Jenny.ai: The $20K Misspelling That Returned $270K—A 1250% ROI on a 'Wrong Domain'

Most founders agonize over buying their exact-match .com. David Park, founder of Jenni AI, did something different—he bought the misspelling.

In late November 2022, David spent $20,000 on Jenny.ai, the most common misspelling of his startup Jenni.ai. At the time, $20K was "a ton of money" for them.

Three years later, that "wrong domain" has delivered 1,871+ conversions worth over $270,000. That's a 1,250% ROI on a domain most founders wouldn't even consider buying.

The Sister's Name

The story starts with David's sister, Jeannie.

David named his AI writing assistant startup after her. The perfect domain—Jeannie.ai—was taken. So he had to choose a variation.

Jenny.ai was available, but David went with Jenni.ai instead. Why? Because "Jenni looks more like Jeannie than Jenny."

It wasn't the most optimal business move. But it was personal. As David put it: "Is it the most optimal business move? maybe maybe not. Sticking with Jenni either way."

That sentimental choice created a problem: people kept misspelling his startup as "Jenny."

The Misspelling Problem

David started noticing a pattern:

People DMing him would spell it "Jenny AI"
Social media comments repeatedly used "Jenny" instead of "Jenni"
Google Search Console showed significant search volume for "Jenny AI"

The data was clear: users were actively looking for Jenny.ai, not Jenni.ai.

Every misspelling was a potential customer leak. Every search for "Jenny AI" could land on a competitor's site or get lost entirely. And as Jenni AI grew, the problem would only get worse.

David had a decision to make: ignore the misspelling, or buy the domain.

The $20K Gamble

In late November 2022, David bought Jenny.ai for $20,000.

At the time, it felt risky. The startup was still early. $20K was "a ton of money" for them. But David had a framework for justifying the purchase:

Downside: In the worst-case scenario, he could resell Jenny.ai and maybe lose a few thousand dollars.

Upside: Recoup the cost through conversions and still own Jenny.ai, which would likely increase in value as Jenni AI grew.

The risk-reward made sense. He bought the domain.

The Slow Burn (2022-2023)

David set up Jenny.ai to redirect visitors to Jenni.ai and started tracking conversions.

By August 2023—nine months after purchase—the numbers looked like this:

52,000 visitors to Jenny.ai
20,000 new users redirected to Jenni.ai
212 paid subscriptions from Jenny.ai visitors

At Jenni AI's average customer lifetime value, David needed just 33 more paid subscribers from Jenny.ai to break even on the $20K purchase.

He was close to the finish line. But it was taking longer than expected.

The Summer Surprise

David hadn't accounted for one thing: summer break.

Jenni AI is a writing assistant popular with students and academics. Traffic to both Jenni.ai and Jenny.ai dropped drastically during summer months when users weren't actively writing papers.

The seasonal traffic pattern delayed breakeven by several months. David expected to break even by October 2023, but the summer dip pushed the timeline further.

It was a reminder that domain ROI calculations need to account for seasonality, not just raw conversion rates.

The Compounding Returns (2023-2025)

By October 2025—nearly three years after purchase—the numbers had compounded dramatically:

1,871+ conversions from Jenny.ai
Average customer LTV: ~$143
Total revenue from Jenny.ai: $270,000+
ROI: 1,250%

The $20K domain had returned $270K. And it wasn't done—every month, more users typed "Jenny.ai" instead of "Jenni.ai" and got redirected to the right place.

Would They Have Found Jenni Anyway?

When David announced the Jenny.ai purchase in August 2023, someone asked a fair question:

"What did the 'wrong domain' do? I wonder if these people would anyways have come to the 'right domain' as they were likely high-intent users (typing your domain)."

David's response was honest: "Yeah if I were to guess the majority of them would've found their way to Jenni regardless."

So why buy Jenny.ai if most users would find Jenni.ai anyway?

Two reasons:

Prevents leakage: Even if 80% of users would eventually find the right domain, that's still 20% who won't. At scale, that leakage becomes expensive.
Scales with growth: As Jenni AI grew, more people heard about it through word-of-mouth, social media, and press. The more awareness, the more misspellings. Owning Jenny.ai meant capturing that growth instead of losing it.

The defensive domain purchase wasn't about stopping 100% of leakage. It was about capturing the 10-20% that would otherwise be lost—and scaling that capture as the brand grew.

The Lesson: Defensive Domains Are Offensive Plays

Most founders think of defensive domain purchases as protection—buying domains to prevent competitors or cybersquatters from owning them.

David's story shows defensive domains can be offensive growth plays.

Jenny.ai wasn't just preventing loss. It was generating revenue:

1,871+ paying customers who might have gone elsewhere
$270K in lifetime value from redirected traffic
1,250% ROI on a domain most founders wouldn't buy

The "wrong domain" became one of Jenni AI's highest-ROI marketing channels.

When to Buy the Misspelling

Not every startup should buy misspellings. But David's framework is worth considering:

Buy the misspelling if:

People are actively searching for it (check Google Search Console)
You see misspellings in the wild (DMs, social comments, support tickets)
The downside is manageable (can resell for a reasonable loss)
Your brand is growing (leakage scales with awareness)

Don't buy if:

No evidence of misspellings (no search volume, no user confusion)
The cost is too high relative to scale (pre-revenue startup shouldn't spend $50K on a misspelling)
The misspelling is too different (if users who type it wouldn't want your product anyway)

David had clear evidence: Google Search Console showed "Jenny AI" searches, users were DMing him with the wrong spelling, and social media comments repeatedly used "Jenny" instead of "Jenni."

The data told him Jenny.ai was worth buying. The ROI proved it.

The Resale Safety Net

One underrated part of David's decision: the resale option.

When justifying the $20K purchase, David noted: "At the very very worst case scenario, I could at least re-sell Jenny.ai. So the downside was maybe losing a few thousands and the upside was recouping cost and still having Jenny.ai that hopefully would increase in value."

Premium short domains like Jenny.ai don't lose value quickly. If the redirect strategy had failed, David could have resold the domain—likely for close to what he paid.

That asymmetric risk-reward—small downside, massive upside—made the purchase decision easier.

The Personal Brand Choice

David's story also highlights something most founders don't talk about: sometimes brand decisions are personal, not optimal.

Choosing Jenni over Jenny wasn't the best business decision. Jenny is easier to spell, more recognizable, and already what users were searching for.

But David named his startup after his sister. Jenni looked more like Jeannie. And that mattered more than optimizing for SEO or user behavior.

The solution? Keep the personal brand (Jenni.ai) and buy the optimized brand (Jenny.ai) as a redirect.

You don't have to choose between sentiment and strategy. Sometimes you can afford both.

The 1,250% ROI Play

Three years after buying Jenny.ai for $20K, David shared the final numbers:

"I bought the misspelling of my startup domain 3 years ago. We now have 1871+ conversions just from people going to the wrong domain. Our LTV for a paid user is around ~$143. Which means the domain we paid $20k for has returned $270k. That's over a 1250% ROI :D"

The misspelling wasn't a mistake. It was a growth channel.

Defensive domain purchases aren't just about protection. They're about capturing every user who's already looking for you—even if they spell your name wrong.

For Jenni AI, buying the "wrong domain" was the right move.