Why I Decided to Build GradualRollout — And What I Hope to Achieve
Three months. That's how long my previous company went without a single production release. What started as daily deployments spiraled into a nightmare that cost me my job, ₹15 lakhs in lost equity, and nearly destroyed a 25-person engineering team.
This is the story of how deployment anxiety can kill a startup — and why I'm building GradualRollout to make sure it never happens to anyone else.
The Golden Days: When Deployments Were Simple
It wasn't always this way. When I joined as a lead engineer, we had something beautiful: daily deployments.
┌─────────────────────────────────────────────────┐
│ The Good Old Days │
├─────────────────────────────────────────────────┤
│ Monday ➜ Feature A ➜ Deploy ✅ │
│ Tuesday ➜ Feature B ➜ Deploy ✅ │
│ Wednesday ➜ Feature C ➜ Deploy ✅ │
│ Thursday ➜ Feature D ➜ Deploy ✅ │
│ Friday ➜ Feature E ➜ Deploy ✅ │
└─────────────────────────────────────────────────┘
One feature, one developer, one release. Clean and predictable.
Our internal feature flag tool was basic but functional:
// Simple and beautiful
if (featureFlags.newCheckout) {
return <NewCheckoutFlow />
} else {
return <OldCheckoutFlow />
}
Those were the days when I actually looked forward to hitting "deploy."
The Slow Descent Into Chaos
But success brought complexity. As we scaled to 10 developers working on 10 different features, cracks started to show:
┌─────────────────────────────────────────────────┐
│ What Went Wrong │
├─────────────────────────────────────────────────┤
│ ❌ No audit logs │
│ ❌ Analytics scattered across tools │
│ ❌ Zero transparency for PMs │
│ ❌ Nested flag hell in codebase │
│ ❌ No rollback strategy │
└─────────────────────────────────────────────────┘
Nested flag hell looked like this:
// The nightmare our codebase became
if (flags.newUI && !flags.oldCheckout && flags.experimentalFlow) {
if (user.isPremium && flags.premiumFeatures) {
if (flags.betaAccess || flags.adminOverride) {
return <ComplexFlow />
}
}
return <FallbackFlow />
}
// WHO KNOWS WHAT THIS DOES ANYMORE? 😱
What used to be daily releases became weekly. Then bi-weekly. Then monthly.
Then we stopped releasing altogether.
My Proposed Solution: "Give Me Two Weeks"
As deployment paralysis set in, I researched solutions and discovered canary deployments. I went to leadership with a proposal:
Give me two weeks and all my weekends. I'll build us a canary deployment system using Istio for load balancer routing and session stickiness. I already have a working prototype.
Here's what I wanted to build:
┌─────────────────────────────────────────────────┐
│ Canary Deployment Flow │
├─────────────────────────────────────────────────┤
│ │
│ 100 Users ──┬─ 90% ──► Stable Version │
│ │ │
│ └─ 10% ──► Canary Version │
│ │
│ 📊 Monitor: Error rates, latency, metrics │
│ ⚡ Rollback: Instant if issues detected │
│ 📈 Scale up: 10% → 25% → 50% → 100% │
└─────────────────────────────────────────────────┘
The answer? "No."
"Too risky. Too complex. We need to focus on features, not infrastructure."
What Happened Instead: 6 Months of Waste
Instead, our senior engineer built a "solution":
┌─────────────────────────────────────────────────┐
│ The Hacky Solution Timeline │
├─────────────────────────────────────────────────┤
│ Month 1-2: Development (Android only) │
│ Month 3-4: Testing & bug fixes │
│ Month 5-6: Firefighting after release │
│ │
│ Result: ❌ Nobody uses it anymore │
│ ❌ 6 months completely wasted │
│ ❌ Team morale destroyed │
└─────────────────────────────────────────────────┘
The "solution" only worked on Android. It was fragile, unreliable, and after 6 months of effort, was quietly abandoned.
Meanwhile, I could have built a proper canary system in 3-4 weeks, with test environment integration working in just 2 weeks.
The Three-Month Freeze: When Everything Fell Apart
Picture this: You're sitting on 200-300 file changes across multiple features, developed by different people, with interdependent flags that nobody fully understands anymore.
┌─────────────────────────────────────────────────┐
│ Deployment Paralysis │
├─────────────────────────────────────────────────┤
│ │
│ Daily ──► Weekly ──► Monthly ──► ??? ──► 💀 │
│ │
│ 😰 200-300 file changes pending │
│ 🔥 Test environments broken │
│ 😡 Marketing team furious │
│ 💸 Revenue opportunities missed │
│ 🤯 Engineering team stressed │
└─────────────────────────────────────────────────┘
Every potential release felt like playing Russian roulette.
As the engineering lead, I was drowning. Every night I'd go to bed wondering: "If we release tomorrow, what will break? Which flags conflict with each other? What if the payment flow fails for our biggest client?"
The Personal Cost: More Than Just Code
This wasn't just a technical problem — it became deeply personal.
┌─────────────────────────────────────────────────┐
│ Personal Impact │
├─────────────────────────────────────────────────┤
│ 💰 ₹10-15 lakhs lost (salary + ESOPs) │
│ 📈 No career growth/promotion │
│ 😰 Chronic stress and anxiety │
│ 🔥 Reputation damage as "lead" │
│ 💔 Lost faith in my abilities │
└─────────────────────────────────────────────────┘
The company suffered even worse:
- Growth trajectory flatlined
- Series B investors put 60% of funding on hold
- Layoffs: 10-20 people, including me
- CMO fired shortly after I left
- Company vacated an entire floor 8 months ago
The human cost was devastating:
- Developers actively looking for jobs elsewhere
- Constant fights over OKRs and everything else
- Team morale completely destroyed
- Stress levels through the roof
The tragic irony? Great leadership, well-intentioned management — but technical debt and deployment fear poisoned everything.
The Recovery: From Unemployment to Revelation
Two months unemployed. Rejection after rejection. Questioning everything I thought I knew about engineering.
A few more months to recover mentally. The financial stress, the damaged confidence, the imposter syndrome — it all takes time to heal.
Then I wanted to stay relevant. The tech industry moves fast. I decided to start a side project to upskill and keep my edge.
I browsed through ideas. SaaS tools, mobile apps, developer productivity tools. Nothing clicked.
Then I came across feature flags.
Everything came flooding back.
The sleepless nights. The deployment anxiety. The team fights. The wasted 6 months. The rejected proposal.
I realized something powerful: I understood this problem better than anyone because I had lived through its worst consequences.
From Pain to Purpose: Why GradualRollout Exists
This wasn't just another side project idea. This was personal.
I started researching the market:
┌─────────────────────────────────────────────────┐
│ Existing Solutions Problems │
├─────────────────────────────────────────────────┤
│ LaunchDarkly: ₹50,000+/month (too expensive) │
│ Split.io: Enterprise focus only │
│ Unleash: Missing canary capabilities │
│ Custom: 6 months of wasted effort │
└─────────────────────────────────────────────────┘
The tools that could have saved my previous company were built for enterprises, not the fast-growing startups that need them most.
But more importantly: None of them solved the real problem — deployment fear.
Feature flags without canary deployments are just fancy toggles. What teams need is confidence to deploy, not just the ability to toggle features.
That's when I decided to build GradualRollout.
What I'm Building (And Why It's Different)
┌─────────────────────────────────────────────────┐
│ GradualRollout Vision │
├─────────────────────────────────────────────────┤
│ 🎯 Feature flags + Canary deployments │
│ ⚡ 5-minute setup (not 5-day enterprise) │
│ 🔍 Full audit logs and transparency │
│ 💰 Startup pricing, enterprise features │
│ 🤝 PM-friendly controls │
│ 📊 Unified analytics dashboard │
└─────────────────────────────────────────────────┘
The integration I wish we had:
// Simple feature flags
const showNewFeature = useFeatureFlag('new-checkout')
// With built-in canary deployment
const canaryConfig = useCanaryDeployment('new-checkout', {
percentage: 10,
monitoring: ['error_rate', 'latency'],
autoRollback: true
})
// Deploy without fear
return showNewFeature ? <NewCheckout /> : <OldCheckout />
35 days after starting development, we launched our feature flags in beta. Canary deployments are coming next.
The Vision: Deploy Without Fear
Here's what I want to achieve:
For developers: Ship code confidently, knowing you can roll back instantly if something goes wrong.
For product teams: Control feature rollouts without technical dependencies.
For companies: Maintain rapid development velocity as you scale from 5 to 50 to 500 engineers.
For the industry: Make canary deployments as standard as version control.
Even If This Fails, It's Worth It
Will GradualRollout become the next unicorn? Maybe, maybe not.
But even if this venture doesn't work out commercially, I'll keep it alive. I'll use it for my own projects. I'll open-source parts of it.
Because at least I'll know I built a solution to the biggest problem I faced in my career.
At least other developers won't have to go through what I went through.
At least one team won't have to choose between "deploy and pray" or "never deploy at all."
What's Next
If you've made it this far, you've probably experienced similar deployment pain. Maybe you're sitting on a week's worth of changes, afraid to ship. Maybe your team argues about release timelines in every planning meeting.
You don't have to live with deployment anxiety.
Try GradualRollout's interactive demo and see how feature flags + canary deployments can transform your team's confidence.
Or better yet, reach out to me directly. I'd love to hear your deployment horror stories and discuss how we can solve them together.
Because every team deserves to deploy without fear.
💡 Full Transparency: GradualRollout is an indie project currently in beta. As a solo founder building this platform, I'd love your feedback on what features would be most valuable for your deployment workflow. Your input will directly shape the future of the product!
Have your own deployment nightmare story? I'd love to hear it. Sometimes knowing you're not alone makes all the difference.
