Lakeside Capital is the private investment office of Trevor Paladino, a serial entrepreneur turned investor. We pursue a multi-strategy approach across venture capital and private equity, ranging from early-stage investments to lower middle-market opportunities. Our portfolio spans technology startups, consumer brands, industrial and home services businesses, and professional sports teams.
As a single-source investment office, Lakeside deploys proprietary capital—providing the flexibility to invest across stages, sectors, and structures without external constraints. This independence allows us to move with speed, partner closely with founders and operators, and focus on building enduring value.
We invest in founders to accelerate value creation through capital, connection, and collaboration. With deep roots across sports, media, and consumer sectors, we bring more than capital — we bring momentum. Beyond providing capital, Lakeside offers strategic guidance and access to an unparalleled network cultivated over nearly twenty years in the sports and business ecosystem. Our relationships span top athletes, entertainers, media figures, and senior executives across leagues, teams, and leading consumer brands shaping the future of sports. We actively open this network to help founders gain traction, secure partnerships, and scale faster. Grounded in flexibility and focus, we stand shoulder-to-shoulder with founders to help them navigate complexity, execute with intention, and create lasting impact.
We bring a long-term, strategic mindset to every investment. As a trusted partner, we offer business-building expertise, deep industry insight, and a focus on scaling with clarity and intent. Grounded in experience and execution, we work closely with our portfolio companies to unlock value, navigate complexity, and drive meaningful growth. Our approach is collaborative, thoughtful, and designed to support ambitious teams as they build enduring businesses.
With nearly 20 years in the sports industry, we’ve built a trusted network of relationships that continues to create value across our portfolio. This depth of access enables us to open doors to potential customers, strategic partners, and key stakeholders — helping our companies gain traction and scale faster.
We believe relationships drive results. That’s why we actively leverage our network to help founders unlock opportunities, build credibility, and create long-term advantage.
We focus on unlocking value where it matters most — helping companies sharpen their strategy, scale efficiently, and build long-term advantage. Our approach is rooted in clarity, prioritization, and momentum.
From navigating inflection points to strengthening business fundamentals, we bring the insight and discipline needed to support meaningful, sustainable growth. We don’t just back companies — we help build them to last.
For nearly two decades, our founder has cultivated a network that extends far beyond connections—it’s a true ecosystem of relationships built on trust, shared success, and deep involvement in the sports and business landscape. His network spans top athletes, agents, media figures, and senior executives at leagues, teams, and leading consumer brands shaping the future of sports and entertainment. We actively engage this network to create tangible value for our portfolio companies—unlocking introductions to potential customers, strategic partners, talent, and industry insights that accelerate growth. This level of access gives our portfolio companies a distinct edge, helping them gain credibility, scale faster, and seize opportunities others can’t replicate.
At Lakeside, we don’t just open doors—we stand alongside founders to help them walk through them, ensuring relationships translate into real momentum and meaningful outcomes.
