When it comes to achieving true financial freedom, there’s a vast difference between chasing hype and building a repeatable, trustworthy system. On a recent episode of “Raising Private Money,” Jay Conner sits down with Lane Kawaoka—an engineer turned real estate powerhouse—who has raised over $200 million in private capital and owns more than 10,000 units. Lane’s journey isn’t just impressive in numbers; it’s a how-to guide for investors ready to scale thoughtfully, avoid rookie pitfalls, and reach financial independence.

From Corporate Engineer to Real Estate Leader

Lane Kawaoka’s introduction to real estate investing wasn’t marked by overnight success. Instead, it grew from years of disciplined learning, starting with investing in single-family homes as early as 2009. Eventually, he transitioned from his high-paying engineering job to focus full-time on real estate, not because it was easy, but because he saw the power of repeatable systems. As Lane began raising private money, he relied on building strong relationships, first with friends and family, then expanding outward, always putting trust and alignment at the forefront.

Breaking the Million-Dollar Ceiling

Many new investors gather their first million through hustle—buying rentals, flipping properties, and leveraging local relationships for their first private loans. But what gets someone to one million often won’t get them to ten million and beyond. Lane’s “Wealth Elevator” framework breaks down the journey into distinct floors. 

The first floor involves building a solid base through savings and owning rentals. The second floor ushers in accredited investor status, where access to more lucrative, risk-managed deals becomes possible. The third floor is where investors with $3–4 million net worth begin to focus on preservation, shifting from aggressive growth to capital protection and diversification into vehicles like T-bills, life insurance, and private money lending.

Those in this second-floor space—the million to multi-million range—still need to take calculated risks. Simplistic “set it and forget it” strategies no longer suffice. Instead, these investors must evaluate deals with a discerning eye, balancing risk and reward as they work towards their ultimate financial freedom.

Systematic Decision-Making and Honest Conversations

Unlike many in the industry who pitch investments by inflating numbers and projecting excessive optimism, Lane prefers a system-driven, data-first approach. When considering a deal, he and his team start by examining raw financials—rent rolls, profit and loss statements, and cap rates—without manipulation. They look for conservative assumptions, such as cautious reversion cap rates and realistic rent escalators, instead of painting a rosy picture.

Importantly, Lane prioritizes transparency. He discusses not just why an investment could succeed, but openly points out possible risk factors. This willingness to “test the deal before looking at the answers” builds authenticity and long-term trust with investors. He draws a clear line: if a prospective investor requires constant reassurance or isn’t comfortable with the possibility of loss, private placements in real estate may not be the right fit.

Alignment Over Aggressive Pitching

The essence of Lane’s capital raising philosophy is simple: alignment. He treats raising money as a process of mutual fit, not of one-way persuasion. Potential investors are encouraged to think carefully about whether their personal goals, timelines, and risk tolerance align with the realities of multifamily deals, private lending, or syndications. Lane’s team offers open communication and a clear-eyed view of both the protections and limitations of their investments. Rather than pushing for a sale, they aim for every investor to go in “eyes wide open,” knowing both the upside and the possible storms ahead.