Latest / Identity at the Center / #249 - Cyber Insurance with Jason Rebholz of Corvus Insurance and YouTube’s Teach Me Cyber
Transcript
- 0:05This is identity at the center. If it has anything to do with
- 0:10IAM, this is the go to podcast now your hosts Jim McDonald and
- 0:17Jeff Stedman. Welcome to the Identity at the
- 0:22Center podcast. I'm Jeff and that's Jim.
- 0:24Hey, Jim. Hey, Jeff, how are you?
- 0:26Oh, not so bad yourself. Good man.
- 0:28Just getting off a four day vacation, a four day holiday.
- 0:33You know, it was Thanksgiving in the United States and I actually
- 0:36did some cooking, so I cooked a Turkey.
- 0:40I get this. So my younger son, he's 16, he's
- 0:45dead. Everything's really good in this
- 0:47Thanksgiving dinner. But the Turkey's dry like boom.
- 0:54It's definitely. Not good.
- 0:55It's definitely an art to cook a Turkey.
- 0:56I let me think I didn't cook anything.
- 0:59I ate things, I cleaned up. That's usually my what I do is
- 1:02is helping clean, but I also had family in town, so they actually
- 1:06did a lot of cleaning too. So yeah.
- 1:09Yeah, I remember, you know, growing up as a little kid and
- 1:13just like all the men would just go out and watch football and
- 1:16you know, sit there and now it's like you become an adult and
- 1:20you, you have to chip in, man. Yeah, we had a pretty decent
- 1:24turn out, I think. So it was mostly my wife's side
- 1:26of the family. It was actually all my wife's
- 1:27side of the family and my aunt in our place here in North
- 1:31Carolina think it's the biggest gathering we've had for family
- 1:34since we moved here. It was good.
- 1:36We watched football day eight and just kind of connected and
- 1:40talked and stuff like that. People from out of town came in
- 1:44on my wife's side, so it was good.
- 1:46Now I'm taking my niece back to the airport in about an hour.
- 1:49So we want to make sure that we get that like we get wrapped up.
- 1:52So I can send the last of them on their merry way, and then
- 1:55next week and I can actually have maybe more of a vacation.
- 1:58Yeah, well, I think it's like a little taste of the upcoming
- 2:02holidays. So it's always tough coming back
- 2:05to work after four days off, especially when you know, you
- 2:08know three or four weeks into the future you're going to have
- 2:10a a nice couple of week vacation, but still excited to
- 2:14be here doing the the podcast. Just excited to be happy to be
- 2:21alive, Happy to be alive. But yeah, our guest today is
- 2:26pretty special. He's somebody that I've been
- 2:28seeing and following a lot on LinkedIn.
- 2:31He's like a burgeoning industry celebrity.
- 2:34He's got his own YouTube channel and everything.
- 2:36But you know, I don't introduce the guest.
- 2:38That's your job. Yeah, let's let's get introduced
- 2:41in a second. I do want to point out that when
- 2:44people hear this, I will have already attended the.
- 2:47My Identiverse regional event in New York City which is taking
- 2:50place on December 1st, so people here this will be December 4th,
- 2:53but there is another regional event taking place in Chicago on
- 2:56December 5th. So hopefully be able to check
- 2:58that out if you want to get in free.
- 3:01Not that you have to use our link because it's free anyway,
- 3:03but it shows support for our show.
- 3:05We'll have a Bitly link with our codes to be able to kind of show
- 3:08support for that, but I actually had some people ask me if I'm
- 3:10going to the Chicago one because I think people will just assume
- 3:12I'm still in Chicago. And no, I will not be there.
- 3:15I do not live in Chicago anymore.
- 3:17I'm actually going to the New York City one and I will have
- 3:19already attended. So maybe the next time we
- 3:21record, I'll have some thoughts on sort of that conference and
- 3:24what it was all about because I think it's the first time they
- 3:25were doing it. But why don't we get to our main
- 3:28topic? We're gonna talk about cyber
- 3:30insurance. We've got Jason Rebholtz, He's
- 3:32the Chief Information Security Officer at Corvis Insurance and
- 3:35the Teach Me Cyber YouTube channel.
- 3:37Welcome to the show, Jason. Hey, thanks for having me.
- 3:40Thanks for taking the time. Jim mentioned you've got a few
- 3:42different, you know, irons in the fire.
- 3:44It's always great when we see content get on there.
- 3:46I mean, Jim and I are big fans of YouTube, so we're definitely
- 3:48gonna get into the YouTube channel.
- 3:50But we always like to find out, you know, where I guess started
- 3:52from a kind of a background or origin story perspective.
- 3:56How did you get into the field of cybersecurity?
- 3:58Yeah, it was. It's one of those things that
- 4:00was just a complete accident. I I started off early in high
- 4:03school where I was learning how to program and I just was not
- 4:08into it. I mean, I could do it, but I
- 4:09just did not enjoy it. And so my my teacher at the
- 4:13time, who I I still keep in touch with, said hey, you should
- 4:16look at computer networking. And then that led into me
- 4:18discovering the security aspect of it and I just went down the
- 4:21rabbit hole and so. You know, if I look at my
- 4:24career, it's just a a series of just insane timing and crazy
- 4:30opportunities that came my way. And I just jumped on those.
- 4:33And so, you know, I went to school before computer security
- 4:37was a thing. And so I got a background in
- 4:40computer networking, systems administration and security
- 4:44baked into all of that. And then, you know, got my first
- 4:47job at Mandiant. I applied for a job I wasn't
- 4:50qualified for and they just started looking for college
- 4:53hires at that time. And so that really kicked off my
- 4:56incident response career and you know, just completely loved it.
- 4:59And you know, one thing led to another where I did a bunch of
- 5:02startups. And you know, that's how I found
- 5:04myself, where I was building incident response companies and
- 5:08then ultimately got burned out doing incident response and
- 5:11said, you know what, let me give this siso thing a try.
- 5:14And you know, all these things and the culmination of
- 5:17everything I've done in my career really led me up to the
- 5:19perfect opportunity at Corvis Insurance, where I spend part of
- 5:24my time doing internal security. I spend part of my time doing
- 5:28and running a threat Intel team to see where these threats
- 5:31going. And then I spend part of my time
- 5:34supporting our risk advisory team, where I like to think of
- 5:37it as how can we do security for 10s of thousands of companies,
- 5:41really supporting them and their security programs.
- 5:44And so I I'm just somebody that I've got to be doing a lot of
- 5:47different things to really kind of keep myself engaged.
- 5:50And when I found myself leaving the IR world, suddenly I wasn't
- 5:54working 80 to 100 hours a week. And so I was like, I guess I got
- 5:57to fill that time with something and, you know, stumbled into the
- 6:01game of, you know, creating content for LinkedIn and then
- 6:04ultimately YouTube. And you know, that's that's how
- 6:07I keep myself busy these days. So tell me a little bit about
- 6:10Corvus Insurance. Is it a speciality provider or
- 6:13is it a large firm? I don't want to turn this into a
- 6:15commercial, obviously, but help me understand sort of like the
- 6:18position you're coming from and your mindset.
- 6:19As kind of, yeah. So Corvus Insurance is a cyber
- 6:23insurance carrier. So that is what we do every day
- 6:27and it's all we do. And so the cool thing about it
- 6:31is you know a lot of people think about insurance companies
- 6:34and they think of like these stodgy companies that don't
- 6:36innovate everything like that. And so we actually are part of
- 6:40the insure tech industry, meaning we are bringing
- 6:44technology to bear into how do we underwrite risk.
- 6:48And more importantly for me at least is how do we actively
- 6:52manage risk for our policyholders.
- 6:55And so you know part of this is we have an external scan that I
- 6:59know everybody hates. You know it's just a very
- 7:02pinpoint thing in security. We're just looking at the
- 7:04external side, but it's how do we take that information and tie
- 7:09that into the ability to predict the the likelihood of somebody
- 7:14having an incident and the severity of that incident.
- 7:17So it's a security tool in some sense, but you know security is
- 7:22secondary to how do we collect this information, then look at
- 7:25all of the security information behind that and tie that into
- 7:29traditional underwriting practices to really get a tight
- 7:32machine built there. And so, you know, that's kind of
- 7:35the start of it. But where I really nerd out is
- 7:38how do we take this information and really drive the most
- 7:41effective security controls for a policy holder so that we can
- 7:45say definitively, hey, companies that don't have this control are
- 7:49three times more likely to have a security incident than
- 7:52somebody that that doesn't have that or that does have that.
- 7:55And so that's where it gets really fun is you can really
- 7:58drive the conversation forward with data and you're really
- 8:02levelling in the bar and just inching that up and up and up
- 8:07over time until we really just create more secure companies or
- 8:11at least help people get to a more secure state.
- 8:14How much influence do you have on, I don't know, requirements
- 8:18for cyber, cyber insurance? Do you, you know, kind of go out
- 8:22there and say, hey, here's the things that our, you know,
- 8:24policy writers or adjusters or whatever it might be, need to be
- 8:27considering? Do you get involved with
- 8:29questionnaires? Do you?
- 8:31I guess you know, tell me, how much, how much pain do we need
- 8:34to associate with you when it comes to getting those getting
- 8:37those questions filled out? This is the interesting part and
- 8:39I think this is something that nobody appreciates, at least I
- 8:42didn't before I I started at an insurance carrier.
- 8:45And so, you know, I, I came into the insurance industry thinking,
- 8:49oh, we're going to update all the applications and we're going
- 8:52to get all this great data and we're going to make it so much
- 8:54easier for everybody. And then you realize that you
- 8:58are one small player in a very large industry that is doing
- 9:04something the way it's been done for hundreds of years.
- 9:08And so that's where you get. Kind of the, the, the headwinds
- 9:12in the insurance space is it's slow to change for a reason
- 9:15because you know a lot of things they're doing have worked for a
- 9:18very long time. But the interesting thing in
- 9:20cyber is in order to really push the bar on required controls,
- 9:26you have to be somewhere in the same playing field as the other
- 9:29carriers, right? Because at the end of the day,
- 9:31you're still running a business of an insurance carrier.
- 9:33And so if you put too many controls in place or create too
- 9:37much friction on, you know, trying to get a win a policy
- 9:41with somebody, they're just going to go to somebody else.
- 9:45And so it actually is a really interesting forcing mechanism to
- 9:48say what really matters in security because instead of the
- 9:53100 controls that would be on my wish list, you know I got to
- 9:56pick 10 or 15 and maybe I'll get one extra control every year
- 10:01that we want to push. And that's a really good balance
- 10:03between the underwriter and the security teams to make sure that
- 10:07we are being stringent. So it doesn't become, you know
- 10:09what third party risk management is today where you have a
- 10:12questionnaire that's 250 questions long and maybe 15 of
- 10:15those actually matter in the grand scheme of things.
- 10:18And so that's that's kind of the fun of it is you really kind of
- 10:21force yourself to pick the right bets.
- 10:24And you've got this YouTube channel now.
- 10:26It looks like you've been doing it for about a year.
- 10:27How long have you been in the? Cybersec content.
- 10:32You know, creator or game. So it's been.
- 10:35About two years now. I think it'll be two years in
- 10:38February. And it it started when I was
- 10:42building out the threat Intel program for Corvis.
- 10:45Because it's like the the origin story here is I was literally
- 10:49reading a an article on on one of the popular news sites.
- 10:54And I won't say who it is, but I'm reading it and I'm like this
- 10:59is one of the most advanced things I've ever read And I've
- 11:02been in security for a long time.
- 11:04I was like there is maybe 1% of the security population that's
- 11:09going to understand what's being said here.
- 11:11And I and I would go as far as to say the person writing that
- 11:14article had no idea what they were talking about because it
- 11:16was just way too advanced. And so I was like, you know
- 11:19what? I'm reading this and I have a
- 11:21much simpler take on it. And so when I look at my
- 11:25background doing incident response for over 10 years, my
- 11:29whole thing was, how do you take an enormous amount of
- 11:33information from everything that you're investigating it and boil
- 11:37that down into a package that ACEO can understand to make the
- 11:42most informed decisions? And so my superpower really
- 11:45became, how do I take all this technical stuff and decipher
- 11:49that for a less technical audience so that they can be
- 11:52effective in their job. And so I said, you know what?
- 11:55I'm reading this stuff anyway. I might as well just start
- 11:57posting some LinkedIn posts on it.
- 12:00And. And that was it.
- 12:02It started from there. And I started gaining some
- 12:04traction. And then I met somebody, this
- 12:07guy Gary Riddell, who's became a really good friend of mine.
- 12:10And he said, hey, you should, you should look at a YouTube
- 12:13channel. And I was like, you know, that's
- 12:15that seems, you know, ridiculous and whatnot.
- 12:17And so I think it was October of last year.
- 12:20I was like, all right, let me just give this a shot.
- 12:22And I did my first video where I did 0 editing.
- 12:25I was just like, I'm going to do this in one take and just see
- 12:27what happens and then, you know, curiosity gets gets a hold of
- 12:31you. And I was like, all right, well,
- 12:32let me try to edit some of this stuff.
- 12:34And then you learn a little bit of editing.
- 12:36And, you know, I wanted to create some animations to help
- 12:38me better describe some of the technical concepts.
- 12:42And then all of a sudden, you know, you're paying attention to
- 12:44analytics and YouTube and you're like, oh, this video is taking
- 12:47off. Maybe I should create some more
- 12:49videos around that. And then, you know, that's
- 12:51really how I found myself in there is just, yeah, you kind of
- 12:54follow the data where it goes and see what's working and
- 12:57what's not. And yeah, it's been, it's been a
- 13:01crazy journey just learning all these different skills that, you
- 13:04know, you never thought that. That you'd be doing, but you
- 13:07know, here we are. Sounds very familiar story for
- 13:10for us. We could probably geek out quite
- 13:13a bit on sort of you know, producer to producer, editor to
- 13:15editor conversation. But you might have answered the
- 13:19one follow up question that I want to get into and that is how
- 13:22do you choose which content you put out there?
- 13:25Is it the analysts like you mentioned?
- 13:26Because I'm looking at your YouTube channel and you've got a
- 13:28lot of stuff recently around things like pass keys and
- 13:31password managers. And sort of things like that.
- 13:34Are you seeing something in the analytics?
- 13:36It's like, yeah, people are are eating that crap up.
- 13:38We got to put more videos out about it or you know, is there,
- 13:41is there a sort of a method to the madness like how do you
- 13:43choose content? So it it comes down to the
- 13:45platform. Now for for LinkedIn, it's much
- 13:49more around what are current events that are happening.
- 13:52And you know, my system is not complex.
- 13:54I'm. I'm reading the news and when
- 13:56I'm reading something, I typically have some visceral
- 13:58reaction, right. Whether oh, that's interesting
- 14:01or, well, that's not right or oh, this would be, you know,
- 14:04there's there's something to double click on here.
- 14:06And so from there, that's where that's just inspiration for the
- 14:09daily posts. And you know, from there, I've,
- 14:12I've got a newsletter now and I see, you know what, there's
- 14:15something that I want to say more about or you know, there's
- 14:18more to this story than what I can fit in a LinkedIn post.
- 14:21And now I've got some information for a weekly
- 14:23newsletter. I tried that in YouTube and it
- 14:27didn't work at all. And So what what was interesting
- 14:30with that was where it first started taking out, taking off
- 14:34was with the LastPass breach. And so that's when I was still
- 14:39doing my typical process for LinkedIn where she's like, OK,
- 14:42this is a major breach. I'm going to do a YouTube video
- 14:44on it. And you can see it's still early
- 14:46days. I didn't have like fancy lights
- 14:48and all the other, you know, stuff that I have today.
- 14:50And so I just, you know, did this quick recap, doing stuff
- 14:53that I would typically do for LinkedIn, and that video took
- 14:56off. And so I was like, oh, OK,
- 14:58that's interesting. You know, if people are looking
- 15:01at LastPass as something interesting.
- 15:03And I was looking at the comments of people like, oh,
- 15:05what do I do? Which password manager I go to
- 15:07and said, all right, well, maybe I'll just make a video on the
- 15:10best password managers. And then that one started taking
- 15:13off. And so I was like, all right,
- 15:14well, this is interesting. I got some more comments around
- 15:16it and then I stopped listening to it and I was like, I'm going
- 15:19to do all this other stuff related to things that are
- 15:21interesting to me. And those videos did terribly.
- 15:25And so I was like, I think it was probably March or April of
- 15:28this year. I was like, OK, I remember I was
- 15:31literally having this conversation with my wife.
- 15:32I was like, I think I'm just going to go all in on this
- 15:34YouTube thing and just follow where, you know, people want to
- 15:36listen to, which is like the most obvious thing.
- 15:38But again, when you're in the middle of it, no one ever, like,
- 15:40really pays attention to that. And so I put out a video, I
- 15:44think it was on bit Warden, and that just took off.
- 15:46I was like, all right, well, let me just go through and do some
- 15:48more deep dives and kind of see where it is.
- 15:50And that's really what it's been been becoming.
- 15:52And as I look at it, you know, what people are really trying to
- 15:54protect is how do I, how do I authenticate into these?
- 15:58And my password is so central to, you know, my validation or
- 16:02verification of who I am. And then I said, OK, well, I'm
- 16:06seeing this passkey stuff. And I was like, that's the next
- 16:08evolution of passwords. So maybe I'll do a video on
- 16:11that. And that was an experiment.
- 16:13And it didn't really take off until Google came out and was
- 16:15like, hey, we're going to make passkeys default And then that
- 16:17one shot off, right. And so I'm just looking at it as
- 16:21people have this problem today where they have an endless
- 16:25number of websites and applications that they need to
- 16:27authenticate to and no real good way of trying to remember all
- 16:31those things. They're just trying to make
- 16:32their lives easier by like using a password manager or hopefully
- 16:36everyone eventually switches the pass keys so that we can, you
- 16:38know, combine security and usability together.
- 16:40And so, yeah, I'm I'm, that's the vein I've tapped into.
- 16:43Now who knows where it's going to lead?
- 16:44But I think that's the beauty of the data is you just kind of try
- 16:47things out, see how it performs and then lean in where it makes
- 16:50sense. Jason, I really love the
- 16:51channel. I've watched a lot of your
- 16:54videos. I think if you did more gym fail
- 16:56videos, you probably get thousands more subscribers.
- 16:59But. I think stick to this, you're in
- 17:01the right lane. I think people should, our
- 17:04listeners, I encourage you guys go out there and subscribe to
- 17:08the YouTube channel and also connect to to among LinkedIn
- 17:12because you do like like weekly calls and things like that.
- 17:16And it's like, wow, what a great opportunity to learn.
- 17:19And I want to learn from you about cyber insurance.
- 17:23And you know, I've worked with a lot of folks who are responsible
- 17:25for filling out applications for the companies.
- 17:28Trying to figure out, OK, what do we do strategically to better
- 17:32our posture for cyber secure cyber insurance.
- 17:36But what I don't want to do and what I think you do a great job
- 17:39of with your channel is like don't lose people.
- 17:42And I want to start with a very simple question of what is cyber
- 17:45insurance? Yeah, cyber insurance is your
- 17:49way to recover and respond to an incident.
- 17:54And that that can mean a lot of different things for a lot of
- 17:57different people, right. But, you know, take the parallel
- 17:59to car insurance. If you get into an accident, do
- 18:03you want to pay the bills to get that car repaired or the bills
- 18:06for, you know, you know, who knows what that the person that
- 18:09you got into an accident with is going to do?
- 18:11You know, whether they sue you, whether whatever.
- 18:13That is a huge financial impact. And for a lot of people they're
- 18:17not going to be able to deal with that financially.
- 18:20And so you know, that's something where it's kind of the
- 18:22end of the line for them at that point and they may never really
- 18:24fully recover financially from that.
- 18:27And cyber insurance is the same concept when it comes to a hack.
- 18:32And so if you get hacked and you know whether it's a ransomware
- 18:36event where all your systems get encrypted and you need help
- 18:39getting back up and running, whether that's you, you accident
- 18:43your finance team accidentally wired money to Aceo, who was
- 18:47claiming he needed an urgent wire transfer only to find out
- 18:49that it was an attacker located overseas.
- 18:53Those are incidents that can cost you millions of dollars and
- 18:58there's no business that's just going to write that check
- 19:00willingly. And so cyber insurance exists to
- 19:03help offset that cost. And I think that's, that's the
- 19:08pureplay vision of it. But cyber insurance, it's still
- 19:12relatively new in the grand scheme of insurance.
- 19:15But what I personally love is that there's so many other value
- 19:19added things that you can get from that, right.
- 19:21You get access to incident response vendors that have been
- 19:25vetted and know the process to make sure that they're going to
- 19:28give you the best response process that's as efficient as
- 19:31possible and get you back up and running and have little or fewer
- 19:35issues working with the insurance carrier because they
- 19:38have a relationship there. And so you know that's one area
- 19:42you've got in the Insurtech space.
- 19:44You know you've got, you know we're doing scans on a monthly
- 19:46basis for you. We're we're doing dark web
- 19:49monitoring for you to see are you having compromise
- 19:52credentials pop up, is malware installed on your system.
- 19:56And so, you know, these are the type of scenarios where we can
- 19:59get ahead of an incident, I mean literally just the other day.
- 20:02This is just before Thanksgiving.
- 20:04We found that one of our policyholders had their VPN
- 20:08creds that were sold to an Access Broker.
- 20:11We notified them and now they're getting started in responding to
- 20:15that and cleaning it up in their environment before a ransomware
- 20:18event, right? Like those are things you would
- 20:20never think your insurance carrier is going to do for you.
- 20:24But to me, like this is how an insurance carrier really can
- 20:27support you is by giving you these value added services as
- 20:31part of your policy that you wouldn't even know to ask for.
- 20:34Because the whole name of the game is insurance, carriers are
- 20:37there to help pay for a claim when you have it.
- 20:41But it's in both interests to not have a claim in the
- 20:43beginning. And So what can you do with your
- 20:46insurance? Care to try to reduce the
- 20:48likelihood of that that incident upfront.
- 20:49You know, that's that's really where the fun is, at least for
- 20:51May. Yeah, that's a really great
- 20:53point and thought of it that way.
- 20:55It's kind of like how with some health insurance companies,
- 20:58they'll pay for your gym membership, right?
- 21:00If you're working out and living a more healthy lifestyle, you're
- 21:03less likely to need to go to the doctor, get a surgery and things
- 21:07like that. Now, I've heard the saying a lot
- 21:11of times, there's those companies that have been hacked.
- 21:13And those that don't know they've been hacked.
- 21:16Is that true? Because if that's true, then it
- 21:18kind of like, you know, my idea of insurance is that, you know,
- 21:22you get car insurance, everybody gets car insurance, a million
- 21:25people get car insurance and 1000 have accidents.
- 21:28So basically it's the other folks are paying for the
- 21:32misfortune of of a small percentage, but if everybody's
- 21:35been hacked, everybody's going to need to be paid out.
- 21:38That's not a very good position for the insurance company.
- 21:41Yeah, it's, it's one of those things where, you know, I, when
- 21:44I grew up, in instant response, I was at Mandiant when Kevin
- 21:47Mandia used to say it's not a matter of if, but when, right.
- 21:51And so that that had been drilled into me so much that I
- 21:55have dreams of that saying now. And so I I think there's there's
- 21:59truth to that, right? It's not that everybody is
- 22:01hacked at the same exact time and the the challenge here is
- 22:06that you're always going to have some element of evil happening,
- 22:10right. But it's almost like it's almost
- 22:13like bacteria where you have bacteria in your body, but some
- 22:17of that's healthy bacteria, some of it's bad, but it's at such a
- 22:20low level that you're not even going to notice it.
- 22:22And you're you know your typical, your your immune system
- 22:25is really going to be able to handle some of the foreign
- 22:27things that are coming in, right.
- 22:29But it's when something extra bad happens, whether it's the
- 22:32flu, you know, or is it or can we say COVID?
- 22:36Now are we beyond that, where it's OK to use that as an
- 22:38example, but there's things like that.
- 22:40We just got demonetized. Thank you.
- 22:43There are things like that where your body is just not equipped
- 22:46to handle it, right. And so that's when you're going
- 22:47to go, you're going to get some medicine, you're going to use
- 22:49your health insurance, right. So I think it's very similar in
- 22:52cyber where you know you're always going to have some level
- 22:56of something happening, but not every security incident rises to
- 23:00the level of a a catastrophic event.
- 23:04But insurance is meant to be there for those catastrophic
- 23:08events where it just crosses that threshold, where it just
- 23:11like I can't do this by myself anymore, I need some help.
- 23:15And that's when you're going to tap into insurance.
- 23:17So what can cyber insurance cover, or should you look at it
- 23:21as what it can't cover? What's the right way to look at
- 23:24that? The right way to look at it is
- 23:26through a conversation that you have with your insurance broker.
- 23:28So you understand what it is you're buying, right?
- 23:31And I say this is one of the things where I see a lot of
- 23:34organizations get mixed up because they have a perception
- 23:39of what's covered, which is a lot of things, but it's not
- 23:44always the case. And so I'll give you the
- 23:46clearest cut example. So I I Co founded a company
- 23:50called MOX 5 and MOX 5 specialized in what I called
- 23:55ransomware recovery. And so this was when you got
- 23:59into an incident ransomware incident and you needed support
- 24:02getting back up and running, MOX Five would bring in IT resources
- 24:06to help out. They're basically surging your
- 24:08your capabilities to get you back up and running quicker.
- 24:11And so the thing that popped up all the time was that we would
- 24:18get into a situation where suddenly the person who got
- 24:23hacked wants to completely rebuild their network, and they
- 24:25want all the latest and greatest things to rebuild that network.
- 24:30The challenge is your insurance policy typically is only going
- 24:34to get you back to where you were before, just like car
- 24:36insurance, like you get into a car accident, you're driving,
- 24:39you know, a Ford Focus or, you know, Tesla, whatever, You're
- 24:42not going to suddenly be able to buy a Ferrari.
- 24:43Like, that's just not how it works.
- 24:45And so there's just that disconnect where it's just like,
- 24:48oh, well, I needed to do these things to get back up and
- 24:51running. And it's just like, well, hold
- 24:54on, maybe that's not the case. You know, you're really looking
- 24:57at what's reasonable and necessary to get back up and
- 25:00running. And that almost never requires
- 25:03you to build your, rebuild your entire network.
- 25:05And so there are little caveats like that that pop up from time
- 25:09to time. And that's why it's so important
- 25:11for you to talk with your broker to really understand what is my
- 25:15insurance policy cover, is it going to be enough based on my
- 25:18environment and you know what my expected costs are going to be.
- 25:21And so it really needs to be tailored down to to that
- 25:24organization, you know that. And that's especially true in
- 25:27when you're dealing with larger companies.
- 25:29So Jason, talk to us about some of these key factors for being
- 25:34qualified for cyber insurance. I mean, do do organizations
- 25:38sometimes just get? Denied coverage and if they are,
- 25:43you know, affirmed coverage, is it because they have, they're
- 25:47kind of perfect across the board or is it OK to have some
- 25:50deficiencies? This is never a game of
- 25:53perfection. If we had mandated every single
- 25:56control you know across the board that was on the wish list,
- 26:00we wouldn't be in business very long.
- 26:02And so the way that that that I look at it and and this is, is
- 26:07fair to say across most of the insurance, cyber insurance space
- 26:10is there's typically a small number of required controls and
- 26:16these controls will change based on the size of your
- 26:20organization. It will change on the industry
- 26:24that you're in. You know if you're in a higher
- 26:25risk industry, there might have more controls that are going to
- 26:29be required. But typically what you find is
- 26:33there's a requirement for some sort of advanced AV.
- 26:38I'm going to say that generically here because what
- 26:40we're really looking for is EDR and point detection and
- 26:43response. That's kind of the the golden
- 26:45child that we look for. For most.
- 26:48You've got things like backups, secure and resilient backups,
- 26:54and then my personal favorite, MFA for remote access to your
- 26:58environment, for access to your e-mail.
- 27:01And those are, those are three of probably the most common
- 27:04controls you're going to see. You'll see a smattering of, you
- 27:08know, for large organizations, maybe it's going to be a secure
- 27:10e-mail gateway to make sure that we're addressing some of the
- 27:13phishing threats. Some people like to see phishing
- 27:16awareness training and things of that nature.
- 27:18But like the three that I always go back to as being the
- 27:22mandatories, MFAEDR and strong backups, and that's really going
- 27:26to help us deal with some of the most common business e-mail
- 27:30compromise attacks and certainly some of the most common
- 27:34ransomware attacks as well. Now, I know in my past of
- 27:37working with regulators, a lot of times you can say, all right,
- 27:40we are implementing something in three months.
- 27:43A lot of times they went to see that you had a road map and that
- 27:46over time you were sticking to your road map and implementing
- 27:49technology on the insurance side of the house.
- 27:53Does having something in the road map even help?
- 27:57It it can, but it's not something that I would bank on,
- 28:00right. And and the reason for this is
- 28:01because your insurance coverage starts on a certain day and it
- 28:05ends on a certain day, right, typically 12 month period.
- 28:08And so if the intent is that we want to see that control in
- 28:12place and you say you're going to get it done in 30 days, but
- 28:16you don't, then basically the policy was written under context
- 28:22that's no longer accurate. And so sometimes what you'll see
- 28:25is an underwriter will go in and say, hey, we're going to issue
- 28:28this policy contingent on you doing this activity.
- 28:33Well, you know, install and control within a 30 day period
- 28:36and if you don't, the coverage might change, right.
- 28:39And so that's known as the like the industry lingo is that's
- 28:41called a subjectivity, right. And so you see those from time
- 28:46to time. But typically what we know an
- 28:49underwriter is really looking for is does the control exist,
- 28:52right. And can you sign off, Can you
- 28:54attest that it is in place for, you know, all users or whatever
- 28:57it might be? So that's the ideal, you'd say,
- 29:00you know, it's you get into a risky area if you're you're
- 29:03going in where there's too many subjectivities there.
- 29:06Yeah. I'm also wondering like who is
- 29:08cyber insurance for? I'm assuming that large
- 29:11enterprises it's for them. I'm assuming, you know, bigger
- 29:15medium sized enterprises for them.
- 29:17We had Bob Lord from SISA on the podcast and he was the SISO at
- 29:23the Democratic National Conference, DNC and there were
- 29:30less than 200 employees, right? And yeah, and he said we're
- 29:36below the security poverty line. I just love that line.
- 29:40But I'm wondering if you're below the poverty, the security
- 29:43poverty line, is it like cyber insurance isn't for you it?
- 29:47So is there some kind of like breaking point where the size of
- 29:51the organization matters? If you look at it, first of all
- 29:53Bob is, I'm a huge fanboy of Bob.
- 29:56He's he's one of my favorite people and I think what he's
- 29:58doing is amazing. And so anytime he says
- 30:01something, I'm always listening, right.
- 30:03You know as it relates to organizations, you really,
- 30:08whether you're a small business or like an Amazon sized
- 30:11business, right? Like you have to look at cyber
- 30:13insurance because you know even just looking back at my time
- 30:16doing incident response, I would say the vast majority of
- 30:20companies that I was working with, they were sub 200 people,
- 30:25right? And there's always a time where
- 30:28you're working with companies that are less than 10 people,
- 30:30right? And so there's a, there's a
- 30:32reason why there's there's a lot of insurance policies that are
- 30:34sold for organizations that are less than 10 million in revenue,
- 30:37right. And those, those are the the,
- 30:39the organizations that are going to be more susceptible to
- 30:42phishing attacks, right. And so we see a lot of wire
- 30:45transfer fraud in the SMB space because there's fewer controls
- 30:50there, there's fewer processes set up for security.
- 30:54And so things like wire transfer are just more likely to happen
- 30:57there because you're just somebody who's probably
- 30:59overworked and has is wearing too many hats and they're just
- 31:02moving too quick. And so you know for really any
- 31:05business, it's really important to make sure that you're
- 31:08exploring insurance, cyber insurance, it just might, you
- 31:11might just need a much lower limit for your coverage.
- 31:14And so that's where it's less of a question of do I need it yes
- 31:18or no and more of how much is reasonable for me as a as a
- 31:23company, whether I'm, you know, a five person company, even a
- 31:26solo practitioner versus you know a hundred, 201 thousand
- 31:302000, you know, 10,000 plus company.
- 31:33It's just like how much you need to reasonably respond to an
- 31:36incident. That number is going to change.
- 31:38I'm wondering what are some of the mistakes people make when
- 31:42they apply for cyber insurance? I heard you talk about this and
- 31:44I thought the answer was so awesome.
- 31:46Let's see if we get the same answer and if not then I'll
- 31:48produce the the biggest. Mistake that I see is and we're
- 31:53not doing anyone any favors with this by the way, but so many of
- 31:56the applications are yes, no questions and for anyone that
- 32:02has ever filled out a cyber application, it's impossible to
- 32:07answer every one of those questions with yes or no.
- 32:10And it go beyond just cyber insurance like any third party
- 32:13risk management questionnaire, you just can't answer those
- 32:17things because there's insecurity.
- 32:19It's always a well, it depends, right.
- 32:23And you know it's it's just an artifact of the game.
- 32:25It's really difficult to ask a question that's going to
- 32:28encompass all possible scenarios in there.
- 32:30And So what I always tell people is when you're filling out this
- 32:34application, a lot of times this is getting filled out with APDF
- 32:38and there are margins on that PDF.
- 32:41Write some notes in there, right, Because the underwriters
- 32:44see that. And so if you need to expand on,
- 32:48hey, you know, this is what we're doing with MFA.
- 32:50You know, this is what we have rolled out.
- 32:52You know, we're doing X with our our administrators.
- 32:54But you know, for our normal users, maybe we have this right.
- 32:57That is all really important context to give because that's
- 33:02the thing that is lacking in yes no questions is the context.
- 33:05And so I always encourage people make sure that you provide that
- 33:08context within reason. You know, we're not asking it
- 33:11for all your dirty laundry, right.
- 33:13But like give some context there because one, it might get ahead
- 33:18of a scenario where you misinterpreted the question,
- 33:21which happens a lot. And so, you know, that's a
- 33:23conversation that can happen then to clarify that.
- 33:26Or sometimes we see it where, you know, they misunderstand
- 33:30what the control is and they mark it.
- 33:32No, but they actually have it. In fact, they have something
- 33:34better. And so that's the type of things
- 33:36you know have to fill in those margins to make sure that you're
- 33:40really displaying what your security program looks like in
- 33:45the in the most accurate and best light possible.
- 33:48It sounds like organizations maybe need like a Chief
- 33:50Verbosity Officer to make sure that they're answering these
- 33:53questions. You know, it's like when you get
- 33:55you know, if you know you, you're familiar with this as
- 33:57well, right? You do like an interview.
- 33:58It's like, yes. No, OK.
- 34:00Come on man, give me something to work with you, right?
- 34:02Like help me, help you. Jim asked a lot of really good
- 34:04questions and I kind of have a bunch of follow up things.
- 34:07I kind of have been lumping them together.
- 34:09You talked a little bit about sort of like the process of at
- 34:12least at a high level of the incident management like
- 34:14something's happened, right. Here's the things that your
- 34:17insurance provider should be helping with.
- 34:19Can we talk through that a little bit more?
- 34:20I just kind of want to understand, OK, an incident has
- 34:23occurred. When do you get involved?
- 34:26I assume as early as possible. Look, can you kind of just walk
- 34:29me through it? I don't want to tell you a
- 34:30secret sauce or anything like that, but tell me like, what is
- 34:33this, you know, what is the role that you're playing as a cyber
- 34:36insurer with an organization that's gotten?
- 34:38Breached. So the most important thing is
- 34:40to notify as early as possible, right?
- 34:42And so there's a little cheat code that you can use where you
- 34:46can just put an insurance carrier on notice that, hey, we
- 34:49might have an issue at hand here, right?
- 34:52And so that is early stages. You're not providing formal
- 34:56notice or anything like that, but it's just enough to say,
- 34:59hey, we think we might have a problem, what can we do or what
- 35:04should we do right and so. What does that mean?
- 35:07Is that like a legal term notices.
- 35:10Yeah. It's a there's it's a first
- 35:12notice of loss is like that is a legal term in the claims world
- 35:16of like that's the first time that the carrier is receiving
- 35:20information that you have experienced a security breach
- 35:23and are requesting or. You know, basically formally
- 35:26filing a claim with the insurance carrier.
- 35:29So this would be you know the equivalent of with car insurance
- 35:31if you're like filling out the online app to tell them that hey
- 35:34I got into a car accident and I'm looking to seek
- 35:36reimbursement for whatever expenses.
- 35:39So that's like the for that's that's when it's just like, OK,
- 35:42you're officially going to have a claim on record at that point
- 35:45when when you're saying first notice of loss.
- 35:48But if you're just going and saying, hey, I'm going to put
- 35:50you just want to give you a heads up, there might be an
- 35:52issue here. You know, somebody might make a
- 35:54note of it, but you know, it's it's it's just kind of a a pin,
- 35:58if you will, in the conversation until you get more context.
- 36:02Is there a negative thing that can happen?
- 36:05Sort of like, you know, the boy who cried wolf too many times.
- 36:08Is there a spot where it's like, man, this company keeps
- 36:11informing of potential things that might be happening?
- 36:14Does that carry something with it?
- 36:16Or I guess you know, how do you get around that?
- 36:18Like of course you be notified, but you also don't want to.
- 36:21You know, maybe trigger something that might be also
- 36:24negative. I feel like this is, you know,
- 36:26maybe like a relationship between a kid and their mother.
- 36:28So it's like, I don't even know all the secrets, right.
- 36:30But, you know, just tell me the things that are going to put you
- 36:33in jail sort of situation. Right.
- 36:35And it's, it's, it's just one of those things like, you know it
- 36:38when you see it, right. And so it's, I wouldn't say that
- 36:41there's a formal guidance or principle around it, right.
- 36:45But like you know, the general rule of thumb is if you think
- 36:48this is going to cost you money where you're going to have to
- 36:50bring in outside people or you know anything like that or
- 36:54you're like you have some questions of hey, is this an
- 36:56issue or not. It's just better safe than
- 36:58sorry. And most of the time you know
- 37:02it's, it's nothing, right. And the times when it is
- 37:04something you're going to be filing a claim anyway.
- 37:06So it's kind of no, no love loss sort of scenario there.
- 37:10And so you know, come renewal time, the emphasis is going to
- 37:13be on how many claims, actual claims have you had versus when
- 37:17we look at as a carrier, hey, what is our partnership look
- 37:20like? Are you, you know, are we having
- 37:22a two way conversation here where you're really interested,
- 37:25invested in your security program which is going to
- 37:28include when there is an incident just letting somebody
- 37:30know, you know, that goes a long way because for for me at least
- 37:34that's saying hey, you're taking this seriously like this isn't
- 37:38you trying to hide the ball. It's not you trying to, you know
- 37:42paint yourself in a better picture.
- 37:43It's just like the whole point of getting insurance is that if
- 37:46you do have a claim, we're here to pay it.
- 37:47So it's like we'd rather have that transparency then, you
- 37:50know, get the call at 2:00 in the morning that you need to be
- 37:52bailed out of jail sort of situation like just give us a
- 37:55heads up, you're going to a party 1st and you know we'll be
- 37:57ready. We'll have our phone off mute
- 37:58sort of situation here. OK.
- 38:00So we've filed notice. Like what happens next then take
- 38:03me through like so at that point you're getting in touch with a
- 38:07claims manager and depending on your insurance carrier, you
- 38:10might get in touch with a technical resource in addition
- 38:12to that claims manager. You know the claims, this
- 38:14manager is your conduit into the insurance company that you're
- 38:19going to submit your invoices to and the claims managers
- 38:22reviewing those invoices and working on determining coverage
- 38:26and whatever is covered, which is almost you know most of the
- 38:29time it's everything is issuing the payment back to the the
- 38:34policy holder. And so that, I would think of
- 38:37the claims person as that is my conduit into the insurance
- 38:41carrier. And that first conversation is
- 38:44very, very important because they're going to ask you for
- 38:46information of what happened, right.
- 38:49And you're not going to have the full story and that's OK.
- 38:52But the idea is that the claims manager is looking at what is
- 38:56the situation on the ground and what service providers do we
- 39:01have that make the most sense for you, right.
- 39:05And so they're looking at the industry, the size of the
- 39:07company, the threat actor, the type of attack.
- 39:11And we do this enough where we know, OK, you know what, this,
- 39:14this company is this size, it's this threat actor.
- 39:17Well, we just had 15 engagements with this one service provider
- 39:21who has a really good playbook for responding to this type of
- 39:24situation. We're going to give them a call.
- 39:26We're going to put you in touch with them, right.
- 39:28And so the claims manager becomes this conduit where
- 39:32they're really just a facilitator and they're going to
- 39:34say, OK, great, now that we know the details, we're going to
- 39:38recommend to you that you engage with these companies, right.
- 39:41You know, you have a lawyer who specializes in privacy law.
- 39:45They're often times they're called the breach coach.
- 39:47We're going to bring in a forensics provider to do an
- 39:50investigation into it. Maybe we need to bring in some
- 39:53additional IT support for for that.
- 39:56And so they're there to really connect you with them.
- 39:59And so at that point you're going to jump on that call, do a
- 40:02scoping exercise and then you're going to get statements of work
- 40:05from all these service providers direct to you, right.
- 40:08And at that point you're, you're engaged with these providers and
- 40:11you're you have just started the incident response process and
- 40:14you're going through that whole thing.
- 40:16And so as you're going through and responding certain
- 40:20information for invoices and stuff finds its way back to the
- 40:23carrier and you know this is where it's really, really
- 40:26important that. If you're if you're looking at
- 40:28saying, hey, in order for us to get back up and running, we
- 40:32think that we need this big purchase, talk to your claims
- 40:36provider, right. And so like this is where it's
- 40:38just like I can get ahead of some of these coverage issues.
- 40:41You know claims person isn't going to give you a claims
- 40:43decision upfront, but they can really help shape what is in
- 40:47bounds for you, right? And most importantly, what is
- 40:49out of bounds, like avoid these landmines at all costs because
- 40:53that might not be reimbursable. And so as you're going through
- 40:56that process, if you're having that dialogue, you're going to
- 40:59be in a good position to really maximize the amount of money
- 41:02that you're getting back from all these invoices that you're
- 41:05paying out. And so you can't, you go through
- 41:07that whole process and the insurance carrier is there with
- 41:09you along the whole way making sure you're good.
- 41:12And then you know, depending on your insurance carrier, One of
- 41:15the things that we do that I love is we'll jump on a call at
- 41:18the end and say, OK, great, you just went through a terrible
- 41:20experience. Let's just talk about it.
- 41:23And, you know, we have, we can give a little bit more of, you
- 41:26know, one-on-one attention to make sure.
- 41:28Let's talk about your remediation plans.
- 41:29Like how are you doing with that?
- 41:31And all that information can be bundled up to go over the, the
- 41:34underwriters say, hey, like, yeah, they had an incident, but
- 41:36here's all the great things that they did afterwards.
- 41:38And this is how they're they're working to advance their
- 41:40security program. And those are all things that
- 41:42the underwriter will look at come renewal.
- 41:44Because I think it's a little bit of a fallacy where it's just
- 41:46like you have one claim and you're you're out of there,
- 41:48Right. Does it happen?
- 41:50Yeah, sure. Right.
- 41:51Especially if it's a really bad claim.
- 41:54But if you go in and you can show that you're in a good
- 41:57position, underwriters take that in consideration among all the
- 42:00other things that they're looking at.
- 42:02So you mentioned bringing in other third parties into this
- 42:05relationship with the claims adjuster or sorry, the claims,
- 42:09the claims person as well as breach coaches, right
- 42:13remediation response, those sorts of things, large company.
- 42:18Typically you need Msas in place and all sorts of legal
- 42:22agreements. But when you're in the middle of
- 42:23a breach, speed is really one of the things that really needs to
- 42:26be present. How much planning needs to go
- 42:30ahead of time to say, OK, you know, we've engaged this
- 42:34organization to be our cyber insurance provider and oh by the
- 42:37way, you know that cyber insurance provider has this list
- 42:40of different providers that they use, right.
- 42:43And we'll recommend in in a certain case.
- 42:45Do I as the organization go out and say, OK that's great, thanks
- 42:49for advice. Let me go start working on Ms.
- 42:51As and so we have them in place. So it really is just send me a
- 42:54statement of work pre, you know maybe pre approved pricing
- 42:56things like that because I don't know about you but I get stuck
- 42:59in legal stuff all the time with contracts and it takes a long
- 43:02time, you know for for people to to agree on the language right
- 43:07from a convert from a contract perspective.
- 43:09Is that something we should be doing ahead of time?
- 43:11Or are there shortcuts that could be taken sort of in?
- 43:14The moment feel like you were an A+ student because that is
- 43:17definitely like the A+ thing to do.
- 43:20Most companies don't though, right.
- 43:21And so this is where you know, I always, I adapt to Warren
- 43:25Buffett saying of you know save when you can, not when you have
- 43:28to for cyber to prepare when you can, not when you have to
- 43:31because typically by that time you're scrambling.
- 43:32And so that is one of the things that I would definitely
- 43:35recommend is if you have a preferred provider, you know or
- 43:39if you look at the panel and say, hey this is the company I
- 43:41want to work with, just get an MSA or at a minimum just to have
- 43:44your legal team review the MSA ahead of time and just kind of
- 43:47get to the point where maybe you're not signing it, ideally
- 43:50you are and you're good to go. It just helps.
- 43:53It's like it's one less thing that you have to worry about
- 43:56when you're in the middle of it. But that being said, you know, I
- 44:01I did 10 plus years of incident response, 99.9% of the times
- 44:06there was no MSA there. And even for the largest
- 44:09companies you were talking Fortune 500, Fortune 100
- 44:13companies. Just magically when there's an
- 44:15incident, a lot of the barriers that are put in place as
- 44:19protections are dropped. And so you know it might still
- 44:22be a day or two potentially for the especially the larger
- 44:25customers, but a lot of times what you find is like your house
- 44:28is on fire, you're not going to get picky with some of these
- 44:31things and you're just kind of work it out later.
- 44:33You know, it's about how do we get going as quickly as
- 44:35possible, but you can avoid all of that by doing it ahead of
- 44:38time, and it's not that much time up front to save to avoid
- 44:41the potential headaches down the line.
- 44:43It's amazing what happens when when an emergency comes along
- 44:45and really, really lets you really evaluate what parts of
- 44:48the process are immutable and which ones aren't.
- 44:51You talked a little about some of the key things that you look
- 44:54at from sort of must haves. EDR was one of them.
- 44:57MFA backups. What is the biggest bang for the
- 45:02buck when it comes to? Cyber cyber insurance coverage,
- 45:07is it, is it MFA? And I see like that's been sort
- 45:10of like the focus du jour for the last couple years is getting
- 45:13MFA. Is it something else?
- 45:15I guess if I'm just starting to get into this, I need to start
- 45:17building up my case or my capabilities to acquire Cyber
- 45:20assurance. What's the first thing I do?
- 45:22MFA is the de facto answer there, and the main reason for
- 45:25that is because enough underwriters know what that is
- 45:31and can say. Do you have it?
- 45:32Yes or no, right. And again in security, so it's
- 45:36it all depends, right. Like you know how many of you
- 45:38have it deployed to, you know what type of MFA have you
- 45:40deployed. But at the end of the day that
- 45:42answer is going to hold a lot of weight especially as it relates
- 45:46to you know whether you can get covered or not because there are
- 45:48some insurance carriers that are out there that'll say you're not
- 45:51getting the policy unless you have MFA in place.
- 45:54Whereas if you look at EDR and backups, which are still the two
- 45:58that I would say like you know, all three, like you got to have
- 46:01these things, but there's more latitude there, right?
- 46:04Because I mean, we could nerd out for hours on what exactly is
- 46:08an EDR. And you know, just because the
- 46:10marketing team says that it's an EDR provider doesn't mean that
- 46:14it is. And so there's a little bit more
- 46:16latitude there where she's like, OK, you're you're close enough
- 46:19to meeting the definition that it's OK.
- 46:21Whereas with MFA it's like you have it or you don't.
- 46:24And we haven't reached the point as an industry yet which is like
- 46:27this is what keeps me up at night where there's a mandate
- 46:29for phishing resistant MFA. Any form of MFA right now is
- 46:34better than nothing. And so you know that's where
- 46:36focus on that first. If you don't have it, just go,
- 46:40you know, go to the number one spot, get fishing resistant MFA
- 46:43in place, you're going to save yourself a lot of trouble down
- 46:45the line. And so yeah, like all things
- 46:48being equal, start there. Get that out there.
- 46:51It's going to give you the biggest bang for your buck.
- 46:53I thought there's a 5050 shot of you going with backups because
- 46:58it kind of seems like if your MFA is defeated.
- 47:02You know you can do a lot with backups, right?
- 47:05You know you can at least restore your environment if you
- 47:08get breached and they own your active director or something.
- 47:13I mean, even if they give you the key to decrypt things, you
- 47:17might not be able to get it decrypted, right?
- 47:19So having good backups might be the only thing that saves you.
- 47:23I would put that as the third place of the the, the, three.
- 47:27Right. And so the way that I think
- 47:28about it is and this is this is my bias from growing up in an
- 47:32incident response because I think very timeline based and
- 47:38and how an attack progresses, right.
- 47:39And so your front door MFA, right.
- 47:44And it's not going to stop everything, right?
- 47:45But weak credentials, you know, can lead to that account
- 47:48takeover. That's just it's you're asking
- 47:50for a recipe for disaster, right?
- 47:53And then from there, an attacker is going to have to move around
- 47:56the environment. That's where EDR comes in place.
- 47:58So I've got a better chance of of picking that up along the way
- 48:02before they get to an encryption standpoint.
- 48:05And then backups I put as the third because to your point like
- 48:09that is your Hail Mary when all S fails and assuming this is
- 48:12just a ransomware attack, right, when all S fails, your backups
- 48:15are your last line of defense, right?
- 48:17And so it's it's almost like if you look at kind of the aperture
- 48:22of how much stuff, bad stuff that these controls protect
- 48:27against. You know EDR is probably going
- 48:28to have the biggest aperture because you have you're just
- 48:31covering the widest number of types of attacks that you're
- 48:35going to protect against. You know MFAI think that
- 48:38aperture is growing wider especially with the use of you
- 48:40know SSO and things of that nature that are giving you
- 48:43direct access into cloud systems and everything like that where
- 48:46you're getting back into the infrastructure.
- 48:48And then that aperture for the backup, even though it's super,
- 48:51super important, it is very focused on a ransomware attack
- 48:55because now you have a lot of the extortion based attacks that
- 48:57are coming in just stealing data and they're just saying F it to,
- 49:01you know, trying to encrypt, encrypt systems because most
- 49:04people are getting better backups today.
- 49:06And so this is the fun of it. This is, this is going to sound
- 49:10ridiculous, right? But this is the fun of security
- 49:12is it's not a one-size-fits-all T-shirt.
- 49:16And so you really have to look at your environment to
- 49:18understand what controls are going to be most important for
- 49:22me and my environment, not necessarily what you know 1000
- 49:27other companies are saying is that like this is the thing that
- 49:29they paid attention to. So I haven't given this a lot of
- 49:31thought, but I want to make a football analogy here.
- 49:35Aaron Rodgers is MFA and Zach Wilson is, I don't know, a
- 49:39combination of your EDR and your backups.
- 49:43Not very good either of both of those, but man, they put a lot
- 49:46of things into their front door. Now they got, you know,
- 49:50obviously I think everyone knows what happened here.
- 49:52Rogers, he's, you know, kind of gone for the season or at least
- 49:54he's maybe coming back. So it doesn't matter.
- 49:56It's a wasted season for The Jets basically.
- 49:59I guess from a spend perspective, if I take that same
- 50:03analogy, should I spend most of my money on the MFA?
- 50:07Do I spend equal parts 3030, thirty is it, you know, most of
- 50:12it on the first two and sort of on the back end?
- 50:14Because in the real world, every company has budget.
- 50:17You know, decisions to make around this.
- 50:19Where do you see sort of the percentage breakdown between
- 50:22MFAEDR and backups? So it's I would say it's going
- 50:27to be. Dependent on how far along
- 50:29people are are in their journey, I think a lot of people are
- 50:34going to start with some basic stuff with MFA and they'll
- 50:36probably go the free route, right?
- 50:38And so you can get a no cost solution there.
- 50:40It's not the best solution, but it's it's it's pretty damn good
- 50:43right? Especially if you're using, you
- 50:45know, say you say you're using your Microsoft shop, right, you
- 50:48can get some pretty good conditional access controls in
- 50:51place with, you know, even push base so that you've got the
- 50:54number matching, you've got the Geo Geo location on the prompt
- 50:58and so it's not perfect, but it'll get you pretty far with
- 51:02the emergence of pass keys. Now you can even do that for
- 51:05somewhat free, you know, your mileage might vary there, right?
- 51:08So I feel like the return on investment on that is just the
- 51:11time it takes to do it. And that is way worth it, right?
- 51:15With EDR I I like to, I like to push for the the the good ones,
- 51:21right? Because there is a Cliff in EDR
- 51:24where you're buying the marketing data sheet versus the
- 51:28capabilities and so it's something that is still fairly
- 51:32affordable for most companies. You know it, it's per user,
- 51:35right. So it's going to, it's going to
- 51:36add up the larger you are. But you know that's where I
- 51:39would, I would bucket money. You know I don't know what the
- 51:42right breakdown here is but you know I would bucket quite a bit
- 51:46there And then your backups, your backups really like a lot
- 51:50of it comes down to how are you securing it, right.
- 51:52And again it's like this is this is honestly so many things in
- 51:55security like you can you can have a lot of security for free
- 52:01if you just configure it correctly in the 1st place.
- 52:04And so, you know, a good example of this is I see a lot of people
- 52:06go and buy the Cadillac of backups and then they join it to
- 52:11their Windows domain and she's like congratulations, you have
- 52:14just destroyed your chances of securing your network or you
- 52:18know, making a resilient network because now the attacker's just
- 52:21going to log straight into your backup server and delete
- 52:23everything, right. So maybe you go immutable,
- 52:25right? Like it's if you do it the right
- 52:27way, I bucket, you know, say I'm going to make these numbers up,
- 52:31right, you know, 33% of it on on your backup, you know, 30
- 52:35percent, 50% on EDR and what is at least 20% on NFA, right.
- 52:39And if you break down what the actual costs are between all of
- 52:42those, that probably evens out somewhere along there.
- 52:44But it all depends on the size of your organization because the
- 52:47bigger you are, the more storage you need and you know, more
- 52:49robust backup. So that's a very long way of
- 52:52saying it just depends on your organization and you should do
- 52:55them all. I want to ask about rock
- 52:57climbing, but before I get to that, I want a quick take on
- 53:00where you see the future of cyber insurance going, what
- 53:04should. Companies be looking to
- 53:06implement now to keep pace for next year.
- 53:09In the year after that, I feel like Privileged Access
- 53:12Management is starting to see that more involved with
- 53:14questionnaires, So I'd love to get kind of your quick taste on
- 53:17that. And where do you see things also
- 53:19like AI and deep fakes? Are these?
- 53:22Things that we need to be concerned about as, you know,
- 53:24real people in the real world. Or is it still a little bit too
- 53:26far out and maybe it needs a couple more years to break?
- 53:29Yeah. We can do a whole podcast on
- 53:31that one. So you know related to Pam, if
- 53:34you're a large organization, to me that's table stakes.
- 53:37You need that in order to be successful with your IM program.
- 53:41It is a requirement for some carriers and so the larger you
- 53:45are, the more important that's going to become.
- 53:47Small organizations, you're probably not ready for it yet,
- 53:50and honestly like that it's probably a waste of money for
- 53:52you. In most situations.
- 53:53You probably can get away with using an enterprise password
- 53:57manager and just, you know, doing specific vaults.
- 53:59You can kind of hack your way to get to good security for a lot
- 54:03more for something that's a lot more affordable.
- 54:05But once you if you're dealing with on premise environments and
- 54:07stuff like that, it it just it gets way too complicated.
- 54:10Just go with the Pam. So if I have my way would where
- 54:14I think people need to be paying attention to and I where I think
- 54:18insurance carriers need to be looking closer at is phishing
- 54:22resistant MFA becomes mandatory because we're in a period now
- 54:26where we all accept that MFA is really important.
- 54:29You have some some insurance carriers that are mandating.
- 54:31You can't get a policy without that, but attackers have already
- 54:34created ways to bypass weaker. Forms of that SMS, you know push
- 54:39base, token base, specifically a one time password base.
- 54:43There is nothing practical that is bypassing passkeys right
- 54:48anything 502 and so in my in in Jason's perfect world we have
- 54:53every company who buys insurance has a fishing resistant MFA
- 54:57solution in in place preferably something you know passkey based
- 55:00that really puts us them in a position to stop a lot of these
- 55:04these types of attacks that are out there.
- 55:07I think you know with the whole AI thing the the 32nd response
- 55:13on this is I think a lot of the hype is overblown today.
- 55:16Attackers are not using it the way that media is portraying in
- 55:20in in a sense of like you know building these catastrophic
- 55:24abilities to hack into companies.
- 55:27I I think we're probably 2345 years away where we actually
- 55:31start seeing it implemented in the day-to-day operations of
- 55:35attackers. We will eventually get there.
- 55:37I think the beauty of it for most organizations is your
- 55:41defense strategy does not change with this.
- 55:44It just becomes more important that you get more coverage of
- 55:48your existing controls and that you become better at detecting
- 55:51and stopping these attacks before they get to the get go.
- 55:54Because a lot of the AI stuff is just going to drive towards
- 55:56efficiency gains. It's not going to change the
- 55:59playbooks that attackers have been using for the last 15
- 56:01years, because those haven't changed all that much.
- 56:04Yeah, it seems like the the. Playbook is social engineering
- 56:08and phishing, right? As one of the entry methods,
- 56:10right? And you know vulnerabilities,
- 56:12right? You got very few ways to break
- 56:14into an organization. You get that you're you're in a
- 56:17good spot and then the squishy center of your organization.
- 56:21If you have good detection and response capabilities, you can
- 56:24try to get ahead of it before the attacker goes and gets
- 56:26access to Active Directory, gains full control of your
- 56:29environment and then, you know, encrypts your environment or
- 56:32steals data or what have you. OK.
- 56:35Let's talk rock climbing, because I think that's one of
- 56:38the things that you do when you're not doing YouTube,
- 56:41LinkedIn being a seesaw, right? All the different things are out
- 56:44there. I It's been forever since I went
- 56:47rock climbing and I think my rock climbing career consists of
- 56:50a Lifetime Fitness wall about 20 years ago.
- 56:53I'm assuming you do a little bit more than that.
- 56:54Can you take me through sort of you know, what is when I say
- 56:57rock climbing, what does that mean for you?
- 56:59Like what is your normal? Yeah, so I I'm not one of those
- 57:02hardcore people who who go up outside and, you know, everyone
- 57:07always asks me, have you seen Freecell?
- 57:08Like, that's not me. I'm not.
- 57:10I'm not doing that stuff. I I think that's crazy and a
- 57:13little bit too dangerous for me. So I do spend most of my time
- 57:16indoors. I love top roping and lean
- 57:19climbing, which is basically where you're climbing up walls
- 57:21that are anywhere from 45 to 60 feet.
- 57:24And for me, what I love about it is it is the perfect blend of
- 57:30problem solving and puzzles is a lot of to do with security,
- 57:34right, and physical activity because you know, when you're
- 57:38doing it. To I I call myself probably like
- 57:42an intermediate plus climber for if there's any climbers out
- 57:44there like I'm, I'm a 512 climber, which is, you know, a
- 57:47fairly intermediate level professional climbers like at
- 57:51competitions, they're probably climbing 5 fourteens, 5 fifteens
- 57:54like stuff that I can only dream of ever doing.
- 57:57But for me, what I really enjoy is when you reach that 512
- 58:02level, again, it's like intermediate plus level.
- 58:05You have to look at it from the ground and see, OK, I'm going to
- 58:09move this hand here and I'm going to move my, you know, hips
- 58:12in here and do this, this and this.
- 58:14And you're, it's called projecting.
- 58:15And so you're projecting out and like really mapping out.
- 58:18What is your climb going to be? And then you get on the wall.
- 58:21You tend to just forget it all. It's like hopefully it's just
- 58:23like just embedded in your mind at that point.
- 58:26And then you have to put those pieces together and it's to the
- 58:29point where if you're literally off by two inches, you're you're
- 58:33falling off the wall. And so for me, I love that
- 58:36because it gives you the ability to, you know, really put this
- 58:40projection in place. You got this problem solving
- 58:44aspect there and the physical like just draining thing where
- 58:48you're hanging off of just your fingertips.
- 58:51To me, that is my euphoria because it's just it's, I don't
- 58:55think when I'm doing it, you're just acting and you're working
- 58:58on it and you know you're going to fail, Which is the best part
- 59:02because then you can really kind of try these things out and just
- 59:04tweak things over time. And then all of a sudden you
- 59:07know you're you're getting these climbs.
- 59:09And so for me, like that's my kind of analogy for life, is
- 59:13constantly test, experiment, tweak things, try it out, see
- 59:16what works, and then once you have that, it just becomes part
- 59:19of you and you don't think about it anymore, you just do it.
- 59:22So you mentioned 512 which I think is like this climbing
- 59:26measurement system, right? And if I remember this is, it's
- 59:29basically one is supposed to be like flat basically and five is
- 59:33like gear is required, that's like the first number.
- 59:35Am I right on that? The general grade.
- 59:37Typically when you're in a climbing gym, you're only going
- 59:39to see the numbers. Start with A5 and then you'll
- 59:41typically see the grades go from like absolute beginner.
- 59:44Like, you know, children's party level is like a 5-6 and then you
- 59:48get up to the 510. I think 510 is technically the
- 59:52intermediate level. It's like just where your things
- 59:54are getting hard and then once you get to five 11512, like the
- 59:58level of difficulty just jumped so much.
- 1:00:01And so I I've been working on five thirteens for two years.
- 1:00:04And still haven't gotten one right.
- 1:00:06So maybe, maybe this year is is my year for it.
- 1:00:08Who knows? How do you graduate from like
- 1:00:10512 to 513? Is it you complete a 513 and
- 1:00:14that means not you're a 513 Or do you have to like do a certain
- 1:00:17number of them to be like, OK, I'm now consistently hitting
- 1:00:20five thirteens and now I'm yeah, it's not like karate where
- 1:00:23there's like a belt system where like you, you pass a test and
- 1:00:25get it. Someone hands you like a rosin
- 1:00:27bag. Here you go.
- 1:00:27And there's like bowing. And yeah, somebody just repels
- 1:00:29from the ceiling and hands you an award.
- 1:00:32Yeah, it's nothing like that for me.
- 1:00:33The way that I look at it is what can I consistently climb
- 1:00:38and I call it flashing. So flashing is when you you get
- 1:00:42it clean on the first shot and so I can do that for more than
- 1:00:4750% probably close to the 75% of the 512 climbs that I do.
- 1:00:52And so for me it's like OK I I'm, I'm pretty consistent on
- 1:00:55the 512 and so I that's why for me I feel that I'm a I'm a 512
- 1:00:59climber you know 511 is what I warm up on at this point, right.
- 1:01:02And so I wouldn't call myself 511 because of that.
- 1:01:05So it's all, I think it's all subjective and I think that's
- 1:01:07the cool thing about climbing is even these.
- 1:01:09Grades. It's all subjectively.
- 1:01:11There's not an official thing where she's like you have to
- 1:01:13have these three criteria in place to be at this grade.
- 1:01:16It's up to, it's up to the route setter and you know when when
- 1:01:19you get outside. I haven't done this right, but
- 1:01:21it's a little bit of a community thing where you kind of bounce
- 1:01:23ideas back of and forth off each other and you get a just general
- 1:01:27consensus of what it is. And so it's always fun in the
- 1:01:29gym because you'll see, like, the route setter will put it out
- 1:01:32as a 511 and you go and climb it and you're just like, oh, that's
- 1:01:35a heavy, that's a heavy 11, or that's a light 11.
- 1:01:38And you know, some people write on chalk with chalk next to it.
- 1:01:41It's just like you know, 5-10 plus sort of scenario because
- 1:01:43it's just people are built differently and they they're
- 1:01:46good at certain climbs and not at others and and that's the fun
- 1:01:48of it. It's just a very diverse sport.
- 1:01:50I was going to ask if there are controversies in the rating
- 1:01:53system. If it sounds like there are,
- 1:01:55there's that subjectivity to say, OK, my 511 might be someone
- 1:01:58else's 510 or 512, and that consensus is really what kind of
- 1:02:02comes to it. But I love the idea of like.
- 1:02:05Climber graffiti. Like no way this is a 511.
- 1:02:08This is a 510 plus, right? That's what it may be, Jim.
- 1:02:14You're in the you're in the gym quite a bit.
- 1:02:16How do you feel about rock climbing?
- 1:02:18I used to be a a rock climber, but I'm not really built for it.
- 1:02:23I'm kind of a bigger guy and I'd weigh over 200 lbs and that's
- 1:02:28you don't see many like really good climbers who weigh over 200
- 1:02:31lbs. Usually they're they're lighter
- 1:02:33people with really big forearms and like gnarly fingers because
- 1:02:40they've been like jamming their fingers in these like weird
- 1:02:43places. But I have, I've done multi
- 1:02:46pitch climbs and the other thing I don't have going for me is I
- 1:02:50have a fewer fights which I kind of like figured out like as I
- 1:02:54was doing it was like every time I do these climbs I just, I feel
- 1:02:58like I'm going to throw up. It's after.
- 1:03:01Prohibiting, yeah, yeah, It kind of takes the fun out of it, but
- 1:03:06I think it's super cool sport. The reason I really wanted to do
- 1:03:08it was like, I think the lifestyle is like, you know, I
- 1:03:13think of like the hippie climber, like the person in the
- 1:03:15VW bus who just goes around to all these places and does these
- 1:03:18crazy climbs and, you know, they don't have enough money for
- 1:03:22lunch, but they have like. $3000 worth of gear, stuff like that.
- 1:03:26So I'm going to bring up Stephen Sean again on this podcast and
- 1:03:32brought his name up like feels like so many episodes that he's
- 1:03:35over at Octa and he was he's really into climbing.
- 1:03:39He did the the flat face of Half Dome in Yosemite and he said
- 1:03:45that's a three day climb. So you get up, set up a tent,
- 1:03:49like hang off of the wall that that's next level.
- 1:03:53If you have to sleep on a wall, if you have to use the bathroom
- 1:03:57on the wall, like that's that's just too much for me.
- 1:03:59I just, I don't want to deal with that.
- 1:04:00Oh man, sleeping in a hotel bedroom is is enough for me?
- 1:04:03I don't know. Imagine sleeping off on the air
- 1:04:04in a wall. What about you, Jeff?
- 1:04:07I haven't climbed in forever. I am not built like a climber
- 1:04:10anymore. I would say pear shaped is
- 1:04:12probably where I'm at right now. I don't know, I I I was OK at it
- 1:04:17when I was you know much younger and and more in shape and.
- 1:04:21Body hadn't started to breakdown.
- 1:04:22I think it's cool. I have a lot of admiration for
- 1:04:24people who can do it. I live in an area here in
- 1:04:26Western North Carolina. You know, I live on the side of
- 1:04:29a mountain myself, so there's plenty of places to kind of go
- 1:04:32and do this. Yeah, I have nothing but the
- 1:04:34utmost respect for anybody who's willing to scale anything,
- 1:04:38especially, you know, when they're doing it without.
- 1:04:42Things to help them like pulleys and stuff like that.
- 1:04:45Like if you can do that kind of climbing, I think it's really
- 1:04:47cool. I think I think it's just it's
- 1:04:49amazing. And I, you know every once in a
- 1:04:50while I'll see those like YouTube videos where they're
- 1:04:53doing the speed climb up the top and like these got, you know
- 1:04:56these people are going up there. Like, I don't know how many feet
- 1:04:58it is, but they are flying and it's it's nuts to think about
- 1:05:02how quickly they're moving up a wall.
- 1:05:05Where most people are probably like trying to figure out just
- 1:05:08where do they even start, right. They've already projected their
- 1:05:10line, I guess. I don't know, you know, Jason,
- 1:05:12is that something that that you've seen those those videos
- 1:05:14where they're like you know, speed runners or speed climbers
- 1:05:18or what's climbing? So interestingly enough the gym
- 1:05:20that I go to, they they have a team for for kids and it's some
- 1:05:26of the best kid climbers in the in the world or in the US
- 1:05:30trained in this gym. And you want to talk about
- 1:05:33humbling is you know you have some of these kids and I'll,
- 1:05:36I'll sit there and watch them. They'll get up that wall in I
- 1:05:39think the fastest I've seen somebody do and this kid's going
- 1:05:41to be Olympic athlete. I know it.
- 1:05:43I think he got up in like 7 seconds and I don't know what
- 1:05:45the record is. I think it's sub six, but it's
- 1:05:49it's just insane. And that's where like I think
- 1:05:52that's the other thing I love about the sport is it doesn't
- 1:05:55matter what you want. Like, there are just going to be
- 1:05:58some people who are better and the people who put in the work
- 1:06:01are going to see the results, right.
- 1:06:02And so I remember when I first started climbing, I used to be
- 1:06:05really into weightlifting and I went with a buddy of mine who's
- 1:06:08a former Marine Stew, has the biggest hands I've ever met on a
- 1:06:11person. He's just like a complete beast.
- 1:06:13He's just like pure muscle. And you realize that when you're
- 1:06:18that type of body build, you're going to over exert yourself
- 1:06:22right and so. It's not about muscling yourself
- 1:06:25up there. It's about how do you find the
- 1:06:28most efficient movements to get up there.
- 1:06:31And you know when you do it right, it's it's mostly legs and
- 1:06:36you know you can climb forever and just certain slender body
- 1:06:39types, they're always going to be have a little bit of an
- 1:06:41advantage. You know there's a sweet spot on
- 1:06:43height. My My wife climbs with me and so
- 1:06:45she's shorter. I think she's like 554.
- 1:06:49And I'm 511 and you know, we we go back and forth with each
- 1:06:53other because she's like, you only got that because you're
- 1:06:55tall. And I was like, well, you could
- 1:06:56try harder, right? It's just like it's just not
- 1:06:58true. Like some people are going to
- 1:06:59have an advantage. But you know, that's that's the
- 1:07:01fun of it is like you've kind of find your specific area and what
- 1:07:03you love and you enjoy and you can push yourself on other
- 1:07:06climbs. Well, this sounds amazing.
- 1:07:08You make me feel like I want to get out there and I'm not going
- 1:07:10to do it, but you make me feel like I want to.
- 1:07:13Jason, you've been really generous with your time and I
- 1:07:15want to let you, you know, kind of get on with your day.
- 1:07:18We're gonna go ahead and wrap up this conversation.
- 1:07:20We're gonna have a bunch of links in our show notes so
- 1:07:22people can connect with Jason on LinkedIn.
- 1:07:24We'll have a link to your Teach Me Cyber YouTube channel, Corvus
- 1:07:29Insurance, where people want to learn more about what you do in
- 1:07:31in the real world. I'll call it.
- 1:07:34And yeah, for Jim and I, we're on the web, idacpodcast.com.
- 1:07:39We're on Twitter at IDAC Podcast.
- 1:07:41We're on Mastodon. At IDAC podcast at infosec dot
- 1:07:44exchange. Jason, have you gotten into the
- 1:07:46Macedon thing? I have not.
- 1:07:47I was never into Twitter before that collapse, and so I so
- 1:07:52you're. Healthy.
- 1:07:53OK, great. Exactly.
- 1:07:55A little bit of mental extra mental space for me.
- 1:07:57Right on, Yeah. So connect with us on LinkedIn,
- 1:08:01Twitter, et cetera. Like subscribe to show right.
- 1:08:04All the YouTube things are absolutely applicable to the
- 1:08:06podcast space. And yeah, we'll go ahead and
- 1:08:09leave it there. Jason, thank you so much for
- 1:08:10being part of this conversation. Hope you'll come back and and
- 1:08:14educate us some more. And with that, we'll go ahead
- 1:08:16and leave it for this week and talk with everyone in the next
- 1:08:18one. You've been listening to
- 1:08:20Identity at the Center. We hope you've enjoyed the show.
- 1:08:24Make sure to like, rate and review and we'll be back soon.
- 1:08:29But in the meantime, hit the website at
- 1:08:31identity@thecenter.com and find us on Twitter at IDAC Podcast.
- 1:08:39See you next time on Identity at the Center.