CastleOak Securities Research
Advisory Approach
CastleOak Securities is a minority-owned boutique investment bank with a distinct focus on capital markets, sales & trading, and financial advisory services. Unlike traditional lower middle market M&A advisors, CastleOak's primary business is centered on debt and equity capital markets—helping corporations, government agencies, and institutional clients raise capital through public offerings, bond issuances, and structured finance transactions. The firm has assisted clients in raising over $5 trillion in securities since its founding in 2006.
The firm's Investment Banking & Capital Markets practice combines transaction experience from bulge-bracket Wall Street firms with boutique-level senior attention. CastleOak operates with a thesis that differentiated distribution—particularly to minority-owned, women-owned, and emerging investment managers—provides issuers with unique access to long-term holders who are often overlooked by larger firms.
While CastleOak has an established M&A practice and provides strategic alternatives advisory, it is not a traditional sell-side M&A advisor for lower middle market companies. Their M&A work typically involves Fortune 500 corporations evaluating strategic alternatives for non-core business units, liability management transactions, and private capital advisory (secondaries market advisory for private equity funds).
Sector Focus
CastleOak's industry coverage spans multiple sectors primarily for capital markets transactions:
Financial Institutions: Extensive experience with GSE debt (Fannie Mae, Freddie Mac, Farmer Mac), agency CMBS, and financial services corporations. The firm ranked #4 in CMA's Agency CMBS league table in 2024.
Infrastructure & Utilities: Public finance and municipal securities work, including utility revenue bonds and infrastructure project financing.
Real Estate: Commercial mortgage-backed securities (CMBS) and multifamily agency securities.
Basic Materials & Industrials: Corporate bond underwritings for industrial companies and manufacturers.
Healthcare & Pharmaceuticals: Investment grade and high yield debt offerings for healthcare systems and pharmaceutical companies.
Consumer Products & Retail: Corporate bond issuances and liability management for consumer-facing businesses.
Technology: Equity capital markets work including IPOs, follow-ons, and private placements.
Communications & Media: Debt and equity offerings for telecommunications and media companies.
Energy & Renewables: Project finance and bond issuances for energy infrastructure.
Government & Supranationals: Work with U.S. government agencies (FDIC, Federal Reserve) and supranational organizations like the World Bank.
Deal Track Record
CastleOak's transaction history is fundamentally different from traditional M&A advisors. Their "deals" are capital markets transactions:
- $5+ trillion in aggregate underwriting since 2006 across public offerings
- $650M+ in share repurchases executed for over 25 corporate clients
- $10B+ in notional value of shares repurchased in a single year through their electronic trading platform
- Agency CMBS leadership: Ranked #4 in CMA's Agency CMBS Lead and Co-Manager league table with 24 mandates in the first nine months of 2024
- GSE and agency securities: Regular co-manager on Fannie Mae Connecticut Avenue Securities (CAS) REMIC deals, Farmer Mac agricultural mortgage-backed securities (AMBS), and Freddie Mac multifamily securities
Recent Representative Transactions (2024-2025):
- Co-manager on Fannie Mae $659 million CAS REMIC deal (July 2024)
- Co-manager on Farmer Mac $308.1 million AMBS securitization (April 2024)
- Co-manager on Farmer Mac $318.8 million AMBS securitization (November 2024)
- Advisor on Fannie Mae tender offers for CAS notes (May 2023, ongoing)
- Multiple corporate bond offerings ranging from $300 million to $30 billion for investment grade and high yield issuers
M&A Advisory Work:
- Strategic alternatives advisory for a Fortune 500 company evaluating non-core business divestiture (2018)
- Financial advisor to KKR on S&P Global's sale of Engineering Solutions business (2023)
- Presentation to Pzena Investment Management's Special Committee regarding strategic alternatives (2022)
Notably, CastleOak does not have a track record of traditional lower middle market sell-side M&A transactions (sales of $10M-$250M businesses to private equity or strategic buyers). Their M&A work is limited to larger corporate transactions and capital markets-related advisory.
Process & Fee Structure
CastleOak's process is fundamentally capital markets-oriented:
Debt Capital Markets Process:
- origination, structuring, underwriting, and distribution of fixed income securities
- Investor relations and corporate access services
- Liability management and tender offer execution
- Methodical investor outreach strategies targeting Tier II-IV institutional accounts
- Differentiated distribution through minority-owned and emerging investment managers
Equity Capital Markets Process:
- IPO and follow-on offering execution
- Share repurchase program execution (10B-18 and 10B5-1 compliant)
- Block trading and program trading capabilities
- Algorithmic trading strategies on major execution platforms
Fee Structure: CastleOak's compensation model is transaction-based for capital markets work:
- Underwriting spreads on debt/equity offerings (industry-standard percentage of deal size)
- Trading commissions on secondary market transactions
- Advisory fees for strategic alternatives and M&A work (typically negotiated based on scope)
- No standard retainer model for lower middle market sell-side M&A
The firm does not publish a standard retainer or success fee structure for traditional M&A work, as this is not their primary business.
Buyer Network
CastleOak's distribution network is a key differentiator:
- 670+ Tier I-IV institutional accounts in fixed income trading
- Differentiated distribution to minority-owned, women-owned, and emerging investment managers
- Strong relationships with bulge-bracket bookrunners and lead managers for co-manager roles
- Government agency relationships: Approved underwriter for Fannie Mae, Freddie Mac, Farmer Mac, Federal Home Loan Banks, TVA, and IFC
- Strategic buyer access: Relationships developed through capital markets work with corporate issuers
However, CastleOak does not maintain the traditional PE buyer relationships that lower middle market M&A advisors rely on. Their network is oriented toward institutional investors, not private equity buyers of businesses.
Competitive Positioning
CastleOak differentiates through:
- Minority-Owned Status: 92% minority-owned, NMSDC-certified, 100% employee-owned since 2020
- Capital Markets Expertise: Top-ranked MWOB firm in agency, investment grade corporate, and structured finance underwritings
- Differentiated Distribution: Unique access to minority-owned and emerging investment managers overlooked by bulge-bracket firms
- Electronic Trading: Proprietary DirectPool™ bond trading platform and global equity trading with 24/6 market access
- Senior-Level Attention: Boutique firm model with founders' 20+ year working relationship
- Bulge-Bracket Experience: Senior bankers with extensive experience from Merrill Lynch, Lehman Brothers, and other major firms
Not a Fit If
CastleOak is not a fit for:
- Lower middle market companies ($5M-$250M TEV) seeking sell-side M&A representation
- Business owners looking for traditional M&A auction processes
- Companies needing pure-play M&A advisory without capital markets capabilities
- Sellers targeting private equity buyers (CastleOak's network is institutional investor-focused)
- Engagements below $10M TEV (minimum for their business model)
The firm is ideally suited for Fortune 500 companies, large corporates, government agencies, and institutional clients requiring capital raising, liability management, or strategic alternatives advisory.
Team
Leadership:
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David R. Jones, Co-Founder, President & CEO: 30+ years Wall Street experience. Formerly Head of Investment Banking and Capital Markets at Blaylock & Company. Previously at Merrill Lynch in investment banking and equity capital markets. MBA from Wharton, BS from Boston University. Named one of the 75 Most Powerful Blacks on Wall Street by Black Enterprise Magazine. Former Board of Overseers member at Boston University (2012-2019).
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Philip J. Ippolito, Co-Founder, Executive Vice President & COO: Co-founded CastleOak in 2006 after working with David Jones for over two decades. Manages firm operations and infrastructure.
Key Managing Directors:
- Patrick de Catalogne, Executive Vice President, Fixed Income
- Robert Bacon, Executive Vice President, Head of Capital Markets & Syndicate
- Reginald J. Hollinger, Managing Director, Head of Financial Advisory
- Carlos Cabana, Managing Director, Head of Equity Sales & Trading
- Daniel Chan, Managing Director, Head of DirectPool
- Dan Davis, Managing Director, Head of Fixed Income
- Jon Walker, Managing Director, Head of Fixed Income Sales
- James Guardino, Managing Director, Head of Money Fund Solutions
- Luis J. Gomez, Managing Director, Head of Finance
- David Boyd Booker, Managing Director, Head of Legal and Compliance
- Kisti Shah, Managing Director, Chief of Staff to the CEO
Advisors:
- Milton M. Irvin, Senior Advisor to the CEO
- Michael A. Turner, Executive Vice President & Senior Advisor
Geographic Coverage
Headquartered in New York City (200 Vesey Street, 3 World Financial Center) with regional offices in:
- Atlanta, GA
- Chicago, IL
- San Francisco, CA
- Los Angeles, CA
- Portland, OR
Total of 6 offices with approximately 75 professionals. The firm serves clients nationally and internationally through its electronic trading platforms and capital markets capabilities.