Most entrepreneurs start with some version of a plan. For Jason Dayton, co-founder of Minneapolis Cider Company and Trail Magic, that plan was surprisingly straightforward: start a cider company as a college senior, spend about $2,500, and have the product on store shelves by Christmas.
Instead, it took until July. It cost roughly $50,000. And the first production run nearly fell apart before a single can was sold.
That was only the beginning.
What started as a senior project at the University of Minnesota eventually became Minneapolis Cider Company, a Minneapolis taproom and production facility, a nationally distributed THC beverage brand, and a business that has been forced to reinvent itself again and again. Jason’s story is a reminder that entrepreneurship rarely follows the clean trajectory shown in a business plan. Sometimes the businesses that last are simply the ones willing to keep adapting.
Starting a Business Before You Know What You're Doing
The original idea for Minneapolis Cider Company started after Jason and his future business partner, David O’Neill, both studied abroad in the United Kingdom and discovered a much larger cider culture than they were used to seeing in the U.S.
Jason also began making cider with his future father-in-law, who grew up in southwest England and had years of home brewing experience. So when Jason entered an experiential entrepreneurship program at the University of Minnesota, his pitch was simple: start a cider company.
His original presentation even declared that “cider is easy.”
It wasn’t.
The class gave students an opportunity to actually launch businesses rather than simply write plans for them. Jason’s team eventually secured financing, found a distributor, located a production partner, and developed a commercial cider recipe. But turning a five-gallon homebrew recipe into thousands of gallons of commercially produced cider proved to be a much bigger challenge than expected.
When Your First Product Almost Ends the Business
Before their first full production run was packaged, samples were sent back to Minnesota. Instead of tasting the cider first, the team delivered those samples directly to their distributor, the company’s only customer.
Then the phone rang.
The distributor wasn’t happy with the product and didn’t believe it could sell. At that point, most of the cider was still sitting in tanks several states away. Jason immediately booked a flight, traveled to the production facility, worked with the cider maker to rebalance the recipe, and overnighted a new sample back to Minnesota.
The distributor approved it. The product shipped. The company survived.
That moment says a lot about what entrepreneurship actually looks like. The polished businesses we see years later usually have plenty of stories behind them where everything almost went sideways. Minneapolis Cider Company was no exception.
Growing One Batch at a Time
For the next several years, the business operated with very little room for error. Every production run represented a significant percentage of the company’s available cash, so revenue from one batch helped fund the next.
Eventually, the team decided the business needed its own production facility and taproom. They began searching for a location in 2017 and finally opened Minneapolis Cider Company’s Northeast Minneapolis location in May 2019.
They added food. They added pickleball. They continued growing the taproom and production side of the business.
Then, in February 2020, the company recorded its first profitable month.
One month later, COVID-19 shut down much of the hospitality industry.
Once again, the plan changed.
Recognizing an Opportunity Before the Market Exists
One of the company’s biggest transformations came in July 2022, when Minnesota updated its laws to allow certain hemp-derived THC products.
Jason learned about the change over Fourth of July weekend. By July 10, he was sitting down with his business partners telling them they needed to enter the THC beverage market. By July 29, Trail Magic was available for sale.
Nineteen days.
There wasn’t an established THC beverage category in Minnesota yet. Consumer education was limited, regulations were still evolving, and very few companies knew exactly where the market was headed. But that uncertainty also created an opportunity.
Trail Magic became one of the earliest THC beverage brands in Minnesota, entering the market while consumer and media interest were at their highest. Events and early brand-building efforts helped accelerate awareness, eventually turning what began as a Minnesota product into a brand distributed across more than 20 states.
Building a Brand in a Changing Industry
Moving quickly created growth, but it also introduced an entirely new challenge: regulation.
Unlike alcohol, which operates under relatively established federal standards, hemp-derived THC beverages have faced different requirements depending on the state. Something as small as whether a can said “best by” or used an expiration-date abbreviation could create compliance problems in a new market.
As Trail Magic expanded, the team had to navigate challenges like:
- Different labeling requirements from state to state
- Changing THC limits and product rules
- Distributor and retailer education
- Banking, insurance, and credit card processing challenges
- The possibility of major federal regulatory changes
The lesson extends far beyond THC beverages. Growing businesses often reach a point where the systems that worked locally no longer work at scale. More markets can mean more complexity, more partners, more regulations, and more variables outside your control.
Growth doesn’t eliminate problems. It introduces different ones.
Sometimes Your Business Model Has to Change Again
The team also found another creative way to expand.
When they wanted to build a larger national distribution network, Minneapolis Cider wasn’t necessarily the right product to lead that expansion. A cider named after Minneapolis naturally had limitations in markets hundreds of miles away.
That led Jason and his partners to Crispin Cider, an established brand previously owned by Molson Coors. They eventually licensed the brand, giving their company access to relationships and distribution opportunities that could support future growth.
The original strategy was to use Crispin to build distributor relationships and eventually introduce Trail Magic into those same markets. But attitudes around THC beverages changed faster than expected, and many distributors became willing to carry Trail Magic directly.
So the strategy shifted again.
Today, the company continues to adjust as federal regulations surrounding hemp-derived THC remain uncertain. It has introduced alcoholic Trail Magic products, maintained its cider business, and prepared for multiple possible versions of the beverage industry’s future.
That ability to adapt may be the most consistent part of the company’s entire story.
Stop Planning and Start Doing
After more than a decade of entrepreneurship, Jason’s advice to aspiring business owners is simple: take the first step.
Find the minimum viable product. Make the first sale. Prove someone will pay for what you’re building.
Entrepreneurs can spend months choosing software, perfecting websites, tweaking logos, building spreadsheets, and creating systems for customers they don’t have yet. Those things matter, but eventually, you have to do the actual thing.
You have to sell the beer. Or the cider. Or the service. Or whatever idea has been sitting in your head.
You probably won’t have the entire journey mapped out before you begin, and Minneapolis Cider Company certainly didn’t. The business that exists today looks very different from the one Jason imagined as a college senior, but every unexpected turn helped shape what came next.
The Support System Behind the Entrepreneur
One of Jason’s biggest lessons had nothing to do with distribution, manufacturing, or marketing.
If you’re building a business while married or in a relationship, that person becomes part of the entrepreneurial journey whether they’re involved in daily operations or not. Jason credits his wife with providing healthcare, helping with tastings, offering emotional support, and standing beside him through years of uncertainty.
Entrepreneurship can easily become all-consuming, especially when the business is constantly changing. But the people supporting the entrepreneur outside of work often make it possible to keep going.
It’s an important part of the story that doesn’t always make it into the highlight reel.
Tune In and Get Inspired
From a college entrepreneurship project to Minneapolis Cider Company, Trail Magic, national distribution, changing regulations, COVID shutdowns, near-disasters, and more than a decade of reinvention, Jason Dayton’s story is proof that building a successful business rarely means following the original plan.
It means recognizing opportunities, making decisions with incomplete information, learning quickly, and being willing to change when the market changes around you.
Hear the full conversation with Jason Dayton on Behind the Brand and learn what it really takes to keep building when entrepreneurship refuses to go according to plan.
