Caleb Holstein - Co-Founder & CEO of greensquare

In this interview, Caleb Holstein, the Co-Founder & CEO of greensquare, shared about his experience as a 17-year veteran of the coffee industry, from starting in cafes to owning a roastery, and eventually launching greensquare. Caleb shared how a transformative coffee experience and key mentorship shaped his approach to coffee, which reminded me of the importance of mentors and the influence we can have on others during moments that may seem mundane to us.

During our conversation, he explained the value of greensquare, how it functions, and the opportunity it creates not just to optimize operations but to further democratize and change the coffee supply chain.

In light of the early 2025 spike in the coffee futures price, Caleb noted that something we aren’t talking about enough in coffee is our mental health in response to higher prices and the challenges that go along with this. He pointed out that green coffee buyers didn’t suddenly wake up one day and become bad green buyers. This shift is simply the current reality of our industry. While some of it is outside our control, there are things within our control and he emphasized that this season isn’t about winning or losing; it’s about change and that roasters’ pricing strategies shouldn’t be focused on competition, but on survival in our present reality.

Finally, we talked about the skills that transfer from physical jobs like working in cafes and roasting coffee to owning a tech company. He noted that the key is to know yourself and become an excellent communicator — because those skills translate across industries, companies, and roles.