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SI Ventures
SI Ventures is the Fort Myers single-family office investing directly in enterprise software and AI infrastructure companies.
SI Ventures
SI Ventures deploys from Fort Myers, Florida, functioning as the direct investment vehicle for a single-family balance sheet. The firm was established to pursue venture-stage technology opportunities without the fund-life constraints that shape venture-capital decision-making. Its mandate covers enterprise software, data infrastructure, and applied AI — sectors where product adoption cycles reward longer holding periods. Investment activity concentrates on Seed through Series B rounds, with typical initial checks ranging from $500,000 to $3 million. SI Ventures participates almost exclusively in direct equity deals, occasionally joining syndicates led by domain-specialist venture funds. Known portfolio positions include enterprise SaaS and cybersecurity businesses serving financial institutions and healthcare payers — segments where procurement cycles are slow but customer retention runs high. The firm co-invested alongside FTW Ventures and other specialists in a food-science data platform (per public record, 2022), confirming willingness to back technical founders at the pre-revenue stage. Geographic focus spans the United States, with a concentration of portfolio activity in Florida and the Southeast, though the firm has participated in deals across the Northeast and West Coast technology corridors. SI Ventures maintains a lean structure, with investment decisions centralized under its CIO. The office does not publicly disclose total assets or cumulative deployment. It does not operate a registered fund vehicle, accept outside capital, or maintain a philanthropic foundation under the SI Ventures name. In May 2023, the firm's CIO appeared on a Fort Myers business podcast discussing the regional startup ecosystem (per public record, May 2023), reflecting a posture of local ecosystem engagement without publishing formal deal announcements. SI Ventures represents a pattern increasingly common among single-family offices: migrating from fund-of-funds allocations toward direct company ownership. The structural advantage lies in time-horizon flexibility. Without return deadlines imposed by limited-partner agreements, the firm can hold positions through multiple down-cycles — an underwriting posture that matters most in enterprise infrastructure and regulated-market software, where compound growth often appears in the second decade of ownership rather than the third year.
General information
Firm type
Single Family Office
Year founded
—
AUM
Undisclosed
Location
Region
North America
Country
United States
City
Fort Myers
Corporate office
Fort Myers, FL, United States
Principals
Rocco Basilico
Chief Investment Officer
Sector focus
Frequently asked questions
Who runs investment decisions at SI Ventures?
Rocco Basilico serves as Chief Investment Officer and directs the firm's investment activity. His background includes operating and finance roles that preceded the family-office mandate. Investment decisions are made centrally rather than through a distributed committee structure, consistent with the firm's concentrated-portfolio approach.
Does SI Ventures operate as a single-family office or does it manage outside capital?
SI Ventures functions as a single-family office deploying proprietary capital. The firm does not register as an investment advisor, does not accept outside limited partners, and does not market a fund vehicle. All portfolio positions represent balance-sheet investments from a single family source.
What investment stages and check sizes does SI Ventures typically target?
The firm invests from Seed through Series B, with initial checks generally falling between $500,000 and $3 million. SI Ventures often writes the first or second institutional check into a company, positioning itself before larger venture funds enter. It does not operate a growth-stage or buyout strategy, and it does not participate in secondary transactions as a primary activity.
How does SI Ventures source its deals?
SI Ventures relies primarily on direct founder relationships and its network in the Southeast technology corridor, supplemented by co-investor syndicates with domain-focused venture funds. The firm's Fort Myers base gives it differentiated access to Florida's growing startup density while maintaining ties to West Coast and Northeast deal flow. The firm has publicly indicated it does not rely on a proprietary sourcing platform or broker-intermediated deal flow.
Which sectors does SI Ventures explicitly avoid?
SI Ventures concentrates on enterprise software, AI/ML, cybersecurity, and digital health. It generally avoids consumer internet, hardware-heavy deep tech, media, and life-sciences therapeutics — sectors where either capital intensity or consumer-adoption risk misaligns with the office's concentrated-balance-sheet posture. The firm has also steered clear of crypto and web3-native investments to date.
Profile maintained by Altss using OSINT (open-source intelligence), regulatory filings, licensed data partners, and verified direct submissions. Read the methodology. Last updated: . Continuous refresh with full update cycles at least every 30 days.
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