How to Sell on Substack Without Becoming "That" Internet Marketer

Most creators either avoid selling or turn every conversation into a sales funnel. There's a better way.

Do you ever worry that selling on Substack will turn you into “that” person?

You know the type.

Every conversation feels like it’s leading somewhere. Every DM has an agenda. Every comment feels like a tactic, not a chance to truly connect. And every piece of content is either showing you how great their life is or reminding you how bad yours will be if you don’t buy.

They don’t make you feel like a friend, or even a person. You feel like prospect #79 in their “Conversation Sales Funnel.”

If you’re anything like me, you probably hate that. I don’t think anyone enjoys getting a DM with a fake compliment, only to be followed by a sales pitch.

But once you decide you don’t want to be “that” person, it’s easy to swing too far in the opposite direction.

You convince yourself that good people don’t think about selling, so you avoid talking about your work and ignore real opportunities because you’re terrified of sounding pushy.

You hope that if you’re helpful and nice enough, clients will somehow appear.

Unfortunately, that’s a very unreliable way to run a business.

I’ve operated from both sides of this equation, and both sucked.

I hated being the internet marketer who optimized every interaction for a sale. But I also hated being the guru-hater who struggled to sell because he was terrified of sounding pushy.

For too long, I thought those were my only options.

Until I realized there was a third.

The Problem with Making Every Conversation a Funnel

A few years ago, I dove into the internet marketing rabbit hole.

My content was going viral, my Twitter account was growing, and I was making decent money with my coaching business.

But I wanted to grow and sell more predictably, so I consumed a ton of content about online business. When I found strategies for selling in the DMs, I got excited.

I learned that I could use conversation scripts to “move people through my funnel.” I’d reach out, say something personal, ask about what they were doing, uncover pain points, transition into my offer, and overcome objections.

And it kinda worked, at least on paper.

I made some sales and knew it could generate reliable income if I stuck with it and kept improving.

But something felt off. I hated doing it every day because it made me feel gross.

I wasn’t asking questions because I genuinely wanted to know the answers. I was asking because I knew the questions would eventually lead to my offer.

Even worse, I wasn’t upfront about why I was reaching out.

That part ate at me.

Even though I genuinely wanted to help people, I couldn’t ignore the fact that I was steering conversations toward a destination they hadn’t chosen.

So I stopped. Unfortunately, I also overcorrected.

Instead of constantly trying to sell, I barely sold at all.

I once noticed that someone had a crappy coaching offer I knew I could help improve. They had even mentioned wanting to work on it, and I still said nothing.

That’s how bad it got.

I went from pushing my offers onto people to protecting myself from feeling uncomfortable. Both approaches were shitty in their own way.

Fortunately, I found another option.

The Problem with Manufacturing Interest

Over time, I found a completely different way to build relationships, find clients, and run my business without treating people like leads.

I stopped trying to create interest that wasn’t already there.

Instead, I started trying to discover whether a real opportunity already existed.

That might sound like a small difference, but I don’t think it is.

When your goal is to manufacture an opportunity, every conversation becomes a puzzle. You start wondering how to steer it, when to transition, how to bring up your coaching, and what you need to say to make the other person interested.

The sale becomes the goal, and the person becomes the path you use to get there.

But when your goal is to discover whether an opportunity already exists, the conversation feels way different.

You’re no longer trying to fit your coaching into someone’s life. You’re trying to understand them. You actually want to know what they’re working on, what they care about, where they’re struggling, and whether there is a legitimate way you can help.

Sometimes your offer is a great way to help them, and sometimes it isn’t.

That’s a completely different mindset, and it profoundly changes the experience people have with you.

The purpose of a conversation isn’t to create a sales opportunity. It’s to discover whether one already exists.

What Happened When I Stopped Trying to Sell

Sometimes, when you stop trying to create a sales opportunity, one appears on its own.

That happened with a friend of mine. We became friends almost entirely through replies and comments. We’d joke around, share each other’s content, and chat in the DMs.

So we decided to get on a Zoom call.

My only agenda was to get to know him better. I definitely wasn’t planning to sell him anything.

We spent most of the call talking about his marriage coaching business because it fascinated me. He explained how it worked, who it helped, what he was building, and where he wanted to take it.

At some point, he asked about me.

I told him about my coaching business and how I was helping clients improve their content, engagement, and offers to generate more leads and sales.

Then he said, “Cool. I’m in.”

I remember laughing and saying, “Haha dude, this isn’t a sales call. I just wanted to connect.”

He said he knew that and appreciated it, but what I described was exactly what he needed.

He didn’t buy from me because I ran him through a funnel.

He bought because I had shown genuine interest in him, there was real trust between us, and I clearly explained my offer when he asked.

I’m not going to pretend conversations always end this way. Most don’t.

The point isn’t that you should become friends with people and wait for them to eventually ask for your coaching. The point is that he trusted what I said about my offer because he already knew the conversation wasn’t designed to sell it to him.

Instead of manufacturing interest, I just gave him enough space to decide whether my offer was actually relevant to him.

How to Promote Yourself Without Being Slimy

Relationship-first selling does not mean sitting around and waiting for people to ask what you sell.

This is where I overcorrected for a long time.

I became so afraid of sounding pushy that I would recognize an obvious opportunity to help someone and still say nothing.

I convinced myself it was more ethical, even though it wasn’t. It was just bad business.

Fortunately, I’ve moved past that.

For example, a friend recently told me she was struggling to find the right offer for her Substack.

I knew I could help her, so I said:

Hey, I’ve been really focused on this lately and can help you find, test, validate, and build an offer that excites you and your audience. Let me know if that interests you and I’ll explain what that could look like.

That was it.

She said sure, we talked, and she became a client.

I wasn’t planning to pitch her. But she described the exact problem I had been working on in my own business, so I acknowledged it and gave her the choice to hear more.

Before, I would have stayed quiet because I didn’t want to seem pushy.

Now I understand that mentioning your offer is not manipulative when there’s a legitimate reason to bring it up and the other person is free to say no.

So, if an opportunity already exists, simply acknowledge it clearly and let them choose where to go from there.

How to Discover Opportunities Without Losing Trust

One of the best ways to discover opportunities is to become curious about the other person.

But it has to be sincere.

If you’re genuinely interested in someone, they’ll usually feel it. And if you’re pretending to be interested just so you can eventually talk about yourself, they’ll feel that too.

People are surprisingly good at sensing an agenda. That’s why I don’t think “be authentic” is very helpful advice on its own.

You can be authentic and still not care about the other person. You can be authentic and still make every conversation about yourself. You can be authentic and still treat people like prospects.

Instead, I think the goal is to become the kind of person who cares more about understanding someone than figuring out how to sell to them.

That’s the kind of person people remember. It’s also the kind of person people trust enough to open up to about what they’re struggling with.

That doesn’t guarantee a sales opportunity.

But it does give you a chance to recognize one when it appears.

Not Every Relationship Needs to Become a Sale

One reason relationship-first selling works is that you stop expecting every valuable relationship to become a sale.

Sometimes helping someone means introducing them to another creator, recommending a book, sharing one of their posts, answering a question, or simply listening.

I’ve had people refer multiple clients to me who never became clients themselves.

One friend I met online has referred three different people to my coaching, and he has never paid me a dollar.

Apparently, he came to know and trust me well enough to tell other people to spend thousands of dollars hiring me.

If I had spent every conversation trying to convert him, I doubt that would have happened.

Some relationships become clients, but others become referrals, collaborations, friendships, or simply good conversations.

When every relationship has to justify itself with a sale, you make all of those outcomes less likely.

My goal is to simply make people glad we spoke. I want them to think, “Dude, Rob is awesome. I’m stoked I met him.”

Honestly, that’s what I’m shooting for. Whether they buy something is secondary.

Ironically, that’s also part of the reason that more opportunities tend to appear.

You Don’t Have to Choose Between Two Bad Options

Too many creators get stuck between two bad options.

They either avoid selling altogether or become the pushy internet marketer who turns every interaction into a sales opportunity.

But I really don’t think you have to choose either of those.

You can genuinely care about people while paying attention to opportunities. You can build relationships without secretly treating everyone like a lead. And when someone describes a problem you truly help solve, you can mention your offer without apologizing.

That was one of the biggest changes I made in my business.

I stopped forcing sales, but I also stopped being scared to sell.

The goal isn’t to stop selling or to sell constantly.

It’s to put the person first, stay aware of where you may be able to help, and let the business conversation happen when it actually makes sense.

-Rob

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If you want to build deeper relationships on Substack and turn them into referrals, collaborations, and clients, here are two ways I can help:

1. DM me where you’re at and what you’re stuck on, and I’ll share what I’d do if I were in your situation.

2. Want help applying this? My coaching program helps creators build genuine relationships that lead to more referrals, collaborations, and clients. Shoot me a DM, and we’ll see if it’s a fit.

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