Where Growth Breaks: Lessons From Building AI in the Real World
Welcome back to Founder Mode!
Lately, I’ve been thinking a lot about where growth actually breaks. Not on the charts. Not in pitch decks. But inside the system itself.
At Pretty Good AI, we spend our days building AI for real businesses. Not just demos. Not hype. Real operations with real customers have real consequences if things go wrong. The deeper we dive, the clearer it gets: the biggest chances in AI are also the toughest.
The founders who are winning right now are not chasing headlines. They are doing the unglamorous work. They are creating trust layers. They chose control instead of capital. They solve problems that many prefer to ignore.
I see some patterns that are shifting how I view AI, services, and scalability.
The Human in the Loop Is the Moat
There is a lot of talk about AI replacing everyone. In practice, that is not what works in high-stakes industries.
In healthcare and other sensitive services, the winning model is not full automation. It is AI that is good enough to handle most cases, backed by a highly trained human safety net.
At Pretty Good AI, we see this every day. When the AI handles the routine work, speed and efficiency go up. If something emotional, complex, or unexpected happens, it’s okay to switch to a human. That’s not a failure. It is the product.
The technology accelerates the workflow. The human earns the trust. Together, they close the loop.
Pure automation breaks trust. Human-backed automation builds it.
Second-Time Founders Are Playing a Different Game
I’ve noticed a shift among experienced founders. Many of them could raise large venture rounds tomorrow. They choose not to.
After building and exiting companies, they have seen what growth at all costs really costs. Board pressure. Artificial metrics. Short-term decisions that hurt the product.
Instead, they are bootstrapping with small, elite teams. They want full control. They want to build something durable, not disposable.
At Pretty Good AI, this resonates deeply. When you are not answering to a board, you can slow down when quality matters. You can say no to bad customers. You can build for the long term.
Capital is a tool, not a strategy. Control gives you room to think.
The Tech Is Easy. The Implementation Is the Product
You can spin up an impressive AI demo in an afternoon. That part is no longer hard.
What is hard is deploying it inside a real business.
At Pretty Good AI, we face issues like outdated servers, missing encryption keys, and faulty workflows. Also, we have years of manual fixes that no one documented. None of that shows up in a demo. All of it shows up in production.
The startups winning right now are not the ones with the flashiest models. They are the ones willing to do the messy work. Cleaning data. Mapping workflows. Sitting with operators to understand how things actually run.
AI does not fail because it is not smart enough. It fails because the environment around it is broken. Fixing that environment is where real value lives.
Date Before You Marry Your Partners
Strategic partnerships look great on paper. In reality, they often stall progress.
I have learned that the best way to test a partnership is not a contract. It is execution.
Skip the complex reseller or joint venture agreements. Just seek out one tough customer. Try to launch them together in thirty days.
Shared pressure reveals everything. How decisions get made. How fast people move. How they handle problems.
At Pretty Good AI, this approach has saved us months of legal work and helped us avoid the wrong partnerships early. One shared win or one shared failure tells you more than any slide deck ever will.
Where Growth Actually Breaks
Growth usually breaks at the seams.
It breaks when automation removes too much humanity. It breaks when capital replaces discipline. It breaks when tech is built without respect for reality. It breaks when partnerships are chosen for optics instead of execution.
What holds growth together is not speed alone. It is trust, control, and a willingness to do the hard work others skip.
This is where Pretty Good AI keeps its focus. Not on being the loudest, but on being the most reliable.
5 Key Takeaways
- Human in the loop builds trust. AI should accelerate work, not remove accountability.
- Control beats capital. Small teams with ownership build better products.
- Implementation is the real moat. Cleaning up messy systems is where value is created.
- Test partners through action. One shared launch beats a hundred meetings.
- Growth breaks at the seams. Fix the system before scaling it.
Final Thoughts
The next wave of AI companies won’t succeed by replacing people or just seeking growth. They will succeed by mixing technology with human judgment, discipline, and hard work.
At Pretty Good AI, every hard lesson keeps reinforcing the same idea. The most valuable work is often the least glamorous. That is where trust is built. That is where growth holds together instead of breaking apart.
If you are building in AI or services right now, my advice is simple. Go where it is uncomfortable. Solve the problems no one wants to touch. That is where the real opportunity lives.
See you on Friday!
-kevin
Recent Social Posts
Recent Podcasts
2810 N Church St #87205, Wilmington, DE 19802
Unsubscribe · Preferences
