My Biggest Failures of 2024: A Post-Mortem

Failure 1: The AI Legal Bot (The 'Cool Tech' Trap)

We built a bot to summarize legal contracts. The tech was amazing. It used GPT-4, Pinecone for vector search, and a beautiful React frontend. It could summarize a 50-page NDA in 30 seconds.

Why it failed: I forgot to ask one question: *"Who buys this?"*

We pitched it to law firms. They hated it. Why? Because lawyers bill by the hour. If a Partner bills $500/hr and spends 5 hours reviewing a contract, that is $2,500 revenue. If our bot does it in 10 minutes, they can only bill $100.

We were trying to sell 'Efficiency' to an industry incentivized by 'Inefficiency'. Our product cannibalized their revenue model. They nodded politely and never called us back.

Lesson: Incentives > Technology. Always map the money flow before you write a line of code. If your product loses your customer money, you will fail.

Failure 2: The Gig Marketplace (The 'Liquidity' Trap)

We tried to build a platform for gig workers in construction ('Fundis'). We wanted to be the 'Uber for Plumbers'.

Why it failed: We couldn't seed the liquidity. - Supply Side: Fundis didn't have smartphones often enough, or data was off. They missed notifications. - Demand Side: Site managers preferred phone calls. They trusted their existing network.

We tried to digitize trust too early. The market ran on 'referrals' ("I know a guy who knows a guy"), not 'star ratings'. A 5-star rating on an app meant nothing compared to a recommendation from a cousin.

Lesson: Don't replace a phone call with an app unless the app is 10x better. For construction, the phone call was fast, free, and trusted. Our app was slow, required data, and lacked social context.

Failure 3: Hiring for Potential, Not Proof (The 'Nice Guy' Trap)

I hired a 'Junior' with great potential to lead a critical project. They were smart, eager, and cheap. I thought: "I can mentor them."

They drowned. The project had complex architectural decisions (Microservices vs Monolith) that they had no context for. They made bad decisions early on that cost us 3 months of refactoring later.

It wasn't their fault; it was mine. I put a lightweight in a heavyweight ring.

Lesson: In a startup, you don't have time to train. You need people who have done it before. - 'Potential' is for Google/Microsoft with big L&D budgets and 2-year ramp-up times. - Startups need 'Proof'. You need mercenaries who hit the ground running on Day 1.

Conclusion

Failure is tuition. I paid about $150,000 in 'tuition' in 2024 across these projects. Expensive? Yes.

But the lessons are burned into my brain. I will never again build against incentives. I will never again force an app where a phone call works. And I will never hire for potential in a crisis.

If you aren't failing, you aren't trying hard enough. Just fail cheaper next time.