I wrote a 20,000 word Notion guide on what I would do differently as a founder if I were to start from scratch
Covers equity, fundraising, raising money, taxes, hiring & paying my team, running finance, selling secondaries & exiting
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Unpopular opinion: Monitoring is the new technical debt.
Startups now have so many different monitoring tools.
Grafana for metrics.
DataDog for APM.
Sentry for errors.
CloudWatch for AWS.
New Relic for synthetics...
They spend more time monitoring their monitoring than fixing…
why every saas company needs 3-5 devops engineers NOW:
2010: upload to heroku
2024: k8s + service mesh + blah blah...
2025: MORE PAIN?
ARE YOU KIDDING ME?!
complexity is KILLING us.
SIMPLICITY, NOW.
Startup infrastructure evolution:
Month 1: 'Let's keep it simple'
Month 6: 'We should probably use Docker'
Month 12: 'Maybe we need Kubernetes'
Month 18: 'Why do we have 47 monitoring dashboards?'
Month 24: 'Can we go back to simple?'
Infrastructure complexity: It's like entropy…
every new devops tool adds:
$50K/year in licensing
20 hours/month in maintenance
3 days onboarding per new hire
1 more dashboard to check during incidents
another integration to break
most startups use 10+ devops tools.
do the math.
IT'S A NIGHTMARE.
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