Day 2: I Picked the Wrong Customer Before I Picked the Right Problem
For this 30-day shipping experiment, I decided to explore a product around newsletter creator sponsorship and growth operations
Yesterday I picked the lane.
For this 30-day shipping experiment, I decided to explore a product around newsletter creator sponsorship and growth operations.
On paper, it made sense.
Newsletter creators are growing real businesses. Sponsorships are one of the cleanest ways to monetize an audience. The tooling is still messy. Most creators are stitching together Substack, beehiiv, Passionfroot, Paved, spreadsheets, Stripe links, email templates, and manual follow-up.
So my first instinct was obvious:
Build something that helps newsletter operators manage sponsorships better.
A sponsorship CRM.
A booking workflow.
A sponsor operations dashboard.
A way to track assets, payments, scheduling, approvals, and reporting.
That sounded useful.
But Day 2 reminded me why “sounds useful” is dangerous.
Because the first version of the customer I picked was wrong.
My first mistake
I started by looking at successful newsletter operators.
People with sponsor pages.
People already selling ads.
People with polished media kits.
People with clear packages, pricing, and sponsor workflows.
They looked like the perfect market.
But then I asked the question I should have asked earlier:
Do these people actually have the problem?
And the answer was probably no.
At least not the urgent version of it.
The more I looked, the more obvious it became that many of the most visible newsletter operators had already solved the core problem. They had inbound interest, sponsor pages, repeat advertisers, agencies, or enough reputation that sponsor ops was more of an optimization problem than a painful daily wound.
They might be great expert interviews.
But they are not the best early customer discovery targets.
That distinction matters.
An expert can explain how the market works.
A customer in pain can tell you what they are already trying, where it breaks, and what they might pay to fix.
I was mixing those two up.
The real pain moved
The first idea was:
Newsletter creators need help managing sponsors.
The better version became:
Newsletter creators need help finding, pricing, and closing the right sponsors in the first place.
That is a very different product.
A CRM helps once you have sponsor demand.
A booking system helps once people are trying to book slots.
A reporting dashboard helps once campaigns are running.
But most newsletter creators are stuck earlier.
They are asking:
Who should I pitch?
Am I big enough to get sponsors?
What should I charge?
Should I use Paved, beehiiv Ads, Passionfroot, cold outreach, or wait for inbound?
Why do I have subscribers but no sponsor pipeline?
How do I get the first sponsor without looking desperate or guessing?
That is a pain.
Not “my sponsor workflow is too complicated.”
More like:
“I have an audience, but I don’t know how to turn that audience into direct sponsor revenue.”
And that problem shows up across a wide range of newsletter sizes.
Tiny lists with a few hundred subscribers are asking if they are sponsor-ready.
Newsletters around 1,000 to 3,000 subscribers are asking how to land their first sponsor.
Operators with 8,000, 20,000, 65,000, and even 200,000 subscribers are still asking how to get consistent direct sponsors.
That was the part that surprised me.
Audience size helps, but it does not automatically create a sponsor pipeline.
My sharper ICP
So I changed the ICP.
The first ICP was too polished:
Founder-led B2B newsletter operators already monetizing with sponsor slots.
The revised ICP is much better:
Niche newsletter operators with 1,000 to 100,000 subscribers who want direct sponsorship revenue but do not yet have a reliable sponsor pipeline, and whose founder or editor personally handles sponsor outreach, pricing, and follow-up.
That is tighter.
It focuses on people who are still doing the work themselves.
They do not need enterprise ad ops software.
They do not need another empty profile page on a marketplace.
They do not need a fancy dashboard for sponsor volume they do not have yet.
They need the next sponsor.
Or the first sponsor.
Or a believable answer to: “Who should I even contact?”
What the research showed
The clearest pattern from the research was that creators are not mainly complaining about managing too many sponsors.
They are complaining about not knowing how to get sponsors.
Some are already listed on marketplaces and still getting nothing.
Some have good open rates but no direct advertiser relationships.
Some know their audience should be valuable, but they do not know which brands to pitch.
Some are paying monthly newsletter costs and making zero dollars back.
Some are unsure if they are too small.
Some are afraid of charging too much.
Some are probably charging too little.
The second pattern is that pricing and acquisition are connected.
You cannot confidently pitch a sponsor if you do not know what you are selling.
A newsletter creator needs more than a list of companies.
They need to know:
Why this company is a fit.
What offer to lead with.
Which buyer to contact.
What placement to sell.
What proof to include.
What price to test.
What to say in the first message.
How to follow up without sounding generic.
That means the MVP should probably not be software first.
At least not yet.
The MVP changed
The first product idea was some kind of sponsor management tool.
The better wedge is…
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