The shortcut and shortfall of selling to your peers

"If there is one thing I have done right, it's not selling to my peers." - Sam Shepler, Testimonial Hero (opens in a new tab)

This simple statement from a discussion with my friend, Sam, had a profound impact on me. For years, I had fallen into the trap of selling and marketing to my peers. And it wasn't until this simple sentence was said that I realized it.

Beyond myself, I see this trend among many entrepreneurs. So in this article, I will dive more into this concept and how it has played out in Lead Cookie (opens in a new tab) and Content Allies (opens in a new tab).

What I mean by "selling to your peers"

When I talk about "selling to your peers," I am talking about selling to other entrepreneurs like you.

If you are a programmer, it's trying to sell to other solo programmers.
If you are a marketer, it's trying to sell to other solo marketers.
If you are a small business owner, it's trying to sell to people just like you.

Counter that with Sam at Testimonial Hero (opens in a new tab). I am a peer to Sam. We are both small business owners with businesses of similar size. While Lead Cookie may be a fit for Testimonial Hero, it's not the same when you flip it around.

Why we sell to our peers

It's easy.
They are right there.
You don't have to work as hard.
You understand them more.
They trust you more.
It's not as scary as stepping outside of your comfort zone.

Your first sales will almost certainly be to someone in your network... which creates a circle of validation of believing that those people are your best customer profile.

There are many reasons we sell to our peers. And it's not a bad place to start for many entrepreneurs. But the problem occurs when you stay there...

How Sam nailed not selling to his peers

Take a look at Testimonial Hero's site (opens in a new tab) and what you will find is countless testimonials from large enterprise companies. A few small businesses have made their way into the mix, but by and large, Sam is working outside of his social circle. He is marketing and selling up the ladder to bigger companies with bigger budgets.

How I made the "peer mistake" along with many others

For a majority of Lead Cookie's life, we have focused on small businesses. My advisor, Alex McClafferty (opens in a new tab), consistently pushed me to try to go upmarket with this business. While I did try to go up market with Lead Cookie, we actually did find a better product market fit at the small and medium sized business. We have found lots of challenges dealing with larger companies due to the grey hat nature of our service, but saw great success at the small business level.

So for Lead Cookie's sake... the peer mistake was kind of a good thing.

But where the mistake hit me hard was when I launched Content Allies (opens in a new tab). Initially, I went out with the same exact focus and angle as Lead Cookie. I tried to serve the same audience of small business owners like myself. I initially sold the service to many friends and peers.

And then churn happened...

Peer after peer churned off of Content Allies.
It was too expensive.
They could write themselves.
Or they knew they could get writing cheaper elsewhere.

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Jake’s historical account, summarized from this article. These results describe his experience and are not a performance forecast.

As a result, the first 6-9 months of Content Allies were filled with painstaking misery of disappointed clients and lots of wasted sales calls.

Recognizing the peer mistake, and shifting from it

When I started realizing the mistake I was making by selling to my peers and others like me, I made a shift in Content Allies.

Instead of selling to any agency or consultant who came along, I got very clear on who my target market was.

At Content Allies, we target:

• Consultants or consulting firms who are generating over $250k of personal income per year
• They are experts in their field.
• Doing high-quality work has built them a business on word-of-mouth and referrals.
• They have done little to no marketing, but recognize they need something to accelerate their word-of-mouth engine.

While I may have done my share of consulting in the past, it was at a small level. I've never operated at a high-level that many of our ideal clients do.

And when I look around my social circle, I don't have many people like this in my network.
These are not my peers, but instead our ideal clients.

There is probably still room for me to go upmarket more... but that will come in time.

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The approach described in this article, shown as a visual guide.

How I made the shift

While I would love to say there is some amazing turning point or tactical thing I did to shift this, that isn't the case. In reality, this was more a recognization of the problem in my customer base.

I first had to recognize who my ideal customer actually was.
Then I had to accept that a majority of my peer group was NOT a good fit.

This sounds easy at first, but it's kind of awkward when a lot of your peers start reaching out and asking about your business... You want to sell to them. You want to offer it. But you know it will fail.

It took me a while to accept this.
For a while, I still took the sales calls.

But, eventually, I realized that they would never pay our rates, or they would sign up and then churn because they were not our ideal persona.

...and to this day, I still get bad leads from my peers and network all the time.
Sure, they could use content... but just not from us.

How I see the "peer problem" playing out in others

This problem shows up in entrepreneurs all across the board. The other day I was having coffee with a software founder. He had worked for several large enterprises and identified a pretty expensive problem... It was a pretty genius and high ROI product idea he had. It saved the past companies he worked for almost $100k per year, year after year...

Then he said, "But I'm going to try to sell it to small business owners for a couple hundred dollars."

His justification is that he didn't want to deal with corporate sales. He wanted to sell it to others like himself and do the volume play...

This "fear" of going upmarket is a constant challenge. People are afraid of corporate, afraid of bigger companies.

Sure, it's easier to sell to small businesses, but SMB's come with their own set of problems.

Go where your service is most valuable

The software entrepreneur I mentioned in the previous section... he had a product that could save an enterprise $100k+ per year on an ongoing basis.
Or it could save a small business owner about $1k per year... if they had the resources to even implement it.

Sam and Testimonial Hero (opens in a new tab)...
An enterprise may use one of his videos to arm their sales team, increase website conversions, or drive more leads. Any of which could lead to hundreds of thousands in new revenue.
Or he could sell it to a small business owner who might see a $10k-50k annual bump in sales from the marketing materials.

The value of your service depends upon who you are delivering it to.
Go where your service is most valuable.

A year after this essay, in a March 2021 episode of my podcast, I made the same point about B2B podcasts: the biggest mistake most people made when launching one was building it "focused on their peers and not their prospects," and I admitted I was a culprit. My own show had started out interviewing fellow freelancers. It was good networking, but it led to few business opportunities.

In my May 2025 conversation with Alex McClafferty (opens in a new tab), the advisor who pushed me to go up market, I said Content Allies was where we really did. I had to learn enterprise sales, which I called "a different world." Once we had our first large client, the next ones came more easily. The larger clients helped us raise our rates and reach a healthier margin. We had once served independent coaches; that was no longer our market. We kept a mix of small, mid-market and enterprise clients, because enterprise budgets swing harder with the economy.