How To Sell On Instagram Stories In 2021

by | May 8, 2021

Watch the whole video here

We’re in 2021 and you’re still not using Instagram Stories to sell your products? You might as well quit now!

I’m here to talk about the best way to sell your product or service through Instagram Stories. Without being spammy and without posting 5 times every day.

Sound good…?

If you want to know how to sell on Instagram stories in 2021, then continue reading!

I am not gonna tell you how to spam people, because I don’t do that.

But I am going to tell you how to sell… Specifically within Instagram stories.

Selling online is a bit of a funny thing, especially given how much spam is out there. And if you’re anything like me and anything like my Instagram account, I get messaged all the time by people who basically say:

“Hi, Dan, buy my thing, buy my thing, buy my thing.”

And we’re not talking about the webcam type stuff that guys always get sent messages about.

I’m not talking about that!

I’m talking about people trying to sell me coaching. And trying to sell me graphic design. And video editing. And explainer videos.

You name it. People drop into my DMs all the time trying to sell me stuff!

But none of them understand how to actually sell….!

So we will talking about that now…

How to sell has not changed in millennia.

Whether you’re talking about a cave person who’s trying to sell a leg of a wooly mammoth, in exchange for a club.

Or whatever the cave people traded back in the day…? I don’t know, I’m not a cave person, ha!

But the methods and the psychology behind it hasn’t changed for a long time, right?

We as humans.. We know how to sell, because we do it all the time.

Basically, what you’ve gotta do is try to pick up someone in a bar.

This is how I teach sales to my clients.

If you look at it through that lens, selling on Instagram stories becomes actually quite easy to do!

Because if you go into a bar, you see someone who you find appealing and you want to interact with them…

Do you go straight up to that person, grab them by the hand and say, “Hi, I am awesome, let’s go.”

Some people do. Some people get success with that.

But let’s face it. In 99% of the cases, that doesn’t work!

In most of those cases, it deserves a slap or a punch in the face.

And we as humans, we don’t like that kind of approach anyway…

But alternatively, if you go into that bar and you see someone who’s appealing to you.

You get their attention. You initiate that engagement.

You get a nod. A wink. A smile. Or a hair flick (if you have hair… I don’t have hair but if you did have hair, you could flick it! ha).

That’s engagement, right?

You then start a conversation. And you say:

“Hi, what’s a girl like you doing in a place like this?”.


“Do you come here often?”

“What do you think of the band?”

Depending on what’s going on (contextually to the environment), you start a conversation.

You then seek permission to deepen that conversation.

You don’t just sit down in a booth, with someone sat there with their friends.. And just join them for dinner. Talking about yourself…

Cause that’s weird, right?!

But if you say:

“Do you mind if I join you because it would be nice to get to know you more?”

If the answer is no, they go on a metaphorical nurturing pile.

The email list. The Google Pixel. The Facebook Pixel. A retargeting campaign…

We’re talking marketing terminology there.

But in generally speaking, you need to have that permission.

And if the answer is no, don’t then sit down anyway. Because that makes you a bit of a d*ck.

But if the answer is yes, then you sit down.

Then all you need to do is to connect emotionally. Connect logically. And then make an ask!

Connecting emotionally would be sharing your thoughts or your feelings about something.

Sharing a story. Asking the person about themselves. And then connecting and resonating with something they’ve said.

You’re connecting on an emotional level…

Now, people buy with emotion and justify with logic.

When you buy with emotion and justify with logic, you make the emotional decision… But that decision is kind of up in the air in terms of your psychology.

You need something to anchor it to!

So we always need facts and figures….

“My name is Dan. I am 38. I am a father of two. I’m married”.

Obviously I’m not trying to pick up someone in a bar here, because I’m married ha.

But logical justifications are what’s needed…

You’ve got to have those anchors, to latch onto the emotional feeling that you’ve got inside yourself.

So then it’s just ‘the ask’ that remains!

So let’s take this into Instagram stories.

You’re going through your IG Stories…

And you’re flicking through the hashtags or flicking through your connections…

Or you’re going through the explore page. And you find a story that you like or that you resonate with.

Drop a DM in the actual story and just say:

“Hi, really loved your thoughts on this, great work.”


“Hi, really loved your thoughts on this, why don’t you think about X?”

So you’ve engaged, right?

And you’re starting a conversation.

If the person comes back and just says, “Thanks”.

That’s basically a “thanks, but no, thanks”.

If they come back. They share. And you start a conversation…

Then you can deepen that conversation deeper!

“It would be nice to get to know you better.”


“Do you wanna jump on a call at some point? It’d be lovely to discuss more your thoughts on X.”

You deepen that conversation. You’re asking permission to go further in that conversation.

And when you go further into that conversation, you are connecting emotionally, connecting logically and then making an ask.

That ‘ask’ may be a sale…

It may be a sign up to an event.

It may be meeting up at a networking event.

Maybe going to a conference…?

A joint venture.

It may be a collaboration you want to do on YouTube or elsewhere.

So how we actually sell and how we actually buy, as you can see…

That it hasn’t changed in a long time, right?

This example is with Instagram stories…

The same method works for Facebook.

The same method works on LinkedIn.

The same method works on YouTube.

Through this content, I am engaging with you.

I am going to ask you if you found this interesting…?

If it’s resonating in your brain?

Please Subscribe to my YouTube Channel if you haven’t really done so….

I’m making an ask.

I’m connecting emotionally.

I’m connecting logically.

I shared information with you through this content.

I did exactly what I’m explaining right now.

This is me selling to you.

I’m a business coach and a mentor.

If you want to work with me directly, then you’re welcome to do so…

But remember, an ask doesn’t have to be a commercial sale.

It can be sign up to an email list.

Subscribe to my channel.

Give this video a like on YouTube if you found value in it…


Selling isn’t anything new.

Whether you’re in 2021 or 2000 BC, it has not changed and I don’t think that human nature will change that much in the foreseeable future.

So if you want to deepen your understanding of how to actually sell online…

How to start, grow and scale your business, whether on YouTube or Instagram. Or Facebook or LinkedIn. Or wherever…

More content like this one are shared on my YouTube channel to help you start, grow and scale your business online.

If you’re a creative entrepreneur, this channel is for you…

So let’s go down that rabbit hole together, shall we?

Dan Holloway
Business Coach & Mentor
to Creative Entrepreneurs
Founder, The #DanKnows Vault


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