Founder Insights and Contrarian Takes
Welcome back to Founder Mode!
The more we develop Pretty Good AI (PGA for short), the more I see that most founders aren’t failing due to competition. They’re losing because they’re using the wrong playbook. Standard startup advice may seem wise, but it can lead you astray.
The founders who win today are the ones who look at a messy problem and say, “I want that one.” They ignore the trends. They ignore the noise. They focus on what brings real leverage. They also stay close to the truth, even when it feels uncomfortable.
Here are a few lessons that shaped my thinking this week. These came from talks with other operators, seeing what doesn’t work in the market, and building PGA as we went.
Solve the Hardest Technical Problem First
When we started PGA, people told us to start simple. Build a text product. Build a lightweight chatbot. Build the “easy” version first.
But I kept seeing the same thing across the AI space. The companies that tried the easy stuff first ended up trapped. Their “easy” interface became their ceiling. They didn't develop the skills to handle key business challenges.
So we went the opposite direction. We took on real-time voice with sub-second latency. Voice that sounds like a human. Voice that works in chaotic environments. Voice that plugs into regulated industries.
It was brutally difficult. Now that we’ve overcome the toughest wedge, the rest feels much easier. When you own the interface that everyone else avoids, you own the intelligence layer that sits behind it.
Most companies go around the mountain. We went straight up.
Capital Is Not a Strategy
I used to think large funding rounds signaled momentum. After seeing it up close, I now believe that big money often slows teams down.
At several conferences, I saw unicorns come in with smaller teams. Their product speed was slower. They had a smaller number of customers than the lean teams that worked quietly. Many companies collect a lot of money before showing their worth. They focus more on their image than on improving their product.
At PGA, we made our best decisions by acting like owners instead of spenders. We built a working product in months, not years. Lean teams can move faster than larger teams when funds are tight.
Capital helps you scale. It does not help you think.
The Bad Service Optimization
This one surprised me.
Not every customer wants better service. Some legacy businesses like to use long hold times and voicemail. It forces their volume to spread across the day. Faster service does not help them. It exposes their staffing issues and shrinks their margins.
I once pitched a company on reducing call volume. Their response was simple. “If you do that, my boss will cut my staff.”
That moment changed the way I sell PGA. Not every customer is optimizing for experience. Some are optimizing for throughput. Before selling a quality product, see if the customer values quality.
A better product is not always a better fit.
The Binary Marketing Budget
The more I try new things, the more I think early-stage B2B marketing needs one simple rule.
Spend freely when you can track money spent on meetings and pilots. Spend zero when you cannot.
Branding has its place, but not before product market fit. The fastest way to burn money is to chase awareness before you chase revenue.
At PGA, we only invest in channels where we know the cost per booked meeting. If money goes in and meetings come out, we scale it. If not, we kill it instantly. No debate.
Early stage isn’t the time for complex marketing dashboards. It is time for simple math.
Turn AI Fear Into Greed for Partners
Many consultants and agencies are anxious that AI will cut into their billable hours. If you sell to them directly, they resist.
Change the incentive structure, and everything shifts.
When we talk with partners now, we frame PGA as a profit engine they can leave behind. They don't bill by the hour. They install our AI and earn ongoing commissions. Suddenly, AI is not a threat. It is a second income stream.
Fear becomes greed. Resistance becomes motivation. Your partner becomes your distribution network.
This is one of the most overlooked growth strategies in AI right now.
Five Key Takeaways
- Start with the hardest problem. Hard problems create real moats and long-term leverage.
- Capital does not equal progress. Disciplined small teams outperform large teams that are burned out.
- Know what your customer values. Do not sell premium service to a business that cares only about volume.
- Marketing is binary. Spend only when you can track spending to meetings.
- Reframe partner incentives. Turn AI fear into partner upside by giving them recurring revenue.
Final Thoughts
Building PGA shows me that many founders pursue the wrong goals. They chase features. They chase funding. They chase attention. But the winners keep it simple.
They solve the problem others avoid. They stay close to customers. They use their size as a weapon, not a weakness. They build in a way that earns trust month after month.
I believe more each week that the next wave of AI companies won’t be those with the biggest checks. They will have the best insights and the clearest reasons to act.
See you on Friday,
-kevin
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