Cheval Capital Research
Advisory Approach
Cheval Capital is a specialized boutique investment bank focused exclusively on the Cloud, Hosting, MSP, and related Internet services sectors. Founded by Hillary and Frank Stiff, the firm has completed over 700 Internet services M&A transactions since the 1990s, making them one of the most experienced advisors in this niche market.
The firm operates with a thesis-driven approach: deep sector specialization creates superior outcomes. Unlike generalist boutiques that dabble in technology, Cheval's principals live and breathe hosting and cloud M&A. They've been active in the web hosting M&A arena since the industry's inception, giving them institutional knowledge of valuation trends, buyer preferences, and deal structures that generalist banks simply cannot replicate.
Cheval differentiates through its Cheval Opportunities List program—a unique service for smaller hosters and cloud providers that connects sellers with an estimated 1,000+ pre-qualified prospective buyers. This program, redistributed by industry bankers and brokers, enables quick, effective transactions for businesses that might be too small for traditional sell-side processes.
Sector Focus
Cheval's practice is 100% focused on Internet infrastructure and services:
Managed Services & Hosting (IT Services/MSP): Web hosting companies, shared hosting providers, VPS and dedicated server hosting companies, managed service providers, ISP businesses. This is their core competency with 700+ completed transactions.
Software & Cloud Infrastructure (SaaS/IaaS): Infrastructure-as-a-Service providers, bare metal cloud providers, cloud platforms, and related software businesses. The Heficed acquisition exemplifies this subsector.
Telecommunications & Network Infrastructure: Fiber networks, data center infrastructure, and telecom-related assets. The Fiberlight sale to Morrison & Co demonstrates capability in larger infrastructure transactions.
Deal Track Record
Cheval has completed over 700 Internet services M&A transactions across North America, Europe, and other international markets. The firm works with a wide spectrum of transaction sizes, from smaller hosting companies needing the Opportunities List program to larger infrastructure deals requiring traditional sell-side processes.
Recent and representative transactions include:
2025: Advised World Host Group on a series of transactions including A2 Hosting, Webcentral, DotEasy, LuxHosting, and Wingu Networks. This multi-transaction engagement demonstrates Cheval's ability to manage complex consolidations and roll-up strategies.
2023: Hivelocity (U.S. IaaS hosting and bare metal cloud provider) acquired Heficed, a UK-based Infrastructure-as-a-Service provider with offices and data centers globally. Cheval M&A advised on this cross-border transaction.
2019: Advised Miss Group on double acquisition of Hostek (U.S.-based web hosting company, $7.5M revenue, 15,000 customer accounts) and a Canadian shared web hosting company ($2.5M revenue, 16,000 customers, 28,000 new accounts). Both transactions involved complex customer base integrations.
2022: Fiberlight sold to a group led by Morrison & Co. Fiberlight operates 14,000+ miles of fiber with 78k on or near-net buildings along the East Coast. This transaction represented one of the most speculated-about fiber M&A transactions on the East Coast.
Other notable transactions: Represented AppRiver on its sale to Zix for $275 million; completed 500th Hosting, Cloud & Internet Services transaction in 2019.
Process & Fee Structure
Cheval runs both traditional sell-side processes and its proprietary Cheval Opportunities List program, depending on transaction size and client needs.
For larger transactions (typically $5M+ TEV), Cheval conducts structured sell-side processes with targeted buyer outreach. The firm maintains relationships with 1,000+ pre-qualified prospective buyers through its Opportunities List distribution network, which includes industry bankers, brokers, and strategic buyers.
For smaller transactions (typically sub-$5M TEV), the Cheval Opportunities List program provides a streamlined alternative. The list reaches an estimated 1,000+ pre-qualified buyers and enables quick, efficient closings—ideal for founders who want to exit faster without a full marketing process.
Timeline: Traditional sell-side processes typically run 4-6 months from engagement to close, while Opportunities List transactions can close in 60-90 days depending on buyer readiness and due diligence complexity.
Buyer Network
Cheval maintains one of the industry's most extensive networks of Internet infrastructure buyers, built over 30+ years and 700+ transactions:
Private Equity & Infrastructure Funds: Morrison & Co (infrastructure specialist), various PE-backed strategic buyers in the hosting space.
Strategic Buyers: World Host Group (consolidator), Hivelocity, Zix (email security), major hosting and cloud companies seeking expansion through acquisition.
International Buyers: Miss Group (European consolidator active in North American acquisitions), cross-border buyers seeking U.S. or European hosting assets.
The Cheval Opportunities List, redistributed by industry bankers and brokers, extends the firm's reach to an estimated 1,000+ pre-qualified prospective buyers—including many who are not publicly seeking acquisitions but would consider the right opportunity.
Competitive Positioning
Cheval Capital differentiates from other LMM M&A advisors through:
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Unmatched sector focus: 100% of practice dedicated to Cloud, Hosting, MSP, and Internet services—no distraction from other industries.
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Transaction volume: 700+ completed transactions gives them data on valuation, pricing, and buyer preferences that no generalist bank can match.
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Proprietary buyer network: Cheval Opportunities List reaches 1,000+ pre-qualified buyers through unique distribution channels.
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Cross-border capability: Active in North America, Europe, and international markets with experience managing cross-border transactions (e.g., Hivelocity/Heficed, Miss Group's North American acquisitions).
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Industry involvement: Frank Stiff serves as Board member and Chair Elect of the I2 Coalition (Internet Infrastructure Coalition), giving Cheval visibility into policy and industry trends affecting hosting and cloud businesses.
Not a Fit If
Cheval typically declines:
- Businesses outside Cloud, Hosting, MSP, and Internet services sectors
- Companies under $1M TEV (their programs target $1M-$250M+ range)
- Pure technology companies without infrastructure or services components
- Asset sales or distressed situations (they focus on going-concern businesses with customer bases)
Team
Hillary Stiff, President of Cheval M&A: Investment banker since 1990, former CFO with deep experience in M&A transactions and financing arrangements. Completed transactions for Nextel Communications, NTT/Verio, The Endurance International Group, and Web.com. Has helped complete over 700 successful web hosting, ISP, and related transactions. Popular conference speaker who has led panels at HostingCon, SWSoft Partner Summit, and other industry events.
Frank Stiff, President of Cheval Capital: 30 years of investment banking experience. Clients have included Nextel Communications, NTT/Verio, Fidelity Capital/Colt Telecommunications, and Rackspace Managed Hosting. Board member and Chair Elect of the I2 Coalition, the leading voice for web hosting companies, data centers, domain registrars, and cloud infrastructure providers.
The firm operates as a small boutique with Hillary and Frank as the primary principals, supported by a lean team focused exclusively on Internet infrastructure M&A.
Geographic Coverage
Headquartered in Alexandria, Virginia (620 Oakland Terrace, Alexandria, VA 22302), Cheval serves clients across North America, Europe, and international markets. The firm has completed transactions for companies in the U.S., Canada, UK, and other European countries. Cheval's cross-border experience includes representing U.S. buyers acquiring European assets (Hivelocity/Heficed) and European buyers acquiring North American companies (Miss Group's acquisitions of Hostek and Canadian hosting companies).