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April 2026

Founder type failures

I wrote recently about two types of founders. The ones who find the problem, and the ones who figure out the best solution. Most startups that get to Series A and further have both types. -- Most of the startups I've mentored are led only by founders of the first type. They've confirmed a real problem, spoken to potential users and started building a solution they feel can fit. Earlier they used to have agencies or their first engineer hires. Now they use AI tools. They've gotten the MVP out, and paying customers have started validating it. The problems start when they have to scale. There is massive technical debt embedded in the product. Along with that they now need internal systems for managing their teams, including CI/CD discipline to handle parallel features. The refactoring / redesign for scale results in a major rebuild. Inadvertant downtimes affect end users. I've seen early adopter customers walk away at this stage. The word-of-mouth pipeline suddenly dries up as the trust has eroded.

The second type fails differently. A founding team I mentored spent far longer than they needed to, going in circles. The product was well designed, and used a great scalable tech stack. But in hindsight, half the must-haves were missing and 80% of the nice-to-haves were implemented, sometimes at the cost of costly design decisions. Eventually, they had to rely on mentors and BD hires to help them shape the offering correctly. The cost to get there was about 4 months of day-and-night development time, which could have been avoided, had they brought in a founder of the first type early. -- These aren't dramatic failure stories. There are many others which don't get to these stages. But the cost in both cases is time and trust, and rebuilding with investors and customers is slow, hard work.

The best teams I've seen had both types in the room before the first line of code was written.

Who's covering the side you don't naturally occupy?

#Startups #Founders #Leadership

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