Taylor Pearson
Mar 5, 2018 · 6 min read

In my book, The End of Jobs, one of the paths that I talked about for people trying to get started in entrepreneurship was to find an apprenticeship.

Put simply, an apprenticeship is a paid job that prioritizes your learning and long-term career trajectory by working with established entrepreneurs to develop a valuable skill set and business relationships.

By taking on an apprenticeship, you get the opportunity to ‘train at altitude’, while also being paid. Instead of learning entrepreneurship on your own dime, you get your foot in the door at a fast-moving startup or online businesses where you have more resources and opportunities.

Author and angel investor Tim Ferriss put it this way:

“If you optimize for money too early, you will be minimizing for learning, almost without exception,” he said.

“So look at the first few years out as an apprenticeship where you cover your costs,” he said. “And if you’re looking in business, I would say, be in the room as much as possible to observe the decision-makers and dealmakers.”

I believe in apprenticeships because it worked for me. I spent two years working with a fast growing, multi-million dollar business and learned more than some people I knew who had gotten MBAs.

In exchange, I’d helped the company grow one of its product lines by over 5x in an 18 month period.

It wasn’t just successful for me though.

Charlie Hoehn began working with Ferriss as an apprentice in 2008 and helped Tim launch a New York Times Bestseller by 2010 at the same time as he launched his career.

Vincent Nguyen started doing an apprenticeship for business brokers Empire Flippers, and within three years was running a multi-six figure consultancy for Facebook ads.

It’s not just for young 20-somethings, either. Elisa Doucette took an apprenticeship role as a way to make a career transition from insurance sales to novelist and editor. Now she runs a content editing agency and writes novels.

The Case for Apprenticeships

More than at any other time in history, the career landscape today is at once full of both opportunity and peril.

Never before has there been a time where a single individual can create as much of an impact as they can today. The technologies of the last two decades have created immense new possibilities for our careers, but with a corresponding increase in uncertainty.

The challenges these new technologies pose are well documented: job displacement, automation, and an increasingly competitive global job market.

Less remarked upon is that these same trends create a tremendous source of leverage for those with an entrepreneurial skill set. Never before in history has it been so cheap to start a business that has the potential to reach around the world.

Apprenticeships offer a path to navigate the most complex work environment we’ve ever faced, by teaching us how to build an entrepreneurial skillset.

Today’s world demands hands-on-the-wheel experience that can’t be elucidated through university degrees or online courses alone.

Apprenticeships are the best answer we have for acquiring the valuable entrepreneurial skills that are becoming essential to succeeding in today’s career landscape.

How Do I Find An Apprenticeship?

The trouble is that apprenticeships can be hard to find. After I released The End of Jobs, one of the most frequent questions I received was, “How do I get an apprenticeship?”

So I started sending out occasional emails to readers whenever I heard about a good company hiring.

In early 2017, I discovered that some of the emails I had sent out turned into real apprenticeships for others, and these opportunities changed the trajectory of a handful of apprentices’ lives and entrepreneurs’ businesses.

In April 2017, I hired Matt to help me turn our ad hoc mailing list into a fully fledged apprenticeship job board.

We replaced the random mailings with a weekly opportunity newsletter with the best apprenticeship positions from around the web, which continues to this day.

We created GetApprenticeship.com’s apprenticeship job board, to let employers post openings and for apprentices to browse them.

Finally, we contacted employers who might be interested in hiring smart, ambitious talent for their organisation. This was around the time we got in touch with Russ Perry, CEO of Design Pickle and Jar.

Russ had already built successful service businesses and was looking for an apprentice to help him get a new software company off the ground.

When we announced Russ’s apprentice position, we couldn’t possibly have anticipated higher quality applicants than the ones we received. It turned out getting paid to receive mentorship from an experienced entrepreneur, build a valuable skill set, and work remotely was a compelling offer that interested a lot of very qualified people.

In Russ’s words, the applicants were “So great, we actually hired two people!”

We interviewed Corrin, one of the apprentices, a few months after Russ hired her.

She had this to say:

“A normal job or learning on your own is like reading from a chemistry text book and knowing what should theoretically happen when you mix two things together.

An apprenticeship is like having a full stack lab with all the tools and compounds you need and being able to run experiments to see what really happens.

Having been on both sides of the table, I can tell you that the latter is way, way more fun.”

Since then, we’ve refined our processes and placed apprentices in entry level marketing, sales, and operations roles in startups and small online businesses.

The whole time, we’ve been eating our own dog food. Matt, an apprentice, was running a business placing apprentices. What better proof of concept is there than that?

Other apprentices, like Mark Friesen, shared what he valued most from his experience:

“I recognized the risks involved with a traditional path, and was looking for ways to transition and demonstrate skills in a new field…

…I have long seen the value in apprenticeship, without a clear path to pursue it.

If you’re looking for ways to gain experience in a new field and connect with some great opportunities, check out Get Apprenticeship.”

Employers like Owen Franklin have also told us:

“Hiring an apprentice has quickly delivered results and taken work off my plate so I now have time to concentrate and think about growing my business.”

Why Apprenticeships Matter

Today, apprenticeships still seem novel. In fifty years, we will look at apprenticeships in much the same way as we look at an undergraduate degree today. It will be a default part of a smart career path.

Apprenticeships create a win-win opportunity for individuals in a fast-changing career environment and companies around the world. Apprentices get paid to learn valuable skills that will serve them over the long-term, while giving employers a way to recruit talented, motivated team members.

If you’re interested in getting involved, we’re actively working to connect even more startups and online businesses with talented and motivated apprentices and would love it if you joined us.

Employers can find out more about hiring a rockstar apprentice here.

If you’re looking for an apprenticeship, it’s free to sign up to hear new positions as they become available.

These are apprenticeships like a current one with Owen of FCS, where you’ll learn what it takes to run a 7-figure e-commerce business, work remotely with an experienced mentor, all while getting paid for the privilege.

Or, you can check out this apprenticeship with Jacob from DEO Dental Group where you’ll learn everything about digital marketing, receive priceless mentorship from the CEO, enjoy the benefits of remote work and, again, getting paid while you do so.


In today’s world of rapidly changing technology and uncertainty, career scripts once safe have begun to collapse. It’s a change that’s evidenced through millions of jobless graduates carrying mortgage-sized debts with nothing tangible to show for it. It’s shown in millions of dismayed employers — unwilling to take on the extra risk of training someone who might not stick around.

Apprenticeships provide an answer for both. Apprentices gain practical skills while employers gain tangible ROI. Everything old is new again.

The Mission

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple. Mission.org

Taylor Pearson

Written by

Author and entrepreneur. Into history, complexity, productivity, and blockchains. Don’t have all the answers, but happy to share what I’ve learned

The Mission

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple. Mission.org

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