Join Leighann Lovely on this episode of the Love Your Sales Podcast as she hosts Ari Milner, a technology and cybersecurity expert with over 15 years of experience. Ari shares insights on how small and medium-sized businesses can protect their digital assets and secure their systems in an ever-evolving cyber landscape. They discuss the critical importance of cybersecurity, practical solutions for IT management, and the intricacies of dealing with modern cyber threats. With real-life anecdotes and expert advice, this episode is a must-listen for entrepreneurs aiming to safeguard their business from digital threats. Tune in now to learn how to build a robust IT infrastructure and ensure your business’s security and continuity.

Transcript:

Leighann Lovely: Welcome to another episode of love your sales I am thrilled today I am joined by Ari Milner, a small business technology and cyber security expert with over 15 years of experience as the founder of PlanIT. He helps business secure and streamline their IT web and compliance needs all while working entirely remotely from Mexico City. Ari is also the president of the Center for Natural Medicine in Portland, a clinic founded by his father in 1991 now managing the clinic with his brother as their father battles Parkinson’s. Ari is deeply committed to helping small businesses whether through technology or healthcare operate efficiently and securely. Please join me in welcoming Ari. I am really excited to have this conversation with you, uh you and I talked previously obviously and um it’s yeah, I’m just I’m really thrilled to have you join me.

Ari Milner: Yeah, thanks so much for having me on yeah.

Leighann Lovely: So why don’t you tell us a little bit more you know what I absolutely love is starting your own business there are so many nuances as an entrepreneur that we do not think about in the beginning, you know we’re like okay I’ve got my laptop I’m armed with you know this product I’m armed with this widget I’m going to go out and people are just going to show up and buy my stuff, there are so many layers that as you all of the sudden become a real company a real boy as I like to say or real girl that we don’t think about and one of those is security.

Ari Milner: Yeah, security, IT, totally this is uh before PlanIT I had a computer repair shop in Portland where I’m from and that’s where I got into doing the business IT managed services and uh started supporting businesses there, um going on site and setting up networks, securing networks, and the landscape has changed so much in the last uh nine years of doing PlanIT that the cyber security needs have gotten way more complex and there’s just so much that you really can’t do on your own as a small business anymore like it used to be that you could just go buy like the Norton or Mcaffee and you’d be fine right but those days are long gone now and like one example is in gosh it was I think about 2018 2019 we rolled out uh Sentinel one as a security service option for our clients and it’s a service that is incredible in with how it’s actually using AI to combat cyber threats and that’s probably the first product in our stack that really had AI as an important component of it

Leighann Lovely: Interesting and you’re right the landscape has drastically changed I remember I was actually talking to my husband and I and we were watching a show from the 90s and there was this you know like big, huge computer sitting in
(05:01) like the family you know room of the of the show of the house that we were watching and it’s like this gigantic computer and I’m like you remember that do you remember when you had that huge computer the dialup and you weren’t worried about somebody hacking in and stealing your information you know the games that I would run home from school and I’m like I’m gonna play a computer game and it was the little the little line that got bigger as it ate the dot on the screen you weren’t

Ari Milner: snake, yeah

Leighann Lovely: Yeah, the snake is that what it was called The Snake Game you know was a Doss prompt in order to get into it? I don’t you know my daughter’s not even know what Doss prompt means and I you know I’d call my mom up and be like okay I’m gonna play this game I can’t remember what’s the Doss prompt to play this game and then I’d have to hang up with her and try it because now I have to use the phone line to dial into the internet that was not security was not an a thing

Ari Milner: Right, yeah, totally and that’s like reminds me of like you mentioned doing that back in the day where you and every end user had to do those kind of prompts but that’s something that we’re still doing as IT professionals writing scripts to run in the background, to automate processes, um and that’s also what AI has been incredible at doing uh in the last couple years with the large language models where it’s a great tool for doing scripts and automation but all of those tools are being used by the bad guys too, right, so it’s a you know a tug-of-war I guess between who can stay ahead uh in order to you know protect systems or attack systems, yeah

Leighann Lovely: That’s totally true what the good guys are doing the bad guys are doing equally as fast to try to basically beat each other out on well how quickly can I break into this system well then that you gotta how quickly can I stop them from breaking into this system wildly interesting completely like I’m glad I don’t have to do that part so let’s talk about how that has changed and how it has changed when you talk with people about the importance I can sit here all day long and be like “Ari, are you telling me that I’m going to have to pay you XYZ a month to keep me secure what I mean come on really I’m a small business owner are people really gonna try to come after me like I don’t have anything that they need?”

Ari Milner: Yeah, totally you may think you don’t have something valuable but even just like your contact list in your CRM or in your email client like any of that can totally be used against you and your clients um your system could be attacked by ransomware is a new, newer more common threat that where you just locks you out of all your systems so then your business can’t function, do you have like insurance for business Interruption do you have backups to get it back because even if you pay the ransom there’s many many cases where you still don’t get anything back after paying the ransom it’s a you’re negotiating with a cybercriminal right so what are the chances that they’re going to even follow through and then even once you do pay say you get it back they still have a copy of your data they could still do nefarious things with it right so yeah it the whole industry 20 years ago um was mostly like you’re saying break fix it wasn’t manage services it was I’ve got a problem my system goes down I’m going to call an IT guy they’ll come out and fix it um they may be able to remote in that was pretty rare back then right um but you would get like a bill for the fix one time but that just doesn’t work for cyber security because we need to be constantly monitoring systems constantly, protecting systems, um like I get alerts all the time for my clients like getting um sign-ins blocked from China or Russia or you know wherever people trying to get in there’s a lot that’s probably happening to you right now and just don’t know because you’re not monitoring it right and that’s where an IT partner like me would come in and make sure you’ve got the policies in place to make sure that even though they’re knocking at the door regularly that nobody’s going to be able to break in.

Leighann Lovely: That’s so scary that’s it’s well okay so here’s perfect example of actually something that just happened to me this weekend I went I took a little mini vacation, I used my credit card um at a little kiosk at in an arcade really quickly just you know reloaded the arcade credits for the girls to go and play games right what a waste of money actually no because they were entertained you know I get to see big smiles or entertained they’re playing arcade games, I slipped it into my pocket we then went home afterwards I then had an engagement where I had to go out that later on that night and I opened up my wallet my credit card’s not in there and I thought oh my God where’s my credit card you know now you do the okay where was the last time I used it oh it was at the arcade okay put it in my pocket it must have fallen out of my pocket because that sweatshirt now has found its way into the laundry and I’m calling my yeah my credit card did you find my credit card so the great thing about you know credit cards nowadays that everybody has apps for them you could literally pull it up in your phone you can turn off your credit card with a click of a button that’s great not you know back in the day you had to track down a phone number you got to call, I was able to turn it off just like that but that fear for that moment is I lost it at the arcade somebody picked it up somebody used it and now I’ve it the numbers out there right you’re talking about an unknown fear of somebody literally just logging into my system and my system houses all of my credit cards possibly my clients’ credit cards all of my clients passwords to anything that I may need to access in order to support them and being that I’m a mark sales and marketing company I’m in sometimes their domains I’m in their the back end of their websites I’m in and all of a sudden that crushing feeling of oh my God uh they’re not stealing my information just they could be stealing somebody else’s information and I would be responsible for that

Ari Milner: Yeah, totally and there’s even like depending on your location there’s different local laws for like breach notifications when you get hacked then you have to publicly tell your clients and report it to the state in many states and there’s a certain different thresholds and windows for that and such but you’re totally responsible at that level and that’s where not just cyber security services come in but like mitigation services like and insurance our latest service we’ve just rolled out this year is a cyber warranty that is actually a third-party vendor who’s connected to our systems and can provide a financial guarantee of up to half a million dollars a year in coverage because they’re saying yes PlanIT is covering our clients and doing best practices right so there’s those kinds of uh levels of protection that you can get in case an incident like this happens and I mean frankly it isn’t really like a an if it happens it’s a when it happens who are you going to be dealing with who’s going to be your IT partner on your side right when something like that happens how much are they going to be able to have mitigated it stopped it you know kicked them out before any real damage could get done right

Leighann Lovely: Right, very interesting and let me just promise this by say I don’t keep credit cards in my system specifically because of that because I don’t know what I don’t know like

Ari Milner: Like you said credit cards are very protected right, but a lot of payments now are happening like with ACH or you know just electronic bank transfers that don’t have that level of security or insurance that a credit card has right so yeah it can be scary

Leighann Lovely: And that’s where you know it’s like okay what information do you want to house on your system because then you become more and more liable for XYZ. So, what do you think the biggest hurdle in your sales process when you’re talking with these small to mid-size companies what do you think for them is the hardest to digest when it’s talking about and this really is about the sales process like you because sitting here and talking to you I’m going okay well fear will drive me to go yep I need you but some companies are just like yeah no nope I’m good I’m good I don’t need that you’re just trying to take my money but what do you say to that how do you overcome that objection?

Ari Milner: Yeah, there’s a few sales tactics we use in IT for that specifically my personal favorite is when I go into a sales call with like a new prospect who I’m not already working with I’m focusing entirely on what their pain points are right and I’m going to sell them on the minimum package that gets them what they need so then we have a relationship and we can build up from there right I can always upsell on more cyber security later right if they’re not seeing the value at the moment and then the tactic to sell them on it later is we actually have a waiver that’s like okay we recommended that you buy this cyber security service you know and or this backup service or whatever you’re opting to not do that we’re not liable for that in case something goes wrong right so separate from all my general agreements that I have with all my clients if they say no to something that I’m recommending that’s best practices I’m going to be like okay you’re saying no sign this please or we’re not going to be able to continue working together right so and that works probably three quarters of the time right they’re like oh okay yikes maybe I will buy this right

Leighann Lovely: Well and it’s funny because it comes down to the same thing of hey, here’s your house here’s the insurance we recommend, and I’ve gone around and around in circles with my insurance agent on and she makes the recommendations and then we go down the list right you know she’s like well I recommend umbrella insurance and I recommend it be x amount and then she’ll go and here’s why because if you have a total loss blah blah blah and then I go oh yeah I should definitely go with the recommended amount because now you understand what the point is you understand the why behind it and now that I’m now that I’ve been talking with you and I and I know other people in this you know in the managed service arena you understand the why and you kind of go right now I get it like but if you’re an outsider looking in going yeah nobody’s ever GNA hack me I’m a one-person show doesn’t necessarily mean especially if you have no security whatsoever you’re an easy pickings

Ari Milner: With AI and automations now a lot of the bad guys are doing stuff where they’re just trying to break in everywhere with the easy method and whatever they can get in and grab it you know it takes them nothing relative to breaking into a bigger corporation so they’ll totally take that and run with whatever they can get

Leighann Lovely: Oh I and I’ve gotten what I think in my career now um I had it was an email of this is an oldie I’m sure that many people out there are going to go oh yeah that one’s happened to me um an email that looked identical to somebody else at my company that emailed and said hey boss can you please update my payroll information my new bank account is and then all of a sudden and it never came from me and then all of a sudden payday came and I’m like is there a reason you guys didn’t pay me this week and they’re like well yeah you emailed us and said you wanted us to update your payroll information and I’m like nope no I didn’t did not do that and it was a really large company and so somehow that made it all the way to HR because the first person didn’t look at the email address and see that it was a spoof email address they then emailed the next person saying hey this information and this was a long time ago when this was first happening and they traced it all the way back to that first person who thought they were talking to me

Ari Milner: Wow, that’s a great example because there’s so many possible ways that could have been stopped along the way if the right technology the right security piece was if there was like a good inbound email security filter it would have just been like oh that’s a spoofing thing and blocked it there right

Leighann Lovely: Correct

Ari Milner: But also like if there was a process at the company that anytime there’s a change you know call the person to verify it right

Leighann Lovely: That one seems obvious

Ari Milner: A super obvious like you know just business process human way to do it right

Leighann Lovely: Or you have to have a signature when a bank information changes it’s like but again this was a really, was a long time ago when people weren’t expecting that nowadays I think that more people are like duh I mean come on but yeah

Ari Milner: And user training too is super important for that too like maybe if that person who received the spoofing the spoofed email had taken some fishing training and realized the method for checking if an email is legit they would have taken the few seconds and been like oh no that’s this doesn’t look right let’s Right double check this yeah

Leighann Lovely: Right and I could go you know on a tangent in a million different directions on why like why would I have emailed you and not gone directly to you know HR when you know you can go in a million different directions but it’s like wow how did that you know and then there were other ones like oh I got a text message that you know directly from the CEO of the company with a link in it saying here can you please click on this and follow the instructions it’s like no first of all it was a CEO that always went by an abbreviated name and they put their full name in there and it was like from you know instead of Rick it was from Richard and it’s like wait you don’t refer to yourself as Richard you know but those are the ones like you either as soon as you click on that link and I’ve again I’ve gotten emails that come through where it really quickly I’ve clicked on it and gone oh no I shouldn’t have clicked on that and immediately notified you know the IT I just clicked on something you’re going to probably want to do a complete now like cleanup of that and I’ve been hacked you know or I at a company I knew that I was the breach right and then did the notification of sorry boss I think I may have just screwed up like I clicked on this link and now we’re and sure enough my clients all started getting these spoof emails from me and I’m like uh you know it’s one of those put your head down and walk out of the office going yeah I just created a storm here yeah

Ari Milner: Well, so I’ll tell you our one breach we’ve had with a client in the last nine years of PlanIT is a tax prep firm and the owner of the firm wanted remote access to their own computers and that’s something we do and set up for them right but what happened is the password they used for that happened to be some password that was exposed in another previous breach and the 2FA wasn’t set up on it on their account it was on our accounts right and somebody got in, we caught them within half an hour like within minutes essentially of them getting into the remote system we were able to block them and kick them out and mitigate a lot of the damage right which we yeah we wouldn’t have been able to do or if they didn’t have an IT partner that couldn’t have happened right if they had just done the remote access setup to their own system and then that happened they would have been like uh oh what what’s going on how do I kick this person out what’s yeah what do we do right so

Leighann Lovely: Interesting. But yeah, how a normal person wouldn’t be able to go in and be like Oh I’m gonna kick you I mean it would be like walking blind

Ari Milner: Yeah but they doing is they’ll just turn it off unplug cables and then they’ll be like okay now what how do I function as a business right

Leighann Lovely: Well, even if you’re unplugging cables though we’re talking about you can’t unplug the

Ari Milner: Yeah, depends on the complexity of your environment right yeah there’s so much yeah

Leighann Lovely: I’m making like you can’t unplug the cloud like everything is now in the like you can’t that’s you can’t I the main server to where everything is housed yeah if you shut that down but I mean my email is shut down right now and I’m barely functioning if you shut down my main server to where everything I’d be like okay I might as well just go and take a vacation because yeah I got nothing to do click on the keys like okay I got a black screen I’ll just pretend to work yeah it’s you shut down one system and you don’t realize until like I have a list of things that I have to do right now that I can’t because I’m in the middle of migrating my email and it got shut down and they’re like oh it’ll be about 60 Minutes you don’t realize how frustrating that is because you’re moving so fast that I never realize that oh I send an email then I go back to something then I send an email now every time I have to send an email I have to write down I have to send this person an email to send this person oh God this is frustrating like now I’m creating a backlog of all of the stuff that I didn’t even realize that I’m constantly doing on a regular so if your main system of something went down your domain your server your whatever the backlog not to mention if there was damage

Ari Milner: Yeah well and that’s what that’s when you want to already have an incident response plan or a continuity and Disaster Recovery plan in place so you know like oh if this goes down then this is what we’re going to do instead right or this is how long it’s going to take to get back up right there’s so many considerations that way and that’s we call it business continuity instead of just backups where we can actually have backup systems that are like extra copies of the system and then the main system goes down we just like flip a switch like kick it over here instead right and then you’re back up and running in minutes instead of like oh sorry it’s going to take 48 hours to do a data restore or whatever and you’re what are you going to do in the meantime right so it depends on how essential the system is what how you need to consider it in the in the continuity plan and what it’s worth you know how much is it worth paying more to have it have a backup continuity system that you can just flip on like that because it’s that essential to your business right

Leighann Lovely: Right, well and it’s funny because you know for the majority of everything else that we have your website for instance you always you have a backup of your website I mean you should if you don’t I mean if you create a website you should have a backup you should have regularly backing that up something happens to your main website you should be able to really quickly just restore that with like the original content and everything else you should have a complete backup of that and you should be regularly backing that up if you’re making any changes if it you should have a backup of all your files or that should be backed up on a regular basis and even you know myself still being a small little shop I still regularly go in and manually do backups of all my files because if my main computer goes down God forbid you know somebody dumps water on my computer or my computer breaks or whatever I have a hard drive an external hard drive that has a mass quantity of space I literally back up everything I’m going to guess that there are a lot of business owners out there that don’t think about that they’re brand new they’re like okay I’m starting and then all of the sudden oh gee I just lost my laptop in fact I was talking to a woman not too long ago who was driving to a meeting at 4:00 in the morning and she got us in a severe car accident almost lost her life we were talking and now she’s getting through the healing process three months later she’s still in still healing from this and one of the things she said to me was my laptop survived and I’m like okay like we shouldn’t be talking about how you’re so thrilled your laptop survived you should have a backup with everything that’s on that laptop somewhere so that if it hadn’t survived your business wouldn’t have completely just gone away

Ari Milner: Yeah, totally the backup’s super important but also the encryption on laptops and mobile devices is important and that comes back to like the reporting requirements like that’s something for HIPPA for example if we’ve got patient information on a doctor’s laptop right and that laptop gets stolen then that has to be reported right but if the laptop’s encrypted when it’s stolen it doesn’t need to be reported they can just buy a new one and be back in business and not have to worry about it because whoever stole it is going to have to wipe it to even use that machine at all so there’s considerations like that most business owners have no idea about that I’m helping educate them on like during the audit or risk assessment process right I recently found I did a security risk assessment with a law firm recently and this exact thing came up I was like oh well we found millions of dollars’ worth of private information on the owner’s personal laptop and it’s not encrypted so if that laptop were to be stolen you would be in big trouble right that’s the kind of thing that we help with all the time so

Leighann Lovely: Interesting, that do you think and this will be my last question because we are coming to time um before you get your 30 second Shameless pitch here but do you think there will come a time where it just as mandatory for everybody to have encrypted devices because of that I mean you my cell phone for instance like yeah if you get my cell phone you’re and you were able to break it Apple is actually quite amazing when it comes to like hey if you lose your password you’re screwed sorry we don’t give out passwords we don’t give pins it’s your responsibility like and there’s been people who what I this whole story about a kid who was playing around and it locked it for like two million minutes or something like there are two billion minutes and then Apple’s like yep there’s nothing we can do for you we don’t that’s great you know like hey you can pretty much know that you’re not going to be able to break into somebody’s phone unless you can figure out the past because it’ll continue to just lock you out so do you think there will come a time when I mean devices it’s just a standardized feature that it has to be encrypted?

Ari Milner: Yeah, well it’s the trend has been going way definitely a lot of services are starting to be encrypted by default like messaging services too right WhatsApp and Signal are doing that right they’re rolling out even encrypted SNS is coming very soon and yeah it used to be that the default when you got a new phone was not encryption and that’s already changed too so but in terms of the requirements it just depends on your jurisdiction like right now the US doesn’t have data privacy and security regulations like Europe does right where a lot of this is mandatory but there’s individual states in the US that do right so it’s the kind of thing where it’ll probably be coming here soon and yeah you’re going to need an IT partner to help you fulfill those requirements

Leighann Lovely: I mean it just makes more sense just in

Ari Milner: One other bit related to that is quantum computers are coming also they’re already here but they’re very uh minimal in terms of their capabilities and how much data they can process but quantum computers can essentially break any standard encryption so and regardless of what your regular your encrypted private key is a quantum computer is going to be able to break into that and get through the encryption there’s newer encryption techniques that have just been discovered in the last couple years that are actually Quantum proof and so that’s really the next level on this story of where we’re going with encryption is we need to get encrypted systems converted over to Quantum proof encryption because 99% of them are not currently and the quantum computers are coming that’ll be able to break into any of this stuff

Leighann Lovely: Okay so you this would be a whole another conversation because you lost me at quantum, I understand at a high level that quantum computers are like next level that I don’t get but I did not know that those were becoming like available are you talking available to like the general public

Ari Milner: Oh no, no they’re not going to be available to the general public for some time but they’re already available for governments and schools doing research on them and large institutions right okay right and they’re getting bigger and bigger and more complex and that’s but that’s one of the first practical implications as quantum computers become more common is standard encryption is not going to work anymore right so yeah that that’s where I was going with that

Leighann Lovely: So basically, the government is not going to be able an encryption is not going to keep the government out of knowing exactly what we’re doing and when we’re doing it

Ari Milner: Yeah, I mean the NSA is going to be buying all the quantum computers they can because they want to break in everywhere and read everyone’s everything right

Leighann Lovely: So, we’ll never be protected from the government basically sticking their fingers in whatever they want to stick their fingers in is the moral of the story yeah they always got to one up us don’t they

Ari Milner: Well but there like I said there is math that is quantum proof encryption that is doable so that would be a whole other conversation we could get into sometime but it’s uh yeah that’s kind of the next Frontier there in terms of data privacy

Leighann Lovely: God that’s so interesting okay well and I would love to continue this conversation because I just I love knowledge and I know that my listeners you know I’m just a total geek I’m a total nerd um I just I love to learn but we are coming to time so 30 second Shameless pitch

Ari Milner: Yeah, so if you’re running a small business, you already know that Tech can either be uh your biggest advantage or your worst nightmare and that’s where PlanIT comes in, we bring Enterprise level IT, web, cyber security, and compliance solutions to small businesses but without that Enterprise price tag. Our global team delivers cutting edge technology trusted by Business Leaders it’s never too early or too late to find the right IT partner if you’re interested come to planitinnovate.com and click the button to book a call with me I’d love to chat with you about your business’s tech needs.

Leighann Lovely: Awesome and how can somebody reach out to you?

Ari Milner: Yeah, my website planitinnovate.com or you can find me on LinkedIn I’m Ari Milner uh A R I M I L N E R.

Leighann Lovely: Awesome, and Ari your contact information will be in the show notes so if somebody is trying to reach out to you can check on the show notes the full show notes are listed on podbean but you can also find that on uh YouTube on the um where our um show is listed on Love Your Sales and the YouTube channel so please go ahead and um you know find Ari’s contact information there but I really appreciate our conversation it’s been fun and just filled with a ton of good information

Ari Milner: Yeah, thanks so much for having me

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