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This panel introduces investors discussing how family offices and operators are allocating and scaling amid higher interest rates. Lane Kawaoka, a Hawaii-based former engineer, shares his path from buying 11 rentals by 2015 to operating over $2B in apartment acquisitions, and explains why rising holding costs, insurance, and taxes have pushed him to also act as a multifamily office seeking opportunities beyond real estate. The conversation highlights a contrarian, P&L-driven approach, emphasizing grassroots relationship-based deal flow with long-term partners (brokers, contractors, vendors) and special real estate structures where developers need short-term capital to finish projects. The panel also covers using AI and quantitative checklists to quickly screen deals and reduce underwriting workload, plus a “$30k rule” of paying trusted third-party consultants to validate financials when investing outside core expertise.
00:00 Panel Kickoff
00:27 Lane Kawaoka Intro
01:33 Contrarian Investing Approach
03:11 Creative Deal Structures
04:20 AI Underwriting Workflow
05:29 Million Dollar Insight
06:49 Audience Q&A Wrap
Connect with me:
LinkedIn: https://www.linkedin.com/in/lanekawaoka/
Facebook: https://www.facebook.com/TheWealthElevator
Instagram: https://www.instagram.com/TheWealthElevator
Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016.
Check out our Top-50 Investing Podcast, The Wealth Elevator.
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