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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The consulting trap isn’t just a startup problem. I’ve seen it play out at established companies too.
At Progyny, we built custom fertility and family-building benefits for enterprise clients like Google and Meta. That customization is what grew the company past $1B in ARR. It started with a few large clients who needed something health plans couldn’t offer, and we delivered. The product was never really a product — it was a custom service that we got very good at.
Then we started moving downmarket. Smaller clients, less revenue per account, but we were still trying to give them the same white-glove experience. Our tech platform had been built around customization and wasn’t designed to scale that way. Operationalizing it for hundreds of smaller clients looked nothing like what we’d built for a handful of big ones.
Leadership wanted to productize. Clients expected the custom service that made us worth paying for. I was sitting in the middle of that as the product lead, trying to serve both realities at once.
This is the trap. The thing that made you successful becomes the thing you can’t move away from.
The way I’ve come to think about it, there are three versions of any company. The vision you hold internally. The actual product you’re shipping. What your customers think you are. When all three line up, something clicks. When they don’t, you’re in the trap.
If you’re feeling like you are in the trap, ask yourself:
What do we think we are?
What are we actually doing?
What do our customers think we are?
Back to Bob’s Story.
Bob Matsuoka never asked those questions — not at the moment it mattered. A series of small yeses, each reasonable in the moment, added up to a company he didn't choose to build. He never stopped to ask whether this was the company he wanted to build. By the time it was obvious, it was already decided.
A few things his story keeps making me think about:
The trap is more common than founders want to admit. It doesn't just happen in early-stage startups. I've watched it unfold at companies doing over a billion in revenue. The scale changes but the pattern doesn't.
Not deciding is still a decision. If you're not asking what kind of company you want to be, the market, your clients, and your revenue line will answer for you. You'll end up somewhere you didn't choose.
Founders have a vision, investors have a return timeline, and the business has a margin reality. Getting all three pointed in the same direction is the whole job and most teams never stop to do it.
What are we? What are we actually doing? What do our customers think we are? Those aren't hard questions. What's hard is sitting down to ask them before the answer is already written.
Next week: Chapter 2.4 | The Managed Exit Is Still a Win.
Why the binary mindset of success or failure was the problem from the start.
Find Bob at HyperDev on Substack or on LinkedIn
Where's the gap for you right now between what you're building and what you want to be building?
Would love to hear from you.
