Substack's Leaderboard Ranking Secrets: Growth Insights from #3 Finance Newsletter

The Stock Insider ranks as #3 paid newsletter in Substack's Finance category, focusing on stock market analysis and investment strategies.

Founder Jack Roshi shared his insights with me on navigating Substack's algorithm.

With 444k+ free subscribers and 1000+ paid subscribers, The Stock Insider launched with one goal: generate enough cash flow to cover operations and salaries.

Foundation for Success: Building Credibility and Setting Strategic Pricing

The $10/month launch price served as a strategic loss leader, prioritizing subscriber acquisition over immediate profit. This early-bird pricing rewarded initial supporters with the highest tier access.

Jack's 15 years of Wall Street experience combined with targeted audience strategy accelerated growth and established crucial early credibility.

The Power of Viral Content: One Post That Transformed Growth

Substack awards a "Bestseller" badge at 100 paid subscribers—a milestone The Stock Insider hit by its 6th post. A viral NVIDIA analysis predicting a stock split delivered 135 paid subscriptions from a single post.

This demonstrated how well-positioned content combined with Bestseller visibility creates immediate financial returns while compounding platform benefits.

Bestseller status unlocks tangible benefits: dedicated Substack support, private Zoom calls with insider insights, early access to beta features, and enhanced Browse page visibility.

The browse feature gets you over 50k views over 3 days, which can lead to increased engagement and potential subscribers.

Most importantly, the badge itself increases credibility, boosting conversion rates significantly.

Strategic Pricing Evolution: From Entry-Level to Premium

As traction grew, monthly subscription prices increased systematically: $10 → $300 → $400 → $500.

No discounts were offered, even during Black Friday.

Instead of lowering prices, new products were introduced at higher price points, maintaining premium positioning and perceived value.

The Lifetime vs. Recurring Revenue Balance

Lifetime pricing initially delivered superior margins, nearly doubling revenue compared to annual models. Jack Roshi with his previous startup experience knew that annual churn is 50-60% so one-time payments locked in maximum customer value while eliminating future churn risk.

Despite Substack's algorithm changes, lifetime offers remain customer favorites.

Their perceived higher value drives strong conversions, and the cash influx funded growth initiatives like a Tesla giveaway (now removed) that expanded both free and paid subscriber bases.

Navigating Substack's Algorithm Shift to ARR Rankings

Substack pivoted its leaderboard metrics to prioritize Annual Recurring Revenue (ARR) over lifetime sales.

Before this change, the newsletter ranked as high as #23, driving 10,000-15,000 monthly organic signups.

After the shift, it dropped into the 100s despite surpassing $1M in revenue.

Lifetime subscriptions no longer contributed to rankings, forcing a strategic return to recurring models—good for Substack, less optimal for publishers' immediate revenue.

Leaderboard positioning is delivers a 20-30% growth advantage over newsletters focused on lifetime deals.

Rankings focus exclusively on Annual Recurring Revenue, excluding comped and lifetime users, and use Trailing Twelve Months metrics rather than monthly fluctuations.

Substack's Platform Priorities: The Recurring Revenue Preference

Substack discourages lifetime pricing to protect platform integrity. Lifetime sellers who disappear after initial success damage reputation and increase chargeback risks.

The platform shoulders real infrastructure costs—from email delivery to hosting and support—making recurring revenue essential for ecosystem health.

Substack's email infrastructure sends through whitelisted domains (like [email protected]) with nearly 100% deliverability rates, significantly enhancing reach even with custom domains (like using newsletter.thestockinsider.com).

Mastering Growth Mechanisms: Notes, Browse Pages, and Curation

Notes drive powerful growth when used strategically. Posts need 30-50 likes or restacks to surface on the Browse page.

At 100+ likes, content penetrates beyond direct followers into the broader Substack network. Substack Notes that work are mostly inspirational than actionable, but they still drive massive engagement and build a loyal following.

Jack recommends posting on Substack Notes anywhere from 5 to 20 times per day for maximum growth.

Some people post every hour.

Browse page features aren't fully automated—human editors review posts before prominent placement, preventing low-quality affiliate content from dominating high-traffic areas.

The Stock Insider was at #10 yesterday.

Learning from Successful Newsletters - Lenny's Newsletter and Doomberg

Observing other newsletters validated the model's potential.

Lenny's Newsletter showed how accessible writing could build million-dollar businesses.

Doomberg's growth to 10,000+ paying members today (projected $20-30M/year with sponsorships) demonstrated the scalability of newsletter businesses in the Finance field.

Building a Sustainable Growth Engine

The 444,000+ free subscriber base created a durable growth machine with over 1000 "true fans" who reliably boosted new launches like new newsletter and a book.

Initial success made launching additional newsletters easier.

A second $5/month newsletter known as Anti-Clickbait News quickly reached 1,000+ paying subscribers (and 57,000 total subscribers) within months by leveraging the existing warm audience.

Jack's long-term goal is to have 10 such newsletters on Substack managed by a small team. The genius of this strategy lies in leveraging the power of the Substack community to create a network effect, where each newsletter becomes a magnet for new subscribers and contributors. And it can be used to cross-promote each other's newsletters.

This technique is effectively used by all big media which is owned by the same parent company under different names. For example, Dating Apps are monopolized by a single parent group and there are newspapers that owned by the same parent company. They just operate under different names.

Crossing $1M revenue in the first year with just 2.5 team members validated the model's effectiveness. Strategic viral posts, pricing psychology, and leaderboard positioning created sustainable, exponential growth.

Substack's leaderboard isn't mere vanity—it's oxygen for newsletters aiming to dominate their niches. Understanding its hidden rules separates enduring winners from temporary successes.

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