This was my new reality. In just a couple of weeks, I was going rogue. Packing up my belongings into an RV and heading out into the unknown, following nothing but my own instincts, to convince people to drop out of college.

We needed a plan.

We gave ourselves about 3 weeks to prepare. This meant stripping down physical possessions, planning the route, calculating expenses (gas, food), setting up potential income streams, and generally figuring out how to do the tour.

After the excitement from buying the RV simmered down, reality set in. This was no easy task. Ben and I were both kind of in over our heads. But that didn’t stop us. It made it even more exciting.

At this point, it was difficult to articulate our goal to people. It felt right, but definitely could have used some time to mature.

We wanted to change the way people thought about education. We wanted to get college kids to understand what college was in reality, and to shake them out of their hypnosis of thinking college was some sort of golden ticket that made it OK to continue being passive and not enter the harsh real world that requires real effort.

We had tons of different ideas on how to convey this message, but could only try one at a time. So we recruited our friend Jason, the DJ, and devised a plan to set up pop-up concerts on or around college campuses. We would draw people in with music and engage with them on a human level, sharing our vision for education and being real with them about college.

Here was our plan:

We would issue Dropout Degrees for free. The Dropout Degree was a pamphlet that briefly outlined what’s wrong with college and what a real-world, self-education alternative might look like. It was our way of poking fun at the unimportance of a college degree. This pamphlet would drive people to our website and social media.

We would then upsell “The Bundle.”

The Bundle was a package for $25 that included my book and a T-Shirt.

We toyed with the idea of creating Xplor shirts and swag, but realized nobody would recognize our logo yet. So we decided to go with something everyone would recognize:




I mentioned this in passing to my friend, Claire, a dropout who appeared on my podcast, and she connected me to a local printing company, Outfit Good. I put in an order for 100 shirts.

If people didn’t buy The Bundle in person but they were interested in following our journey, we’d drive them to our social media profiles, all of which funneled to our website, which had a lead capture and a value-offering.

We set up our systems with one tangible goal in mind:

Capture the information of people who were intrigued enough to follow our journey.

This was a start, because it would give us an opportunity to interact with them, and eventually figure out how to offer solutions to their problems.

We spent about $800 on t shirts and were selling them for $15 (in the bundle) or $20 alone. We planned on visiting 14 colleges, so we needed to sell just 4 shirts at $15 a piece at each school in order to break even.

I ordered $400 worth of books and sold them at $10 each (bundle or not), so breaking even would require 3 book sales at each school.

So 4 bundles per school would make us profitable on the materials. This didn’t include gas or food, so we set our goal for 8 to make up the difference.

This couldn’t be that hard, right?

The goal really wasn’t to make money. It was a growth experience from the beginning. We realized it was likely that we would lose money on this venture. It was well worth it.

Next was planning the route. A lot of thought went into this. There were a few key variables:

  1. Targeting colleges with the highest dropout rates – makes sense, right?
  2. Gas efficiency. Driving a 16,000 lb house-with-wheels across the country at 6 miles per gallon isn’t cheap.
  3. Timing. We had 2 months to hit as many schools as possible before finals ended in May.

As mentioned in Part 1, I wanted to visit Austin, Texas. I heard it was a cool place, and since I was breaking all my self-imposed shackles, I had the freedom to go anywhere – why not somewhere warm?

So we began planning the route with Texas in mind as the first stop. Initially, we wanted to go to the southern states (Mississippi, Louisiana, Georgia) and loop back around to the midwest. The route changed about 7 times during this process.

Here’s the final version of the table I used to track those key variables:




Planning the route was draining.

This is where I hit my first internal roadblock.

At the very beginning, this tour was born out of pure passion, freedom, and excitement. Planning the execution of the tour meant putting some structure to it. This was initially a struggle, but that struggle reminded me that pure sunshine and rainbows only exists in your head. If you want your ideas to change the world, in reality, you must bring them to reality. Structure exists for this reason, and to avoid it is to defeat the purpose behind your ideas in the first place.

Our departure was looming. I was excited, nervous, freaked out, and didn’t know what would happen. Doubt crept in often. I felt alone. Most days I questioned my own sanity.

Then, out of the blue, the day before we left, I got an email from the owner of that T-Shirt company, Andrew (who also recently came on the podcast). It read:

Subject: Man, fuck college.


Hi Simon,


We haven’t had the chance to chat yet, but I wanted to reach out and first thank you for giving us the chance to print the shirts for the Xplor tour. I think what you are doing is awesome, and I only wish that I had met someone like you years ago. My college story happens to be exactly what you are trying to stop.


Nobody in my family had ever gone to college before, so I thought that I needed to go in order to prove something. It turns out that seven years and thousands of dollars of student loan debt later, I actually run a relatively successful business with a great partner, and I in no way use any of my formal education in doing so. I use to think that not going to college would be a huge mistake, and it turns out that actually going to college was an even bigger mistake. It’s such a joke. The educational system has failed countless students, and continues to do so to this day.


Hopefully you will be able to positively influence some students to rethink their path, and know that going to college, getting a shit job for some corporation that doesn’t care about them, and then retiring isn’t how life has to be. That’s what was pounded into my head, so when I got my bullshit corporate job, I thought I would be set for life. Turns out luxury cars don’t sell during a recession and I got laid off, and the company didn’t even flinch in doing so. I recently saw a quote from an entrepreneur, but I can’t remember who it was. It said, “being under someone else’s employ is hazardous to my financial well being”. And I couldn’t agree more.


I got on the Xplor site and saw that you will be in town in April. I would love the chance to sit down and chat with you if you had some free time. We wanted to check out your book so we got a copy off of Amazon. I’ll be sure to pass it on to someone in the future who is considering college their only path.


Take care my friend. And thank you for all that you are doing for students like me. They will appreciate it down the road.



In all the chaos and uncertainty, moments like this are what kept me going. That day, Andrew reminded me of my why. He reminded me that I wasn’t the only one who felt disenfranchised by this whole behemoth of an education system. He reminded me that I was a spokesman of this movement; I was a leader; I had a firm purpose.

Emails like this would happen more and more along our journey.

Ben and Jason got to my Columbus apartment at about 4 in the morning on the day of our departure. I remember this because they were running a few hours late prepping everything, so I unexpectedly fell asleep. I abruptly awoke to someone standing on top of an RV, knocking on my second-story window.

We packed my things, buckled up, and headed south.



This is Part 2 of a series I’m doing on my experience touring the country in an RV trying to convince people to drop out of college.

Part 1 | Part 3