.png)
The 5 Questions Podcast
Join us as we unlock real estate and business insights, one question at a time.
The 5 Questions Podcast
Think Like A Hacker To Protect Your Business with Sergey Poltev
We Share Sergey’s Journey From A $500 Start To Leading A Cybersecurity Firm, And The Method He Built To Help Leaders Simplify, Secure, And Scale. Clear Stories, Practical Tools, And A Mindset Shift: Think Like A Hacker, Design Like An Operator.
• Immigrant Founder Story And Early Constraints
• Lessons From Facing Physical And Digital Threats
• Plain-English Cyber Risk For CEOs And Boards
• Why Simplification Reduces Attack Surface
• Core Controls: Password Managers And 2FA
• Vertical Integration Across Tech, VA, And Marketing
• Time Audits To Sort $10 vs $500 Tasks
• When And How To Hire Virtual Assistants
• The 3S Model To Grow With Fewer Tools
• AI’s Promise And Leak Risks With Guardrails
If You Enjoyed Today’s Episode, Don’t Forget To Subscribe, Like, And Hit The Notification Bell On Our YouTube Channel So You Never Miss An Episode.
https://sergeypoltev.com/
Sponsored by:
Samuel Castillo & Associates Inc
https://local.cooperators.ca/samuel-castillo-associates-en
Like I always tell clients, you need to start thinking like a hacker if you want to pretend to your business.
SPEAKER_02:Welcome to the Five Questions Podcast where we unlock real estate and business insights one question at a time. I'm Stan Castillo and this is Stan Castillo and Associates.
SPEAKER_01:From home and auto to commercial and nonprofit insurance, Stanley Castillo and Associates takes the time to understand your needs and finds coverage that fits your life and your budget. We're here to protect what matters most, your home, your business, and your family. With life insurance, disability and critical illness coverage, and investment options, we help you plan today for a stronger tomorrow. When life happens, make sure you're protected with Daniel Fuller and Associates. Call us today at 905-978-1721 or email at the address below. An experience that you designed you deserve.
SPEAKER_03:Welcome to the Five Questions Podcast. I am your host, Mario Lamar, and our guest on today's show is an immigrant that turned tech entrepreneur who arrived in Canada with just$500 in his pocket and has since built a leading cybersecurity firm, became a best-selling author, and now helps businesses simplify, secure, and scale through IT, cyber risk, advisory, and automation. Welcome, Sergei Poltav. Hey, did I did I say your last name correctly, Poltav? Sergei, welcome to the show today.
SPEAKER_00:Thank you. Nice uh it's nice to be here. Thank you.
SPEAKER_03:Uh the concept, Sergei, of the podcast is five questions either about business or real estate, and we get straight to the point. You ready? Yeah, let's go. Okay, so first question I have for you. Uh, you're openly mentioned that you came in Canada in 2005 uh with only$500 in your pocket. What was going through your mind at that moment, and how did you stay motivated to build something from nothing?
SPEAKER_00:Sure. Um, well, how did it all happen? Is uh I was an exchange student to the United States uh while I was at school, and I wanted to go to the United States to uh well, I had an American dream. Uh I had a VHS uh player, a couple of VHS tapes, and this is how I grew up uh watching movies, uh, and I always wanted to go abroad. So and so I did went to US a couple of times as a student, and um, but then 9-11 happened and uh and I could not get to the United States, so I looked at the at the map and uh and discovered Canada, you know. So I thought by uh just crossing the border maybe or something, I'll I'll get to US. And the truth of the matter now is I've been to in Canada 20 years now. Um and uh when I first moved here, I thought, I thought, like, you know, I will find a job quickly. And um I didn't I didn't have enough money to to take with me. So uh I had this full of uh ambitions and uh uh risk taking. Um and I I went all in and and yeah, it wasn't easy um because I realized I only had student visa and I thought I'll I'll find a job um somewhere, um a cash job, but it was not that easy. And uh yeah, there's a lot of uh a lot of hurdle came after, but that's what made me who I am today.
SPEAKER_03:And so you you the motivation of success, you I would say uh from what I'm hearing from you, and uh, you know, making a life for you was pushing you to, you know, okay, I got I gotta find a job, but what happened when you did not find a job and and you had to build something?
SPEAKER_00:No, absolutely. Um I really uh struggled in the beginning. Um I I I I was not able to actually work, I had uh student visa.
SPEAKER_03:Yeah.
SPEAKER_00:So the only job I could find is on on the campus of uh of a college campus, even though like even that like it was restricting me for a couple of uh uh you know hours. It's and it's not uh it wasn't not easy. So I I strictly uh I simply ran out of money uh very quickly, uh and uh had no place to live, actually. So I found a play, I have uh I found uh somebody um who uh able to give me a room. Uh and uh um and and then later I I had to like move to the basement of a church. So I was technically homeless, you know. Uh, but that's every single day when I was living at that time, I thought, okay, I need to be successful. I came here for a reason, and um, yeah, and I nobody would hire me because I had no work permit. Not because uh but I had the skills. I was working a little bit under the table uh in the in the restaurant for eight dollars an hour. And uh but but really uh that's what made me an like an entrepreneur. So I started knocking on the doors, finding any kinds of opportunities. Uh I was hungry, literally and figuratively, you know. So I just had to do it, and I didn't want to go back. Um I'm not giving up. I I was very resistant to um to go back, and I just wanted to prove everyone that I can be successful.
SPEAKER_03:So second question, talking about going back, uh, second question I have for you. Early in your career, you built your first business back in Russia, uh, and even faced threats of uh from the mafia. Uh, how did that experience shape your mindset and influence the way you run businesses today?
SPEAKER_00:Yeah, absolutely. So, yeah, running a business in Russia in the 90s or 2000s, early 2000s was very, very uh, you know, uh uh not easy. Uh you you faced uh the there's lots of corruption, lots of uh so it's not hard. It's not it's sorry, it's very hard to to actually run a business. So you have to risk your your life to to do it. Um particularly um the this particular incident when I when I we fa I faced you know mafia coming into the office to my my place of business demanding money, uh it was it's really scary. Uh but it taught me a lesson, first of all, uh resilience letter uh lesson. Yeah, and in fact, this is how I went to cybersecurity um business. Uh yeah I uh I know that most of the cyber attacks happen in Russia.
SPEAKER_03:Yeah.
SPEAKER_00:There's a digital Russian mafia, if you think about that. Uh in fact, Russia and Ukraine are the top two countries for cyber attacks. And what I've discovered is that you know I had that experience in Russia where physical mafia came to me and and uh and demanded the money. And I wanted to fight them, but I couldn't fight them uh because I was just by myself. I had no weapons, I have nothing. But I it I made my life's mission to help businesses and individuals uh that being targeted by a mafia, okay, but in cyberspace. So that's why I went to the cybersecurity, and now I have a cyber company that helps businesses stay away from that mafia.
SPEAKER_03:So the resilience, you you never wanted to give in, and uh you you you found a way to outsmart I outsmart uh the people that were causing you pain. And it's the same in in business today, or even in real estate. You sometimes you have to think outside the box.
SPEAKER_00:100%.
SPEAKER_03:Yeah. Uh question number three I have for you is many people think that cybersecurity is highly technical. How do you manage uh to translate deep technical expertise into simple, business-friendly language that CEO and and boards can understand?
SPEAKER_00:Yes, um, 100%. So I'm actually using um analogy of a hacker. Uh, what I just described to you recently. Um like I always tell clients you need to start thinking like a hacker if you want to pretend to your business. Uh hackers, they have a special, special mindset, uh, they have the tools, they have motivation of getting to your bank account, into your computers. So when I speak with CEOs uh and leaders, I'm trying to explain them that you know um the the ma the the hackers are there doing this for a reason. And just trying to use less technical jargon, really um simple simple, simply is uh I explained them that how hackers operate. Uh that's my my unique ability is to is to translate that in in a simple language. And that's why I wrote a book called Hack Proof. Uh the the word hack means a lot of things, but for me it's it's really the hacker, a bad guy, you know, and he's trying to get into your and steal your information, destroy your company, get your get your money. Uh so and then I teach them how what do you need to do to prevent hacker from doing what he's supposed to do? Uh simple things. And it's and I use the terminology uh like uh of a house. How do you build the house? You need and that which applies to kind of real estate as well. Every business uh to protect the business, you need to put something in to protect it as well, not just build it. Yeah, everybody's focusing on building a business, but protecting it, putting things in place that that make this business resilient from cyber attacks, it's very important. And and I'm trying to use very easy language like a house and a hacker, and that's that's how I do it.
SPEAKER_03:So you you reverse engineer their process and and uh break it down so people can understand. That's that's very smart of you. Um, number four, you've launched different ventures. We talked about your you know IT security firm to AI upskill uh upscaled uh virtual assistant to social impact initiatives. How do you decide which problems or opportunities to go after next? How do you how do you decide, oh, now I'm gonna create this type of business? Because they're not all linked, not all the same subject.
SPEAKER_00:Exactly. So they're not really uh from one uh from first sight, they're not linked, but honestly, there are vertically integrated. So there's a vertical integration. So I'll give you an example. So I I was running everything by myself, uh, was chief of everything officer, uh, which uh brought me to lots of burnout and even uh caused my like my personal life. It was hard, health. My health deteriorated. So I learned that I need to hire more people, I need more help, more support. And that's where I started hiring virtual assistants in the beginning. VA. I'm an IT company, I'm good with technology, but how do I scale my business? Well, I needed more people. Obviously, I'm not just hiring uh VAs, I also hire physical like staff. But for every physical person, we hire three in the Philippines. So my goal was to create a distributed team. So we can work from anywhere, we can service clients anywhere. So it creates this big, big model. So that's that uh later turned into a VA company where we started hire uh offering virtual assistance to our clients. So you can see for my own need, I I created this company. Yeah, then another thing we wanted to I wanted to really give back to society. I wanted to create my own nonprofit, but I learned nonprofits are very hard, like you need to create a board, you know, like so many policies. And but I I'm a good entrepreneur, so I discovered I rather do social enterprise. So I've started social enterprise, another company that helps nonprofits with technology needs. And I I I wanted I created it so I can grow it across North America with the help of my technical knowledge and with the help of VAs, now we have that company, and now we have a fourth company as well, it's not on your list. Uh, it is uh optimized websites, and we're helping organizations with their uh marketing automation, and it's another business, but but it's all uh the reason I went into it because I needed marketing for all my companies. And instead of hiring another multiple companies to manage my marketing, I've created my own. So now we're offering this to outside as well. So all those companies are interconnected, they use technology, they use virtual assistance, they use automation, and now we have four brands. Uh but and I am running this as a as a as a personal brand.
SPEAKER_03:Yeah.
SPEAKER_00:But and and a personal brand grows 20 times faster than physical uh than your business brand. So people when they when they talk to me, they know that Sergei is you know cybersecurity, uh, IT, automation, VA, uh marketing. That my goal, you see, it's all interconnected in a way, vertically integrated.
SPEAKER_03:So yeah, I I I like that. Uh you know, to make sure that people know what you do and what you're involved in is always uh the most important because if it's for their own needs, they'll they'll go to you. If they know someone who needs that, they'll be able to connect uh you with some someone uh that that is in need. Uh I want to uh touch a little bit more on the VA company because I find not a lot of not enough people use the everybody tries to do it on their own and uh to save money. How important is it to delegate I would call it small dollar tasks and high dollar tasks to you know how do you choose what tasks you delegate and and do I need a VA or I I can do it all on my own?
SPEAKER_00:So I I like to do time auditing. Um again, uh being a tech guy, I like to automate this process. You can download a software on your computer that automatically uh tracks everything you do, same thing on your phone. So if you look at your 24 hours, what do you do, Mario, for you? But it can be done for every single person. You know, so first thing is to identify where you're wasting your time. And uh is it are you doing$10 an hour tasks? Are you doing$250 or$500 an hour tasks? You know, so awareness where your time is going, that's the first step. So I often do my workshops are teaching people understanding where their time is going, okay, and how much time they uh they would they they can save. Uh technology tools as well, those are great ones as well, right? So I think that's super important. Then next step, I I try to explain to people what can actually be outsourced. Uh David Allen wrote a great book, Getting Things Done. And David Allen has the workshop and it's free, and you can actually download it online if you Google and you can maybe should put it in the show notes. Uh Google uh incompletion trigger list. Incompletion trigger list. And the first thing that's gonna show up, the first two links are PDF documents from David Allen that will show you what what people constantly thinking about that incomplete. And they always uh like you need to, I don't know, they need to pick up uh the there's a birthday coming up, there is a party, there's this, there's this. Like your time is really wasted on all the all those different uh events. So if you Google that, uh people start opening their eyes. Wow, I have so much things to do, and and absolutely we only have limited time. We have four average person have 4,000 weeks in their entire life. This uh 4,000 weeks entire life. I didn't know that number. Yeah, well, yes, there's uh if you if you calculate that, it's based on uh North American uh life lifespan of 75 years or something like that, or 80 years. So if you if you multiply 4,000, like you find out how many years is that maybe but really that we don't have much time left, and we need to really enjoy the time, we need to go on more vacations, and people need to exercise more, sleep more, and instead they wasting their time on five, ten dollars an hour tasks.
SPEAKER_03:Absolutely, I agree with you. If you can automate or or make the small things come to you instead of you chasing uh for me, I mean it doesn't matter what I do, but for groceries, I don't go out for groceries anymore, it all comes to me. It's it's a task that I don't have the time to do anymore, you know?
SPEAKER_00:Yeah, yeah, absolutely.
SPEAKER_03:Okay, uh last question for you today. Looking ahead five years from today, with rapid advances in AI and cyber threats, what's one big mission or goal you hope to accomplish that could redefine our business approach uh growth and security?
SPEAKER_00:Sure. Um this is what I'm named for. Uh I'm named for um I'm not just an IT guy. I like helping businesses simplify, secure, and scale. And you mentioned that in my in in the beginning, in the title. So I think in five years from now is is obviously the AI will be there. And you and AI will do two things. It's gonna help us, but it will also make us unsecure. There's lots of there's gonna be a lot of information leaked online because people don't know how to use AI properly. They put a lot of personal information. As a security guy, I know that that's that's not a good thing. It's gonna be a lot of hacking going on, a lot of stealing going on. Um, so and I I do recommend like a piece of advice is to really think about um those the 3S model. The 3S model and what I just mentioned. Simplify. The simplify is just remove things that's unnecessary from technology standpoint. Don't have too many email accounts, don't have too many computers, don't have too many different services like you have files stored everywhere in Dropbox and Google Drive and Apple Drive. You need to simplify your tech stack. Uh, there's great CRM systems now that combine marketing, automation, everything. You don't need too many tools. Uh the next thing is secure, secure because in and you need to do it in that order because you cannot secure your environment if you have too too many things. Like if you if you simplify it, yeah, secure it, secure it. Every app you need to secure with the password manager and uh 2FA built in. Like uh, so that's and again, less tools you have. Try to use one email address and and protect that. Don't use free tools, use paid tools, like even it's got five, ten dollars, use that. And next is scale, and scale is very interesting. Once you put yourself for success by simplifying and Securing. Now you can scale your business. Now you can hire VAs and give them access to your tech stack. Now you can use AI better. So I think the this model, uh simplify secure scale, would be very relevant in the next in the next five years because we're going to see more and more tools. We're going to have more cyber threads, and people don't know how to properly scale. So hoping this uh this will give you a note. It's not one thing, but it's it's my methodology, 3S methodology.
SPEAKER_03:Well, Sergei, it was a pleasure talking with you today. Uh, obviously, you're a very smart guy. You uh you know, you understand the IT world, the cybersecurity, you obviously understand business. And I hope that our listeners can uh take a piece of your advice on their journey and help them with in their businesses. So thanks again for being on the show today.
SPEAKER_00:Thank you, Mario. Thank you. Bye-bye.
SPEAKER_02:Thanks for tuning in to the Five Questions Podcast. If you enjoyed today's episode, don't forget to subscribe, like, and hit the notification bell on our YouTube channel so you never miss an episode. Stay tuned for more insights and tips to transform your real estate and business game. See you next time.