why + when you should be annoying

and what it has to do with Shark Tank

Jennifer Chou
October 06, 2025

Yesterday I woke up to an email:

“We’re getting Mark Cuban (from Shark Tank) in this meeting, sign up today.”

A group I joined earlier this year was trying to get attendees to their Q&A event with Mark Cuban.

Apparently, they sent him a total of…

98 emails!!!

Before he said yes 😅

I know people are busy.

Once, I sent my 5th follow-up email to someone being like “hey…this is the last time I’m following up with you…”

And they ONLY replied to that email.

My coworkers + boss would also always tell me how they appreciated that I never let things slip through the cracks.

But I never realized what an important skill this was until one of my coaching clients shared this story…

When I was promoting my course, I almost gave up.

Seeing low responses to my posts was discouraging…

And my coaching client felt the same.

“People aren’t replying to my questions,” she said. “Maybe they’re just not interested.”

But today, she literally got a DM from someone asking to buy from her.

They literally messaged her “your knowledge and expertise are definitely worth more than the price tag.”

And none of this would’ve been possible if my client stopped “being annoying” and stopped sharing her posts.

It’s about your feelings of self-worth.

Most of the time, you’re not really being annoying.

You just think you are, because you don’t want to be a burden and take up space.

But it might actually hurt your future…

Because following up with people and sharing your whole self confidently

(Including products you create that you’re proud of)

Is actually helping people, in a way.

You just gotta reframe it:

Following up with people by sending 5+ emails = helping them see something important when they’re super busy.
Continuing posting about your product with no responses (yet) = helping potential customers get a solution to their problems.
Sending 98 emails to Mark Cuban = getting him on a Q&A to inspire hundreds of young entrepreneurs.

Think bigger than yourself, and you might find that you actually don’t mind being “annoying” after all.

Til next time,

Jennifer

or to participate.