Peak claim: "Save thousands per month by blocking coupon leaks from Honey, Capital One Shopping, and RetailMeNot"

Final outcome: Killed overnight by Shopify's checkout.liquid deprecation announcement

Lesson: Platform dependencies can destroy even profitable businesses instantly

💰 The Money Trail

First external funding for serial entrepreneur Dennis Hegstad after two bootstrapped exits

👨‍💻 The Founder Story

Dennis Hegstad Serial entrepreneur with a track record:

• Previously sold LiveRecover (SMS recovery) and OrderBump (checkout upsells) for 7-8 figures each

• Austin-based, known for Twitter growth hacking and DTC expertise

• First time raising external capital after bootstrapping success

🔧 What They Actually Built

Vigilance was a Shopify app that monitored and blocked unauthorized coupon code injections at checkout. The pitch was simple: browser extensions like Honey were costing merchants 5-10% margins per order by auto-applying leaked codes.

Core features:

• Real-time leak detection across social media and coupon sites

• Attribution tracking (which extension injected the code)

• One-click blocking or pausing of compromised codes

• ROI calculator showing revenue saved

Target market: Shopify Plus merchants (typically $200K+ monthly revenue) running influencer campaigns

📉 The Spectacular Unraveling

Timeline of doom:

• Nov 2022: Public beta launch

• Dec 7, 2022: Full Shopify App Store launch

• Jan 2023: ~50 Shopify Plus customers, growing fast

• Feb 2023: Shopify announces checkout.liquid deprecation

• Feb 2023: Immediate shutdown decision

• Aug 2024: Original deprecation deadline (later extended to 2025)

The killer blow came when Shopify announced that the 'checkout.liquid' file is being deprecated with a new 'checkout extensibility upgrade' replacing its function. Vigilance's entire blocking mechanism relied on checkout.liquid scripts - the new system didn't support their approach. Like AllHere's dependency on unproven AI claims, Vigilance had built its entire product on soon-to-be-obsolete technology.

📊 The Obituary Scorecard

💡 Lessons for Founders

1. Platform risk is existential risk - When you build on someone else's platform, they control your destiny. Unlike Clinkle's self-inflicted wounds or Odeo's market disruption (iTunes), Vigilance was killed by its own platform partner

2. Technical deprecations kill faster than competition - No amount of product-market fit matters if the underlying tech disappears

3. First external funding adds pressure - Hegstad's prior bootstrapped exits gave him freedom; with investors, he felt obligated to try pivoting rather than shutting down immediately

4. Narrow TAM compounds platform risk - Shopify Plus-only market meant limited options when the platform changed

🪦 Final Tally

• Customers abandoned: ~50 Shopify Plus merchants

• Investor outcome: Offered refunds, investors said "try something else"

• Founder outcome: Launched Internet Research Unit in 2024

• Current status: Domain dead, app delisted, founder moved on

The irony? Shopify updated its checkout system, ultimately killing Vigilance, so we shut it down, but the deprecation deadline kept getting extended. Vigilance died in 2023 for a change that wouldn't fully roll out until 2025. Sometimes being too proactive about platform changes is worse than being reactive. Like Free's beautiful solution to a problem users didn't urgently need solved, Vigilance shut down prematurely for a threat that took years to materialize. In the end, Vigilance proved that even a working solution to a real problem can't survive when the platform pulls the foundation out from under you. 🏚️

Building a startup is like walking a tightrope—one wrong step, and you’re in a startup obituary. I hope this story helps you stay balanced and avoid the common pitfalls.

If it did, do a fellow founder a favor—share it and help them dodge a disaster! 🚀

Cheers,

Ram

StartupObituary.com 

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Startup Obituary is for educational purpose only not a business advice.