Episode 2 — The First Time I Knew I’d Screwed Up

The Leap

In early 1996, just months after leaving a six-figure job, I did what many first-time entrepreneurs do.

I bet on myself.

I poured most of my savings into a new company — Custom Cuts Printing (what would later become MDT Marketing) — built around an idea I believed deeply in: die-cut advertising inserts.

I had spent nearly a decade in marketing and printing sales. I knew inserts worked. My intuition told me cutting them into shapes would improve response.

What I didn’t know yet was how little intuition matters when execution fails.

What I Thought I Knew

On paper, the plan made sense.

But several critical realities were already stacked against me:

• I had six months of cash, at best
• I had no experience running production
• I had no margin for mistakes
• I was dependent on a production partner whose equipment and capabilities I didn’t fully understand

I wasn’t reckless — but I was inexperienced.

And that gap matters.

The First “Oh Sh*t” Moment

Three months in, I sold my first major order: 1,000,000 die-cut inserts for Little Caesars, scheduled to be delivered statewide within weeks.

Before production ramped up, I stopped by the printing plant.

What I saw stopped me cold.

One pressman. Stacks of inserts piled haphazardly. And printing that was completely unacceptable.

Images were tinted different colors — green, blue, red — all over the same job. The plant simply did not know how to produce what I had sold.

To make matters worse, my partner and his father — who owned the plant — were on vacation.

I was three months into business. My savings were disappearing. My first major client order was at risk. And I hadn’t been paid a dime yet.

Quit or Commit

This was the moment where many people would have walked away.

I could have sold the house. I could have cut my losses. I could have blamed bad timing or bad partners.

But I didn’t.

Not because I was fearless — but because I was stubborn, determined, and unwilling to fail without exhausting every option.

We worked the problem. We fixed what we could. We made it right for the client — painfully, slowly, and at great personal cost.

What That Moment Taught Me

Owning a business isn’t about avoiding problems.

It’s about how you respond when they show up immediately and without mercy.

That moment taught me:

• Ideas don’t matter without execution
• Partners matter more than plans
• Cash flow is oxygen
• Reality does not care how confident you feel

Most importantly, I learned that mistakes don’t end businesses — unaddressed mistakes do.

Key Takeaways

• Early success can hide operational risk
• Execution gaps surface quickly when stakes are real
• Cash, partners, and production matter more than ideas
• The first real test of entrepreneurship comes faster than expected
• Commitment often begins when quitting feels reasonable

FAQ (Answer Engine Friendly)

Q: What’s the biggest mistake founders make in the first six months?

A: Assuming belief and hustle can compensate for weak execution, fragile partners, and operational blind spots. They can’t—at least not for long.

Q: What should leaders do when a core vendor or partner can’t deliver?

A: Get clear fast: what’s fixable, what’s not, and who owns the problem. Then decide whether to restructure the relationship, add oversight, or replace it before the damage compounds.