it

Kyle:  oh sure, yeah

Sharon: so would that be covered through cyber Insurance

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Kyle: there are coverage grants that allow for,  to protect the company against such accidental releases 

Sharon: okay

Kyle: uh for sure i

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Sharon: If you wanted to get Cyber Insurance do you need to prove anything to the insurance company like walk me through it

Kyle: yeah the

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privacy posture the IT security landscape with and how the company operates uh are all looked at. How do you

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handle and treat uh sensitive information uh do you have like when I say clean desk policy, it's like hey at night like where are these files going

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that contain private information

Sharon: Right, okay they do like an assessment on you to determine you know whether you're worthy

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of insurance like how does that work 

Kyle: Yeah it's kind of like uh going to Canada's Wonderland you have to be this tall to ride

Sharon:  okay yeah thanks I know what you're

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trying to do, I know most of you don't know but I am very sure, so thanks for trying to bring that in Kyle

Kyle: no problem

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no problem 

Sharon: That was rude

Kyle:  we go way back so we're fine 

Sharon: yeah you have to be worthy of getting cyber insurance. Why is that?

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It used to be really simple

Kyle:  yeah uh we've seen an a lot of losses take place

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and insurance companies act on data so when they have all this information then they can start underwriting for it 

Sharon: okay

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Kyle: and asking those questions and then as you go into more what I would say crucial Industries like healthcare

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technology data center type stuff um the underwriting gets uh pretty significant and so you do need, if I can do a little plug here, you do

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need a broker who understands what is required in those Industries in order to get insurance but also get the best

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insurance most appropriate insurance and the right cost coverage and limit in place 

Sharon: right 

Kyle: very shameful plug 

Sharon: very shameful. Well okay all this talk is

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getting me hungry and someone told me that when you're on a road trip you like team McDonald's Kyle: yeah I do 

Sharon: all right um

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so we're we're at McDonald's um hi there what can I get you 

Kyle: small coffee small fries

Sharon: That's it

Kyle: That's it 

Sharon: What about Big Mac

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Kyle: no way 

Sharon: can we have extra ketchup

Mcdonalds:  ketchup on the side 

Sharon: yes please did she just ask me if I want a ketchup on the side 

Kyle: yeah 

Sharon: what what's my other option

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ketchup on my fries? do they do that?

Kyle: no I no they 

Sharon: then why did she ask me that 

Kyle: I don't know

Sharon:  that seems like a useless.

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question kind of a waste of time do insurance companies ask useless questions what what what one useless

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question does an insurance company ask I know they do this for sure 

Kyle: um I mean I'd like to say that all the questions have

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a meaning behind them 

Sharon: okay pretend none of your insurance friends are watching this 

Kyle: don't worry none of them will watch this. I think sometimes they ask.

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questions to to get more information around the company that might appear as being useless but they always have a

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have a they don't ask questions that don't have a meaning behind them

Sharon:  so there's always a reason 

Kyle: there's always a reason okay 

Sharon: uh oh you're paying 

Kyle: I'll pay

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oh thank you okay 

Kyle: it's the most I can do 

Sharon: what's what's your password 

Kyle: uh yeah password is

Sharon:  no no okay 

Kyle: I'm now insurable

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Sharon: yes premiums um so they used to be extremely affordable

Kyle: yes

Sharon:  um now it seems

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like those premiums have gone up uh what is going on with that

Kyle:  premiums are a function of the capital deployment costs

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that insurance companies have and then they kind of narrow that down into industry and what the loss profiles look like and then down into the individual

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company itself 

Sharon: okay 

Kyle: and how they're handling their cyber exposure 

Sharon: can you negotiate premiums by the way 

Kyle: 100% 

Sharon: okay so how do you get your premiums to go

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down, how do you negotiate that?  like I understand okay you need to have good privacy posture or privacy security posture Etc

 okay let's bust out the

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fries um but how do you like it 

Kyle: I have to get through all this ketchup that you car there's your ketchup with the side of

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fries french fries, and coffee can't go wrong 

Sharon: Privacy is like a french fry because 

Kyle: it's the perfect compliment for

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your business meal it's that good

Sharon:  I love that

Kyle:  all right there you go

Sharon: um okay so okay how

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do you so give us the tricks how do you um negotiate your premiums 

Kyle: for someone who has never bought cyber before 

Sharon: mhm

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Kyle: are you are you putting ketchup on individual fries

Sharon: yeah how else am I going to do this in the car I wish we oh we do have napkins

Kyle:  what we look for is

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how do we show their policies and procedures and their history in the best light and what resources have they

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committed to their IT systems and also what do they do to educate and train their employees 

Sharon: so you you just have to

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hide all of the breaches that you've experienced have

Kyle:  if you haven't been breached um just wait for it, right

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Sharon: So you're saying it's not a matter of 

Kyle: if 

Sharon: if it's a matter of when someone in your company is going to click on an email

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from the prince of Nigeria

Kyle:  correct okay that that's a great case scenario to say okay let's game this out 

Sharon: okay 

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Kyle: If there was a breach what is your response;  we establish what they do with their actual

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IT infrastructure what would they do with their uh colleagues and how they train and educate them what I like to say is like the best defense against

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cyber uh threats 

Sharon: yes 

Kyle: it’s a really well educated Workforce and a culture of risk awareness so it's the the front end and

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then the back end right if there is a breach how are you protecting yourself how are you responding yeah and that's

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Sharon: Yeah

Kyle: That’s one of the advantages of cyber Insurance because a lot of companies don't have a lawyer on retainer or a PR firm on

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retainer 

Sharon: yeah 

Kyle: but the insurance companies do 

Sharon: this is where we need to like have a conversation, when is it

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a bad idea to call your broker when you may not be sure if you experience a

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breach 

Kyle: never a bad time to call your broker

Sharon: okay 

Kyle: what we can do is let's suppose you think there might be a breach 

Sharon: mhm 

Kyle: but you don't know so what we

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like to do is say hey there's a circumstance that may give rise to a claim that checks the box for notification 

Sharon: okay

Kyle:  and what they would do is then they would say okay give us as

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much information as possible we would intake and manage the claim and probably get our client to

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call. We would call them to the adjuster 

Sharon: okay 

Kyle: and lay out the circumstances and they would say Okay odds are it’s not a

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claim but we're going to deploy resources to help you

Sharon:  will your premiums go up in that situation

Kyle:  well great question 

Sharon: thank you

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Kyle:  um insurance companies believe it or not are there to pay claims right they are we have had

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several insurers pay claims on Cyber 

Sharon: so are you saying that that cyber insurance claims are paid

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more than they're not paid do you have any statistics on this

Kyle:  I do not have statistics on that. Tenai Moyo is our cyber

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practice lead here in Canada she could probably tell 

Sharon: not a shameful plugin she's actually awesome 

Kyle: she is amazing 

Sharon: okay here's another question for you 

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You experience an incident not necessarily a breach yet I report a breach to you or

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an incident you're not contractually obligated to notify the insurer 

Kyle: we would

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take direction from you to say 

Sharon: okay 

Kyle: we have your authority to notify the insurer we would then discuss the pros

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and cons of reporting it versus not reporting it 

Sharon: do you have an obligation to report it to the insurer you must

Kyle:  so,

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Sharon: you can't keep it a secret 

Kyle: well I mean you you can but don't expect to get coverage 3 months later when you're like hey we've tried to figure all this stuff

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out we can't now we're going to claim against the insurance coverage 

Sharon: you know tell me some examples of um breaches or

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incidents that occurred that the insurance company refused to cover

Kyle:  so willful negligence like gross negligence

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Sharon: like what

Kyle:  like telling us that you had  multiactor authentication but in actual fact you didn't have it on certain

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aspects of your business

Sharon: one more example 

Kyle: like notifications, so delay notification so we have had incidences

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in the industry where a client has tried to solve their own problem

Sharon: mhm 

Kyle: and then 6 months later they say okay we have

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tried to negotiate with this bad actor and you know they're not listening to us we can't get them the money we're going

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to get you guys to pay for it now

Sharon:  every time you submit a claim does your insurance go up your premiums 

Kyle: uh not

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necessarily but more often than not yes

Sharon:  hey if you were doing carpool karaoke 

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which artist would you want coming in your car 

Kyle: oh Bob Dylan 

Sharon: oh that's a good one

Kyle:  yeah 

Sharon: do you know why

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so many people love Snoop Dogg's presence? 

Kyle: oh boy this is going to be bad

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Sharon: why cuz he's a great rapper.

 what I've never heard of Quishing

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Kyle: yea

Sharon:  I'm probably like the last to hear of it for those of you like no idea what he's talking about

Kyle:  I'm going to assume your  audience

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is familiar with a QR code 

Sharon: yeah I think 

Kyle: so so you take your camera and you take a picture of a QR code and that enters

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you into a different website a portal whatever and they'll say hey get a coupon.  scan this QR code but behind the

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QR code is actually malicious software that allows them to enter your operating system 

Sharon: oh 

Kyle: yeah and 

Sharon: we're seeing more and

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more QR codes like everywhere like menus QR 

Kyle: yeah your your commercials on YouTube

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right like they'll show an ad for a company or product and next to it is a QR code 

Sharon: you're like on carpool Consulting and there's a QR code

Kyle:  right

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Sharon: yeah pull out your camera let's see let's see is he actually going to do this

Kyle:  it's taking me to a verified email

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address Rick rolls Rick rolls Playbook getting

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Sharon: I hoped you have insurance for that 

Kyle: right this has been going on for years they find the most vulnerable uh place within the

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network to attack

Sharon: okay

Kyle:  and a lot of the times it's actually through the most unexpected ways. there was a um a claim

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in the industry where um they came in through the um IOT connection of the

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company's aquarium 

Sharon: wow 

Kyle: talk about fishing yeah 

Sharon: Ha! oh 

Kyle: yeah we we've seen that and like you know HVAC systems, the

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target hack ages ago actually came through their provider so when we when we have subcontractors who are going

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into large Fortune 1,000 companies they get a a request for insurance right they say they send it to us we review the contract and it says oh you need to

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carry cyber insurance and they're like but we just we're hammering Nails right

Sharon:  yeah 

Kyle: and but the company is so concerned that if they ever plug into a system

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that they're not covered

Sharon:  so so we're going to play game this is going to be so easy for you . don't look at it all right.  on a risk rating from 1 to 5

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one being the lowest five being the highest risk 

your IT guy naps through every cyber security training session

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because he says hackers would never dare target us do we call this optimism or denial 

Kyle: ignorance is bliss 

Sharon: what's that

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Kyle: it's denial denial

Sharon:  so how would you break this you did talk a lot about like the awareness the culture and the training 

Kyle: yeah it's a five cuz cuz that's

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part of the culture and it comes from leaders within the organization and leaders of that IT department 

Sharon:  Absolutely 

Kyle: if they don't take it seriously 

Sharon: no one will.

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Kyle: why should they 

Sharon: yeah all right here we go your office toaster gets hacked because it's connected to the company WiFi and now it's emailing ransomware

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demands to HR; is this a crumb size risk are we looking at a full loaf of one

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Kyle: you're looking at um a full loaf of risk oh yeah and who buys an IOT

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toaster 

Sharon: don't shame those people 

Kyle: don't yuck my yum 

Sharon: yeah yeah okay thank you Kyle this was thanks for the pleasure

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Kyle: Thanks for the lift and for the french fries and for the coffee

Sharon: thanks for covering it all

Kyle:  yeah why am I thanking you 

Sharon: yeah I don't know 

Kyle: well you remember my password

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Sharon: right yeah safe with me

Kyle:  good

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[Music]


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