In this episode, the hosts dive into a high-flying tourism aviation business for sale in the Southeast, featuring helicopters, helipads, and hefty margins—with a healthy side of legal intrigue and risk.
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In this jam-packed episode, Michael, Heather, Bill D'Alessandro, and Mills dissect a tourism helicopter business listed at $8.5M with $1.7M in adjusted EBITDA. Located in the Southeast, this operation includes two entities, strong margins, and a recent legal win securing exclusive access to a grandfathered helipad. The hosts debate safety risks, pilot recruitment, SBA loan eligibility, and who the right buyer might be—ranging from aviation nuts to strategic tourism operators. Tune in for a fun, thoughtful analysis of this high-risk, high-reward deal.

Key Highlights:
- $8.5M asking price for a Southeast-based helicopter tourism business generating $1.7M in EBITDA
- Legal victory secures exclusive helipad access, creating a possible local monopoly
- Deep dive on pilot quality, aviation safety, and maintenance challenges
- Pros and cons of SBA loan structuring for a capital-intensive business
- Hilarious real-life stories of $20 helicopter rides and upsell pressure mid-flight
- Ideal buyer profile: tourism veteran or aviation enthusiast with operational savvy

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In this episode, Michael and Heather dive into a blue-collar print-on-demand business listing with one of the most brutally honest and emotionally raw seller notes we've seen.

Business Listing - https://quietlight.com/listings/16974795/?utm_medium=sms

🎙️ This episode is sponsored by:
Capital Pad – The platform for entrepreneurs buying businesses to connect with investors. List your deal or invest in others at https://www.capitalpad.com

Inzo Technologies – IT services built for small business acquisitions. Get your free IT audit at https://www.inzotechnologies.com

After purchasing a $3.8M revenue business that once made over $1.5M in profit, the current owner watched it crash—financially and personally. From RoAS nightmares to marital stress and burnout, this listing reads like a business soap opera. Is there an opportunity buried in this chaos, or is this a cautionary tale for all would-be acquisition entrepreneurs? Tune in for a breakdown of the financials, emotional stakes, and our hosts’ final thumbs-down verdict.

Key Highlights:

• The business was acquired in 2024 and quickly began to decline.
• Seller cites emotional burnout and personal turmoil as key motivators to sell.
• Revenue was $3.8M with a 2.76x asking price ($1.2M).
• High dependency on Meta (Facebook/Instagram) ads and creative refresh.
• Hosts question the viability of turnaround, debt structure, and potential buyer strategy.
• Suggested creative deal structures for rescuing distressed businesses.
• A discussion on why this listing is a clear example of the difference between good and bad business risk.

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• Do you enjoy our content? Rate our show!
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A fast-growing car hauling and truck repair business in New Jersey raises eyebrows and red flags in this high-revenue listing breakdown.

Business Listing - https://www.bizbuysell.com/Business-Opportunity/automobile-hauling-transportation-company-and-truck-repair-for-sale/2319221/

📣 This week's sponsors:

🚚 Capital Pad — The ultimate marketplace for acquisition entrepreneurs to raise or deploy capital with standardized, professional deal terms. Learn more: https://www.capitalpad.com/

💻 Inzo Technologies — IT expertise for small businesses from a fellow searcher. Get a complimentary IT audit before you buy: https://www.inzotechnologies.com/ or email Nick at nick@inzotechnologies.com

In this episode, the crew dives into a wild listing for a nationwide car hauling and truck repair company based in New Jersey that claims $7.2M in revenue and $1.2M in EBITDA in just four years of operation. With flashy numbers, minimal physical infrastructure, and a broker touting “strategic growth,” the team questions whether there’s any real equity value here—or if this is just a hustle built on a fleet of three-car trailers and thin margins. Personal car-shipping stories, freight brokerage economics, and trucking regulation shakeups all add context to why this deal might be more risk than reward.

🔑 Key Highlights:

• 🚚 $7.2M revenue and $1.2M EBITDA from a car hauling biz founded in 2021
• 🔧 In-house truck repair shop claimed as a competitive advantage
• 📉 Lack of exclusive contracts and questionable inventory valuation
• 🧮 Freight brokerage economics breakdown, including Shiply’s margins
• 💬 Candid takes on why trucking might be the ultimate red ocean industry
• 🕵️‍♂️ Questions around customer acquisition, route stability, and defensibility
• 🧾 Regulatory risks, SBA financing concerns, and the thin line between EBITDA and EBIT

Subscribe to weekly our Newsletter and get curated deals in your inbox

Advertise with us by clicking here

• Do you love Acquanon and want to see our smiling faces? Subscribe to our Youtube channel.
• Do you enjoy our content? Rate our show!
• Follow us on Twitter @acquanon Learnings about small business acquisitions and operations.

For inquiries or suggestions, email us at contact@acquanon.com