Our
Story
Where Systems, Stories, and Possibility Converge
​
The story of CultivateLAND doesn’t begin in a design studio.
It begins in a greenhouse, on a family farm in Wisconsin.
​
Before Jake understood the language of cities, he learned the language of growth. He spent his childhood standing beside his father, Jim, a plant-loving, charismatic grower who understood people just as deeply as he understood soil.
In that environment, stewardship wasn’t a philosophy; it was a way of life.
Born from a Plot of Earth
Jake’s earliest “projects” were not drawings but living systems.
A plot of earth became his garden, a place to experiment, observe, and create. He learned how to nurture cycles, amend soil, start seeds, and sell his harvest at the farmers market. He watched how plants responded to care, how customers responded to beauty, and how landscapes hold emotional and social value long before they become “design.”
​
In that greenhouse, Jake discovered that environments shape people, that small decisions ripple across systems, and that the most meaningful creations are born from intention, curiosity, and care.
​
But he also learned something else: systems break down when one part is misaligned. He saw how passion alone could not compensate for gaps in strategy, planning, or organization.
Those lessons became the early seeds of a worldview:
“Great design emerges when authenticity, systems, and human experience resonate with each other.”
From Soil to Systems
At UW–Milwaukee, Jake immersed himself in psychology, sociology, hospitality, and the art of reading people. At UW–Madison, he discovered how landscapes could operate as ecological, cultural, and economic systems at scale. He saw how walkable environments shape health, how small businesses give life to place, and how thoughtful design can anchor community identity.
​
But he also discovered something unsettling:
Much of the built environment is shaped by convenience, habit, or short-term thinking rather than intention.
​
He began studying authors and designers who challenged conventional planning, James Kunstler, Andres Duany, regenerative thinkers, permaculture designers, and saw a world where ecology, economy, human behavior, and design could be integrated.
​
This was the beginning of Jake’s unique lens:
A layered, multidisciplinary, curious, future-forward way of seeing.
Possibilities & Limitations
Early in his career at SWA Group, Jake learned the power of design at scale, urban parks in China, massive community frameworks, systems-thinking master plans, landscapes that shaped millions of lives. He gained technical depth, process efficiency, and a global perspective.
​
But he also felt something tightening around him.
His curiosity, one of his greatest strengths, was being constrained.
His ideas were filtered through politics, hierarchy, and financial priorities.
He wanted to cross-pollinate disciplines, explore new approaches, and design more holistically. But the machine had a rhythm of its own.
​
At Clark Condon, Jake stepped into leadership. He built systems, tools, and strategies. He mentored younger designers. He became a go-to problem solver for complex, iconic projects. His voice mattered more, but his vision still had boundaries.
He started asking bigger questions:
​
- Why do designers repeat outdated patterns?
- Why do firms choose projects that drain creativity and meaning?
- Why is the built environment so often designed for cars and corporations instead of people and health?
- Why are we not measuring what truly matters, connection, happiness, resilience?
- What could development look like if we designed for the future, not the past?
​
These questions required freedom. A new path. A new model.
The Leap & Alignment
Jake founded CultivateLAND during a major life transition, marriage, children, a move to a healthier environment.
It was a moment of alignment: everything in his life pointed toward building something intentional, meaningful, and expansive.
​
He left behind the idea that his value was determined by a firm.
Instead, he chose a path where his value would be measured by:
- The clients he partnered with.
- The communities impacted.
- The quality of questions asked.
- The systems created.
- And the resonance his work generated.
​
CultivateLAND became the place where Jake could explore his full breadth:
​
Agriculture, ecology, psychology, economics, technology, urbanism, and human experience, all integrated into a single practice.
This multidisciplinary curiosity is not a quirk; it is the engine of the firm.
Connection, Curiosity, Possibility
CultivateLAND was founded on a belief that the best design is not invented...
It is aligned.
​
Aligned With:
​
- People’s Needs & Aspirations
- Ecological Intelligence
- Cultural Patterns
- Economic Realities
- Historical Lessons
- Future Opportunities​
​
CultivateLAND exists to push the industry forward, not with ego, but with insight, reflection, and courage.​
The firm designs places that:
​
​ - Challenge clients in healthy, inspiring ways.
- Elevate community well-being.
- Integrate systems so they strengthen one another.
- Measure what most firms ignore.
- Create positive resonance and excitement.
- Leaves people transformed, ready for whatever comes next.​
CultivateLAND is a positive disruptor:
Small in size, expansive in thinking, and unafraid to explore new possibilities.
​
What began as a personal origin has grown into a shared practice. Today, CultivateLAND is a collective of designers who bring their own perspectives, passions, and curiosities to the places we shape and the futures we help cultivate