The Return of Apprenticeships (And How to Land One)

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 taught myself a bit of Search Engine Optimization using Moz’s Beginner’s Gudie to SEO, a free guide online.
  • I paid $20 to get a hosting account from and built a website in between working my job at the time as an English teacher. Here are some other good hosting starting points.
  • I cold-emailed a handful of marketing agencies and used those sites as proof of my skills.
  • That turned into a part-time internship, and eventually a full-time job where I learned a lot about internet marketing, project management, and technology.

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

  • You want someone to be able to come in and have defined processes and documentation in order to take over your company’s equivalent; it will put them at full-time right off the bat.
  • Create a spreadsheet with three columns.
  • The process to be taken over (Ex. Adwords management, Send Email Newsletter, etc.)
  • The estimated time for one each week, and an estimate of what it’s worth to the company (Defined SOPs should all be defined cash flows with positive ROI to ensure that the position is profitable as soon as possible.)
  • Each task should have documentation built out for it in a pre-defined SOP.

Executive Team discusses job description and SOPs

  • Do we have cash flow to pay for the person for two years including raises, etc.?
  • Is this a Hell Yes? Even a high quality hire usually takes three to six months to get up to speed, so it has to be a Hell Yes decision.
  • How confident are we? Can we prove that defined SOPs are positive ROI cash flows?

Write a Job Description

  • Write it like a sales letter selling the benefits of the position. Far too many companies spend massive resources marketing their products, but none marketing their opportunities when bringing in better people would solve the latter problem, faster.

Post Job Description/Sales Letter

  • Important Note To Business Owners: Don’t oversell the mentorship aspect or you’ll wind up with applicants looking for a lot of your time; the value of the position is “training at altitude.”
  • Application Requirements: Use a centralized form; Google Forms work fine, but you can use Typeform or Gravity Forms as well. The important thing is to get all the applications in one space. Require the following fields:
  • Name
  • Email
  • A two-minute Youtube video — Youtube videos let you get a much better feel for someone than reading a stale application, and many people can be disqualified after employers watch the the first five to ten seconds and ask if the applicant was someone they would ever be willing to have lunch with.
  • Ask them to say why they want the job, why they think they would be a good fit; also ask them to explain any previous projects they’ve worked on that offer relevant experience.
  • This can be posted on Youtube as “unlisted,” and a URL entered into the form.
  • Any position specific questions
  • Include an Instant Disqualifier: Ask applicants to include the word “cafe” in response to one of these.
  • Example: “Include the word Cafe as the first word in response to question 5 — What’s your experience with WordPress?”
  • Link to blog/social media accounts/anything else they want to share
  • Make sure they set the accounts to “Open” or equivalent so you can actually look at them.
  • Skype ID
  • Earliest Possible Start Date
  • Links to Examples of Previous Work; this can be anything they’ve done before (you’re looking for trajectory)

Promote the Job Description

  • Post a copy of the job description on relevant job boards and drive them back to the primary form.
  • Craigslist — Though frequently maligned, Craigslist often has some of the highest quality applicants
  • — Hiring platform for corporate types looking to leave traditional corporate jobs, primarily UK.
  • Your Personal Blog (if applicable)
  • Your Company Blog (if applicable)
  • Relevant Industry Forums
  • Promote it through your personal network — I’ve seen the majority of successful apprentices come through friends of friends, so promote it through Facebook and Twitter. People that are friends or friends of friends are more likely to be a good value match for the company.

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

  • Filter out using the Instant Disqualifier.
  • Usually 80–90% of applicants won’t include the instant disqualifier (starting a response with a certain word) in their application. Inability to follow basic instructions is a great way to weed out people fast and includes a tragically large amount of the general population.

Watch the Youtube Videos

  • Go through the applicant’s’ videos and look through supplemental materials.
  • Gut Check/Gut Sense — What’s your thin slicing/gut impression? Delete everyone that you wouldn’t want to go to lunch with.

Criteria for evaluation — Set-up a spreadsheet and grade each of the following a scale of 1–10

  • You want someone that’s focused on business and long-term growth — not just getting out of a job they don’t like.
  • What have they done? Best predictor of future success is past success.
  • Heck yes or no — Do they have the potential to be best-in-class at their position in three to five years?
  • Do they match up with the company’s core values?
  • Must have a positive outlook — moving towards motivated, not away from it. Warning signs are talking bad about their current condition and how they are trying to get away from it.
  • Get your list down to the top four to twelve candidates for interviews depending how many applicants; there is typically always a clear top tier of applicants that are worth interviewing, and usually constitutes 3–7% of the total applicant pool.

Set up interviews with top candidates

  • Schedule aggressively; don’t let the hiring process drag on if it can be avoided.
  • Send a link to all applicants you want to interview and request that they choose from the available time slots. Tools like Schedule Once and Calendly will let you set up available times for them to schedule.


  • Preparation and Guidelines
  • Re-Watch their video once more and jot down any specific questions for them
  • Request a video interview rather than audio; a lot is communicated via body language and nonverbal cues
  • If you smell fish in the application, go after it
  • Dig into past experience; past success is the greatest predictor of future success
  • Start with three to five minutes of small talk to get them comfortable

Primary Questions

  • Why do you want this job? What’s most valuable and exciting to you about this opportunity?
  • Evaluating for: Long-term focus? Business focus? What do you know about our company? Are our values the same?
  • What motivates you? What gets you out of bed in the morning?
  • Evaluating for: You want to figure out their “WHY.” Watch out for running away from problems; look for people pursuing opportunities.
  • Where do you see yourself in five years? What are you long-term goals and objectives?
  • Look for high trajectory, ambitious individuals.
  • What experience do you have relevant to this position?
  • Evaluating for: A better feel for their domain expertise
  • Domain expertise is usually one of the factors lowest on my priority list
  • What’s the most difficult thing you thing you’ve ever accomplished? What are you most proud of?
  • Evaluating for: How they actually interacted in a real-world situation and what they consider difficult. Again, “people that have done stuff.”
  • What have some of the biggest influences on your life been — could be books, people, events, anything.
  • Evaluating for: Inflection points
  • Are they on a steep trajectory or are they doing roughly the same stuff now that they were five years ago?
  • Do you have any questions for me? Any questions about the position?
  • Evaluating for: They should take an interest and show they’ve actually thought about the position and how it matches up with their skillset and trajectory.

Special Circumstances Questions

  • For the people that are farther along: Why do they want this job?
  • Are you committed to staying for at least a couple of years?
  • Do you know it doesn’t pay a lot?
  • If they’ve been in the game a long time and haven’t made anything happen, figure out why.
  • Ask any additional questions based specifically on their application
  • Record Notes/Thoughts
  • At the end of the interview, write down notes and thoughts on the candidate.
  • Re-grade them on a scale of one to five on the following five criteria:
  • Past Work — What have they done?
  • Doesn’t necessarily need to be domain specific; look for motivation and work ethic.
  • Again, the best predictor of future success is past success
  • Trajectory Personal and Business) — Where are they going? Does it align with where the company and position are going?
  • Value Match — Do their core values align with ours? (Most important)
  • Domain Experience — Do they have relevant domain experience? (Least important)
  • Gut Check/Gut Sense — What’s your thin slicing/gut impression?

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

Originally published at on July 3, 2015.

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