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Millennial Money Man
Bobby started Millennial Money Man in . They detail the beginnings of their company in their Starter Story interview: 
Q: How did you get started on Millennial Money Man?
I had a very traditional educational experience and came out of college with $40,000 of student loan debt. I got passionate about personal finance after paying off my debt, and I made some drastic (and slightly embarrassing) moves to destroy my debt in 18 months.
I found myself teaching my students about personal finance -- not enough people are taught these lessons when they’re young. I was maybe the only band director out there who was also teaching kids about credit scores, investing, and loans. They loved it though.
Another major turning point was talking to a mentor of mine about how I wanted more than what my teacher’s salary could afford. (My readers know me for having boujee taste in wine, haha). He told me I would never be able to afford the lifestyle I wanted on a teacher’s salary. He found my pain point and challenged me to do more.
So, I put all of my energy towards paying off my debt and started M$M. It was slow at first, but after earning just $3 in Google Ads revenue, I got the ok from my amazingly supportive wife to quit my teaching job and go at the blogger thing full force. That’s not something I would ever advise, but being debt-free and having solid savings made it feasible for us.
So many of my coworkers told me I was crazy, and that I would be back within a year. That was over 5 years ago. I’m still not tempted to go back.