Over the course of my career I have had the opportunity to structure and manage more than $10 billion in debt and credit facilities. These transactions were not only large in scale, but also complex in design, involving multiple lenders, collateral types, and industries that were themselves evolving in real time. While the dollar amounts often get the headlines, the real lessons come from the strategy, discipline, and teamwork required to pull these deals across the finish line.
In this article I want to share a few of the most important insights I gained from structuring these transactions. My hope is that other executives and finance leaders can apply these principles to strengthen their own capital strategies and avoid some of the pitfalls I have seen firsthand.
Lesson One: Build While You Fly, but Do It with Discipline
In an ideal world, a company would have all reporting and internal controls perfected before raising capital. In reality, especially in fast-moving industries, you often have to secure financing while building the very systems that will support it. At Zillow, for example, we were negotiating with major banks while designing reporting processes from scratch. The pressure forced us to be both innovative and precise. Even though the systems were being created on the fly, the output impressed lenders because it was accurate, consistent, and actionable.
The key takeaway is that you do not always need a fully mature infrastructure before raising capital, but you must deliver credibility quickly. Lenders care about accuracy and reliability more than polish, and if you can provide that in real time, you can unlock capital while scaling the operation in parallel.
Lesson Two: Relationships Matter as Much as Terms
Debt facilities and securitizations are ultimately relationships between a business and its lenders. You can negotiate aggressive terms, but if the relationship is transactional, problems will surface when the market turns or covenants tighten. During my time at Starwood Waypoint Homes, we built credibility with the banks and rating agencies by submitting bulletproof reports and demonstrating operational discipline. As a result, we were able to execute seven bond offerings worth $4.5 billion and expand our credit capacity even as the single-family rental industry was still finding its footing.
The lesson is that relationships are long-term assets. By consistently providing accurate data and demonstrating transparency, you earn flexibility when it matters most.
Lesson Three: Flexibility is More Valuable Than Price
Executives often focus on the headline pricing of debt, but flexibility in terms and covenants often provides greater long-term value. A slightly higher interest rate may be worth it if the structure allows you to pivot when business conditions change. At Builders Capital, we negotiated credit lines that could scale with originations and expand into new geographies. That flexibility was more valuable than shaving a few basis points off the rate, because it allowed the company to grow from $3 billion to $4 billion in annual originations.
When structuring facilities, focus on building a capital base that supports growth strategies and cushions you in downturns. The cheapest capital is not always the smartest capital.
Lesson Four: Technology and Process Drive Efficiency
Large debt platforms are not sustained by spreadsheets alone. Linking financial systems to databases and automating reporting can save millions in operating costs and prevent errors that could jeopardize lender confidence. At Builders Capital I helped connect Excel’s Power Query directly to an Azure database, layered in SQL for extraction, and wrapped it with VBA macros. Reports that once took 16 hours a week dropped to 30 minutes, freeing analysts to focus on higher-value work.
Technology is no longer optional in capital markets operations. Efficient reporting and compliance processes allow teams to focus on strategy rather than chasing data.
Lesson Five: Discipline in De-Leveraging is as Important as Growth
Finally, capital markets are not only about raising money but also about managing through contraction. When Zillow Offers decided to unwind, we successfully de-levered $4.3 billion in debt without tripping a single covenant. That required constant communication with lenders, rigorous attention to detail, and discipline in execution. Managing through a wind-down with credibility intact is just as critical as structuring the initial facilities.
Conclusion
Mastering capital markets is less about the size of the deals and more about the systems, relationships, and discipline that support them. By preparing internally, building trust with lenders, valuing flexibility over price, investing in technology, and staying disciplined through both growth and contraction, companies can unlock capital at scale and use it as a true competitive advantage.
The $10 billion I have helped structure is a reflection of these lessons put into practice. For executives and finance leaders navigating their own capital strategies, the opportunity lies not only in securing the funds but in building the foundation that allows those funds to fuel sustainable growth.
