How The Stock Insider, a Finance Newsletter, Weaponised Price Psychology

Jack Roshi, the creator of The Stock Insider, tested multiple pricing strategies for his Substack newsletter.

He offered a $300/month plan, a $400/year plan, and a $500 lifetime plan. After extensive testing, the lifetime plan consistently generated the most revenue over time.

He shared that he initially offered all three pricing tiers. Over time, he observed that most buyers chose the lifetime plan.

Decoy Pricing Framed the Lifetime Plan as a Steal

The monthly and annual plans weren’t designed to sell. They were placed there to make the $499 lifetime plan look like a better deal.

The psychology behind it was simple: if someone sees $300/month and $400/year next to $499 for life, the lifetime plan feels like a discount—even though it’s technically a higher one-time charge. This anchored perception led most people to take the $499 option.

The decoys existed purely to push people toward the real offer.

Upfront Cash Enabled Immediate Business Reinvestment

By collecting large amounts of cash upfront through lifetime deals, Jack had capital to reinvest into the business. This funding helped pay for marketing, tools, ads, and content creation without waiting for monthly drip revenue.

In the early growth stages, speed matters more than recurring billing. Having money upfront allowed for compounding faster than the subscription cash flow model would have allowed.

It allowed him to buy an NVIDIA DGX B200 AI Supercomputer for over $500,000.

Niche Dictates How Much You Can Charge

Pricing success depends entirely on the niche. Broad-audience newsletters like humor or news should stick to low-ticket pricing, around $5/month. These readers typically seek entertainment or light information and aren't conditioned to pay more.

In contrast, newsletters offering niche intelligence—especially in sectors like oil, energy, and finance—can charge up to $300/month. These subscribers expect insights that help them make or protect money, so they view the subscription as an investment rather than a cost.

Financial Niche + Wall Street Cred Justified Premiums

This particular newsletter delivered actionable financial insights. The writer brought real experience from Wall Street and offered deep knowledge on stock trading. That level of credibility justified higher prices.

Readers weren’t paying for content—they were paying for the chance to make money using the information. That alone changes the dynamic and creates a pricing ceiling far above typical consumer newsletters.

After $1M in Revenue, the Model Was Retired

Once the newsletter crossed $1 million in lifetime revenue and landed in Substack’s top 50 newsletters, the creator phased out the lifetime offer.

At that point, the brand had traction. The email list was large. The results spoke for themselves. He no longer needed to incentivize buyers with a one-time offer.

Instead, the pricing changed to two annual plans:

• Elite plan at $2,970/year

• Standard annual plan at $970/year

Decoys Worked Until Market Trust Was Locked

The decoy model served a temporary but vital purpose. It helped build early momentum by using pricing psychology to guide people to one offer. But once trust, authority, and scale were established, the decoys were no longer needed.

With a reputation built and results delivered, the creator could charge higher annual fees without friction. The lifetime plan had served its role—now the business model could shift.

Growth Milestones Justify Shifting to Subscriptions

Hitting seven figures in revenue and cracking Substack’s leaderboard marked a clear growth milestone. At this level, predictable annual revenue became more valuable than upfront cash. The business was no longer in its infancy.

The new structure with $2,970/year and $970/year plans reflects that maturity. But that shift only worked because the earlier decoy strategy funded the business’s initial lift-off.

Top Tweets of the day

1/

Shaan Puri is GOAT'ed with his observations. The real competition is always distractions.

2/

Nikita Bier is a king of social apps. He nails it in the last line: "if you insist on using voice in your product, the primary value of voice is an emotional connection."

So many apps can be built just on this premise.

ChatGPT's Sky (Scarlett Johanson's voice) and Grok's naughty voice (spotted in Karpathy's "How I use LLMs" video) is the kind of voice that will take off.

Sin niches are the best ones to monetize. Almost everyone uses those secretly. Massive market.

3/

What a genius hack.

Personalized onboarding monitored on usage has never been solved. There is a SaaS product hidden in there. Just need a bunch of conditionals. I think Superwall kinda does it but I don't think it gives the full premium experience for free. Not sure.

Rabbit Holes

1. AI Engineering in 76 Minutes (Complete Course/Speedrun!) by Marina Wyss

2. Always set temperature to zero if you want the model to stick to the prompt by /r/ChatGPTCoding

3. First, ten by Seth Godin

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