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

Becoming rich does not always bring happiness. Self-made millionaire Lin Kawaoka shares how financial success made him feel isolated and disconnected from friends and co-workers. He grew up cautious with money, and built a real estate empire, but found it difficult to connect with people who didn’t share his mindset — until he joined communities of like-minded investors.

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

Growing up in a humble family in Hawaii taught him to be careful with money. After studying engineering 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 surpassed the $1 million price tag, 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 speaking to Business Insider.

Conversations with old friends became awkward, and coworkers didn’t share his priorities. Many of his friends still view religion as risky, while he views it as a tool.

For fear 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 “speaked his language.” They were not affected by his income, but were interested in the ideas. Later, he joined groups such as the Entrepreneurship Organization (EO) and Visage, where money and ambition were not taboo topics.

Meeting the first generation of wealth builders gave him a sense of belonging. “More than anything, I felt relieved — relieved that I wasn’t a weirdo, and relieved that I wasn’t the only one thinking about tax efficiency, estate planning, and building multigenerational wealth in my 30s,” he said.

He also discovered that he was not an introvert at all. “I still remember a dinner with a small group of fellow real estate investors. The conversation was smooth, deep, and lively. No one backed down. It was the first time I felt truly understood—and I didn’t want the night to end,” he recalls.

Today, Kawaoka rarely talks about money with old friends. Instead, he spends time with people who share his mindset. “It’s not about showing it off; it’s just a helpful sign,” he added. “Because when you meet someone else who built it from scratch, you tend to speak the same language — even before you say a word.”