Introduction

I graduated with a BA from University of Vermont (UVM) in December 2010. Going to law school seemed like the logical next step studying Political Science and Economics, but I hadn’t really given it too much thought. I really loved the Burlington area, but there wasn’t a law school nearby. If UVM had one, I probably would have went there regardless of how bad the job market for new lawyers was.

But alas, Burlington had no law school and the job market for new lawyers was bad. I set up a meeting to discuss my potential next steps with my pre-law advisor, one of my former professors. She sent me a news article, it might have been this one from the Washington Post: “How law school went from being a sure thing to a bum deal”. Here’s a quote:

The job market for lawyers is terrible - and that hits young lawyers the worst. Although the National Association for Law Placement, an industry nonprofit group, reports that employment for the class of 2009 was 88.3 percent, about a quarter of those jobs were temporary, without the salaries needed by most new lawyers to pay off crushing debts. Another 10 percent were part-time.

It didn’t take much convincing. After reading the article and a short visit with my advisor, law school was out. I had signed up for the LSATs, but I never took them.

My goal instead became finding full-time employment around Burlington. I had this idea there would be some sort of “office job” that required a bachelor’s degree where I could learn the business and eventually move up. I was looking for entry-level position with a career path. Doing something even remotely entrepreneurial had not crossed my mind.

Did I find anything? The short answer is no, I did not.

After several months, and well over a hundred applications - many of which I spent writing custom cover letters, providing references, and tailoring my resume - I still had no full-time job. I also tried unpaid internships and even a liquor store management position to no avail.

Time Wasters

I did land a Data Entry position with the State of Vermont. Unlikely to be a career starter, but hey, I could almost pay my rent now. The day I was slated to start I received a voicemail while I was in the shower. The position had been eliminated, an hour before it started.

I also interviewed for a position at a national brand inside the e-commerce department. It was entry level, and pretty vague as to what the role’s actual responsibilities were. But I figured it had a career path. National brand, e-commerce, right? I could get in there and help them anyway I could. But I never heard back after the interview so eventually I reached out. It turns out they all really liked me but decided that they were not going to hire anyone at all.

I learned that even in the civility of the so-called professional world, people don’t seem to see any problem with completely wasting your time. Especially as a job seeker in a bad market. Especially that.

57% of people who go to college in Vermont leave the state after graduation - which is higher than any other state. One reason as far as I can tell is there’s not much in the way of entry-level jobs. Or jobs at all, for that matter. I really wanted to be here however, so I had to figure something out.

Vermont Baseball Tours

The idea for Vermont Baseball Tours came about when I was working as a doorman at a bar in downtown Burlington by the name of The Other Place (The OP). The OP is/was sort of a dive-y hippie sports bar.

With Red Sox pitching legend Bill Lee at The Other Place

It was the Spring of 2011, and the Red Sox season was approaching. The team had made waves in signing Carl Crawford as well as extending Adrian Gonzalez. They would bring back David Ortiz as well. Everyone was excited.

In my conversations with people at the bar I did find a common thread. They all wanted to go to see the Red Sox, but there were things holding them back. The reasons were:

1. The travel was a huge hassle. Burlington, VT is about a four hour drive from Fenway Park. While a same day trip is feasible, it’s at least 8 hours of driving round-trip (sometimes through significant traffic), and solving the problem of parking is tough (and/or expensive).

2. Fnding tickets for an okay price was impossible. The Red Sox were still in the midst of their record decade-long (2003-2013) home sellout streak which lasted 820 consecutive games. Most people were in the hands of scalpers.

I figured I could solve these problems. I could:

• Charter a bus
• Buy tickets through group ticketing
• Put together a goodie bag
• Provide some on-board entertainment.

I would sell it all as a good package deal - saving people some money and the hassle of the experience.

I recruited my best friend growing up (who I went to many Red Sox games with over the years) to join on. Vermont Baseball Tours was born. It was “the fun, affordable, and hassle-free way to get to the game”.

Vermont Day at Fenway Park

My grandmother was going to give me some money for graduating college. I explained my plan of running a baseball trip and ended up driving up to Canada to give her this presentation:

She gave me the money to buy 53 Red Sox tickets to Vermont Day (May 1st, 2011) all in Right Field Grandstand 4. $30 each for a total of $1590.

53 tickets to Vermont Day at Fenway Park

One note: The presentation above claims a baseball tour service to Fenway Park does not exist in the region. That was untrue, although I did not know it at the time. I did research online, but never found Milne Travel. I believe they ran bus trips to every home game, or at least many. In the years we operated I never really had any direct communication with them. I have always wanted to thank them for having bad SEO because if I found them I may have never started the company.

Anyway, the bus I chartered also could fit about 50 people, so this lined up nicely with the amount of tickets I had.

Next up was finding people to join us on the trip. From looking at the Guest List, it appears I had 11 people from the bar going to Vermont Day. I would need to sign up at least 30+ others.

Digital Marketing

So, how did I find those people? The short of it is digital marketing - the web and social media. Facebook ads especially, and even Craigslist. Later, over time as a business, we built a strong email list with a notable amount of repeat customers. While we did spend time and money putting up flyers, advertising on the radio and in print, much of that was expensive, time-consuming, and far less effective.

Our advantage would always be that we were pretty good digitally - a decent website, social media presence, and we took payments online. What we did as a service was clear. Our value proposition was pretty obvious - it was right in the name of the business. Over the course of a couple months, we booked a lot more seats on the bus and ended up with 46 guests for Vermont Day.

While having it together digitally really helped, I still had to persuade many people on joining the trips, usually over the phone or by emails. I learned how to sell a little bit, and perhaps most importantly, how to qualify leads.

To qualify a lead is to evaluate a potential customer to determine their suitability and readiness to become actual customers. This adds to my point about people wasting your time. There are people out there who will waste your time. Hours of back-and-forth, odd requests, off-topic monologues, total buyer’s remorse, out-of-the-blue refund demands, you name it. The most difficult people are often the ones who don’t spend any money at all. This is true in business but it applies to all relationships. Qualify your leads.

The Trip

The trip went well, especially for not knowing anything about running one. The “game day” operations and “trip leadership” aspect of the business would never be our strong suit. But Vermont Day overall was a sucesss. The Red Sox won that game on a walk-off. We even lucked out and met Governor Shumlin at a rest stop as he was on his way to the game. One guest on our trip told me they paid less for the whole package than they would have for just a ticket to the game.

Governor Shumlin with Vermont Baseball Tours

Financially, the trip was also pretty good, with a profit margin of over 20% which as high as we ever achieved on any trip we ran for first year. Ultimately, buying tickets directly from the source (the Red Sox etc.) was a major key to success but we were extremely limited by the capital we had to spend up front.

At Yankee Stadium with trip guests

Vermont Baseball Tours ran several more trips in 2011. We ran trips on back to back weekends in the Fall. The high watermark for the year was a same day trip to Yankee Stadium for Red Sox versus Yankees. Exhausting for everyone, but overall as an experience it was awesome.

Just Enjoy!

After baseball was over, hockey season was approaching and we decided to branch out with a service called Vermont Hockey Night. We made a logo, built webpages, did promotions, etc. All the things we were sort of good at. Long story short though, it was a total bust. Barely anyone signed up. There wasn’t enough demand, and from that we decided to broaden our scope.

“From the guys who brought you Vermont Baseball Tours”… okay 😂

Side note: That “UVM Weekend Tour” flyer got me a call from somebody who ran trips from the University of Vermont. They claimed we couldn’t use any logos or photos. It felt like a nice way of saying they didn’t appreciate us impeding on their turf.

Just Enjoy! was born to allow us to take the “fun, affordable, hassle-free” service to any outing, and any geographical location. We didn’t feel like we could run even 20 trips from Vermont alone per year, there simply was not a bigger enough market for it. If we could double our margin and run 10x the trips, I figured we could make a living with the business. We also started to plan group outings for organizations which would become the main focus in later years.

We ran our first trips out of Boston including a multi-day Bruins in New York package.

Just Enjoy at Nassau Coliseum

The business was growing organically. We ran more trips in 2012 than in 2011. We nearly doubled our revenue and improved our margin 4x. Digitally, we were going from good to even better. I worked full-time as a Webmaster at a small SaaS company which further developed my skills. I began learning web application development in earnest.

At the same time, the business didn’t pay us. Sometimes, I felt like I had created my own dream unpaid internship. Except I was an unpaid internship who was responsible for everything. I did work to raise money for the business. Banks all said no. No local business people were ultimately interested in getting involved either. This would cause a lot of stress over things that seem ridiculous in hindsight. We fought over $20 of spending. I would have to max out a credit card with a $300 limit.

A SaaS Model

The further I went into web application development, the more it seemed obvious to make a software-as-a-service platform - something web-based that combined online social sharing and bus-based event travel.

Here’s the pitch deck from 2012:

Venture Capital?

As we began to work on a SaaS model for Just Enjoy, I received an introduction to a prominent venture capitalist in Vermont. I soon had an in-person meeting. I discussed our background running bus trips and how we were potentially pivoting to a digital platform, a sort of “Uber for bus travel”. I followed up after the meeting via email but never heard back.

A few months later, someone reached out to me to see if I was involved in a group travel startup this same venture capitalist was incubating. I was not. Just Enjoy was not. This startup would go on to raise at least $11 million before abruptly shutting down. According to the CEO, it was “one of the six products” they would release. I guess that didn’t happen, since they failed at the first one.

Do I have anything positive to say about that? No, I don’t.

Maybe the VC just wanted a founder that went to Middlebury? I don’t know.

Like all good entrepreneurs, Snake went to Middlebury

Do I think we could have done a better job executing our vision with help from investors? Yes, I do.

Perhaps we were a bit too rooted in mundane reality for VCs, given our background as a service that simply helped make it easy for Vermonters to get to baseball games.

In The End

By late 2012, I was knee deep in web development. It was web development all day, every day. My partner then received an opportunity to start a new office for her company down in Boston. I applied to some positions down there and lucked out, landing my first full-time web development gig. After we moved, Just Enjoy never ran any more trips from Vermont. I would leave the business in 2013. My co-founder would go on to run it successfully for several years, focusing on group events.

As I eluded to earlier, I never “made a living” off the business. I never earned any money from it directly at all. However, it was a springboard for my career, in a way that no random entry-level job would have been.

In The Dark Knight, the Joker says, “If you’re good at something, never do it for free.” This is true, but I would add that when you’re not actually that good at something, you should do it for free. It really worked for me. The personal and professional growth I had was exponential. I was able to positively affect people’s lives.

One fascinating truth about my career is my income has never correlated with my impact. You might even argue it is negatively correlated. Just Enjoy had amongst the most impact, yet I made nothing. Later in my career, my highest paying job was working on a product offering that never even launched (and the group no longer exists within the organization), effectively putting its impact at zero.

The thing I am most proud of is providing a service that enabled once-in-a-lifetime experiences for people. Making it affordable and accessible to go to an event in a place someone has always wanted to go.

As I mentioned, we were pretty good at the digital side of things. Web development became my career. Those experiences made things easier for people, but they were not the end-all-be-all. Automation can make things dramatically more efficient, but I think the world has made it too much of a focus. In the end, I am much more proud of what we accomplished with Vermont Baseball Tours than I am of coming up with an “Uber for buses”.