Lane Kawaoka, a US-based investor and millionaire, says his journey to financial success came with an unexpected challenge — loneliness.
Speaking to Business Insider, Kawaoka shared that he grew up in a modest household in Hawaii, where frugality was a way of life. “We never ordered soda at restaurants,” he recalled. After earning an engineering degree and getting a job, he saved aggressively and bought his first rental property in Seattle in his late 20s. By 2015, he owned 11 units and had crossed the million-dollar net worth milestone.
Growing distance with friends and co-workers
But instead of celebration, Kawaoka says the achievement created distance. “It gets lonely. Not because of the money, but because you feel like you can’t talk about it,” he told the publication. Conversations with old friends became strained. “My coworkers didn’t understand things I found important. My old friends still saw debt as dangerous and opted for 15-year mortgages,” he said.
Kawaoka stopped discussing his goals to avoid sounding boastful and feared being expected to pick up bills. “I felt like a ghost in my own life,” he said, describing himself as a “lone wolf” among peers still focused on 401(k) plans.
Finding his clan
The turning point came in 2016 when he joined a real estate mastermind group. “For the first time, I met people who spoke my language,” he said. These groups, including Entrepreneurs’ Organisation and Vistage, offered structured spaces for high performers to talk openly about business and money. At one event, attendees even wrote their net worth on name tags — not to brag, but to be transparent.
Kawaoka says meeting other first-generation wealth builders brought relief. “They weren’t any smarter; they were just more persistent,” he noted. The shared focus on tax efficiency, estate planning, and multi-generational wealth helped him feel understood. “I realised I wasn’t introverted; I was an extrovert who’d never found his tribe.”
Today, Kawaoka rarely discusses money with old friends. Instead, he invests in relationships with those who share his values. “Self-made net worth tends to be a good filter for connection,” he said. “It’s not about flaunting it; it’s just a helpful signal.”
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