// Topic
Startups
Definition
Startups coverage in this archive spans 13 posts from Jan 2016 to Mar 2026 and links technical decisions to margin, distribution, and execution durability. The strongest adjacent threads are engineering, ai, and leadership. Recurring title motifs include ai, security, startup, and startups.
What the archive argues
- The posts consistently push for explicit unit economics and practical tradeoffs over narrative hype.
- Early posts lean on security and microservices, while newer posts lean on ai and engineering as constraints shifted.
- This topic repeatedly intersects with engineering, ai, and leadership, so design choices here rarely stand alone.
Execution checklist
- Tie roadmap bets to measurable outcomes: cost, throughput, risk reduction, or revenue impact.
- Start with the newest post to calibrate current constraints, then backtrack to older entries for first principles.
- When boundary questions appear, cross-read engineering and ai before committing implementation details.
Common failure modes
- Treating technical strategy as branding instead of an operating constraint.
- Running broad experiments without clear stop conditions or budget discipline.
- Applying guidance from 2016 to 2026 without revisiting assumptions as context changed.
Suggested reading path
- Start here (current state): AI Startup Landscape 2026
- Then read (operating middle): What I Learned Scaling an Engineering Team
- Finish with (foundational context): Why Microservices Aren’t Always the Answer
Related posts
- AI Startup Landscape 2026
- Stop Starting With the Model: AI Product Strategy That Works
- Most AI Startups Are Wrappers. That’s the Problem.
- Leading Engineering Teams When Nobody Knows What Is Next
- Your Incident Response Plan Is Useless Until Someone Bleeds
- Your Cloud Bill Is Lying to You: A Cost Optimization Comparison
- What I Learned Scaling an Engineering Team
- Your Startup Doesn’t Need a Security Team. It Needs a Security Champion.
References
13 posts
- AI Startup Landscape 2026
By early March 2026, the AI startup market looks less like a gold rush and more like a durable industry with clear pressure points. This post lays out where leverage sits, what buyers reward, and what durable execution looks like now.
Stop Starting With the Model: AI Product Strategy That Works
Every roadmap I've seen this quarter has an AI feature. Most of them start with the wrong question. Start with the user problem, not the model.
Most AI Startups Are Wrappers. That's the Problem.
Everyone has an AI startup now. Having been through two accelerators and founded two companies, I can tell you: most of these will not survive the year.
Leading Engineering Teams When Nobody Knows What Is Next
Uncertainty is not new for startups, but 2023 brought it to every engineering org. Here is what actually helps.
Your Incident Response Plan Is Useless Until Someone Bleeds
Most incident response plans are shelf-ware. Here's what actually matters when your infrastructure is on fire -- drawn from real breaches, NATO cyber exercises, and startup chaos.
Your Cloud Bill Is Lying to You: A Cost Optimization Comparison
A direct comparison of cloud cost optimization strategies -- what actually moves the needle vs. what just makes finance feel better.
What I Learned Scaling an Engineering Team
Lessons from growing an engineering org at the fintech startup -- what breaks, what works, and why clarity beats process every time.
Your Startup Doesn't Need a Security Team. It Needs a Security Champion.
You can't afford a security team at a startup. But you can turn one motivated engineer per squad into a security champion — and that changes everything.
The CTO's Guide to Technical Due Diligence
I've been on both sides of technical due diligence -- raising money and evaluating companies. Most of what people worry about is wrong. Here's what actually matters.
Hiring Engineers When You Can't Compete on Salary
You cannot outpay Big Tech, but you can outshine it on impact, growth, autonomy, and clarity. This is how to hire great engineers with a startup offer in 2016.
The Real Cost of Running Your Own Servers in 2016
Most startups have no business running their own servers. The math is not close.
Security Incident Response for Startups
A practical incident response playbook for small teams: define incidents, assign owners, contain fast, investigate calmly, and recover with clear communication.
Why Microservices Aren't Always the Answer
Most teams adopt microservices too early and pay for complexity they don't need yet. A well-structured monolith is faster, simpler, and keeps your options open.