This episode of Inside the Win showcases how a technology advisor transformed a small initial opportunity with a large legal firm into a major ongoing partnership. Starting with nine months of relationship building and educational conversations about the value of indirect channels versus direct purchasing, the team finally received their first opportunity - a modest $140 monthly cable circuit. After executing this flawlessly, they identified the client's broader challenges around shadow IT, contract management, and technology spend visibility across 100+ locations. By introducing solutions like technology expense management platforms and network aggregation services, they helped the client gain control over their chaotic IT environment, discovering over 3,000 unauthorized applications. The relationship has now grown to over $200,000 in monthly recurring revenue, with the client directing all IT purchases through the advisor. The key lesson emphasizes the difference between persistence and pestering, showing how patient relationship building and focus on business outcomes rather than just selling products can lead to transformational partnerships.