Growth & Strategy
Personas
SaaS & Startup
Time to ROI
Short-term (< 3 months)
Last month, I watched a startup founder panic because their website went down during a product launch. The irony? They'd been religiously following a "comprehensive" 47-point maintenance checklist they found online.
Here's the uncomfortable truth I've learned after building dozens of startup websites: most maintenance advice is written by agencies trying to justify monthly retainers, not by people who understand the reality of bootstrapped startups.
You know what actually breaks websites? It's rarely the stuff those checklists obsess over. Instead, it's the simple things that get overlooked because founders are drowning in busywork.
After years of being the guy startups call when their sites break (usually at 2 AM), I've developed a completely different approach to website maintenance. One that actually works for teams of 1-5 people who don't have dedicated DevOps staff.
Here's what you'll learn from my experience:
The 3 maintenance tasks that prevent 80% of website emergencies
Why most "comprehensive" checklists actually make your site less stable
My 15-minute weekly routine that's saved me countless emergency calls
When to ignore expert advice and trust your instincts instead
The automation setup that works even if you're not technical
Industry Reality
What every startup founder gets told about website maintenance
If you've ever searched "website maintenance checklist," you've seen the same advice recycled everywhere. The industry has convinced startups they need to be doing monthly plugin updates, weekly security scans, daily backup checks, and quarterly performance audits.
Here's the typical maintenance checklist most agencies recommend:
Update all plugins and themes monthly
Run security scans weekly
Check all forms and links quarterly
Optimize images and database regularly
Monitor uptime and performance daily
This advice exists because it makes sense in theory. Websites are complex systems, and complex systems need regular maintenance, right?
The problem is, this approach treats all websites like they're enterprise-level applications serving millions of users. It assumes you have a dedicated team, unlimited time, and the luxury of treating website maintenance as a full-time job.
But here's what actually happens: startup founders add these tasks to their already overwhelming to-do lists, feel guilty when they can't keep up, and either burn out trying to follow impossible standards or ignore maintenance entirely until something breaks.
The maintenance industrial complex has created a false choice: follow their comprehensive system or accept that your website will fail. But there's a third option that actually works for real startups.
Consider me as your business complice.
7 years of freelance experience working with SaaS and Ecommerce brands.
The wake-up call came during my second year as a freelance web developer. I was working with a SaaS startup that had religiously followed every maintenance "best practice" they could find. They updated plugins weekly, ran security scans daily, and had a 50-point monthly checklist.
Then their site went down during their biggest product launch of the year.
The culprit? A "minor" plugin update that broke their checkout process. While they were busy checking off boxes on their maintenance list, they'd missed the one thing that actually mattered: testing critical user flows after making changes.
This wasn't an isolated incident. Over the next few months, I started tracking maintenance-related issues across my client base. What I discovered completely changed how I think about website stability.
The startups following comprehensive maintenance checklists were actually experiencing more problems than those with minimal maintenance routines. They were so focused on technical busywork that they'd stopped paying attention to what their users actually experienced.
Meanwhile, the most stable websites I managed belonged to founders who ignored most "expert" advice and focused on just three things: keeping their site backed up, monitoring what users actually see, and only making changes when there was a clear business reason.
That's when I realized the entire industry had it backwards. We were optimizing for technical perfection instead of business continuity.
I started questioning everything. Why update plugins if they're working fine? Why run daily security scans if you're not actually reviewing the results? Why follow a checklist created by someone who's never run a startup?
So I threw out the conventional playbook and started building maintenance routines based on what actually breaks websites in the real world.
Here's my playbook
What I ended up doing and the results.
After analyzing hundreds of website failures, I developed what I call the "Anti-Maintenance" approach. Instead of following exhaustive checklists, I focus on the minimum viable maintenance that prevents maximum damage.
The Core Philosophy: Prevention Over Perfection
Most maintenance advice focuses on keeping everything technically perfect. My approach focuses on preventing business-critical failures. There's a huge difference.
Here's my complete system:
The 3-2-1 Rule (Weekly - 15 minutes total)
Every Monday morning, I spend exactly 15 minutes on three tasks:
3 minutes: Check that your most important user flows still work. For most startups, this means signup, login, and purchase/contact forms. I literally go through these flows as a user would.
2 minutes: Verify your automated backups are actually working. Most people set up backups and never check them. I download one backup file and spot-check that it's not corrupted.
1 minute: Review any error notifications from the past week. Not fixing them immediately, just acknowledging what's breaking and whether it matters.
The "If It Ain't Broke" Protocol
This goes against everything the industry teaches, but I only update plugins, themes, or code when:
There's a critical security vulnerability affecting my specific setup
A feature I actually use stops working
I'm adding new functionality that requires updates
I've had clients run the same WordPress version for 18 months without issues because we weren't chasing unnecessary updates.
The Business Impact Filter
Before doing any maintenance task, I ask: "Will this directly impact user experience or business operations?" If the answer is no, I don't do it.
This eliminated about 70% of traditional maintenance tasks and reduced website issues by 60%.
Automation That Actually Matters
Instead of automating everything, I automate only the things that prevent emergencies:
Daily automated backups with weekly verification
Uptime monitoring that actually alerts me (not just generates reports)
Form submission monitoring to catch broken contact/signup forms
The key insight: automate monitoring and recovery, not maintenance tasks themselves.
Critical Flows
Focus on user journeys that generate revenue or capture leads - test these weekly instead of checking technical metrics
Backup Verification
Most people backup but never test recovery - download and verify one backup file monthly to ensure it actually works
Business Impact Filter
Before any maintenance task ask: will this directly affect user experience or revenue? If no skip it completely
Emergency Automation
Automate monitoring and alerts for critical failures but avoid automating the maintenance tasks themselves
The results speak for themselves. After implementing this approach across 50+ client websites over three years:
Critical website failures dropped by 60% compared to sites following traditional maintenance schedules. The reason? We stopped introducing unnecessary changes that could break things.
Emergency maintenance calls decreased by 80%. When you focus on preventing business-critical issues instead of chasing technical perfection, emergencies become rare.
Time spent on maintenance dropped from 2-3 hours monthly to 15 minutes weekly. Founders could focus on growing their business instead of maintaining their website.
But the most important result wasn't quantifiable: peace of mind. Startup founders stopped worrying about their websites breaking because they knew they were monitoring what actually mattered.
One SaaS client put it perfectly: "I used to check our website obsessively because I was paranoid something would break. Now I sleep better knowing that if something important breaks, I'll know immediately, and if it's not important enough to break our business, it's not worth worrying about."
What I've learned and the mistakes I've made.
Sharing so you don't make them.
After three years of going against conventional maintenance wisdom, here are the most important lessons:
1. More maintenance often creates more problems. Every change you make is an opportunity to break something. If it's working, leave it alone.
2. Checklists create false security. Following a comprehensive checklist makes you feel productive, but it doesn't necessarily make your website more stable.
3. Business continuity beats technical perfection. Your users don't care if you're running the latest plugin version. They care if they can complete their intended actions.
4. Automation should reduce work, not create it. If your automated maintenance is generating more tasks for you to review, it's counterproductive.
5. Context matters more than best practices. A maintenance approach that works for an enterprise site might be overkill (or insufficient) for a startup.
6. Prevention is better than perfection. Focus on preventing catastrophic failures rather than maintaining technical perfection.
7. Time is your most valuable resource. Every hour spent on unnecessary maintenance is an hour not spent growing your business. Choose your battles wisely.
How you can adapt this to your Business
My playbook, condensed for your use case.
For your SaaS / Startup
For SaaS startups specifically:
Test signup and login flows weekly - these are your revenue generators
Monitor app integration endpoints - API downtime kills user experience
Automate trial expiration notifications - don't let technical issues cost conversions
For your Ecommerce store
For ecommerce stores specifically:
Test checkout process weekly - broken checkout = lost revenue immediately
Monitor payment gateway status - payment failures are business killers
Verify product page load times - slow pages kill conversion rates