“If you’re the linchpin… it gets really hard.” – Greg Moore

In this week’s episode, Carol Schultz sits down with Greg Moore (Founder & CEO of Fit3D and WAIR) to unpack the reality of running two companies at the same time—and whether it’s actually possible to grow both without becoming the bottleneck.

Greg explains how his businesses operate under one umbrella but function as completely separate entities, each demanding different teams, strategies, and attention. He breaks down the core challenge founders face when splitting time: growth slows the moment you become the center of every decision (“linchpin”). The conversation explores why building systems, delegating responsibility, and structuring time intentionally are critical if you want both companies to scale.

They also dive into the trade-offs most founders ignore—how dividing attention can limit growth, why one company could flourish faster with full focus, and why Greg admits he wouldn’t start two companies at once again unless they were properly capitalized. The episode closes with a practical look at how he manages both today through time blocking, communication systems, and separating strategy from execution roles.

• Splitting time between companies is possible—but not without trade-offs
• Growth stalls when the founder becomes the operational bottleneck
• Systems and delegation are essential to avoid being the linchpin
• One company can often grow faster with undivided focus
• Running two businesses requires structured time blocks and communication
• Founder-led roles (like sales) make splitting time even harder
• Proper capitalization changes everything when managing multiple companies
• Without systems, you’re managing chaos—not scaling businesses

00:06:29 The core challenge: leading two companies under one umbrella

00:06:57 Can you split time without teams competing for attention?

00:07:17 Adapting leadership: companies adjust to limited founder time

00:07:55 The reality: planning, communication, and constant coordination

00:08:13 Why your time is always split—and never enough

00:12:04 Founder lesson: why Greg wouldn’t start two companies again

00:12:44 The linchpin problem—and how it limits growth

00:13:05 When companies depend on each other financially

00:13:21 The 3 conditions required to run multiple companies successfully

00:21:54 Weekly workflow: balancing strategy vs execution across both companies

00:24:07 Working “in” vs working “on” the business

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