Goodwill in Side-Project Acquisitions: Are You Paying for "Vibes" or Real Value?

Imagine you’re looking to buy a micro-SaaS, a newsletter, or a content site. The seller wants $25,000. You check the hard assets:

• Codebase? Nothing groundbreaking.
• Email list? 2,000 subscribers, but no clear engagement stats.
• Revenue? A steady trickle, but not game-changing.

So why is the asking price so high?

Goodwill.

When buying a digital asset, goodwill is often the biggest part of the purchase price—but it’s also the hardest to measure. It’s the premium you pay for intangible value like brand recognition, SEO rankings, customer trust, and community engagement.

But not all goodwill is created equal. And some of it? Completely worthless. Let’s break down what you need to know—whether you’re buying a project or trying to sell one for top dollar.

What Buyers Need to Know About Goodwill in Digital Assets

You're Betting on Intangibles

If you’re paying more than the raw value of an asset, you’re betting that the existing audience, reputation, or traffic will continue after the transfer. But ask yourself:

• Will users stick around when ownership changes, or are they just here for the founder’s personal brand?
• Is the brand actually recognized, or is it just a handful of Twitter followers hyping each other up?
• Are SEO rankings stable, or will they disappear the next time Google sneezes?

If 80% of the value is goodwill, you need to be damn sure it’s transferable. Otherwise, you’re overpaying for vibes.

Common Goodwill Traps in Digital Acquisitions

The "Founder-Driven" Trap

Some indie projects have a cult-like following around the creator. If they leave, the audience leaves too.

Example: Buying a personal brand-driven newsletter. If the audience is there for the founder’s hot takes, why would they care about you?

If Tim Ferriss sold his mailing list, do you think his readers would stick around for some random dude’s productivity tips? Doubtful.

The "Google-Owned" Trap

Many websites rely on SEO traffic, but rankings can tank overnight.

Check diversification - does traffic come from multiple sources, or is it 90% Google? If the answer is the latter, understand that you’re one algorithm update away from holding a worthless site.

The "Tech Debt" Trap

That “clean” codebase might be a house of cards. Poorly documented, patched together, or reliant on outdated tech—some sellers are offloading a maintenance nightmare.

Reality check: If you’re not a developer, make sure someone who is takes a hard look before you buy.

How to Assess Goodwill Before Buying

Before dropping cash on a project, demand proof that goodwill is real and sustainable. Here’s what to check:

✅ Traffic Stability – Look at the last 12 months of Google Analytics. Any sudden spikes? Check if they were from a temporary viral moment or sustained organic growth.

✅ Audience Engagement – Newsletters and social accounts with 50k subscribers mean nothing if open rates and click-throughs are low. Get the engagement data.

✅ Revenue Stickiness – If it’s a subscription model, check churn rates. Low churn = high goodwill. High churn = you might be buying a sinking ship.

✅ Brand Recognition – Are people talking about this project organically? If yes, that’s goodwill. If not, it might just be another forgettable website.

If a seller can’t prove these things, they’re selling you a dream, not a business.

Red Flags to Laugh At

• A community with 17 people in Discord is labelled a "vibrant community". Check the timestamps and avoid buying a ghost town.
• "Brand Equity" that's one logo, one blog post, one traffic spike and zero recognition. Everyone thinks they can build a brand. But mostly they build a colour scheme. If nobody is talking about it, sharing it or searching for it, it's not a brand.
• "SEO-machine" built on ChatGPT blogspam. 300 AI-generated posts that start with "In today's fast-paced world..." will inevitably lead to content in a digital landfill.

For Sellers: Goodwill Is Your Hidden Value

Goodwill is where you make your money when selling a project. The more you can prove your audience, brand, and revenue streams are durable, the more you can justify a higher price.

How to Sell Goodwill for Top Dollar

Prove Customer Trust

• Show testimonials, user engagement metrics, or repeat purchases.
• If it’s a SaaS, provide retention and churn numbers.

Make the Transition Seamless

• Have clear documentation, so buyers feel confident they can run things without you.
• If you’re willing to stay on for a transition period, that reduces buyer risk.

Show Growth Trends

• Is traffic growing steadily, or was last month an anomaly?
• Buyers pay for predictability, not just past success.

The Tax Side of Goodwill in Digital Asset Sales

Nothing kills your payday like a tax bill you didn’t plan for. Depending on your country, goodwill in a digital asset sale may be taxed differently than other assets. In many cases, goodwill is taxed at a lower capital gains rate.

Pro tip: Work with a tax professional to structure your deal for the best outcome. For more on how goodwill impacts taxes, check out this guide on intangible asset taxation.

Negotiating Goodwill: The Buyer-Seller Showdown

Since goodwill is subjective, it often becomes the biggest sticking point in negotiations.

Buyers try to downplay goodwill:

• “Your traffic might not last.”
• “Customers only trust you, not the brand.”
• “There’s no guarantee the revenue will continue.”

Sellers argue for more goodwill value:

• “Our brand has a strong following.”
• “Customers stay long-term – we have proof.”
• “The business is growing steadily.”

How to Close the Gap: Earnouts & Seller Financing

One way to bridge goodwill disagreements is earnouts – where part of the purchase price depends on future performance.

For example, if you’re buying a newsletter and worried about engagement dropping, you could structure the deal so that the seller gets an extra payout only if open rates stay above 40% for the next 6 months.

This protects buyers from overpaying and gives sellers a chance to prove their claims.

The Case for Zero Goodwill

Let’s play devil’s advocate for a second – what if goodwill is just a fancy word for wishful thinking?

Buyers love to talk themselves into overpaying. “The brand has potential.” “The audience is loyal.” “The SEO is strong.” Blah blah blah. Sounds nice—until you’re six months in, bleeding cash, realizing that it was a mere fantasy. 

Remember that most “goodwill” in Indie projects is non-transferable:

• That “trusted brand” was never a brand. It was a founder LARPing as an influencer.
• The “newsletter audience” opens emails because they like the sender, not the topic.
• The “organic traffic” came from one blog post that accidentally ranked for something it shouldn’t have.

If it can’t survive without the founder holding its hand, it’s not goodwill – it’s dependency. And you don’t pay a premium for that!

The truth? Goodwill is often just the tax you pay for not doing enough due diligence. So if you’re not 100% sure it’s real, assume it’s worth zero. You’ll make fewer emotional buys – and avoid inheriting someone else’s overpriced side project in hospice care.

The Bottom Line on Goodwill in Digital Assets

For buyers, goodwill is a bet on future value – do your due diligence to make sure it’s real.

For sellers, goodwill is your biggest leverage point – but you need to prove it’s sustainable.

Either way, don’t get suckered into a bad deal. If you’re a buyer, don’t pay for vibes. If you’re a seller, make damn sure your brand isn’t just propped up by your personal Twitter following.

At the end of the day, goodwill is only worth what someone else will pay for it. Be smart. Be skeptical. And don’t get stuck with a worthless asset. If your project dies the moment you log off Twitter, maybe it was never a business to begin with.

Looking to buy or sell a digital asset? Check out our community, where founders and acquirers connect for smarter deals.

Stuff that's less fun to read than this:
- How to Value a Website Before Buying
- The Role of Goodwill in Digital Business Transactions