We were lucky to catch up with Michael Kivland recently and have shared our conversation below.
Michael, appreciate you joining us today. Risking taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.
Starting this business was the biggest risk I have taken. I was working as a salesman for 12 years. In those 12 years, I had a lot of success – I made good money, but it didn’t matter to my psyche. I wasn’t happy.
The role I was in for 12 years was toxic. The people I worked with were toxic. It was ripe with every toxic workplace element you could dream up. A CEO born out of nepotism, backstabbing employees, lies from upper management, unqualified promotions, etc. You name it the ailment and it had it. My psychology degree was telling me that I had to leave for my mental health. I was stressed, tired, and worn down. It was time to break the chain.
I decided to quit over the 4th of July while away on vacation. I went to a local farmers market in upstate Wisconsin and was inspired by the stories of the local vendors. Stories of how they started, how their business is doing, their happiness, and how they broke the chain. After hearing those stories I knew what I had to do.
I packed my bike in the trunk and rode my company car to work on July 11th, 2022. I walked into my boss’s office and told him I was done. I quit. They asked for two weeks. I told them they had ten minutes. His face was red. My face was joyous. I said hurried goodbyes to some homies I had in the office and shop. Ten minutes after arriving I was biking home. Free and unchained. Unburdened by their toxicity.
Two days after quitting I started Heady Cup with my business partner, Kevin. He had the ball rolling on getting the company started. It has been nonstop since. We are growing. I am happy. I am proud I took the risk. It is the most rewarding thing I have done professionally.


Michael, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
Heady Cup is a small-batch specialty coffee roaster located outside of Chicago. We specialize in custom blends and exclusive single-origin coffees. Our mission statement is focused on three core tenets. Traceability of our beans to a specific farm or farming cooperative, social responsibility in our local and coffee-growing communities, and sustainability throughout our entire sourcing and production process. These are not talking points! Some examples of these tents put into practice include, recycling our used coffee bags, planting a tree in a coffee-growing region for every bag we sell, and working with importers who invest in the communities in which our coffee is grown.
I entered this business as a coffee lover and a self-described “foodie nerd.” I have always been attracted to rare and hard-to-get. Sourcing exclusive coffees that tell a story was a natural transition for me. I am a climate change lobbyist for my political district. The words we talk are the words we walk.
Kevin, my partner, is a master data-driven roaster. His ability to draw out rare and unique flavor profiles from raw green coffee beans are what truly sets us apart as a roaster. He is constantly working on his craft. 10,000 hours of mastery become 20,000 hours of perfection. Logs and logs of roast notes and profiles line his desk. All our tracked on his computer but he hands writes them as well. His diligence and drive to be a great roaster pervade our entire process. We are chasing craft perfection. Kevin reminds us of that which each one of his roasts. The pride we have in our coffee beans is a result of our constant pursuit of perfection.
In my current role, I get to use my creative skillset without being handcuffed which has been invigorating. Colorful bag design, whimsical social media marketing, and all of our branding are good examples of how we use creative manifestations to market Heady Cup.


What’s been the most effective strategy for growing your clientele?
The most effective strategy for growing our clientele has been direct customer interaction. We do a lot of local community events including farmers markets, craft fairs, coffee cart events, charity events, etc. Speaking directly to the consumer and telling our story has been the single most effective thing we do. We pride ourselves on our fast, dependable customer service, which has certainly been a factor in our growth, but building a personal connection to our clientele has been the biggest boon to our success. The community knows us and our values. They know our product is high quality. Our customers know we will do all we can to help solve any problems they have. There is no magic formula to growth but all those factors have combined to help us make inroads with and gain the trust of our community of customers.


Are there any books, videos or other content that you feel have meaningfully impacted your thinking?
I can’t say there was one singular book, essay, or video that significantly impacted our entrepreneurial thinking. There were several that pervaded our entrepreneurial psyche. “Swim towards the shark.” “All gas no brakes.” “You don’t climb the mountain – you are the mountain.” All of those sayings are a good indication of what motivates me. Not a book or video, but one saying that has impacted my business philosophy the most is the quote, “Stagnant water rusts pipe.” We can’t lose our innovative spirit. We have to keep our ideas and approach fresh. If we stagnate we die. Simple. We are constantly looking for ways to improve our processes. We do not rest on our laurels. If we think there is a way to roast better coffee we will pursue it. If an innovative new brew technique enters the marketplace we will work to master it. Specialty coffee is an ever-changing beast that we have to sharpen our skills to be able to slay. Swim towards the shark.
Contact Info:
- Website: https://www.headycup.com
- Instagram: @headycupcofferoasters
- Facebook: @headycupcoffeeroasters
- Linkedin: Michael Kivland
- Youtube: @headycupcoffeeroasters


Image Credits
None to provide

