SEP Episode 32: Apprenticeships What Are They? – Who Should Hire One? Who Should Be One?

On today’s episode I wanted to talk about a question that I commonly get from a lot of readers and listeners and people I work with. The question is, how did I get my start in online marketing and entrepreneurship and business? I got my start in an apprenticeship. Apprenticeships are one of the oldest and most effective forms of education and skill transmission. On today’s episode, I’m going to give you everything you need to know about becoming an apprentice or hiring an apprentice.





Key Takeaways

[1:31] What is an apprenticeship

[2:46] How I started and what I learned during my apprenticeship

[6:10] How my apprenticeship led me to be a successful entrepreneur

[8:14] How to effectively hire an apprentice

[12:14] How to become an apprentice

[17:25] Where to find and how to apply for an apprenticeship

[24:51] An alternative way to find an apprenticeship opportunity

[26:03] How to be a successful apprentice


Links and Resources Mentioned in this Episode

Growth Ninja

The Empire Flippers



Kyle Gray:

Hello and welcome to the Story Engine Podcast. My name is Kyle Gray. And today I wanted to talk about a question that I commonly get from a lot of readers and listeners and people I work with. The question is, how did I get my start in online marketing and entrepreneurship and business? And, I think a lot of people ask this because they’re either curious, they want to get started themselves. Or maybe they’re a little bit further along and just hearing some of my background and my stories, wondering what got me into the field I’m in, in the first place? A lot of people think that I went to school for business or studied marketing or anything like that.

That’s really not the case. I got my start in an apprenticeship. Now, you’ve probably heard that word before but maybe haven’t thought of it in a context of running a business or where an apprentice would fit in.

Apprenticeships are one of the oldest and most effective forms of education and skill transmission. A classic example would be a blacksmith in the Middle Ages who brings on an apprentice to start helping with some of the basic and tedious tasks. But the apprentice slowly watches and learns from the blacksmith, learns their craft, and starts to develop their own skills, slowly becoming more and more valuable, more and more important. And over the course of years, building out their own skill set and eventually becoming their own journeyman blacksmith or master blacksmith and carrying on the traditions that they learned from the original blacksmith.

So, in this episode today, I want to explore all about apprenticeships, who should get apprenticeships, how to apply for and position yourself to get an apprenticeship with somebody that can really boost you forward. And, if you already have a business, you’re already an established entrepreneur, how do you start your own apprenticeship, bring on an apprentice, and why that would be good for you.

Let’s start with my own apprenticeship story. That story starts a couple of years back when I had just finished my Master’s degree. I had $6 thousand in the bank and I was getting ready to fly over to southeast Asia and start a business online, working from the internet, living in Chiang Mai, Thailand. Looking back, this was probably a very crazy plan. I didn’t have a lot of business experience, wasn’t sure what I was going to do at the time. But I am very grateful that two days before I ended up getting on the plane, traveling over to Asia and starting this adventure, I was hired by Dan Norris and WP Curve to help them with their content marketing and their storytelling.

Dan was a prolific content marketer creating a lot of great, well-written articles on a nearly daily basis. But his startup was growing faster and faster and he was spread too thin for time to keep up on maintaining this great content. So he brought me on to help me out. And I’m so grateful for this because if I just would have gone out to southeast Asia on my own and tried to figure it out myself, I don’t know where that could have taken me. Instead, I got to study under a master of the craft of content marketing and actually learn how to function within a system that had already been built, that had already been put together.

Now, the first few months were incredibly difficult. Apprenticeship, as opposed to internships, usually require a lot more of an entrepreneurial spirit. An apprentice, like an entrepreneur, needs to be very creative and systematic in solving problems. Meaning, they need to solve problems and troubleshoot them completely on their own and then come up with processes and systems that can help them repeatedly solve this problem in the future so they’re not repeating all of the same work.

Thinking like this and being able to operate in a totally new business was a challenge for me. And it was compounded by the fact that I was living in a new city in southeast Asia that I was getting used to, the lifestyle and where to work and putting all of that together. And I didn’t have much experience with remote work and remote communication at the time, which was an entirely different skill set I had to build up.

You may be wondering why I was in southeast Asia at all at the time. I had been hearing from a lot of different entrepreneurs, especially those who are interested in traveling the world and growing their business from their laptops, that Chiang Mai, Thailand was a great place to bootstrap a business, develop your skills, and get started. You can live a high quality of life for not very much money. And fortunately, though it was one of the best experiences of my life, it definitely wasn’t easy.

If you’ve read the Story Engine, the first chapter, which you’re familiar with, is all about those first few months at WP Curve and trying to, at first, do everything on my own, solve all the problems myself, and just be more of an employee. But, as time went on, starting to use systems thinking to get more leverage on the problems I needed to solve, the tasks I needed to do, and the job I needed to get done is when stuff really started to move forward.

I stayed with WP Curve for a little over a year. And through that time, I was able to create dozens and dozens of articles that positioned me as an authority in the areas of startups, entrepreneurship, marketing, and remote team management. And I was able to make a lot of really good connections with high profile startup founders, entrepreneurs, coaches, and really powerful people that enabled me, once I left WP Curve, to get a lot more traction on my business and start moving forward in ways that I probably could not have done on my own.

So, working with WP Curve was a huge jumpstart for my skill set, for my network, and for my confidence and knowledge of how a good business is run.

Now this arrangement wasn’t just extremely valuable for me, but it was extremely valuable for Dan Norris and all of WP Curve. With the extra time that Dan was saving not having to maintain the WP Curve blog and do all of the tasks that were required to achieve the goals in content marketing and storytelling we wanted to achieve, he was able to continue refining his craft, but create more of a personal brand and create several more books. When I started working with him, he had just barely launched his first book, The Seven Day Startup, which was wildly successful, and positioned him as a big authority in the space. He continued to write more books, build out a personal brand, and launch a successful membership site with that extra time and confidence knowing that his business, WP Curve, was in good hands, or the marketing portion, at least, with me. He was able to continue to grow his own brand and expand himself.

So, a great deal all around; right? And maybe, as an entrepreneur, you’re sitting and listening, thinking, I could sure use an apprentice to help me with all of those things as well.

Let’s talk a little bit about who should get an apprentice. What does your business look like when you could most benefit from an apprentice and what does the entrepreneur look like that could hire an apprentice and be successful with one?

First of all, I think you need to have a proven process and a growing business. You need to understand your market and be able to be profiting and growing from your market. You can’t expect new blood to come into your business and just instantly be able to figure everything out at a very low price and solve all your problems for you. It’s best, once you have a system that’s proven, working, and predictable, to take one or two of the components that have already been well mapped out and well figured out, and then hand those off to somebody else. That way, they have something established, there’s precedence that they can start to understand the culture and the processes of your business, and learn how to function within those rather than solving problems on their own and blazing a new trail for you. Especially in the beginning stages of apprenticeship.

On top of that, I think that you should have a very specific skill or skill set that you want the apprentice to focus on or develop. It is very important that you have some skills to teach in this skill set. You don’t want somebody to come in and learn a totally new skill set that you haven’t explored or applied to your business before. They won’t be able to fit in as well or be successful. But if you are very skilled at something like SEO, social media, marketing. Lots of marketing jobs and tasks are very good for this. There’s always young blood who are interested in developing or improving their marketing skills and growing with somebody who is well established and an authority in that area.

So, make sure that you have a good skill that you can teach your apprentice that will leave them more valuable, more competitive, and a more viable entrepreneur once they’re finished.

Another key element of this is being process driven. You need to have realistic expectations when hiring an apprentice. We want to understand what’s being exchanged in an apprenticeship. The apprentice is offering their energy and their time in exchange for learning skill development and network development. And you, the apprenticeseur, I’m not really sure what that word is. But anyway, the creator of the apprenticeship, the owner of the apprenticeship, the trainer of the apprentice, you are offering your skills, your knowledge, and a peek into a successful business and how that’s working in exchange for their time and energy and their problem-solving abilities.

One of the inherent truths about a successful apprenticeship is that they’re going to learn the skills, they’re going to learn the systems, and once they’re sufficiently educated, they’re probably going to move on from your business. They may not stay with you for an incredibly long time. Which is why it’s important to bring in the entrepreneurial mindset as an apprentice to help make sure that they are creating processes, so that everything they do, every problem they solve, every activity they make, is recorded and documented so that if they leave, you can bring on a new apprentice and you don’t have to start from ground zero. You always want your apprentices developing repeatable processes. That’s where the real, long-lasting value for you, as the apprenticeseur.

[bctt tweet=”Always have your apprentices develop repeatable processes that can be utilized by anyone at any time. -Kyle Gray” username=”kylethegray”]

Maybe you’re listening to this and you’re thinking, I would really love to be an apprentice to some high-level marketer, entrepreneur, authority in my space. How do I do that? What do I need to do to make that happen?

First, let’s talk about who should be an apprentice. Again, looking back at what’s being exchanged in an apprenticeship, you, as an apprentice, need to offer your time, your creativity, your energy to another business to really create value for them. So you need to be prepared to dedicate some of your best mental energy and time to the apprenticeship or make sure that when you are moving forward with an apprenticeship, that the expectations are set right.

Some of these apprenticeships may require or request you to relocate. In a lot of cases of location and dependent entrepreneurs, they may have their offices in Vietnam or the Philippines, and you might have to travel to there and live and work with the entrepreneur side by side for the first couple of weeks or months to really be able to fully understand what they’re doing and how it works.

You also need to be prepared to stick with this company for at least a year. Training you for the first few months is probably going to be more of a cost and time energy drain on the company than it is a profit for them. Only after a couple of months when you really get a good feel for what you’re doing can you add a lot of value and make sure that your apprenticeship is successful for both sides.

So, you need to not only be prepared to dedicate a large density of time to your entrepreneur or your apprenticeship that you’re working on, but you also want to be able to be committed to sticking with them for the long run so that you can fully develop and fully immerse yourself in these skills and leave the company that you’ve been working with better than you found it.

Another important point to determine if an apprenticeship is something good for you. You should see your apprenticeship as a boost in your journey, not a starting point. If you don’t have any skills or experience in running businesses in marketing or anything that you can really add value to the entrepreneur right out of the gates, it’ll be really difficult for you to be successful in your apprenticeship. If you are already creating websites, doing marketing, selling products and growing your own business and developing a foundational skill set that you could help another entrepreneur with, even if you’re going to grow and develop that skill set a lot. But if you have something foundational that you can assist them and add value with, then you’re in a much better position to be hired and brought on to an apprenticeship and make sure that you leave a good impact.

A great example of this is Vincent Nguyen. Vincent Nguyen currently runs Growth Ninjas, an extremely successful Facebook marketing ad agency. But, for a long time, he was an apprentice for The Empire Flippers. The Empire Flippers helped buy and sell niche websites and they needed help with their marketing. Vincent started working with them in many different areas of their marketing but began to be really successful using Facebook ads, which was a skill that then translates into his now-successful business, Growth Ninja.

But, before he was hired on to The Empire Flippers, he had a blog called Self Stairway, which was a self-improvement blog that was a high-quality website, well-written content that was getting comments and feedback from people. He had been creating things. He had been experimenting. He had been growing in his skills. And that made him stand out from the many other applicants that were applying for the apprenticeship at the time. It was very competitive. The Empire Flippers are listed in the Inc. top five thousand fastest growing companies right now and have been very competitive for apprentices.

So again, consider an apprenticeship a boost or an accelerator in your journey. If you don’t have those foundational skills yet, develop those and then start searching for these opportunities.

Finally, you want to be able to work remote and stay self-motivated. This was a big challenge for me to learn in the early days of my apprenticeship alongside learning the whole business. Being able to understand how to communicate well in remote work situations, how to write emails clearly, messages and Slack, what other systems can you use to communicate clearly and effectively, and make sure that you are getting all of the work done that you need to get done. Often in remote work situations, you’re sitting there on your own and there’s no direct accountability. So it’s very easy to maybe browse around social media or just get up and walk around or do something else if you start getting bored. You need to be able to manage yourself very well as an apprentice and as a remote employee. It’s crucial to have those skills if you want to succeed in an apprenticeship.

So, if you’ve heard that and you think you’re a great fit for apprenticeships, let’s talk about applying for apprenticeships.

The first, and probably biggest question is where do I find these kinds of opportunities? Not all companies are open to this. I would say that smaller businesses, usually with teams of fewer than ten, and entrepreneurs that rely heavily on online marketing or creating online or remote businesses are most open to apprenticeships and this kind of work. But I do have one specific recommendation of a place you can go to start looking for good apprenticeships. It’s Dot C-O. I will leave that link for you in the show notes. They have lots of different remote work all around the world, apprenticeship or otherwise style positions that could be really unique and a great opportunity for you to further develop your skills and get some experience working with a very interesting company.

One of the most important things that you need to look out for when considering apprenticeships, is you want to avoid any businesses that don’t have a validated idea, don’t have a track record, and are just looking for cheap labor to get their product off the ground. You need to think and find businesses that are already successful, that are already growing, that are already winning. Anyone who comes up to you and says, okay, once you’re in the business, we can finally get things off the ground. It’s exciting to have the responsibility to move a business forward, but, if it’s all falling on you, or expected to fall on you and the big results are expected to come from you, that’s a lot of pressure and you’re not necessarily set up to succeed in that case. And they’re just looking for cheap labor and somebody to solve the problem.

On the opposite note, you want to look for somebody who is a master at a skill that interests you, that you want to develop, that you want to grow in.

All right. So let’s say you’ve found a good apprenticeship offer on or maybe you see a different job posting out there. There are some similarities in the application process of applying for a regular job. And then there are some elements that typically happen in apprenticeships that are unique to apprenticeships, or maybe just a new way of applying for jobs in general.

The thing I’m referring to is typically these apprenticeships will ask you to do a 90 or so second video of you talking about why you’re a good fit for the company. Now, it’s a very common temptation for people who, especially younger, particularly men, who are trying to break into the space to use a video like this to try and be creative, to try and stand out, to try and be interesting. I would really advise against that. I think it’s best to have a video where you are just sitting in front of a camera, speaking confidently and clearly to how you can add value to their business, how you can you help them grow, how you can make the entrepreneur’s life easier and smoother with your skill set. Always focus on what you can bring to the company.

Now, some of you may feel okay, Kyle, this is pretty obvious. Obviously, I’m not going to be so creative and wild in my videos. But let me tell you, as somebody who has gone through these applications, managed these applications, I’ve seen some wild things. I remember seeing a guy submit a video where he’s sitting there, shirtless, taking a selfie video from his iPhone and saying, hey, my name is, I can’t remember his name in particular, and he starts licking his teeth. And he says, I may still have some blueberry smoothie in my teeth from this morning, but let me get started. And then goes on to talk about how he was helping his father’s golf cart business in their marketing or something. Obviously, this wasn’t necessarily an example of somebody trying too hard or being too creative. It was probably the opposite, where somebody was just way too lazy. But that’s just a little example to illustrate how wild some of these videos can be.

I’ve also seen it happen with friends of mine. And worse yet, it’s happened with me. I’m honestly a little embarrassed to share this story, but I’ve got to get it off my chest. This is one of the skeletons in my closet. But, there was a time where I was applying for an apprenticeship to work a marketing job for a resort in the Philippines. This was a famous apprenticeship in some of the circles that I had been running in, and it seemed like a great opportunity. You got to live in a resort, just work ten hours a week, and then you have time to grow your own business. It seemed like a perfect opportunity and a really good fit for me. I was very, very excited about it.

At the time, I was renting a house that had a sauna in it. And I thought it would be clever and funny to make a video where I’m sitting in a sauna typing on my laptop and training myself to be in the heat of the Philippines and working like that. So, we spent a lot of time setting up good lights in my sauna, had a good camera, a good script, and I was putting together all of these things. And, the end product, at first, I thought, looked great. I was very set in my ways. This was an awesome idea through and through. Got it submitted, despite some of the warnings of some of my friends.

But, in the end, I didn’t get the apprenticeship. I actually heard back from them. And they said, hey, you seemed like a great fit, but that video was a little bit weird. And honestly, looking back on it, the video kind of had this weird kind of romantic, sexy undertone being in a sauna and was just not at all what you need to do when applying for a job. I was crushed that I had lost the opportunity by doing something so silly, in retrospect. But, again, sometimes when you’ve got an opportunity that you’re really excited about that you want to apply for, you start to think you need to do these crazy things.

Here’s another look at this. You want to be a good, ideal fit for this business and you want whatever the apprenticeship is to be a good fit for you. You don’t want to see the apprenticeship as, oh my gosh, this is my one big chance and all of a sudden, the Eminem song about your chance and Mom’s Spaghetti starts playing in the back of your head and you feel like this is your only shot at landing an apprenticeship that could be your springboard into success for entrepreneurship. Don’t think of it like that. I want you to see yourself and think of yourself as this is a great fit for me. I’m totally prepared. I’m confident that I can do this job and that I can grow and add value to this company.

A lot of this is just a perspective and a mindset shift. And you definitely want to be of the mind that you can calmly and effectively handle this problem and grow.

For many of us, an apprenticeship may not appear so nicely in a job application and fall right into our laps. For some of us, we may want to create those. You can do that by starting to follow entrepreneurs and businesses with values you admire, who are masters in skills that you want to master, who are leaders in an industry that you want to break into and start following them on social media. Start looking at the content they are creating, start investigating what’s going on in their businesses, and seeing if there are ways that you can add value to them and maybe you can create your own apprenticeship, offering to work for free, for a limited period of time, to prove your value, prove your worth and then, maybe building in a payment plan or something after that.

This is all comes from carefully building up a relationship, adding value, and finding ways to position yourself as the solution to the entrepreneur’s problem.

So now, let’s imagine you’ve gotten your dream apprenticeship. What do you need to do to be successful? There’s a couple of key guidelines I’d like to share with you to kind of close this out for today.

First, again, I want you to be entrepreneurial, solve problems, develop strategies, and always be growing. You need to be willing to always be pushing yourself, always growing, always refining your skills and moving forward. You need to be pushing the limits of your output and your goals and what you expect to achieve in your apprenticeship. You don’t ever want to just get comfortable in a position, because then it becomes a job. An apprenticeship is always something that’s moving, that’s evolving. You are an entrepreneur, you are learning, you are solving a problem, you are creating a system to repeatedly solve that problem. And then you are handing it off to be delegated so that you have time to solve new problems and overcome new challenges facing the business.

Another thing, though I mention this a lot, it’s worth repeating again. You need to be focused on creating value in their business, not in helping yourself. A lot of apprentices will show up to a business and then immediately start thinking, how can I leverage this to grow my product? How can I create these relationships to help me? You need to see what you’re doing in your apprenticeship as part of your business, as part of your brand. This is your first really big, really powerful case study of the work you do in this business will create your legacy. So while you are working on your apprenticeship, you need to be very dedicated to that, not trying to build up your own business, build up your own prowess, through leveraging the apprenticeship that you’re working in.

[bctt tweet=”Your number one focus as an apprentice should be creating value for their business. -Kyle Gray ” username=”kylethegray”]

Finally, you want to build a network. You want to use as many opportunities as possible to connect with customers in the company. This is great if you’re interested in marketing and want to do marketing work. You want to find opportunities to speak with customers to improve your marketing. You want to find opportunities to collaborate with other influencers in the space so that when you leave, you have a network of people who have seen you work, who trust you, who like you, who know you can get results, and who can see the quality that you produce so that more opportunities will come your way as soon as you are on your own and as soon as you are growing your own business. The network is essential and a very powerful part of the apprenticeship process.

In closing, whether you are an entrepreneur looking to bring on an apprentice to help you grow your business and take it to the next level and delegate some of those tasks, or you are an apprentice or an aspiring apprentice who wants to learn from an established authority and thought leader, this is a great system for you. And I wish you the best of luck in finding a great apprentice or apprenticeship and moving to the next level and sharing education and empowerment.

Thanks for listening to the Story Engine podcast. Be sure to check out the show notes and resources mentioned in this episode and every episode at If you want to tell better stories and grow your business with content marketing and copywriting, be sure to download the content strategy template at This template is an essential part of any business that wants to boost their traffic, leads, and sales with content marketing.

Kyle Gray:

Thanks for listening and we’ll see you next time.