953. Q&AF: Managing Multiple Businesses, Becoming Undeniable & Building Vs Operating Your Business

Can confidence be the quiet engine behind a business's next jump?

Here’s what stood out the most: a construction leader called in sounding like he’d built a machine, then immediately discounted his own work. That contradiction kept pulling at me. The speakers responded with a strange, blunt kindness — the kind that tells you the truth so you can stop lying to yourself.

Where grit meets strategy

The conversation feels like an old-school coaching session that got modernized for the era of automation. One caller described growing a division into an eight-figure operation, then fretted about splitting time and focus to help his kids launch a new venture. The answer? A two-track approach: claim the confidence you already earned and use capital strategically to collapse decades of learning.

That’s not motivational fluff. It’s tactical. Hire an experienced operator for the part you don’t know and keep advising from the chair. Yes, it costs money, but it buys back years. Listen to that for a second: time is often the most expensive thing you own.

Undeniability as a survival skill

Another pitch hit harder: if you’re an employee, you’re in a new economy where replaceability is the baseline threat. The remedy isn’t panic — it’s being unreplacable. Clean the bathroom, sell the most product, anticipate needs, and fix problems before they become problems. That’s not humility; that’s insurance.

Call it “undeniable employee” theory: nobody cuts the person they literally cannot run the business without. That standard changes how you show up every morning.

Leadership is slow, messy work

A younger caller running a small drywall and insulation crew wanted out of the trenches without losing control. The response was humane and surgical: stop doing everything. Teaching someone to carry weight means letting them drop it sometimes. Those mistakes are not failures but training moments that create ownership and pride. Coach like you would a kid learning a skill — patient, iterative, and with a long view.

• Micro-investments in people often scale better than micro-managing projects.
• Promote the right person carefully — the wrong pick fractures team chemistry.
• Culture is a product of the leader’s patience and the permission they give others to fail forward.

Vertical thinking and the CEO shortcut

There’s a recurring theme: expand by design, not by ego. The speaker suggested vertical integration for entrepreneurs who want adjacent revenue streams. For others who want to move into unfamiliar territory, hire a seasoned CEO to compress the learning curve. It’s an unglamorous idea — buy competence and buy time — but the payoff is measured in years saved and avoided mistakes.

Honestly, I didn’t expect such blunt arithmetic: paying for expertise can be cheaper than paying the tuition of repeated failure.

Tough love, but specific

The tone swings between hard-edged and oddly tender. When someone starts shrinking from their accomplishment, the response is to call them out: you’ve already done big things — own it. That kind of candid validation felt energizing. It’s a different kind of mentorship, one that says, I won’t coddle you, but I will remind you of what you’ve proven you can do.

Practical rhythms to adopt

There were small operational habits threaded through the bigger advice. Use one master task list that includes everything across ventures. Prioritize initiatives that create clear value. When training staff, break skills into incremental steps and celebrate competence, not just output. Paint the growth path for your crew so they see what’s possible.

Those are simple changes, but they compound.

What I’m still thinking about

What if more leaders treated hires like a time machine — a purchase that accelerates expertise? What if more workers chose indisputable usefulness over quiet entitlement? The episode left me thinking about how choice and confidence interact: when you choose to believe in your own past results, you make risk less terrifying. And when leaders choose to invest patience in people, small teams actually become durable.

There’s a quiet tension here between the desire to control and the necessity to delegate. The resolution isn’t perfect. It’s messy and iterative — a leadership apprenticeship that never really ends.

Reflecting on that makes me appreciate the rare combination of blunt advice and vulnerable storytelling. It’s one thing to tell someone to hire a CEO or to be indispensable. It’s another to hear real people wrestle with the fear of failure and the art of letting go, and to come out braver on the other side.