I watched my childhood best friend become a millionaire while I stayed broke-here's what nobody tells you about that experience - Silicon Canals

"Matt and I started from the same place. Same middle-class neighborhood, same public schools, same dreams of making it big someday. We'd spend hours in his garage talking about the companies we'd build, the problems we'd solve, the money we'd make. The difference? He actually did it. Last month, I scrolled through Instagram and saw him closing on his third investment property. Three months before that, it was the Tesla. Six months before that, the startup exit that set him up for life."

"When Matt first started making real money, we'd still grab beers every Friday. But slowly, almost imperceptibly, our conversations started diverging. He'd mention flying business class to a conference, then catch himself and downplay it. I'd complain about my rent going up, then feel weird about bringing up money problems to someone who just dropped sixty grand on a watch. It wasn't that he became arrogant or I became bitter."

Two people with identical upbringings followed divergent paths when one achieved rapid financial success while the other struggled. The successful friend celebrated investments, luxury purchases, and a lucrative startup exit, while the other remained renting and anxious about money. As incomes diverged, conversations shifted: wins were downplayed and struggles were withheld to avoid awkwardness. The friendship did not end but became constrained by self-censorship and unspoken tension. Differences in financial reality made everyday topics feel risky and intensified feelings of failure after setbacks, including a collapsed second startup that cost investor money and confidence.

Read at Silicon Canals