Meet Jim
Jim Sinai is a seasoned executive and local resident dedicated to the long-term stewardship of Central Coast businesses. After a career defined by building iconic organizations—most notably helping lead Procore through its landmark IPO—Jim is shifting his focus from global scaling to local leadership.
As a father of three boys and the spouse of a local entrepreneur, Jim is a permanent fixture in the Santa Barbara community. His goal is to acquire and personally operate a single, established business, or network of businesses, ensuring the culture and legacy built by the founder remain intact for years to come.
Our Focus
Acquisition Criteria
Oakside Ventures is seeking to partner with business owners who value a thoughtful transition and a dedicated long-term steward for their team and legacy.
Geography
Central Coast Focus: Santa Barbara, Ventura, and San Luis Obispo counties. We are locals who believe in being physically present in the business.
Financials
Stable Profitability: We typically look for businesses with annual EBITDA between $750k – $5M and a history of consistent cash flow.
Industry
B2B & Trade Services: Preference for resilient, service-based businesses, construction/trade technology, and niche light manufacturing.
The Seller
Owner-Operator: Ideally a founder looking to retire or step back, but who cares deeply about the ongoing success of their employees.
Operations
Low Concentration: A diverse customer base with no single client making up a vast majority of the revenue.
Philosophy
People First: 100% employee retention upon transition, focused on long-term growth rather than short-term cost-cutting.
If your business doesn’t fit every criterion but you believe Oakside could be a good partner, I welcome the conversation.