97: Public Coaching Kickoff: Introducing Our Stars As They Begin Their Quest

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The Idea

I’d been trying to figure out a “quest” for Side Hustle Nation readers and listeners to follow along with, with the theory that it would make the site “stickier” and more compelling just a collection of articles and interviews.

There would be a story or a journey to follow, and where this really hit home was when Bryn and I binge-listened to the Serial podcast on our drive home from Christmas.

If you haven’t listened to it, it’s an extremely well-produced podcast that revisits a real-life murder trial from about 15 years ago. The story-telling and the characters involved make you want to find out what happens next.

Could I try and create something similar for Side Hustle Nation? (Without the murder!)

Then, when I surveyed readers in January, there was a lot of interest in a “public coaching” project. So here we are!

A week or two later, I put the call out for applications.

The Application Process

In the application, I asked a number of questions, like:

  • What relevant skills or experience do you have?
  • Have you ever made money outside of a day job before?
  • What would you like to work on this year?

I also asked, “Gun to your head, what would you do to earn an extra $500 in the next 30 days?”

The reason for this question is that constraint breeds creativityI’m confident everyone with the means to read this would be able to figure something out to earn that $500 if it truly was a life or death situation.

But since it’s not for most of us, we don’t always take action.

By far the best response I received to this question came from Mike Greig:

“I go Bruce Lee circa 1970 on the guy holding the gun. Quick chop, headspin roundhouse kick…now I’ve got the gun. I’d leave the assailant alive but immobile, take the gun and pawn it to make my $500.”

I also asked for a max. 3-minute video to create some small barrier to entry that people had to jump over to show they were serious, plus it gave me a chance to gauge personality compatibility since it’s really tough to gauge that from black-and-white text responses.

In total, I got almost 80 applications! I was expecting closer to 20 so that was a big shock — in a good way.

The Selection Process

As far as selection criteria went, we looked at a number of factors. (I say “we” because Bryn helped me go through the videos as well.)

We had to weigh a candidate’s experience, their side hustle gameplan, their personality/relatability on the video, their demographics and location, and more.

It was actually a pretty stressful process because it was so difficult to narrow down the list.

3 Common Themes from the Applications:

  1. Whether or not you pick me, this is my year. I’m going to make it happen!
  2. Thank you for making me a do a video and forcing me out of my comfort zone.
  3. I’ll be following along with whoever you choose.

Some of the videos I received were REALLY impressive!

Take a look at Dave from Kindlepreneur.com for example:

(The audio quality was messed up, but I know this took HOURS to create and edit.)

But if there was a prize for “Best Produced” it would have to go to Julian in Atlanta. Check this out:

Introducing our Star(s)

In the end, I couldn’t pick just one winner, so instead we’ll have two awesome side hustlers to follow along with.

Meet Kathryn

Kathryn is a commercial real estate appraiser in Portland, Oregon. She blogs at The Verdant Home and is starting a gluten-free baked goods company.

Kathryn impressed me with her energy, confidence, and fun-loving attitude in her application video.

2015 Goal: $1500/mo.

Meet Wellington

Wellington is an engineer for a construction company in New York, New York. He’s working on a travel hacking app and occasionally writes restaurant reviews at WellFedNY.com.

He’s made a grand total of $0.07 online — and sent me the AdSense screenshot to prove it.

lifetime adsense earnings

My favorite soundbites from our intro call:

  • “Sometimes I literally sprint home to work on my side hustle.”
  • “I don’t want to trade time for money.”

2015 Goal: $2500/mo.

wellington intro pic

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This isn’t your typical episode of The Side Hustle Show, but I hope you’ll listen in and follow along with the side hustle journey of these two as we progress through the year.

On these first intro calls, I’m probing to find out what Kathryn and Wellington have cooking (literally, in Kathryn’s case) for their businesses and what they’d like to achieve with them by the end of the year.

With that goal in mind, it becomes easier to reverse-engineer a path to get there.

If you have any insight or input on either of their projects or on this “public coaching” project itself, please leave a comment below!

6 thoughts on “97: Public Coaching Kickoff: Introducing Our Stars As They Begin Their Quest”

  1. Julian’s video is incredibly moving and well done. His daughter is adorable and I was practically moved to tears because the video was so sweet! Congrats to the winners, but based on the video alone I wish Julian was picked! I’m bummed, but look forward to following the SHN public coaching journey!

  2. Good luck for all three of you, seems to be a great journey coming up for all of us to learn from.
    Kathryn – my immediate recommendation will be to work on the imagery on the site – we eat with our eyes a lot, and the images are a little glossy so they don’t look that appealing.

  3. Great podcast! Kathryn’s personality jumps off the screen and Wellington is great as well. Looking forward to follow along in their journey.

  4. Sounds like you put together a nice “team”. I’m definitely looking forward to seeing where the app goes. Good Luck everyone.

  5. I love the concept for this coaching format and am looking forward to following the progression of both participants. As a foodie, I really resonated with Kathryn. I think that there are a lot of avenues that she can consider when looking for B2B clients.
    -Private Vendors (i.e. Aramark)

    I would also consider selling directly to consumer (i.e. fairs, festivals, etc). It does require more effort, but it gets your product directly in front of the consumer. As she gains raving fans, the businesses will come looking for her.

    Good luck.

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