How I "Slid into the DMs" of One of My Favorite Authors

What is something you’ve always wanted to do but haven’t done yet because of your self-doubt, fear of failure, or your constant search for the perfect moment?

This is a story of how I “slid into the DMs” of my favorite personal finance author to pitch my videography idea and services to him.

Back in 2019, I wanted to contribute my videography skills for someone I admired to help share their message in new ways. Whether it is an author, a YouTube influencer, or some startup founder who is working on a mission I believe in, I wanted to extend their reach.

An opportunity arises

When shelter-in-place started in the U.S. back in March 2020, Ramit Sethi, the author of the personal finance book, I Will Teach You to Be Rich, started doing Instagram Live videos every evening with a Q&A on personal finance and life-related questions. These live sessions were 1-hour long and it was difficult to watch the whole thing if you were busy.

I remembered hearing Ramit in a podcast talk about “The Briefcase Technique,” a method to impress someone you’re attempting to win business from. In this technique, you come fully prepared -- more than what the interviewer expects. As you’re meeting with your interviewer, you pull out a document from your “briefcase” and showcase your research on what improvements they can work on and how you’d do it.

This shows your preparedness, proactiveness, and an example of how you work. Whether they agree or not with all of your specific suggestions, they may be impressed enough to hire you.

I basically did that!

I first reached out to him on Instagram and shared the high-level ideas of what I’d improve on. He responds with a piqued interest in my proposal and asks for details. I shared details of 2 ideas I had and he showed interest in one of them. I suggested that he creates short video highlights of his hour-long IG Live videos to allow his audience to get the best tips and promote more people to attend the live sessions.

He asks me to send an email of the proposal!

The Briefcase Technique 💼

I not only sent him an email of the proposal, but I also sent a quick demo of what I would do for him with an IG video he filmed that day. With a 24-hour turnaround time, I used a video he filmed the day before and created an Instagram clip to showcase my skills, because, you know… it’s better to show and not just tell!

I had self-doubt in my own abilities 😨

The scary part was asking him to judge my videography skills. I already knew he liked the idea, but now it was all about whether he would be willing to hire me to do the job for him.

For that particular situation, the worst thing would have been Ramit ghosting me and nothing happens. I spent only a few hours creating a demo video to showcase my talents, but the experience was worth it.

The lesson learned here is to ask yourself, “Why not try? What’s the worst that could happen?” It’s not about whether or not you were successful in your attempt. It’s about whether or not you tried. 🔑

The fear of failure and caring about what others may think of you can be self-sabotaging. These self-sabotaging mindsets are what prevents you from going out of your comfort zone and taking on challenging opportunities. The more you let these self-sabotaging mindsets paralyze you, the greater the effects it will have on you in the future.

And it goes the other way as well.

The more you overcome your self-sabotaging mindsets, the less the effects it will have on you in the future.


I learned a lot

I learned a lot about myself and what I can handle, I challenged myself into an uncomfortable situation by reaching out to someone that seemed out of my reach, and it’s allowed me to gain more confidence in myself to reach out to others like him in the future.

What happened next was not what you’d expect, and it was not how I expected it to happen as well. But you’ll have to wait for next week’s email as it goes into another topic of intentional living! 😃

What has a self-sabotaging mindset paralyzed you from doing?