Windward Equity is an operator-led investment firm focused on acquiring and scaling founder-led businesses generating between $1 million and $5 million in EBITDA. With more than $300 million in assets under management, Windward combines hands-on operating expertise with modern systems and a stewardship mindset to unlock value in overlooked businesses. Founded by Kyle Ewing, a $40 million entrepreneur and the founder of TerraSlate and Big Island Honey Co., Windward Equity invests in legacy companies that have strong cash flow, loyal customers, and untapped potential. These are not distressed businesses—they are well-built operations that need fresh energy, updated systems, and visionary leadership. What sets Windward apart is its unique blend of operational empathy and execution. We implement tools like the Entrepreneurial Operating System, leverage AI and automation for scale, and preserve the culture that made these businesses special. From branding and storytelling to performance turnarounds, our approach is immersive and results-driven. We actively partner with family offices and high-integrity founders who want to grow without compromising what they’ve built. Whether you are exploring succession, looking for co-investment opportunities, or want to transform passive capital into something active and meaningful, Windward brings the team and the playbook to help you scale. We do not chase trends. We build enduring companies through grit, modern tools, and deep respect for the businesses we serve.
| Employees | 1 (0 on RocketReach) |
| Founded | 2021 |
| Industry | Financial Services |
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Windward Equity is based in Kapalua, Hawaii.
