Chessiecap Securities Research
Advisory Approach
Chessiecap is a boutique investment bank founded in 2003 and serving emerging to mid-sized growth and technology companies. The firm operates with a clear thesis: business owners selling their companies face sophisticated buyers who do multiple deals annually, and they deserve investment bankers who can match that sophistication toe-to-toe. The firm's sweet spot is founder-owned technology, government services, and business services companies in the $5M-$100M enterprise value range. Chessiecap differentiates through Wall Street-trained expertise (both partners have decades of experience at firms like Drexel Burnham Lambert, First Boston, and Kaufman Bros.) combined with boutique-level attention and long-term client relationships.
The firm's anti-thesis is clear: they are not a fit for very small sub-$5M transactions, businesses in distress requiring turnaround work, or founders who want a limited process. Chessiecap believes in comprehensive buyer outreach and professional process management—they are not a "find a quick buyer" shop.
Sector Focus
Chessiecap has developed deep specialization in four growth and technology sectors:
IT Services & Software: The firm has completed multiple transactions in IT staffing (TSR Inc.), software platforms, and technology-enabled services. They understand SaaS models, recurring revenue dynamics, and the valuation metrics that matter to technology buyers.
Government Technology & Services: This is a core competency area. Chessiecap has advised multiple government contractors and international development consulting firms (Kaizen Company, IBI). They understand the nuances of government contracts, agency procurement cycles, and how strategic buyers value contract backlogs and vehicle registrations.
Communications & Media: Partner Brad Harries spent much of his 40-year career focused on telecommunications, giving the firm particular strength in telecom infrastructure, wireless services, and communications technology.
PropTech: The firm has developed expertise in property technology, real estate tech platforms, and construction-tech—a natural overlap with their government services and technology focus.
Beyond these four sectors, Chessiecap emphasizes broad transaction experience. They position themselves as investment banking generalists who can handle any middle market transaction, while offering specialized depth in growth and technology.
Deal Track Record
Chessiecap's team has led and partnered on transactions totaling over $20B in aggregate value throughout their careers. Recent completed transactions include:
-
TSR Inc. (2024): NASDAQ-listed IT staffing firm acquired by Vienna Parent Corporation (Justin Christian, founder of BCforward) for $13.40 per share, representing an 89.7% tender offer. Chessiecap provided the fairness opinion to TSR's Board of Directors, ensuring equitable terms for shareholders in a $26M+ transaction.
-
IBI Merger with URC (2024): International Business Initiatives, a 28-year-old international development consulting firm founded by Dr. Lucie Phillips, merged with University Research Co. (URC), a global healthcare quality improvement leader. Chessiecap represented IBI in bringing professional discipline to a negotiated sale with an identified buyer.
-
Kaizen Company Acquisition by Tetra Tech (2021): International development consulting firm Kaizen was acquired by Tetra Tech, a leading engineering and consulting services firm. Chessiecap facilitated the transaction, with client testimonials highlighting their guidance through "all the friction" of the acquisition process.
-
Student Opportunity Center Acquisition by PeopleGrove (2023): EdTech platform acquired by PeopleGrove, a student success platform. Chessiecap facilitated this transaction in the education technology space.
The firm has closed dozens of additional transactions across technology, government services, and business services sectors. Their experience spans sell-side and buy-side engagements, recapitalizations, and mergers.
Process & Fee Structure
Chessiecap runs institutional-quality processes adapted for lower middle market companies. Typical engagement structure:
- Retainer: Monthly retainer required (credited against success fee)
- Success fee: Industry-standard percentage structures tied to transaction value
- Process timeline: 6-12 months from engagement to close
- Buyer outreach: Comprehensive targeted buyer outreach, not limited processes
The firm emphasizes preparation: helping clients get ready for sale well before a transaction, improving financial reporting, cleaning up corporate structure, and positioning the business for maximum value. They provide strategic guidance even when a sale is years away—a long-term relationship approach that generates repeat business.
Buyer Network
Chessiecap maintains relationships with strategic buyers, private equity firms, and family offices. Their deal history shows successful exits to:
- Strategic buyers: Tetra Tech (Fortune 500 engineering/services), URC (global healthcare), PeopleGrove (edtech consolidator), BCforward (large Black-owned business)
- PE-backed vehicles: Vienna Parent Corporation (special purpose acquisition vehicle)
- International buyers: Cross-border transactions in government services and international development
The firm's deep Mid-Atlantic roots and Wall Street connections provide access to both regional and national buyer pools.
Competitive Positioning
Chessiecap differentiates through:
- Wall Street expertise, boutique attention: Partners with 30-40 years at major firms (Drexel, First Boston, Kaufman Bros.) providing hands-on service
- Government services expertise: Deep understanding of government contracting, international development, and federal procurement
- Long-term client relationships: Clients return for multiple transactions; the firm provides strategic advice years before any sale
- Process discipline: Professional-grade transaction management that levels the playing field against sophisticated buyers
- Mid-Atlantic focus: Strong presence in Maryland, Virginia, DC, with national capability
Not a Fit If
Chessiecap typically declines:
- Businesses below $5M TEV
- Distressed companies requiring turnaround expertise
- Founders wanting limited buyer outreach
- Pure asset sales (they focus on going-concern enterprises)
Team
Chessiecap is led by two partners with complementary backgrounds:
Doug Schmidt, Partner: 30+ years of investment banking experience. Former investment banker at Ferris, Baker Watts, Legg Mason Wood Walker, and an investor at Grotech Capital Group. Cut his teeth in the M&A department at Drexel Burnham Lambert. Harvard AB, Yale MPPM. Recognized as one of the most respected middle market investment bankers in the Mid-Atlantic. Doug is known for his "politely persuasive" negotiation style and has executed hundreds of transactions in M&A, private placements, and IPOs.
Brad Harries, Partner: 40+ years of Wall Street investment banking experience with deep expertise in telecommunications, information technology, and PropTech. Former positions at Kaufman Bros. (telecom boutique), Columbia Capital, Furman Selz, Cowen & Company, First Boston, Shearson Lehman Hutton, and Dean Witter Reynolds. Stanford AB in Economics and MBA. Brad's clients return to him decade after decade, reflecting his loyalty and dedication.
Both partners have served on boards of venture-backed companies and are active in the Mid-Atlantic business community.
Geographic Coverage
Primary location: Towson, Maryland (7911 Sherwood Avenue, Towson, MD 21204)
Core markets: Maryland, Virginia, Washington DC, Mid-Atlantic region with national capability for technology and government services transactions.