December 13, 2025

A business owner we worked with spent one hour-one!-reviewing all the tech her 12-person team used.

Here’s what she found:
• Three different project management tools
• Two separate file storage systems
• Four places where client info was being manually retyped
• Email threads titled “FINAL FINAL v7 ACTUAL FINAL”
• Enough duplicate work to make you question the meaning of life

Her team was burning 12 hours per week each doing redundant or unnecessary tasks. That’s 7,488 hours a year. At $35/hour, that’s $262,080 evaporating into the tech void.

By January, she’d consolidated tools, automated processes, and cleaned up workflows. Her team got 12 hours a week back. Her bank account stopped bleeding. And yes… she used the savings to book a Hawaii trip.

Let’s help you find your Hawaii fund hiding inside your tech stack.

Money Pit #1: Communication Chaos
Cost: $4,550 - $6,100/month for a 10-person team

Your team is juggling:
• Email
• Slack
• Microsoft Teams
• Texts
• Phone calls
• Smoke signals (probably)

Important info ends up scattered across five different places. People waste 30+ minutes searching for “that one file” someone swears they sent last week.

The real cost: Three to four hours lost per person, every week. At $35/hour, that’s $1,050–$1,400 weekly. Annually? $54,600 - $72,800.

Real story: A marketing agency had project updates split between email, Slack, Google Docs, and their project management tool. Client onboarding lived in three formats. New hires spent their first week just figuring out where information was hiding.

The fix: Choose ONE tool for each type of communication and stick to it:
• Urgent: Phone calls
• Project updates: Project management tool (and nowhere else)
• Quick questions: Slack or Teams - pick one
• Formal communication: Email
• Client updates: CRM

The rule: “If it’s not in the designated system, it doesn’t exist.”

Your Hawaii fund: Even small improvements = ~$2,000/month saved.

Money Pit #2: Disconnected Tools That Don’t Talk to Each Other
Cost: $400 - $1,900/month

Your team enters the same info over and over, in multiple systems, like some kind of corporate Groundhog Day. A lead comes in. Someone copies it to the CRM. Someone else creates a project. Accounting enters it manually. Everyone dies a little inside.

Real example: A real estate agency spent 14 minutes manually entering each new lead into four separate systems. With 60 leads per month, that was 14 hours of copy-paste work. They replaced that workflow with simple automation. Time required per lead afterward: 30 seconds. Annual savings: $5,670. Bonus: Zero typos.
Your Hawaii fund: $5,000 - $20,000/year saved. That’s airfare and your oceanfront room.

Money Pit #3: Paying for Tools You Don’t Use
Cost: $500 - $1,500/month

This one hurts - because it’s true for almost every small business. What you’ll likely find when you check your credit card:
• Old project management tools nobody uses
• Three video meeting subscriptions
• A social scheduling app your intern tried once
• A CRM you haven't opened since 2022
• That “free trial” that’s been charging you $39.99/month ever since

Real example: A consulting firm found they were paying for:
• 2 project management tools
• 3 communication platforms
• 2 storage systems
• A graveyard of forgotten subscriptions
Total annual waste: $8,400.

The fix: Set a timer for 20 minutes. Then:
1. Pull the last 3 months of credit card statements.
2. Write down every recurring software charge.
3. For each one, ask:
o Did we use it in the last 30 days?
o Do we have another tool that does the same thing?
o If we were starting today, would we buy this?
4. Cancel anything that fails all three.

Your Hawaii fund: Most businesses instantly find $500 - $1,500/month in waste. That’s $6,000 - $18,000/year. Translation: Hawaii first-class.

Add It All Up: Your Vacation Money

Let’s be conservative and assume modest savings:
• Communication fixes: $36,400
• Automation: $4,000
• Subscription cleanup: $6,000
Total: $46,400/year

That’s a vacation + bonuses + new equipment + cash left over. These aren’t one-time savings. They repeat every year you keep your systems tight.

Stop Throwing Money Away

The business owner from earlier didn’t do a dramatic overhaul. She spent one hour reviewing her tech stack. She found three big money pits. She fixed them one by one. Now her business runs more smoothly, her team is happier, and her bank account is healthier. And yes - she went to Hawaii.

Your turn. Where do you want to go in 2026?

Ready to find your hidden vacation fund? Dragonfly MSP can help you audit your tech stack and recover the money you’re losing every month.

👉 Book a free discovery call: https://www.dragonflymsp.net

Because your money should be buying piña coladas on the beach - not paying for software you forgot existed.