Most of what I know was learned inside audacious work.
From the beginning of my career, I have been drawn to the strategic questions inside organizations trying to accomplish something difficult. Strategy became real to me through store layouts, inventory systems, startup launches, investment decisions, operating models, and leadership transitions. But after all, as the saying goes culture eats strategy for breakfast, and I quickly realized the truth of that in working with highly capable and passionate people who struggled to achieve the audacious goals they had set out to accomplish.
My first roles in Costa Rica put me close to operating leaders and immediate business results. At Corporación Musmanni, one of the country's largest bakery and convenience-store chains, I was brought in to help rethink how struggling non-franchised stores used their limited floor space; one redesign I proposed based on analysis of customer behavior increased sales by as much as 80 percent. At Casa Blanca, then one of Costa Rica's largest retailers, I led the design and relocation of a central distribution center intended to resolve persistent inventory problems. I learned to move between the larger strategic picture and the operational detail, and to respect how quickly an elegant idea meets real constraints once other people must carry it. As they say: plans are useless—but planning is priceless.
I then co-founded EEZR Dental, a bootstrapped dental-tourism startup. It taught me product development, go-to-market strategy, marketing and positioning from the founder's side, including the uncertainty and the distance between a compelling idea and execution. A potential investor later invited me to join ÍCARO, an angel investment firm, where I developed strategic executive plans and analyzed investments between $200,000 and $1 million in early-stage companies ranging from geolocated advertising to engineered biotechnology. I came to know both sides of the table: the founder asking others to believe in a possibility and the analyst responsible for deciding whether the evidence justified that belief.
At One Earth Future, an international privately endowed foundation that incubated innovative peacebuilding programs, I spent seven years helping the organization develop, test, and improve ambitious approaches to global peacebuilding and economic development. I joined its Future Labs team tasked with redesigning the organization's program development process. What I designed eventually became the strategic framework for the foundation as a whole.
Over time I moved to lead strategy of the foundation itself, working with teams to sharpen their purpose and value proposition, served as a close strategic partner and de facto chief of staff through a leadership transition, and eventually led the department charged with key performance indicator management, learning and accountability. I built frameworks for articulating strategy and measuring success, generated information leaders could use to make decisions, and designed sensemaking and planning sessions that helped teams learn and adjust. The work ranged from foundation-wide strategy and operating systems to workshops with teams pursuing work ranging from ex-combatant reincorporation and rural economic development in Colombia to small and medium business loans in Somalia to open-source nuclear de-escalation based out of Vienna.
Those years were not clean case studies. I saw thoughtful strategies fail when people carried different pictures of the problem. I saw measurement become reporting theater when it was disconnected from real decisions. I had hard conversations, pushed new approaches through doubt, revised them when the evidence required it, and learned how much organizational change depends on trust, language, and the quality of the relationships carrying it.
I later returned to the operating side as a partner in Everland Properties, an owner-financed rural-land business, before choosing to exit and pursue other ventures. Today I continue to hold responsibility inside organizations with audacious missions. At the Society for the Way of Knowledge, I began with a diagnostic of the organization's challenges and opportunities, built a plan for addressing them, and helped carry a broad organizational revamp into practice. As a co-founder and operating leader at the Human Institute, I am helping turn an ambitious vision into a more coherent and durable organization. I co-founded the Colorado Connection Collective to offer trainings and events on circling and authentic relating in ways that equip people to see each other and be seen in deeper and more meaningful ways.
I have now sat in many seats: founder, partner, project manager, department leader, investment analyst, facilitator, operator, and advisor to the person ultimately responsible. I know the experience of being the leader receiving advice and of being the advisor whose job is to challenge a leader without taking their authority away. I have made good calls and bad ones, launched things, ended things, watched others make mistakes, and learned from my own. I am still learning. What I bring was earned close to the consequences: an ability to see the whole, ask the question that matters, name what is being avoided, and help an ambitious goal take form in decisions, relationships, and work people can actually carry.