Gerald Castaldo
Senior Associate
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- Full Name
- Gerald Castaldo
- Title
- Partner, Investments
- Firm
- LoneTree Capital
- Firm Type
- Growth capital / private equity
- Investment Stage
- Growth equity, recapitalizations, acquisitions, and buyouts
- Check Size
- $10M-$75M
- Target Company Profile
- Revenue of $5M-$30M, >10% growth, recurring or re-occurring revenue, break-even to positive cash flow or unit-level profitability
- Sector Focus
- Software, financial technology / specialty finance, digital infrastructure, healthcare IT / services, business services, consumer services
- Geographic Focus
- Primarily U.S. and Europe based on published portfolio and transaction activity
- Location
- New York, NY
Background
Gerald Castaldo is Partner, Investments at LoneTree Capital, a New York-based growth capital firm founded in 2021. LoneTree announced on January 7, 2026 that Castaldo joined as Partner as part of an expanded leadership team following the close of LoneTree I, its inaugural $200 million fund.
Before LoneTree, Castaldo was a Principal at H.I.G. Growth, the dedicated growth capital platform of H.I.G. Capital, where he focused on majority and minority growth equity investments in software and technology-enabled companies. H.I.G. Growth describes its mandate as investing in growing technology-oriented businesses across North America, Europe, and Latin America, with focus areas including SaaS, cloud and data software, technology-enabled services, consumer/e-commerce, and healthcare technology.
Prior to H.I.G., Castaldo spent eight years at Bregal Sagemount, an operations-focused growth equity firm, where he led or participated in technology investments across software, healthcare IT, financial technology, business services, and consumer services. Earlier, he began his career in the Mergers and Acquisitions Group at Greenhill & Co. He holds a BS in Finance and Accounting from New York University’s Stern School of Business.
Investment Thesis & Focus
- LoneTree targets lower-middle-market technology and tech-enabled services companies where it can combine capital with operational and M&A support.
- The firm is capital-structure flexible: LoneTree says it can provide capital for “shareholder liquidity, growth investments, acquisitions, recapitalizations, and full buyouts.”
- Current investment criteria include $10M-$75M investment size, $5M-$30M revenue, >10% company growth, common/preferred equity or subordinated debt, and control or non-control roles where LoneTree is typically lead investor.
- LoneTree specifically calls out founder-owned bootstrapped businesses, divisions of larger enterprises, and formerly venture-backed companies as partner-company profiles.
- Castaldo’s stated motivation for joining LoneTree was to help build “a differentiated growth investment platform,” drawing on experience scaling his prior firm to $4 billion in AUM.
Notable Investments
- Solo — Solar sales, proposal, and design software provider; Bregal Sagemount announced a minority strategic growth investment in September 2022, and the investment was led by Pavan Tripathi, Sandeep Swaminathan, Gerald Castaldo, and Harrison Boyajian.
- Procurement Advisors / Procure Analytics — Technology and data-enabled group purchasing organization focused on MRO spend; Bregal Sagemount announced a significant growth investment in June 2019, with Castaldo listed among the deal leads.
- Printful — Print-on-demand and fulfillment company; Bregal Sagemount made a $130 million non-control investment in May 2021, establishing Printful as a unicorn. MarketScreener/Zonebourse lists Castaldo as a private equity investor connected to Printful since 2021.
- Bite Squad — Food delivery marketplace; Bregal Sagemount invested in 2017 and the investment is marked realized. MarketScreener/Zonebourse lists Castaldo as a board member / investor from 2017 to 2019; Waitr completed its acquisition of Bite Squad in January 2019.
- Invoca — AI-powered revenue execution / conversation intelligence platform; H.I.G. Growth Partners is listed among Invoca’s investors, and Castaldo publicly shared Invoca’s May 2025 acquisition of Symbl.ai while at H.I.G.
- Balena — Edge AI and IoT fleet-management platform; LoneTree announced a strategic growth investment in January 2026, shortly after Castaldo joined the firm.
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