The Founder Your Business Actually Needs (Part 1 with Dave Munson)

Most leaders hit a moment when the business they built can’t keep growing through them alone.

Not because the work changes.

Because they have to.

The skills that got the company off the ground stop scaling. The instincts that worked when the founder was the bottleneck start producing the wrong outcomes. And the same person who built a thing from nothing has to learn how to lead a thing that no longer fits inside their head.

In this episode of Inner Work, MaryAnn Means-Dufrene sits down with Dave Munson, founder and CEO of Saddleback Leather Co., for an honest conversation about what that transition actually demands — and the inner work it takes to make it without breaking yourself in the process.

The Disruption: When You Can’t Outsource Your Own Business

Dave built Saddleback the hard way. From a sketched bag in Mexico, through years of sleeping on the floor of a $100-a-month apartment in Juárez with his black lab Blue, into a global brand with a hundred-year warranty and a factory that now produces leather interiors for Toyota.

For a long time, he ran the business by working in his strengths and outsourcing everything else.

Then a moment came that changed it.

“There was a time in the business — I can’t legally say the FBI got involved,” Dave said. “An important person I was working with… I had to run my own business. I had outsourced that. I was just working in my sweet spot.”

When the founder has to step back into the seat they vacated, what gets exposed isn’t usually the operations.

It’s the leader.

“I just felt like I can’t do it,” Dave said about leading his team.

That’s the disruption most founders don’t name out loud — the gap between the leader you are and the leader your business now requires.

The Inner Work: The Coach Who Built Confidence by Asking Questions

In 2013, Dave hired a coach named Larry. He thought he was hiring someone to give him answers.

He wasn’t.

“I would say, ‘Larry, what do I do here?’ And he would go, ‘Man Dave, that’s a great question. What do you think?’ And I’d go, ‘Oh, we should do A, B and D.’ He’d go, ‘Man, I like the way you’re thinking. That’s really smart of you, Dave.’”

For a long time, Dave thought Larry was being a tough coach.

Years later, he realized what was actually happening.

“I said, ‘You were building my confidence up, weren’t you, Larry?’ He goes, ‘Yep. You knew how to run the business.’”

The lesson sat next to a much harder one — the one about how leaders actually grow.

“A lot of times we’ll ask, ‘God, give me wisdom like Solomon.’ And I was expecting, I’d feel like a tingle in my spine and all of a sudden I’m wise. No. He’s like, okay — I’m gonna make it really uncomfortable. I’m gonna give you situations that are gonna be brutal, where you really have to trust me. And you’re gonna grow in wisdom from really painful situations.”

Confidence in a founder isn’t given by a coach.

It’s surfaced by one.

The Rebuild: The 70% Rule and the Two Questions That Changed Everything

The change Dave made wasn’t more delegation. He’d already done that to a fault.

It was learning two questions.

“Great leaders ask great questions,” Larry told him. “What do you think we should do? And by when?”

The first question gives the people closest to the work permission to lead. The second one closes the loop.

“By when do you think we can start that? By when will you know when we can have that done?”

The other shift was the 70% rule.

“He said, ‘If someone else can do it 70% as well as you can, let them do it.’ I started having him do things… and I was like, oh, that’s good. Oh, this is better than I would’ve done.”

But Dave is careful not to romanticize hands-off leadership. The same friend who’d run a $13 billion company told him bluntly that he hadn’t controlled enough.

“He said, ‘Dave, you fully delegated and walked away without follow-up. You need to micromanage more.’ He said, ‘They write books about people because they’re good leaders — if they get profit at the end of the year. If you’re not getting profit at the end of the year, you’re being too hands off.’”

Real delegation isn’t disappearing.

It’s clarity, structure, and follow-through that the people doing the work can actually trust.

What I Know Now: Wisdom Is Built in the Hard Decisions

Dave’s takeaway might be the most useful sentence a founder will hear this year.

“Make a decision, and then make it into a good decision.”

Not the right decision. The good one — the one you turn into a good one through what you do next.

“You grow in wisdom when you make bad decisions. If everything you ever do is a good decision, you never grow in wisdom. You may grow your bank account. But you never grow in wisdom."

He pointed to a sign one of his sponsored kids in Rwanda walked past every day at school.

If it’s easy now, it’ll be hard later.

If it’s hard now, it’ll be easy later.

That sentence might be the most accurate description of what scaling a founder-led business actually feels like — and the most honest answer to leaders who keep waiting for the easy path to start.

🎧 Listen to the full episode now!