Selling Your Trucking Business: What You Need to Know About the Process

9/10/2025

Most trucking and fleet business owners spend their careers focused on customers, drivers, equipment, and keeping everything running smoothly. Few think about selling until the day comes to retire or move on. That is why the process can feel overwhelming.

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This guide gives you an initial overview of what to expect during the sale process. For many owners, selling a business is a once-in-a-lifetime event. It’s natural for the process to feel complicated or overwhelming when your energy has always gone into running the company, not preparing to exit it. And remember, selling is about more than the number on paper. The details and your legacy matter.

Table of Contents

Understanding the Timeline

Due Diligence and Information Requests

Types of Buyers

Do you Hire Someone to Help with the Sale Process?

What to Ask Buyers

Maximizing Cash at Close vs. Staying Involved

‍The Tradeoffs Beyond Just the Dollar Amount‍

Preparing Yourself and the Business

Final Thoughts

About the author

Nick Lee is a former U.S. Army tank officer and current Entrepreneur-in-Residence at NextGen Growth Partners. He spent eight years leading soldiers, maintaining heavy vehicle fleets, and managing operational logistics before transitioning into the business world.

Nick is focused on acquiring and operating a mission-critical B2B services business, with a long-term commitment to preserving the legacy of its owner and investing in its people.

He graduated from the United States Military Academy at West Point with a B.S. in Information Technology, from Eastern University with an M.S. in Data Science, and from Northwestern University’s Kellogg School of Management with an MBA. Nick lives in Chicago.

Understanding the Timeline

From the first conversation with a buyer to closing, a sale usually takes six to nine months. Some move faster, others slower, depending on how prepared you are, how complex your business is, and how committed the buyer is.

Exploration and Initial Conversations (1–2 months) - Buyers want to know why you are selling and what makes your business valuable. Owners often underestimate truly getting to understand the buyers and their motivations, but it sets the tone.
Letter of Intent (LOI) (2–4 weeks) – Once you find a fit, you negotiate and sign an LOI. It outlines the main terms like price, structure, and timing. While non-binding, it usually includes exclusivity, pausing talks with other buyers.
Due Diligence (2–4 months) – The buyer examines financials, customer contracts, fleet records, compliance history, accident records, and more. This often includes reviewing your DOT authority, FMCSA safety ratings, driver qualification files (DQFs), drug and alcohol testing program, Hours of Service (HOS) logs and Electronic Logging Devices (ELDs), IFTA filings, IRP registrations, and other compliance documents. Delays often come from locating old paper records or third parties confirming liens, registrations, or transfers. The more organized you are, the faster this stage moves.
Purchase Agreement and Closing (1–2 months) – The lawyers give their final blessing and everyone signs the paperwork. Once signed, prepare for the largest wire transfer of your life. Time to celebrate!

Even after closing, most deals include a 3–12 month transition where you may help the new owner learn the ropes, meet customers, or guide the team.

Due Diligence and Information Requests

Due diligence is often the part that surprises owners most. Buyers will ask for a lot, and it can feel endless and invasive at times. Another reason why having a strong relationship with the buyer upfront is so important.

Typical requests include:

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Financials – Years of tax returns, profit and loss statements, balance sheets, and cash flows.
Customer data – Contracts and rate sheets, customer lists, revenue by account and by lane, revenue concentration details, load history, broker agreements, and payment terms. The key takeaway is that buyers want to understand which shippers, brokers, or routes drive profitability and how stable those relationships are.
Fleet Equipment – In short, buyers want to understand your fleet inventory. This includes truck and trailer inventory with year, make, model, mileage, VIN, and current value. Maintenance logs, repair history, upcoming preventative maintenance, inspection reports, and capital expenditure plans for replacements and upgrades. Can you break out your maintenance vs. growth capital expenditures? Records of DOT inspections, emissions compliance, and warranties are also fair game.‍
Operations – Dispatching process, route assignments, telematics, safety data, ELD and HOS compliance records, fuel management programs, IFTA filings, and audit history. Buyers will also look at insurance claims and accident records to assess risk.
People – Driver rosters with license type (CDL A/B/C), years of experience, violation history, training records, turnover rates, and compensation structure. Information on benefits, retention programs, and key managers is of great importance to show stability of your workforce.

Buyers also need to know how much of the business is tied to you personally. Do you as the owner hold licenses or permits in your name? If so, can key managers easily get these credentials? Do key customers revolve around your involvement? If so, how will you help maintain these major accounts when new leaders take over?

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Preparing means putting contracts in the company’s name and introducing your leadership team to key customers and suppliers before the sale. The goal is simple: buyers want confidence that the business can run smoothly without you at the center.

Types of Buyers

Not all buyers are the same. They tend to value different areas and will treat your business accordingly. Make sure you go into the sale process with eyes wide open.

Strategic buyers – These are other companies in trucking, logistics, or adjacent services that want to expand. For example, a regional LTL carrier might want your long-haul routes to extend its footprint, or a specialized reefer carrier may want your dry van fleet to diversify. Logistics firms, freight brokers, or 3PLs may see value in your customer base or fleet capacity. Strategics often “bolt on” your company to a larger platform, which can mean your brand and systems get absorbed. The upside is that they sometimes pay a premium for assets that fit their network. The tradeoff is giving up control of your company’s name, culture, and legacy.
Financial buyers – These include private equity firms, family investment offices, and larger funds. Many have active transportation portfolios and look for add-on acquisitions to scale existing platforms. For example, a private equity group that owns a flatbed carrier might acquire a dry van or tanker fleet to cross-sell services and consolidate back-office functions. Their goal is to scale with more customers, more lanes, and more revenue. They often pay well but expect you or your team to stay on and run the business. Most target a growth period of five to seven years before reselling the business. The tradeoff is they may push harder on short-term performance metrics like utilization, cost-per-mile, and EBITDA margins, adding strict reporting requirements and stress on your employees.
Individual or entrepreneurial buyers – This is the category I fall into. These are entrepreneurs backed by investors, often through an Entrepreneurship Through Acquisition (ETA) model. Many are former executives, veterans, or MBAs who raise capital from a group of investors and advisors to acquire and run a single business. Sometimes they are known as search fund entrepreneurs or Entrepreneurs-in-Residence (EIRs) at investment firms. Unlike private equity or large strategics, they typically step in as a full-time CEO, with a long-term commitment to preserving the company’s culture, reputation, and people. The tradeoff is they may need a longer transition period while learning the business, relying on a strong relationship with the seller and management team to guide them in the early months.

Each type brings upsides and downsides: strategics may pay more but change your business’s identity, financials bring capital but can put undue pressure on your employees and company, and entrepreneurial buyers protect culture but need your involvement early on.

Do you Hire Someone to Help with the Sale Process?

A key decision is whether to hire an intermediary such as an investment bank or broker to represent you in the sale process. Note, hiring your own tax and legal advisor is separate and highly encouraged.

The benefit is these intermediaries “run a process” which includes preparing a confidential information memorandum (CIM, essentially a nice marketing deck of your company with high level information), market the company widely, manage requests from interested buyers, and negotiate. Competition can drive up the price, and they handle the heavy lifting so you can focus on running the business.

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The tradeoff is cost. Similar to using a realtor when you sell your home, you pay their fees. This could range from 5–10 percent of the transaction value for smaller businesses, with lower percentages as deal size increases. On a multi-million-dollar sale, that adds up. It can also feel less personal, with deadlines and presentations instead of direct conversations.

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The other option is selling through your trusted network. Maybe a CPA, advisor, or family friend knows a potential buyer. You work directly with them, bringing in lawyers and accountants to guide the process. This often keeps more money in your pocket and can make the transition smoother. The downside is less competition, which might mean a lower price.

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Neither approach is right or wrong. Running a process maximizes reach. Working through your network prioritizes fit and simplicity.

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What to Ask Buyers

When evaluating offers, money matters, but questions reveal more than numbers

Why do you want to buy this business?
How will you treat employees and customers?
What experience do you have leading through change?
What does your growth timeline look like?
How long do you expect me to stay involved?

The answers show whether a buyer’s motivations align with your goals.

Maximizing Cash at Close vs. Staying Involved

A major decision is how much you get upfront versus what is tied to the future.

Cash at close – You sell and step away. Most of the money is paid immediately.
Seller financing and earn-outs – Some are paid over time, often tied to the company’s continued performance. This lowers risk for the buyer but keeps you tied to results.
Transition roles – Many owners stay for three months to two years, helping with customers or operations while stepping back gradually.

The Tradeoffs Beyond Just the Dollar Amount

It is easy to overly focus on the dollar amount, but structure matters just as much.

If you want to walk away immediately, buyers may see it as a lack of confidence in the business. To de-risk, they might ask for equity rollover or an earn-out where you only receive full value if the business performs after the sale.

If you are open to staying involved, you often have more negotiating room. Some owners stay on as CEO under financial or strategic buyers. Others shift into roles they enjoy most, such as sales or customer relations. The key is being honest about what you want after closing. Looking only at the dollar figure can leave you tied to the business longer than you planned.

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Preparing Yourself and the Business

If you plan to sell in the next few years, a little preparation now makes a big difference:
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Solidify your priorities and identify your own trade-offs.
Build a strong second layer of leadership.
Reduce overreliance on one or two customers.
Clean up financial records and start digitizing key paperwork.
Update fleet maintenance logs and identify necessary permits and credentials.
Map out job duties and processes to identify bottlenecks.

These steps reassure buyers and improve your odds of better offers.

Final Thoughts

Selling your trucking business is a big decision, and for most owners, you only sell a business once. The process is not just about the purchase price. It is about who takes the wheel next, how employees and customers are treated, and how your legacy carries forward.

By understanding the process, preparing early, and asking the right questions, you can find a buyer who values what you built and will keep it running in a way that not only makes you proud but also gives you a valued voice in the decision making.

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Selling Your Trucking Business: What You Need to Know About the Process

Understanding the Timeline

Due Diligence and Information Requests

Types of Buyers

Do you Hire Someone to Help with the Sale Process?

What to Ask Buyers

Maximizing Cash at Close vs. Staying Involved

The Tradeoffs Beyond Just the Dollar Amount

Preparing Yourself and the Business

Final Thoughts

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