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I waited too long to hire with my first business.

I was scared to hire because I didn’t have the work. I was scared to get more work because I didn’t have extra help. It was a chicken-and-the-egg problem.

Now, I have local and remote employees. It took a lot to overcome my superhero syndrome.

Matt seems to have never had trouble hiring help. He makes it look effortless. It’s definitely a skill.

In this episode, I grill him with a ton of questions because he not only has many employees in numerous businesses, but also works with remote Virtual Assistants on the other side of the world.

I ask him about his hiring process, training, creating culture with remote employees, the legalities of contractor vs. employee, and when is the right time to hire. Matt also shares some of his resources with us.

It’s a great listen if you’re hiring right now, but also (and maybe even more importantly) if you’ve yet to begin hiring. This episode will give you a good idea of what you should be looking for and what to expect when hiring a Virtual Assistant or remote employee.

Highlights, Takeaways, Quick Wins:
  • The more time you put into training your virtual assistant or employees, the more they can put into your business.
  • Don’t wait until you’re overwhelmed to hire or you’ll hit a ceiling and limit your business.
  • Hire proactively.
  • Don’t get caught up in wages and budgets—think about how a virtual assistant can bring in more money for you and boost your business.
  • The first person you hire should be your “right-hand man.”
  • Don’t think of salaries as an expense, think of them as an investment.
  • Always have an open ear to hearing and helping with problems. Don’t just jump to telling them to “figure it out” all the time.
  • Tell your employees they’re doing a good job (it really is a big deal).
  • If your remote employees don’t feel comfortable contacting you for help, they’re not going to last.
Show Notes
  • 08:47 Sean: Matt’s a guy that focuses on bringing people on, sharing his knowledge, and expanding businesses. Matt, there’s a lot of little details that need to be taken care of and I imagine you’re not spending your entire day doing all those little things other people can help with. You have at least a few virtual assistants right?
  • 09:13 Matt: I have one main one, Vicky, and three others under her that do general administrative stuff. When I’m not available, Vicky is there to keep track of everything and she pretty much knows what I do. I’ve sat down with her and gone over what I’ve done in past situations.
  • 10:17 Sean: Is she local?
  • 10:18 Matt: No, she’s in Australia.
  • 10:20 Sean: She’s able to handle things from there, even when you’re unavailable? How do you get someone to that level?
  • 10:31 Matt: She’s been with me for three years now, so it’s different than with someone who’s new. She’s seen me go through all my businesses, so she knows the ups and downs. I had to pay a lot in taxes this year, which has limited resources for a lot of my businesses and she keeps track of all those restrictions on finances. She’s learning and evolving with me, to the point where she’s even opening up her own businesses! I’m always willing to teach my employees and partners my knowledge, and if they feel like they’re hitting a ceiling with me, then I’m cool with them doing their own thing. In the next year or so it looks like she’ll be leaving me and we’re trying to find a replacement.
  • 12:11 Sean: How do you get someone to her level and what’s the process?
  • 12:14 Matt: It’s going to take years. When I first brought her on, we did a ton of training. I did screen casts of the tasks I knew she was going to be handling. You should definitely put in the time to do that kind of training to help your virtual assistant, because:

The more time you put into training your virtual assistant, the more they can put into your business.

  • 12:56 Sean: I learned that screen casting is what I needed to do. Instead of screen sharing and showing someone once, you record it so they can go back through it, but also if you need someone to replace them or you expand, you have the training recorded.
  • 13:12 Matt: When I started doing real estate, originally, I was doing the research to find houses from 9pm to 2am. Now, I have her doing the research for it. I sat down and recorded a research session for her once and she’s able to go back and see what I was researching. Something else that’s been helpful for her is being available when things are going on. I used to have a virtual assistant from India that was a graphic designer and did content creation for me—flyers, price sheets, etc. It worked out because he would work while I was sleeping, but when I tried to have him do some of what Vicky is doing on a daily basis, it was harder because their culture is a little different than here in the US. He would blow off things I wouldn’t blow off and he wasn’t very good with clients. It also wasn’t good that he wasn’t available during the day here.
  • 15:32 When Vicky and my other assistant in Barcelona first started, I would work with them in the evenings or stay up at night. I would screen cast with both of them and we all evolved as a team. This was at night so it was a little bit difficult to get them to where I needed them but it was good enough. I had them contacting people, writing emails, and researching.
  • 17:00 Sean: Is it still a night time thing?
  • 17:03 Matt: I require them to be available during the day, which is night for them. I also have an assistant from the Philippines.
  • 17:44 Sean: Some people are wondering where they would go if they wanted to find a virtual assistant.
  • 17:49 Matt: It depends on the person, the industry, and who you want to work with. There’s certain people for certain things. Indian people are good at doing website and SEO stuff for cheap. They’re good at hashing out things quick but the quality isn’t the best. The Philippines provides medium quality and their prices are a little higher than India. Australia, El Salvador, and some places in Europe are even more expensive but the quality is higher. Then you’ve got the US with higher quality but almost as expensive as having an in-house employee.
  • 19:01 Sean: Is price the primary reason, at least for you, for going with a virtual assistant from another country?
  • 19:09 Matt: Yes and no. It depends on the business. If it’s a new startup business that needs basic stuff—data entry, research, sending prewritten emails—I wouldn’t mind going with India or the Philippines, but if it needs to be more personable with a client, then I want to stay more with Europe, Australia, El Salvador, or closer to the US in culture. They know the culture and communicate a lot better. That’s not to say the other countries aren’t, I’ve just had a better experience with them.

What to Look for in a Virtual Assistant

  • 19:56 Sean: Say you’ve narrowed down where you want to look for a virtual assistant. Now, you’re going through candidates, what kinds of qualities or characteristics are you looking for upfront? Then, once you decide to bring someone on, what kind of things are you vetting to decide if they’re going to be a good fit in the long-run?
  • 20:24 Matt: I’ll take Vicky as an example. When I was first looking for someone to do general administrative tasks, she was more of a content creator/marketer, which I didn’t need at the moment but would need soon. My main question for her and two other girls I interviewed was, “Why would it be a mistake to not hire you?” They all pretty much said they would go the extra mile for me but I liked Vicky’s answer, “I’ll go until my fingers are numb.”
  • 21:24 Sean: You were looking for someone who was going to work hard.
  • 21:28 Matt: I needed them to be ok with me being a slave-driver. At first we had a group interview so I could tell them what I was looking for, the job description, and what we would be expanding to in the next six months to a year. I had their resumes so I knew what they had previously done, and I asked them if they were ok with doing things outside of their comfort-zone that they hadn’t done before. I asked them if they would be willing to train on things they weren’t familiar with. They all said yes, but it came down to doing a week trial run with all of them. I went through everything with them as if I was hiring them to do the tasks I needed them to do—estimates and communications with my clients or partners.
  • 22:50 At the end of the week, I was able to see how much they were doing with a program that takes screen shots every few minutes of them working. I had set up a dummy email account they could send things to as if it were a client and I was able to see how they interacted with these “clients”. Vicky impressed me because she really went above and beyond. I was looking for someone that would do the tasks I gave them, but that also self-initiate some projects around those tasks. I paid her for 40 hours but I got 60 hours out of her. I hired her and started giving her bonuses or incentives to keep working that hard. I started with $50 bonuses and worked up to $150 bonuses or weeks off for vacation.
  • 25:05 Sean: You bring them in but you don’t treat them special at first. You want to see if they have the initiative.
  • 25:09 Matt: I would actually pay them pretty low in the beginning. When I first brought Vicky on, I was paying her $5 an hour.
  • 25:19 Sean: Is that pretty average for remote virtual assistants?
  • 25:23 Matt: That’s pretty standard in the Philippines and India, but outside of that, it goes up to about $10. Even from some agencies in the Philippines they’ll cost $10 an hour because they work US hours.
  • 25:46 Sean: The reason it’s so cheap is because there’s such a cost-of-living difference?
  • 25:51 Matt: Yeah. I was paying a girl in the Philippines $350 a month and I felt like I was robbing her, but she said that it was more than enough. She didn’t want more than $400 because the government starts looking into how rich they’re getting. It’s a ton of money in their currency. I eventually started sending them more because I didn’t feel right doing that.

When to Hire

  • 26:33 Sean: We’ve got a question that I think is relevant here, “How do you strike a balance between finding someone of quality and managing your expenses? Do you look at this person as an investment or as a business expense?”
  • 26:50 Matt: They’re definitely an investment. You spend $1,000 a month on a virtual assistant and you make $3,000. My virtual assistants don’t work on the business end to triple my money like that, but they’re helping me free up my time and allowing me to work on my businesses to make more money. As a solo-entrepreneur, you have to do so many things. Social media is just one thing we don’t have time for and I’ll be bringing on virtual assistants to do that in the future.
  • 27:51 Sean: This is my own question, I’m curious what your advice would be to someone who is relatively new in starting their business. At what point would you say they should start considering hiring? A follow up to that is, do you think it should be a virtual assistant first, or should they hire an employee first? How would you approach it?
  • 28:19 Matt: It totally depends on what they would have the virtual assistant do. I’ve learned that we have our strong points and our weaknesses, and a virtual assistant might be great at blogging, content creation, or marketing. There’s so much administrative and research stuff to do that it will keep them more than busy, even if you start them part time. If you’re a start up, you might be able to pay $5 an hour, but not $10 to $15 an hour. It’s an investment for the business but the business has to actually make that money to pay them. In the beginning, it’s probably best you put more time into your business, products, or services so the business can more money. Once you get that built up, get a virtual assistant to help with the administrative stuff. It’s not going to cost you a ton and will free you up to make more money for the business. You can start them out as part time, work up to full-time, or if you’re ready, you could get an in-house employee past that.
  • 30:35 Sean: That’s a good answer for people who are just starting out and wanting to know when they should hire. What about the person who has a business, what would you say are some signs that it’s time to hire a virtual assistant?
  • 30:59 Matt: My email blows up all day and that’s something my virtual assistant takes care of and let’s me know when I need to handle something. I also do a ton of research—I want 10% of my money to go to research and that’s something the virtual assistant can do.
  • 32:06 Sean: If you’re overwhelmed with something, that’s probably a sign it’s time to hire.

Don’t wait until you’re overwhelmed to hire or you’ll hit a ceiling and limit your business.

  • 32:09 Matt: If you’re limiting the business, then you’re limiting the money coming in. It’s not all about money, it’s more about your time. You can’t get your time back. Even if the budget is tight, do it. Start with part time or assistants from the Philippines, India, or even Europe.
  • 32:40 Sean: The point where you know you waited too long is being overwhelmed. That’s a sign you should have gotten help before this point. If you’re overwhelmed, that’s probably a good sign. Something is going right to the point where you’ve got a lot of work to do. I’m hearing you say you want to hire proactively. A lot of people are afraid because they’re making money and they want to keep that money. If you get to the point where you’re overwhelmed, then your business can stagnate or decline. Your clients or customers could have a bad experience because you’re busy with other things and it all goes downhill from there.
  • 33:40 Matt: You’re always going to be overwhelmed as a business owner because that’s the way it is. We’re getting a virtual assistant to help with inventory ordering and equipment failures for the snow cone business.
  • 35:45 Sean: Here’s a relevant question from Brent, “What type of tasks do you present the virtual assistant with? Do you define a specific role for them, or do you give them whatever comes up?” I’m thinking the first person you hire should be your right-hand man. In the beginning, you’re not big enough for them to just do email, so you need them to help you with a bunch of things. It seems like the first person is the most important and then when you get more people, you can define more specific roles.
  • 36:23 Matt: When you you look into agencies, they ask for a specific task you need, so they can find someone to fill it. You need help with a lot of stuff! You should definitely have that right-hand man or woman so when something comes up, they’ll take care of it.
  • 37:02 Sean: Maybe you need to communicate to this person that this role is what you want them to fulfill but you’ll need to get traction in the beginning and have them help with other things. Laci, my wife, handles administrative tasks, customer support, and product fulfillment. Administrative work is her specialty and the primary role she’ll be taking on, but in the meantime, we need shownotes written for the various shows on the network. She’s been helping with that even though that’s not really her thing. She doesn’t exactly want to be doing them but eventually, we’ll get someone to write shownotes or do our accounting.
  • 38:03 My newest hire was Cory Miler, our Product Director. He’ll be making new products, working with manufacturers, and doiong email marketing. Right now we’re in a transition period—the Community is reopening and we’re working on courses to try to get case flow going. I don’t want to be sinking a bunch of money into physical products for a few months, so we’re having him focus on helping us write marketing material that will get cash flow going. He’s the Product Director, but he’s mostly helping me with marketing right now. We’re working towards what he’s specialized in.

Don’t think of your virtual assistants’ or employees’ salaries as an expense, think of them as an investment.

  • 38:57 Matt: People get so caught up in wages and budgets, but you need to be thinking how that virtual assistant can bring in more money for you and boost your business. You’re not taking advantage of them—as you grow, they grow. Tell them that! Tell them, “Help the company and the company will take care of you if you want to be part of it long-term.” When you’re hiring, the most important thing to communicate to them is that you’re looking for a long-term employee. I tell them, “If you can provide the value for whatever I need help with, my business will take care of you.” I treat my business how I want to be treated and my business takes care of me.

Employee vs. Contractor

  • 40:43 Sean: We’ve got a legal question here, “When it comes to hiring a virtual assistant, are they your employee, or working as a freelancer/contractor? And what are the legalities behind that?”
  • 40:54 Matt: The majority of the time, they’re employees. Vicky is a subcontractor under me because she has her own little business managing virtual assistants. I let her know tasks that I need done and she does them if they’re her line of work, or she has other assistants do them if there’s no training needed. If you go through an agency, there’s a way you can set up virtual assistants as contractors. If you’re telling them to do tasks, but you’re not telling them how to do those tasks, they’re considered contractors.
  • 43:40 Sean: Brookes says that his thoughts when looking up the benefits of hiring a virtual assistant are to hire his wife. I told him if that’s an option, definitely start there if she wants to. With a remote worker you have to train them, communicate with them, deal with the time difference, and you skip all of that when you hire someone like your wife.
  • 44:17 Matt: My wife does work for me. I told her, “Instead of me having to pay another virtual assistant, I can pay you and that’s money that’s staying within the family.” I also feel like I can trust her more because she’s my wife. I’ve heard horror stories about people who gave their virtual assistants personal information and had all their money cleaned out. I’ve always had that fear so I take precautions to prevent that.
  • 47:02 Sean: Ben asks, “Do you pay your virtual assistant for training or meeting time?”
  • 47:06 Matt: Definitely. Sometimes, if you go through an agency, you don’t have to pay them for training because it’s considered a trial, but I always pay them anyway. I’m taking up their time and I wouldn’t want someone to take up my time without paying me. Taking care of your employees, and even your virtual assistants, is important.
  • 50:16 Sean: Taking care of them means going even far beyond it, but definitely including paying for training.

Creating Culture With Remote Employees

  • 50:37 This question is important for me because I don’t have virtual assistants, but I do have remote employees. Terrance asks, “What are some ways to create a good culture with a remote employee?” This is all still really new for me. Fortunately, everyone on the seanwes team was able to get together at the conference we all went to last month. It was so cool to have everyone on the team all in one place and to get to hang out for a few days. It was huge to be able to see people in person and have fun. We’re also talking about having a seanwes conference exclusively for the Community members and I think that would be a really important thing for the culture here. Even besides that, I’m thinking up ideas for different retreats just for the team.
  • 52:25 Besides that, I try to have regular conversations with them on the phone, even though we converse over text, email, and chat all the time. I try to have calls once a week to touch base, but I would like to have a team group chat once a month to remind them that we’re a team even though we’re all working in different states.
  • 53:13 Matt: Every Monday morning we like to do a Google hangout together to run through how the week should go. They also chat all day with Slack and I can see what they’re talking about. At the end of the week we also do a 30 minute run through to check in with everyone and make sure nobody had any problems.
  • 55:51 Sean: Can you distill down two or three tips for creating a good culture with remote employees?
  • 56:06 Matt: Communication is one of the biggest things—making sure they’re all communicating with each other. I try to get them to help each other out on projects that they’re familiar with. That way they’re piggybacking off each other’s knowledge base and constantly communicating. Also, how you treat them is important. I encourage them and point out their successes to others on the team.
  • 57:43 Sean: I like that tip because some people are words of encouragement people. Some people might just want the money and for others, it’s not all about the money past paying their bills. They just want someone to say, “Hey, you did a good job. I appreciate your work.” From our perspective it seems simple. “They should know they’re doing a good job because I’m not yelling at them!” That’s not how it works though, you need to tell them they’re doing a good job.
  • 58:20 Matt: I’ll even ask them about their workload and if they feel overwhelmed when I see them contacting me a lot. I ask them how they feel to make sure they feel comfortable and to know if they need more training. I know with business it’s crazy busy but always have an open ear to them. I don’t want to be that guy that shuts them out and says, “Do these things and if you don’t know how, figure it out!” That’s just going to get them all stressed out. You want them to take initiative, and they will eventually, but make them feel comfortable, encourage them, and motivate them. Get them to the point where they’re not texting you all the time and they can figure it out themselves. Even if they can’t figure it out, but they feel like they can contact you to tell you that they tried to figure it out, that’s good.

If your remote employees don’t feel comfortable contacting you for help, they’re not going to last.


  • 1:00:28 When I was first looking for virtual assistants, I used They check out all the virtual assistant agencies and have feedback videos from their experiences with them. This isn’t a place to find a virtual assistant, it’s just reviewing different agencies, but it’s a helpful resource.
  • 1:01:06 Sean: People are still asking, “Where do I go to find a virtual assistant?”
  • 1:01:12 Matt: I found my virtual assistant from the Philippines from and Vicky from Elance or oDesk. The advantage of using an agency is they assign you an account manager and the virtual assistant is under them, so if the virtual assistant isn’t a good fit, you can get another one.