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The Side Gig (everything you need to start earning on the side)


I originally started “I Will Teach You To Be Rich” as a 1-hour free course that I taught at Stanford. It was never designed to make money. It was just something cool that I wanted to do. When I’d hear friends complaining about money at the dining hall, I’d say, “Hey, you should come attend this class I put together. It’s free, and it takes about an hour, and I’ll show you all the basics of money, banking, budgeting, saving, and investing.” The response was VERY positive. People said, “Wow, that sounds awesome!”

And then they would never show up.

Over 1.5 years, I repeatedly struggled to have anyone show up. I would wonder to myself, “Why am I trying so hard to give people GOOD, FREE information about stuff they really need to know?” I felt like a career counselor, one of the most underappreciated (and hopeless) jobs.

After trying all kinds of strategies to get people to attend, including emailing THEM and trying to coordinate times, I switched approaches. Instead of in-person events, I launched iwillteachyoutoberich.com so people could read it out of the comfort of their own dorm rooms. Later, I learned why this was so successful: People don’t like attending events about money because (1) it makes them feel bad about themselves, (2) the events are usually boring and/or scammy, and (3) people have to publicly admit they don’t know about money.

It was a classic mistake of not understanding my users (substitute “customers” in your business).

Lesson learned: You MUST get into your clients’ heads.

  • What are their fears?
  • What are their hopes?
  • What do they care about most  (Hint: How much it costs is almost never the first priority).

Similarly, once you get in their heads, you learn that the medium in which you serve your clients matters. (Is it an in-person event or a blog or a weekly phone call?) The way you approach your client matters. And how you sell to prospects matters.