Building Onarock Investments: How Jake Whitney is Turning a Passion for Real Estate into a $100M Portfolio

Episode SummaryIn this episode of Groundbreakers, Jake Whitney, co-founder of Onarock Investments, shares his journey from the marketing tech world to building a purpose-driven real estate firm with a $100M vision. Jake discusses how his grandfather’s rental portfolio inspired him to take the leap from passive investing to full-time syndication, and how he and his team are scaling Onarock deal by deal.Key Points DiscussedFrom Passive Rentals to Full-Time Syndication: Jake’s path began with single-family rentals and small multifamily properties before moving into larger deals with his partners at Onarock Investments.Flipping to Syndicating: He explains lessons learned from flipping mobile home parks, sixplexes, and even an office space—plus how those early deals shaped his current underwriting standards.Scaling with Purpose: Jake shares the systems and criteria Onarock uses to target 12–14% IRRs and often exceed them with 24–30% exits, while keeping cash flow as a safety net.Legacy and Mission: Beyond returns, Jake talks about honoring his grandfather’s legacy of integrity and freedom through real estate and how that mission drives his approach to investors and deals.Guest InformationName: Jake WhitneyRole: Co-Founder at Onarock InvestmentsLinkedIn: Jake WhitneyWebsite: Onarock InvestmentsConclusionJake Whitney’s story is an inspiring look at how to transition from a corporate career to purpose-driven syndication. His focus on discipline, investor trust, and building systems has helped Onarock grow from small flips to a platform with a $100M vision.Connect with Jake on LinkedIn to learn more about his work at Onarock Investments and his approach to scaling syndications with integrity.