Bob Matsuoka is the CTO of Duetto, a revenue management platform used by around 8,000 hotels. Before that, he spent nearly eight years at Tripadvisor, eventually running a 550-person engineering org as Interim CTO. He led the company's first GenAI features and oversaw a full rebuild of a product stack that had been running on legacy code for two decades. Earlier, he was CTO of Citymaps, which Tripadvisor acquired for ~$30M in 2016. Before any of that, he founded RunTime Technologies in 1995 and ran it for more than a decade.
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I’ve been thinking a lot about decisions lately. Specifically, why some are easy and some keep you up at night.
If one option is clearly better, it’s not really a decision — you just do it. And if one outcome is obviously bad, that clarity also forces your hand. The hard decisions are when both options are roughly equal. Good enough on one side, not quite right on the other, and no obvious way to break the tie.
With Bunnii, our decision to shut down eventually became clear because the bad outcome got undeniable. But for most founders, it’s never that clean. You’re sitting in the gray zone, weighing two options that feel about the same.
Ruth Chang’s work on hard choices helped me understand why. Her argument is that most decisions feel hard because the options really are on par. Not clearly better or worse, just comparable in ways that don’t reduce to a single answer.
Here’s a tactical framework for when you’re stuck:
Check if it’s actually a hard choice. If more time or more information would resolve it, it’s just an unresolved one. A genuinely hard choice stays hard even after you’ve done your research.
Stop trying to optimize. The pros/cons list will loop forever. At some point, the cost of not deciding is higher than the cost of a slightly imperfect call.
Ask who you want to be, not which option is better. Each path represents a different version of you. The question isn’t what’s objectively right — it’s what’s right for the person you want to become.
Commit without second-guessing the road not taken. Once you’ve chosen, you chose. Counterfactuals will eat you alive. Chang’s point is that meaning comes from making a choice that reflects who you are, not from finding the “correct” answer.
Back to Bob’s Story.
Bob describes his hard decision in the episode. Because they were cash flow positive-ish, the decision to step away was hard. Stay and deal with the fallout, or keep going because you’re surviving. This hard decision contributed to him staying longer than he should have.
A few things his story keeps making me think about:
“Ish” is the sign you’re in survival mode and the gray zone. It keeps you alive but also keeps you stuck.
The founder trap Bob describes, where the only measure of success is “keep going,” means there’s no such thing as winning. And the decision becomes a character question, which makes it even harder to make.
They didn’t know what to measure because they didn’t know. This is big for first-time founders because you’re usually just rolling with it until you hit a wall.
It’s usually never about capabilities. Founders are the most capable people I have ever met. But it feels like an attack on your capabilities when success is defined by a personal value (keep going) vs. an outcome.
Next week: Chapter 2.3 | The Consulting Trap
When clients are paying for a service and not your product — and that slowly becomes the whole business.
Find Bob at HyperDev on Substack or on LinkedIn
How do you define what winning looks like?
I’d love to hear what people are doing?
