The lost Trucking Company

Ever had a deal haunt you because you hesitated? Tell you about the $3.5M trucking company I missed out on—and the lessons it taught me.

I was recently looking at a trucking company that provides same-day courier services in Southern California.

The deal first came to market 8 months ago, and I passed on it. But something about it stayed with me. I revisited it a month ago, but by the time I got back, it was too late—it was already under contract.

Here’s the breakdown of the deal:

The Numbers

• Established: 1988(checks more that 8 years of being established)

• Listing Price: $3,500,000

• Services: Same-day courier, refrigerated transport, legal courier, medical delivery, cargo logistics.

• Team: 25+ employees, 10–15 contractors

• Fleet: 8 company-owned vehicles (16-foot refrigerated box truck + cargo vans).

• Revenue (2023): $3,076,858

• Cash Flow (SDE): $801,566

• EBITDA: $701,566

• Margins: Consistent profitability with discretionary earnings exceeding 25%.

Where I Hesitated

When I first saw this deal, I thought, “I know trucking, but do I understand the nuances of same-day delivery?” So, I did what I should’ve done earlier: called industry experts.

Here’s what they told me to look out for:

1. Customer Mix & Pricing Power:

• Are margins this high because of pricing power or poor cost representation?

2. Depreciation Mystery:

• No depreciation listed? That means the fleet might be old or they didn’t account for it properly.

3. Add-Backs:

• Every deal has them, but not all will pass the lender’s scrutiny.

4. Real Estate Situation:

• Does the business own or lease its location? Do pickup/delivery logistics depend on it in the long term?

5. Third-Party Driver Contracts:

• Are there set rates for pickups/deliveries, or is pricing negotiated per transaction?

6. Revenue Breakdown:

• What’s the split between on-demand, courier, and scheduled services? How much revenue is recurring?

-What is the cost per delivery

-How optimized are the routes?

7. Fleet & Expansion Readiness:

• Are capital investments needed soon? Can the fleet/staff support growth?

What I Offered

Based on my analysis and due diligence, I structured the following offer:

• Purchase Price: $2,000,000

• Structure:

• $1,800,000 upfront at closing (90%)

• $200,000 seller note (10%) at 6% interest, payable over 10 years with the first 2 years on full standby (no payments).

The offer was rejected—the business was already under contract.

The Lessons I Learned

1. Don’t Wait:

• If you’re interested, submit an offer early. Dig deeper after you’ve locked in exclusivity.

2. Ask Experts:

• Industry experts can quickly uncover risks and opportunities you might miss.

3. Be Ready to Walk Away:

• Even with a great deal, if the numbers don’t work, stick to your offer.

I missed this deal, but the experience sharpened my diligence process and taught me invaluable lessons.

Have you ever let a deal slip through your fingers? What did you learn from it? Drop your lessons in the comments! or Just Give some Advice!