Capital Strategies Group Research
Advisory Approach
Capital Strategies Group (CSG) is a lower-middle market M&A advisory firm founded in 1993 with over three decades of experience advising business owners and their families on strategic capital transactions. Led by founder and Managing Partner David Simon, CSG operates with a thesis-driven approach centered on understanding client objectives and delivering practical, relationship-focused advisory services. The firm believes that successful outcomes in lower-middle market M&A require deep industry knowledge, institutional process discipline, and long-term client relationships built on trust and proven execution.
CSG's philosophy emphasizes being a trusted advisor rather than a transaction factory. With over 100 transactions closed across David Simon's career (starting in investment banking in 1991), the firm has developed distinctive expertise in matching business owners with aligned buyers, navigating complex capital structures, and executing deals in industries where operational complexity makes valuation non-obvious.
Market Position & History
Since 1993, Capital Strategies Group has established itself as a respected fixture in the Florida and Southeast lower-middle market M&A landscape. The firm is relationship-oriented and works to provide creative and value-enhancing solutions tailored to each client's unique strategic objectives. In February 2023, CSG was acquired by 1858 Capital Partners, an investment bank based in Winter Park, Florida, allowing the firm to expand its service capabilities while maintaining its advisory heritage.
David Simon, the firm's founder, has been active in the Florida business community since 1979 when he started his career with Sun Bank (now Truist Bank). He transitioned into investment banking in 1991 with Allen C. Ewing & Company and founded Capital Strategies Group in 1993 at age 35, bringing extensive relationship and deal experience into the new venture.
Service Offerings
Capital Strategies Group offers a comprehensive range of investment banking and financial advisory services:
- Company Sales & M&A Advisory: Full-service sell-side and buy-side M&A advisory, from initial valuation and buyer identification through closing and integration planning
- Private Placements & Capital Raising: Debt and equity capital raising for growth, recapitalizations, and leveraged buyouts
- Buy-Side Advisory: Acquisition advisory for buyers, including due diligence support, seller identification, and negotiation strategy
- Corporate Finance: Complex capital structure optimization, bridge financing, and financial restructuring
- Mezzanine & Bridge Financing: Structured debt solutions for gap financing and LBO financing
- Balance Sheet Restructuring: Debt restructuring, bankruptcy alternatives, and financial workouts
- Strategic Consulting: Business valuation, fairness opinions, and strategic planning
Deal Track Record
Capital Strategies Group has completed 11 documented transactions across diverse industries. Recent transaction highlights include:
2023 Transactions:
- Advised on acquisition of Pfingsten Partners LLC (industrial supplies distributor) by Industrial Lighting Products
- Advised on acquisition of Preferred Voice, Inc. (telecommunications services) by ClearSky Technologies
- Advised on acquisition of Class Valuation (real estate services) by Accusured Management
- Advised on acquisition of Encompass (business support services) by CyberTest
- Advised on acquisition of Asset Repair & Conditioning, Inc. (industrial services) by North American Substation Services
- Advised on acquisition of Grovecourt Capital Partners (transportation services) by Traffic & Mobility Consultants
2022 Transactions:
- Advised Aqua Leisure Recreation on acquisition of INYO Pool Products (consumer products), a Blackford Capital platform add-on acquisition
Earlier Transactions:
- Alpine Investors acquired by Frank Gay (2019) — business services
- Dole transaction with Sunnyridge (2011) — food manufacturing
- Brience acquired by Data on Air (2000) — software and online services
These transactions demonstrate CSG's ability to execute across economic cycles, multiple industry sectors, and with diverse buyer profiles including strategic acquirers, PE-backed platforms, and financial sponsors.
Industry Specialization & Sector Focus
While CSG maintains a generalist lower-middle market practice, the deal history reveals particular strength and active practice in:
Industrial & Manufacturing Services: Significant experience advising companies in industrial supplies distribution, machinery manufacturing, precision equipment repair, and specialized manufacturing. The firm understands operational complexity in asset-intensive businesses and has worked with both owner-operators and PE-backed consolidation platforms.
Technology & Professional Services: Active practice advising software companies, online services businesses, and business services providers. Demonstrates ability to navigate growth stage exits and digital transformation M&A.
Business & Professional Services: Repeated activity advising on sales of support services companies, staffing firms, and management services businesses. Understands the market for service business roll-ups and platform acquisitions.
Consumer & Specialty Products: Experience with branded consumer products, recreational product manufacturers, and direct-to-consumer businesses. Demonstrated success with acquisition target identification and buyer matching in this space.
Healthcare & Specialty Services: Involvement with healthcare-adjacent businesses and professional services.
Buyer Network & Strategic Relationships
CSG's transaction history reveals relationships with multiple categories of acquirers:
- Strategic Buyers: Large industrials, platform companies, and operational acquirers seeking bolt-on acquisitions or tuck-in deals
- Private Equity: Relationships with PE-backed platforms (e.g., Blackford Capital for the Aqua Leisure acquisitions) and independent sponsors seeking LBO targets
- Family Offices & Individuals: Experience advising on sales to founder-led buyers and family office investors
The firm's 30-year operating history in Florida and Southeast region provides built-in relationships with local and regional buyer networks.
Geographic Coverage
Capital Strategies Group's historical focus has been Florida-based business owners and Southeast regional companies. The firm maintains relationships across Florida's major business centers including Orlando, Tampa Bay, Miami, and Jacksonville. Following acquisition by 1858 Capital Partners (Winter Park, FL), the firm has access to expanded geographic reach while maintaining its core Florida market expertise.
Process & Client Approach
CSG employs a disciplined yet flexible approach to M&A advisory:
- Discovery & Objective Setting: Comprehensive conversations to understand client financial objectives, timeline constraints, family dynamics, and strategic priorities
- Valuation & Market Assessment: Independent valuation analysis and assessment of current market conditions for the client's business
- Buyer Universe Development: Identification of strategic and financial buyers, tier 1 vs. secondary buyers, and outreach strategy
- Process Management: Running an organized, confidential process with NDA execution, management presentation preparation, and data room assembly
- Negotiation & Deal Structuring: Tax-efficient deal structuring, earnout negotiation, and non-compete agreement review
- Closing Support: Due diligence management, regulatory approval coordination, and final close preparation
The firm's emphasis on understanding client objectives and customizing the advisory approach differentiates CSG from transactional advisors focused solely on deal volume.
Team & Leadership
David Simon — Founder & Managing Partner
- 45+ years in finance and investment banking
- Joined Sun Bank (now Truist Bank) in 1979 in commercial banking
- Began investment banking career with Allen C. Ewing & Company in 1991
- Founded Capital Strategies Group in 1993
- Led or co-led over 100 corporate finance and investment banking transactions including company sales, capital placements, and complex debt financing
- Active in Florida business community; founding member and President (2013) of the Orlando Chapter of the Association for Corporate Growth (ACG)
- Board member and former President of the Board of the Edgewood Children's Ranch
- Graduate of Miami University in Oxford, Ohio
Additional team members bring experience in accounting, corporate finance, and transaction management, though detailed team roster was consolidated following 1858 Capital Partners acquisition.
Competitive Positioning
Capital Strategies Group differentiates through:
- Deep Relationship Capital: 30-year operating history in Florida with established relationships across buyer networks, lenders, and business communities
- Founder-Led Expertise: David Simon's personal involvement and 45+ year career in finance ensures institutional knowledge and continuity
- Industry Versatility: Experience across diverse sectors (manufacturing, technology, consumer, services, healthcare) provides flexibility in buyer matching
- Valuation & Finance Depth: Strong financial modeling and valuation expertise, evidenced by involvement in complex recapitalizations and bridge financing structures
- Relationship-Oriented Philosophy: Focus on understanding client objectives rather than simply maximizing transaction volume
Not a Fit If
CSG may not be the best fit for:
- Businesses below $5M in EBITDA (minimum engagement size not publicly stated, but transaction history suggests lower end of middle market focus)
- Companies seeking West Coast or international buyer access (regional focus)
- Distressed/insolvency situations requiring restructuring expertise (though balance sheet restructuring services offered)
- Highly time-sensitive sales (firm emphasizes process discipline over speed)
Recent Activity & Momentum
The acquisition by 1858 Capital Partners in February 2023 positions CSG for expanded service delivery in the Florida and Southeast region. 1858 Capital Partners brings institutional backing, enhanced debt financing capabilities, and principal investing capacity alongside CSG's advisory heritage. Transaction activity continued through 2023, with multiple acquisitions closed in July 2023 and other strategic transaction work underway.
Foundation for Success
Capital Strategies Group has demonstrated staying power and client loyalty across 30 years of lower-middle market M&A. The combination of founder expertise, regional relationship capital, industry versatility, and transition to institutional backing positions the firm well to continue serving business owners navigating strategic capital events.