The Return of Apprenticeships (And How to Land One)

By Sean Ogle •  Updated: 07/03/15 •  20 min read

This is a guest post from Taylor Pearson. I really believe in the apprenticeship model, and I owe a big part of my success today to work I did with Dan and Ian of the Tropical MBA a few years back.

If you’re thinking of bringing someone new on board, or you’re looking for a slightly less traditional work relationship – read on.

Also Taylor’s new book “The End of Jobs” is available for free for one more day, so go check it out!

After his release from jail, James wasn’t terribly grateful to his brother Ben for running his business while he’d been doing time.

Upon release, he not only harassed, but beat his younger brother.

Not a good start to an apprenticeship.

Ben decided to hop a boat and head to New York before making his way to Philadelphia, where he would go on to found one of the most influential newspapers in colonial America and the business that would bankroll his travel around the world – and do it during a time when most people never left their hometown.

For thousands of years, careers and businesses were started not by people getting degrees, but by people getting apprenticeships.

While Benjamin Franklin’s career start as an apprentice in his older brother’s print shop was less than ideal, it did let him acquire the skills and network he needed to launch his own print shop and eventually move into politics and foreign affairs.

In Medieval Europe, it was traditional for aspiring tradesman to apply for apprenticeships with a master of their craft. They would go to work in the master’s shop, usually for around seven years, before passing into the journeyman phase where they were required to do a project that they would submit for review to their prospective guild. If they passed, they’d be accepted as a master who could start the whole cycle over by taking their own apprentices.

For hundreds of years, this was the way skill sets were passed on among families and communities.

In that sense, apprenticing today works on the same premise as it always has—it’s a way to build skillsets and relationships.

The premise is pretty straight forward:

You find someone that is currently doing what you’d like to be doing in five years time: “I’ll come work for you for and I’ll create results you would normally have to pay a lot more for, and in exchange I get to train at altitude. I get to see the inside of how your business works: How you launch products, what the industry looks like, and who I need to know.”

Instead of playing with your own money (like what you would need from consulting, a job, or savings), you play with house money.

Apprenticing was how I got started in entrepreneurship.

I went and worked in another small entrepreneurial company for two years, where I got to move from SEO to Marketing Manager to running a small division.

I was able to acquire entrepreneurial skills by being on the inside of an entrepreneurial company.

Charlie Hoehn originally worked with business coach Ramit Sethi and then author Tim Ferriss as an apprentice for a few years before publishing a book, Play It Away.

New York Times bestselling author Ryan Holiday apprenticed for Robert Greene, author of five international bestsellers, before launching his own best selling book, Trust Me, I’m Lying.

I’ve seen dozens of other entrepreneurs like Sean come up through an apprenticeship in much the same way.

Despite an astounding track record over the past decade (or even the past few millennia), both companies and potential apprentices seem to undervalue the potential of an apprenticeship.

Having now been on both sides of the fence, being hired as an apprentice and hiring apprentices, I’d like to make a case for why that should change and the advantages both sides are missing out on as well as give a practical guide on how to get started.

Advantages of Apprenticeships to the Apprentice


One common mistake early entrepreneurs make is that they think they need a business idea. That’s rarely the case: you don’t need a business idea—you need relationships.

As you acquire relationships and entrepreneurial experience, ideas will become a bigger problem, but not in the way you think. Experienced entrepreneurs frequently deal with “shiny object syndrome,” a phenomenon where they see too many opportunities and have too many ideas, and not enough resources to pursue them.

I’ve never met someone that has a lot of strong entrepreneurial relationships that was hurting for ideas. Samuel Hulick got started by working with Rob Walling, a more established entrepreneur, when Rob was launching a new email marketing company.

By doing a brief apprenticeship, he realized that user onboarding for SaaS apps was a major pain point, so he launched to help SaaS companies with their onboarding process.

More Effective in Complex Environments

When I first began working for other entrepreneurs, I was shocked when they would commit tens or hundreds of thousands dollars towards “gut” feelings. Just as high level athletes will travel thousands of miles and upend their lives to go train with the best people in their field, apprenticeships let you be around people who have developed the gut feelings and mindsets that can’t be articulated in a text book.

In an interview with Jason Calacanis on This Week in Startups, LinkedIn founder Reid Hoffman looked back over his career and cited his biggest career mistake as not leaving Microsoft for Netscape.

At the time, he believed it was important to learn to be a product manager and there was no way he could have become a product manager at Netscape, so he stayed at Microsoft.

Looking back, he said that he should have gone to Netscape as a mail clerk. At the time, Netscape was where all the innovation was happening. It was spouting out entrepreneurs.

The right questions wasn’t “how can I learn to be a product manager?” It was, “how can I get in the building at Netscape?”

Better Value (a.k.a. Play with House Money)

Unlike graduate school, or in some cases a college degree, apprenticeships allow you to get paid and build a more valuable skill set and relationship. Instead of paying six figures to go to law school or get an MBA, you can get paid to learn skills valued by the marketplace.

Advantages of Apprenticeships to Entrepreneurial Companies

As the broader market reflects, the demand for entrepreneurs and entrepreneurial skills is higher than it’s ever been.

Currently, the demand for apprenticeships far outstrips the supply. Many people still early on in their entrepreneurial careers are looking for apprentice positions, which gives entrepreneurial companies a tremendous opportunity.

It’s certainly important to have tight hiring practices, as many applicants fall into the camp of people who like the idea of being an entrepreneur, but may not be willing to make the sacrifices. There’s a large number of people who are willing to make the sacrifices and do the work at an exceptional value.

Less risk for employers

A large part of the employment model as it exists today is built on a traditional model where companies expect to hire someone and retain them for the majority of their career. As a result they end up investing heavily in new hire for the first few years, expecting the investment to pay off in the long run.

What frequently happens instead is that employees come into a company, get the benefit of being trained and then leave the company for another opportunity. Companies react by getting upset and respond by working on better retention programs.

Instead of companies getting upset because people leave, why not rework the equation to plan on people being there for two to five years instead of twenty to fifty? Instead of trying to swim upstream with better retention programs, companies can adapt by creating apprenticeship programs.

Agreements can be structured around the basis of having people come in for pre-structured timelines.

If you know someone is only going to be there two to five years, you can negotiate a contract where both parties win on that basis, usually by paying less money up front but giving them access to industry knowledge and relationships.

You attract higher quality applicants.

If you measure the output of a sales team of ten people, it will inevitably fall close to the 80/20 rule.

Two of the ten will generate around eighty percent of the sales. While the difference in impact is most obvious in a role where numbers can be closely tracked—such as sales—apprenticeships are built on the idea that if you can bring more of the most talented individuals into an organization, albeit for a shorter time, the output will make it more than worth it.

Apprenticeships enable entrepreneurial companies to bring in young, talented, hungry individuals to make a trade.

The young entrepreneur agrees to give their best energy in growing the company for a few years and see it as an investment in their entrepreneurial future.

The employer is able to bring someone into the company that isn’t looking for a traditional job, but is happy to invest in themselves through working for someone else that will help them reach their potential exchange by building relationships and a skill set at a value employers couldn’t get in the general labor market.

You build an alumni network of smart, ambitious people.

Another advantage that companies have seen is the creation of alumni networks and networked intelligence. Ambitious former apprentices go on to build their own companies or work with other entrepreneurs, gradually creating more relationships to tap into.

We’ve seen this model before in coaching trees.

Great sports coaches like Bill Belichick of the New England Patriots have long used the apprenticeship model. They make an offer to young coaches: instead of taking a second-tier head coaching job, come take a top-tier assistant coaching job for two to five years. The young coaches have an opportunity to study and experience a championship system and build relationships with the other coaches. The experienced coach is able to bring the most talented young coaches to inject new innovation into their systems and slowly build a network. If you look at the current head coaches in the NBA or NFL, the 80/20 rule applies. 80% of them usually have common roots in apprenticing with 20% of the head coaches of the past generation.

Technology startups have started to develop “mafias,” or groups of successful entrepreneurs that can trace their roots back to a common source. Elon Musk (Currently of SpaceX and Tesla), Reid Hoffman (LinkedIn), and Peter Thiel (Palantir) all worked together at PayPal.

Trajectory Theory – A Guide to Hiring an Apprentice (or Getting Hired)

Three-time New York Times bestselling author Tucker Max has hired a lot of people to work in an apprentice-type position, and they’ve almost always gone on to be successful in future projects and companies. Why is his track record so good?

In his words, he hires “people who have done things.”

I apprenticed at one company that I had already interviewed with for a job nine months earlier. After the first go around, they told me, ”You’re pretty smart, but you don’t really have any applicable skills.”

So I started building websites about home furnishings and selling advertising space using Google’s Adsense program on them. That led to the working with a local marketing agency.

When I re-applied for the apprenticeship they’d seen that I built a few websites and used that to work at a marketing agency where I became a project manager.

They saw that as trajectory and hired me.

The Apprenticeship Hiring Process

Here’s an example of a process I’ve used before to hire for an apprenticeship position and that I’ve seen many other entrepreneurs use before. If you’re looking to apply for an apprenticeship position, this is the criteria you’ll be graded on.

Define Standard Operating Procedures that Apprentice will take over

Executive Team discusses job description and SOPs

Write a Job Description

Post Job Description/Sales Letter

Promote the Job Description

Allow two to three weeks for applications and actively market the position.

While it’s live, actively market the position to get as many applicants as possible. Effective filtering will let you get down to the most qualified candidates later so the more applicants, the better.

Application Evaluation

Set up interviews with top candidates


If you’re looking for an apprenticeship grade yourself on the five criteria above. Do you have a history of work you’ve accomplished to show? Are you on a trajectory that would make you attractive to hire as an apprentice?

If you are on that kind of trajectory, the truth is that an apprenticeship is almost unnecessary, you’re already well on your way.

What’s scarce today isn’t domain knowledge, all of that is accessible for free (or cheap compared to a $100,000 degree). What’s scarce (and valuable) is people who take initiative and make things happen.

The rapid development of technology and globalization has changed the leverage points in accumulating wealth.

It’s the entrepreneurial individuals that understand the new paradigm and have taken advantage of it to create unprecedented wealth in their lives and the lives of those they love.

While models like apprenticeships are taken off, the notion of jobs, of work as obligation, of following orders is coming to an end. That’s why I wrote The End of Jobs, to show people that entrepreneurship isn’t just more fun, it’s safer, more accessible and more profitable than widely imagined.

For the next few days, I’m making the book completely free. After the first few days, however, Amazon will force me to charge people for the book.

You can download it here.

Image Credit: Anvil by Big Stock

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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15 comments on "The Return of Apprenticeships (And How to Land One)"

  1. GarinEtch says:

    I love it! I have 3 part time jobs now that are essentially apprenticeships, where I get to learn from my role models and add value to them.

    My $.02: an apprenticeship is the same thing as “a job working for someone you look up to and want to learn from.” Many people think of an apprenticeship as easier or less demanding than a normal job. It’s not, there’s no room for slacking off. You have to work twice as hard to learn as much as you can and prove yourself.

    Thanks for the great post!

    1. GarinEtch says:

      And one other thing, I landed my gigs by doing James Altucher’s method of sending 10 ideas to people. That started the conversation, and once my foot was in the door I wiggled my way inside until I had an official paying gig. Highly suggest that method for anyone else looking to create an apprenticeship for themselves.

      1. Taylor says:

        That’s baller! You should email James and tell him that 🙂 – I’ve done that 10 idea journal thing a few times on and off. I like to do it whenever I feel “stuck” as it reminds me how many opportunities are out there.

    2. Taylor says:

      I would agree with your definition of apprenticeship. The main thing I think about with these types of positions is that they accelerate trajectory which, as you point out, necessitates a pretty demanding situation.

      1. GarinEtch says:

        BTW I just finished your book. I really liked it! Tons of good stuff, I took pages of notes.

  2. Liz Froment says:

    Love the post, Taylor. I am personally a huge advocate for the apprenticeship model (and have to say it’s worked out well for me so far)! Working with an established entrepreneur like Sean has been one of the best decisions I’ve ever made both personally and for my own business growth trajectory. Excited to read the book.

    1. Taylor says:

      Thanks Liz!

      Obviously evangelical about the model myself 🙂

      Looking forward to hearing what you think about the book!

  3. I love the opening example involving Benjamin Franklin. His autobiography is one of the best I have read (and Walter Isaacson’s biography of Franklin is also great).

    I’m thinking about how this apprenticeship concept would fit to my current context. Food for thought!

    1. Taylor says:

      +1 for Isaacson’s biography – that’s where I got the story from. I haven’t had a chance to read his autobiography but it’s on my list.

  4. Liza Davis says:

    Lovin’ it – Good solid, actionable information for both sides of the employee/employer divide.
    My only comment – is HEY, enough of the “young” stuff : ) I think it is a mindset, more than a chronological reality at times. I happen to be an “ancient”, 51 – at least that is the way I saw it when I was in my 20’s, 30’s. Yes, you want innovation, energy and vision. And believe it or not, people, even my age and older have that : ) And there are people who have been really successful in one area and are hungry to try on a new life adventure – just when 20-30 somethings imagine they should be getting ready to wrinkle up and lose steam.

    I have to agree that, yes, there is a tendency for people 40 and up to not “get” all the changes that are happening in the world thanks to a younger crowd, but there are plenty who do and are LOVING it! Just putting you on gentle notice : )

    1. Taylor says:

      Thanks Liza!

      And areed, meant it totally as a state of mind 🙂

  5. Value bomb alert!

    Man I’m glad I read this today. It’s funny, you mentioned to me in a chat that so many people place a stigma on apprenticing or interning for someone more successful.

    I’m looking at all of the super successful and inspiring entrepreneurs that I want to emulate, and I can’t find ONE that didn’t learn the ropes from someone much further down the path of success and experience.

    The ego and even previous more “traditional” success can be an obstacle. I’m totally guilty of this. Since I came into the online business arena early last year, it’s been all about learning and relationships.

    Am I a millionaire yet? Not even close!

    Do I feel stoked and lucky about all of the incredible relationships I’ve managed to build up in the last 18 months?

    Hell yes!

    Looking forward to our call next week, Taylor.

    1. Taylor says:


      I always think about trajectory. If working for/with someone else would accelerate my trajectory, that’s all I care about.

  6. Adam Jalal says:

    I just finished your book. I wish I had read it when I was at Uni. Now that I’m starting a business I know an early apprenticeship with a smaller entrepreneurial company would had been beneficial, but nobody told me at that time.
    I also liked the 90 days framework idea. I am currently using a 3 months deadlines framework, but now I will merge some of your ideas into it.
    Great book!

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