What 20 Years With the Same VA Taught Me About Hiring
17 Apr 2026 · 25 min
In episode 470 of the Secret Sauce of Outsourcing podcast, John Jonas recounts his 20‑year journey with his first virtual assistant, Jovan, whom he hired in February 2006. He describes the initial agency‑mediated search, the steep learning curve for both employer and assistant, and how he taught Jovan everything from WordPress to SEO and lead generation. Over time Jovan’s reliability, willingness to try, and loyalty became the foundation for scaling Jonas’s business, leading to the hiring of additional team members (Paul, Paulo, Jessica, etc.) and the creation of OnlineJobs.ph, an 8‑figure‑a‑year job board. Jonas extracts several lessons: the superiority of hiring “young and hungry” candidates over experienced but complacent ones; the importance of clear, iterative instructions; treating Filipino staff well (flexible hours, fair pay, respect) to foster extraordinary loyalty; the pitfalls of overpaying which can attract low‑quality workers; and the value of investing effort in recruitment. He shares vivid anecdotes—Jovan’s night‑shift preference, a rescue on a banana boat, and the low initial pay of $250 /month—to illustrate cultural nuances and the long‑term benefits of a well‑nurtured remote team.
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I hired my first VA in February of 2006. It's been over 20 years and he still works with me today. We recently celebrated his 20-year anniversary of working with me. Welcome to the Secret Sauce of Outsourcing podcast that's dedicated to making you better at outsourcing to the Philippines. Today is episode 470. My VA has been with me for over 20 years. So in today's episode, I just want to tell a story and hope that it illustrates some points of what you might experience with the Philippines. So the first person I ever hired, I hired him in February of 2006. His name is Jovan, and I had actually started the process in December of 2005. Just recently, because we were celebrating his 20th anniversary working with me, I went back to my email and I searched Jovan. I searched his name and found the earliest, earliest communications I had with him, which was in February of 2006. Now, I had actually started the conversation in 2005, in December of 2005, with this agency who was going to find someone for me. I started in December. We went back and forth for a while. They were like, oh, we're actively recruiting people right now. And I was like, okay, well, I'll take someone. They're like, okay, well, here's 3 webmasters. And they sent me some people and I was like, I mean, I don't— yeah, I read like their articles that they had had them do a test and I read the articles and they just were not good. And so I was like, I think I'll wait. I'm okay waiting a little bit. They came back to me a while later like, we've gone through our recruiting process. I think they were just actively recruiting for whatever, whoever they could find for whatever clients they have. They weren't specifically recruiting for me. They were just bringing people in, whatever. And they sent me these profiles and one of them was Jovan. And I was like, I'll take Jovan. That sounds great. And they asked me, well, would you like him to work on your hours? And I asked, well, I don't know, is that okay? And they said, well, many people prefer to work at night because it's hot in the daytime. I was like, sure, that's fine. Which there's another story coming with that later in this podcast. I get referred Jovan to me and they're like, okay, you can start communicating with Jovan and every day Jovan will send you a daily report and he'll also send it to us. And so I'm getting these daily reports from Jovan and he's also sending it to them and I'm responding to Jovan and to them, this the agency owner, whatever. Here's what happens with Jovan. When I first hired him, Jovan knew nothing. Like, they had pulled a warm body off the street. Jovan, later he told me, sir, when I started working for you, I was so scared. I didn't know anything, but then you were kind to me and you started teaching me things, and I was like, well, I'll just do it. Which is exactly my experience on my side. Like, I didn't know what I was doing, and I hired him, and He didn't know what he was doing. And pretty quickly I was like, you're not really a webmaster, but I can teach you some things that I understand. Like, here's how WordPress works, right? Like, at the time, this is 2006, WordPress was fairly new. There wasn't like YouTube tutorials you could go watch. Now you send someone to YouTube and be like, hey, watch these YouTube tutorials about WordPress. At the time it was like, okay, well, here's how WordPress works and here's how I want it to work and here's what we're doing. And I taught him that, right? And I was like, oh, here's how you do this article marketing. There wasn't anything good about it. I was kind of inventing how article marketing should work at the time. And I was like, okay, I want you to write articles. I just taught him these things and he went and did it. And one of the amazing things about Joven was he was always willing to just try. He would do his best. It wasn't always great. It wasn't perfect. Often it wasn't what I had hoped for, but he was still willing to like put in the effort and do something about it. Like go out and try and write the article and get it completely wrong. And I remember the first time we wrote a specific type of content that I had him write, I was like, oh, this is bad. I don't know if this is going to work. This is, I don't know, 18 months into having him work for me. Even then it was still like, oh, that was really bad. So then I was like, well, I'll just change how we're doing this and see if I can make it work. And I gave him some more instructions and he tried it again and it was still not great, but it was getting better. And I was like, okay, well, we got to tweak this and this and this. He tweaked this and this and this. He'd always follow, right? And I learned over time, over a long time, I mean, this probably took me 10 years to realize. That my instructions aren't that great. And that's one of the things that I want you to take away from this is your instructions probably aren't that great. I thought my instructions were really great. I've thought that a lot of times over the years only to find out, oh yeah, my instructions actually really sucked. And I've seen that a lot of times from other employers. And I learned that because Jovan was patient with me towards being like, I tried this. Here's what I did, sir, based on your instructions, I did it. And I'm like, you didn't follow my instructions at all. He's like, well, you said to do this and this and this. And I'm like, I did? That's what I said? He's like, yeah, watch your video. Like, here's the video that you made. Like, okay. So that's been really good because Jovan would always try. He also always showed up, man. It has been over 20 years now and Jovan shows up every day. And to the point where like, if I don't see something from Jovan, well, I'm not worried because I know he's going to show up. But I'm like, wow, something must have gone on with him today, which is so amazing to have someone who just shows up every day and who's interested and who wants to help. And what I've seen over the years is I have a lot of people like that. I have a lot of people that show up every day and they want to help and they want to contribute. And Jovan was just the first. So he starts writing this content for me, starts managing my blog, in WordPress. And because I was having such success with him, I mean, this is where I felt like there were 2 of me. For the first time ever, I was like, I'm actually productive on this and this and this because I have him doing this and this and this. And after a number of months, I was like, this is going really well. I want to hire someone else. So I went back to the agency and was like, well, let's hire a programmer now. And they found me Paul who also works for me. Paul spent some number of years away from us and then came back and he worked for us again 20 years in. And so with that, because I was having such a good experience with Jovan and then also again with Paul, people started asking like, hey, how are you doing this? What's going on here? How are you having such success? How are you finding these people? And I was just telling people, these are mostly my friends, some people in a mastermind group that we had calls every week and people would ask every week, like, what's going on? How's this working? What are they doing for you? Every single week they're asking like, well, how did you do that? Well, I just asked them to do it and I gave them some training and Jovan just did it. So a few years in, they're like, well, come teach my audience this. And so I started teaching their audiences this, and this is all based on Jovan, right? Jovan, my experience with Jovan, and then my experience with Paul and my experience with Paulo and Jessica and Which all of them still work for me today. And so in 2007, I start teaching this. In 2008, I'm like, this sucks to find people. I think there's a better way. And so I was like, hey, Paulo, who worked for me on a car insurance website that I had out of the Philippines. Well, the car insurance site wasn't a Philippines website. It was actually ranked number 1 on Yahoo and Google for the word car insurance. Because I had people doing the SEO like Joven was doing the SEO and I knew exactly what needed to happen. It's just, it had to happen, right? And so I was ranked number 1 for car insurance, like outranking Geico and Progressive and all of them, right? And so I was like, hey, Paulo, let's build a job board and maybe then people can find, maybe I could recruit someone else because I was tired of going back to the agency. It wasn't even people, it was myself at the time. Let's build a job board. And let's see if we can get a few hundred people into this job board. And so Paulo builds this thing. It takes us a year, but OnlineJobs exists because of Jovan, because I had this amazing experience with Jovan where it was like there were two of me. And then I had this amazing experience with Paulo. It was like there were three of me, where he was doing the programming that I was previously doing, which I was able to do more programming because Jovan took such a load off of me on other stuff. And then Paulo starts taking a load off of me on programming, so I'm doing other programming, and I hire Paulo, programmer. That was the last time I did programming. Was like 2007. So Joven starts all of this in February of 2006. And now it's February of 2026 when I'm recording this. And he still works for me today, but now he manages OnlineJobs.ph, which is an 8-figure-a-year business. And Joven is, he's not running it because I'm still the CEO, but I tried to give him a title recently and he turned it down. I was, I tried to give him the VP of Operations title. And he was like, no, I'm not at a VP level yet. I need to do more. All right, cool. So he's taken on more responsibilities, checking on things. He's managing more processes for us. It's super amazing. So in all of this, there's a couple of things that I think are important lessons that I didn't learn from Jovan, but I kind of did. I just didn't realize it at the time. Number 1, well, at the time there was no way to hire someone experienced. There was no way to get in contact with people. I just had to go through an agency and they just pulled a warm body off the street, which is generally what agencies do today. They just pull a warm body off the street. They'll tell you, oh, we'll hire the top 1%. Yeah, that's garbage. And what was really amazing was Jovan was young and he was hungry and he wanted, he wanted to contribute. He wanted to learn. He wanted to work. He wanted to earn. He wanted all that stuff, right? Over the years I've learned there are two types of people that you can hire. You can hire a young and hungry person or you can hire, I'll just call it an experienced person. And Usually I prefer to hire a young and hungry person, and I still to this day prefer to hire young and hungry because they want. And an experienced person is often tired and they don't necessarily want. They want you to pay them. But Jovan wanted to learn and Jovan wanted to understand and Jovan wanted to get involved and he wanted to contribute. And I still see that. I see that with so many people. But that is a key takeaway out of this whole story was young and hungry is really amazing when you're hiring. Even if you think, oh, I need someone that's super experienced with GoHighLevel or super experienced with Facebook marketing or whatever it is, you, you probably don't. And this goes for like video editing where you're like, oh no, I definitely need someone who's super experienced. No, you probably actually don't. You need someone who's young and hungry and who they already understand Adobe Premiere or they understand CapCut or whatever it is, and they're like, yeah, let me try this new thing. Where someone experienced, they're like, well, you know, like, this is how I do it, right? This is the way. And someone young and hungry, they're like, no, I want to try this. No, hey sir, I tried this thing today. No, I want to try this. Hey, I watched this video and I saw these guys doing this and I want to try that. I'm going to do that. And that's what you get with young and hungry. Okay, so the next lesson in this was I taught Jovan almost everything he knows. When I hired him, he knew nothing. And he, like I said, he told me that. And I just started brain dumping on him. And it was brain dumping one thing at a time. It was SEO, like, here's what I understand about this. It was lead generation. Here's what I understand about this. I never brain dumped on him social media marketing because I don't know anything. I never brain dumped on him programming, although one time he started learning programming because he was like, I think I could contribute more if I knew some programming. But I taught him all of these things across our business. And it would be like the equivalent of if you're an insurance agent and you're teaching someone how to do lead generation. How do you guys do lead generation? Well, we send out these postcards. Well, we do, we contact local people on LinkedIn. Well, we participate in these local groups. Well, we go to this Chamber of Commerce thing and we pass out these flyers. And it would be like teaching him, hey, here's how to make these flyers that we're going to pass out at the chamber. Here's how I stay in contact with all of my contacts and remind them that I'm here, right? Here's, here's my database. Here's how I manage this. I'm going to teach them that. And I'm going to teach them this lead generation thing. Here's how we reach out to people and just let them know. Here's how we design this billboard for whatever we're doing, right? I was just teaching him all of these things. Here's what happens when we get a claim. Here's what happens when we get a new client and we need to bring them on board. And we go through all these questions with them. Here are the questions we ask. Here's our questionnaire. And here's the email that we send to them. I just taught Jovan all of these things. And over time, Jovan just took all of those things off of my plate. And then when we hired someone new, someone who wasn't a programmer, because Jovan wasn't a programmer, I would hand them to Jovan and be like, hey, you're doing this process now. I just hired someone else to help you with this process. So you teach them. He'd be like, okay, sure. And he taught them the process. And then since then, so like he taught Jessica and then Jessica has since taught, gosh, I don't know, Jessica's brought on board like 8 or 10 or 12 people and taught them. And she's now managing people who are managing other people within our organization. And yeah, I hired Jessica. I was just looking at all these emails. I went back through my email and searched, I searched Jessica and found the email from the first email I had. With her, which is 2008. And now she's managing Jehan and Princess and Mark and May and all these people. And she learned it from Joven. So in 2008, when we launched OnlineJobs.ph, which was 2009, when we started building it in 2008 and launched in 2009, that's because of Joven. Like I started OnlineJobs because I had had this amazing experience because of Joven. And then all these other people that I was talking to about it were also having this amazing experience with their first hires. And I can't even tell you how many times I heard the same story. Almost the same wording. Oh, John, I got so lucky with my first person. Oh, you did? Really? Because I've heard that from 30 other people in the last 2 months. You got so lucky with your first person. I got so lucky with my first person too. And thousands of people have gotten so lucky with their first person. Now, having said that, I don't want you to think that everybody has an amazing experience the first time because it's not— that's not the case, right? If you put very little effort into your recruiting, usually you're going to get very little out of it. It takes some effort to recruit someone good. And especially if you're like, no, I just want to pay more and I'll get a better person. Well, I was paying— gosh, I just looked at this. I even had the numbers wrong. I was paying $525 a month to this agency for Jovan. And I didn't know this at the time, but they were paying him $250 a month for full-time work. Which, $250, full-time work is 172 hours a month. $250 divided by 175 is definitely under $2 an hour. In fact, I think it's under $1.50 an hour. So Jovan was making less than $1.50 an hour. Now this is 2006. Stuff has significantly gone up, but like doubled, right? So $3 an hour would be what Joven would make now in like the total newbie beginner space. And I just lost my train of thought with where I was going with that story. But here's another piece that I want you to understand from this whole thing is Joven still works for me today and Paul still works for me today and Paulo still works for me today and Jessica still works for me today. And Jessica referred her sister Julia, which you've seen Julia. She writes the newsletter. Filipinos are super loyal when you treat them well. But that's the key. You have to treat them well. And that was one of the things that I did with Jovan. So going back to the very first thing was, do you want him to work for you at night? And I was like, sure. And so a couple months in, Jovan comes to me and says, sir, I hate this. I like working for you, but I can't work the night shift. It's killing me. It's so unhealthy for me. It's hard for my family. "Could I maybe work daytime hours? Because the things that I'm doing aren't dependent on it being nighttime and we're not communicating in real time." And I was like, "Oh yeah, absolutely. You can definitely work your daytime. You don't have to work at night." And he was like, "Thank you so much, sir. That's such a big deal." And from then on, Jovan has worked daytime hours for him, nighttime for me ever since. And that was when I learned, oh yeah, the night shift is hard. So some people prefer to work at night because it's hot in the day in the Philippines. But I still just give them the flexibility of allowing them to work whenever they want. My whole team is like that. They can all work whenever they want unless they're on a specific customer service shift or we have to cover specific hours. So yeah, Filipinos are super loyal and if you treat them well, so that was a story of me treating him well, like, yeah, you can work whenever you want, then they'll work for you for as long as you're willing to provide a job, which is a really big deal, especially for a small business when like turnover is the worst case scenario. And I've just had very little turnover over the years. And Jovan has had a good amount to do with that. He's always watched over other people and taken care of people. So let me tell you another story about Jovan. I've been on this really high with Jovan this week because 20 years, you work with someone in the US for 20 years, that is so long. And yet I've worked with him for 20 years. I've been to the Philippines one time. It was in 2010. I took my family on vacation. We sat on the beach on the island of Boracay for 5 weeks. And at the time, I think I had 6 or 8 people on my team and I brought them all to Boracay so I could meet them and we all spent like 3 days together. And during those 3 days, one of the things we did was we got on a banana boat which is an inflatable thing that looks like a banana. They paint it yellow and they tow it behind a boat in the ocean. And if you've ever been on a banana boat, they're super sketchy. If you flip it over, everyone's getting hurt because you have 8 people all together hitting the water at the same time, going 20 miles an hour, and knees and feet and legs are flying everywhere, right? So we did this, but none of us had ever been on one before and we didn't know. They're all actually like kind of scared. And I didn't know this at the time, but I don't know how many of them actually knew how to swim. But I know Paul did not know how to swim. And which is, this is really interesting. Like the Philippines is an island nation of 7,000 islands and you don't know how to swim, which yeah, that was the case. They didn't know how to swim. So we get on this banana boat thing, which they all think is just a ride. And I'm having fun with it. I'm jumping all over the place and tipping it and pulling it sideways. I finally tip it over and everybody goes flying. And we come up and Paul is freaking out. I look over, I see Paul freaking out, and I see— I look the other way and I see Jovan sprinting to Paul. And we all have life jackets on, but Jovan is like, "Bah!" Like getting over to Paul and grabs him and is like, "You're okay." It's okay. I didn't know that Paul didn't know how to swim. I don't even know how many of the rest of them don't know how to swim or didn't know how to swim. But Jovan knew that Paul didn't know how to swim. And Jovan's first reaction was get to Paul and help him. And that's what he did. Jovan took care of Paul. And over the years, Jovan has taken care of me. And I am just so thankful to— to him, to the culture of the Philippines that allows him to still be working with me for 20 years later. I'm thankful that I was willing to teach him things that I was not willing to teach previously. I wasn't willing to teach it to someone at Upwork because I tried that. I wasn't willing to teach it to someone locally in the US because I knew they weren't going to work for me for 20 years. That wasn't a thing. And I had no idea that Jovan was willing to. But I knew that he was affordable enough that I could probably pay him enough to keep him with me, which was the case. So, okay, so this is the story that I was going back to with— I remember now, Jova was making $250 a month. And often we think, oh, I'll just pay more and get a better person. And what you miss with that is you miss the stage of someone learning your business, someone who's young and hungry and willing and eager. And you get someone who's experienced and they've been through this with someone else, and they're like, oh no, I understand now how things work, and I know that I can get paid more. And if you're not happy to pay me more, I'll just go somewhere else. And so I get this attitude often from employers that are like, oh no, I'll just, I'll pay $10 an hour. I'll hire the best person. And then they end up complaining to me saying, oh, Filipinos suck. Like, well, actually you overpaid. When you overpay, you attract bad people, which is not what you would think, but that's my experience. You overpay, you attract not great people. And at the time, I didn't have this opportunity. I didn't have the option to overpay. I just had what I had. And I got Jovan, right? And then all the rest of the people, well, some number of people came through an agency and then we started OnlineJobs and we started being able to find people on our own. But at that point, I already knew like, okay, well, here's the current rate that should be paid. And I never overpaid it. Never had that ex— I mean, not that I haven't had the experience of someone being like, well, I'll work multiple jobs because I have had that experience. But I haven't had the experience where like I hired someone and that person was already working 3 jobs. And like that just hasn't been the case for me because I know I'm not offering $10 an hour. Like I'm not a— I probably am, but I try not to be an arrogant American like, oh, I can afford that. I can just pay more. And that was a lesson that it didn't come directly from Jovan, but it came from from lots of years working with him and then with other people and really him correcting me across the years, like, sir, this isn't the right way to do this. You shouldn't do this. And I'm like, well, I think it is. And then later it'd be like, oh yeah, you were right, actually, Jovan, thank you. So thank you, Jovan. He probably won't listen to this, but this is the experience that you can have when you hire someone in the Philippines, when you're willing to put in a little bit of effort to find someone. And like I said, I didn't put in any effort, because at the time that wasn't an option. Today, I hire people like Joven all the time. I hired someone like Joven yesterday to be on my SEO team. And it's just not that hard to find people when you spend a little bit of time recruiting, you use the AI matcher, you see what they look like and you don't go overboard with like, oh, this person is like the dream, dream, dream. Because that's not, I usually am not hiring the dream, dream. Like if they're too good to be true, that's a red flag. Joven was definitely not that person. Neither is Matt. Giselle, who I just hired yesterday, she's not there. Her English is perfect. But she has some Philippine-isms that are like, okay, this is not what I want putting forward to an American audience. But she can correct that. And I told her that. And she knows right away that I expect improvement. And Jovan knew that too, because I was willing to teach him stuff. And I'm thankful that I was willing to teach because He was willing to learn and he was eager and it just worked out so stinking well. So I guess in all of this, the lesson is you can replace yourself by hiring someone in the Philippines who is young and hungry and eager and they're probably going to be loyal and stick with you for 20 years. Maybe they're not going to stick with you for 20 years. Maybe they will. I mean, I have a lot of people. I mean, in like 3 months I have Paulos 20-year anniversary of working for me. Paul, like I said, started in April of 2006, and Paul's working with me again. He took like maybe 8 years off and went somewhere else, but then he came back. Anyway, like, you can have all of these things and you can afford it. The Philippines is really an amazing, amazing place, and the culture allows for this amazing experience. You just have to take the leap, and that leap is hard because, I mean, I first heard about this in October of 2005. And I didn't do it. I didn't pursue it until December of 2005 because I was like, yeah, I just, I mean, it's outsourcing, right? It's a headache. It's a problem. And I had no idea the Philippines would change all of that, that the culture would make that big of a difference. And Jovan showed me all of that. So thank you, Jovan. It's been an amazing ride.
