GENERATIONAL TRANSITIONS FOR TRUCKING BUSINESS OWNERS

Financial & Tax Planning and the Unprecedented Role of Technology | A Practical Guide

GENERATIONAL TRANSITIONS FOR TRUCKING BUSINESS OWNERS

Financial & Tax Planning and the Unprecedented Role of Technology | A Practical Guide

GENERATIONAL TRANSITIONS FOR TRUCKING BUSINESS OWNERS

Financial & Tax Planning and the Unprecedented Role of Technology | A Practical Guide

GENERATIONAL TRANSITIONS FOR TRUCKING BUSINESS OWNERS

Financial & Tax Planning and the Unprecedented Role of Technology | A Practical Guide

This paper offers high-level guiding thoughts to family-owned trucking and logistics carriers assessing strategies to protect their wealth and legacy. It provides an overview of various options for an owner in the course of a generational transition, including selling the business to a third party, selling to key employees, or handing the business to the next generation through gifting or sales processes. It emphasizes the importance of incorporating technology to ensure the sustainability of cash flows, the preservation of wealth, and leveraging technology to address challenges that traditionally surface during generational transitions.

The paper then delves into the critical exercise of estimating the value of a trucking business during succession planning. While technicalities are best left to experts, owners need to understand the rationale and drivers behind value to prepare their company for a sale or handover. Company appraisers use a variety of valuation techniques to arrive at the fair market value (FMV) of a company, which is the price a willing buyer would pay to a willing seller for a trucking company, with both parties having reasonable knowledge of the relevant facts.

In preparing a company for sale, owners should assess and improve the income prospects and risk profile of the company to achieve maximum value. Most investors determine the value of the business by assessing the carrier’s operating income generated during the ordinary course of the business, typically free cash flow or EBITDA as a proxy. Risk factors, such as hidden liabilities or the sustainability of income projections, may result in an investor applying a higher risk premium to a business, resulting in a lower purchasing price. Therefore, trucking company owners should demonstrate the ability to sustain or grow the current level of income even after the departure of the previous owner.

Technology, in particular, smart workflow technology has become one of the most powerful levers for owners in a generational transition. It digitizes the business end-to-end, builds operating standards, institutionalizes the wisdom of the retiring generation, and offers visibility to senior ownership in their task of governing the incoming management. It also increases the confidence that the business remains competitive and that cash flows projected in a valuation are truthfully sustainable. Given the extent of technological change, owners should consider moving off traditional legacy systems that may provide the comfort of habit, but are no longer in tune with the rapidly changing technological context.

This paper offers high-level guiding thoughts to family-owned trucking and logistics carriers assessing strategies to protect their wealth and legacy. It provides an overview of various options for an owner in the course of a generational transition, including selling the business to a third party, selling to key employees, or handing the business to the next generation through gifting or sales processes. It emphasizes the importance of incorporating technology to ensure the sustainability of cash flows, the preservation of wealth, and leveraging technology to address challenges that traditionally surface during generational transitions.

The paper then delves into the critical exercise of estimating the value of a trucking business during succession planning. While technicalities are best left to experts, owners need to understand the rationale and drivers behind value to prepare their company for a sale or handover. Company appraisers use a variety of valuation techniques to arrive at the fair market value (FMV) of a company, which is the price a willing buyer would pay to a willing seller for a trucking company, with both parties having reasonable knowledge of the relevant facts.

In preparing a company for sale, owners should assess and improve the income prospects and risk profile of the company to achieve maximum value. Most investors determine the value of the business by assessing the carrier’s operating income generated during the ordinary course of the business, typically free cash flow or EBITDA as a proxy. Risk factors, such as hidden liabilities or the sustainability of income projections, may result in an investor applying a higher risk premium to a business, resulting in a lower purchasing price. Therefore, trucking company owners should demonstrate the ability to sustain or grow the current level of income even after the departure of the previous owner.

Technology, in particular, smart workflow technology has become one of the most powerful levers for owners in a generational transition. It digitizes the business end-to-end, builds operating standards, institutionalizes the wisdom of the retiring generation, and offers visibility to senior ownership in their task of governing the incoming management. It also increases the confidence that the business remains competitive and that cash flows projected in a valuation are truthfully sustainable. Given the extent of technological change, owners should consider moving off traditional legacy systems that may provide the comfort of habit, but are no longer in tune with the rapidly changing technological context.

1. INTRODUCTION

The 1980 Motor Carrier Act signed into law by President Nixon marked the beginning of the deregulation of the interstate transportation industry. Before 1980, the Interstate Commerce Commission had granted only 18,000 truckers operating licenses with only a handful allowed to work across state lines. By 1990, the number of licensed motor carriers had reached 45,000 of which 20,000 move goods freely across the 48 contiguous states (Moore, 1995).

Deregulation brought significant entrepreneurial opportunities for trucking companies founded in the 1980s and 1990s. As a result, today - thirty to forty years later - trucking companies founded during this era have become sizable, family-owned businesses. Their founders, many of which are still actively involved in the day-to-day operations, are assessing their transition alternative, balancing their personal financial needs, and protecting their legacy.

The purpose of this paper is to offer ownership at family-owned carriers high-level guiding thoughts to assess strategies to protect the wealth and legacy created in their trucking and logistics businesses. We will cover those strategies under various options an owner may contemplate in the course of a generational transition, including (a) a straight sale of the business to a third party (b) sale to key employees, or (c) handing the business to the next generation as part of succession planning using either a gifting or a sales process.

Today, in an era where new trucking companies get created as “digital native” businesses and disruptive business models can shake up the profitability of long-established incumbents, it is more important than ever to incorporate aspects of technology: both to ensure the sustainability of cash flows and the preservation of wealth, but also to leverage technology to address challenges that traditionally surface during generational transitions. In other words, technology is taking an unprecedented role in protecting and creating trucking companies’ enterprise value.

This is why two leading providers in the areas of technology, accounting, tax and estate planning have teamed up to produce this guide[1] [2] . Aside from the basic frameworks we are providing, we acknowledge the limitations of their generic nature and encourage you to reach out directly to us for more specific conversations.

1. INTRODUCTION

The 1980 Motor Carrier Act signed into law by President Nixon marked the beginning of the deregulation of the interstate transportation industry. Before 1980, the Interstate Commerce Commission had granted only 18,000 truckers operating licenses with only a handful allowed to work across state lines. By 1990, the number of licensed motor carriers had reached 45,000 of which 20,000 move goods freely across the 48 contiguous states (Moore, 1995).

Deregulation brought significant entrepreneurial opportunities for trucking companies founded in the 1980s and 1990s. As a result, today - thirty to forty years later - trucking companies founded during this era have become sizable, family-owned businesses. Their founders, many of which are still actively involved in the day-to-day operations, are assessing their transition alternative, balancing their personal financial needs, and protecting their legacy.

The purpose of this paper is to offer ownership at family-owned carriers high-level guiding thoughts to assess strategies to protect the wealth and legacy created in their trucking and logistics businesses. We will cover those strategies under various options an owner may contemplate in the course of a generational transition, including (a) a straight sale of the business to a third party (b) sale to key employees, or (c) handing the business to the next generation as part of succession planning using either a gifting or a sales process.

Today, in an era where new trucking companies get created as “digital native” businesses and disruptive business models can shake up the profitability of long-established incumbents, it is more important than ever to incorporate aspects of technology: both to ensure the sustainability of cash flows and the preservation of wealth, but also to leverage technology to address challenges that traditionally surface during generational transitions. In other words, technology is taking an unprecedented role in protecting and creating trucking companies’ enterprise value.

This is why two leading providers in the areas of technology, accounting, tax and estate planning have teamed up to produce this guide[1] [2] . Aside from the basic frameworks we are providing, we acknowledge the limitations of their generic nature and encourage you to reach out directly to us for more specific conversations.

2. HOW MUCH IS YOUR BUSINESS WORTH

Estimating the value of your business is a critical and sobering exercise during succession planning. The technicalities of a company valuation are best left to experts, but understanding the rationale and drivers behind value is critical for owners of trucking companies to prepare their company for a sale or a hand-over.

Company appraisers have in their quiver a variety of valuation techniques to arrive at what your company’s worth (see box 1) or what’s commonly referred to as its fair market value (FMV). FMV is the price a willing buyer would pay to a willing seller for a trucking company, with both parties having reasonable knowledge of the relevant facts. In other words, it is the price that would be agreed upon in an open and competitive market, where both the buyer and seller have equal bargaining power and are free from pressure to act.

To understand this price point, it is indispensable for sellers to not solely articulate their own expectations, but also understand how buyers shop for trucking companies. Buyers, whether institutional or not, take into account whether the purchase is “worth the money”. Buyers typically derive the purchase price by evaluating the income potential of the trucking company and applying their target return rate to such income level. For illustrative purposes, if a carrier, generates $1M in net income and the buyer targets at least a 10% return, the price the investor is willing to pay is at most $1M/10%, i.e. 10 times its net income or $10M. Buyers may upward or downward adjust their target return rate based on their perception of risk to be compensated appropriately for taking on more or less risk.

As a seller, carriers need to understand that there’s little they can do about a buyer’s target return expectations, but there’s a lot to enhance a buyers’ perception of income potential and risk. Therefore, in preparing a company for sale, owners should assess and improve the income prospects and risk profile of the company to achieve maximize value. Let’s further break this down.

Income

In most market environments, the potential lies in the value of the business to generate future income as a going concern in perpetuity. A typical approach for investors to determine the value of the business would be to assess the carrier’s operating income generated during the ordinary course of the business, i.e. providing transportation or logistics services. Most investors prefer reviewing income in the form of cash flow (typically free cash flow or EBITDA as a proxy) rather than accounting profits which are more sensitive to accounting assumptions. More recently, we have seen a few unusual cases where, as a result of spiking equipment prices during the pandemic, the value of the company’s tangible asset was higher than the going concern value. In those instances, trucking companies traded as “fleets of equipment” rather than the “value of the business” using operating income approach.

Risk

A variety of risk factors may result in an investor applying a higher risk premium to your business, i.e. demand a higher return which ultimately lowers the purchasing price the buyer is willing to offer. Such risk issues can be embedded in hidden liabilities (e.g. unresolved lawsuits, shipper or other third party claims) or the sustainability of income projections. To optimize for better pricing in a sale, it is important that trucking company owners, especially those where the business is anchored around one individual, demonstrate the ability to sustain or grow the current level of income even after the departure of the previous owner.

BOX 1: KEY VALUATION METHODOLOGIES

Appraisers can estimate the value of your trucking company using multiple techniques.

Discounted cash flow analysis: This technique involves forecasting the future cash flows of your trucking company over say 5 to 10 years, and discounting them back to the present using an appropriate discount rate.

Asset-based valuation: This technique involves valuing the trucking company based on the value of its assets, including both tangible assets (such as property and equipment) and intangible assets (such as patents, trademarks, customer relationships, or data).

Earnings multiple analysis: This technique involves determining the value of the trucking company based on revenue and/or profit and a multiple of such revenue/profit to arrive at a valuation. Reference points for multiples are typically public trucking companies’ PE or TEV/Rev ratios and the sale of private trucking companies, that get adjusted based on the subject carriers’ idiosyncrasies.

It's important to note that no single valuation technique is perfect, and it's often necessary to use a combination of techniques to arrive at a reliable estimate of value.

2. HOW MUCH IS YOUR BUSINESS WORTH

Estimating the value of your business is a critical and sobering exercise during succession planning. The technicalities of a company valuation are best left to experts, but understanding the rationale and drivers behind value is critical for owners of trucking companies to prepare their company for a sale or a hand-over.

Company appraisers have in their quiver a variety of valuation techniques to arrive at what your company’s worth (see box 1) or what’s commonly referred to as its fair market value (FMV). FMV is the price a willing buyer would pay to a willing seller for a trucking company, with both parties having reasonable knowledge of the relevant facts. In other words, it is the price that would be agreed upon in an open and competitive market, where both the buyer and seller have equal bargaining power and are free from pressure to act.

To understand this price point, it is indispensable for sellers to not solely articulate their own expectations, but also understand how buyers shop for trucking companies. Buyers, whether institutional or not, take into account whether the purchase is “worth the money”. Buyers typically derive the purchase price by evaluating the income potential of the trucking company and applying their target return rate to such income level. For illustrative purposes, if a carrier, generates $1M in net income and the buyer targets at least a 10% return, the price the investor is willing to pay is at most $1M/10%, i.e. 10 times its net income or $10M. Buyers may upward or downward adjust their target return rate based on their perception of risk to be compensated appropriately for taking on more or less risk.

As a seller, carriers need to understand that there’s little they can do about a buyer’s target return expectations, but there’s a lot to enhance a buyers’ perception of income potential and risk. Therefore, in preparing a company for sale, owners should assess and improve the income prospects and risk profile of the company to achieve maximize value. Let’s further break this down.

Income

In most market environments, the potential lies in the value of the business to generate future income as a going concern in perpetuity. A typical approach for investors to determine the value of the business would be to assess the carrier’s operating income generated during the ordinary course of the business, i.e. providing transportation or logistics services. Most investors prefer reviewing income in the form of cash flow (typically free cash flow or EBITDA as a proxy) rather than accounting profits which are more sensitive to accounting assumptions. More recently, we have seen a few unusual cases where, as a result of spiking equipment prices during the pandemic, the value of the company’s tangible asset was higher than the going concern value. In those instances, trucking companies traded as “fleets of equipment” rather than the “value of the business” using operating income approach.

Risk

A variety of risk factors may result in an investor applying a higher risk premium to your business, i.e. demand a higher return which ultimately lowers the purchasing price the buyer is willing to offer. Such risk issues can be embedded in hidden liabilities (e.g. unresolved lawsuits, shipper or other third party claims) or the sustainability of income projections. To optimize for better pricing in a sale, it is important that trucking company owners, especially those where the business is anchored around one individual, demonstrate the ability to sustain or grow the current level of income even after the departure of the previous owner.

BOX 1: KEY VALUATION METHODOLOGIES

Appraisers can estimate the value of your trucking company using multiple techniques.

Discounted cash flow analysis: This technique involves forecasting the future cash flows of your trucking company over say 5 to 10 years, and discounting them back to the present using an appropriate discount rate.

Asset-based valuation: This technique involves valuing the trucking company based on the value of its assets, including both tangible assets (such as property and equipment) and intangible assets (such as patents, trademarks, customer relationships, or data).

Earnings multiple analysis: This technique involves determining the value of the trucking company based on revenue and/or profit and a multiple of such revenue/profit to arrive at a valuation. Reference points for multiples are typically public trucking companies’ PE or TEV/Rev ratios and the sale of private trucking companies, that get adjusted based on the subject carriers’ idiosyncrasies.

It's important to note that no single valuation technique is perfect, and it's often necessary to use a combination of techniques to arrive at a reliable estimate of value.

3. OPTIONS

Naturally, most trucking company owners deliberate a sale only after having assessed whether existing family members are able or willing to manage the business in the future. We acknowledge that this may take precedence over pure economic considerations which we outline in this section, but recommend owners to nevertheless assess a sale as one of the possible options to unlock wealth from the business and re-allocate their assets.

3.1. SELLING THE BUSINESS

We are proposing a few strategic questions that trucking company owners with an intent to sell should ask themselves to assess and maximize sales proceeds. This section may also be helpful in preparing the company for a sale a few years down the road. Many actions that can enhance the financial proceeds from a sale require time to improve the optics of strongpoints, or mitigate weaknesses in your trucking company today.

Unique strategic advantages: What unique competitive assets does the company have that no or few others possess? How do these affect the level and certainty of future profits?

Examples would be location advantages anchored by ownership or long-term leases of critical facilities or provide access to drivers and equipment in strategic locations.

Keyman risk: How much is the business anchored around the founder? How sustainable are profits after the founder exits from the business and is no longer personally involved? What incentives does the founder have to support an orderly transition whereby the value of the business stays intact?

Examples that show low keyman risk include governance and management structures that balance both delegation and critical controls in the organization, succession and transition plans as well as reliance on systems to maintain standard operating procedures even when ownership is not involved in the day-to-day.

Strategic synergies: Can a buyer unlock more value from the fleet than the seller? What buyer would that be?

An example would be a 3PL targeting large national accounts who can benefit from capacity in the location where the fleet is located. In that instance, the buyer may rely on its unique presence in a specific market to win national contracts for the rest of its business across the country, even though the fleet acquired serves only a small subset of it.

Market timing: Freight markets are cyclical. Understanding expected market trends can help to determine whether the multiple applied to your cash flows should be higher or lower than historical transactions. It is noteworthy that all sellers are exposed to market forces and market data is generally public information, meaning that market timing is not necessarily a source of unfair advantage, but can still offer certain advantages to a seller.

An example would be a trucking company that decides to sell shortly after freight rates have bottomed out. The owner understands and can convincingly relay that current profits are depressed and that the future is much brighter; this may be an easier sell than selling at the peak market where buyers are skeptical about the sustainability of revenues as everyone expects rates to decline.

Opportunities to bridge price gaps: What happens if you won’t secure the price you expect for your business? What flexibility do you have to bridge price gaps?

An example would be a trucking company owner expecting $30M for the business of which he needs to use $20M to pay off a loan on the company’s office building. What would he do if he could only secure $20M in a sales price?

3. OPTIONS

Naturally, most trucking company owners deliberate a sale only after having assessed whether existing family members are able or willing to manage the business in the future. We acknowledge that this may take precedence over pure economic considerations which we outline in this section, but recommend owners to nevertheless assess a sale as one of the possible options to unlock wealth from the business and re-allocate their assets.

3.1. SELLING THE BUSINESS

We are proposing a few strategic questions that trucking company owners with an intent to sell should ask themselves to assess and maximize sales proceeds. This section may also be helpful in preparing the company for a sale a few years down the road. Many actions that can enhance the financial proceeds from a sale require time to improve the optics of strongpoints, or mitigate weaknesses in your trucking company today.

Unique strategic advantages: What unique competitive assets does the company have that no or few others possess? How do these affect the level and certainty of future profits?

Examples would be location advantages anchored by ownership or long-term leases of critical facilities or provide access to drivers and equipment in strategic locations.

Keyman risk: How much is the business anchored around the founder? How sustainable are profits after the founder exits from the business and is no longer personally involved? What incentives does the founder have to support an orderly transition whereby the value of the business stays intact?

Examples that show low keyman risk include governance and management structures that balance both delegation and critical controls in the organization, succession and transition plans as well as reliance on systems to maintain standard operating procedures even when ownership is not involved in the day-to-day.

Strategic synergies: Can a buyer unlock more value from the fleet than the seller? What buyer would that be?

An example would be a 3PL targeting large national accounts who can benefit from capacity in the location where the fleet is located. In that instance, the buyer may rely on its unique presence in a specific market to win national contracts for the rest of its business across the country, even though the fleet acquired serves only a small subset of it.

Market timing: Freight markets are cyclical. Understanding expected market trends can help to determine whether the multiple applied to your cash flows should be higher or lower than historical transactions. It is noteworthy that all sellers are exposed to market forces and market data is generally public information, meaning that market timing is not necessarily a source of unfair advantage, but can still offer certain advantages to a seller.

An example would be a trucking company that decides to sell shortly after freight rates have bottomed out. The owner understands and can convincingly relay that current profits are depressed and that the future is much brighter; this may be an easier sell than selling at the peak market where buyers are skeptical about the sustainability of revenues as everyone expects rates to decline.

Opportunities to bridge price gaps: What happens if you won’t secure the price you expect for your business? What flexibility do you have to bridge price gaps?

An example would be a trucking company owner expecting $30M for the business of which he needs to use $20M to pay off a loan on the company’s office building. What would he do if he could only secure $20M in a sales price?

3.2. SUCCESSION PLANNING PASSING THE BUSINESS TO THE NEXT GENERATION

Operational Transition

Many family businesses are very efficiently managed because one key person has significant operational and fiscal control. That makes particular sense in smaller organizations or when ownership remains concentrated with one family member who is also heavily involved in the day-to-day business. That said, succession planning can be a great opportunity to unlock opportunities for growth.

Let’s break this down into a variety of aspects.

TRANSITIONING OPERATIONAL MANAGEMENT

Handing over day-to-day operations is a process that ownership is generally more familiar with as owners typically delegate certain tasks to staff . However, in many small and medium sized fleets, ownership still has deep operational involvement with core processes anchored around one or few individuals. One opportunity succession planning brings is to increase the company’s strength to generate sustainable cash flow irrespective of management and staff changes.

While many companies use a habitual way of managing the business, as in “this is the way we do things here”, many companies that scale their foot print use formalized SOPs or standard operating procedures. While SOP manuals were commonplace for a long time, today SOPs can be implemented via workflow technology. Technology can help ownership formalize, standardize and streamline processes all the while gathering data about activities and actions in this business. Implementing a sustainable, integrated and cohesive technology infrastructure can be the greatest opportunity a trucking company will see in the course of a hand over to the next generation. We found a few carriers who used this opportunity as a welcome project for the retiring generation to engage the next generation while ensuring they deeply understand the operational workings of the business.

BUILDING VISIBILITY

Trust can be one of the biggest hurdles to a smooth hand over to the next generation. Offering retiring managers continuous real time visibility into all aspects of the business can be one of the most powerful tools for new management to build trust. Visibility ultimately refers to real-time informational transparency that can be established easily with technology.

It is not uncommon that we see transportation businesses, especially those founded in the 1980s and 1990s, run on technology that has limited real-time capabilities. For instance, with one 750 driver carrier, we found that the CFO only gets a good picture of the financial state of the business 10 days after each months’

closing. With new transportation management and accounting systems properly integrated though, financial managers can reconcile management and financial reports, understanding the full state of the business at any given point in time. Cutting edge technology can therefore be a major facilitator to build transparency and trust and allows for continued mentorship by the retiring team.

MANAGEMENT CONTROLS GOVERNANCE CONTROLS  

On top of knowing what’s going on through real-time visibility, the retiring generation may also desire to phase out their involvement in critical operational decisions, transitioning control. Your technology stack, if properly developed, can facilitate not only the visibility that is offered, but also incorporate critical management controls into your business.   Transportation management and accounting systems can protect certain managerial controls for retiring owners, formalizing the need for managers to obtain their sign-off as workflows get routed back to them.   A second, helpful tool applicable in conjunction with governance controls is a control matrix that clearly outlines decisions that can be made by management (or different layers in management) with/without the involvement of more senior decision makers. Matrices typically cover the budgeting, commitment (contracting), and payment control processes and institutionalize controls for critical decisions (typically by level of materiality or dollar amounts).

Ownership Transition
Taking standard management controls one step further, is considering a clear   separation of “ownership” from “management” whereby a formal board of directors is established to safeguard ownership interests and to delegate managerial authority for non-major operational decisions to management. Formally defining board vs managerial discretion can be a helpful tool to empower the next generation with the retiring owner-managers retaining control and information rights over critical decisions that may affect the value of their ownership stake.   

There are three main ways to transition ownership of the trucking company. One option is selling to an external strategic buyer, such as a competitor or private equity The second option is an internal transition to key employees. The third option is transitioning to a family member through a sale or gifting. These options each have tax implications and impacts the business owner’s retirement plan and are discussed later in this paper.

3.2. SUCCESSION PLANNING PASSING THE BUSINESS TO THE NEXT GENERATION

Operational Transition

Many family businesses are very efficiently managed because one key person has significant operational and fiscal control. That makes particular sense in smaller organizations or when ownership remains concentrated with one family member who is also heavily involved in the day-to-day business. That said, succession planning can be a great opportunity to unlock opportunities for growth.

Let’s break this down into a variety of aspects.

TRANSITIONING OPERATIONAL MANAGEMENT

Handing over day-to-day operations is a process that ownership is generally more familiar with as owners typically delegate certain tasks to staff . However, in many small and medium sized fleets, ownership still has deep operational involvement with core processes anchored around one or few individuals. One opportunity succession planning brings is to increase the company’s strength to generate sustainable cash flow irrespective of management and staff changes.

While many companies use a habitual way of managing the business, as in “this is the way we do things here”, many companies that scale their foot print use formalized SOPs or standard operating procedures. While SOP manuals were commonplace for a long time, today SOPs can be implemented via workflow technology. Technology can help ownership formalize, standardize and streamline processes all the while gathering data about activities and actions in this business. Implementing a sustainable, integrated and cohesive technology infrastructure can be the greatest opportunity a trucking company will see in the course of a hand over to the next generation. We found a few carriers who used this opportunity as a welcome project for the retiring generation to engage the next generation while ensuring they deeply understand the operational workings of the business.

BUILDING VISIBILITY

Trust can be one of the biggest hurdles to a smooth hand over to the next generation. Offering retiring managers continuous real time visibility into all aspects of the business can be one of the most powerful tools for new management to build trust. Visibility ultimately refers to real-time informational transparency that can be established easily with technology.

It is not uncommon that we see transportation businesses, especially those founded in the 1980s and 1990s, run on technology that has limited real-time capabilities. For instance, with one 750 driver carrier, we found that the CFO only gets a good picture of the financial state of the business 10 days after each months’

closing. With new transportation management and accounting systems properly integrated though, financial managers can reconcile management and financial reports, understanding the full state of the business at any given point in time. Cutting edge technology can therefore be a major facilitator to build transparency and trust and allows for continued mentorship by the retiring team.

MANAGEMENT CONTROLS GOVERNANCE CONTROLS  

On top of knowing what’s going on through real-time visibility, the retiring generation may also desire to phase out their involvement in critical operational decisions, transitioning control. Your technology stack, if properly developed, can facilitate not only the visibility that is offered, but also incorporate critical management controls into your business.   Transportation management and accounting systems can protect certain managerial controls for retiring owners, formalizing the need for managers to obtain their sign-off as workflows get routed back to them.   A second, helpful tool applicable in conjunction with governance controls is a control matrix that clearly outlines decisions that can be made by management (or different layers in management) with/without the involvement of more senior decision makers. Matrices typically cover the budgeting, commitment (contracting), and payment control processes and institutionalize controls for critical decisions (typically by level of materiality or dollar amounts).

Ownership Transition
Taking standard management controls one step further, is considering a clear   separation of “ownership” from “management” whereby a formal board of directors is established to safeguard ownership interests and to delegate managerial authority for non-major operational decisions to management. Formally defining board vs managerial discretion can be a helpful tool to empower the next generation with the retiring owner-managers retaining control and information rights over critical decisions that may affect the value of their ownership stake.   

There are three main ways to transition ownership of the trucking company. One option is selling to an external strategic buyer, such as a competitor or private equity The second option is an internal transition to key employees. The third option is transitioning to a family member through a sale or gifting. These options each have tax implications and impacts the business owner’s retirement plan and are discussed later in this paper.

  1. CRITICAL CNSIDERATIONS

4.1. FINANCE CONSIDERATIONS

ENTITY PREPARATION FOR SALE

A transaction is the sum of many moving parts; from structuring and negotiating to managing the details and related parties. If your organization increases team accountability and avoids common pitfalls, your transaction’s close is more likely to achieve your goals.

Ensuring you have a deep understanding of your company’s critical performance metrics, are monitoring those metrics, and have clear and measurable strategies to enhance these metrics help demonstrate your ability to create future value.

The quality of the management team determines much of your company’s strength—and therefore much of your company’s value. A buyer will need to be confident your company will continue running smoothly once you’ve transitioned out of ownership. Establishing a strong management team and continuing to restructure the team to reflect your business’s growth or changing needs, can help instill greater buyer confidence.

Investing in professional accounting practices such as closing books at least monthly and having annual reviewed or audited financial statements creates an accountable and disciplined accounting department.

FINANCIAL PREPARATION FOR SALE

Knowing what you’ll face when due diligence begins—and preparing effectively—can help a company position itself for better negotiations, higher valuations, and stronger outcomes.

When it comes to selling all or a portion of your business, there’s no replacement for proactive pre-transaction planning and due diligence. Effective preparation not only readies your company for the transaction process, it improves the conditions of a sale.

Answering the following questions before you go to market can provide you with confidence in your position and help you avoid surprises:

Have you prepared a sell-side quality of earnings (Q of E) report?

Do you have annual financial statements that have been reviewed or audited?

Have you identified pro-forma adjustments to your financial statements for one-time non-recurring costs? Are your internal financial statements up-to-date? Have you identified non-GAAP accounting policies?

Do you know key risk areas present within your company?

Have you performed detailed reviews of all business and legal contracts?

Does your company have significant, uncertain tax positions or unasserted legal claims a buyer could identify?

Sell-side due diligence performed by a professional can help manage your internal resources and identify potential gaps.

One of the worst things that can happen during a sale process is for the buyer to discover a material issue that the owner was unaware of. This often results in a reduction of the purchase price, additional scrutiny in all areas of the business, or even termination of the transaction.

Choosing an investment banker or advisor who is well versed in your industry is crucial as they will be developing and helping you understand your company’s valuation model, demonstrating potential future value from synergies to buyers, and will lead the marketing and sale process of your company.

The below timeline and checklist can help prepare you for a successful transaction:

4.2.1  TAX CONSIDERATIONS

When selling a business, there are tax implications that should be considered, and if the transaction is not structured properly, it can lead to unexpected and higher tax liability than anticipated. If planning to transition the business (outside of just shutting down operations), there are really two options – selling the business or gifting the business. Selling the business is most common, although gifting is a popular option when transitioning the business within the family to the next generation.

Structuring the transition as a sale

Selling a business and then determining the tax liability is not as straight forward as just applying a tax rate times the selling price. There are many variables that impact the actual gain on the sale and the tax rate applied to the sale. The current federal tax rates as of 2023 that apply to the sale of a business include the long-term capital gains rate (up to 23.8% tax rate) ordinary tax rate (up to 37% tax rate) and/or corporation tax rate (up to 21% tax rate) plus applicable state income taxes (which range from 0% to over 13%, depending on the state).

The entity type of the business (C corporation, S corporation, partnership, LLC, or sole proprietorship) has an impact on the tax rate applied to the sale of a business. Generally, closely held businesses are an S corporation, partnership, LLC, or a sole proprietorship. Less common are C corporations .

There are advantages and disadvantages to the different entity structures. C corporations are subject to double-taxation

– meaning that if the deal is structured a certain way, the corporation would pay tax at the entity level and then the individual will pay taxes at the individual level when distributing the proceeds to the shareholder. For partnerships, LLC, S corporations and sole proprietorships, there is generally one layer of tax at the individual level which generally may lead to a lower tax rate on the sale. Please consult with your tax advisor for advice regarding the preferred entity type for your business structure.

In addition to the entity type of the business, how the deal is structured has major tax implications and ultimately what the owner’s net proceeds will be after taxes are paid. This includes whether the deal is structured as an asset deal (selling the assets, including goodwill of the business rather than the entity itself). The other type is a stock deal (basically selling the entity itself to the buyer). Each has its advantages and disadvantages based on the type of entity, structure of deal, basis in assets, etc.

Structuring the transition via gifting

The other common way to transition ownership is via gifting. Typically, this will be to a close relative, such as children that are already active in the business, although gifts can be made to anyone. With a closely held business, navigating the family dynamics of fairness and equity when gifting or selling a business to the next generation certainly presents challenges.

Using the strategy of gifting for ownership transition of the business has tax consequences, particularly with the combined gift/estate tax. Under current law, the 2023 lifetime exemption for gifting is $12,920,000 for an individual or $25,840,000 for a married couple. Once the lifetime exemption is used, anything gifted or remaining in the estate at death is taxed at approximately 40%. For business owners with highly valued companies, this can be significant transfer taxes. Please note, the current law is scheduled to sunset in 2025 and the available lifetime exemptions will be reduced significantly. Of course, legislative changes can always accelerate or defer this. In addition, many states have a state level estate and/or gift tax.

When considering a gift to the next generation, as opposed to a sale to them, it is often best to do this when the company value is low. This means planning as early as possible rather than waiting until the business owner is ready to make the gift. There are a variety of strategies with trusts that can help preserve wealth and allow thedon[1] [2] [3] or (likely the parents) to have more control over how the assets are managed after gifting. There are various strategies with trusts that can help pack in as much gifting as possible within the available lifetime exemption. Strategies include using a GRAT (Grantor Retained Annuity Trust), sale to an Intentionally Defective Grantor Trust (IDGT), and utilizing valuation discounts by gifting minority interests of the business.

4.2.2   PERSONAL FINANCIAL PLANNING    

In addition to the tax considerations when preparing for ownership transition of a business, there is a financial planning aspect that should be considered. For the business owner, they will need to ensure they have enough cash flow to sustain the rest of their lives. When going through the process of determining the fair market value of the business and tax impact from the sale, will that allow for enough net proceeds to comfortably fund the business owner’s retirement and accomplish their goals? Working with a financial planner to model out cash flows for the business owner’s retirement is very important. Will the business owner have enough to cover medical costs, fund philanthropic goals, afford travel, etc.? This process will likely impact whether the business is able to gift the business or what selling price is acceptable.  

4.3     TECHNOLOGY CONSIDERATIONS     Workflow technology has leapfrogged significantly over the recent 12 months thanks to concurrent forces. Firstly, automation has allowed new ways to streamline and digitize businesses. Secondly, rapid digitization of supply chains and all actors makes available unprecedented sources of data that can help improve the internal operations of a trucking company.   The acceleration in technology development is so large that trucking companies operating on outdated technology stack start realizing that the wrong tools and processes come at a real cost to their business that reduces competitiveness of their rates offered to shippers or brokers. A recent research conducted by BeyondTrucks finds that the average American trucking company spends approximately $9,700 per driver per year because of poor processes and tools.

For companies undergoing a sale or generational hand-over the indirect costs of a poor technology stack are even more material. We therefore suggest owners consider the following:

How does the current technology stack ensure that the company stays competitive and can maintain or even improve income levels after the handover?

How sustainable is your current technology provider: Is the technology provider institutionally funded? Does the provider have sustainable access to cutting-edge management and technology talent? Does the provider phase a generational transition and succession planning themselves?

Can the technology provider facilitate visibility, managerial and board control requirements after the hand-over? As previously discussed, we find this particularly important to handle the trust dynamics as old management retires and new management takes over and to institutionalize delegation.

How robust is the technology providers’ cyber security measures in place to ensure the assets and cash flows are not jeopardized by security attacks? Take the example of a 350-driver tanker carrier who felt on-prem systems are safe, got hacked and lost all historical data of the business. The carrier subsequently moved everything to a cloud-based transportation management provider who was offering SOC2 compliance.

How vertically integrated are your technology providers? Traditional legacy providers are often pure play software players, i.e. they are transportation management systems, document scan systems, HR management systems, accounting systems, or customer relationship management systems. Newer players have a stronger tendency to verticalize their stacks, not only saving money, but allowing for more streamlined management, higher levels of automation with less manual data input and fewer errors, better control, and even access to cheaper financial transactions.

Answering these questions is critical, as today every sustainable company has become a technology company and larger shifts in trucking technology on the horizon, including autonomy and electrification, will offer both massive opportunities and threats to players today.

4.2.2   PERSONAL FINANCIAL PLANNING    

In addition to the tax considerations when preparing for ownership transition of a business, there is a financial planning aspect that should be considered. For the business owner, they will need to ensure they have enough cash flow to sustain the rest of their lives. When going through the process of determining the fair market value of the business and tax impact from the sale, will that allow for enough net proceeds to comfortably fund the business owner’s retirement and accomplish their goals? Working with a financial planner to model out cash flows for the business owner’s retirement is very important. Will the business owner have enough to cover medical costs, fund philanthropic goals, afford travel, etc.? This process will likely impact whether the business is able to gift the business or what selling price is acceptable.  

4.3     TECHNOLOGY CONSIDERATIONS     Workflow technology has leapfrogged significantly over the recent 12 months thanks to concurrent forces. Firstly, automation has allowed new ways to streamline and digitize businesses. Secondly, rapid digitization of supply chains and all actors makes available unprecedented sources of data that can help improve the internal operations of a trucking company.   The acceleration in technology development is so large that trucking companies operating on outdated technology stack start realizing that the wrong tools and processes come at a real cost to their business that reduces competitiveness of their rates offered to shippers or brokers. A recent research conducted by BeyondTrucks finds that the average American trucking company spends approximately $9,700 per driver per year because of poor processes and tools.

For companies undergoing a sale or generational hand-over the indirect costs of a poor technology stack are even more material. We therefore suggest owners consider the following:

How does the current technology stack ensure that the company stays competitive and can maintain or even improve income levels after the handover?

How sustainable is your current technology provider: Is the technology provider institutionally funded? Does the provider have sustainable access to cutting-edge management and technology talent? Does the provider phase a generational transition and succession planning themselves?

Can the technology provider facilitate visibility, managerial and board control requirements after the hand-over? As previously discussed, we find this particularly important to handle the trust dynamics as old management retires and new management takes over and to institutionalize delegation.

How robust is the technology providers’ cyber security measures in place to ensure the assets and cash flows are not jeopardized by security attacks? Take the example of a 350-driver tanker carrier who felt on-prem systems are safe, got hacked and lost all historical data of the business. The carrier subsequently moved everything to a cloud-based transportation management provider who was offering SOC2 compliance.

How vertically integrated are your technology providers? Traditional legacy providers are often pure play software players, i.e. they are transportation management systems, document scan systems, HR management systems, accounting systems, or customer relationship management systems. Newer players have a stronger tendency to verticalize their stacks, not only saving money, but allowing for more streamlined management, higher levels of automation with less manual data input and fewer errors, better control, and even access to cheaper financial transactions.

Answering these questions is critical, as today every sustainable company has become a technology company and larger shifts in trucking technology on the horizon, including autonomy and electrification, will offer both massive opportunities and threats to players today.

5. CONCLUSION

Most mid-sized trucking companies founded in the 1980s and 1990s have become sizable, family-owned businesses. Their founders are assessing how to transition out of running the business, whilst protecting both the wealth and legacy they created.

We provided high-level guiding thoughts for family-owned carriers to assess the financial, tax and technology considerations involved in protecting the wealth and legacy created in their trucking and logistics businesses.

While this paper certainly does not provide the depth and breadth of discussion this complex topic actually deserves, we hope to offer an initial framework that can be helpful to owners in avoiding errors of high confidence, i.e. ignoring unknown unknowns, where the support of experts may have been warranted.

About the Authors

Mark Meier

Partner at Moss Adams

Over thirteen years of experience in public accounting. Currently the Office Tax Department Leader in Tacoma, and also serves as the Office Construction and Real Estate Industry Group Leader. Professional experience lies in developing tax efficient strategies for companies within many different industries. Responsible for tax planning, consulting, and compliance for corporations, partnerships, and individuals.

Over thirteen years of experience in public accounting. Currently the Office Tax Department Leader in Tacoma, and also serves as the Office Construction and Real Estate Industry Group Leader. Professional experience lies in developing tax efficient strategies for companies within many different industries. Responsible for tax planning, consulting, and compliance for corporations, partnerships, and individuals.

Over thirteen years of experience in public accounting. Currently the Office Tax Department Leader in Tacoma, and also serves as the Office Construction and Real Estate Industry Group Leader. Professional experience lies in developing tax efficient strategies for companies within many different industries. Responsible for tax planning, consulting, and compliance for corporations, partnerships, and individuals.

Terry Dickens

Tax Partner at Moss Adams

Terry Dickens – Terry has practiced public accounting since 2011. He leads the Private Clients Group in the Moss Adams San Francisco office. He serves closely held businesses and individuals. Additionally, Terry works in the firm’s China Practice, serving inbound and outbound clients from China and other parts of Asia. His focus areas include equity compensation, international cross-border services, business owner succession, charitable planning, and estate, gift and trust planning.

Terry Dickens – Terry has practiced public accounting since 2011. He leads the Private Clients Group in the Moss Adams San Francisco office. He serves closely held businesses and individuals. Additionally, Terry works in the firm’s China Practice, serving inbound and outbound clients from China and other parts of Asia. His focus areas include equity compensation, international cross-border services, business owner succession, charitable planning, and estate, gift and trust planning.

Terry Dickens – Terry has practiced public accounting since 2011. He leads the Private Clients Group in the Moss Adams San Francisco office. He serves closely held businesses and individuals. Additionally, Terry works in the firm’s China Practice, serving inbound and outbound clients from China and other parts of Asia. His focus areas include equity compensation, international cross-border services, business owner succession, charitable planning, and estate, gift and trust planning.

Jesse Proctor

Chief Growth Officer

Jesse Proctor – Provides corporate audit, review, transaction, and consulting services for clients in the manufacturing, transportation, and logistics industries. Jesse began his career at a Big Four firm and worked in private industry before joining Moss Adams and has practiced public accounting since 2007.

Jesse Proctor – Provides corporate audit, review, transaction, and consulting services for clients in the manufacturing, transportation, and logistics industries. Jesse began his career at a Big Four firm and worked in private industry before joining Moss Adams and has practiced public accounting since 2007.

Jesse Proctor – Provides corporate audit, review, transaction, and consulting services for clients in the manufacturing, transportation, and logistics industries. Jesse began his career at a Big Four firm and worked in private industry before joining Moss Adams and has practiced public accounting since 2007.

Hans Galland

CEO of BeyondTrucks

A former trucking company owner with a Stanford degree, private equity, and scaling businesses, Hans brings operational, strategic, and financial expertise to technology applications in the trucking industry. His team includes leading experts in fleet operations, workflow automation, data science, and finance. You may contact him at hans@beyondtrucks.com.

A former trucking company owner with a Stanford degree, private equity, and scaling businesses, Hans brings operational, strategic, and financial expertise to technology applications in the trucking industry. His team includes leading experts in fleet operations, workflow automation, data science, and finance. You may contact him at hans@beyondtrucks.com.

A former trucking company owner with a Stanford degree, private equity, and scaling businesses, Hans brings operational, strategic, and financial expertise to technology applications in the trucking industry. His team includes leading experts in fleet operations, workflow automation, data science, and finance. You may contact him at hans@beyondtrucks.com.