I used to be embarrassed going out to dinner with my mom. She would make so many awkward requests to the waiters about food modifications or if something was wrong when it came out. I would get extremely uncomfortable.

This lasted for years.

I didn’t understand why she would always do this. I was out to dinner with her when she was visiting me in San Diego and I told her about how I felt. That’s when it all made sense. “Jared, you’re not going to get anything if you don’t ask for it.”

It’s a simple reframe that took me 27 years to realize. A little edge we have in our Jewish culture. We’re not afraid to ask.

But I was.

When I read Noah Kagan’s book Million Dollar Weekend and he talked about developing your “ask muscle.” You need 100s of no’s to get one yes. Sales, dates, promotions, raises. If you don’t ask, you’re not going to get what you want. No subtle hint dropping of suggestions just ask the dang question.

Get comfortable being told no.

I tell myself this every time I catch myself getting cold feet. What’s the worst that can happen? I tell myself “you’re not going to die.” Get comfortable with rejection, it’s going to happen in life. Whether you like it or not.

What if they say yes? Then you get what you want! Isn’t that such a great feeling?

The thing is, most people don’t get what they want because they don’t ask for it. They just wish for it, they drop “suggestions” and hope someone picks up on it. Don’t hope for something, make it happen. This can apply to business, or life.

“Getting money is not a matter of literally getting it. It’s a matter of RECEIVING IT, which can happen only after one asks for it.” - Noah Kagan

When I launched my first product for my first company. We had over 300 people on our email list that said they were initially interested in what we were working on. I was extremely confident that we were going to quickly fill up our goal of 3 sign ups.

We fired out our launch email. I got a total of 6 sales calls lined up to get people to convert. Everyone was stoked about what we were doing.

I jump on my first sales call. Explained our program and everything the customer would get. He loved it. I asked him to pay. Guess what happened next?

He gawked at the price. I got a big fat NO.

It sucked. Being rejected is no fun. It never will be. That week I got rejected by 4 more people, and 5 over email. Thats 10 total. I took their feedback for why they thought the program wasn’t worth it. I asked them, “what would make this a no brainer for you, why were you interested in this in the first place?”

That’s when you shut up and listen.

I came to realized that everyone was interested in this for different reasons. They didn’t want the entire program, just certain parts and features. We readjusted our product into three different tiers. All priced at three different levels.

I had three more sales calls that week. 2 were extremely interested but the timing didn’t line up for them. 2 more no’s. But I got one yes. It felt amazing. I had to work through 13 no’s to get 1 yes.

Now I’ve got a paying customer.

I kept asking.

Noah laid it out beautifully:

Always be asking

The trick is to desensitize yourself to the pain of rejections. You need to keep exposing yourself to it. Embrace the discomfort, maybe even actively seek it out.

Who is the type of person to start a successful business or just get what they want?

• Someone who asks for what they want

• If you want a new job at a new company, you have to reach out and ask for it

• If you want more money from your boss, you have to ask for a raise (probably a couple times)

• If you are selling something, you have to ask for someone to buy it

• If you want someone to treat you differently, you have to ask them

Be persistent

If you believe that almost every no you get will eventually become as yes. Persistence will reveal most noes are actually a “not now”

Follow-up, Follow-up, Follow-up!

I’m doing this right now with companies I find interesting. Just because I want to be helpful.

I know they’re reading it, so I keep checking in 🥲😉

Its beens shown that if you initially get a no, your follow-up ask is twice as likely to be a yes.

It’s going to be uncomfortable at first. It likely always will be. You start to get comfortable with that feeling of discomfort.

You can do this. I believe in you 🫶🏻🖤