I think a lot of people see me as a very conservative investor. I preach paying off debt, living below your means, and investing early and often often in low fee index funds. And I strongly believe in that. It’s the bedrock on what I’ve been doing for my entire adult life.

But on top of that foundation, I’ve also decided to take a few big risks. One of those risks was turning down a lucrative full time job offer from Microsoft as I was graduating college, and instead starting my own company. I ended up selling that company at the age of 34 for over $5M. This is the first picture I have of that journey. It’s taken in my basement apartment bedroom when I was 22 years old. I was frugal even back then. My desktop was my parent’s old coffee table, that I took off the legs and stacked on cinder blocks. I’m pretty sure I picked up that second monitor for free when someone was throwing it away. My office is set up in my bedroom because I shared the rest of the apartment with my roommate. Pretty modest accommodations compared to how I would have been welcomed at Microsoft.

But despite the frugality, I decided to take a risk. No doubt, I was in a position of privilege to be able to do that. I graduated from college debt free thanks to my parents saving for tuition, a track scholarship, working during the summers (and sometimes the school year), and teaching in grad school. If I failed, I was pretty confident I would be able to get a job, and had a network of friends and family who wouldn’t let me become homeless. But still I had to turn down the sure thing. I had to risk a public failure. It was scary to consider being seen as the kid who tried and failed and went crawling back to corporate America.

Risk are scary because they’re not sure bets. But they’re also the only way to realize the really big wins. If you want to be a millionaire, live below your means and buy and hold index funds. If you want to be a billionaire, you have to take some risks.

As always, reminding you to build wealth by following the two PFC rules: 1.) Live below your means and 2.) Invest early and often.

-Jeremy

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