'Getting rich made me invisible': Investor reveals loneliness behind financial success

Becoming wealthy doesn’t always bring happiness. Lane Kawaoka, a self-made millionaire, shares how financial success left him feeling isolated and disconnected from friends and coworkers. Growing up cautious with money, he built a real estate empire, but found it difficult to relate to people who didn’t share his mindset — until he joined communities of like-minded investors.

Becoming rich isn’t always the fairytale ending people imagine — sometimes, it can feel lonely. Lane Kawaoka, a US-based investor and self-made millionaire, says his path to financial success came with an unexpected side effect, which is isolation.

Growing up in a modest Hawaiian household taught him to be cautious with money. After studying engineering and landing 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 mark — but instead of feeling accomplished, he felt distant. “It gets lonely. Not because of the money, but because you feel like you can't talk about it,” he said while talking to Business Insider.

Conversations with old friends grew awkward, and coworkers didn’t share his priorities. Many of his friends still saw debt as risky, while he viewed it as a tool.

Afraid of sounding boastful or being seen as the “rich friend,” he stopped discussing his goals. “It gets to a point where you stop talking about your goals,” he said, describing how he began to feel invisible — “a lone wolf” among people still focused on 401(k) plans.

Things changed in 2016 when he joined a real estate mastermind group. For the first time, he met people who “spoke his language.” They weren’t impressed by his income — they cared about ideas. Later, he joined groups like Entrepreneurs’ Organization (EO) and Vistage, where money and ambition weren’t taboo topics.

Meeting other first-generation wealth builders gave him a sense of belonging. “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 also discovered he wasn’t introverted at all. “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 recalled.

Today, Kawaoka rarely talks about money with old friends. Instead, he spends time with people who share his mindset. “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 added.