The Blog

Entrepreneurship

Hard-won lessons from co-founding 6+ startups across 3 continents, on co-founder dynamics, product decisions, hiring engineers, and going from 0 to paying customers. On-site and Medium, all in one place. Back to the blog.

What Does a CTO Do in a Startup? The Role at Every Stage, From Someone Who Has Done It Six Times

A startup CTO owns every technical decision the company cannot afford to get wrong: what to build, how to build it, who builds it, and how it stays secure. The job changes completely with stage. Here is what a CTO actually does at pre-seed, seed, Series A and beyond, the core responsibilities, how the role differs from a VP of Engineering, and when you need one.

·10 min read

Technical Co-Founder Equity Splits: What's Fair in 2026

If a technical co-founder is building the entire product and you are pre-revenue, the defensible range is 40 to 50 percent of the founder pool. Here is what actually moves that number, why vesting matters more than the split, and the three patterns that turn a fair deal into resentment.

·10 min read

What Is a Fractional CTO? The Role, Explained by One

A fractional CTO is a senior technology executive who leads your engineering part-time, typically 2 to 3 days a week, for a fraction of a full-time CTO's cost. Here's what the role actually involves, what it doesn't, and how to tell if you need one. Written by someone who does this for a living.

·8 min read

Case Study: The EdTech Problem So Hard We Built Our Own OS for It

Every technical person who looked at this problem walked away. It needed Linux, MERN, DevOps, Python, AI, security, and custom protocols in one head. Here's how we built it, went from processing thousands to 500,000 assessments in an hour, the one wrong AWS line that almost sank the launch, and why competitors now keep calling.

·9 min read

Why Hire a Fractional CTO (and When You Shouldn't)

Every fractional CTO's website tells you why to hire one. Almost none of them tell you when not to. I have been on both sides of this decision six times as a founder and I am not going to sell you a retainer you don't need. Here is the honest version.

·10 min read

CTO Interview Questions From Someone Who's Hired for Six Startups

Most CTO interview question lists are written by recruiters who have never hired one. I have hired technical leaders for six companies I co-founded and been the candidate on the other side of this table more times than that. Here are the questions that actually separate a strong CTO from someone who interviews well.

·11 min read