Startup Oversight, Missed Red Flags, and a $47,000 Wake-Up Call

 

When Your Business Partner Hides the Truth: A Painful Lesson in Financial Awareness

Starting a business with a friend can feel like the perfect setup. You each do what you’re good at. They handle their side, you handle yours, and together you build something big. Sounds ideal, right?

But what if that trust hides a problem? What if the money is slipping away, and you don’t see it coming?

That’s what happened to me. And I still carry that lesson today.

 

It Seemed Like a Perfect Fit—Until It Wasn’t

When Chris and I started Halifax Design Studio, everything just worked. I built the websites. He handled sales and ran the day-to-day. It was simple and smooth.

At first, we were on fire. Projects were flowing. Clients were happy. I was deep in the creative work, and Chris kept the business running.

But after about seven months, things felt… off. Chris wasn’t chasing leads anymore. He spent more time organizing files than closing deals.

We had no new clients lined up. That was a big problem—sales weren’t my thing.

 

A Quick Fix That Made Things Worse

To patch the gap, we hired sales reps on commission. It helped short-term, but their cuts ate into profits. We were spending more just to stay afloat.

And the real problem? We weren’t talking about the money. We weren’t working as a team.

 

Then I Saw the Numbers

Chris took a vacation, so I covered his work. I started digging into our books, just to stay on top of things.

What I found made my stomach drop. We had less than six weeks of cash left. At the pace we were spending, we’d be broke in no time.

 

A Hard Talk I’ll Never Forget

When Chris got back, I showed him everything.

“We need to talk about the money,” I said.

He shrugged. “I’ve got this. I didn’t want to worry you.”

That hit hard. We were both responsible, yet he’d kept me in the dark.

“Yes, it’s your job,” I told him, “but this affects both of us. We should fix this together.”

We agreed to meet weekly. But it didn’t last. First the meetings slowed, then stopped. When I asked why he wasn’t sharing more, he admitted he was overwhelmed—and didn’t know how to fix it.

By then, we had two weeks of money left.

 

I Should’ve Seen It Coming

Looking back, I blame myself too. I trusted him and focused only on my side of the work.

We didn’t have a budget review. No regular money check-ins. No alerts when things went wrong.

By the time I stepped in, we owed $47,000. Most of it was unpaid loans and overdue bills. We had no assets to cover it. And we were out of time.

We tried to raise money but couldn’t raise enough in time.

We had to shut the business down. And since we split the debt, I walked away owing $23,500. It took me four years to pay it off.

 

The Lesson That Changed How I Work

That experience taught me one thing: if you’re in a business, you need to know the numbers. Always.

Even if someone else handles the money, you can’t ignore it. When problems show up early, they’re easier to fix.

Chris wasn’t trying to hurt us. He just froze. But that silence cost us the whole company.

Here’s What I’d Do Differently (And What You Should Too)

1. Review Finances Often
   Check the money every week or two. Don’t wait for quarterly reports. By then, it might be too late.
2. Know Your Numbers
   Can you explain your cash flow? Burn rate? Runway? If not, it’s time to learn.
3. Use Tech to Help
   Set up alerts for low cash or odd spending. Let the software catch issues early.
4. Talk About Money—A Lot
   Money talk shouldn’t be rare. Make it normal. Add it to team meetings.
5. Get Another Set of Eyes
   Even if you’re not in charge of finances, ask questions. Check in now and then. You might spot something big.
6. Act Fast on Red Flags
   If something feels wrong, don’t wait. Take action right away.
7. Always Have a Plan B
   Know what you’ll cut first. Know who to call if you need funds. Hope is not a plan.

What I Took from the Fall of Halifax Design Studio

It hurt. A lot. But I didn’t walk away empty-handed.

I learned that trust without transparency is risky. And silence, even from fear, can sink a business.

You can’t just hope your partner has it all handled. You need to look for yourself.

The Big Takeaway: You Can’t Ignore the Money

One of the worst mistakes in any partnership is thinking trust means you don’t need to check in.

This story proves how fast things fall apart when you split roles too cleanly—and stop talking about money.

Here’s the truth:

Even If You Don’t Manage the Money, You Still Need to Know What’s Going On

Great partners stay involved in everything that matters—even if it’s not their job on paper.

Silence around money is dangerous. It doesn’t excuse anyone from staying aware.

Transparency should happen often, not just when trouble hits.

Trust needs proof. Oversight isn’t a threat—it’s a safety net.

Stay Aware: A Quick Checklist for Financial Health in Any Partnership

☐ Set up regular financial check-ins
☐ Make sure both partners can access all money data
☐ Share key financial tasks to increase visibility
☐ Set alerts for cash flow problems
☐ Talk about money in your normal team rhythm
☐ Document who handles what and how decisions get made

Red Flags to Watch Out For

These signs can show your business is in trouble. Catch them early, and you have options.

1. You Rarely Talk About Money
   If it’s always “not the right time,” that’s a sign something’s hidden.
2. One Person Has All the Control
   No shared oversight? You’ve got blind spots.
3. Cash Feels Tight, But There’s No Clear Reason
   If no one can explain the pinch, it’s time to look deeper.
4. Spending Shifts Without a Word
   If people notice late payments or odd charges, don’t brush it off.
5. Reports Are Late or Missing
   If numbers aren’t shared on time, there’s usually a reason.
6. Sales Slow Down, but Costs Stay Up
   Revenue drops should lead to cuts or planning. If not, there’s a disconnect.
7. “Don’t Worry, I’ve Got It” Gets Said Too Much
   This line works in small doses—but used too often, it’s a warning.

Self-Check: Are You Financially Aware?

Ask yourself:

• Do you meet to review finances at least twice a month?
• Can you explain your company’s money situation in plain terms?
• Do you and your partner both see real-time money data?
• Have you agreed on what red flags require action?
• Are your financial roles clearly written out?
• Do you check invoices and expenses, even if it’s not “your thing”?
• Is it easy and normal to talk about money in your team?

Results:

6–7 Yes Answers: You’re doing great. Keep the habits strong.
4–5 Yes Answers: Good start but tighten things up.
3 or Fewer: You need to act now. You’re at real risk.

Final Thoughts: Stay in the Loop—Always

Losing Halifax Design Studio was rough. But it opened my eyes.

We didn’t fail because we lacked skill. We failed because we didn’t share the burden. We trusted each other—but we didn’t double-check.

If you lead, partner, or manage, stay close to the money. Don’t wait for bad news to get involved.

It’s not about control. It’s about safety, clarity, and giving your business a fighting chance.

You don’t have to be a financial whiz. You just need to care, stay curious, and speak up.

Because in the end, staying aware isn’t optional. It’s how you stay in business.