Kedron Rhodes

Working IN your business keeps the lights on. Working ON your business builds your moat.

This distinction hit me hard this week as I reflected on the leaders I most admire—the ones who seem to navigate uncertainty with a kind of strategic clarity that others lack. They share a common discipline: they step back, assess, and make intentional choices about how their organizations create and deliver value. They don’t just react to market forces; they position themselves to benefit from them—and even shape them.

The challenge is that most of us get trapped in the urgent demands of daily operations. Customer issues, product launches, team conflicts—the tactical work that feels immediately important but rarely moves the strategic needle. Meanwhile, competitors who invest time in building systematic advantages—stronger culture, better financial intelligence, clearer positioning—slowly but steadily pull ahead.

I’ve been thinking about this through Roger Martin’s lens: strategy is fundamentally about making choices that create sustainable competitive advantage. But here’s what I’ve learned from 25 years in the trenches: sustainable advantage isn’t built through one brilliant insight. It’s compounded through consistent, intentional decisions about how you operate, lead, and innovate.

This week’s collection explores what that looks like in practice. From Y Combinator’s CEO reframing how we think about competitive moats, to insurance leaders building agile culture in conservative industries, to AI prototyping tools that are changing how teams test and learn—these stories share a common thread. They’re about leaders who refuse to accept “that’s how we’ve always done it” and instead ask, “How can we do this better?”

The question isn’t whether you have time to work ON your business. The question is whether you can afford not to.

Entrepreneurship as Permissionless 🚀

David Cummings captures something essential about entrepreneurial mindset when he describes “permissionless” as his favorite word in business. The term, borrowed from blockchain protocols, perfectly encapsulates what separates those who create competitive advantage from those who wait for it to be granted. Cummings argues that most people overestimate risk and underestimate opportunity, especially when seeking approval from decision-makers focused on well-worn paths. But here’s the strategic insight that resonates: the biggest opportunities often exist precisely because others are waiting for permission to pursue them. Whether you’re launching a new product line, entering an adjacent market, or reimagining your business model, the competitive edge often belongs to those willing to act without consensus. It’s a mindset that turns uncertainty from a barrier into a strategic weapon. (Check it out →)

🪏 Take it a bit deeper with these…

🧠 Strategic Intelligence

• YC CEO Garry Tan: “Moat is not a noun. It’s a verb” — Every insight you have is a depreciating asset, which means sustainable advantage comes from your ability to compound new insights over time, not rest on old ones. Even trillion-dollar companies like Nvidia must continuously innovate or watch competitors catch up.

• The Value of Ratios: How Smart Financial Metrics Drive Business Performance — This deep dive shows how one company freed up $854,781 in working capital simply by improving inventory turnover and accounts receivable management—no new customers required. It’s a masterclass in finding competitive advantage hiding in your own operations.

🎯 Organizational Agility

• How RLI’s CEO Builds Agile Culture in a Conservative Industry — RLI transformed from a single-product contact lens insurer to a diversified specialty insurance leader by building culture around three principles: ownership incentives, radical transparency, and normalized learning from failure. Their secret weapon? Every employee becomes an actual owner after one year, creating alignment that most companies only talk about.

🚀 Innovation Acceleration

• AI Prototyping: How 11 Real-World Teams Are Transforming Their Work with Lovable — From design sprints to job interviews to customer discovery, teams are using AI prototyping tools to go from concept to interactive demo in hours instead of weeks. What’s fascinating isn’t just the speed—it’s how tangible prototypes change the quality of feedback and decision-making. One team leader noted: “When it feels real, they are able to identify real risks.”

👋 Sign-Off

I have to confess something, while researching this week’s newsletter, I was struck by how much content feels… artificial. Not just AI-generated (though there’s plenty of that), but lacking the hard-won insights that come from actually doing the work. The tactical messiness, the strategic trade-offs, the human complexity of building something that lasts.

That’s why I’m drawn to voices like David Cummings, who’s actually built and sold multiple companies, or the RLI CEO who’s navigated real transformation in a regulated industry. These aren’t theoretical frameworks—they’re battle-tested approaches from leaders solving real problems with real constraints.

If you come across sources of genuinely human-written insights about strategy, leadership, or innovation, I’d love to hear about them. We’re in this together, sharing the real work of creating advantage. Let’s keep lifting each other up with authentic wisdom, not artificial intelligence.

Thanks for reading, and here’s to building something that compounds.

⁓ Kedron

P.S. Speaking of working ON the business—I’m constantly refining how I curate and synthesize these insights. If there’s a particular strategic challenge you’re wrestling with, or a type of content that would be especially valuable, hit reply and let me know. Your feedback helps me shape this into something genuinely useful for the leaders doing the hard work.