The Upsell Gauntlet: How a Business Model Drove Me Away Before I Tried the Product

Field Note #10: The Gauntlet

I paid for a lifetime license and never made it to the product

I recently bought a lifetime license for a SaaS tool. The price was reasonable, the offer made sense, and I was genuinely curious about the product. I paid, hit the confirmation screen, and felt good about the decision.

What followed was four or five pages of upsells for add-ons, companion products, and extended packages. Page after page. Each one designed to look like a critical next step rather than a sales pitch. The links that would actually take me into the product I had just purchased were buried, small, de-emphasized, easy to miss.

By the time I reached the end of the gauntlet, I didn't want to be there anymore.

The thing that made it worse

I'd mistyped my email during signup. So when I finally cleared the upsells and tried to log in, I couldn't. That one was on me. I wrote to support to explain, and while I was there I asked for a refund. Not because of the email mistake, but because by the fourth upsell screen, my goodwill toward the product had evaporated.

They wrote back promptly, fixed my account, and were kind about it. They did not mention the refund. They did acknowledge my frustration with the upsells, noting, essentially, that this is how they operate and that it works for them.

Fair enough. That's a legitimate business decision. I'm wrestling with my own monetization choices every week; I understand that these things don't happen by accident. They made a deliberate call, and I respect that they own it.

So with a working account, I gave the product an honest look.

The product itself

The features I was actually interested in were locked behind a higher tier. Not surprising given everything that had come before, but still deflating. The ones I did have access to were functional but not particularly easy to use. And the upsells didn't stop once I was inside. They were woven into the interface. Prompts to upgrade tucked in next to features I was trying to use. Banners celebrating minor milestones, pivoting immediately into an offer.

Today you reached a 10-day streak! Upgrade now and save $$$.

It's a small thing. But when you've paid for something, you don't expect your own achievement notifications to be hijacked into a sales pitch. It interrupts the creative process. It reminds you, constantly, that the product sees you primarily as a revenue opportunity rather than as someone trying to get work done.

After a few days, I asked for a refund again.

The counter-offer

Their response this time was a generous one, technically. Rather than refunding me, they offered to give me my choice of any of their upsell packages -for free. Many of them were listed at $99 or more. It was a real offer, financially speaking.

I didn't take it.

I don't work that way. I don't want to be nudged, cornered, or sweetened into a decision. I want to find value on my own terms, and then make a choice based on that.

What drove me away was not the product. It was the relationship the product wanted to have with me.

A conscious choice

I want to be clear: I'm not writing this to criticize that company. They built something, found a model that works for them, and are executing on it. The aggressive upsell funnel is a legitimate strategy. Plenty of successful SaaS businesses run exactly this way.

But it's not the relationship I want to build with the people who use Everstep.

When you're close to your request limit, I'll tell you. Not to pressure you into upgrading. Not because I want you to feel urgency. But because your operations could actually be affected, and you deserve to know before that happens. There's a difference between informing someone and aggressively steering them.

If you find value in Everstep, upgrade when you're ready. I want that decision to come from a clear-eyed assessment of whether the tool is working for you -not from a badge notification, a buried button, or a carefully timed offer while you're trying to focus.

What this experience reminded me

A product's business model is part of the product. The way a company asks for money says something about what they believe the relationship with their customer is. It sets a tone from the very first interaction that either builds trust or quietly erodes it.

I didn't have a bad experience with that company's software. I had a bad experience with what the software communicated about how much the company respected my time and my judgment.

That's a harder problem to fix than a buggy feature.