Lane Kawaoka, a US-based investor and millionaire, says his path to financial success brought an unexpected challenge: loneliness. In an interview with Business Insider, he shared that growing up in a modest Hawaiian household taught him to be frugal. After studying engineering and getting a job, he saved aggressively and bought his first Seattle rental property in his late 20s. By 2015, he owned 11 units and hit a net worth of over a million dollars. But instead of feeling celebratory, Kawaoka says hitting that milestone 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. He found his coworkers didn't understand things he found important, and his old friends still saw debt as dangerous, opting for 15-year mortgages. Kawaoka stopped discussing his goals to avoid sounding boastful and feared being expected to pick up bills. He felt like a ghost in his own life, describing himself as a lone wolf among peers still focused on 401(k) plans.
The turning point came in 2016 when he joined a real estate mastermind, a group of investors who connect and share insights. For the first time, he met people who spoke his language. They weren't impressed with his earnings because they made similar or more. They just wanted to discuss the industry. Groups like Entrepreneurs' Organization (EO) and Vistage gave him a starting point - structured, vetted environments where high performers could openly discuss business, money, and personal growth.
Kawaoka says meeting other first-generation wealth builders brought him relief. They weren't prodigies or geniuses, but more persistent, he noted. The shared focus on tax efficiency, estate planning, and multi-generational wealth helped him feel understood.
"More than anything, I felt relieved — relieved that I wasn't weird and relieved that I wasn't the only one thinking about tax efficiency, estate planning, and building multi-generational wealth in my 30s," he said.
He realised he wasn't introverted; he was an extrovert who had never found his tribe.
"I still remember a dinner with a small group of fellow real estate investors. The conversation was fluid, deep, and energizing. No one held back. It was the first time I felt truly understood — and I didn't want the night to end," he added.
Today, Kawaoka rarely discusses money with old friends. Instead, he invests in relationships with those who share his values.
"It's not about flaunting it; it's just a helpful signal. Because when you meet someone else who's built it from scratch, you tend to speak the same language — even before you say a word," he said.
