You Probably Won’t Find What You’re Looking For

When I graduated from UVM in 2010, I wanted nothing to do with entrepreneurship. I wanted a normal job. An office, a career path, maybe a 401(k). I sent out well over a hundred applications in the Burlington area. Custom cover letters, tailored resumes, the whole routine. I landed almost nothing. One job was eliminated an hour before I was supposed to start. Another company decided after interviewing me that they just wouldn’t hire anyone at all. min If you’re graduating right now, or in the middle of a career shift, and the job market feels like it’s actively working against you - I believe you. It might actually be. That doesn’t mean you’re doing something wrong.

What it might mean is that the thing you’re looking for doesn’t exist yet, and you might have to build it.

You Don’t Need a Big Idea

I started Vermont Baseball Tours because of conversations I had while working as a doorman at a bar. People wanted to go see the Red Sox but the drive was brutal and tickets were impossible to get. That was it. That was the entire insight.

I didn’t have a business plan. I had a PowerPoint I showed my grandmother so she’d give me $1,590 for tickets. There was no market research beyond talking to people at a bar. There was no “disruption” or “platform play.” I chartered a bus, bought group tickets, and put together a decent package deal.

The best business ideas are often just solutions to problems you can see right in front of you. You don’t need to reinvent anything. You need to pay attention to what people around you are struggling with and then actually do something about it.

Do It Badly, But Do It

Our “game day operations” were never our strong suit. We were not seasoned tour operators. We were two guys in our twenties who figured it out as we went. The first trip had a profit margin over 20%, which sounds great until you realize the actual dollar amount was modest. The business didn’t pay us anything for years. I once maxed out a credit card with a $300 limit for the business.

None of that mattered. What mattered is that we did it. We ran the trips. People had great experiences. We met the governor at a rest stop. A guest told me they paid less for our whole package than they would have for just a ticket.

If you’re waiting until you feel ready, you’ll never start. You will never feel ready. Do it badly. You’ll get better, and the experience of doing the thing is worth more than any amount of preparation.

Learn the Thing That Lets You Do the Thing

When we started Vermont Baseball Tours, I knew very little about web development. But I knew we needed a website, we needed to take payments online, and we needed to reach people through social media and search. So I learned.

That digital competence became our biggest competitive advantage. Our main competitor had been running trips for years but had terrible SEO - I never even found them when I was researching the market. We were better online, and that’s what allowed two guys with no money and no connections to build a real customer base.

The skills I developed doing digital marketing and web development for a business that never paid me became my actual career. I went from doorman to Webmaster to full-time software developer. The business was a springboard in a way that no entry-level job would have been.

Whatever you end up doing, identify the skill that makes it work and get serious about learning it. Not in a classroom. By using it for something real, with actual stakes.

Qualify Your Leads (In Business and In Life)

One of the most useful things I learned running the business was how to qualify leads - evaluating whether a potential customer is actually going to buy, or whether they’re going to waste hours of your time with odd requests, endless back-and-forth, and then never spend a dollar.

The most difficult people were often the ones who didn’t spend any money at all.

This applies everywhere. In your career, in relationships, in how you spend your time. Learn to recognize who and what is worth your energy. Not everyone who engages with you is a real opportunity. Some people and situations will burn your time and give nothing back. The sooner you develop instincts for this, the better.

Nobody Is Coming to Save You

I had a meeting with a prominent venture capitalist in Vermont. I explained our vision, our background running trips, our ideas for a digital platform. I followed up. Never heard back. A few months later, I found out this same VC was incubating a nearly identical startup with a different founder. That startup raised $11 million and then shut down.

Banks said no to us. Local business people said no. No one was interested in helping financially.

Here’s the thing: that was fine. We didn’t need them. We ran the business ourselves with almost no capital. It was harder, sure. We fought over $20 of spending. But we owned it completely and we actually shipped something that worked.

If you’re waiting for permission, investment, or a mentor - stop waiting. Start with what you have, even if what you have is a grandmother who believes in you and $1,590.

Impact and Income Are Not the Same Thing

One fascinating truth about my career is that my income never matched my real-world impact. Just Enjoy was actually impactful - enabling once-in-a-lifetime experiences for people, making events accessible and affordable - yet I pretty much made nothing from it. Much later in my career, my highest-paying job was working on a product that never even launched. It had a total of 0 users.

This isn’t a reason to work for free forever. But it is a reason to not let a paycheck be the only measure of whether something is worthwhile. Especially early on. The work that shapes you the most rarely pays the best.

The Reluctant Part

I never wanted to be an entrepreneur. I wanted someone to give me a job. When that didn’t happen, I made my own thing out of necessity, not ambition. And honestly, I think that’s how a lot of the best small businesses start. Not from some grand vision, but from someone who needed to figure something out and just did.

If you’re graduating or shifting careers and feel like nothing is working, consider that the thing you’re supposed to do might not have a job listing. It might be something you notice while talking to people. Something small and obvious that you could actually pull off with the resources you have right now.

You don’t have to be a “startup person.” You don’t need a pitch deck or a VC meeting. You just need a problem worth solving and the willingness to start before you’re ready.