New Farmer Profile & Profile of Farmland Investor with Partnership Vision

Peyton Cypress - FarmerPeyton Cypress

One of the first things Peyton Cypress expressed to us during a recent advising Zoom call was, “I am ready to lead something on my own!” We quickly learned that not only is he eager to lead his own farming enterprise, but he is really ready to do that once he finds the land he needs.  

Peyton, a native of Flosmoor, took an interest in food at a young age. Close neighbors and friends owned a restaurant, prompting him to be more aware of where his food came from. He came to realize, too, that all food has a story to tell.  

That consciousness and curiosity continued into his adult years and eventually launched him into a journey of farming experiences spanning states and even countries.

He began in Milwaukee in 2016 and then moved onto Canada, New York, Nashville, and finally the island off of Washington where he currently resides. Each stage offered new farming experiences and even many management roles. He was fortunate enough to apprentice under leaders in the organic farming movement, such as Jean-Martin Fortier who authored The Market Gardener, and Jack Algiere of the Stone Barns Center for Food & Agriculture in New York. As a result, he not only knows vegetable and herb production, animal husbandry, and seed saving but also bookkeeping, financial tracking, and systematic farm enterprise planning. Along the way, he picked up a passion for weaving education into his farm activities as well.

Peyton is wrapping up his current role teaching beginning farmers at the Organic Farm School in Clinton, Washington. His goal is to find farmland south or southwest of Chicago to begin his own farm operation where his roots always were as soon as next growing season. Peyton is open to a variety of opportunities that come his way, but his ideal would be to find between 25-100 acres, roughly split 50/50 between forest and pasture, with a fresh water source. His preference is to purchase if the right land presents itself, but he is also open to leasing or partnering.

“I see tremendous opportunities in northern Illinois to produce local sustainable food and demonstrate farming practices that are healthy for land and people,” says Peyton.

If you have any leads or connections for Peyton, please contact Jim at and we will get you connected with him.

Farmland photoBill Rempe - Farmland Investor

Bill spent his career observing Americas quilted blocks of green, yellow, and brown farmland from 40,000 feet. Now retired from the airline industry, he is feeling drawn to something on the ground. He wants to be up close and personal with soil, plants, and animals. But, and here’s what surprised us when he contacted us, he doesn’t want to be a farmer and doesn’t already own farm land. 

His vision? Investing his retirement savings in a rural home (or homes?) with enough land for a small-scale farm operation. He would live on the property. Someone else would lease the farmland from him and do the farming! Bill envisions his role as being a “silent partner” who would live there but would not interfere in the farmer’s life and work. This, arrangement, he hopes, would offer a beginning farmer the chance to lease farmland on affordable terms to live out their own farming ambitions. 

Bill came to this off-the-beaten-track vision of retirement about seven years ago. A longtime organic farming supporter, Bill was reading some resources from MOSES (Midwest Organic & Sustainable Education Service), and something clicked. He wanted to be on a farm. Bill shared:

“I believe we are to be good stewards of all we have been blessed with. Nothing is ours ‘forever.’ We all die as we came into the earth...with no possessions! My ultimate desire is to leave whatever I have in the hands of like-minded people who will ‘carry on’ with my vision of leaving the earth a better place for future generations.”

Soon after that dream began, however, a significant health incident set Bill back. Taking active steps towards his vision had to be put on hold for a number of years. Then his health improved and a recent postcard from MOSES in the mail reignited his energies for pursuing his ideas.  

In regard to what kind of food the farmer produces, Bill is flexible. “As long as it’s organic,” he says. For location, he’s focusing on northern Illinois at the moment, but he is open to a broader swath of Illinois or the Midwest.

Bill believes he’d be looking for a property in the range of $450,000 or less. There are obviously some details and terms that would need to be discussed and agreed upon in advance of a committed partnership.  

We see potential in Bill’s vison for a creative, mutually beneficial land access arrangement. A beginning farmer gains access to secure tenure that might otherwise not be possible. Bill enjoys his retirement in a meaningful way close to the land while leaving a legacy.

Would you help us make that connection? If you have farmland that you believe Bill might be interested in or are a farmer interested in learning more about this opportunity, we’d encourage you to reply to this email and let us know. We’d be happy to connect you with him.