In this episode of Constructive Interference, Rufus sits down with JT Wiederholt for a conversation shaped by years of building, leading, and watching businesses evolve over time.

They talk through moments many business owners recognize—when responsibility shifts, when decisions start carrying more weight, and when the role you play inside your own company no longer looks the way it used to.

The Role Keeps Changing

Early on, the work is clear. You’re close to everything. You’re involved in the details. You’re the one pushing things forward.

As a business grows, that proximity changes. Rufus and JT talk about how founders often feel that shift before they fully understand it. More people are involved. More is at stake. And the work begins to look less like execution and more like stewardship.

It’s not always obvious when that transition starts—but it’s felt.

Experience, Not Theory

JT draws on decades of working alongside business owners, including leaders of multi-generation family companies. He shares stories about watching founders wrestle with control, trust, and responsibility as their businesses mature.

The conversation moves naturally across leadership, profit, succession, and failure—not as isolated topics, but as realities that tend to surface together over time.

Rufus reflects on moments from his own journey, including shifts in how he thinks about growth and profitability, and how those shifts changed the way he leads and invests in his business.

Failure as Part of the Process

Another thread that surfaces is failure—not as something dramatic, but as something ordinary. Rufus and JT talk about the instinct to protect people from mistakes, and how that instinct can shape teams in ways leaders don’t always intend.

There’s an acknowledgment that learning often happens through experience, and that leadership involves deciding where to allow space for that experience to happen.

A Long View Conversation

This episode stays focused on perspective. On patterns seen over time. On the moments business owners tend to encounter as what they’re building grows more complex.

It’s a conversation rooted in lived experience, shared observations, and the long view of leadership—one that doesn’t rush to conclusions, but invites reflection.

Key Takeaways

Growth often changes a leader’s role before they consciously recognize it
Many founders feel the tension of shifting responsibility long before they can name it
Profit and growth come up as recurring reference points, not objectives in isolation
Letting go of control is a recurring challenge as businesses become more complex
Failure shows up as part of learning, especially when developing people over time
Long-term perspective becomes harder—and more necessary—as more is at stake

💬 Guest: JT Wiederholt

📍 Host: Rufus Cressend, Constructive Interference

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