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Those who implement agile software development and agile project management in a traditional corporate environment may encounter legacy corporate and IT processes that reflect legacy mindsets and cultures. These remnant processes, mindsets, and cultures represent opportunities to improve the systemic value that agile approaches are capable of enabling. For example, in many large corporations the annual budgeting cycle drives a mindset that scope, budget, and schedule must be established up front, often many months before project work begins. Success means delivering on that scope within the budget and schedule commitments. In turn, this mindset of defining business investment opportunities upfront, coupled with a project mentality where work must be completed before the next budgeting cycle begins, drives "big batch" (waterfall-type) project approaches and supporting IT processes. As our IT teams successfully applied agile methods at the project level, we began to address our approach for managing portfolios of projects to increase the amount of value we deliver with our business partners. As we did this, we ran headlong into inherent conflicts between agile and legacy corporate processes and mindsets. We recognized the need to transform those legacy processes and mindsets so that we manage the portfolios of project investments in an agile manner. This paper describes the challenges we faced as we applied agile methods to IT investment funding, change management, and governance; the success and failures we experienced; what we learned; and how we adapted to improve.