You're good at building.Hard part: keeping everyone on the same tech story.
I help founders make the tech calls that keep the company on one story—as a builder who's made them, and as an advisor in the room when they get expensive. Read by 1,700 founders and builders.
What I write about
I write about the founder-side of tech decisions: what to buy, what to build, what to skip, and what you will regret six months from now. Start with what I've written in Insights, browse by theme, or see the tools I use.
How I think
A few notes on the tech calls founders face—what to buy, build, skip, and what you’ll regret later.
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Insight: 20
My blind spots are my solution set
The 35 ideas I had already decided against became the well — discounted, not gone.
Aug 22, 2026
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Insight: 19
Blindspotting
Why noticing what you are not doing is harder than optimizing what you can see — builder mode, operator mode, and the missing capabilities AI makes easier to ignore.
Aug 8, 2026
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Insight: 10
Building a new feature is fun! 😢
Build mode feels like forward progress—but it's often lateral. The two-monkey problem, and how sales dopamine re-educates the builder brain.
Jul 10, 2026
Stephan Smith
I'm a fractional CTO and writer. I've felt the burn to get something moving, the thrill of high-growth rocket startups, and the pain of falling back to earth. I've raised money, built companies, and shut them down—including a Techstars Boston company. Today I help founders make the tech calls that keep the company on one story.
Read more →From people I've worked with
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“It's rare to find a CTO equally comfortable in both the boardroom and the trenches.”
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“He restored delivery cadence and helped us ship a critical initiative in 4 weeks.”
Work with me
I take on a small number of companies at a steady cadence. Sometimes I’m behind the throne—visible only to the CEO. Sometimes I’m in front of it—on a special project or initiative with the team. I build for and with them when that’s what the call needs. Either way: judgment when the tech decisions get expensive, not another full-time seat.
See how we might work together →Get the weekly note
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