Most of us take the safe road. We go to college, get a job, and spend the next 30 years hoping our employer doesn't one day decide we're suddenly redundant. I know this path well because I walked it for 13 years before I finally worked up the nerve to do my own thing in […]
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Life is hard if you want to outperform average. To reach a USTA 5.0 level in tennis takes an endless amount of practice. To get promoted to Managing Director in banking, you first have to survive a decade of 70+ hour weeks just for a shot. And if you want to be your own boss and build […]
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Part of the reason I've been writing about distribution and the importance of eventually betting on yourself was to gear myself up for Y Combinator Demo Day. For those unfamiliar, YC is the largest and arguably the best startup accelerator in the world. And it happens to be based in my backyard in San Francisco. […]
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After graduating from Berkeley's MBA program part-time in 2006, I wanted to start Financial Samurai. But even after taking entrepreneurship, marketing, and finance courses, everything I needed to launch a business, I didn't. My excuse was that my firm, Credit Suisse, had paid for 80% of my MBA education, and I felt obligated to repay […]
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Back in 2012, the year I left banking, I had a choice: build a lifestyle business or build a venture-backed company. I chose the lifestyle business. After 13 years in equities I was burned out and just wanted to be free to enjoy the FIRE lifestyle. Writing and tinkering 15 to 20 hours a week […]
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To outperform the masses, we must take more risk than average. One way to do so is to invest in venture capital. However, venture capital is a form of patient capital, and patient capital requires time. That is the one resource older investors have less and less of. At 50 in mid-2027, I'm entering the […]
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