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Being a “jack of all trades” is exhausting. You do all of the heavy lifting, the administrative work, the uploads, the phone calls, and there never seems like there’s enough time in the day.

The problem isn’t that you can’t do everything; the problem is that you can. Why hire a web designer when you took a $3,000 web design course two years ago? Why hire an accounting firm when you can just buy a program you can learn how to use?

When you do everything yourself, you’re going to hit a ceiling. You can only get so far by running your brand by yourself. Maybe that’s your goal, and maybe you’re okay with keeping things as they are. But if you want to keep growing, you are going to need to outsource.

Outsourcing can look different to different brands: hiring employees or virtual assistants, partnering with a call center, working with a designer to create your next run of t-shirts, or maybe hiring an editor for your videos.

In today’s episode, we’ll be talking about how to determine when to bring on outside help to accomplish your goals and what that can do for the health and longevity of your brand.

Highlights, Takeaways, Quick Wins
  • Whether or not you outsource, there is always going to be some kind of cost.
  • Once you trust someone to do the things you don’t have time to do, they’re going to produce results that might even exceed your expectations for your brand.
  • Outsource when you are confident that your investment in that thing will bring you more gains than if you did it on your own.
  • Outsource the smaller things to get to the bigger goal.
  • Hiring someone that’s not prestigious doesn’t mean that you won’t get a prestigious product.
  • Look for people that are invested in your brand and in what you are trying to accomplish.
  • The person you’re outsourcing to is going to carry on your passion if they’re invested in why you’re doing it.
Show Notes
  • 03:04 Cory: This is an interesting conversation, because the term “outsourcing” can mean different things to different people. There’s a generalized definition of what it means to outsource, and usually, outsourcing looks like working with a call center to handle all of your customer support or hiring a virtual assistant to outsource your day to day things. It looks like this bigger-than-life idea, but to me, outsourcing just means getting out of your immediate bubble. If these are things you can do yourself, that also brings a different edge to it. You have to outsource the things you can’t do.
  • 04:06 When I ran my apparel business, I didn’t have the equipment to do screen printing. I could have saved up and invested in that and bought a screen printing machine, but I would rather outsource that to people who have the equipment and that’s their business. Those are some things I could do myself, but at the immediate moment, I can’t do it. There’s a difference between outsourcing the things you definitely can’t do and outsourcing the things that you can do. Maybe it’s just semantics with the term “outsourcing.”
  • 04:52 Kyle: I think that applies to all of this. Outsourcing things you can do is sometimes a really tough concept, but it comes down to knowing where you need to place your time and effort. You need to know what needs to happen in order for you to achieve more. It gets to a certain point where you’ve added enough things to your workload, where there’s no room for anything else to enter that workload. If it gets to that point, your brand will stagnate. You won’t have growth towards anything, because there are so many things on your plate that you don’t have the time or the attention to focus on it.
  • 05:44 Outsourcing what you can do can actually hold some relief. At first, it’s a little bit nerve-wracking to think that someone else is going to do something that you can do, but once you outsource it, you realize that you’re going to find someone you trust.

Once you trust someone to do the things you don’t have time to do, they’re going to produce results that might even exceed your expectations for your brand.

  • 06:25 Cory: One of the hardest parts of outsourcing the things you can do yourself is that there’s a lot of fear there. Outsourcing comes with the fear that the person you’re hiring isn’t going to do as good of a job as you can do. Ultimately, that requires trust. Any time you hire someone—a company, an employee, a person to do the job you need them to do—it requires a great deal of trust that they’re going to deliver on the thing you hired them for. Let’s say you’re a freelance illustrator, and someone hires you to produce a solution based on their need. They trust you to provide the right solution. There is always going to be a certain level of trust there.

There Is Always a Cost

  • Scarcity Mindset”>07:13 Cory: It’s hard when these are things that I can do. These are things I can do if I manage my time differently or if I give up certain things or whatever. There’s going to be a cost either way. There’s always going to be a cost. We’ve gotten a lot of questions about the monetary aspect of outsourcing. Daniella asked, “How do you figure out what to delegate when there are several things you could choose, but you only have the budget to hire in one area?” Jordan just asked, “How do you determine when it’s worth it to monetarily outsource? Maybe I’m asking this from a place of Scarcity Mindset.”
  • 08:00 Allison asked earlier, “What are some typical signs that it’s time to outsource, and what if who you would like to outsource to is way too expensive for your budget? Is there a time to go with the cheaper option even though it’s not as good, or should you do it on your own until you can afford the thing or person you really want?” No matter what you choose, in regards to outsourcing, hiring, or investment, there will always be a cost. The cost may be financial, time, or convenience levels… No matter what side you fall on, you’re going to be paying with something.
  • 08:48 If you don’t outsource to an editor, let’s say, as a writer, that’s going to cost you time. The question is, what’s more important? What’s going to help you achieve your goals? What is your ability right now? If the editor costs $3,000 and you’ve only got $2,000, then you need to get another $1,000 if you want to hire that editor to accomplish that goal. Or, you’re going to need to manage your time differently, learn how to edit, and do the editing. Then there is always going to be the cost of not doing something else.

Whether or not you outsource, there is always going to be some kind of cost, so you have to decide which cost is worth it.

  • 09:36 If you determine that it’s more worth it to pay someone but you don’t have the money yet, it’s time to get a little bit creative and think about how you’re going to get that money. Is there a different way to acquire the income, the income streams, the finances, the backing, or whatever, to accomplish this other thing? Daniella said earlier, “If I can only focus on one thing, how do I choose what to delegate?” She specified, “I have two things in mind at the moment—merchandise and music videos.” I asked, “Can one advance the other?”
  • 10:22 By focusing right now and outsourcing for merchandise, will that help fund the music videos? She said, “I hadn’t thought of that.” It’s not just ones and zeros. You have to look at it and ask yourself what your goals are, what you’re aiming toward, and what you’re willing to pay in time or money. If you don’t have “enough” of either of those, what is it going to take to acquire more?

Find People Who Share Your Vision

  • 10:58 Kyle: What’s interesting about a lot of these monetary questions is that I think the focus may be on the wrong thing. When you outsource, you don’t just need to find someone who’s capable of doing a certain thing and hire that person. I know that sounds counter-intuitive, but you need somebody who’s on the same page as you, who is as passionate about what you’re trying to achieve as you are. A person’s skill level isn’t the biggest issue here—it’s about how dedicated they are to helping you. That can come with lower costs.
  • 11:47 Maybe, in the future, you hire a bigger firm to do certain things, because the person you hired is not going to scale the way you would like them to. If you’re hiring an employee or someone to outsource for, you need someone who’s passionate about what you are trying to achieve. I have a really good story for this. In the early 1900s, Ernest Shackleton was an explorer and the captain of a ship that went into the Antarctic called the Endurance. This was one of the first voyages into the Antarctic. It was this unknown journey, and he didn’t have any scientific evidence to say that this was going to be a great exploration trip.
  • 13:09 He wasn’t sure what would happen, but he wanted to be the first to go into the Antarctic and say he explored that area. He put an ad in the paper, because he wanted to outsource and get some people to come help him. He didn’t want to go at it alone. What do you think his ad looked like? Most people would say, “I need people to come help me with this voyage into the unknown. I’ll pay really well, because I need people to navigate the ship.” That would be a typical advertisement.
  • 13:58 I believe this was in the New York Times. He wrote, “Men wanted for hazardous journey, small wages, bitter cold, long months of complete darkness, constant danger, safe return doubtful. Honor and recognition in case of success.” It was awesome, because people were inspired. They wanted to do something significant with their lives. They believed in this. What he wrote there is the exact thing he’s putting himself up for, the exact kind of situation he’s going to be in and the exact purpose that he has. The people responding to the ad are people who want to do something courageous in hopes of moving the world forward.
  • 15:02 They know if they complete this thing, they’ll have recognition and success. If they don’t complete this thing, they wouldn’t have fulfilled the purpose they wanted to fulfill anyway. They set out on the voyage, went to the Antarctic, and I don’t know the full details of the story, but their boat got stuck in the ice. Eventually, they made it back. I don’t know how they got out of the ice, but they did it—freezing cold temperatures, this is Antarctica. They returned home safely. Everybody lived, and it was because they all had the same wherewithal to get through that.
  • 15:57 He hired people that were as passionate as he was, and they weren’t going to give up when the ship ran aground or stopped. They were fully invested in making this thing a success. I’ve had this experience in my own business. I have a background in photography, and I could easily take my own profile pictures. It would have been more of a hassle to set up the frame and take the shot, have my wife or somebody push the button on the camera, but I outsourced for that. I outsource for a lot of photos. This person that I’ve hired is 100% invested in what I’m doing. He’s on board. He follows along with my brand. He understands what I’m about.
  • 16:52 He’s always cheering me on, even when we’re not working together. That’s the kind of person I want to outsource to, somebody who is invested in it. His prices, to be fair, are much lower than most places I could go to. He doesn’t have a big portfolio, big brands that he’s worked for, or glamorous credentials, but he’s in it for my brand. He’s in it because he really believes in what I’m doing.

If you want to outsource and you don’t have the funds, find people who are passionate about what you’re passionate about, who can connect with your goalsn even if they’re just starting out.

Outsource Small for Your Bigger Goal

  • 18:01 Cory: When people look at this term “outsourcing,” especially with things you can do yourself or when it comes to hiring, they look to the big things. For instance, Allison mentioned that she wants to hire a producer who’s really expensive. Let’s say the producer costs $15,000 for an album. I don’t know if that’s true, but let’s say you’re Justin Timberlake and it doesn’t matter. You have this dream of working with a certain producer, but you can’t afford that producer at this point. Don’t focus in just on that one thing, but say, “What are some other things that don’t cost as much that will help me get to the place where I can do that?”
  • 19:12 With the case of Ernest Shackleton, he wasn’t saying, “Here’s my big dream. I need this giant boat. I’m going to stay here and hire a captain…” He outsourced, in a sense. He brought on people that didn’t cost as much, that he would pay to a certain degree. The main goal he wanted to achieve required all these smaller pieces. Allison says, “Try more like $25,000 to $30,000.” Okay. That’s not a lot of money. If you want to do that, maybe that’s not the outsourcing you need to be talking about. Maybe you need to outsource some of the small things you’re doing now that can free you up to make the money you need to accomplish the dream.

Outsource when you are confident that your investment in that thing will bring you more gains than if you did it on your own.

  • 20:34 That’s when you need to be outsourcing. Let’s say you’re a musician and you need to put together a demo EP. You can do some of the production at home, and all you’re trying to do is to keep working up the ladder. You need to make a good EP, get it to some studio, they listen to it, they think it’s great, and you move on up. I don’t know if that’s how you do it, but let’s say it is for the sake of this example. If you want to reach that goal, maybe there are things in your life or your work that you can outsource. I’m not even just talking about that thing.
  • 21:22 What if working on your EP means that your house is going to be really dirty, but you can pay some kid in your neighborhood or some friend $20 or $30 to come in once a week and clean your house for you. That’s $120 a month to get you closer to that goal. That’s the stuff I’m talking about, the things you can do to help you get to that goal. It’s the small things. Pay a kid to mow the lawn. Get someone to walk your dogs. Those are the kinds of things I’m talking about, because ultimately, the goal is to get to the $30,000 music producer.
  • 22:09 It’s not just, “I want to outsource to this big thing,” but it’s saying, “What are the smaller things? Do I need an assistant to help me sort through my brain so I can be more productive and efficient? Do I outsource managing my schedule and pay someone $1,000 a month to manage schedule so I can focus on doing the work that’s going to bring me $2,000 or $10,000?” Those are the sorts of things that we’re talking about. It’s not just, “I want to hire this person, do this thing, have this web design, or hire this firm.” These are the things you can do and you are doing.

Ask yourself what it would take to outsource the smaller things to get to the bigger goal.

  • 23:10 Kyle: I’m not as connected with why this goal exists, so I’m only speaking from what I’ve heard from Allison so far. I have to wonder why there’s a specific person that’s the goal to outsource from. I say that because, as I mentioned earlier, there are plenty of people who would get behind what Allison is doing with her music. There are people that would firmly get behind it and push it forward firmly.
  • 23:53 Cory: I don’t know exactly, but it’s a dream producer, like people have a dream job or that kind of thing. “I want to work with the guy who mixed The 20/20 Experience for Justin Timberlake and it costs $50,000 for that whole session.” I think it’s less about needing to do this now for this thing—this is the goal. For instance, one of Kyle’s goals is to own and run a coffee shop. That would be like me saying, “Why don’t you just go on the street corner and pour people coffee?” That’s the idea—it’s the longer form dream.
  • 24:43 Kyle: My goal here is to point out that just because someone has a certain name attached to them doesn’t mean that they’re going to do a better job for your brand. That’s what I’m cautioning here. I’m not asserting that you shouldn’t have a goal to work with somebody, but maybe you find someone who does a better job than that person would do because they’re more invested in what you’re doing and they’re not just taking you on as a client because you’re the 500th person that year that has approached them.
  • 25:28 Cory: Ultimately, it comes back to the question, “What is the goal? What’s the drive?” Why am I doing these things? What do I need to do to accomplish them? What’s my next step to get there? There may be intermediate steps of hiring someone for the time being to get closer to the long term goal or outsourcing in a certain way to get there when it’s not exactly what you’re looking for. Maybe you can’t hire a full on type design company to produce a custom typeface for your brand, but you can hire someone out of a local school to produce that for less money. Sometimes, it’s easier to find people who are cheaper and who are invested. Just because someone’s invested doesn’t mean the result of their work will be beneficial to your brand, but it’s still something to consider.
  • 26:51 Budget, money, and what’s in your account matters. If you don’t have $100,000 to invest in something, you can’t invest in something that’s $100,000. You have to sort out what those things are. Start with the smaller things and work your way out to free up your time so that you can make the money to accomplish the goal. I agree with Kyle, though—you have to have people who are on board with your mission, especially for the things that matter so much to you.

The Value of Commitment to Your Brand

  • 27:40 Kyle: Allison in the chat just said, “Sometimes, I find that the smaller people don’t have the resources, connections, and professional habits that the bigger people do.” None of those things matter. I realize that’s a bold statement. They matter if you’re approaching someone to say, “Hey, can you edit this thing for me,” but if you have a purpose and a reason to do these things, the person you’re hiring will come under your process and will follow along with the professional habits that you have, because they want to work for you and with you.
  • 28:30 Cory: I have a question for you, Kyle. This is a slight challenge, because I’m interested in what you’re saying. I’m not sure that I 100% agree with it or disagree with it, but I want to challenge it. Recently, you hired a screen printing company to produce the prints you made for your store. You had a couple of prints made, your Galaxy icon print and the Keep Moving Forward print. You hired out to do that. You used a company called Mama’s Sauce, a premium company that does a fantastic screen printing job.
  • 29:44 You hired them for various reasons, one of which was word of mouth. I don’t think you had used them before, but they do a really great job, and they had done a lot of work for people that you know, so you hired them. The product itself is fantastic. You’re able to sell that for a premium price because the product is fantastic. Let’s say you found a local company that wasn’t as professional, didn’t have as good of a process, and could produce the product but not quite get it there, but they really, really believed in what you were doing. They were all about icon design. They were all about your dream and your vision.
  • 30:37 When they produced the product, though, there was some overlapping on the colors and you had to do two revisions because they didn’t know how to do CMYK. However, they really believed in the vision and were really in tune with you. That’s the same thing.

It’s important to want quality for the things you’re producing and to hire the people who have the resources, connections, and professional habits to produce the thing you’re trying to produce.

  • 31:11 Now, if you find two companies that produce the same kind of product and one is cheaper and one’s more expensive, but they both believe in the dream and they agree with you on the vision, there’s something to be said there. I think I get what Allison is saying. My question is, does it matter if someone believes in your vision and is on board with your process if the end result isn’t as good as it could have been if you hired someone else?
  • 31:43 Kyle: There’s an evaluation of their work, of course. That’s going to happen with anybody. Even Ernest Shackleton, who we talked about earlier, I’m sure when people came to his door saying they wanted to work for him, he evaluated them to make sure they could make it both physically and mentally. I’m sure he sat down and talked with them, that he made sure they were really interested in this thing and could really make it happen. You need to have a little bit of evaluation. I agree with that. I’ll go back to the person I hired to do photography. There are some things they don’t have together that I wish they had together from a process standpoint, like taking me through a contract. There were some things that weren’t ideal to me.
  • 32:43 Because they were so dedicated to what they were doing, they made absolutely sure that I got the right thing. In Cory’s example, the screen printing Mom and Pop shop that throws something together and it’s not as good of a product, if they were really invested in what I wanted to achieve, they would work relentlessly to make sure that the final product is exactly what I’m looking for. They’re in it for what I’m trying to achieve. They’re not in it to make sure that I get a quality product. They’re in it to make sure that I achieve my goals and that my brand accomplishes its purpose.
  • 33:34 I went with Mama’s Sauce because they were recommended a lot and I wanted to try them out. I wasn’t sure how the process would go. I was interested, and it was one of the few places I knew to go for this particular thing. They were very nice. Their customer service was great. Talking with them was awesome, and they got behind what I’m doing. Yes, I approached them because they’re bigger, but I could afford to do that. I didn’t hire them because I can’t afford to do it and I’m losing money on my products. I can afford to hire them, so I tried them out first. That doesn’t necessarily mean that I will stick with them or that I would have hired them if I didn’t have enough money.
  • 34:27 I’ll give another example. There’s a really well known designer named Aaron Draplin. He was at a conference I was at. He was a speaker, and I was presenting a workshop. He started talking about the three printers he uses, and they were there at the conference. He brought them into the conference to screen print his shirts live for people when they come up to the booth. This screen printing company is out of Austin, Texas, and I don’t even remember the name anymore off the top of my head. It’s a very obscure company.
  • 35:09 He uses them, and during the talk he gave, he said, “I use them because they are behind what I’m doing. They’re not some big company that everybody wants to go to, but they believe in what I’m about and what I’m trying to accomplish.” He’s spending less on prints, but he’s getting a better product because these people are invested in what he’s doing. I’m not suggesting that you never hire someone that costs a lot.

Don’t only hire someone who costs a lot because you think you’re going to get a better product or achieve some kind of success, because that isn’t necessarily true.

  • 35:57 That person’s going to get your project, take your money, edit your content, produce your music, and ship it back to you and say thanks. This other person that is fully invested in what you’re doing may not be as big, have as big of an audience or as big of a budget, but they’re going to focus on that and work on that. They know it’s for you and the reason you want to make this music, so they might make it better than the producer that just took it through their process and sent it back to you for far more money. It’s that social proof thing, where we think people with big credentials will do a better job because of their credentials, but that’s not always the case.

Outsource to People Who Connect With Your Goals & Help You Achieve Them

  • 36:55 Cory: Ultimately, it depends on the final product. It depends on what you’re getting at the end of the day. If you’re getting something that meets your goals and helps to advance you to the place you want to be, then that’s who you want to outsource to. Is this advancing you? Everything that Kyle’s saying boils down to this: is making the decision to outsource, to invest, advancing me toward my goals? That’s my takeaway here. It’s more important here to consider whether the end product is going to get you closer to your goals.
  • 37:51 If not, if it’s a more well-known company and they’re not going to get you closer to your goals, don’t go with them. If it’s a lesser-known company and they’re not going to get you closer to your goals, don’t go with them. You have to evaluate what the end result of that relationship is going to be. Outsourcing, hiring, bringing people on, or getting a company on board all requires you to assess whether the investment is going to be worth it or not, if it’s bringing your brand closer to where you want to be. Is that a fair assessment?
  • 38:35 Kyle: It is. Please don’t misunderstand what I’m saying. I’m not suggesting that you don’t have a goal to work with a certain person or that somebody that’s in a high position in a certain area you’re involved in isn’t rightfully in that place. That’s not what I’m asserting here. I’m trying to say, don’t be blinded by those things. Don’t be blinded by the fact that somebody seems to have it all together or has a big company. There are people who are going to have a big company in five to ten years that are in complete obscurity at this point, that you’ve never heard of.
  • 39:19 That’s how all of this works. People listening to our podcast that are just starting a brand are in complete obscurity right now, but in five to ten years, maybe we will have heard of them. Maybe lots of people will have heard of them. Maybe they’ll be at the top of their industry, for all you know. The people that are there now have worked to get to that point.

When you hire someone that’s not prestigious, it doesn’t mean that you won’t get a prestigious product.

  • 39:52 My point is, when you outsource, look for people that are invested into what you are trying to accomplish and want to help you move forward with your goals. No matter what level your brand is at, that’s super important. Regardless of their prestige, they need to be on board with what you’re doing and want to achieve goals for you because they care about what you’re doing.
  • 40:19 Cory: I agree, but the end product has to advance the goals. It’s not just that someone wants to help you advance your goals, but the product has to actually do it.
  • 40:35 Kyle: The person should connect with your goals. That’s how I should have worded it. Let’s look at our situation, Cory. We work for seanwes, currently. We both have our own brands that we’re working on—I’m working on my brand and Cory is working on his—but working for seanwes is our day job. It’s more than that, because seanwes is a brand with a mission that we believe in. I’m being transparent here. I’m not making as much as I probably could somewhere else working the same amount of hours, but I love what seanwes is about. I want to work for this company.
  • 41:39 It doesn’t matter that I make six figures a year if I’m miserable at my job. What matters is that I’m passionate about what this brand stands for and what we’re doing. I’m producing the best I possibly can. I’m approaching every project for seanwes like I would my own projects that I care about deeply because I care about the brand moving forward. Sean McCabe, owner of seanwes, could have hired some random illustrator. He could have hired the best illustrator in the business, and maybe they produce good work, but they don’t have that passion and drive for this brand.
  • 42:26 That’s not to say that I’m the only option, there’s no one else out there, or whatever. I’m not necessarily someone of prestige. There are plenty of people that I know he’s connected with, that I know he knows, that are far more prestigious in the design and illustration communities that he could have approached to hire. That wasn’t the option he went for, because he wanted someone invested in making sure the brand is taken care of, and that whoever is in this position needs to have close to the same passion and effort for this thing that he does.
  • 43:36 If you want to hire someone that’s really well known because you know they’ll do the best for your brand, that’s absolutely fine, but don’t assume that prestige equals quality outsourcing. You can get a local shop, people that may not be charging as much as they should because they’re growing their brand, they’re not known yet, they’re in obscurity, but they’re going to do a very good job for your brand.

Don’t assume that you’re stuck because you can’t hire someone who’s way out of your investment range right now.

Find someone who’s invested in making sure you succeed.

  • 44:19 Cory: And who can deliver and help push you closer to your goals. When it comes to sorting out how to outsource, you have to figure out what the dream, goal, target, path, and direction are that you want. What things are you doing that can be done by other people, even if it’s on a smaller scale? If it’s on a big scale, figure out if there are alternatives to doing things the way you want to do them—if, by using those alternatives, you can get closer to your goal faster. Part of outsourcing is sorting out what those things are and being honest with yourself, because you may need to outsource things that you really enjoy doing.
  • 45:33 This is something that our boss Sean at seanwes talks about a lot. Part of Kyle’s job is working on featured images for the shows and part of my job is interacting with members and customers and sorting out the website. Some of those things are things that Sean really enjoys doing. He enjoys design. He enjoys interacting with people. Having us on board allows him to continue pushing forward the vision and progress of his brand. We have a video guy, Cory McCabe. Sean can shoot and edit video He knows how to do that, but he outsourced that. He can pay someone else to do things he knows how to do so that he can accomplish his goals better and faster.

You Need to Know Your “Why”

  • 46:36 Kyle: It’s a tough thing to evaluate, because there are things you love doing that you should probably outsource, or things you’ve done for so long that they feel like things you have to do and that nobody else can understand that process. I haven’t done a lot of outsourcing. I’ve done the photo outsourcing, which far exceeded my expectations. For a lot of people I know who have been figuring out what to outsource because they’re at the point where they need to do it, the biggest thing is having trust. You have to trust the person, and you have to realize that the people you’re hiring for these things should be focused on that thing.
  • 47:37 For example, photography. I’m not focused on photography. I do design work all day and illustration work for seanwes, and I do photography occasionally, but not as often as this person that I hired. They did a better job than I would have done because they’re dedicated to that. That’s what they do for a living. It’s tough to realize that someone could do something you can do better than you, but it’s possible.

The person you’re outsourcing to is going to carry on your passion and your approach to what you’re doing if they’re really invested in why you’re doing it.