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- ⛵ Key West Charter Business making $400k/yr!
⛵ Key West Charter Business making $400k/yr!
The Corporate Pivot
February 24, 2025
Welcome Back to The Corporate Pivot!
If you’ve ever found yourself deep in a Google search for “jobs that pay the most” or “jobs that don’t suck,” I’ve got some news for you—you might not need another job. You might need another way out.
There’s a path that’s more fulfilling and (spoiler) can make a lot more money. One where you’re not stuck making last-minute PowerPoint changes because your boss suddenly decided the font is too small.
This is The Corporate Pivot—where we break down what it actually takes to start or buy a business and escape the 9-to-5 grind before you’re 65. It’s not easy, but it sure beats another “quick sync” that somehow lasts an hour.
Here’s what we have for you today:
Pivot Perspectives: Sam talks about crafting cold call scripts to turn bookkeeping leads into real opportunities. Tyler talks about the joys of tax prep, cleaning up bookkeeping, and finding new ways to acquire home service routes. | Acquisition Alerts:
| Mindset Matters: Vinny talks about the horrors of Monday mornings, questionable management decisions, and the art of surviving 8 AM meetings (barely). |
Cool Business Idea:
Companies are required to provide OSHA safety training—but they don’t always have in-house trainers. 🚧
By hiring your own team of certified trainers, you can land corporate contracts and scale to $200K+ per year without doing all the training yourself.
Read below to learn more! ⬇️
If you haven’t already, go subscribe to this newsletter here!
Confusing Corporate Sayings:
Confusing Corporate Saying:
"Living the dream!"
Professional Translation:
“They’re expressing enthusiasm about their job and life.”
Corporate Pivot Translation:
“I hate this place, I’m dying inside, and this is my only socially acceptable way to say it.”
Sam’s Perspective (1st Time Buyer)
🆕 Status Update: We scraped 39 bookkeeping businesses using the Google Places API and pulled public owner info—now it’s time to start calling. To maximize success, our script follows a proven structure:
Pattern Interrupt (Grab Attention in 5 Seconds or Less)
Why? Business owners get sales calls constantly. A strong opener prevents immediate brush-offs.Clarity & Purpose (No Fluff, Get to the Point)
Why? Busy people won’t stay on the call if they don’t immediately know why you’re calling.Quick Value Proposition (What’s in It for Them?)
Why? People only stay engaged if they see an immediate benefit.Soft Engagement Question (Encourage a Conversation, Not a Pitch)
Why? If they respond, they’re more likely to stay on the call.Handling Objections (Preempt Common Pushbacks)
Why? The first “I’m not interested” is often a reflex, not a real objection.Clear Next Step (Always Book a Call or Send Info Immediately)
Why? Leaving things open-ended kills deals. If they show interest, lock in a next step.
This script keeps the conversation direct, engaging, and value-driven while minimizing resistance. Now, time to start dialing.
Tyler’s Perspective (Experienced Buyer)
🆕 Status Update: In keeping with my own advice, we’ve been working on finalizing our bookkeeping to get ready for tax season. We use a CRM and bookkeeping software, but unfortunately, some line items don’t import correctly, requiring manual corrections to categorize expenses properly. It’s a tedious process, but it ensures accuracy and keeps our monthly financial reporting on track.
Alongside tax prep, we’re still focused on acquiring more routes. While traditional marketing works, we’re also exploring new ways to find routes through the right online platforms.
It’s going to be a busy few months for everyone handling taxes—don’t wait until the last minute!
💰 Deals < $500k 💰
Business Name: Carpet & Rug Cleaning Business
Revenue: $485,529
Asking Price: $499,000
Profit: $200,437 (Profit Margin = 41.3%)
Location: Sarasota County, FL
Established: 1954
✅ Pros:
Established Reputation: With 70+ years in business, the company has a strong brand, loyal customers, and trust within the community.
Turnkey Operation with Minimal Owner Involvement: The owner works only ~25 hours per week, primarily in management and sales, making this an easy transition.
⚠️ Con:
Local Market Dependence: The business primarily serves Sarasota and Manatee Counties, which may limit growth potential unless expansion strategies are implemented.
📈 Growth Opportunities:
Expand into High-End Residential & Commercial Contracts: Offering specialized cleaning for luxury homes, hotels, and commercial spaces could increase revenue.
Develop a Digital Marketing & Subscription Model: Implementing SEO strategies, Google Ads, and subscription-based cleaning plans could attract new customers.
💰💰 Deals $500k - $2m 💰💰
Business Name: Key West Charter Business
Revenue: $1,500,000
Asking Price: $1,000,000
Profit: $400,000 (Profit Margin = 26.7%)
Location: Key West, FL
Established: 2015
✅ Pros:
Strong Tourism Market & Repeat Business: Key West is a year-round tourist destination, ensuring a steady stream of customers for private charters and luxury boat tours.
High-Value Fleet Included: The sale includes 4 well-maintained boats, including a 45' Corinthian Power Catamaran with a liquor license, allowing for upscale, high-margin tours.
⚠️ Con:
Weather-Dependent Business: Revenue may fluctuate due to hurricanes, tropical storms, or seasonal slowdowns, requiring contingency planning.
📈 Growth Opportunities:
Expand VIP & Luxury Offerings: High-end experiences such as premium catering, private chefs, and luxury yacht charters could attract a wealthier clientele.
Leverage Digital Marketing & Social Media: Enhancing online presence with targeted ads, influencer partnerships, and travel agency collaborations could boost bookings.
💰💰💰 Deals $2m-$10m 💰💰💰
Business Name: Pavement Maintenance Company
Revenue: $2,168,816
Asking Price: $3,149,000
Profit: $982,747 (Profit Margin = 45.3%)
Location: Broward County, FL (Relocatable)
Established: 2004
✅ Pros:
Diverse Revenue Streams: Services include asphalt repairs, striping, seal coating, sidewalks, and parking lot maintenance, ensuring steady demand.
Scalable & Growth-Oriented: The company has expanded from a pressure-washing service into full-scale pavement resurfacing, demonstrating adaptability and market expansion potential.
⚠️ Con:
Equipment-Heavy Business: Requires significant investment in machinery and ongoing maintenance, impacting cash flow.
📈 Growth Opportunities:
Expand into Government & Large Commercial Contracts: Targeting municipal and HOA contracts could lead to higher long-term revenue.
Invest in Specialized Services: Adding niche offerings like thermoplastic road striping, pervious pavement solutions, or eco-friendly coatings could attract premium clients.
The Sunday Scaries👻
Monday the 24th is kinda like Friday the 13th. The Sunday Scaries are hitting harder than that 9th shot of tequila on Thirsty Thursday. Does anyone else miss the college Saturday morning hungover brunches? Instead, now we get 8am meetings on Monday mornings so that we can talk our "strategies"... does anyone else know what the hell that means!
8am onsite meetings Monday through Friday was great when I didn't work. But now that I do I question my management's sanity. Who thinks it's a good idea to get ME up from my slumber, at least when its remote I can turn off my camera and blame it on the lack of my "bandwidth". They think I'm talking about WIFI but I mean my brain power.
Question Time: What happens when you wake up hungover for your Monday morning meeting? Do you:
Draw eyes on your eyelids so you can sleep during the meeting?
Take your 5th sick day this month?
Attend but sit on your computer watching videos of how-to day trade?
If you have done all 3 and it's only the 3rd Monday of the month, welcome to the club! Thats why we subscribe to the Corporate Pivot!
Note: This portion of the writeup is intended to be satirical. No one should ever listen or follow this type of behavior. We are frankly surprised that anyone even reads these things.
Read more at corppivot.com!
💡 Cool Business Idea: OSHA Instructor Certification & Training Business 🚧
Instead of just training workers, why not train the trainers? OSHA safety training is a huge industry, and you can scale beyond just corporate contracts by helping others become certified instructors—all while making recurring revenue from your own training programs.
⬇️ Let’s break down the numbers!
🛠️ Startup Costs (One-Time Investment)
Item | Estimated Cost |
|---|---|
OSHA Outreach Trainer Certification | $695 – $1,500 |
Advanced Instructor Certification (Optional) | $1,500 – $3,000 |
Course Materials (Manuals, Workbooks) | $500 – $1,000 |
Website & Booking System | $2,000 – $4,000 |
Insurance & Business Licensing | $1,000 – $2,000 |
Marketing (Ads, Networking, Outreach) | $2,000 – $5,000 |
Total Startup Costs | $7,500 – $16,500 |
💡 The key difference here is that you’re also selling instructor certifications!
💰 Revenue & Profit Breakdown
🔹 Pricing:
$150–$250 per worker for OSHA 10-Hour Training.
$300–$500 per worker for OSHA 30-Hour Training.
$3,000–$10,000 for bulk corporate training contracts.
$2,500–$5,000 per person for OSHA Instructor Certification.
🔢 Customers & Earnings:
Scenario | Workers Trained/Month | New Instructors/Month | Monthly Revenue | Monthly Profit (after $5K expenses) |
|---|---|---|---|---|
Bad (Slow Start) | 10 | 1 | $5,500 | $500 |
Good (Steady Growth) | 30 | 2 | $15,500 | $10,500 |
Great (Corporate + Instructor Training) | 75 | 5 | $45,000 | $40,000 |
💡 At just 2 instructor certifications per month, you’re adding an extra $5K–$10K in revenue.
🚀 Business Plan & Scaling Strategy
1️⃣ Become an OSHA Outreach Trainer – This allows you to train workers, but you need additional certification to train instructors.
2️⃣ Offer OSHA 10 & 30-Hour Training for Workers – Build a base income stream with corporate contracts and individual training.
3️⃣ Launch an Instructor Certification Program – Sell "Train the Trainer" programs for people who want to start their own OSHA training business.
4️⃣ Sell Instructor Packages – Offer bundles with teaching materials, templates, and marketing help for new trainers.
5️⃣ Build an Instructor Network – Partner with certified instructors and take a % from the workers they train under your brand.
6️⃣ Expand to Online Training – Offer self-paced instructor certification & worker training to scale beyond your local area.
🔑 Why This Works
✅ Businesses Pay for Worker Training – OSHA compliance isn’t optional.
✅ Instructors Need Training Too – You create more OSHA trainers, which expands your business.
✅ Recurring Revenue Potential – Workers must re-certify every few years.
✅ Scalable Model – Start local, expand nationwide with online instructor training.
💰 ROI & Payback Period
At just 10 workers/month, you’ll break even in ~3 months.
At 2 instructor certifications/month, you’re making $10K+/month.
At full scale, this is a $500K+/year business.
This model allows you to train workers, train trainers, and collect revenue on both sides. It’s a business that scales beyond your time.
Corporate Memes: Click below to play the video on our Instagram account! |
Hope you enjoy this week's insights and happy deal hunting! Remember, if you find these updates helpful, share this newsletter with a friend!
🛠 USEFUL TOOLS 🛠
If you made it this far then your attention span is better than most. If you want some useful tools, tips, and tricks you can find them all on the website here!
