The Systems, Speed, and Strategy Behind Great Founders
Hey there,
Welcome back to Founder Mode!
I’ve thought a lot about what makes good founders different from great ones. It's not just about those who gather funds or attract press. It’s also about the people who create real changes in how we work and live.
Before we continue, I’ll share what we learned at our Founder Mode Live event in San Francisco Tech Week. We talked to Max Mullen at Instacart and Andrew Ofstad at Airtable. Both have created products used by millions. They shared openly about the tough choices that led to their success. We discussed when to say no, why quick moves can slow you down, and how to create systems that grow. Max shared how the early experiments at Instacart shaped their approach. Andrew shared how Airtable strikes a balance between flexibility and structure. Have you ever wondered how top founders make tough choices? If everything feels crucial, this episode is one you can't miss. You can catch the full podcast below.
Now let's dive into the topic. Last week, I reviewed talks with some great founders. What amazed me wasn’t their great ideas or huge funding rounds. It was how they think about problems. How they decide when everything seems urgent. How to create systems that grow without failing.
Today, I want to share what I learned. These aren't abstract theories. These are practical patterns I've seen work again and again.
Strategy Before You Build Anything
Here's where most founders get it wrong.
They have an idea. They get excited. They quickly begin hiring and developing features. Six months later, they wonder why nothing feels right.
Great founders do something different. They fall in love with the problem first.
Not the solution. Not the technology. The problem itself.
I saw a founder who spent three months talking to customers. Only after that did they write any code. Her team thought she was wasting time. "When do we start building?" they asked.
She told them: "We are building. We're building our understanding."
Once she began making the product, things moved quickly. She knew exactly what to make. She knew who would use it. She knew why they'd care.
This is what I mean by strategy before structure. You need to define how you'll win before you decide what you'll build and who will build it.
Most people do this backward. They gather resources, then figure out what to do with them. It's like picking up ingredients before figuring out your dish. You end up with a weird meal nobody wants to eat.
Start with the problem. Understand it deeply. Fall in love with it. Then build your organization around solving it.
Saying No to Great Things
This one hurts.
You have ten opportunities in front of you. Eight of them are pretty good. Two are extraordinary.
Most founders try to do all ten. They stretch themselves thin. They move slowly on everything and quickly on nothing.
Great founders make a different choice. They say no to the eight good opportunities so they can say yes to the two extraordinary ones.
I know what you're thinking. "But those eight opportunities are still valuable! Why would I turn them down?"
Because you have limited time and energy. That's just reality.
Think about it like this. You have 100 units of energy per week. If you split them across ten projects, each one gets 10 units. That's not enough to make real progress.
But if you focus on two projects, each one gets 50 units. Now you're moving fast. Now you're making real impact.
The hard part isn't identifying good opportunities. The hard part is admitting that good isn't good enough anymore.
One founder I know turned down a partnership with a major company. Everyone thought he was crazy. The partnership would bring in more revenue and improve credibility.
But he knew it would distract his team. It would distract them from the amazing thing they were creating.
Six months later, that amazing change reshaped their business. The partnership he turned down? That company called him back. They offered better terms.
This is the power of focus. When you do fewer things, you do them better. When you do them better, more opportunities come to you.
The bar isn't good versus great anymore. It's great versus extraordinary.
Moving Fast and Learning Faster
Speed matters in building products. But not the kind of speed most people think about.
It's not about shipping features quickly. It's about learning quickly.
Let me explain what I mean.
Imagine two teams working on AI products. Team A carefully plans four experiments. They spend weeks perfecting each one. They ship all four. Two work, two don't.
Team B runs 100 quick experiments. Most fail. But they find 5 to 10 that show real promise. They double down on those.
Which team wins?
Team B. Every time.
This is what I call velocity with clarity. You're moving fast, but you know what you're looking for. You're not just throwing things at the wall randomly. You have a hypothesis. You test it. You learn. You adapt.
The key is focusing on outcomes, not outputs.
Outputs are what you ship. Outcomes are what you learn.
Most companies celebrate outputs. "We shipped 20 features this quarter!" they say proudly.
But did those features teach you anything? Did they change user behavior? Did they prove or disprove your hypotheses?
That's what matters.
I spoke with a founder who conducts experiments in a unique way. His team doesn’t define success by whether features work. They measure success by what they learn.
If an experiment fails, but they learn something important, it's still a win.
If an experiment succeeds but teaches nothing new, it’s less valuable.
This mindset changes everything. It removes the fear of failure. It encourages bold experiments. It creates a culture where learning is the goal, not perfection.
In fast-moving fields like AI, this method is key. The technology changes every month. To keep up, you need to experiment often and learn faster than others.
Building Systems That Fix Themselves
Many people don’t grasp how automation works.
The first level of automation is making things run without humans. That's valuable.
The second level is making things run better without humans. That's exponentially more valuable.
Let me give you an example.
You create an AI system to handle customer requests. Great. It works 90% of the time. The other 10%? A human has to step in and fix it.
Now imagine the same system, but it can detect when it's failing. It knows when something isn't working right. And it adapts without anyone telling it to.
That's self-healing automation.
This is where the real value lives. Not in systems that operate alone, but in systems that enhance on their own.
Think about your phone's autocorrect. It learns from your typing. It gets better over time. You don't have to train it manually.
That's self-healing automation at work.
Now apply this concept to business systems. Customer service. Data processing. Quality control. What if these systems could find and fix issues before anyone saw them?
One company I studied built a monitoring system for their AI products. When the system spots unusual patterns, it alerts the team. It keeps trying different methods until it finds one that works.
This creates massive leverage. One engineer can manage systems that usually need an entire team.
The catch? Building self-healing systems is hard. It requires thinking differently about problems. You're not just solving the immediate issue. You're creating systems to tackle problems you haven't thought of yet.
But that's what separates good technology from transformative technology.
Speed Versus Scale: The Startup Paradox
People love comparing startups to large companies. They say startups move faster. They're more innovative. They take bigger risks.
That's all true. But it misses the deeper point.
The difference isn't about capability. It's about context.
Let me explain.
A startup can try 50 different ideas to see what works. If 49 fail and one succeeds, that's great. That one success can build the whole company.
A large company can't do this. They need solutions that work for millions or billions of people. They can't afford 49 failures for one success.
It's not that large companies are slow or risk-averse. They're optimizing for a different outcome.
Think about it like this. A startup is exploring territory. They're looking for treasure. They can dig 100 holes. Most will be empty. Finding just one treasure chest covers all costs.
A large company is building highways. They can't build 100 highways to see which one people use. They need to get it right the first time.
This changes everything about how you operate.
In a startup, you throw ideas at the wall. You test fast. You fail fast. You learn fast. Your goal is to find what works.
In a large company, you aim carefully. You test thoroughly. You plan extensively. Your goal is to scale what you know works.
Neither approach is better. They're just different.
The issue arises when people mix up the two contexts. Startups that mimic big companies lose their key edge: speed and experimentation. When big companies try to act like startups, they create chaos.
The best founders understand this. They know what game they're playing. They know what winning looks like in their context.
Early stage? Move fast. Try everything. Learn constantly.
Growth stage? Start focusing. Build systems. Think about scale.
Mature stage? Optimize. Perfect. Reach billions.
Each stage needs unique skills and mindsets.
Five Key Takeaways
Let me break down the most important lessons here:
1. Fall in love with problems, not solutions. First, understand the problem. Then, think about how to solve it. Great strategies stem from a strong grasp of the problem. Focus your organization on the problem, not the reverse.
2. Protect your focus like your life depends on it. Every yes to a good opportunity is a no to an extraordinary one. You have limited energy. Spend it on things that matter most. Learn to say no to great things so you can say yes to extraordinary things. This is hard, but it's necessary.
3. Measure what you learn, not just what you ship. Run more experiments. Focus on outcomes over outputs. Ask what each experiment taught you, not just whether it worked. Speed matters, but learning matters more. Velocity without clarity is just chaos.
4. Build systems that improve themselves. The future belongs to automation that adapts. Create systems that detect their own failures and fix them. This adds more value than systems needing constant human care. It's harder to build, but worth the investment.
5. Match your approach to your context. Startups and large companies play different games. Early stage means exploration and rapid experimentation. Later stages mean optimization and scale. Don't confuse the two. Know what game you're playing and play it well.
Final Thoughts
Here's what I keep coming back to.
Making something amazing isn’t only about having the top idea. It's not about raising the most money. It's not even about being the smartest person in the room.
It's about making better choices again and again, over time.
Every founder faces the same challenges. Limited resources. Competing priorities. Uncertain markets. Self-doubt.
Great founders stand out by how they tackle challenges.
Do they focus or spread themselves thin?
Do they learn from experiments or just ship features?
Do they build systems that scale or systems that break?
Do they understand their context or copy what others do?
These choices compound. Small decisions can lead to big changes in results over time.
The good news? You can learn these patterns. You can train yourself to think this way. You can build better systems and make better choices.
Start small. Pick one area from this newsletter. Maybe it's learning to say no to good opportunities. Maybe it's running more experiments. Maybe it's building one self-healing system.
Focus on that one thing. Practice it. Get good at it. Then add another.
That's how great founders are built. One decision at a time. One system at a time. One lesson at a time.
The journey is long. But it's worth it.
See you on Friday,
-kevin
P.S. What resonated most with you from this newsletter? Hit reply and let me know. I read every response.
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