How Katelyn Bourgoin Turned 300 Failed Interviews Into A $1 Million Newsletter

Katelyn Bourgoin interviewed 300 people before her startup failed.

VC-backed, she had talked to her target customers, asked them what they wanted and built exactly what they described.

But they didn’t buy it.

Three hundred conversations. The right audience. The product they asked for.

And yet, nothing.

The company collapsed, and it took years before she understood why.

She’d asked the same question in every interview, and it had been leading her in the wrong direction the whole time.

Today she runs a newsletter. 63,000 subscribers. Roughly $1 million in 2024 – around $16 per subscriber – while the industry average hovers between $1 and $5.

She named it after the question she should have been asking all along.

The Wrong Question, Asked 300 Times

Before Vendeve, Katelyn had already built and sold a restaurant consulting business.

She’d launched a branding agency called RedRiot that landed clients like Target and Holiday Inn. Marketing was where she excelled.

So when she started Vendeve, a business network for women entrepreneurs, she applied everything she knew.

She talked to her target market. Ran interviews. Collected feedback. The press loved it and investors backed it. Forbes called it “the next LinkedIn for women.”

“On the outside things looked like they were going great,” she said later. “On the inside, things were not going great.”

She’d asked 300 people what they wanted. They told her. She built it. When it came time to pay, they disappeared. The company burned through its runway and collapsed.

After the failure, she took consulting work with startups.

She sat in rooms with founding teams who had personas, surveys, and interview transcripts, but she kept seeing the same gap she’d lived through.

They’d done their customer research, but they still couldn’t explain why anyone would buy.

Teams with answers to “what do you want” and no understanding of what actually triggered a purchase.

The insight from her own failure started to take shape.

What do you want? gets answers. People will tell you all day.

But those answers don’t predict buying behavior – what a person would actually put down their hard-earned money for.

Why do you buy? That’s different.

It’s about psychology. Triggers. The moment someone moves from interested to committed and takes action.

The academic research on buyer psychology existed, it just wasn’t written for practitioners.

So Katelyn started translating these otherwise dry academic papers into frameworks marketers could use.

She called it “science, not guru B.S.” The newsletter followed. She named it after the question: Why We Buy.

The positioning was set. Now came the architecture.

Three Revenue Layers, One Audience

She decided to launch the newsletter twice a week.

Each issue would break down a cognitive bias or buying trigger, showing how it worked inside real campaigns.

Academic research would translate into something a marketing team could apply immediately.

The audience that gathered to read it: B2B marketers, SaaS operators and founders. People inside companies with budgets for training, tools, and consulting.

The kind of subscribers sponsors pay premium rates to reach.

Naturally then, sponsorships became the first revenue layer.

By 2024, sponsorships generated roughly $300,000 annually.

That was income that arrived whether she published new products or not, a great safety net for any business to operate with and one that could provide a little breathing room when needed.

The second layer came through collaboration.

She partnered with Phill Agnew, host of the Nudge podcast with 350,000 listeners, to create Wallet-Opening Words, a $129 product packaging copywriting techniques backed by behavioral science.

She then partnered with Neal O’Grady from Demand Curve, which had 97,000 newsletter subscribers, to build Unignorable, a course on positioning and visibility.

Each collaboration meant launching to two audiences at once – double the impact.

The result? Unignorable crossed $1 million in total revenue.

The third layer was services, priced to filter out unqualified buyers.

By 2024, her lowest offer was $5,000.

For a startup founder, that’s a stretch, but for a marketing team at an established company with allocated training budgets, it’s a line item.

Her clients collectively generate $3.4 billion in annual revenue. At that level, a messaging improvement that lifts conversion even slightly, pays for the engagement many times over.

All three revenue layers – newseletter sponsorships, collaborations and services – drew from the same source: an audience that cared about buyer psychology and had money to spend to solve it.

The newsletter built trust.

Sponsorships monetize attention.

Products monetize implementation.

Services monetize outcomes.

Learning from earlier ventures, Katelyn also knew she had to run lean and protect her own time.

Contractors only, no agency work, live cohorts replaced by self-paced. The structure allows for  work that scales: content and partnerships.

The Flywheel That Was Four Years In The Making

Katelyn’s positioning anchors everything.

“Why do people buy” is a question that never gets fully answered.

Consumer trends shift. Platforms change. New products launch. But the psychology underneath buying behavior stays stable.

A newsletter about TikTok tactics has a shelf life, but a newsletter about buyer psychology stays relevant as long as people keep making purchases.

That question attracts a specific audience.

The newsletter delivers on the positioning promise twice a week.

Frameworks they can use. Research made practical.

Over months and years, that consistency builds trust.

Subscribers forward issues to colleagues. They test the ideas in their own campaigns and they see results.

By the time a product launches, the audience already believes in the method.

They’ve watched it work.

When they land on her sales page, it confirms what they already think.

That’s why her revenue per subscriber runs three to five times the industry average.

The list isn’t unusually large, but the trust runs unusually deep. Each piece feeds the next. The question attracts the audience. The audience makes sponsorships valuable.

Consistent delivery builds trust and trust makes products convert and premium pricing possible.

It’s one big flywheel rather than four separate advantages.

This wasn’t built overnight though. The newsletter started in 2020.

The $1 million came in 2024.

Four years of showing up twice a week, refining frameworks, and letting trust compound.

What You Can Build From the Same Question

The newsletter, the partnerships, the $5,000 price floor, they all came from her specific situation. The principles underneath can be applied at any level though.

To start with, she found a market with perpetual demand.

Buyer psychology stays relevant because buying behavior keeps shifting. New platforms, new products, new contexts.

The fundamentals hold, but the applications keep changing.

Any market where the landscape shifts regularly creates ongoing demand for someone who can make sense of it.

Tax strategy changes with legislation. Software tools evolve. Health research updates.

The subject matter that keeps continually changing and evolving is subject matter people keep paying to understand.

She built an audience with allocated budgets.

Marketers at established companies have line items for training and consulting.

A $5,000 engagement gets approved through a purchase order.

That same product or service being sold to start-ups or lean entrepreneurs often meets price resistance at a fraction of that cost.

Ironically though, many creators start by serving people like themselves – entrepreneurs, freelancers, small business owners, and businesses at this level often have extremely tight budgets.

The ones who scale often shift toward corporate clients or established businesses that can pay without giving it a second thought.

She used collaboration to reach audiences that didn’t know her yet.

Every collaboration she created launched to two subscriber bases at once.

This principle can happen at any level.

Two creators with small lists can combine reach the same way. The key is complementary audiences that would value the work of the other, and a shared stake in making the product work.

She let years of proof justify the pricing.

The $5,000 floor came after documenting results with clients that generated billions in revenue.

At that scale, a small improvement in conversion could cover the fee many times over.

Not every business can start out charging this amount, but premium pricing makes sense when the buyer can measure the return and the return is significant.

For Katelyn though, it was more than just a combination of these four elements that brought her success, it was being willing to look past what buyers said they wanted and look deeply at what made buyers actually take action.

Ironically, it was this insight itself that helped her create the business that she has today.