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My app failed, then I changed one thing, and made $80K | Starter Story

September 13, 2026

AI Summary

5 min read

Prince left a $250,000-a-year software engineering job in India to build apps full-time. His first attempt, a web app called Rabbit Holes AI, got almost no traction. Then he changed one thing: the pricing model. He switched from a subscription with a free trial to a one-time purchase with a bring-your-own-API-key model, rebuilt the app as a desktop application, and generated $80,000 in gross revenue over the next six months, with roughly $75,000 in profit.

The Problem with the First Version

The app itself is a "canvas-first" interface for interacting with AI models. Prince’s insight was that linear chat interfaces like ChatGPT lose context during long conversations. His app lets users branch conversations into new nodes, creating a visual map of forks and tangents. He built the first version as a web app with a freemium subscription model: a few free questions, then a paywall.

That version failed for several reasons. Prince had no personal brand and wasn't "building in public," so he couldn't drive traffic through social presence. More critically, his ideal customer profile (ICP) was a "power AI user"—someone who already paid for multiple AI subscriptions like ChatGPT, Claude, and Perplexity. Asking these users to add yet another monthly subscription was a non-starter. The free trial attracted curiosity but never converted into paying customers.

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What you'll learn

  • 1 (02:08) **The Pivot That Changed Everything** - Prince quit a $250k engineering job to build apps; the first version of his app, Rabbit Holes AI, got no traction until he changed the pricing model.
  • 2 (03:08) **What Rabbit Holes AI Actually Does** - Prince explains the product: a canvas-first interface for interacting with multiple AI models, solving the problem of linear chat losing context.
  • 3 (04:38) **Why the First Pricing Model Failed** - Prince details the initial freemium/subscription strategy and why it was the wrong move for a bootstrapped founder with no personal brand.
  • 4 (05:42) **The Mechanics of the One-Time Purchase Pivot** - Prince explains the specific technical and business changes required to make the one-time purchase model work: eliminating all server and AI costs.
  • 5 (06:28) **The Immediate Impact of the Pricing Change** - Prince describes the qualitative and financial results of switching to a one-time purchase model.
  • 6 (06:51) **Why Every Bootstrapped Business Should Offer a Lifetime Deal (LTD)** - Prince makes a strong case for LTDs as a strategic tool for bootstrapped founders.
  • 7 (10:48) **Tactical Pricing of a Lifetime Deal** - Prince shares the specific pricing strategy he used for Rabbit Holes AI's LTD.

+ Full timestamped outline available in the app

Show Notes

My app failed, then I changed one thing, and made $80K

Sharing ideas that make money!

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-------- Keywords: bootstrap startup, startup founder, revenue stories, app marketing, saas business, indie hacker

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