TMBA 270: A Roundtable Discussion on Apprentices, Mentoring, and Team Building

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Our old friend and former team member Taylor Pearson from has come by this week to help us have a broad, round-table conversation about team building. We talk about the ways that Ian and I have done it, and Taylor shares some insider insight about being on our team. We also answer a question from a young listener about whether he should be learning a skill set like SEO or diving headfirst into his own business.

Listen to this week’s show and learn:

  • The benefits of “Training in Altitude” and “Playing with House Money”.
  • Why we don’t generally hire 30 year-olds.
  • Our definition of an “Open Door” management policy.
  • Why we believe in the “Six Months to Michael Keaton” approach.
  • When to hire a contractor and when to find a full-time employee.
  • Why we are returning to the era of apprenticeships and why that works better for everyone involved.

People on this episode:

Mentioned in the episode:keaton_website_0

Listening options:

Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST. Cheers, Dan & Ian

Published on 11.13.14
  • This was a great episode, just one month into my apprenticeship this really gets me excited to keep digging in and go through “open doors”. I think the first phase of the apprenticeship is difficult for both parties. It sounded like you guys briefly talked about this in regards to Taylor’s first six months. Learning the culture and expectations and just generally provide a net benefit is slow, and that road is paved in mistakes. The training is certainly a big up front time and effort investment for the boss. But I am grateful that I have the opportunity and just try be humble, work hard, listen, learn and absorb everything before I try add my own spin on things.

    How do you guys think someone like Frederick who is applying for their first apprenticeship can demonstrate their good trajectory instead of a specific skillset?

  • Back in my junior year of high school (1996), I was able to score an apprenticeship through a school program that allowed me to work in the engineering and IT department of a pharmaceutical company two days per week, about 16 hours, which I got paid $12/hr for. Truthfully I was willing to work for free. I learned a ton about a lot of different things, both in technology and corporate life… at age 16!! I learned early that I didn’t like the corporate world. So in my senior year I went to work for a small business as an apprentice doing IT type stuff and was paid $15/hr for two full days during the week and after hours. Learning more about real world IT and running a business. All with my night “side hustle” selling computers, TVs and home entertainment products at SEARS at night (massive sales education!). I also took Microsoft, Cisco and Novell certification classes at night and got certifications in each BEFORE graduating high school.

    I turned down a full ride to Penn State to start my own IT business upon HS graduation (1998). I went to a local college instead to get an associates degree, which I’ve never needed to use. I knew with the AS degree and my tech certs, I could get a job making great money if my business didn’t work out. I grew my IT business from 2 customers to 400 customers and sold it in 2010, to focus on another business, Municibid (my current company), that I started in 2006, which continues to grow.

    TL:DR Play with house money to get started.

  • My last year in college, one of my professors had a guest speaker and he said to us “Don’t look for your first job out of college, look for your first boss.”

    That strategy has worked out pretty well for me so far :)

  • Jeff

    No one wanted to call this Return of the Apprenti, eh? I’ll show myself out…

  • Danny Michlewicz

    Great episode. I have a friend who worked at Google, he said they really like folks to stay 3 years, they really get their return on training that 3rd year..they dont quite get 3 years on average from employee, but thats the goal.

    Im sure you guys have talked about this before – but being able to have team members that know the entirety of your business is really valuable when it comes to training new employees – its not just you training and teaching culture, you can get a lot of help. Dont know how you organize your businesses in terms of roles, hierarchy, do you talk about it on any episodes?

    Cheers from Medellin!


  • Check out “The Alliance” by Reid Hoffman. He talks about “Tours of Duty” and clearly aligning team members goals & ambitions for their trajectory & the company’s plans. Great stuff.

  • Working my way through it right now, feels like a classic fluffy business book? Everything . is . taking. so long. Stick with it?

  • Damn thanks for sharing your story Greg I’m sure others will enjoy reading it. If I would have gotten a full ride to PSU there would be absolutely no way around it! Very brave and great illustration of what can happen if you focus on building real know-how.

  • I like that, found myself repeating it in the last few days.

  • Hey Kyle thanks, the biggest thing re: trajectory is to demonstrate that they would be doing it anyway, ie, our trajectories align. ‘hey man, if you don’t hire me I’m sure somebody else will. I’m writing blog reviews for you, but even if you don’t’ take them i’m sure somebody else will etc’

    Too many candidates only activate for the opportunity. You need to be ‘doing it anyway.’ (As you were by the way!).

  • HA! inside baseball :D

  • hey Danny great to hear from you, our organizations are currently very small and mostly flat… I’m not sure we have a strong point of view on this topic honestly, it’s more about personalities and tasks than a framework we have in place currently (I think!)

  • There’s probably not a whole lot for you as you are already a “believer” but I have found it very helpful discussing with people in the new gig as a way to transition from the new world order to the old.

    Also audible on 1.5x is your friend for Biz Books.


  • noted there! I’m so into the pleasure of audible, but i suspect i could benefit from some particular strategies for harnessing effort etc.

  • John Hooley

    Interesting episode guys. Along the theme of living at home, not getting laid, and having your “fingers in the pie”… this may be the prototype TMBA intern:

    One thing on the mafias… the assumption is that they’re successful because they’re training at altitude, and I’m sure that helps, but I would question whether the smart people at Skype and Paypal didn’t select winners to hire from the get-go. I.e. these people were likely going places with or without a boost.

  • Danny Michlewicz

    Ok, what set of the question on organization are a few things Ive been pondering:

    1. Youve mentioned that once businesses evolve to hit midseven figures and higher, much of their success is based on strategy, and execution of strategy. It cant be the one man show anymore. Growth of the business stops being so much about guts and passion, and about execution of a strategy, seeing the vision through in its different facets.

    2. Ive remembered reading before and tucking away in the back of my mind, that CEOs that are number-savvy are most valuable once you are hitting $50 million revenue and higher – a company can make it without a strong financial backbone until that point, but afterwards, without strong financial leadership it starts to suffer relatively speaking.

    So my thought is, as your business gets more complex, have you guys at any point made sure the complexity does not outgrow you. Have you hired folks that made you more competent in dealing with execution of strategy, finances, and execution of market analysis – a combination of CFO, COO, CMO responsibilities in say a 25 person silicon valley startup?
    Or have you sunk resources into making yourselves those competent people within your company, hiring other folks to do tasks you previously did that are less valuable? And whatever the answer is to that, how did you organize it and plan it? For example, took 2 years for the Work the System guy to really build out his processes to organize his company. Interested to see what others think and want to share.

  • haha ! yeah i agree it’s tough to say, my sense is the network has something to do with the winning (access to info/resources) but we’ll never know !

  • Hey Danny regarding point #1 that is my current supposition, for example, much of our growth depends on the markets we’ve chosen and our systemic competitive advantages as opposed to in the mid six figure period where we could really move the needle by “bench pressing” the business… i guess big growth would happen not simply by doing more but by doing better (strategically).

    On point #2 we are defo hitting a lot of “Peter Principle” spots in our business, in particular in regards to finances and wealth management… its very timely that you’ve brought it up we’ve honestly talked for hours (days) about it I’m not even sure where to begin. HOW DO WE FIND THESE PEOPLE!? :D And our business is at a weird level where somebody who knows all that stuff and could teach us it (or build it into our business) might not create ROI in our environment… the short answer for 2015 is that we are seeking to invest in ourselves rather than bring in experienced ‘consultants’ or clevel employees, our primary strategy will be mastermind and meet-ups

  • I’m currently 17 and running my own freelancing business full-time. I’ve started to build some assets, but honestly–I have no apprenticeships, and I feel like I’m lagging behind unless I get on one. Other than cold emailing about what you can offer, how do you find an apprenticeship?

  • hey Radhika wow nice work. It’s a really tough one to answer, no site to my knowledge effectively curates a list (at least of the type of apprenticeships that I’m talking about) and I think there’s structural reasons for that, however, this video has always been my favorite resource:

  • Thanks for the quick reply, Dan. I love Charlie’s work.

    Why do you say there are structural reasons for there not being a centralized list?

  • hmm… might have to dig into this one in more depth… i think it’s probably possible to try, we had tons of quality issues, IE business owners using them to get cheap work etc etc

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