Paralegal/Senior Paralegal

Brian Sir passes the torch. After five years of faithful service as board chair, Brian Sir, formerly the Chief Operating Officer at Guggenheim Partners, is transitioning into the role of committee member. Brian has had an immeasurable impact in his role. Throughout these five years, he's guided Hope during seasons of growth as well as those of challenge. He has also been a source of support and friendship to many on staff. Above all, Brian has been one of Hope's most passionate advocates - especially for its students, families, and teachers. His leadership helped further shape Hope as a place deeply committed to inclusion, community service, and opportunity for all. Under Brian's leadership, Hope launched the Trades Pathway with the support of local unions, initiated its annual spring luncheon, forged a beautiful partnership with Special Children's Charities, invested in the celebration of women's sports programs, led the recruitment and engagement of new board members, developed its board governance committees, and expanded its Career Advancement programs. But just as importantly, Brian made it a priority to support and retain great teachers. During his tenure, Hope reached the highest levels of teacher retention in its two decades of existence - a reflection of a culture where teachers feel valued, supported, and committed to the mission. Chicagohopeacademy is profoundly grateful for Brian's vision and unwavering belief in the transformative power of a Hope education. While his role is changing, Chicagohopeacademy know his commitment to Hope does not. Matt Gerdes is a Principal and Managing Director at Freeport Financial Partners LLC, a Chicago-based investment management firm. Matt steps into the role of chair after two years on the board, serving on the finance, investments, and trades committees. He is responsible for structuring and managing middle-market private credit investments for Freeport's funds and is a member of the firm's investment and management committees. Matt graduated with a B.S. in Finance from Northern Illinois University and holds an M.B.A. from the University of Illinois at Urbana-Champaign. He and his wife, Jennifer, reside in Western Springs and have two adult children. In his free time, Matt enjoys spending time with family and friends on Delavan Lake in Wisconsin and coaching youth basketball. "Hope is a special place to me," Matt said. "My first involvement was with the school's EYE program in 2021 as a student mentor. Since then, Hope's students and mission have been sources of inspiration to my entire family. One recent highlight was merging my work community with the Hope community for a day of introducing 40 students to the world of private credit. The students livened up our office and reminded my colleagues and me that our professional experiences are gifts to steward well. I'm very blessed to be a part of this community and couldn't be more excited about Hope's future." In its third decade as an organization, Matt's strategic thinking and dynamic leadership will be an asset as Chicagohopeacademy expand Hope's initiatives.

Guggenheim Investments has closed its Guggenheim Private Debt Fund IV at approximately $8.4 billion of total available capital, exceeding its initial fundraise target and hard cap. The final close marks the firm's largest dedicated private debt vehicle to date. The fund focuses on first lien senior secured loans in sponsor-backed and non-sponsor-backed middle market companies. Guggenheim serves as lead investor on over 90% of PDF IV's invested capital and sole investor on 35%, reflecting its conviction-driven approach. Investors are currently 50% called against commitments. The fund builds on Guggenheim's 20-year track record in private debt, having invested over $33 billion across more than 550 borrowers since 2002. The round was led by Ribbit Capital, with participation from Sequoia and Kleiner Perkins.

Kalamata Capital Group, a provider of financing solutions to small and medium-sized businesses, has closed a $111.87 million securitization through KCG Securitization II, LLC, Series 2026-1. The transaction is backed by a diversified pool of small-business receivables, including merchant cash advances and loans originated through Kalamata's platform. The securitization refinances the company's prior Series 2024-1 transaction. The Class A Notes received an A- rating, an improvement from the BBB rating in the previous securitisation. Proceeds were used primarily to refinance existing debt and support continued funding of eligible receivables. Founded by Steven Mandis, Kalamata provides online financing options of up to $500,000 to small businesses. Guggenheim Securities served as structuring adviser and initial purchaser for the transaction.