PRIVATE INVESTMENT FIRM
ANALYTICAL RIGOR. OPERATIONAL CONVICTION.
Wall Drawing #W-1 — A point three-fifths from the left edge and two-fifths from the top. A second point three-fifths from the right edge and two-fifths from the bottom. From each point, concentric arcs at all Fibonacci radii. Where arcs from both points pass within four units, a horizontal line is drawn in the second color.
01. Strategy
We invest in lower middle market businesses where reinforcing feedback loops are present but underleveraged — and where active management produces compounding equity value.
The lower middle market is where these dynamics are most exploitable. Too small for efficient pricing. Too complex for passive capital. Rich in data, poor in analysis. The businesses are undergoing generational transitions — aging owners, tightening regulation, accelerating technology adoption — and the operators who adapt capture the spread. We invest at that inflection.
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We target businesses generating $3M to $50M of EBITDA in fragmented, essential-services industries — non-discretionary end markets where operational complexity creates persistent mispricing and institutional structure compounds barriers to entry. We take control positions or structured minority stakes where we can drive operational outcomes through technology deployment, management professionalization, and process redesign. The value is created endogenously — inside the business, not in the capital structure. The firm has deployed capital across environmental services, infrastructure contracting, and business services.
TARGET SECTORS
Water & Wastewater Services
Specialty Healthcare Services
Environmental & Compliance Services
Electrical & Grid Infrastructure Services
Business & Professional Services
Facilities Management & Building Services
Wall Drawing #W-4 — Lines in four directions (vertical, horizontal, diagonal left, diagonal right) are drawn across the wall. Within each direction, lines are spaced at intervals following the Fibonacci sequence. Where lines from three or more directions pass through the same point, the intersection is marked in the second color.
02. Approach
I. Model the System
During diligence, we build a quantitative map of the feedback structures that drive performance — revenue loops, cost structures, capacity constraints, and the delays between them. Most operators rely on intuition. We start with data: identifying statistical patterns in pricing, utilization, retention, and throughput that reveal where the system compounds and where it stalls.
II Identify Leverage Points
Every system has two or three points where intervention produces disproportionate returns. The value creation plan — margin expansion, working capital optimization, pricing architecture — is underwritten before the LOI.
III Stress Under Nonlinearity
Markets are adaptive, not static. We stress-test every thesis across regime shifts — regulatory acceleration, labor market phase transitions, technology disruption, competitive entry — where the system behaves nonlinearly. If the base case depends on linearity, we pass.
IV Operate as Principal
A managing partner takes an active governance role from close — authority over value creation, capital allocation, and organizational design. We deploy technology, professionalize management, and build the institutional infrastructure that converts a founder-led business into a scalable platform.
03. Principals
Leigh Lommen
FOUNDER & MANAGING PARTNER
MBA, Columbia Business SchoolM.S. Financial Mathematics, University of MinnesotaB.S. Finance, University of Wisconsin–Madison
Mr. Lommen founded Winterfell Investments to apply quantitative discipline and principal-level conviction to lower middle market investing. He is a builder and investor who founded, grew, and scaled an essential-services platform to over $200 million in revenue through organic expansion and twenty-three acquisitions. Earlier, he traded derivatives professionally at the Chicago Board Options Exchange and the Chicago Mercantile Exchange.
Gustavo Castro e Silva
MANAGING PARTNER
MBA, MIT Sloan School of Management
J.D./LL.M., Northwestern University Pritzker School of Law
LL.B., IBMEC, Brazil
Mr. Castro e Silva leads the firm's investment process and portfolio strategy, bringing over fifteen years in private capital markets. He held investment roles at Arsenal Capital Partners, Guggenheim Partners, and CVC Credit Partners. Earlier, he served as senior counsel at BNDES, Brazil's national development bank, advising on structured finance and infrastructure transactions across Latin America.